Invest Like the Best with Patrick O'Shaughnessy

My guest this week is Doug Leone. Doug led one of the world’s most successful venture firms, Sequoia, for over 25 years after he was given responsibility for the firm by its founder, Don Valentine, in 1996. Alongside Mike Moritz, the pair managed its expansion from a single $150m early-stage fund into an $85 billion global powerhouse. It was a privilege to sit down with Doug and learn from him. We talk about his tough start at Sequoia, get into the technicalities of great go-to-market motions, and survey his advice for other investors in the industry. A key theme that will stick with me from this conversation is Doug’s insistence on keeping things simple and clear. Please enjoy my great conversation with Doug Leone.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus, the modern research platform for leading investors. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:21] - [First question] - What Don Valentine’s heart was like [00:06:30] - The most productive and unproductive parts of Don’s toughness 

[00:09:01] - Being the opposite of insufferable and how it was different when he was younger

[00:10:55] - Why it’s so important to understand someone’s core motivations

[00:14:18] - Questions or topics he returns to when getting to know people 

[00:15:31] - How much time he believes it can take to really get to know someone  

[00:20:37] - What venture looks like to him today relative to his prior career

[00:23:51] - His style of approaching emerging technology markets like AI as an investor  

[00:26:37] - Whether or not he’d go into venture today if he was in his late 20s 

[00:28:30] - Commonalities between the very best at going to market effectively 

[00:31:11] - The key components of great product positioning  

[00:32:10] - Helping companies circumnavigate mediocre positioning 

[00:33:25] - Generating demand and leads and doing it well 

[00:37:15] - How interacting with companies early on has changed over the ears

[00:46:14] - Sussing out the killer gene in somebody 

[00:47:25] - What high school was like for him when he first came to the US 

[00:49:04] - How successful people can instill the lessons learned from hardship into their children 

[00:50:45] - The most common failure modes he’s seen for investors 

[00:55:21] - The early 2000s clawback at Sequoia and what navigating that period was like 

[00:59:06] - What he’s learned about picking the right LPs and partnering with them

[01:00:40] - The most interesting question an LP has ever asked him 

[01:02:18] - Making sure that performance is on everyone’s minds all the time 

[01:04:04] - What the components of a fantastic investment memo are

[01:05:00] - Which dinner companions he’d pick to educate a newly successful founder

[01:05:29] - What first popped out at him as black magic when he started investing

[01:07:59] - The kindest thing anyone has ever done for him 

I’m excited to share this conversation with Tim Urban. Tim is, in my opinion, one of the best and most engaging writers of our era. He’s tackled many of the most interesting topics in the world from AI to procrastination. I interviewed him in 2017 in an episode we called “Grand Theft Life”, and it remains one of my favorite episodes ever.

In the 6 years since that episode, he hasn’t published almost anything. That’s because he’s been writing the book we discuss in this episode. The book is called “What’s Our Problem”, in which Tim investigates the big issues facing society.

The reason I love Tim’s writing so much is its density of ideas and ridiculously clear explanations: a rare combo that makes reading a joy. I hope you enjoy this great round two with Tim Urban, and go buy and enjoy his great new book.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

Listen to Founders podcast.

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This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:50] - [First question] - What it’s been like spending seven years thinking about a single topic: Tim's book, What’s Our Problem?

[00:05:05] - How he’s come to articulate the big question he’s trying to answer in his book

[00:07:58] - A dinner experience where a single question showed just how much of a problem there was to solve

[00:09:47] - Group ideology and the different ladder rungs of human thinking 

[00:17:28] - The concept of a social golems and genies and their implications for society 

[00:23:02] - His favorite genies and golems throughout history and their impact  

[00:29:07] - Examples of canonical high functioning genies across history   

[00:34:20] - The key ingredients within liberal democracies that allow for and correct golems

[00:40:44] - Media’s role in shaping ideas and society and what’s changed about it in today’s media landscape 

[00:46:46] - What else is going on that has him worried about modern institutions that are failing as social immune systems

[01:01:15] - The gap between what we say publicly versus what we feel privately and the growing pile of unsaid things 

[01:07:18] - What’s to be done in order to help society repair itself 

[01:14:09] - Whether or not the direction we’re most afraid to run is where we should 

[01:17:37] - Thoughts on AI having written extensively on it and the new wave of emerging tools

[01:22:13] - The role and impact of leadership in regards to golems and genies 

My guest today is Dan Rose. Dan is the chairman of Coatue Ventures and has one of the most interesting collections of experiences of anyone I’ve talked to. He spent 20 years at Amazon and Facebook in their early days, working closely with Jeff Bezos, Andy Jassy, Mark Zuckerberg, and Sheryl Sandberg. He’s had a front-row seat to the defining products and founders of our era and his lessons from those experiences do not disappoint. Please enjoy this great discussion with Dan Rose.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:27] - [First question] - The story behind Amazon’s Kindle and the lessons it taught him

[00:09:19] - Amazon’s philosophy of working backwards and the most creative solutions he and his team had to come up inside of that framework 

[00:13:04] - What he did to convince publishers to get on board with his vision 

[00:16:02] - His overall experience of the relationship between innovation and constraints

[00:18:43] - Thoughts about the fine line between genius and nutcase 

[00:22:02] - What the key points of his theory on partnerships would be 

[00:24:28] - When advising portfolio companies becomes relevant 

[00:26:09] - The dark arts of building companies that could be adopted by partnerships 

[00:28:40] - Why he thinks the best technology companies drive strategy through product 

[00:32:23] - Resolving micro management while also giving skilled talent their own space

[00:36:07] - Where Javier Olivan fits into his ideal executive team 

[00:36:57] - What about growth requires its own expertise 

[00:37:35] - What makes Dave Schneider an ideal sales leader

[00:39:08] - The most stressful period of time while working at Facebook

[00:42:51] - General thoughts on great versus good business models in tech 

[00:45:36] - Topics where Jeff Bezos and Mark Zuckerberg would disagree the most 

[00:47:13] - Defining the platonic ideal of a great investor approaching corporate enterprises 

[00:50:25] - Overview of the investing environment we’re in today from coast to coast

[00:55:07] - What made Sheryl Sandberg so successful; Lean In

[01:00:35] - Why he started his career at Life Mastery selling personal growth seminars 

[01:05:47] - What will define the next generation of leaders 

[01:07:59] - A product he would build if he could that doesn’t exist yet

[01:08:59] - The kindest thing anyone has ever done for him 

My guest today is Jeff Green, the CEO and co-founder of advertising platform, The Trade Desk. The Trade Desk is the second advertising exchange Jeff has built, having sold his first venue to Microsoft in 2007. He started The Trade Desk in 2009 and has built it into a $30 billion public business. In our discussion, we talk about the parallels between The Trade Desk and an equity exchange, why Jeff chose to align with ad buyers not sellers, and how he shapes the culture of his firm. Please enjoy my conversation with Jeff Green.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

Listen to Founders podcast

Founders Episode #136 A Success Story: Estee Lauder 

Founders Episode #288 Ralph Lauren

Invest Like the Best with David Senra: Passion & Pain

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This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it’s quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:09] - [First question] - What he’s learned about human behavior and how it’s impacted his business

[00:05:45] - Big differences in generational and perennial behavior 

[00:06:56] - The strong link between vulnerability and creativity  

[00:07:42] - The necessary preconditions that allowed him to build Trade Desk the way he did

[00:10:53] - What it would have felt like as an early stage employee at Trade Desk 

[00:12:43] - The hardest parts about maintaining his type of company culture

[00:14:05] - How much of his company culture is interwoven systemically or whether it arises naturally based on talent choices

[00:15:59] - Defining what talent means to him and the dimensions of it that matter

[00:22:03] - What he’s learned about delivering messages effectively  

[00:23:49] - The founding story and history of Trade Desk 

[00:28:33] - How he thinks about the key stakeholder groups around Trade Desk’s platform

[00:30:50] - Figuring out who Trade Desk’s key customers were and identifying them writ large

[00:34:55] - The composition of the universe and market of those who buy advertising 

[00:36:11] - Practical product implications based on their choice of service 

[00:40:16] - Building inventory legibility and its dimensions and importance 

[00:47:55] - The time between the first line of code to a multi million dollar revenue stream

[00:50:29] - Markers for technology companies he’d look for that could achieve a similar scale 

[00:53:35] - How not being able to simulate poverty or hunger translates into his parenting 

[00:57:10] - Describing the margin differences between Trade Desk and Google

[00:59:00] - What stands out as the defining moment in his firm’s history 

[01:01:50] - The kindest thing anyone has ever done for him

My guest this week is Carl Kawaja. It’s the second time I’ve had Carl on the show and my first conversation with him is one I go back to often. Carl is a portfolio manager at Capital Group, where he’s quietly overseen a huge portfolio for decades. He is one of the top investors operating today as well as one of my favorite people. The investing world has changed quite a bit since Carl and I first spoke in mid-2021 so this was a great chance to use Carl’s curious mind and wide range of experiences to discuss the regime change taking place across capital markets. In true Kawaja fashion, we go all over the map and discuss Apple, the Amazonian rainforest, baseball, the oil & gas industry, Muhammad Ali, and more. Please enjoy my great discussion with Carl Kawaja.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus, the modern research platform for leading investors. I’m a longtime user and advocate of Tegus, a company that I’ve been so consistently impressed with that last fall my firm, Positive Sum, invested $20M to support Tegus’ mission to expand its product ecosystem. Whether it's quantitative analysis, company disclosures, management presentations, earnings calls - Tegus has tools for every step of your investment research. They even have over 4000 fully driveable financial models. Tegus’ maniacal focus on quality, as well as its depth, breadth and recency of content makes it the one-stop, end-to-end research platform for investors. Move faster, gather deep research to build conviction and surface high-quality, alpha-driving insights to find your differentiated edge with Tegus. As a listener, you can take the Tegus platform for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:44] - [First question] - What the market feels like to him today

[00:06:00] - The pros and cons of the cost of capital and experimentation

[00:09:09] - Things we can learn from Oil & Gas stocks and resource commodities in general

[00:14:38] - Pulling apart the key lessons from Berkshire’s purchases of IBM and Apple

[00:20:37] - The practical implications of wanting to land more soft-wins in investing that aren’t apparent out of the gate

[00:25:52] - How he approaches and considers products and product cycles writ large

[00:31:10] - The Systems Bible

[00:33:15] - Thoughts about making money from value based strategies 

[00:38:31] - His methodology to go about finding the next diamond in the rough 

[00:42:48] - A New Innings

[00:45:13] - The Arc of Boxing; Lessons from Muhammad Ali fighting Cleveland Williams

[00:48:54] - Someone he thinks is an exemplar in both business and the world

[00:54:37] - Don’t Sleep There Are Snakes

[00:59:41] - The role fossil fuels play in the energy transition and the current regime change 

[01:07:35] - What we can learn from uncontroversial transitions in the past

My guest this week is Daryl Morey, who is President of basketball operations for the Philadelphia 76ers. Daryl is a computer science graduate but has become one of the NBA’s most successful General Managers during his time with the Houston Rockets and the 76ers. Together with my friend and past guest of the show, Sam Hinkie, Daryl pioneered the analytics movement in basketball. He’s been so influential his style has its own name, “Moreyball”, a nod to Michael Lewis’s book about baseball, Moneyball. Daryl is also the co-founder of the MIT Sloan Sports Analytics Conference, which has become the gold standard forum for leaders in sports analytics. I had a blast talking to him about negotiation tactics, systems thinking, hiring, and a ton more. Please enjoy this great conversation with Daryl Morey.

Listen to Founders podcast

Founders Episode #136 A Success Story: Estee Lauder 

Invest Like the Best with David Senra: Passion & Pain

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:15] - [First question] - The basic principles of sports and what makes for a great sport

[00:09:54] - How resource concentration influences outcomes in various sports

[00:13:13] - The degree of certainty in predicting sports outcomes based on existing data

[00:16:32] - Using the concept of KPIs to optimize for certain characteristics to win games

[00:18:45] - Training teams on specific systems and plays versus leveraging individual talent

[00:21:07] - Why superstar athletes are key to success in basketball

[00:24:02] - Dealing with constant expected value calculations to appease stakeholders

[00:25:30] - Building the organization’s back office to find talented athletes

[00:28:32] - How he and other GMs make organization-level decisions

[00:34:12] - Why he’s involved with basketball as opposed to other sports

[00:36:17] - How he uses his frameworks to figure out systems outside of mainstream sports

[00:37:41] - Problems with the rules and economic factors of professional soccer

[00:42:54] - Trends he’s observed in the worlds of music, movies, and books

[00:45:33] - His perspective on developing one’s own career path

[00:48:22] - How challenges in his youth benefited him in the long run

[00:49:28] - The person he would call for advice if he was stuck in a foreign prison

[00:51:01] - His emphasis on first principles and why he supports free speech

[00:52:31] - Takeaways from a Harvard negotiation class he took

[00:57:07] - The power of refining the terms and definitions of a deal post-negotiation

[00:58:51] - The four people in the world that intrigue him most

[01:01:40] - The kindest thing anyone has ever done for him 

My guest today is Miles Grimshaw. Miles is in his early thirties and is a General Partner at Benchmark. His experience and success belie his age. He was an early investor in Segment, Benchling, and Airtable, all before they had 30 employees. I have learned a ton from Miles about software investing and that’s why I was excited to have him on the show. We discuss his biological approach to investing, whether pure API companies can be good businesses, and what most has his attention right now. Please enjoy this conversation with Miles Grimshaw.

