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Scotty’s Little Sales Club Will Never Work with Scott Leese

34 min · 26 de may de 2026
Portada del episodio Scotty’s Little Sales Club Will Never Work with Scott Leese

Descripción

Scott Leese’s first sales manager pulled him into his office, looked him dead in the eye, and told him to stop caring so much about his people. Stop going to lunch with them. Stop being their friend. Draw a harder line. Then he said something that has lived rent-free in Scott’s head for over 20 years: “Scotty’s little sales club is never gonna work.” Scott didn’t listen. He built his teams the way he wanted to; caring about the person first, more than the number, more than the company, more than the founders’ eventual payday. He hired the people everyone else passed on: someone living in their car, someone just out of prison, single parents rebuilding from scratch. He never looked at a resume. He asked people where they wanted to go and why they were finally ready to do what they’d been unwilling to do before. And he won. Over and over. He’s a six-time sales leader, serial entrepreneur, consultant to early-stage founders, and the guy who eventually named his own coaching community Scotty’s Little Sales Club… out of spite. In this episode, he talks about where that stubbornness comes from, what four years in the hospital taught him about what actually matters, and why caring about humans isn’t a soft strategy - it’s the only one that holds up. What you’ll learn: * Why “draw a harder line” advice - from people who confuse rigidity with leadership - can cost you the trust that actually drives performance * What Scott’s four years in the hospital (and the years rebuilding after) gave him that no business school ever could * How he built his teams by betting on the people everyone else had already written off. and why it kept working * What his one-on-ones actually looked like (hint: no pipeline reviews, lots of walks around the building) * Why telling your employees that AI is going to replace them is not just tone-deaf - it’s strategically dangerous * What the VC ecosystem looks like right now and why founders may need capital less than they think * The one question he asked every candidate instead of reading their resume: why are you willing now to do what you’ve previously been unwilling to do? * Why “treat humans like humans” is the through-line from early sales leader to serial entrepreneur to founder coach About Scott Leese Scott Leese is a six-time sales leader, serial entrepreneur, and the founder of Scott Leese Consulting, where he works with early-stage companies navigating the zero-to-$25M go-to-market journey. He also runs Surf and Sales Summit, a consumer product business, a landscaping company, two venture capital firms, and two podcasts - because apparently he can’t stop starting things. Scott came to his career late: after four years in the hospital, nine surgeries, and kicking an opioid dependency at 27, he walked into his first sales job with no resume worth looking at and the unshakeable conviction that whoever took a chance on him wasn’t going to regret it. They didn’t. He’s spent the 20 years since paying that forward — hiring the people others overlook, leading teams with radical openness, and building a reputation as someone who genuinely gives a shit about the people who work with him. This episode is for anyone who has been told their style is too soft, their team is too close, or their people skills are getting in the way of real leadership - and is wondering whether the person saying that has ever actually built anything worth following. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Scott on LinkedIn [https://www.linkedin.com/in/scottleese/] 💼 Learn more about Scott Leese Consulting: scottleeseconsulting.com [https://scottleeseconsulting.com/]

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episode Scotty’s Little Sales Club Will Never Work with Scott Leese artwork

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Scott Leese’s first sales manager pulled him into his office, looked him dead in the eye, and told him to stop caring so much about his people. Stop going to lunch with them. Stop being their friend. Draw a harder line. Then he said something that has lived rent-free in Scott’s head for over 20 years: “Scotty’s little sales club is never gonna work.” Scott didn’t listen. He built his teams the way he wanted to; caring about the person first, more than the number, more than the company, more than the founders’ eventual payday. He hired the people everyone else passed on: someone living in their car, someone just out of prison, single parents rebuilding from scratch. He never looked at a resume. He asked people where they wanted to go and why they were finally ready to do what they’d been unwilling to do before. And he won. Over and over. He’s a six-time sales leader, serial entrepreneur, consultant to early-stage founders, and the guy who eventually named his own coaching community Scotty’s Little Sales Club… out of spite. In this episode, he talks about where that stubbornness comes from, what four years in the hospital taught him about what actually matters, and why caring about humans isn’t a soft strategy - it’s the only one that holds up. What you’ll learn: * Why “draw a harder line” advice - from people who confuse rigidity with leadership - can cost you the trust that actually drives performance * What Scott’s four years in the hospital (and the years rebuilding after) gave him that no business school ever could * How he built his teams by betting on the people everyone else had already written off. and why it kept working * What his one-on-ones actually looked like (hint: no pipeline reviews, lots of walks around the building) * Why telling your employees that AI is going to replace them is not just tone-deaf - it’s strategically dangerous * What the VC ecosystem looks like right now and why founders may need capital less than they think * The one question he asked every candidate instead of reading their resume: why are you willing now to do what you’ve previously been unwilling to do? * Why “treat humans like humans” is the through-line from early sales leader to serial entrepreneur to founder coach About Scott Leese Scott Leese is a six-time sales leader, serial entrepreneur, and the founder of Scott Leese Consulting, where he works with early-stage companies navigating the zero-to-$25M go-to-market journey. He also runs Surf and Sales Summit, a consumer product business, a landscaping company, two venture capital firms, and two podcasts - because apparently he can’t stop starting things. Scott came to his career late: after four years in the hospital, nine surgeries, and kicking an opioid dependency at 27, he walked into his first sales job with no resume worth looking at and the unshakeable conviction that whoever took a chance on him wasn’t going to regret it. They didn’t. He’s spent the 20 years since paying that forward — hiring the people others overlook, leading teams with radical openness, and building a reputation as someone who genuinely gives a shit about the people who work with him. This episode is for anyone who has been told their style is too soft, their team is too close, or their people skills are getting in the way of real leadership - and is wondering whether the person saying that has ever actually built anything worth following. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Scott on LinkedIn [https://www.linkedin.com/in/scottleese/] 💼 Learn more about Scott Leese Consulting: scottleeseconsulting.com [https://scottleeseconsulting.com/]

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episode Operate Out of Abundance with Ted Harrison artwork

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