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21st Century Entrepreneurship: Daily Summaries Delivered
by Martin Piskoric
21st Century Entrepreneurship is an entrepreneurship podcast featuring candid conversations with founders, CEOs, investors, executives, creators, and business leaders from around the world. The show has published more than 540 interviews exploring how businesses are built, funded, scaled, transformed, and sometimes rebuilt from failure. Episodes cover entrepreneurship, leadership, business strategy, startup growth, marketing, finance and investment, AI and technology, personal development, and the decisions behind successful companies and careers. Rather than polished success stories, the show focuses on practical experience: what worked, what failed, what changed, and what other entrepreneurs can apply.
Latest Episodes
The most recent episodes — sign up to get AI-powered summaries of each one.
- 3 days ago21 min
#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 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, distribution, and production all moving at once. When the pandemic eliminated the live-event foundation of t...
- 6 days ago15 min
#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 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...
- 1 weeks ago17 min
#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 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...
- 1 weeks ago19 min
#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 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...
- 1 weeks ago20 min
#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 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...
- 2 weeks ago16 min
#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 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 ...
- 3 weeks ago15 min
#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 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...
- Aug 19, 202611 min
#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 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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About 21st Century Entrepreneurship
21st Century Entrepreneurship is an entrepreneurship podcast featuring candid conversations with founders, CEOs, investors, executives, creators, and business leaders from around the world. The show has published more than 540 interviews exploring how businesses are built, funded, scaled, transformed, and sometimes rebuilt from failure. Episodes cover entrepreneurship, leadership, business strategy, startup growth, marketing, finance and investment, AI and technology, personal development, and the decisions behind successful companies and careers. Rather than polished success stories, the show focuses on practical experience: what worked, what failed, what changed, and what other entrepreneurs can apply.
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Frequently Asked Questions
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