21st Century Entrepreneurship

Joe Prencipe is an attorney who began his career at a leading international law firm and has worked on more than $100 billion in transactions, and we spoke about the costly legal mistakes entrepreneurs make when their businesses reach $1 million in annual revenue. Having represented billionaires and growing startups, Joe explains why founders often bring their "minor league habits into the major league" when negotiating multimillion-dollar contracts, raising capital, or facing litigation. Joe...

Gal Vered is the co-founder and CEO of Checksum, a former Google product leader and Israeli Navy veteran who began his technology career building machine-learning systems for maritime security, and we spoke about delegating daily work to AI agents and making AI-generated software reliable enough to ship. His frustration with software bugs, combined with Google's rigorous but time-consuming testing processes, led him to rethink how applications should be verified. As AI dramatically accelerate...

Joe Downs is a self-storage investor, developer, educator, and former residential real-estate investor, and we spoke about why he moved into a market where more than 70% of facilities are still owned by mom-and-pop operators. His turning point came when he discovered that the industry was far less institutional than he had assumed: “80% of the industry is mom and pop” at the time he entered around 2016. For Joe, that fragmentation meant opportunity—especially for investors frustrated by the r...

Alexandre Mongeon is a CEO and co-founder of Vision Marine Technologies. Alex has been building electric boats since 2013, and we spoke about what it takes to turn a technology people doubt into something they can actually trust and use. Electric boats spent generations associated with slow trolling speeds, but Alexandre says his team reached 116 mph in 2023, while cutting maintenance by about 90%. On operating cost, his comparison is even sharper: roughly $5 of electricity for a full day ver...

Latané Conant is a four-time CMO, author, community builder, and Chief Market Officer at Parloa, and we spoke about why companies spend heavily trying to understand customers while often making it harder for those same customers to talk to them. After having “spent millions of dollars… trying to understand customers,” she realized nine months ago that another part of many businesses was effectively doing the opposite. Her approach to AI-driven customer experience starts with a simple principl...

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...

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...

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...

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...

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...

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 ...

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...

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...

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 building. Their response was to help artists become more visible, commercially valuable and entrepr...

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 across 2023 and 2024. Looking back, Scott says the difference between entrepreneurship as a “beau...

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 piece of my brain.” He later built a 250-person mentoring operation that worked one-on-one with a mil...

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 entrepreneurs who struggle to access traditional venture capital. Rather than positioning community investi...

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 establish principles for making their own financial decisions. After a decade in the financial in...

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 first-round job interview at most firms because it’s not trustworthy.” Ryan explains that AI has a ...

Chris Majer is a former University of Washington rugby captain, performance psychologist, and organizational consultant, and we spoke about how practice, mood, and coordination determine whether growing companies can actually transform. An airport-bookstore encounter with George Leonard’s The Ultimate Athlete led him from rugby into Aikido, sports psychology, and work with elite athletes, Olympic teams, and Special Forces. That path eventually took his methods into business, where a 48-month ...

Simon Mach is a crypto trader and founder of MyCryptoParadise, and we spoke about how a lean operation that began with four traders survived repeated market cycles after launching in 2016. When meme-coin bets that worked during bull markets vanished in a downturn, Simon stopped chasing potential 1,000% gains and developed a professional approach guided by one hierarchy: “Capital protection first, consistency second, and growth third.” He explains why professionals calculate potential losses b...

Xavier Rivera is a former U.S. Marine, trader, and financial education mentor, and we spoke about turning a $200 teenage investment into $20,000—then borrowing $60,000, losing most of it, and spending four years trapped in debt. At 17, he entered the military believing his basic needs would be covered while he learned the markets, but the failed pharmaceutical trade pushed him so far into pressure that, as he says, “I was so deep in survival mode.” During a nine-month deployment aboard the US...

Timothy Dougherty is a fitness entrepreneur and franchisor, founder and CEO of Project LeanNation, and we spoke about rebuilding identity after poverty, financial success, federal prison, and the collapse of everything he had tied his value to. The gym was the first place “where pain had purpose,” and keeping a small promise—to arrive at 6:00 each morning—gave him evidence that he could become disciplined. Years later, despite the house, Porsche, boat, and growing family, he says, “I never fe...

