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The 21st Century Entrepreneurship Podcast is a 4 x Gold-Award weekly show that features interviews with cutting-edge leaders and successful entrepreneurs. We talk about the fundamentals of starting and growing a business, achieving and maintaining success, as well as the difficulties of entrepreneurship and its future. Subscribe to the 21st Century Entrepreneurship Podcast and never miss an episode, so you can stay on top of the curve and gain the knowledge you need to succeed in today's competitive landscape.
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Athena Dean Holtz is a longtime entrepreneur and publisher, and we spoke about how unprocessed trauma quietly shaped her biggest business decisions. After losing a 20-year, $3.5M company through deception, she was forced to ask, “How did that happen?”—and realized she had been leading from wounds she had never allowed to heal. She explains how optimism, workaholism, and chasing success became a form of avoidance: “I was self-medicating with work and success,” rather than grieving losses or se...
Frank Scarso, the CEO and founder of Avanza Capital Holdings, is a former Wall Street broker and a longtime financial professional. We spoke about addiction, pressure, and rebuilding a life after years in a high-stress culture. Frank spent over 20 years on Wall Street, ranking top-five at his firm, before spiraling into severe alcoholism, jail, shelters, and losing contact with his children. Anthony lived inside the same culture but as a “functioning” professional, where “we always found a re...
Jay Patel is a real estate fund manager and we spoke about why he pushes people to rethink defaulting to the stock market when planning retirement. He argues many investors want a better return with less risk, yet find real estate “too intimidating” and don’t want the “headaches of managing real estate,” especially dealing with tenants—so the real question becomes whether you can access real estate returns without becoming a full-time landlord. We also talked about what drives his approach: c...
Sam Miles is a CPA, and we spoke about how entrepreneurs can legally reduce taxes while avoiding the small, preventable mistakes that trigger IRS audits. Drawing on years of audit defense and advisory work, Sam explains why “it’s not the spending of money that makes a tax deduction, it’s the context or the story,” and why documentation—not clever tricks—is what actually protects you as the IRS gets better at AI-driven matching. We also talked about where most entrepreneurs get into trouble: u...
Chris Kille is a serial entrepreneur who exited multiple companies, and we spoke about how running everything himself nearly killed him—and why delegation changed everything. At his first exit, he was earning a few million a year but doing every job himself, until “they thought I had a stroke.” That moment forced a hard reset: if the business depends on the founder, it’s fragile, stressful, and worth far less than owners believe. We talked through the practical method he learned the hard way:...
Kate Assaraf is an economist and founder, and we spoke about how she built a seven-figure, mission-driven business through word of mouth—without paid ads, influencers, or marketplaces. Her turning question was simple and risky: could a modern business grow purely through trust and real customers? She decided to prioritize direct relationships, email lists, and selective distribution, arguing that when platforms reward “the cheapest, the fastest,” the best products lose control of their custom...
Trevor McGregor is a high-performance coach and CEO, and we spoke about why so many entrepreneurs feel burned out, misaligned, and trapped by the businesses they built. After “over 45,000 one to one coaching sessions,” Trevor has seen the same patterns repeat: founders hustling harder, short on time, and unsure what they’re even optimizing for anymore. He breaks this down into five concrete blockers to scale: limiting beliefs, no clear strategic plan, missing systems, poor time management, an...
Scott Abott is the founder and CEO of BOS-UP, a three-time bestselling author, and a former EY Entrepreneur of the Year finalist. He is a systems implementer and early-stage investor, and we spoke about why structure—not hustle alone—is what actually allows companies to grow. After decades in ERP, SAP, and Oracle environments, and after building (and overbuilding) his own ventures, Scott learned the hard way that speed without discipline creates fragility. As he put it, “Be quick, but don’t h...
Scott Kelly is a veteran venture investor and advisor, and we spoke about what it really takes to raise capital after decades on both sides of the table. With 35 years in venture, multiple exits, and billions raised, Scott has seen where founders consistently get it wrong—and what actually moves investors to say yes. At the center of his approach is preparation and relationship-building. He explains why “running your startup is a full time job and raising capital is a full time job,” and why ...
Rob May is a serial founder (five startups) and we spoke about how he went from “I did not intend to go do a fifth” startup to building a new AI company after he “stumbled upon an AI idea” he could prove out—and couldn’t ignore. He’s been focused on AI since 2015 (after exiting his first company in December 2014) and framed the current moment simply: even “10 years later… we are still just at the beginning” of what’s coming. Rob walked through the real path to his current thesis: early bets, ...
