21st Century Entrepreneurship

Bölümler

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  #547 Dean Drako: How Do Product, Timing, and Luck Drive Success? 14.09.2026 15dk

  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 experienced both successful exits and failures—and we spoke about the operating lessons that came from building repeatedly. His starting principle is simple: find a pain point you understand deeply, make sure many other people share it, and build what he calls “painkillers, not vitamins.” Dean also breaks company growth into thre...
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  #546 Sam Demma: What Happens When You Expect Nothing Back? 11.09.2026 17dk

  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 after three major knee injuries redirected his life toward service, storytelling, and speaking. A teacher challenged him to take small, consistent action, which led to five and a half years of community cleanups—and eventually to schools inviting him back as a paid speaker. Sam also explains the practical principles behind his la...
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  #545 Amy Perez: Can Dreams Improve Your Decisions? 11.09.2026 19dk

  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 about using dreams as another source of information for decisions, self-awareness, and major life changes. After years managing high-stakes programs - including a digital system that distributed more than $10 billion in pandemic aid - Amy was outwardly successful but exhausted: “I was slowly dying on the inside.” A violent dr...
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  #544 Saurabh Gupta: Why Do 90% of AI Pilots Fail to Scale? 08.09.2026 20dk

  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 perspective comes from nearly 30 years in data: designing the World Bank’s open data platform, spending 12 years leading statistical data at the IMF, serving as Chief Data Officer for Washington, DC, and later working across more than 20 major enterprise data initiatives at Thoughtworks. Across those environments, he kept seeing the...
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  #543 Digna Deleon-Morris: How Did $5.25 Become $4M a Month? 31.08.2026 16dk

  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 building an agency doing almost $4 million a month. Before entrepreneurship, she earned two college degrees, supervised 30 locations and managed $82 million in operations while working seven days a week — but, as a mother of four, realized, “I was building somebody else's business.” The turning point was painful: after making ...
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  #542 Robert Misheloff: How Do You Avoid a $3,000 Financing Scam? 25.08.2026 15dk

  Robert Misheloff, Smarter Equipment Finance co-owner, is an equipment-financing entrepreneur, and we spoke about how small business owners can finance essential equipment without falling into costly traps. After running direct marketing campaigns for financing companies, Robert saw firms brag about how they “pulled the wool over the eyes of their customers.” That experience pushed him to build a business around transparency and helping owners make informed financing decisions. Robert br...
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  #541 Luke Girgis: How Do You Turn $400K a Month Into Breakeven? 19.08.2026 11dk

  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 of businesses where revenue increased but efficiency did not: while running Rolling Stone and Variety Australia, margins never exceeded 4% because new revenue continually required more people. Looking back, Luke says, “we were just buying revenue with labor.” That lesson became urgent when Luke stepped into an interim C...
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  #540 Marissa Alfe & Lauren Fitzgerald: Why Isn't Talent Enough? 17.08.2026 24dk

  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 business. After years in artist representation, they launched their own agency as COVID upended the industry; Marissa remembers, “I had $800 in my checking account,” while still needing to protect clients she had spent years building. Their response was to help artists become more visible, commercially valuable and entrepr...
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  #539 Scott Oldford: Was $100M Worth Losing $14M? 11.08.2026 25dk

  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 collided with an identity he was trying to force. By 2022, he was making roughly $7 million a year at a 70% profit margin while working 15–20 hours a week. Then he chased a bigger identity and a $100 million outcome, losing $14 million across 2023 and 2024. Looking back, Scott says the difference between entrepreneurship as a “beau...
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  #538 Denis O'Shea: How Do You Turn Technology Into Advantage? 08.08.2026 26dk

  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 organizations extract more value from technology. Early in his career at Nokia, a customer challenged him on why they should buy more technology when employees barely used what they already had. Denis says that conversation “burnt a piece of my brain.” He later built a 250-person mentoring operation that worked one-on-one with a mil...
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  #537 Jonny Price: Can Customers Be Your Best Investors? 05.08.2026 25dk