Mike Stone is President & CEO of CertaPro Painters®, and we spoke about building scalable businesses through trust, proven systems, technology, and values. After more than 26 years with the organization, Mike believes sustainable growth comes from moving beyond individual projects toward long-term relationships because “projects end,” while strong customer relationships endure. Mike explained how franchising lets entrepreneurs be “in business for yourself, not by yourself,” combining inde...

Andy Harris is a former three-time CEO and current President of North American Strategies and Managing Director with STS Capital, and we spoke about how founders can prepare their companies for an exit that delivers more than standard market value. After completing more than 20 acquisitions and six exits, Andy learned M&A by “being in the shoes” of business owners—building companies, managing daily operations, and preparing them for strategic buyers. His central advice is to remove “found...

Sam Rosenberg is a former Marine officer and close-protection specialist, and we spoke about how ordinary people can recognize danger, avoid freezing under pressure, and protect those they love. After safeguarding prominent public figures, he concluded that “it’s good to have a lifeguard, but ultimately you should know how to swim”—meaning people should learn the same foundational thinking skills used by professional protectors. His turning point came before the Marines, when a man pointed a ...

Yana Carstens is the founder and executive coach of Realign and Thrive, and we spoke about why she believes burnout is not caused simply by working too much. After experiencing severe stress herself—including a visit to the emergency room—she began examining the deeper patterns that keep founders and leaders operating under constant internal pressure. She defines burnout as a “lack of vibrancy”: losing the ability to feel present, grounded, and engaged in work that once mattered. Yana’s frame...

Dr Peter Kevorkian is a chiropractor, educator, international speaker, and President of Life Chiropractic College West. We spoke about why he believes chiropractic care belongs in proactive health, not only crisis care. He argues that more people are moving away from waiting for pain, illness, or breakdown before caring for the body, and toward asking how they can become healthier, stronger, and more adaptive. He explains chiropractic through the spine and nervous system, but not as an isolat...

Peter Murphy is the CEO and co-founder of Pocket Prep, and we spoke about how failing the same certification exam twice by one point became the starting point for a 15-year software business. A former aerospace employee, Peter was trying to advance his career through a difficult supply-chain credential when he scored 299 twice on a test that required 300 to pass. That moment changed his view of preparation: “I was never taught how to study.” The method that finally worked was not reading more...

Reza Rahman is the co-founder of AVA Finance, and we spoke about why so many American households are drowning in debt, financial stress, and credit confusion. He started the company six years ago with two co-founders after seeing two problems: consumer debt growing toward $18 trillion, and a financial system that “was not built for humans.” The turning point was recognizing that most people are expected to manage credit, interest, cash flow, fees, and debt without the tools that businesses ta...

David Liddle is a conflict resolution expert, culture adviser, author, and founder who has spent 25 years helping organizations move from toxic teams and formal grievances toward healthier, higher-performing workplaces—and we spoke about why culture is not “words on a wall,” but the operating system behind scale, growth, and performance. David explains that many workplace problems leaders lose sleep over are not really strategy or finance problems, but behavior problems: people not listening,...

Frederick Fisher is a 51-year insurance professional, author, educator, and expert witness, and we spoke about why insurance often fails at the exact moment people expect it to work. He explains why claims-made policies can be “very, very, very dangerous,” and why the real insurance product is not the policy document but the way a claim is handled when something goes wrong. The turning point in this conversation is Frederick’s argument that the claims department should not be treated as a cos...

Todd M. Villarrubia is a 30-year tax attorney, estate planning expert, and exit planning advisor, and we spoke about how high-income entrepreneurs can reduce taxes, protect assets, and plan wealth before a sale, lawsuit, divorce, or death forces the issue. His focus is simple: entrepreneurs spend years building wealth, but as they grow, “the protection of that wealth becomes even more important.” Todd explains why old estate plans often break as wealth increases, why some entrepreneurs should...

Miriam Schulman is the author of Artpreneur, founder of the Artist Incubator program, and a longtime artist and business coach, and we spoke about how creatives can build profitable businesses without underpricing, chasing social media, or waiting to feel ready. After starting on Wall Street and changing direction after 9/11, Miriam realized she was not living her purpose and began applying “time tested strategies for selling” to her own portraits. Her approach centers on pricing, belief, emo...