Rod Khleif is a real estate entrepreneur and educator, and we spoke about how he rebuilt after losing $50 million during the 2008–09 crash—and the mindset that allowed him to have $50 million to lose in the first place. Growing up as an immigrant with little money, Rod watched his mother quietly build wealth through real estate, which pushed him to choose that path early and scale fast. The turning point came when rapid success fed ego, followed by a brutal correction. Rod calls it “a $50 mil...
David Deane-Spread is a former military and law-enforcement leader who built a decades-long career helping organizations turn cultural dysfunction into alignment, resilience, and performance. We spoke about how he applies the same persistence that kept him “fully booked without marketing for 20 years” to transform leadership teams and entire companies. His approach centers on what he calls the ABC practice of leadership—attitudes, behaviors, and conversations—which he says are responsible for...
Jake Stahl is a psychology-trained communication strategist, NLP master practitioner, and global trainer who has coached over 10,000 people across six countries—and we spoke about how people actually make decisions. His core premise is simple: every person has two profiles, the polished public one and the internal one “that responds to fear and biases and happiness,” and only that second profile makes decisions. Jake teaches leaders, founders, and sales teams how to communicate directly to th...
Peter Maher is the U.S. expansion lead for Ovanti—recently rebranded as Flote—and we spoke about why he left a stable, well-paid role in fintech leadership to build an alternative to what he calls a “very, very broken” credit system. With 12+ years in payments, partnerships, and market launches, he brought a career’s worth of operational and commercial experience to a problem he personally lived through. Maher’s motivation is rooted in his early setbacks. A single poor decision at 19 “cost me...
Jeff Abraham is an entrepreneur who retired after selling a semiconductor engineering company, and we spoke about how he later built a sexual wellness brand by using medical credibility instead of hype. He explained that “even in healthy couples, the average man finishes in 5 minutes and 40 seconds” while “the average female takes 18 minutes,” a difference he called “the arousal gap.” Rather than compete with “197 products online—shark fin, deer antler extract,” he chose to power statisticall...
AJ Cassata is an entrepreneur who has spent more than a decade building companies using one core mechanism—outbound lead generation. We spoke about why so many founders struggle with lead flow and how, as he says, “leads are the lifeblood of your business,” yet most assume they need ads, a large audience, or influencer status to grow. His turning point was realizing that targeted outbound—“starting conversations with your target market at scale”—can outperform paid channels when done with pre...
Paul Cecil is the VP of Strategy at realpha and we spoke about how a young founder-minded strategist thinks through scale, pressure, and the role of AI in real business results. He began as a pre-med student, switched into business after realizing he “liked trading stocks a lot more,” and later worked for years without pay to learn capital formation. Joining realpha as employee number ten, he helped drive seven acquisitions, eight capital raises, and a NASDAQ listing in under three years. A k...
Bogdan Micov is a former CEO who led 700 people in Dubai before a stroke at 32 forced him to confront what he calls “how stress affects us” and how much of his success was built on pressure rather than wellbeing. We spoke about his shift from operating on cortisol to operating from calm, and the method he later developed to help high performers do the same. His approach is built on a simple chain: thinking creates emotion, emotion shapes behavior, and behavior determines results. As he puts i...
Srikar Yeruva is an engineer-turned-serial entrepreneur, and we spoke about why he believes healthcare transformation starts with respecting the problem—not throwing technology at it. After years building technical companies, exiting one to Bain Capital and selling another in smart contracts, he realized “technology doesn’t sell—solutions do.” That shift pulled him into the heart of U.S. health systems, where he learned firsthand how hospitals operate, why workflows break, and why efficiency ...
Melissa Faith Hart is a public-safety innovator with 20 years of experience, and we spoke about how personal survival, technology, and community systems shaped her mission. She began her career at Xerox helping police departments modernize, eventually co-building the first criminal e-discovery system in Colorado. As she put it, she always asked, “how can I make the system better… so that we can help victims?” A major turning point came after a brain surgery and a domestic-violence crisis that...
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21st Century Entrepreneurship is your one-stop shop ⭐️⭐️⭐️⭐️⭐️ for navigating the ever-evolving landscape of the business world. Whether you're just starting out or looking to fine-tune your existing empire, this podcast offers a treasure trove of insights.