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21st Century Entrepreneurship

21st Century Entrepreneurship

Martin Piskoric

21st Century Entrepreneurship

Entrepreneurship Self-Improvement Business News English

An entrepreneurship podcast that transforms in-depth interviews with founders, CEOs, investors, executives, creators, and business leaders into tightly edited, first-person narratives that distill what matters most from their real-world experience.

A four-time Gold Award-winning show with more than 540 published interviews, 21st Century Entrepreneurship explores how businesses are built, funded, scaled, transformed, and sometimes rebuilt from failure.

Host Martin Piskoric guides each conversation toward the moments, decisions, lessons, and experiences most useful to listeners, then steps out of the final edit. What remains is the guest's voice—without small talk, unnecessary promotion, or interview clutter—shaped with music and space for reflection.

Episodes cover entrepreneurship, leadership, business strategy, growth, marketing, finance and investment, AI and technology, personal development, and the realities of building and leading businesses.

Episodes

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

08 September 2026

#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...

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

#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,...

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

#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...

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

#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...

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

#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 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...

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

#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 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?

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?

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...

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

#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 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...

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

#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 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...