Listen to Founders podcast

Founders Episode #136 A Success Story: Estee Lauder 

Invest Like the Best with David Senra: Passion & Pain

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:57] - [First question] - His notion of the investor as a biologist or a physicist

[00:05:24] - Why he seeks out new companies with unique business models

[00:07:53] - How his investments are based on present and future needs in the market

[00:11:55] - Evaluating the genetics of a nascent or small company

[00:13:38] - The half-life of information as it flows through a company or platform

[00:17:26] - Unpacking how software companies can survive re-evaluation periods

[00:21:03] - The power of environment creation and facilitation

[00:25:10] - The importance of user conferences

[00:25:45] - A company’s potential for a differentiated second act as a sign of good genes

[00:30:21] - Product quality, timing, and reinvention in tech startups

[00:33:10] - Why it’s crucial for companies to avoid copying their heroes

[00:37:41] - Breaking down market perspective on pure API companies

[00:41:29] - His views on software targeted to vertical versus horizontal markets

[00:44:29] - Carefully leveraging relationships with core customers

[00:48:06] - Operational lessons from his experience with the companies he’s invested in

[00:50:26] - His maxim that software development is as much an art as a science

[00:51:12] - His idea of a product magician in the software industry

[00:52:19] - Effects of new products and categories at the forefront of the space

[00:58:21] - How software founders should prepare for 2023

[01:01:41] - How both market structure and product shape the genetics of a business

[01:04:32] - The challenge of pricing and packaging for SaaS companies

[01:06:42] - Cardinal sins in software investing

[01:07:42] - The kindest thing anyone has ever done for him

My guest today is John Fiorentino. John is a product inventor and entrepreneur who, in the space of a few years, has bootstrapped four products; Gravity Blanket, Moon Pod, Moon Pals, and Birthdate Candles which have collectively sold hundreds of millions of dollars of revenue. Our conversation is quite different than normal. Alongside his successful brands, John has had a range of life experiences – from starting as a Jazz musician to working for Justin Bieber - that give him an original worldview. I was especially interested in his points around product positioning, creating magic for consumers, not letting yourself become the product, and how to build enduring brands. Please enjoy this great conversation with John Fiorentino.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:25] - [First question] - The amazing story behind Gravity Blanket

[00:08:51] - What he’s learned about positioning relative to product

[00:13:17] - How fundamental truths drive creativity in commerce

[00:16:17] - Real-world examples of magic as he defines it

[00:19:50] - The investability of consumer businesses from his perspective

[00:25:25] - His contrarian thoughts on venture-backed startups

[00:28:00] - How unique personalities create compelling IP and monetize it

[00:38:28] - The fine line between creative power and self-destruction for brand founders

[00:45:13] - The importance of consumer business goals being larger than oneself

[00:48:45] - The story of the Moon Pals weighted stuffed animals

[00:53:15] - How investors undervalue IP and mythology

[00:57:20] - Leveraging uniqueness as a founder to boost your brand power

[01:00:53] - His eye-opening experience working on Justin Bieber’s team

[01:05:20] - How he identifies potential magic-makers and enables them

[01:09:16] - An odd commonality between high-level successful people

[01:12:14] - Whether or not one could map out their own archetype framework

[01:15:23] - The dangers of focusing on one’s own persona and image as the product

[01:18:19] - The kindest thing anyone has ever done for him

My guest today is Amjad Masad. Amjad is the founder and CEO of Replit, whose mission is to bring the next billion software creators online. Replit has built a browser-based coding environment that makes coding more fun, collaborative, and approachable. We discuss how that is possible and why the way most of us interact with computers today is suboptimal. We then go into the effects of AI on software creation and its broader impacts on technology. Please enjoy my conversation with Amjad Masad.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes[00:02:18] - [First question] - The Steve Jobs black-pill 

[00:06:02] - Speculation on the near future of programming

[00:09:38] - Potential convergence of simple software and coding tools

[00:11:23] - What an IDE is and how it works

[00:12:44] - The definition of REPL and the role of Replit in the space

[00:14:21] - Decreasing friction in a programming environment using primitives

[00:19:47] - Real-world effects of Replit’s low-friction design

[00:23:27] - His perspective on new coding and AI technologies

[00:30:29] - Promises and limitations of the user-friendly programming movement

[00:33:16] - The dynamic nature of IDE technology and its challenges

[00:39:53] - How he’s priming his team to react to new technologies like the upcoming GPT-4

[00:43:58] - Recommended skills and training for the AI world of the future

[00:47:21] - The impact of IDE and AI tech innovations on existing tech giants

[00:51:56] - His mixed but optimistic views on the trajectory of AI

[00:54:40] - Recommendations for the curious listener without a programming background

[00:56:50] - The role of smartphones in the IDE movement

[00:58:28] - The kindest thing anyone has ever done for him

My guest this week is Rebecca Lynn. Rebecca co-founded early-stage investor Canvas Ventures in 2013 and is regularly featured as one of the best VCs in the market. She has deep positioning and go-to-market experience, which she honed during her time at Procter & Gamble, and that's the focus of our discussion. We cover the details of great marketing, why you should say no to customers, and how she has built Canvas. Please enjoy my discussion with Rebecca Lynn.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:37] - [First question] - What she’d do a great job teaching if she could teach a singular 401 level course

[00:05:20] - Defining what the umbrella concept is 

[00:06:10] - What about her career at P&G applies most to the kinds of companies she spends her time with now 

[00:12:06] - What types of questions she asks to help someone building a product understand their marketing angle 

[00:15:34] - The top three things people do wrong when running a survey in tactics or strategy

[00:19:33] - Categories of questions where surveys are always helpful and effective   

[00:21:06] - What the Go-To-Market Council is and what it does 

[00:28:21] - The ways that most funnels are commonly broken  

[00:31:17] - Defining great positioning and what it accomplishes

[00:33:36] - How her knowledge and ideas most impacted the way she built Canvas

[00:35:04] - Lessons learned about the world of digital health and the quantified self  

[00:39:15] - The base level attributes that most indicate investment potential when she’s investing in a company

[00:42:32] - The shifts in the world that most have her attention today

[00:46:10] - What has her worried systemically about venture investing 

[00:49:37] - The kindest thing anyone has ever done for her 

My guest this week is Michael Mauboussin. Many of you will know Michael and his work well. He’s Head of Consilient Research at Counterpoint Global, one of the sharpest investment minds I know, and a frequent guest on this show. In this discussion, we go deep into his recent work on market share, returns on capital, and capital allocation - all of which are coming under increasing scrutiny for different reasons. Please enjoy this great conversation with my friend Michael Mauboussin.

Listen to Founders podcast

Founders Episode #136 A Success Story: Estee Lauder 

Invest Like the Best with David Senra: Passion & Pain

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:46] - [First question] - Overview of Michael’s recent research on market share

[00:05:48] - Market share dynamics in modern history

[00:08:43] - How market share data is useful for investors

[00:12:30] - Investing in early breakout companies from low-concentration markets

[00:14:34] - Surprises from his recent research project

[00:15:29] - Using the value stick for stakeholder satisfaction

[00:19:12] - Examples of value creation using the value stick

[00:23:33] - Market power in relation to markups and willingness to pay

[00:32:00] - Identifying a company’s real ROIC numbers

[00:44:00] - How important absolute ROIC is when picking investments

[00:47:07] - Research on capital generation and allocation trends

[00:54:25] - Characteristics of great capital allocation strategies

[00:59:26] - Surprises in the market since his deep-dive research

[01:02:54] - Artificial intelligence and other sources of disruptive innovation

My guest this week is Jeremiah Lowin. Jeremiah has been on the podcast a number of times over the years. He’s one of my oldest friends who has been a sounding board for me throughout my career. Today he is the founder and CEO of Prefect, which helps companies automate and orchestrate their dataflows. In full disclosure, Positive Sum is an investor in Prefect. We didn’t plan this conversation, but when OpenAI released ChatGPT, I called Jeremiah for a primer on what’s happening under the hood and how best to contextualize this product amidst the growing AI movement. We have these conversations often, but this time I decided to record it so we can all learn from someone I consider to be a leading mind in the fields of data science and machine learning. We start off in the weeds and zoom out as the discussion unfolds. Please enjoy this conversation with my friend, Jeremiah Lowin.

Listen to Founders podcast

Founders Episode #136 A Success Story: Estee Lauder 

Invest Like the Best with David Senra: Passion & Pain

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:38] - [First question] - What a pre-trained transformer is 

[00:06:12] - What latent representation means in the context of AI models 

[00:09:57] - Models using math to interpret input data and generate images accurately 

[00:11:43] - Whether or not understanding AI complexity in light of the results they arrive at will become a black box scenario 

[00:14:13] - A high level history of the companies involved in generative AI

[00:17:51] - The precursory technology that makes generative AI art possible

[00:21:01] - What people are doing to improve AI models in between versions 

[00:26:39] - Things that are literally happening during AI training

[00:33:38] - Whether or not AI models might one day function as a utility like electricity

[00:36:01] - Coding using GitHub Copilot and what it’s felt like to use it 

[00:40:30] - How he’d approach starting an AI company from scratch 

[00:44:40] - Developing this technology beyond general and into specific use cases

[00:49:44] - The secret sauce for defensibility in the AI model space 

[00:53:02] - What he’s watching more closely as the story unfolds 

[00:56:32] - Whether or not he thinks that these toolkits will eventually learn how to use other systems like Unreal Engine on our behalf 

My guest today is Bill Lenehan. Bill is the CEO of Four Corners Property Trust, a listed REIT and one of the leading owners of restaurant real estate in the US. Their portfolio is made up of 982 properties across 47 states. Real estate is something most of us own, whether as an investment or a home, and Bill’s insight into the asset class at this particular moment in time is fascinating to hear. Please enjoy my conversation with Bill Lenehan.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. We did so because we feel that Tegus will be the gold standard platform for investing research for decades to come. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:19] - [First question] - Recent increases in mortgage rates and a frozen housing market

[00:08:55] - Projected real estate trends over the next decade

[00:13:38] - How a company’s ROI can be more consistent with backing from a real estate firm

[00:16:41] - Risk-return rate and risk exposure in real estate compared to other asset classes

[00:20:09] - The skills, traits, and circumstances that make a top-level real estate investor

[00:22:38] - Stand-out learnings from his time at Farallon Capital Management

[00:33:20] - The value of shopping malls and offices in a post-COVID, e-commerce US

[00:39:27] - Pros and cons of different types of real estate investments, including REITs

[00:43:22] - The impact of climate change on the real estate market

[00:45:39] - The role of modern technology in investing and in real estate infrastructure

[00:51:10] - Hard costs of building and renovating for the future

[00:54:20] - How hard costs and supply levels impact rates of return and housing costs

[00:57:17] - How the retail industry is adapting to consumer trends

[01:01:23] - Why retailers need to adapt to a changing economy and how they’ll do it

[01:04:03] - The relative magnitude of change in today’s real estate market

[01:06:51] - The role health and wellness plays in real estate and finance

[01:09:28] - What it feels like to be investing in 2022

[01:12:23] - The kindest thing anyone has ever done for him

Today I’m joined by two Hollywood greats, Ron Howard and Brian Grazer. They have produced, directed, written, and acted in a number of the most popular films and tv shows ever made, including Apollo 13, A Beautiful Mind, 24, and Frost/Nixon. Their partnership is one of the longest running in Hollywood, and the business they founded in 1985, Imagine Entertainment, has won 49 EMMY awards, 11 Golden Globes, and 10 Academy Awards. There are few better storytellers in the world and it was a thrill to talk about curiosity, trust, and business building with them both. Please enjoy this great conversation with Ron Howard and Brian Grazer.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. 