  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 their strongest sources of capital: their own customers. He explains how changes in U.S. regulation opened private investing to everyday people and why that shift creates opportunities not only for investors, but also for entrepreneurs who struggle to access traditional venture capital. Rather than positioning community investi...
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  #536 Kim Butler: Should You Invest Before Saving $100K? 03.08.2026 18dk

  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 earners often build wealth in the wrong order. Her starting question is direct: “You’re awesome at making money. How much of it are you keeping?” Rather than beginning with investment products, she helps entrepreneurial thinkers establish principles for making their own financial decisions. After a decade in the financial in...
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  #535 Mike Ryan: Can AI Save Investors 80% of Their Time? 31.07.2026 24dk

  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 powerful AI still fails investors when its answers cannot be trusted. After repeatedly receiving polished but incorrect information from generic tools, he decided to develop a more reliable approach. As he puts it, “AI wouldn’t pass a first-round job interview at most firms because it’s not trustworthy.” Ryan explains that AI has a ...
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  #534 Chris Majer: Why does coordination fail as companies grow? 29.07.2026 32dk

  Chris Majer is a former University of Washington rugby captain, performance psychologist, and organizational consultant, and we spoke about how practice, mood, and coordination determine whether growing companies can actually transform. An airport-bookstore encounter with George Leonard’s The Ultimate Athlete led him from rugby into Aikido, sports psychology, and work with elite athletes, Olympic teams, and Special Forces. That path eventually took his methods into business, where a 48-month ...
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  #533 Simon Mach: How do you build a crypto firm for every cycle? 28.07.2026 14dk

  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 launching in 2016. When meme-coin bets that worked during bull markets vanished in a downturn, Simon stopped chasing potential 1,000% gains and developed a professional approach guided by one hierarchy: “Capital protection first, consistency second, and growth third.” He explains why professionals calculate potential losses b...
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  #532 Xavier Rivera: How Did a $300K Trade Erase $60K Debt? 24.07.2026 27dk

  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, losing most of it, and spending four years trapped in debt. At 17, he entered the military believing his basic needs would be covered while he learned the markets, but the failed pharmaceutical trade pushed him so far into pressure that, as he says, “I was so deep in survival mode.” During a nine-month deployment aboard the US...
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  #531 Timothy Dougherty: How do meals become measurable wins? 22.07.2026 31dk

  Timothy Dougherty is a fitness entrepreneur and franchisor, founder and CEO of Project LeanNation, and we spoke about rebuilding identity after poverty, financial success, federal prison, and the collapse of everything he had tied his value to. The gym was the first place “where pain had purpose,” and keeping a small promise—to arrive at 6:00 each morning—gave him evidence that he could become disciplined. Years later, despite the house, Porsche, boat, and growing family, he says, “I never fe...
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  #530 Mike Stone: Can 10 People Scale $5M to $10M? 20.07.2026 15dk

  Mike Stone is President & CEO of CertaPro Painters®, and we spoke about building scalable businesses through trust, proven systems, technology, and values. After more than 26 years with the organization, Mike believes sustainable growth comes from moving beyond individual projects toward long-term relationships because “projects end,” while strong customer relationships endure. Mike explained how franchising lets entrepreneurs be “in business for yourself, not by yourself,” combining inde...
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  #529 Andy Harris: How Did One Exit Sell for Twice Its Value? 17.07.2026 25dk

  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 prepare their companies for an exit that delivers more than standard market value. After completing more than 20 acquisitions and six exits, Andy learned M&A by “being in the shoes” of business owners—building companies, managing daily operations, and preparing them for strategic buyers. His central advice is to remove “found...
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  #528 Sam Rosenberg: How Do You Spot Danger Before It Strikes? 15.07.2026 32dk

  Sam Rosenberg is a former Marine officer and close-protection specialist, and we spoke about how ordinary people can recognize danger, avoid freezing under pressure, and protect those they love. After safeguarding prominent public figures, he concluded that “it’s good to have a lifeguard, but ultimately you should know how to swim”—meaning people should learn the same foundational thinking skills used by professional protectors. His turning point came before the Marines, when a man pointed a ...