How To Founder

What if the sales process you're so proud of is actually driving away your best prospects? Most founders build elaborate sales machines that prioritize features over feelings, scripts over service, and closing over caring. The result? Ghosted prospects and frustrated founders wondering why their "perfect" process isn't working.

In this eye-opening episode, we sit down with sales powerhouse Drewbie Wilson, who has generated over thirteen million dollars in revenue by flipping the sales script entirely. Discover why authentic conversations beat scripted responses every time, how to build a sales playbook that actually converts, and the three real objections hiding behind every "I need to think about it." Drewbie reveals the counterintuitive truth that selling less actually helps you sell more, and why your next hire might be more important than your next feature.

This isn't another episode about closing techniques or sales funnels. This is about building genuine relationships that turn prospects into customers and customers into advocates.

Keywords: sales playbook, Drewbie Wilson, sales process, objection handling, sales training, entrepreneurship, founder sales, customer relationships, sales strategy

Ever wonder why 70% of million-dollar businesses never reach ten million? The brutal truth is that the scrappy hustle that built your company is now choking it to death.

In this game-changing episode, we sit down with Derek Fredrickson, founder and CEO of The COO Solution, who reveals why founders become their own worst enemy once they hit seven figures. Discover the uncomfortable reality that your biggest strengths are secretly your biggest weaknesses, learn when to stop being the hero of every story, and find out how to build systems that actually work without losing your entrepreneurial soul. This isn't about working harder—it's about working completely differently.

Derek breaks down the visionary-integrator partnership that separates scaling winners from plateau prisoners, plus the exact moment you need to start thinking like a CEO instead of a scrappy startup founder.

Keywords: operational scaling, business systems, fractional COO, visionary integrator, EOS traction, business bottlenecks, Derek Fredrickson

What if the shortcuts you take today are slowly strangling your business tomorrow?

In this eye-opening episode, we dive deep with Sonia Couto, a battle-tested entrepreneur who has spent two decades turning broken tech ideas into thriving global businesses. As managing director of Converge and founder of Minusato and Field Eagle, Sonia reveals the brutal truth about technical debt and why developers spend 42% of their time fixing yesterday's mistakes instead of building tomorrow's breakthroughs.

Discover why even Salesforce had to completely rebuild their platform three times in the first five years, learn the art of modular architecture that saves companies from catastrophic rebuilds, and understand when duct tape solutions actually work versus when they'll destroy your scaling potential. This episode will fundamentally change how you think about building sustainable technology.

Keywords: technical debt, scaling software, startup technology, modular architecture, MVP development, legacy systems, software development, tech entrepreneurship

What if the secret to entrepreneurial success isn't competing with other founders, but collaborating with them?

In this game-changing episode, we sit down with Jan van Schuppen, a seasoned entrepreneur and sales expert who's made it his mission to lift up other founders through his unique "services for shares" model. Discover why the most successful entrepreneurs actively mentor others, how helping fellow founders can accelerate your own growth, and the surprising psychology behind why asking for help actually makes you more likable. Jan reveals his contrarian take on founder communities, shares his Benjamin Franklin effect strategy, and explains why some of the best business advice comes from getting outside your comfort zone. This isn't just about networking—it's about building a support system that transforms lonely entrepreneurs into thriving business leaders.

Keywords: entrepreneur mentorship, founder collaboration, startup community, business coaching, entrepreneurial support, Jan van Schuppen, services for shares, Benjamin Franklin effect, founder networking

What if the smartest founders are actually sabotaging their own success?

In this eye-opening episode, we dive deep with Lee Povey, a transformation coach who's spent two decades turning technically brilliant founders into emotionally intelligent leaders who can scale. Discover why 70% of high IQ founders struggle to break the $10 million revenue barrier, the four-part emotional framework that Navy SEALs use under pressure, and why Reed Hastings fired his entire Netflix executive team despite their technical prowess. Lee breaks down the simple six-emotion model that successful founders use to regulate themselves and reveals why being right isn't the same as being effective. This isn't feel-good advice—it's battle-tested neuroscience for founders who want to stop being their own biggest bottleneck.