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:44] - [First question] - The value of trust and how Ron built it up over time with Brian

[00:08:34] - The spark that allowed Brian to trust and work with Ron 

[00:14:45] - Ray Stark calling Brian and threatening him over their mermaid movie

[00:16:37] - Keeping their creative spark alive as their business scaled and matured 

[00:20:20] - Principals like the universality concept that they return to most commonly 

[00:23:24] - Seemingly bottomless wells of inspiration that they both pull from

[00:26:18] - Curiosity precedes innovation and the curiosity conversations Brian has

[00:30:15] - The pitch format Brian uses to try and secure a guest for a curiosity talk

[00:32:16] - The role of engaging with conversations or ideas Brian disagrees with 

[00:33:56] - How curiosity shapes the nitty gritty of Ron’s directing and producing 

[00:37:41] - The biggest mistakes they’ve come across that people make telling stories

[00:40:27] - Pinpointing the defining moments of their careers outside of the obvious wins

[00:44:27] - Thoughts about how the industry has changed across their careers

[00:47:19] - How they’ve gotten better at taking a project from nothing to the finish line 

[00:49:53] - The kindest things anyone has ever done for them  

Today’s episode is a special one, in a format that may turn into a series. It is a conversation between Ravi Gupta and Shane Battier. Ravi is a partner at Sequoia, one of our most popular past guests, and a good friend. Shane is Ravi’s friend, and one of the most successful basketball players ever, having won championships and awards at the high school, college, and NBA levels.

I spent 10 years as a purely quantitative investor, so naturally I was obsessed with data in sports. When I was meeting with prospective investors, Michael Lewis’s book Moneyball—which chronicled the data analytics revolution in baseball—was my go-to analogy to explain what I did… “Moneyball, but for investing.” I used that line for years.

I’ve learned firsthand that it’s wise to follow your curiosity, no matter how strange or different it may be. The podcast is my curiosity tour, and years ago it led me to Sam Hinkie—who is himself on the Mt. Rushmore of analytics in sports. Sam introduced me to Ravi. Then Ravi sent me Michael Lewis’ article written about Shane called “The No Stats All-Star.” I highly recommend you read it.

All this serendipity around friends, data, investing, and sports gave me an idea: why not ask Ravi to interview Shane? Ravi likes the idea of playing for the front of the jersey, not the back. It is hard to imagine someone that lived that more than Shane. Shane shares his story, lessons learned from various coaches, and using data as an advantage. He also explains the four kinds of teams he’s encountered, which I found simple, and memorable.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. 

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:53] - [First question] - What people measure in basketball, what matters when it comes to winning, and why he was called a replaceable cog in the No-Stats All-Star

[00:08:38] - Some of the plays that impact the overall points during a basketball game

[00:14:33] - The power of curiosity and obsessing over details

[00:16:16] - Embracing his role and how being a role player applies to life outside of the court

[00:20:47] - Where his obsession for winning and being a good team mate comes from 

[00:23:23] - Some of the things great leaders and coaches did to inspire him 

[00:28:51] - An overview of the four types of teams and fundamental aspects of them

[00:34:50] - What a person can do to elevate their team and make it a winning one 

[00:37:43] - Antifragility and the letter Shane wrote for Ravi when Amazon bought Whole Foods

[00:44:56] - How to get everyone rallied around a long-term shared mission effectively  

[00:46:48] - Finding a No-Stats All-Star in a company and what to look for in one

[00:52:34] - The kindest thing anyone has ever done for him

My guest today is Parker Conrad, co-founder and CEO of Rippling. I wanted to speak to Parker because he is building Rippling in a way that we don’t come across often. Rather than focus narrowly on one product, he is building a suite of interrelated products simultaneously to carry out the functions of HR, Finance, and IT for companies. He calls it a compound company and we discuss the idea, as well as some of his other non-traditional theories, in detail. Please enjoy this conversation with Parker Conrad.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. 

-----

This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:36] - [First question] - Overview of what a compound startup is 

[00:06:32] - What he’s learned about picking customers effectively 

[00:08:48] - Key chapters when it comes to building a compound startup 

[00:13:48] - What great looks like at the base level infrastructure of employee data

[00:20:15] - His overall philosophy on product development writ large 

[00:25:09] - His role as a capital allocator and distributing resources to his teams

[00:27:19] - The amount of products they offer and whether or not there’s a tradeoff between time, cost, and quality when building software

[00:31:36] - Possibly incorporating an app-like store on top of their existing infrastructure 

[00:34:43] - Speed and the kinds of people that can sustain it for long periods of time

[00:36:30] - What motivates him on a personal level and harnessing motivation in general

[00:42:31] - Whether or not there’s an end to feeling hurt by false public perceptions when building in public

[00:44:12] - The intersection of leadership and communication inside of a business and what he’s learned about great communication 

[00:48:00] - The paradox of how focusing on non-scalable actions perpetuates growth and productivity and his views on productivity-per-person

[00:50:36] - The best example of a moment that required the most grit and perseverance while building his company 

[00:52:28] - How to successfully get former founders to come work for him 

[00:54:47] - What good private equity investors do 

[00:58:31] - The kindest thing anyone has ever done for him

My guest today is Bob Elliott, the CEO and CIO of Unlimited, which creates low-cost index ETFs for alternative investment strategies. Prior to co-founding Unlimited, Bob was a senior investment executive at Bridgewater Associates where he served on their investment committee and led Ray Dalio’s personal research team for a decade. His breadth and depth of experience makes him a great person to assess the current macro landscape. We discuss the relationship between rates, inflation, and asset classes, Bob's approach to identifying data with the most signal, and finish with his view on quantitative strategies in private markets. Please enjoy this great discussion with Bob Elliott.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. 

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:45] - [First question] - The Economic Organization of a POW Camp and key lessons one can learn from the paper

[00:07:22] - The way that supply and demand clears a price and how that plays into his thinking about investing across asset classes 

[00:09:58] - Whether or not he has a generalized investing worldview or framework

[00:11:46] - Deciding on what data is signal and matters most when analyzing markets 

[00:15:46] - A crash course on easy money and tight money regimes and the implications of both in a macro environment 

[00:20:28] - The rise and role of inflation and what should be done about it

[00:24:00] - What the next couple of years will look like if we draw lessons from history

[00:30:12] - Why gold could ever belong in someone's portfolio when it doesn’t produce or yield anything back to the investor 

[00:35:08] - Supply and demand constraints and the state of the housing market today 

[00:40:42] - What might happen in future labor markets given our current macro environment

[00:46:27] - Currencies, energy, geopolitics, and what he’s most focused on globally

[00:52:19] - What movements in the charts are worrying him the most 

[00:56:04] - The original “All Weather” portfolio and what one would look like if he built it today

[01:02:05] - How his career has taught him to find talented individuals who might deliver alpha

[01:07:19] - Lessons learned from early-stage and venture investing and thoughts on that world now

[01:12:41] - Why there hasn’t been an iconic early-stage technology investing firm driven by systematic strategies

[01:16:10] - The kindest thing anyone has ever done for him 

My guest today is Kirsten Green, founder and managing partner at Forerunner Ventures. Kirsten launched Forerunner in 2012 and has built it into a leading consumer-focused venture firm with early investments in consumer brands like Dollar Shave Club, Bonobos, Faire, and Warby Parker. Our conversation is an exploration of consumer behavior and how to invest behind change in our society. We also discuss frameworks for identifying brands early, how to build deal flow, and the shift in power between buyers and sellers. Please enjoy my conversation with Kirsten Green.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com. 

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:35] - [First question] - The insights gleaned from studying consumers in the modern era

[00:07:02] - Whether or not the shift in consumer behavior is similar to a platform shift like mobile

[00:09:58] - Which of her hypothesis going into the research was proven most wrong

[00:11:31] - The leading persona archetype that drives consumer spending 

[00:13:58] - Thoughts about her investing focus after doing all of this research 

[00:16:23] - How much the digital world is good and bad for community

[00:18:50] - Positive and negative impacts digital access has on children

[00:21:17] - The investing criteria that she and her firm have developed for founders and business models they find desirable 

[00:32:00] - The beachhead problem for entry points, encouraging good focus and entry point selection, and who’s done it well 

[00:35:33] - The history of the consumer of how they buy and sell and where the shifts in power have been 

[00:39:47] - Other interesting trends she’s seeing in the seller empowerment era

[00:43:35] - How different her investing models are for linear product businesses

[00:46:45] - Frameworks she’s developed for evaluating a brand early on 

[00:49:57] - The most defining moment in Forerunner’s history and the hardest lesson she’s had to learn 

[00:53:13] - Ways she’s fostered and mentored young investors at Forerunner 

[00:54:04] - What the most underappreciated thing is today about the consumer

[00:54:50] - User and customer development strategies that work well for early stage products

[00:56:26] - Three businesses young investors should study to educate themselves on great consumer businesses; Shoe Dog

[00:59:49] - Where they find the companies Forerunner tends to invest in, and how to build and effective deal flow pipeline 

[01:05:07] - The kindest thing anyone has ever done for her

My guest today is Jason Droege, a venture partner at Benchmark. Jason’s had a long entrepreneurial career, which most recently culminated in building and leading Uber Eats. He joined Uber in 2014 with a blank piece of paper to grow the business beyond ride sharing. Within six years, he found product market fit with food delivery, refined the service, and scaled Uber Eats to a global $20 billion GMV run rate. Our conversation pulls out the most important lessons learned during that period and how Jason now employs them in his role at Benchmark. Please enjoy this great conversation with Jason Droege.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:52] - [First question] - What it was like at a high level building Uber Eats

[00:07:38] - How he would structure entrepreneurial incentives on a platform like Uber for a new leader or team attempting to build on top of it

[00:10:17] - What he learned about selecting competitive frontiers and mistakes made while building Uber Eats

[00:15:17] - Things that Uber Eats got most right that he’s proud of 

[00:18:16] - Constructive mistakes that taught him a lot from his time with Uber Eats

[00:20:36] - What made India such a competitive environment 

[00:26:13] - What improved the most in his playbook for launching in a new city

[00:27:14] - Defining what best means in this competitive sector  

[00:29:01] - Dealing with suppliers in different categories and finding an ideal balance

[00:32:09] - When monogamy between the buyer and supplier matters and when it doesn’t in a marketplace 

[00:36:12] - Defining what founder market fit is and being “fingertippy”

[00:37:29] - His views on the relationships between leaders of businesses and their cultures

[00:40:26] - Why Uber believed in him more than he did 

[00:41:40] - What he learned about marketing to suppliers specifically 

[00:45:18] - Differing views he has on the concept of failure  

[00:47:31] - Thoughts about ideas versus execution and the relative importance of the two

[00:49:10] - Effectively measuring opportunity cost and using it in decision making  

[00:58:56] - The most interesting things he’s learned from his time as a partner at Benchmark

[01:00:15] - The kindest thing anyone has ever done for him

My guest today is Paul Orfalea. Paul founded Kinkos, the popular copy chain, in 1970. He started with a single photocopy shop in California and grew the business into a $2 billion multinational operation over the course of his 30 years in charge. Paul is a non-traditional leader in the best sense and we discuss his philosophy of business building, from why your subordinates should frustrate you, why you shouldn’t love your business and tips he learned on hiring well. Please enjoy this conversation with Paul Orfalea. 

