E345: How I Raised $10 Billion in Venture Capital w/Scott Painter

What does it take to raise $270 million in a risk-off market while keeping your personal life, sanity, and team intact? In this episode, I sit down with Scott Painter, Founder & CEO, TrueCar, to unpack the 21-month journey of taking a company private. Scott shares how persistence, strategic thinking, and mental resilience allowed him to navigate investor skepticism, market volatility, and personal stakes. He discusses the lessons he learned from fundraising in both up and down markets, why creating momentum and scarcity is critical, and how setting boundaries transformed the outcome for him and his team. Highlights:

• The most difficult capital raise of Scott’s career and how he overcame repeated setbacks
• Persistence as a strategic tool: staying the course through 21 months of volatility
• Managing personal and professional stakes: balancing debt, family, and team morale
• Compartmentalizing bad news to make clear-headed decisions under pressure
• Using scarcity and deadlines to drive investor action in risk-off environments
• Learning from elite entrepreneurs like Elon Musk and applying resilience in real time
• Turning adversity into anti-fragility: lessons on confidence, focus, and long-term success

Guest bio:

Scott Painter is a serial entrepreneur and long-time leader in automotive technology, widely recognized for shaping how consumers buy, finance, and access vehicles. He founded TrueCar in 2005 to help car buyers save time and money with technology. Under his leadership, TrueCar went public in 2014. In January 2026, Painter re-acquired the company and returned as CEO to continue advancing its original mission.

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Sponsor:

AlphaSense is the AI-powered market intelligence platform trusted by 85% of the S&P 100, helping investment professionals make faster, more confident, data-driven decisions. Built for hedge funds, asset allocators, private venture capital firms, and investment bankers, AlphaSense uses advanced AI and powerful search across premium proprietary content to surface the insights that matter most—before the market moves. Elevate your research and stay ahead of the competition. Visit https://www.alpha-sense.com/howiinvest/ to learn more.

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X/Twitter: @dweisburd LinkedIn: https://www.linkedin.com/in/dweisburd/ Weisburd Capital: https://www.weisburdcapital.com/

Stay Connected with Scott Painter:

LinkedIn:https://www.linkedin.com/in/spainter/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

Disclaimer:

This podcast is for informational purposes only and does not constitute investment, financial, legal, or tax advice. Nothing in this episode should be interpreted as an offer to buy or sell any securities or to participate in any investment strategy. All opinions expressed by the host and guests are their own and do not represent the views of Weisburd Capital. Participants may hold positions or have financial interests in the companies, funds, or investments discussed. Any references to specific investments are for illustrative purposes only. Investing involves risk, including the potential loss of capital. Past performance is not indicative of future results, and any forward-looking statements are subject to risks and uncertainties. Any third-party data or opinions have not been independently verified. Listeners should conduct their own research and consult their own advisors before making any investment decisions.

(0:00) Why This Was the Hardest $270M Raise of His Career (1:29) The Deal That Fell Apart a Dozen Times (And Still Closed) (4:56) How He Kept Raising Money After Losing Momentum Repeatedly (6:42) The Breaking Point That Changed Everything Overnight (9:00) The Moment He Was Finally Willing to Walk Away (11:11) The Line Between Conviction and Losing Your Mind (12:04) Why Elon Musk’s Persistence Is on Another Level (13:07) The Real Reason Investors Actually Write Checks (14:27) The Brutal Reality of Entrepreneurial Pressure (16:27) What It Really Means to Bet Everything on One Deal