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

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

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/]

Show the Real Chapters with Brooke Sellas

During COVID, Brooke Sellas posted something honest on Instagram - two words: “I am so tired.” She wasn’t complaining. She was being human. The mentor she’d hired to help her build her personal brand told her it was a mistake. Leaders only show the good parts, they said. Brooke almost believed it. Brooke is the founder and CEO of B Squared Media, a social media agency she bootstrapped - with no funding, no sales team, just herself - to a seven-figure business over 14 years. Her company’s whole philosophy is built on a trademarked tagline: Think Conversation, Not Campaign. So when a paid expert told her to hide her real feelings and only project perfection, it didn’t just sting personally. It cut against everything she’d built. In this episode, she unpacks why that advice was so damaging, why she almost took it anyway, and what it actually takes to trust yourself when someone you respect tells you you’re wrong. What you’ll learn: * Why “only show your best self” advice - however well-intentioned - can quietly undermine the trust you’re trying to build * The social penetration theory Brooke studied in college that still explains why vulnerability works on social media (and in business) * What she did when a mentor lambasted her for showing up authentically, and how long it really took to recover * Why imposter syndrome hits women founders harder, and what helped Brooke finally snap out of the spiral * How to build discernment about whose advice is worth taking, and how to spot when advice isn’t actually coming from a good place * The question every founder should ask before taking advice: “Who benefits from me doing this?” * Why Brooke now publicly shares when her business is down, and what happened when she did About Brooke Sellas Brooke Sellas is the founder and CEO of B Squared Media, a social media agency specializing in VIP customer care on social channels for enterprise clients. She bootstrapped B Squared to seven figures over 14 years without outside funding or a sales team. Her company’s approach is rooted in a simple but powerful idea - Think Conversation, Not Campaign - and in the psychology of how humans actually build relationships and trust. Before founding B Squared, Brooke spent years in social media strategy at another company, and her undergraduate thesis on the social penetration theory has shaped her philosophy ever since. She’s a connector, a community builder, and a founder who has learned - sometimes the hard way - that being real is always the right strategy. This episode is for anyone who has been told to put a better face on it, and is wondering whether their real face might actually be the better strategy. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Brooke on LinkedIn [https://www.linkedin.com/in/brookebsellas/] 💼 Learn more about B Squared Media: bsquared.media [https://bsquared.media]

Be More Difficult with Katie Robbert

Katie Robbert has been told to stay quiet, stay in her lane, and let someone else be the face of the company. She heard it from a mentor she respected. She heard it from investors. She heard it so many times she almost believed it. She didn’t.  Katie is the CEO of Trust Insights, an AI education and analytics firm she co-founded eight years ago. And she holds that title deliberately, because someone told her she shouldn’t.  In this episode, she pulls back the curtain on what it actually took to get there: the verbally abusive VP she was told to just tolerate, the investor feedback that nearly made her hand over the CEO seat, and why she’s now built a virtual version of herself to run ideas past before they get to her. The answer is always the same: it’s going to ask a million questions. What you’ll learn: * Why “don’t rock the boat” advice - however well-intentioned - can quietly wire you to shrink instead of lead * What Katie did when investors told her a female CEO would tank her chances of funding * How to tell the difference between a battle worth fighting and one that will just cost you * Why the people who say yes to everything are the ones who keep leaving, and what Katie looks for instead * How Trust Insights built a virtual Katie Robbert AI trained on her own decision-making style (and why the team runs ideas past it first) * What real community looks like for founders who need someone to be honest with - not impressed by them About Katie Robbert Katie Robbert is the CEO of Trust Insights, a data analytics and AI education firm she co-founded with Christopher Penn in 2017. With over 15 years in AI and analytics, she has built a reputation for asking the questions other people are afraid to ask - in client work, in company culture, and in every room she walks into. Trust Insights serves organizations navigating real-world AI adoption and has been a resource in the space long before generative AI became a boardroom talking point. Katie is an introvert who runs a public-facing company, a pragmatist who works alongside one of the most innovative minds in marketing AI, and a CEO who was told she shouldn’t be one. This episode is for anyone who has been handed advice that was really just a request to make themselves smaller — and is trying to figure out when to ignore it. 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Katie on LinkedIn [https://www.linkedin.com/in/katierobbert/] 💼 Learn more about Trust Insights: https://www.trustinsights.aitrustinsights.ai [http://trustinsights.ai]