Founders podcast on Paul Orfalea.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:58] - [First question] - What it was like to be a very bad student in highschool

[00:04:22] - When he first realized he was unemployable

[00:05:02] - The origin story of the very first Kinko’s

[00:07:53] - Finding what has worked well in each Kinko’s and coaching managers

[00:11:45] - The difference of working on and not in the business

[00:13:57] - Why a good salesperson will sell you broke  

[00:15:36] - Why he teaches, what he teaches, and his teaching style

[00:18:31] - Explaining the Federal Reserve in two minutes  

[00:21:58] - The role of anger in his career and something he’s worked on over time

[00:22:31] - Where Kinko’s falls on the spectrum of bad to great businesses

[00:26:18] - Lessons learned about using the word employee

[00:27:21] - The most clever marketing strategy he ever deployed or designed

[00:27:45] - Learning to spread the glory instead of the money  

[00:28:30] - The state of entrepreneurship today compared to when he started 

[00:30:42] - What motivated him across his career

[00:31:35] - Why being in it for the money seems odd in today’s lens

[00:32:34] - Who he most admired or most admires today 

[00:32:51] - Let My People Go Surfing: The Education of a Reluctant Businessman

[00:33:08] - Preserving the alignment of integrity and action 

[00:34:57] - How good he is naturally with numbers and math being dyslexic 

[00:38:05] - His parents’ impression of him while he was building Kinko’s 

[00:39:56] - The most interesting person he’s ever worked with at Kinko’s

[00:40:48] - What he would have done differently if he started from scratch

[00:41:24] - Something that is most underappreciated about the United States 

[00:43:00] - The kindest thing anyone has ever done for him 

[00:43:57] - A big lesson he’s earned in a deeper way that he wishes he could share with others

My guest today is Madhavan Ramanujam. Madhavan quite literally wrote the book on how to price products, it’s called “Monetizing Innovations” and his concepts have been used by companies across the world like Porsche, Uber, LinkedIn, and SuperHuman. Our conversation is a masterclass on pricing. We discuss common mistakes when pricing products, why you need to focus on benefits rather than features, and how to pick the right monetization model. Please enjoy my conversation with Madhavan Ramanujam.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. I’ve been so impressed by the platform that my firm, Positive Sum, recently made an investment in Tegus. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:48] - [First question] - How he arrived at a radically different way of building products

[00:05:07] - An example of coming up with a price before the product

[00:08:35] - Distinctions between a willingness to pay and positive feedback 

[00:10:29] - How to make sure you’re talking to the right potential customer in the first place

[00:13:32] - Productizing for different customer segments 

[00:16:16] - Questions companies should be asking to get accurate feedback

[00:21:18] - What he’s learned about the motivations of potential buyers

[00:22:43] - What leaders, killers, and fillers are

[00:24:37] - Some of the biggest mistakes companies make while following his formula

[00:25:35] - A rule of thumb for what is a benefit versus a feature

[00:27:35] - Five distinct pricing models for charging a customer

[00:30:46] - Whether or not the value piece of all of this revolves around time and money

[00:33:27] - What he tells entrepreneurs about pricing their products that most surprises them 

[00:35:16] - Defining the first four categories of failure 

[00:40:13] - Reasons why so many innovations fail to monetize and pricing being a CEO topic

[00:41:51] - Good rules that leaders can use to have a general sense for effective pricing 

[00:47:38] - Behavioral changes and observations as the absolute price move up and down 

[00:50:36] - Is there a pricing genius we should take note of?

[00:53:18] - The single question every leader should ask themselves

[00:53:46] - The kindest thing anyone has ever done for him

My guest today is Scott Wilson. Scott is the CIO of Washington University’s endowment, which manages over $13 billion. In this conversation we discuss WashU’s non-traditional endowment model and cover a variety of asset classes and geographies. We talk about the qualities Scott looks for in managers, lessons from investing in Asia and emerging markets, and red flags in the venture space. Please enjoy this conversation with Scott Wilson.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern Saas platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:38] - [First question] - What he learned about markets from quant fixed income trading 

[00:04:42] - How his experience shaped his degree of skepticism of the world

[00:05:15] - The story that brought him to Grinnell College 

[00:06:45] - What his education was like back in 2010 and what seemed sensible and insane when he arrived

[00:09:37] - His philosophy around trying to have more direct ownership

[00:12:03] - Lessons learned about choosing good partners and doing it effectively over time

[00:13:51] - Things that are most enjoyable about getting to know new managers 

[00:16:17] - Why they spend so much time in frontier and emerging markets

[00:18:21] - Lessons learned from investing in China and thoughts on it today 

[00:23:16] - The worst things he sees from venture investors 

[00:24:39] - Whether or not venture investors should care more 

[00:27:55] - What percentage of investors in private equity are investors versus just involved to try and engineer returns

[00:28:59] - His impressions on hedge funds and the evolution of the hedge fund model

[00:31:18] - The role that credit can play in a portfolio like the one he manages now 

[00:36:34] - Everything he’s learned about asset managers acting as asset gatherers

[00:39:35] - Ways he fights convergence and tracking error overseeing so much capital 

[00:41:49] - What it’s like to go through the bad side of tracking error

[00:45:43] - What he sees as a normal level of tracking error for endowments and foundations

[00:46:59] - Why such big pools of institutional capital tend to look so similar 

[00:48:10] - Whether or not real estate sits somewhere between stocks and bonds

[00:51:10] - Colliding managers in a fun and spirited way at meetings 

[00:52:16] - An investing trip from his career that he finds most memorable

[00:52:50] - The kindest thing anyone has ever done for him

My guests today are Julio Vasconcellos and Mate Pencz, who are partners at Canary and Atlantico, leading early-stage investment firms in Latin America. They’re also both successful entrepreneurs. Mate is the co-founder and CEO of Brazilian real estate unicorn, Loft. Julio was Facebook’s first country lead for Brazil, an entrepreneur in residence at Benchmark, and the former founder of Peixe Urbano which sold to Baidu. This conversation was a great opportunity to dive into the state of investing and business in Latin America today, what it looks like on the ground, and cover the most interesting findings from Atlantico's annual report on Digital Transformation in the region. Please enjoy my conversation with Julio and Mate.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:39] - [First question] - A broad perspective on what is interesting in Latin American investing today - Latin America Digital Report 2022

[00:05:15] - What makes up the existing 1.5% tech penetration index in Lat Am

[00:06:11] - Florian Hagenbuch, Mate Pencz - Everything Will be Bought Online (Loft); David Velez - Building the Branchless Network (Nubank); How important it is to parse by country when it comes to building businesses in LatAm 

[00:08:31] - Overview of LatAm as a microcosm of fintech innovation happening really fast and what is most exciting in that sphere 

[00:12:28] - Why the adoption of PIX was so successful and how it maps onto the banking system

[00:14:27] - What PIX’s widespread adoption will enable for the coming wave of entrepreneurs 

[00:22:30] - Shifting to remote work and how it’ll affect LatAm workers and talent

[00:30:06] - What it feels like for an entrepreneur today compared to when Loft launched 

[00:32:36] - Deeper themes and what needs to be unlocked for LatAm’s tech sector to look more like the US or China with big tech giants 

[00:40:12] - Sources of available funding for venture and private equity  

[00:42:54] - What valuations look like and whether or not there’s an entry multiple discount

[00:45:12] - Seeking evidence that crypto is used in more valuable ways in emerging markets 

[00:48:00] - Areas where LatAm is operating in a future state more so than elsewhere

[00:50:28] - What the right amount of global firm participation in capital partnerships looks like

[00:52:38] - Big standout lessons from their operating days 

[00:55:53] - What is most exciting and concerning about their investing style and investing writ large in LatAm 

[00:58:51] - The kindest thing anyone has ever done for Julio

My guest today is Trina Spear, a former investor at Blackstone and the co-founder and CEO of FIGS. FIGS is a multi-billion-dollar public company that built a category-leading brand selling scrubs to healthcare professionals. It was a problem hiding in plain sight and FIGS solved it through vertical integration and customer obsession. Trina shares so many interesting, simple lessons that are often ignored in business. Please enjoy my great conversation with Trina Spear.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:28] - [First question] - The original insight that lead to founding FIGS

[00:04:28] - Why obvious opportunities can go so long before being seized 

[00:06:23] - Key dimensions needed to improve the product and the early days 

[00:09:02] - Basic overview of a clothing retailer’s financial profile

[00:10:49] - Financing the business and the early stage cash flow cycle 

[00:13:04] - Strategies to manage workflow and making sacrifices

[00:14:43] - Advice for people trying to build their brands in a hands-on way 

[00:17:14] - The biggest calculated risk she took in the first five years

[00:19:00] - Building a foundation that allowed for such explosive growth

[00:21:44] - The story that allowed FIGS to connect with their customers

[00:24:43] - Painting a picture of the size and scope of healthcare apparel

[00:26:22] - Things lazy companies do and thoughts on product variety

[00:28:54] - Defining SKU productivity and what to do with low productivity products 

[00:30:21] - Chip Wilson Book; Lessons learned from reading Chip’s story

[00:31:58] - Balancing a healthy relationship with your CFO

[00:33:59] - Where she sees the most runway to tackle and continue to execute

[00:35:46] - A women-lead industry and her time spent with Meg Whitman

[00:38:13] - The most essential jobs she feels she has and shouldn’t do as the CEO

[00:40:03] - Thoughts about relationships with investors and messaging 

[00:42:14] - What she’d be most focus on in founders if she was just an investor 

[00:43:57] - The most stressful thing that has ever come across her desk 

[00:44:41] - What types of things bring her the most joy in building FIGS

[00:45:27] - Philosophy of hiring given their small team and when it’s okay to hire

[00:46:56] - Whether or not there’s a role for non A players in businesses

[00:47:48] - The kindest thing anyone has ever done for her

Today, we are sharing an episode of Web3 Breakdowns with you. My Invest Like the Best conversation with Gabe Leydon last year was one of my favorites and became one of our most popular. Since that conversation, Gabe has become one of the most interesting builders in web3 that I know so I was excited to have him back to share his views of the space and how it might grow. If you enjoy this episode, subscribe to Web3 Breakdowns on your preferred podcast player.

My guest today is Gabe Leydon, who’s episode last year was one of our most popular ever. Gabe has spent the last 20 years designing video games and is one of the most original thinkers I know. He was the co-founder of Machine Zone, which pioneered free-to-play hits like Mobile Strike and Game of War. Over the past year, he has been in stealth mode building a web2 meets web3 video game company called Limit Break, which is founded on a brand new business model that he calls free-to-own. We dive into his vision for the future of gaming, how it could onboard a billion users onto the Ethereum network, and why the LTVs of crypto gamers are so far higher than their web2 counterparts. Please enjoy this conversation with Gabe Leydon.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Coinbase Prime. Coinbase Prime combines advanced trading, battle-tested custody, financing, and prime services in a single solution. Clients have used our comprehensive investing platform to execute some of the largest trades in the industry because they are the only publicly-traded company with experience trading and custodying crypto assets at scale. Get started with Coinbase Prime today at coinbase.com/prime.

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Web3 Breakdowns is a property of Colossus, LLC. For more episodes of Web3 Breakdowns, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @Web3Breakdowns | @ericgoldenx | @patrick_oshag 

Show Notes

[00:02:19] - [First question] - What free-to-own gaming means and why it’s exciting 

[00:11:40] - Pre-existing behavior that sets up free-to-own for success

[00:12:32] - The progression from PFP NFTs to clubs and the road ahead

[00:14:16] - Overview of the business and monetization model for free-to-own games

[00:17:51] - The story of DigiDaigaku, their mechanics, the drops, and what lead to their creation

[00:22:14] - Balancing supply and demand in a free-to-own market

[00:24:35] - Creativity and extensions of the DigiDaigaku NFTs

[00:26:13] - Tiering, breeding and the role the Genesis series will play in the Digi universe

[00:27:32] - The level of brand marketing NFTs will unlock for businesses

[00:29:57] - How free-to-own will be the primary monetization method for brands

[00:31:21] - A future with a global marketing shift towards digital property and economies

[00:33:06] - Why most of the winning PFP projects are of unique characters

[00:35:50] - His Twitter strategy and how he’s created such a fervor around him

[00:42:40] - What will define the legendary marketers over the coming decade 

[00:43:06] - Interoperability needed to make real-world NFT uses appealing to consumers 

[00:44:44] - Whether or not we’ll see more token-gated business in the future 

[00:45:40] - Stable Diffusion and his impression of the new AI art generating bots

[00:48:56] - What great distribution looks like in a digitally native world

[00:50:03] - The emphasis of innovation taking place in the metaverse being a bad thing

[00:53:24] - Things he most admires in adjacent games and creators in his world

[00:54:25] - Unique game mechanics that Web3 technology unlocks 

[00:56:16] - NFTs will be the gateway for people to acquire crypto

My guest today is Harley Finkelstein. Harley is the President of Shopify and has been with the company since its early years. He is a lawyer by training but an entrepreneur by calling and that is the focus of our discussion. We discuss the different dimensions of entrepreneurship and Shopify’s role in promoting it, as well as exploring the company’s transition to public markets, and what the last few years have been like. Please enjoy my discussion with Harley Finkelstein. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:26] - [First question] - His interpretation and definition of a person’s life's work 

[00:05:50] - The story of the riverstone and the average polished executive 

[00:08:36] - The thing he can’t help but do; and focusing on our compulsions

[00:13:12] - How he would boil things down to the most simple entrepreneurial formula; Distilled

[00:16:38] - What is harder and easier about new business formation today 

[00:21:03] - The countervailing forces for small-to-medium business entrepreneurship 

[00:24:31] - What he’s learned about operationalizing ideas and mentor lessons

[00:29:08] - A piece of fortune cookie advice that he finds terrible

[00:30:49] - How Brands Grow; his philosophy on marketing & distribution  

[00:35:27] - The most effective distribution strategies he’s seen work in Shopify that might be portable to other businesses

[00:38:43] - What it was like getting their first app developer for the Shopify app store

[00:41:17] - The state of ecommerce today writ large and what trends are interesting 

[00:45:46] - Lessons learned about the digital places that people are buying 

[00:49:06] - What it’s been like as an executive working at a company that had their stock price explode over the pandemic 

