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21st Century Entrepreneurship

21st Century Entrepreneurship

Martin Piskoric 540 Episodes Sep 17, 2026

The 21st Century Entrepreneurship Podcast is a weekly show that features interviews with successful entrepreneurs and leaders. It covers the fundamentals of starting and growing a business, achieving and maintaining success, and the challenges entrepreneurs face. The show also explores the future of entrepreneurship and offers insights for staying competitive. It has received four Gold Awards for its content.

Episodes

#548 Matt Edelman: How Can Brands Win Gamified Consumers?
#548 Matt Edelman: How Can Brands Win Gamified Consumers? Sep 17, 2026 1296 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 Marvel and film production unexpectedly prepared him to run a public company. He describes producing a film as surprisingly close to running a business: “a film is like a mini company,” with budgets, contracts, marketing, distributio
#547 Dean Drako: How Do Product, Timing, and Luck Drive Success?
#547 Dean Drako: How Do Product, Timing, and Luck Drive Success? Sep 14, 2026 923 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
#546 Sam Demma: What Happens When You Expect Nothing Back?
#546 Sam Demma: What Happens When You Expect Nothing Back? Sep 11, 2026 1048 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 scho
#545 Amy Perez: Can Dreams Improve Your Decisions?
#545 Amy Perez: Can Dreams Improve Your Decisions? Sep 11, 2026 1194 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 a
#544 Saurabh Gupta: Why Do 90% of AI Pilots Fail to Scale?
#544 Saurabh Gupta: Why Do 90% of AI Pilots Fail to Scale? Sep 8, 2026 1257 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
#543 Digna Deleon-Morris: How Did $5.25 Become $4M a Month?
#543 Digna Deleon-Morris: How Did $5.25 Become $4M a Month? Aug 31, 2026 1008 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, realiz
#542 Robert Misheloff: How Do You Avoid a $3,000 Financing Scam?
#542 Robert Misheloff: How Do You Avoid a $3,000 Financing Scam? Aug 25, 2026 943 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 b
#541 Luke Girgis: How Do You Turn $400K a Month Into Breakeven?
#541 Luke Girgis: How Do You Turn $400K a Month Into Breakeven? Aug 19, 2026 697 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 jus
#540 Marissa Alfe & Lauren Fitzgerald: Why Isn't Talent Enough?
#540 Marissa Alfe & Lauren Fitzgerald: Why Isn't Talent Enough? Aug 17, 2026 1490 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 bu
#539 Scott Oldford: Was $100M Worth Losing $14M?
#539 Scott Oldford: Was $100M Worth Losing $14M? Aug 11, 2026 1537 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
#538 Denis O'Shea: How Do You Turn Technology Into Advantage?
#538 Denis O'Shea: How Do You Turn Technology Into Advantage? Aug 8, 2026 1607 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
#537 Jonny Price: Can Customers Be Your Best Investors?
#537 Jonny Price: Can Customers Be Your Best Investors? Aug 5, 2026 1510 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 entreprene

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