Operate Out of Abundance with Ted Harrison

Ted Harrison has heard the advice a hundred times: negotiate everything, ask for the friends and family discount, don’t spend what you don’t have to. He heard it from other agency founders. From coaches. From people who have genuinely built successful businesses. He thought about it, and then he emailed a vendor to ask them to charge him more. That’s not a bit. That’s just how Ted builds. The founder of Neuemotion, a 360 full-service B2B marketing agency, Ted doesn’t believe in treating cash as scarcity. His first principle as a company: operate out of the abundance of what’s possible, not the fear of what might happen. Two and a half years in, bootstrapped, and named one of Ad Age’s Best Places to Work, he’s got some evidence it’s working. What you’ll learn: * Why “save your money” advice - however well-intentioned - can quietly wire you to build from fear instead of possibility * How Ted’s 10 company values actually function as a decision-making system (and why one of them explicitly says Neuemotion is not your family) * What building a business inside Twitter taught him about transparency, ownership culture, and running a p&l * Why Ted has a personal AI agent trained on years of his own writing - and uses it as a gut-check mirror when no one else is in the room * The one piece of advice Ted gives every founder: build values that actually fit you - because friction you create for yourself is the worst kind About Ted Harrison Ted Harrison is the CEO and Founder of Neuemotion, a 360 full-service agency for B2B marketers. Before starting Neuemotion, he spent six years at Twitter - including a year at X post-acquisition - where he built an internal business that drove significant revenue and learned what it actually looks like to run a company from the inside out. He left in 2023 and bootstrapped Neuemotion from day one, building it around 10 company values that function less like a culture deck and more like an operating system. Neuemotion was named to Ad Age’s Best Places to Work in 2026. Ted is also a believer in paying full price - especially for friends. This episode is a masterclass in what happens when you stop optimizing for the worst-case scenario and start building from what’s actually possible - and why that shift in mindset might be the most practical business decision you ever make. TIMESTAMPS [0:00] The Bad Advice: “Don’t Spend Your Money” [00:42] Meet Ted Harrison [03:23] Abundance Over Scarcity [04:14] Friends Pay Full Price [06:17] Spend on Quality People [08:15] Values in Daily Decisions  [13:35] Neuemotion Values [19:55] Using AI as a Mirror [21:54] Discernment in Spending  [25:26] Best Advice for Founders 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Ted on LinkedIn [https://www.linkedin.com/in/tedaharrison/] 💼 Learn more about Neuemotion: https://numotion.cohttps://www.neuemotion.com/

Think Smaller? No Thanks. with Nomiki Petrolla

Nomiki Petrolla gets told to think smaller. A venture contact - someone who didn’t know her well enough - looked at her vision for Theanna and decided the problem she’s solving is probably just a “lifestyle business.” Nomiki, who has been obsessively building for 15 years, collecting data points and ignoring the noise, heard the feedback and thought: no thanks. Then she moved on. What you'll learn: * Why “think smaller” advice usually says more about the advisor’s belief in you than the actual size of your idea * How to turn founder feedback into data - and why documenting everything changes the way you filter signal from noise * The four things your inner circle actually needs to have (hint: one of them is macro and micro-economic fluency) * How Nomiki found investors, founders, and $138K in ARR through organic TikTok - by building in public before it felt safe * Why the self-work isn’t a side quest - it’s the whole game for founders who want to think and build big About Nomiki Petrolla Nomiki Petrolla is the Founder and CEO of Theanna, an AI platform that combines community and adjacent systems to help women builders create companies. She started Theanna because she identified systemic gaps in how women founders access product development knowledge. Before Theanna, she spent 15 years in the zero-to-one stage of business, surrounded entirely by founders and builders. She’s been networking that long too, which is why her founding engineer is someone she worked with in her first job in 2012. She lives all of this out loud on TikTok, which is also somehow where she found investors. This episode is a masterclass in data-driven discernment — how to collect feedback obsessively, filter it ruthlessly, and trust yourself anyway. Especially when the feedback is coming from venture. TIMESTAMPS * [00:00] The Bad Advice * [00:39] Meet Nomiki Petrolla, Founder & CEO of Theanna * [01:01] Think Smaller?  * [03:06] Filtering Feedback with Data * [05:05] Document and Analyze Advice * [06:35] Gut Checks and Trusted Circle * [08:58] Finding the Right People * [10:10] Networking and TikTok Flywheel * [14:40] Mission Values and Why It Matters * [18:27] Family Support and Relationships * [23:07] Reframing Think Smaller * [25:20] Closing and Call to Action 📩 Subscribe to the newsletter: lindsaytjepkema.substack.com [http://lindsaytjepkema.substack.com/]  🔗 Follow Lindsay on LinkedIn [https://www.linkedin.com/in/lindsaytjepkema/] 🔗 Follow Nomiki on LinkedIn [https://www.linkedin.com/in/nomikipetrolla/] 🌱 Learn more about Theanna: theanna.io [https://theanna.io/]