[00:52:25] - Tips for communicating effectively with Wall Street

[00:54:14] - An investor that stands out in memory that really impressed him

[00:55:10] - Important aspects of his world that are worth mentioning 

[00:57:04] - Lessons learned about motivating people through DJing 

[00:59:12] - Whether or not reading the crowd can apply to business

[01:03:49] - The kindest thing anyone has ever done for him

My guest today is Mitch Lasky. Mitch is a partner at Benchmark and one of the leading figures in the video game industry. Over the last 30 years, he has built, led, and invested in a number of the best gaming companies in the world, including Activision, EA, Riot, Snapchat, and Discord. I couldn’t think of a better person to break down the anatomy of great gaming businesses and Mitch does not disappoint. His insights are remarkable. Please enjoy this excellent conversation with Mitch Lasky.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:31] - [First question] - Why there aren’t more famous gaming investors

[00:05:08] - The most important features of the modern gaming business model

[00:07:11] - Developing his aesthetic taste and investing decision skill

[00:08:03] - What makes a game fun 

[00:09:26] - How delivering a pleasurable active user experience differs from passive content and media

[00:11:09] - The developers of Doom being the first real modern video game company

[00:13:09] - Half-Life’s important role in the development of the gaming industry

[00:17:54] - How some of the big game aggregators get started in the first place

[00:19:58] - What Riot can teach non-gaming businesses about business writ large

[00:21:10] - Ways that the change from physical games to downloads changed monetization

[00:31:47] - The impact of Apple’s privacy changes on gaming revenue

[00:34:11] - How the access to professional game engines and a lower friction environment will change the industry

[00:37:04] - Whether or not there is a step beyond mobile

[00:39:42] - Ways platforms like Twitch and Discord have influenced gaming

[00:42:26] - What he’s learned about games that allow them to seemingly exist forever

[00:45:17] - Signs of a healthy gaming community

[00:46:21] - The role of celebrities and influencers and generating retained audiences

[00:47:45] - Whether or not crypto will unlock new opportunities for in-game monetization 

[00:52:50] - Key categories of motivators that could replace a ponzi-style in-game inflation 

[00:54:36] - Contrasting League of Legends versus a Ready Player One style world

[00:58:22] - Emerging technologies and trends that may revolutionize the industry 

[01:02:41] - The most genius game pattern he’s ever played

[01:04:44] - What attributes will define the great game investors in the coming decades

[01:06:59] - How much his experience lends itself to investing in other sectors

[01:11:07] - The kindest thing anyone has ever done for him

My guest today is David Senra. David has studied history’s great founders and entrepreneurs in more depth than anyone I’ve ever met, and I’d wager more than anyone else alive. In this conversation, we cover many of the most common themes he’s discovered studying hundreds of entrepreneurs like Estée Lauder, John Rockefeller, Enzo Ferrari, and Edwin Land. I found this to be one of the most energizing conversations I’ve had in a long time, and one I’ll return to often.

David’s work and extraordinary energy aligns so well with our mission at Colossus that we’re excited to partner with him. You’ll soon be able to find his podcasts and transcripts at joincolossus.com where we hope you’ll learn as much from him as we have. If you like this conversation, be sure to subscribe to David’s podcast called Founders. Now onto our discussion. Please enjoy this great conversation with David Senra.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:01] - [First question] - When he first fell in love with reading

[00:07:01] - What’s rooted in his own history that’s made him obsessive about studying history’s great entrepreneurs and founders - Founders Podcast

[00:13:45] - How often obsession is apparent in the founders he’s studied across hundreds of biographies 

[00:18:08] - What is often behind obsession and how people listening can apply the lessons to their own lives

[00:22:45] - The dynamic and relationship between inspiration and perspiration 

[00:27:11] - Commonalities between the layers of leadership and support underneath founders

[00:31:52] - Where else he’s seen ego rear its head in good and bad ways 

[00:38:34] - How often do great founders break the law or enter gray areas of it 

[00:41:22] - The role constant learning and listening plays in success

[00:45:12] - Talking about how anything worth doing is worth doing to excess 

[00:52:18] - Describing the soul of founders and businesses

[00:58:39] - What he’s learned about all of these founders as it relates to marketing 

[01:08:10] - Who his idols are in podcasting specifically 

[01:14:55] - Major aspects of people he’s studied that haven’t been discussed yet

[01:19:55] - The kindest thing anyone has ever done for him

My guest today is Robert Smith, the founder, Chairman, and CEO of Vista Equity Partners. An engineer by training, Robert started Vista at the turn of the millennium and built it into one of the world's most successful software-focused investment firms. We discuss the white space left in enterprise software investing, the importance of capital cycles, and what he’s learned building an iconic investing franchise. Please enjoy my discussion with Robert Smith.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

-----

This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:34] - [First question] - What the enterprise software market looks and feels like to him

[00:05:52] - Whether or not software is becoming a saturated market and what will drive demand over the coming decades

[00:09:42] - Bringing an engineering mindset to enterprise software investing and culture

[00:12:36] - A single change he made to a business that stands out most in memory

[00:14:33] - Qualities that are most critical in defining a good enterprise software company

[00:18:07] - How the profile of companies he’s bought has changed over the years

[00:20:33] - Categories of software he tends to gravitate towards 

[00:23:56] - Evolving his model for considering what multiple to pay for a business and thinking about p/e growth multiples 

[00:27:17] - Lessons learned about customer churn over his twenty two year career

[00:29:44] - Capital cycles and how much they truly impact the software world 

[00:31:53] - What elements of building Vista have most appealed to him over the years  

[00:38:06] - The war for talent and what his senior team would debate most 

[00:40:01] - Biggest mistakes Vista has made and what they taught him

[00:41:09] - What has him most insecure or paranoid about the platform he’s built

[00:43:10] - The advice he’d give on having good relationships with LPs

[00:44:57] - The largest risk he or Vista has ever intentionally taken 

[00:46:15] - What he’s learned about having a winning negotiations and sales approach

[00:49:27] - Who he’d give all of his capital to outside of Vista

[00:53:08] - The work he does in the foster world

[00:54:49] - The kindest thing anyone has ever done for him

My guest today is Katherine Boyle, a general partner at Andreessen Horowitz. Katherine started her career as a reporter for The Washington Post before moving into VC at General Catalyst. She now leads a practice at a16z called American Dynamism, investing in companies that are solving critical issues in areas like defense, housing, and education.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

The content here is for informational purposes only and should not be taken as legal, business, tax or investment advice, or be used to evaluate any investment or security and is not directed at any investors or potential investors in any a16z fund. For more details, please see a16z.com/disclosures.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:42] - [First question] - The origin and overview of the term American Dynamism 

[00:05:01] - Why the shift to a move slow and make sure nothing breaks mentality

[00:07:31] - What about the American system today feels broken and stale 

[00:09:48] - Becoming a journalist at The Washington Post 

[00:11:35] - Describing the power landscape of media as it exists today  

[00:12:28] - Major categories of American Dynamism that matter most  

[00:14:29] - What matters more or less to her as an investor in these categories 

[00:17:31] - Whether or not there’s anything fundamentally broken about our government

[00:19:36] - The Systems Bible; What excites her about aerospace and defense and what creates opportunity and demand in these sectors

[00:26:01] - An overview of how lobbying works and who does it and why

[00:33:09] - The biggest problems that currently exist in the K-12 school system 

[00:37:34] - The role immigration will play in range of outcomes in these main categories 

[00:39:32] - Key takeaways about housing in light of American Dynamism  

[00:42:09] - Her interpretation of the chart that shows inflation in categories over time

[00:47:56] - Whether or not expected returns and risk profiles are different in this area 

[00:49:55] - Overview of the anatomy of a great story  

[00:51:30] - The story she tells founders at this stage so establish a partnership 

[00:52:46] - The kindest thing that anyone has ever done for her

My guest today is Ravi Gupta. Ravi spent a decade in private equity at KKR before joining Instacart as their first CFO and COO. He navigated them through a critical moment in their history and returned to investing in 2019 as a partner at Sequoia. Our discussion gets to the heart of what it means to build and invest in great businesses, and we talk a lot about the personal side of the journey, which tends to get overlooked. Please enjoy this great conversation with Ravi Gupta.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:34] - [First question] - Why it’s important to keep the main thing the main thing

[00:04:59] - His first exposure to this idea; How Will You Measure Your Life

[00:07:50] - Thoughts on the conflict of the main thing for a business and a person

[00:11:45] - The most painful episode of enacting this philosophy at Instacart 

[00:19:16] - Amazon’s 14 leadership principles vs. his concept of focus

[00:21:55] - What good main things share in common and their attributes; Frank Slootman Episode

[00:24:48] - Whether or not the feedback loop for things that work are very short 

[00:26:04] - The nature of joy and competitiveness in company culture 

[00:29:01] - How he assesses the depth that motivation runs through people and companies

[00:32:43] - Analysis of his own motivations in life 

[00:35:34] - Differences and shortcomings of virtuous and vicious motivators 

[00:37:15] - How to accurately figure out someones motivators in a short period of time

[00:40:22] - Being Demanding and Supportive; Why these words pair so well together

[00:45:55] - What he’s looking for in companies given all of the ideas discussed so far

[00:51:11] - How his ideology manifests inside of Sequoia 

[00:58:44] - What it’s like to mentor an apprentice and how to do it well

[01:02:40] - Adjusting behaviors to meet current markets where they’re at 

[01:06:13] - Defining what a great product is

[01:07:56] - What he did to turn around Instacart by narrowing their focus

[01:12:28] - The things that most drove the switchover at Instacart

[01:14:53] - The kindest thing anyone has ever done for him

My guest today is Will Thorndike. I first spoke to Will in 2017 about his excellent book The Outsiders and his career in private equity. I titled that conversation: How Skilled Capital Allocators Compound Capital. In many ways this conversation continues where that one left off. Through the lens of his new project, a podcast called 50X, we explore the power of multi-decade holding periods and the shared characteristics of businesses that are able to compound returns at high rates for abnormally long periods of time. Please enjoy this discussion with my friend, Will Thorndike, and if you haven’t subscribed to 50X, I highly recommend doing so.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:45] - [First question] - How working on The Outsiders project shaped his thinking

[00:06:29] - His interest in long-term holding periods and dealing with multi-decade time horizons

[00:09:42] - Shared characteristics among compounding machines

[00:11:23] - Defining capital efficiency and the return on tangible capital metric 

[00:13:02] - An example of an attractive business that requires a lot maintenance CapEx

[00:14:22] - Thoughts on the measurement of intangibles and whether or not he’d avoid great businesses that are intangible heavy 

[00:15:25] - Tangible ways capital efficiency rolls into compounding capacity 

[00:20:32] - Lessons learned about good game selection for companies 

[00:25:09] - An example of a decentralized structure and why it works so well

[00:30:00] - What the best serial acquirers do for long-term holders

[00:31:46] - Advantages of using debt for financing and acquisitions  

[00:33:39] - How different the future might be for young CEOs with capital allocator mindsets

[00:39:09] - 3 companies that Housatonic Partners has owned for more than 25 years

[00:40:29] - What made Karen Moriarty so good for so long 

[00:42:36] - The crossover between public and private investing and the virtues of each sector

[00:47:10] - What is at the top of his wish list of the companies he wants to explore 

[00:50:25] - The development of investor conviction over time and what he’s learned about it

[00:52:19] - Lessons learned about producing great media

[00:53:43] - What he can teach us about deep research on companies with analysts

[00:55:10] - Adjusting his thinking and investing in a high variance world

My guest today is Alok Vasudev. Alok is an early-stage investor who has been in the crypto space for a very long time. Before co-founding Standard Crypto, he was an investor at Benchmark and S28 Capital. Given Alok's experience and the prevailing mood right now in crypto, this is a particularly interesting discussion on the ecosystem writ large. We discuss whether the bubble can be thought of as productive speculation, his views on skeptics in the space, and look at some big, potentially, underestimated ideas. Please enjoy my conversation with Alok Vasudev.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:31] - [First question] - His history in venture and thoughts on the crypto ecosystem

[00:06:06] - What it means to be great at searching for white space as a venture capitalist

[00:08:00] - Things his original venture peers would say he was best and worst at

[00:09:24] - How he would address crypto skeptics broadly given today’s market

[00:13:35] - Whether or not it’s appropriate to look at each crypto token as a stock 

[00:15:32] - The pool of demand for Dai and the end use-case itself for the stablecoin 

[00:17:01] - What matters to him the most in the world of stablecoins 

[00:19:59] - Defining sound and unsound collateral 

[00:21:02] - Why the US doesn’t digitize the dollar and how being a government entity would impede some of their capabilities 

[00:23:21] - What a community operated computer unlocks compared to a standalone one