Keywords: emotional intelligence, founder development, Lee Povey, startup scaling, leadership skills, EQ vs IQ, founder psychology, business growth

What if your biggest setback becomes your greatest setup for building a $100 million empire?

When Dr. Brent Ridge and Josh Kilmer-Purcell lost their New York City corporate jobs during the 2008 recession, they had nothing left but a struggling farm and 80 goats from a neighbor named Farmer John. Fast forward sixteen years, and they've built Beekman 1802 into a global beauty empire worth over $100 million—all by harnessing the power of their tiny 547-person community.

Discover the unconventional strategies they used to turn neighbors into salespeople, how they made their community the hero of their brand story, and why measuring kindness actually drives bottom-line results. This isn't your typical startup success story—it's proof that sometimes the smallest circles create the biggest businesses.

Keywords: community building, Beekman 1802, local business growth, brand storytelling, customer loyalty, rural entrepreneurship, authentic marketing

What if the secret to better decisions isn't learning more frameworks, but trusting what you already know?

In this eye-opening episode, we dive deep into the hidden world of mental models—the unconscious frameworks driving every business decision you make. Discover why 90% of startups fail while others seem to navigate challenges with supernatural clarity, and learn how to build your own decision-making system that actually works. We explore the dangerous trap of adopting other people's frameworks, the power of aligning your business with your core values, and why the best founders learn to think less stupidly rather than more cleverly. Plus, we tackle the destructive mental models that keep entrepreneurs frozen in critical moments and reveal a practical approach to codifying your own decision-making process.

Keywords: mental models, decision making, startup failure, entrepreneurship, business alignment, core values, founder mindset, strategic thinking

What if everything you think you know about keeping great people is wrong?

In this eye-opening episode, we dive deep with Francie Jain, founder of Terrawada B2B Marketplace, who reveals why your best employees might already have one foot out the door. Discover the shocking truth about employee turnover costs, why ping pong tables and snacks won't save you, and the real reasons high performers leave. Francie shares a powerful case study of how one organization slashed turnover from 24% to 4% and saved $32 million annually. Learn the psychological principles that Google uses to build their most productive teams, and why professional development beats perks every time. This isn't about throwing money at the problem—it's about understanding what drives human motivation and creating a workplace where people genuinely want to stay and grow.

Keywords: employee retention, Francie Jain, turnover costs, professional development, psychological safety, company culture, talent management, startup leadership

What if your obsession with rapid growth is secretly destroying everything you've built?

Join us for our milestone 100th episode as we sit down with John St. Pierre, who learned this lesson the hard way. After getting fired from his own $50 million company despite raising $20 million in funding, John discovered the brutal truth: growth for growth's sake can kill you. Now, he's built his next venture to over $100 million using seven strategic principles that prioritize smart scaling over reckless expansion. Discover why protecting your equity matters more than raising capital, how to build your own growth engine without investor dependency, and the hidden formula for sustainable wealth creation that most founders completely miss. This episode challenges everything you think you know about scaling a business.

Keywords: scaling strategies, equity protection, sustainable growth, entrepreneurial wealth, business capital, founder principles, smart scaling

What separates a napkin sketch that becomes a billion-dollar business from one that becomes an expensive lesson? Serial entrepreneur Dennis R. Mortensen has turned four bar napkin concepts into successful company exits and reveals the counterintuitive truth: there's no formula for success, only ways to increase your odds from 0.04 to 0.07. Discover his "list of hate" method for identifying real pain points, why he tries to kill every idea before building it, and the single metric that should drive your entire business. Dennis shares how Launch Brightly automates screenshot management for software companies and why being world-class at one tiny thing beats being half-decent at seven. This episode unpacks the harsh reality that most first-time founders never make a single dollar and the sales muscle every founder must develop to survive.

Keywords: startup ideas, Dennis Mortensen, billion dollar business, entrepreneur validation, Launch Brightly, pain point identification, startup execution, founder sales skills