21st Century Entrepreneurship

#548 Matt Edelman: How Can Brands Win Gamified Consumers?

Matt Edelman is the CEO and president of Super League Enterprise and we spoke about how the gamified consumer mindset is reshaping marketing—and how his own path from Mar

#547 Dean Drako: How Do Product, Timing, and Luck Drive Success?

Dean Drako is a serial entrepreneur who has founded somewhere between five and fifteen companies, raised venture capital around 20 times in Silicon Valley, and experience

#546 Sam Demma: What Happens When You Expect Nothing Back?

Sam Demma is an author and keynote speaker who has delivered close to 850 talks across four continents, and we spoke about how losing a Division I soccer scholarship afte

#545 Amy Perez: Can Dreams Improve Your Decisions?

Amy Perez, CEO at myDream & Mindful Software, Inc. - is a former government technology leader, Lean Six Sigma Black Belt, and responsible AI consultant, and we spoke abou

#544 Saurabh Gupta: Why Do 90% of AI Pilots Fail to Scale?

Saurabh Gupta is CEO of The Modern Data Company, and we spoke about why so many AI initiatives struggle to scale despite massive investment in the technology. His perspec

#543 Digna Deleon-Morris: How Did $5.25 Become $4M a Month?

Digna Deleon-Morris is an entrepreneur and insurance agency CEO, and we spoke about her path from arriving in the United States at 17 and earning $5.25 an hour to buildin

#542 Robert Misheloff: How Do You Avoid a $3,000 Financing Scam?

Robert Misheloff, Smarter Equipment Finance co-owner, is an equipment-financing entrepreneur, and we spoke about how small business owners can finance essential equipment

#541 Luke Girgis: How Do You Turn $400K a Month Into Breakeven?

Luke Girgis is a founder, operator and author, and we spoke about why he believes companies should be designed around workflows rather than org charts. The idea grew out

#540 Marissa Alfe & Lauren Fitzgerald: Why Isn't Talent Enough?

Marissa Alfe & Lauren Fitzgerald is the partnership behind a boutique talent agency PRTNRS MGMT, and we spoke about what it takes to turn creative talent into a durable b

#539 Scott Oldford: Was $100M Worth Losing $14M?

Scott Oldford is a lifelong entrepreneur who built his first seven-figure business at 16, and we spoke about what happened when decades of entrepreneurial instinct collid

#538 Denis O'Shea: How Do You Turn Technology Into Advantage?

Denis O'Shea is the founder and CEO of a technology services company, and we spoke about how a painful sales failure became the foundation for 22 years of helping or

#537 Jonny Price: Can Customers Be Your Best Investors?

Jonny Price is President of WeFunder, and we spoke about why startup investing should no longer be reserved for millionaires—and why founders may be overlooking one of th

#536 Kim Butler: Should You Invest Before Saving $100K?

Kim Butler, Prosperity Thinkers founder, is a financial educator with more than 30 years of experience in banking, investing, and insurance, and we spoke about why strong

#535 Mike Ryan: Can AI Save Investors 80% of Their Time?

Mike Ryan, BPN CEO, is a former Goldman Sachs analyst who later ran its global equity business and managed Harvard’s $18 billion endowment, and we spoke about why powerfu

#534 Chris Majer: Why does coordination fail as companies grow?

Chris Majer is a former University of Washington rugby captain, performance psychologist, and organizational consultant, and we spoke about how practice, mood, and coordi

#533 Simon Mach: How do you build a crypto firm for every cycle?

Simon Mach is a crypto trader and founder of MyCryptoParadise, and we spoke about how a lean operation that began with four traders survived repeated market cycles after

#532 Xavier Rivera: How Did a $300K Trade Erase $60K Debt?

Xavier Rivera is a former U.S. Marine, trader, and financial education mentor, and we spoke about turning a $200 teenage investment into $20,000—then borrowing $60,000, l

#531 Timothy Dougherty: How do meals become measurable wins?

Timothy Dougherty is a fitness entrepreneur and franchisor, founder and CEO of Project LeanNation, and we spoke about rebuilding identity after poverty, financial success

#530 Mike Stone: Can 10 People Scale $5M to $10M?

Mike Stone is President & CEO of CertaPro Painters®, and we spoke about building scalable businesses through trust, proven systems, technology, and values. After more tha

#529 Andy Harris: How Did One Exit Sell for Twice Its Value?

Andy Harris is a former three-time CEO and current President of North American Strategies and Managing Director with STS Capital, and we spoke about how founders can prep