[00:27:09] - What persistence and resilience from community computers open up  

[00:29:30] - Something going on that people aren’t talking about yet in regards to blockchains

[00:33:54] - The notion of productive speculation and what it means 

[00:36:03] - One of the best historical examples of productive speculation

[00:42:29] - How things outside of the blockchain become integrated and connected to it

[00:45:43] - Ways crypto will impact the gaming world over the coming years

[00:49:10] - Handicapping a potential future where NFTs work and blockchains don’t benefit

[00:51:42] - Thoughts on the world of art, IP, NFTs, and its changing landscape

[00:54:43] - Whether or not there are companies being built that can streamline and facilitate this form of connection between artists and their fanbases

[00:58:13] - Other controversial opinions he holds in the crypto community 

[01:03:13] - What he’s most bullish and bearish on right now

[01:07:29] - The kindest thing anyone has ever done for him

My guest today is Matthew Ball. Matt is an investor, the former head of strategy at Amazon studios, and one of the brightest minds in the media industry. Through his essays and now his book, which launches today, Matt has established himself as the foremost authority on the Metaverse, which has stormed into the public eye since I first had him on the show two years ago. The Metaverse is the focus of our discussion and I hope you enjoy this encyclopedic tour through all of its details as much as I did.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

-----

Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:37] - [First question] - Which most represents the Metaverse: Minecraft, Ready Player One, Fortnite, or Facebook’s Horizon

[00:05:58] - Facebook trying to own the concept of the Metaverse by changing their name 

[00:09:22] - Defining what the Metaverse is and a good working definition of it

[00:11:33] - The state of the engines behind 3D output and the history of them 

[00:16:32] - The role IP played in bootstrapping the first Metaverses 

[00:18:32] - Where the ability to create digital environments will lead, and what Unreal 7 could look like compared to Unreal 5 today

[00:21:03] - Natural limits of the Metaverse compared to real-world experiences

[00:24:16] - Other sensory inputs that will need to be improved for digital immersion

[00:26:59] - Why the initial excitement of trying something like Oculus wears off over time, both for casual gamers and those excited about this new frontier

[00:31:40] - Changes in technology and new projects that have him most excited that will empower the digital infrastructure for Metaverses

[00:37:14] - What interoperability means and why it has its own chapter in his book

[00:31:52] - How Roblox connects with Fortnite and how far down we need to go to build a bridge between digital worlds

[00:46:13] - What will drive commerce in the Metaverse and the possibility for a singular currency standard

[00:51:35] - Considering the demand for the Metaverse and whether or not it will be a constraint on adoption and success

[00:57:37] - What the modern equivalent of a lemonade stand will be in the Metaverse

[00:59:58] - The lower adoption rates for more participatory media consumption[01:03:19] - Potential pitfalls and the dark side of the metaverse

[01:06:14] - Who the categorical winners of the Metaverse might be   

[01:14:15] - The top things he would suggest exploring to best understand the Metaverse

Today we are dropping a special episode in the Invest Like the Best feed. You will hear the first episode of 50X – a new series from Will Thorndike and the team at Compounding Labs, in partnership with Colossus. Will’s book, The Outsiders, is one of the best business and investing books you will find. Now you will hear him continuing his work in the hosting chair as he looks in detail at investments that have appreciated at least 50-fold.

First up is TransDigm, an aerospace components manufacturer that has returned over 1,750X since its inception nearly three decades earlier. In this episode, Will is joined by Nick Howley, TransDigm’s long-time CEO and Chairman. Make sure to subscribe to 50X in your preferred podcast player.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. The team at Tegus has built a full company intelligence platform aimed at streamlining the investment research process. In preparation for the 50X series, we actively used Tegus to gain qualitative insights beyond traditional reported data. To learn more and enjoy a free trial, visit tegus.co/50x. 

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50X is a podcast that dissects the anatomy of extraordinary long-term investments. The show is hosted by Will Thorndike and the team at Compounding Labs, and brought to you in partnership with Colossus.

In each episode of 50X, we look in detail at an investment that has appreciated at least 50-fold. From the seat of the professional investor and occasionally the CEO, we explore its origins, evolution, and eventual outcome, studying key themes around long-term value creation ranging from operations, capital allocation, and culture to pivotal buy and sell decisions. To enhance the quality and depth of our interviews, we rigorously study each asset in advance, diving into all available public and private resources.

Learn more and dive into our research at 50xpodcast.com

Follow us on Twitter: @50Xpodcast and @joincolossus

Show Notes

[00:00:00] – 50X Introduction 

[00:02:00] – Sponsorship: Tegus

[00:07:04] – Episode Introduction 

[00:09:05] – Nick’s Background pre-TransDigm

[00:11:56] – Original Acquisition from Imo Industries in 1993

[00:15:33] – Thesis and Performance under Kelso & Co.’s Ownership

[00:18:42] – Genesis of Three Key Value Drivers: Price, Productivity, and New Business

[00:21:07] – Building the Management Team

[00:24:05] – Early Lessons on Value Drivers

[00:27:53] – Capital Allocation under Kelso & Co.

[00:28:51] – Sale to Odyssey Investment Partners in 1998

[00:30:26] – Strategy under Odyssey’s Ownership

[00:31:51] – Early Acquisitions and Integration Playbook

[00:37:26] – Early External Crises

[00:41:13] – Snapshot at Conclusion of Odyssey’s Ownership in 2003

[00:43:19] – Building a Decentralized Culture  

[00:46:23] – Differentiated Approach to Compensation

[00:52:12] – Sale to Warburg Pincus in 2003

[00:55:51] – Shift to Inorganic Growth under Warburg’s Ownership

[00:58:08] – Evolution of M&A Process

[01:05:37] – Post-Acquisition Expectations and Post-Mortem Process

[01:09:48] – Divesting Acquired Assets to Maintain Focus

[01:11:29] – Embedding Value-Generative Culture via Hiring and Training

[01:13:54] – Quarterly Product Line Reviews

[01:20:43] – Recap of Private Investment Returns and Snapshot pre-IPO

My guest today is Alice Bentinck, co-founder of Entrepreneur First. Entrepreneur First, or EF, invests pre-company by systematizing the way that talented individuals find co-founders, develop ideas, and scale into companies. They’re an incubator of teams and ideas on a mission to create impactful companies that, without their help, wouldn’t exist. I first spoke with Alice’s co-founder, Matt Clifford, over two years ago and have been fascinated with EF’s model of investing ever since. Please enjoy my conversation with Alice Bentinck.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:33] - [First question] - Overview of what Entrepreneur First is today

[00:05:57] - How she identifies the people to bring into each cohort and convince them to quit their job to join EF for eight weeks

[00:10:10] - Categories of the main types of people who join the EF program

[00:12:32] - What she’s learned about negative screening at the first stage of recruits 

[00:14:07] - Positive signals she looks for in early admissions 

[00:17:46] - What the program itself feels like as a participant

[00:21:29] - Reasons partners tend to fail and whether or not EF advises equity splits between founders

[00:24:49] - How important the idea is that the team will be working on 

[00:28:04] - Exercises she enjoys doing with the new cohorts around social norms

[00:30:38] - How the experience looks physically in each city 

[00:32:57] - Categories of data collected as the cohorts unfold and making investment decisions

[00:36:46] - Ways the companies mature after EF and what kinds of investors fund the next stage of their startups

[00:40:55] - Why aren’t there ten EF style initiatives or organizations

[00:44:26] - Motivations for the change in their holding company structure

[00:46:48] - The love of product and ideas she’s playing with right now

[00:51:49] - Cities she has her eye on that EF is not a participant in today and criteria that makes a city desirable for EF

[00:54:03] - A piece of software that EF could benefit from that doesn’t exist yet

[00:55:30] - The keys to her harmonious relationship with her co-founder Matt 

[00:59:01] - National and international impediments that directly impact company building

[01:01:36] - The kindest thing anyone has ever done for her

My guest today is Jess Lee. Jess is a partner at Sequoia Capital as well as their Chief Product Officer. Before becoming an investor, Jess co-founded fashion app, Polyvore, and was an early product manager for Google Maps. Most recently, she founded All Raise, a non-profit that is changing the gender balance in tech. Our discussion ranges from Burning Man to Marvel to Sequoia’s mobile app and I hope that Jess’s passion for delighting users rubs off on you. Please enjoy my conversation with Jess Lee.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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Today's episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:35] - [First question] - Why more investment firms don’t have a product mindset

[00:05:22] - How to approach building a productized version of capital 

[00:08:00] - Ways Ampersand measures success and judging their own performance 

[00:08:49] - Driving reasons that Sequoia wins deals beyond their brand name

[00:10:28] - How her work as CPO at Sequoia has changed her investing approach

[00:12:28] - Everything she’s learned about community and its relevance to business 

[00:17:48] - What the gold standards are for studying strongly built communities 

[00:19:42] - What it is about Comic-Con that works so well from a community standard  

[00:21:18] - The role that scarcity plays in communities writ large

[00:23:10] - Product mindset and customer obsession 

[00:24:33] - Knowing when it’s okay to begin expanding 

[00:28:12] - Rates of change in her investment progress and dollars going to female founders

[00:29:36] - Systemic bias and what’s driving a lack of funds towards female founders 

[00:32:26] - How she applies community building lessons to All Raise

[00:33:20] - The internal learning culture in Sequoia that others could adopt and benefit from

[00:37:01] - Which Marvel superheroes her Sequoia partners would be  

[00:39:05] - Seeds of motivation for Arc and what it is

[00:44:31] - The best ways she’s seen companies manage and support human capital

[00:45:36] - Biggest mistakes made when managing human capital 

[00:46:42] - What working on Google Maps taught her about product development 

[00:48:42] - Someone she admires and has learned the most from in All Raise  

[00:50:02] - Measuring success at Sequoia over the next ten years  

[00:52:20] - The kindest thing anyone has ever done for her

[00:53:42] - What it was that made the people who believed in her take a chance on her 

[00:55:03] - Things in pop culture today that most has her attention

My guest today is Ken Stanley. Ken is a Professor in Computer Science and a pioneer in the field of neuroevolution. He is also the co-author of a book called, Why Greatness Cannot Be Planned, which details a provocative idea that setting big, audacious goals can reduce the odds of achieving something great. We discuss that revelation in detail and how to apply it in our day-to-day lives. Please enjoy this great discussion with Ken Stanley.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:36] - [First question] - The best way to change the world is to stop trying to change it

[00:06:26] - The kinds of goals his work addresses and the ones it doesn’t

[00:08:46] - Almost no prerequisite to any major invention was invented with that major invention in mind

[00:14:04] - Picbreeder

[00:17:21] - How looking for specific results often makes arriving at them a longer process

[00:24:00] - The importance of the individual in a web of invention and disruption

[00:28:30] - How generations progressed in Picbreeder when consensus mechanisms were inserted into the process 

[00:31:24] - Examples of stepping stones that were invented that became something even greater

[00:36:02] - What his research means for how we should conduct ourselves writ large

[00:44:17] - Thoughts on necessity being the mother of all invention

[00:50:08] - The ways that society is arranged is psychologically toxic

[00:55:14] - The role that constraints play in creative output and outcomes in general; Brett Victor - Inventing on Principle

[01:01:10] - What the constraints are that he sets for himself in AI development

[01:04:44] - To know what’s new you need to know what’s not new

[01:06:47] - The kindest thing anyone has ever done for him

[01:08:28] - How he would allocate resources to create more innovation in the world

My guest today is Lydia Jett, Managing Partner of SoftBank Investment Advisers. Lydia leads the team’s consumer, internet, and e-commerce investments and has worked with many of the most significant consumer platforms in the world, including as a board member of Coupang and Flipkart. We cover all aspects of e-commerce and explore Lydia’s evolution as an investor alongside Masa Son at SoftBank. Please enjoy my conversation with Lydia Jett. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:34] - [First question] - What curiosity thread she’s been pulling on thus far in her career

[00:05:17] - The biggest felt differences doing things one way for a decade and changing now

[00:07:08] - Learning about tailwinds and what the predominant ones are that exist today

[00:10:44] - Competitive frontiers that exist today in e-commerce

[00:12:14] - What drives companies that grow faster than their competitors

[00:13:15] - What areas the world’s most innovative e-commerce companies are focused on

[00:16:38] - Unique characteristics that they select for in ecommerce CEOs and founders

[00:19:03] - Upside down approaches to e-commerce that aren’t common in America yet

[00:23:05] - Lessons learned about business models that don’t work in e-commerce

[00:27:47] - What western investors should know about Coupang 

[00:30:12] - Everything she’s learned about vertical integration

[00:33:01] - Everything she’s learned and cares about in regards to margins

[00:37:17] - The most extreme version of efficiency gain she’s seen deployed

[00:41:27] - The role the size of assets plays at SoftBank

[00:47:42] - Focusing on efficiency and smart allocation first before trying to scale 

