Selling With ADHD: Confidence Without the Sleaze or Burnout (with Wes Schaeffer)
If sales feels heavy, awkward, or mentally exhausting, it’s probably not because you’re bad at it.
It’s more likely because you’ve been trying to sell using advice that relies on pressure, performance, or rigid systems - the exact things that make ADHD brains freeze, overthink, or avoid the conversation altogether.
In this episode, Skye sits down with Wes Schaeffer (The Sales Whisperer) to talk about how to sell in a way that actually feels calm, grounded, and sustainable — without hype, manipulation, or forcing yourself into a persona that doesn’t fit.
This isn’t about “loving sales” or magically becoming confident.
It’s about:
- reducing anxiety around money conversations
- having something to lean on when your confidence dips
- and building just enough structure so sales stops living rent-free in your head
Wes breaks down why money talk feels so uncomfortable, how scripts can reduce stress instead of making you sound robotic, and why avoiding systems usually creates more chaos — not less.
If you’ve ever known you should follow up, talk about pricing, or ask for the sale… and still found yourself procrastinating, this conversation will feel uncomfortably accurate — in a good way.
No hustle. No sleaze. No “just be confident” advice.
In this episode, we talk about:
- Why sales feels uncomfortable for ADHD entrepreneurs and what is actually happening underneath that resistance
- How to talk about money and pricing without sounding pushy or rehearsed
- When scripts and systems help ADHD brains and when they make things worse
- A calmer approach to follow-ups that does not rely on pressure or guilt
- How small sales systems reduce burnout, decision fatigue, and avoidance over time
Connect with Wes Schaeffer
- Learn more about Wes and his programs: https://12weekstopeak.com
- Free habit tracker and practical sales resources available on the site
- Text or book time directly via the site
About ADHD founders for ADHD founders.
Interesting in working together? You can click here to receive a free bottleneck audio session and learn more about what we do. https://www.unconventionalorganisation.com/unstuckaudiosession
Diagnosed with ADHD at the start of her PhD, Skye Waterson spent years researching what actually works and writing about it for thousands of founders. The pattern she kept finding: ADHD business owners don't have a focus problem, they have an operations problem, because the whole business runs through their own head. Now she and her husband, former programmer Robert Waterson, work as fractional COOs for those founders. They find the bottleneck, hire the fix, and build the system that holds.
Subscribe to our Newsletter - https://unconventionalorganization.substack.com/
Follow us on Instagram - @unconventionalorganisation
Visit our website - https://www.unconventionalorganisation.com/
More description
If sales feels heavy, awkward, or mentally exhausting, it’s probably not because you’re bad at it.
It’s more likely because you’ve been trying to sell using advice that relies on pressure, performance, or rigid systems - the exact things that make ADHD brains freeze, overthink, or avoid the conversation altogether.
In this episode, Skye sits down with Wes Schaeffer (The Sales Whisperer) to talk about how to sell in a way that actually feels calm, grounded, and sustainable — without hype, manipulation, or forcing yourself into a persona that doesn’t fit.
This isn’t about “loving sales” or magically becoming confident.
It’s about:
- reducing anxiety around money conversations
- having something to lean on when your confidence dips
- and building just enough structure so sales stops living rent-free in your head
Wes breaks down why money talk feels so uncomfortable, how scripts can reduce stress instead of making you sound robotic, and why avoiding systems usually creates more chaos — not less.
If you’ve ever known you should follow up, talk about pricing, or ask for the sale… and still found yourself procrastinating, this conversation will feel uncomfortably accurate — in a good way.
No hustle. No sleaze. No “just be confident” advice.
In this episode, we talk about:
- Why sales feels uncomfortable for ADHD entrepreneurs and what is actually happening underneath that resistance
- How to talk about money and pricing without sounding pushy or rehearsed
- When scripts and systems help ADHD brains and when they make things worse
- A calmer approach to follow-ups that does not rely on pressure or guilt
- How small sales systems reduce burnout, decision fatigue, and avoidance over time
Connect with Wes Schaeffer
- Learn more about Wes and his programs: https://12weekstopeak.com
- Free habit tracker and practical sales resources available on the site
- Text or book time directly via the site
About ADHD founders for ADHD founders.
Interesting in working together? You can click here to receive a free bottleneck audio session and learn more about what we do. https://www.unconventionalorganisation.com/unstuckaudiosession
Diagnosed with ADHD at the start of her PhD, Skye Waterson spent years researching what actually works and writing about it for thousands of founders. The pattern she kept finding: ADHD business owners don't have a focus problem, they have an operations problem, because the whole business runs through their own head. Now she and her husband, former programmer Robert Waterson, work as fractional COOs for those founders. They find the bottleneck, hire the fix, and build the system that holds.
Subscribe to our Newsletter - https://unconventionalorganization.substack.com/
Follow us on Instagram - @unconventionalorganisation
Visit our website - https://www.unconventionalorganisation.com/
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