21st Century Entrepreneurship
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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Frank Scarso & Anthony DeBenedictis: How do you rebuild life after rock bottom?
<p>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 reason… to go out and party,” until sobriety gave him clarity, purpose, and healthier relationships </p><p>The turning point for Frank came after...
Jay Patel: Can 11% a year fund your retirement?
<p>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.</p><p>We also talked about what drives his approach: capital preservation first, then dependable income, then legacy. Jay framed the planning problem bluntly—“do you have enough...
Sam Miles: How do you avoid IRS audits as an entrepreneur?
<p>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.</p><p>We also talked about where most entrepreneurs get into trouble: unreported 1099 income, poor documentation, and not knowing their own numbers. Sam urges business own...
Chris Kille: How did delegation save his life and business?
<p>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.</p><p>We talked through the practical method he learned the hard way: replacing yourself step by step. Chris explained why founders should offload admin first, t...
Kate Assaraf: Seven-figure growth without ads?
<p>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 customers.</p><p>Her core method was choosing community over algorithms. She explains that “customers are really, really smart” and can quickly spot “fake purchased authenticity,” which is why s...
Trevor McGregor: Why busy founders can’t scale?
<p>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.</p><p>He breaks this down into five concrete blockers to scale: limiting beliefs, no clear strategic plan, missing systems, poor time management, and weak execution. Trevor explains why “most people spend more time planning their vacation than they do their business and their li...
Scott Abbott: How systems turn chaos into scalable growth?
<p>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 hurry,” a lesson earned after raising millions, scaling too fast, and realizing how much he didn’t yet know.</p...
Scott Kelly: What actually gets a yes from investors?
<p>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.</p><p>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 shortcuts don’t work. Instead of blasting pitch decks, Scott stresses building a vetted...
Rob May: When should you stop using just one AI model?
<p>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.</p><p>Rob walked through the real path to his current thesis: early bets, being “a couple years too early” pre-LLM, and...
Rod Khleif: How did he recover after losing $50M?
<p>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.</p><p>The turning point came when rapid success fed ego, followed by a brutal correction. Rod calls it “a $50 million seminar,” and explains that recovery didn’t start with tactics, but with psychology...