[00:50:33] - Companies as products that investors buy and defining what great looks like

[00:53:16] - The danger of premature optimization around a set of KPIs 

[00:55:46] - How important the specific founder is for their given e-commerce company

[00:58:18] - Why e-commerce companies tend to start from a worse place than offline ones

[00:59:45] - Ways that she’s changed from working alongside Masayoshi Son for a year

[01:03:31] - Who comes most to mind as a great investor    

[01:05:23] - The kindest thing that anyone has ever done for her

My guests today are Josh Wolfe and Chris Power. Josh will be a familiar voice to many of you and is the co-founder and General Partner of Lux Capital. Chris is the founder and CEO of advanced manufacturing start-up, Hadrian. Most of our discussion centers on the need to modernize the factories that supply our space and defense industries. But given the current market environment, we also talk about capital conditions and the responsibility to build products that really matter. Please enjoy this conversation with Josh Wolfe and Chris Power.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:40] - [First question] - An overview of the precision manufacturing industry writ large

[00:08:28] - Why the manufacturing sector has so many great investment opportunities

[00:12:58] - Anduril Breakdown; What Hadrian in its final form will unlock for manufacturing

[00:16:08] - What the demand side looks like for manufacturers in its current state today 

[00:18:29] - How the nature of demand will shift for this style of manufacturing in the future

[00:22:51] - Important rare earth materials, supply chain constraints, and the revival of commodities 

[00:27:55] - The key set of jobs being done by mom and pop shops that could be innovated on and done within a Hadrian factory 

[00:30:35] - What is going on inside of a Hadrian factory and how they will evolve over time 

[00:32:10] - Prosecuting diligence on someone's ability to execute on their behalf

[00:37:14] - The PhD arrogance trap and how a Hadrian machine will be better in five years from now

[00:48:08] - Breadth of ability versus focus and selling parts to buyers early on

[00:50:42] - Lessons learned and advice for understanding the focus problem 

[00:56:39] - Fat startup vs. lean startups and making the hardest irreversible decision during Hadrian’s early days

[00:58:31] - Enduring more schlep work than less being a good signal

[00:59:06] - Chris’ thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes

[01:03:36] - Josh’s thoughts on the future of Hadrian and defining the exciting and scary edges of the spectrum of outcomes

[01:07:22] - The kindest thing anyone has ever done for Chris

My guest today is Martin Casado. Martin is a general partner at Andreessen Horowitz where he focuses on digital infrastructure. Before joining a16z, Martin pioneered software-defined networking and co-founded Nicira, which was bought by VMware for $1.3 billion in 2012. Martin has studied, built, and invested in digital infrastructure his whole career and is the perfect person to discuss the most interesting aspects of the industry. Please enjoy this great conversation with Martin Casado.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus streamlines the investment research process so you can get up to speed and find answers to critical questions on companies faster and more efficiently. The Tegus platform surfaces the hard-to-get qualitative insights, gives instant access to critical public financial data through BamSEC, and helps you set up customized expert calls. It’s all done on a single, modern SaaS platform that offers 360-degree insight into any public or private company. As a listener, you can take Tegus for a free test drive by visiting tegus.co/patrick. And until 2023 every Tegus license comes with complimentary access to BamSec by Tegus.

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Today's episode is brought to you by Brex, the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:43] - [First question] - The state of the digital infrastructure industry today 

[00:04:02] - The major stages and eras of cloud technology 

[00:06:30] - Overview of Dropbox’s story and the two major trends at the time of its emergence

[00:10:12] - Lost margin and lost market cap from big users of the public cloud 

[00:12:14] - Whether or not there is a headwind coming for public cloud providers

[00:17:33] - How entrepreneurs might go after the biggest public cloud providers

[00:19:37] - His view on API first companies and granular monetizable units in growing markets

[00:23:20] - Developer facing tools and what works well when going to market 

[00:27:12] - The difference between a front-end and back-end developer and what is changing in their responsibilities 

[00:28:45] - What he looks for as an investor when he’s processing a new API first company

[00:30:31] - Common redflags and disqualifying observations for an API first company 

[00:36:35] - Frank Slootman Episode; Snowflake’s offering for their users, their explosive growth, and primitives in their sector

[00:39:06] - The history of digital security and potential opportunities as an investor

[00:40:19] - How digital infrastructure intersects with the real world and hardware world

[00:43:33] - How to screen out people for their potential to deliver transformative technology

[00:47:45] - Things he’s most intrigued about by cryptocurrencies as an infrastructure person

[00:52:49] - The kindest thing anyone has ever done for him

My guest today is Aswath Damodaran, a Professor of Finance at NYU’s Stern School of Business. Aswath is one of the clearest teachers of investing and finance in our industry and through his blog, books, and YouTube has open-sourced his wisdom for decades. This conversation is a masterclass of key investing concepts. We discuss inflation, narratives, disruption, the evolution of alpha and edge, and his thoughts on ESG. Please enjoy this great conversation with Aswath Damodaran.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:43] - [First question] - How he thinks about inflation as a now dominant force

[00:04:33] - Why inflation is so important across the spectrum

[00:09:02] - Big lessons from other periods of historically high inflation writ large

[00:10:45] - Reasons why equities as an asset class struggle in high inflation environments

[00:15:21] - The relationship betweens goods versus services in times of high inflation

[00:16:59] - Broader economic implications especially for income inequality

[00:19:03] - The Fed taking inflation seriously now when they didn’t and thoughts on the policy response to today’s situation

[00:21:05] - How smart companies are defensively adjusting to inflation

[00:27:46] - The importance of a capital allocation skill-set for executive team members

[00:29:32] - Further historic lessons and how he’s being defensive against inflation

[00:33:09] - Lessons learned about Amazon valuing them every year since their inception

[00:42:25] - Whenever he sees Thanos in the Avengers he thinks of Amazon

[00:44:51] - Thoughts on Facebook, Apple and Microsoft

[00:48:26] - The evolution of edge and the search for alpha

[00:54:37] - Whether or not there’s utility in studying other investors 

[00:57:16] - Skill versus luck and the most common valuation mistakes he’s made

[00:59:09] - Assuming long-term growth rates and changing company life cycles

[01:02:02] - Momentum and Value investing in today’s market

[01:07:24] - Differences between interest rates and discount rates in regards to inflation

[01:12:00] - How today’s market affects early stage equity investment

[01:14:36] - The growing popularity of ESG and his seemingly contrarian view on it

[01:24:03] - Nature of disruption as a force and companies that are protected from it

[01:28:24] - Assigning a disruption risk premium when valuing companies

[01:32:52] - What he makes of Elon Musk buying Twitter

[01:34:24] - Other major topics he has a divergent view on 

[01:38:37] - Narrative And Numbers; The kindest thing anyone has ever done for him

[01:38:55] - Teaching with a goal of changing mindsets 

Today, we are running a special episode of Business Breakdowns. With geopolitics playing an increasingly important role in society again, this episode with Anduril’s CEO offers an inside look at the state of the defense industry and how it is changing. If you enjoy this episode, subscribe to Business Breakdowns on your preferred podcast player, where you’ll find past episodes on Block, Goldman Sachs, AutoZone and many others.

Today, we are breaking down Anduril. Anduril builds high tech defense systems for the US Department of Defense and its allies. Crucially, it does so with speed that emanates from Silicon Valley. Founded in 2017 by Palmer Luckey, who previously built and sold Oculus to Facebook, Anduril has achieved the rare feat of challenging the established order in the defense industry.

To break down Anduril, I’m joined by the company’s CEO and co-founder, Brian Schimpf. We discuss the history of the defense industry, how Anduril’s business is counter positioned against the legacy cost-plus model, and what Brian has learned about selling to the DoD. Please enjoy this breakdown of Anduril.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Tegus. Tegus is the new digital hub for market intelligence. The Tegus platform empowers Investors and Corporate Development teams to invest smarter by pairing best-in-class technology with the highest quality user-generated content and data. Find out why a majority of the top firms are using Tegus on a daily basis. If you're ready to go deeper on any company and you appreciate the value of primary research, head to tegus.co/breakdowns for a free trial.

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This episode is brought to you by Daloopa. Daloopa streamlines a major pain point for investors. By capturing all of a company's KPIs and adjusted financials into their database - Daloopa makes it easy to quickly update your models for what matters. Daloopa uses AI to find every KPI disclosed - from charts, to text, and even from footnotes of investor presentations. Daloopa updates these KPIs and data points in your existing Excel models in one click, regardless of your source or format. Test Daloopa for free at daloopa.com/Patrick.

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Business Breakdowns is a property of Colossus, LLC. For more episodes of Business Breakdowns, visit joincolossus.com/episodes.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @JoinColossus | @patrick_oshag | @jspujji | @zbfuss

Show Notes

[00:02:52] - [First question] - The history of defense technology and the technological and competitive landscape when he set out to build Anduril

[00:08:22] - What the early experience was like when approaching the government and finding an early adopter

[00:12:44] - Necessity being the mother of invention when it came to developing drones

[00:16:37] - What it’s like to develop hardware and software products at the same time 

[00:24:44] - The state of military technology and military conflict today writ large

[00:31:10] - Are we heading to a future where warfare is mostly machine against machine? 

[00:33:34] - Comparing the ghost drone system to predator drones

[00:38:40] - Guiding principles as a firm and deciding on their product roadmap

[00:43:25] - An overview of their product lineup and what they’ve built so far 

[00:51:56] - Most difficult decisions he’s had to make through Anduril’s history 

[00:53:51] - How he overcame Anduril’s lowest points and biggest challenges 

[00:58:38] - Thoughts on effectively compounding hardware innovation 

[01:02:23] - A moment he’s most proud of and regrets most in Anduril’s history

[01:04:20] - Lessons learned from observing Palantir and SpaceX 

[01:08:37] - The kindest thing anyone has ever done for him

My guest today is Tobi Lütke, co-founder and CEO of Shopify. Having first spoken to Tobi at the beginning of the pandemic, just two months into it, this felt an opportune moment to revisit Shopify and the world through Tobi’s eyes. Among many things, we discuss Shopify’s evolution into the world of atoms-based building through Shopify’s fulfillment network, the value of infrastructure writ large, and the impact of market volatility on day-to-day business building. Please enjoy my conversation with Tobi Lütke.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

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Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:44] - [First question] - His interest in infrastructure as a whole and why it’s underrated

[00:07:18] - Whether or not we’re currently building enough digital infrastructure 

[00:09:45] - Base level principles for decision making around building infrastructure 

[00:13:17] - How much room is left for innovation and whether or not we’ll just reinvent basic human instincts

[00:15:22] - Ways new ideas are fed into a product funnel at Shopify and greenlit

[00:19:34] - Solving eCommerce infrastructure and what he attributes to Shopify’s success

[00:24:23] - Overview of the Shopify Network and how it’s evolved over time 

[00:31:04] - Lessons learned in an atom-driven world in regards to fulfillment and logistics

[00:34:37] - Common ways bits thinkers are often wrong when solving atom problems

[00:35:50] - Spreadsheets tend to win meetings and how the ROI on a fulfillment network impacts its ecosystem

[00:40:26] - Navigating becoming an aggregator that sits on top of their merchants and whether or not there are plans to participate as a distributor

[00:45:45] - Fair market value, what it’s been like managing through such a volatile market, and important takeaways

[00:50:54] - Thoughts on capital allocation decisions as Shopify continues to grow

[00:53:25] - Advice for company leaders effectively communicating with their teams about stock-based compensation 

[00:59:04] - How much COVID altered their trajectory and what he’s most interested in as he looks out to the future

[01:03:45] - What he’s learned about blockchains and the crypto space given recent events

[01:08:45] - A new idea he’s encountered recently that he’s fallen in love with 

My guests today are Tyler Cowen and Daniel Gross. Tyler is an economics professor and creator of one of the most popular economics blogs on the internet. Daniel is the founder of start-up accelerator Pioneer, having previously been a director at Apple and a partner at Y Combinator. Both Daniel and Tyler are prolific talent spotters and that is the focus of our discussion and their new book, which is called Talent. Please enjoy this conversation with Tyler Cowen and Daniel Gross.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Brex. Brex is the integrated financial platform trusted by the world's most innovative entrepreneurs and fastest-growing companies. With Brex, you can move money fast for instant impact with high-limit corporate cards, payments, venture debt, and spend management software all in one place. Ready to accelerate your business? Learn more at brex.com/best.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:38] - [First question] - Defining what talent is to them writ large

[00:03:34] - The differences between means and ends in regards to talent

[00:04:14] - What the Diet Coke idea is and why it’s relevant

[00:06:32] - Types of energy that are valuable and the subtle differences between them 

[00:07:40] - Thoughts on using a moneyball-like approach to acquiring and evaluating talent 

[00:11:49] - The talent market and thinking about pricing talent specifically

[00:13:14] - What is seemingly overpriced in today’s talent landscape

[00:15:50] - Relationship between experience and/or age when it comes to talent

[00:20:34] - Lessons about the utility of intelligence and where they’ve lead them wrong

[00:23:35] - What’s beneath being an outsider and why it’s important

[00:24:46] - Why what people do in their downtime is worth considering  

[00:31:41] - Things to try and get out of a reference call as an objective

[00:32:40] - Disabilities and what lead them write that chapter specifically

[00:35:01] - Whether or not talented people are happier  

[00:38:40] - Lack of contentment and it’s dynamic influence over individuals

[00:41:01] - Where they think the other is most talented

[00:43:33] - Thinking about the physical side of mental performance

[00:45:49] - What was frustrating about writing the book

[00:48:25] - How they evaluate talent most differently now after having finished the book

[00:50:41] - What makes for a good bat signal and how to cast one well 

[00:53:27] - Personality inventories and what they would and wouldn’t recommend  

[00:54:15] - Geographical frictions and their role in high success rates

[00:56:08] - Antonio Gracias; Existing supply constraints on talent development

[01:00:01] - How they would redesign the current attractors of talent that we rely on today

[01:01:18] - Assembly line development and how we can improve and scale talent filters

[01:02:29] - The biggest open questions for talent today writ large

[01:05:16] - The kindest thing anyone has ever done for Tyler

My guest today is Jeff Jordan, General Partner at Andreessen Horowitz. Jeff has one of the most interesting set of experiences of guests that I’ve had on the show. As an operator, he has been the General Manager of eBay.com, President of PayPal, and CEO of OpenTable. As an investor, he was one of the first General Partners at a16z and sits on the board of Airbnb, Instacart, Pinterest, and other notable firms. Given his vast experience, he is the firm’s go-to-expert on all things marketplaces, which is the common thread in our conversation. Please enjoy this great discussion with Jeff Jordan.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:48] - The notion of perfect competition in marketplaces

[00:04:31] - How to build a marketplace while thinking about perfect competition

[00:05:32] - Promoting price discovery at eBay

[00:06:52] - Features of a marketplace he focuses on 

[00:08:38] - Best way to do lead generation 

[00:10:20] - Red flags for marketplace businesses 

[00:11:00] - Major business lessons learned while at Disney 

[00:12:10] - Learning to be an operator while at eBay; Leaving It All on the Field

[00:14:45] - How he got hired at OpenTable

[00:16:22] - Taking OpenTable public and being its first public company CEO

[00:17:44] - What they did well in financing OpenTable

[00:18:54] - Communications between company leaders and its investors 

[00:19:45] - Going from operator to investor

[00:22:08] - Lessons from the early years of becoming an investor and pricing companies

[00:24:12] - Power of network effects on a startup

[00:26:56] - Healthy tensions inside of a network

[00:29:23] - When the supply side is the more difficult part of the equation

[00:33:30] - The importance of being a perpetual learner as a founder

[00:35:36] - When he starts focusing on unit economics and margin profile in a new marketplace

[00:37:45] - Increasing convenience for a buyer as a business strategy 

[00:42:14] - Categories that could use better marketplace solutions

[00:44:36] - Layers of growth inside a business

[00:50:26] - Lessons with the unique business model of Pinterest

[00:52:03] - Unique aspects of the Andreessen Horowitz business model

[00:55:54] - Finding and recruiting talented general partner investors 

[00:57:37] - The morning basketball game and community strengthening

[01:01:36] - Defining great mentor relationships

[01:04:54] - Kindest thing anyone has done for him

[01:06:05] - Lessons from his parents

My guest today is Eric Glyman, co-founder and CEO of Ramp. Ramp is best known for its corporate cards but it has a range of software products to help finance teams save money and time. Since its founding in 2019, the business has grown rapidly and was last valued at $8 billion. Eric and I discuss Ramp’s initial marketing wedge, how the business has dealt with such fast growth, and why they hold stablecoins on their balance sheet. Please enjoy my conversation with Eric Glyman.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects - and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:41] - [First question] - What was most notably awry about the industry before Ramp

[00:04:45] - Breakdown of Visa; The business model of the Black Card compared to the business card offering of Ramp

[00:08:40] - Causes and what he attributes their early success to

[00:11:30] - Description of Ramp’s software in the beginning and the evolution of co-building it

[00:16:34] - How he’s gone about building the company and team fast enough to handle their explosive growth curve

[00:19:47] - Approaching all aspects of recruiting and acquiring such great talent

[00:21:39] - Thoughts on the biggest mistake he’s made while building Ramp

[00:24:05] - Lessons learned about marketing that this journey has taught him

[00:26:13] - Learning to manage a senior team and advice for managing rapid growth

[00:28:58] - Unique aspects of Ramp’s approach to the financing side 

[00:32:56] - Why they are storing some of their balance sheet in stablecoins 

[00:34:47] - What the idealized end state of Ramp looks like

[00:37:26] - How the data and information he sees indicates trends in the economy writ large

[00:39:33] - Providing secondary liquidity to employees in a world where companies stay private for longer periods of time

[00:43:03] - Aspects of company building that are still unnecessarily hard

[00:44:55] - What has him most excited about Ramp in the next 12-18 months

[00:46:42] - The kindest thing anyone has ever done for him

My guest today is Dmitry Balyasny. Dmitry is the Managing Partner and CIO of Balyasny Asset Management, otherwise known as BAM. BAM runs a multi-strategy, multi-PM model that aims to produce consistent absolute returns. Since its founding in 2001, it has produced only one negative year and become one of the largest firms of its kind. Please enjoy my conversation with Dmitry Balyasny. 

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick. 

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:53] - [First question] - The origin story of his firm and the key stages of evolution

[00:06:43] - Describing the difference between good and great in platform hedge funds 

[00:10:25] - How a multi-strategy, multi-investor group works and managing capital allocation

[00:13:58] - What he’s trying to solve at the end of the day as their CIO

[00:16:21] - How close they are to their idealized end-state 

[00:18:26] - Typical amounts of leverage associated with these types of models

[00:20:22] - Lessons learned about incentivizing talented investors

[00:22:39] - Ways he tends to attract risk takers and their levels of variance

[00:28:15] - Other characteristics that are common amongst great PMs

[00:30:42] - The nature and source of edge and how it’s changed most over time

[00:33:19] - Some of the hardest portfolio and business decisions he’s had to make 

[00:37:59] - One of his most important business decisions on the firm side

[00:40:09] - How they’ve thought about shorting as a firm in general and more recently

[00:43:52] - How interest rates affect this style of investing

[00:45:29] - His view on the opportunity set in private markets and what does and doesn’t excite him about it

[00:49:42] - How reading Ayn Rand most shaped his thinking

[00:50:36] - Things Ayn most got right and most got wrong in his mind

[00:51:24] - What the war in Ukraine has felt like for him as a Ukrainian-American

[00:52:08] - Ways the future still has him excited as he continues to build his firm

[00:53:53] - Where his trading instincts draw him today and areas of interest

[00:55:11] - His most memorable trade of all time

[00:56:37] - In which order the major asset classes will be affected by digital innovation

[00:58:13] - The kindest thing anyone has ever done for him

My guest today is Henry Ward, co-founder and CEO of Carta. Started in 2012, Carta helps companies and investors manage their cap tables, equity plans, and ownership. Last year, they launched CartaX, a platform for private companies and their employees to access secondary market liquidity. Our discussion is a detailed exploration of private market infrastructure and Henry’s views on building an enduring business. Please enjoy my conversation with Henry Ward.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

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This episode is brought to you by Vanta. Vanta has built software that makes it easier to get and maintain your SOC 2, HIPAA or ISO 27001 reports at a fraction of the typical cost. Listeners can redeem a $1k off coupon at vanta.com/patrick. 

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:02:57] - [First question] - The first key mental moment of how Carta came to him

[00:05:30] - Initial thoughts on how to position Carta as a business model

[00:06:47] - Historical divergence between private and public market infrastructure

[00:08:33] - What a price discovery process for primary shares could look like in the future

[00:11:09] - The end state Carta is trying to effect in their perfect state

[00:13:29] - Why it’s so hard for private company staff to manage their illiquid wealth

[00:15:45] - Lessons and challenges in the new market creation business

[00:17:57] - The nature and dynamics of supply and demand in this space

[00:22:45] - How Carta is mapped onto the success of its customers

[00:25:27] - Deciding on what is a good idea and what isn’t when it comes to focus

[00:28:07] - Describing the One of N versus N of One market frameworks and principles of this philosophy that manifests in how he runs Carta

[00:32:11] - How working at Carta would differ from a payroll-type company

[00:35:37] - Characterizing his leadership and management styles

[00:37:57] - The types of circumstances that bring out his tough side

[00:39:33] - Making hard decisions in a bottom up management model 

[00:44:05] - How he spends his time while building Carta

[00:45:02] - What a great product looks like to him

[00:47:10] - The Systems Bible; Defining what a great team looks like

[00:49:13] - What he’s learned about being great at Go-To-Market

[00:51:26] - Effective ways to beat competitors and build relationship pipelines

[00:53:49] - Things he likes the least about leading a company of this size 

[00:55:13] - What he fears most as he thinks about the future of Carta

[00:55:45] - Advice for entrepreneurs when thinking about data in modern businesses

[00:58:26] - The biggest missing pieces in capital market structure writ large

[01:00:17] - What’s next for CartaX and what he’ll be pushing to make it work 

[01:02:10] - Lessons learned from serving venture investors 

[01:04:25] - Whether or not investment banks are their competitors

[01:05:18] - Public market dislocation and how long it will last

[01:06:58] - The kindest thing anyone has ever done for him

My guest today is Alexandr Wang, the CEO and founder of Scale AI. Alexandr founded Scale in 2016, having been inspired to accelerate the development of AI through his work at Quora and his studies at MIT. Specifically, Alexandr realized there was a lack of infrastructure solutions for producing high quality data, the lifeblood for AI models. Today, Scale provides data solutions to leading AI teams at Meta, Microsoft, OpenAI, Flexport, the US Air Force, and many others. This time last year, the business was valued at over $7 billion. 

Our conversation is a primer on AI. We discuss the building blocks beneath successful artificial intelligence, AI’s role in both the public and private sector, and why data is the new code. We also cover the similarities and differences between AI and software from an investing perspective and what inspiration Scale takes from AWS. Please enjoy my great discussion with Alexandr Wang.

For the full show notes, transcript, and links to mentioned content, check out the episode page here.

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This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you're a professional equity investor and haven't talked to Canalyst recently, you should give them a shout. Learn more and try Canalyst for yourself at canalyst.com/Patrick. 

-----

This episode is brought to you by Lemon.io. The team at Lemon.io has built a network of Eastern European developers ready to pair with fast-growing startups. We have faced challenges hiring engineering talent for various projects and Lemon.io offered developers for one-off projects, developers for full start to finish product development, or developers that could be add-ons to the existing team. Check out lemon.io/patrick to learn more.

-----

Invest Like the Best is a property of Colossus, LLC. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. 

Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more.

Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here.

Follow us on Twitter: @patrick_oshag | @JoinColossus

Show Notes

[00:03:04] - [First question] - The role that AI and data play in geopolitics and foreign policy

[00:07:21] - The end state of a digital arms race akin to nuclear weapons

[00:08:53] - Current state of things writ large and how the public and private sectors differ

[00:11:33] - The flow and importance of talent when scaling AI and whether it’s more important than software 

[00:14:29] - His thoughts on how to communicate categories of what AI can do well and what is still a ways out

[00:20:18] - The process of creating an AI model and the stages of development

[00:27:16] - Principles of building a great engine for gathering data

[00:29:04] - The state of technology around annotating data writ large

[00:31:31] - What Scale does as a business and their product lineup

[00:35:08] - The Storage and Compute equivalents in the AI space

[00:37:08] - How Scale fills the gap in producing better and cleaner data

[00:39:52] - What Scale will look like in 10 years if their vision is fully realized

[00:41:11] - Where AI is in the S curve of acceleration and where AI and software intersect

[00:44:32] - Questions to ask about how to incorporate AI and data sets in your business

[00:46:23] - What worries him about the proliferation of technology that makes AI more accessible to the masses

[00:48:27] - The most interesting AI model he’s ever come across and collapsing the friction between human intent and programmable outcomes

[00:51:51] - The kindest thing anyone has ever done for him