Ferdinand Mehlinger is a search technologist and founder @ G-Stacker who says his background goes back to Backrub, the early project that became Google, and we spoke about why small business owners struggle to be found online without spending heavily on ads. He explains that most plumbers, landscapers, doctors, architects, and local operators do not have time to study SEO after work, and that many owners simply admit, “I don’t know any of this.” The turning point came when a friend told him t...

Saahil Mehta is a business owner, mountaineer, and coach, and we spoke about redefining success after realizing that the version he had been chasing was not truly his. By 36, he had grown his net worth fivefold, built businesses across two continents, owned the Porsche, the villa, and the lifestyle—yet still felt hollow. The turning point came after a near-fatal car crash and his wife telling him she “doesn’t recognize me anymore.” Saahil explains how he created his “seven summits” framework:...

Evan Marks, Founder @ M1 Performance Group, is a former Wall Street hedge fund professional and mental performance coach, and we spoke about how high performers make better decisions under pressure instead of simply reacting. After 25 years on Wall Street, Evan now coaches traders, portfolio managers, CEOs, entrepreneurs and athletes, including NASCAR drivers, on what separates the best from the mediocre: “High performers know how to consciously respond,” while “the rest just react.” His turn...

Dr. Irena O'Brien is a cognitive neuroscientist and founder of the neuroscience school, and we spoke about how the brain shapes change, leadership, energy, and performance before we are even consciously aware of it. Her work helps coaches and helping professionals understand why “the brain's first job is survival” and why change often fails when we treat it only as mindset, motivation, or willpower. Irena explains the brain as a prediction engine: it uses past experience to estimate whether s...

Zack Tomlin is a former founder who spent 12 years building and exiting a business, and we spoke about why most business advice doesn’t actually work for individual leaders. He’s also the author of Craft: The Expedition of Business, a book he repeatedly referenced throughout the conversation as a practical guide to mastering decision-making, leadership, and the craft of business. His core argument is simple: most advice is built for an “average business,” but “most businesses aren’t your aver...

Guffy Wright is a risk advisor and sales leader at The Mahoney Group, working with entrepreneurs and large companies in scale mode. We spoke about how to make high-stakes decisions when millions are on the line. His work sits at the intersection of insurance, strategy, and human behavior—helping leaders think beyond price and into consequences, especially “on their worst day” and their best. A turning point in his career came from repeatedly seeing deals stall even when the value was obvious....

Dave Munson is the founder of a global leather goods company Saddleback Leather Co., and we spoke about how he built it from nothing, nearly lost it multiple times, and ultimately learned how to run a healthy, profitable business. His journey includes sleeping on the floor in Mexico, being stolen from “millions of dollars several times,” and almost going out of business—experiences that forced him to rethink everything about leadership and operations. A major turning point came when a mentor ...

Alec Broadfoot is founder and CEO of VisionSpark and author of Hiring Your Right #2 Leader. We spoke about why most entrepreneurs fail to hire the right number two—and how to fix it using data instead of gut instinct. His turning point came after building a profitable company with great service but disastrous hiring results, where “we were actually firing about 7 out of 10 people.” Everything changed when he adopted structured assessments and flipped those results, proving that hiring isn’t i...

Jon Ostenson is a franchise consultant and former corporate executive, and we spoke about how people can enter business ownership without a “million-dollar idea” by leveraging franchising—especially beyond fast food. After years in corporate, he “always had the desire to build my own empire instead of someone else’s,” but lacked a clear starting point. His turning point came when he discovered non-food franchising and later led a franchise system, where he saw how ordinary people could succee...

Dr. John Scott is a former astrophysicist turned serial entrepreneur, and we spoke about why most innovation fails—and how to systematically flip those odds. After earning dual PhDs and spending over a decade in academia, he walked away from a tenured position after realizing that entrepreneurs “were having a lot more fun and satisfaction… than me writing equations on a blackboard.” That turning point led him to build and test a new model for creating companies—one designed not around ideas, ...

Rob Braiman is a serial entrepreneur who has built 10 companies and advised thousands of business owners, and we spoke about why most businesses plateau—and how to break through those ceilings. Over 30+ years, he’s seen the same pattern repeat: founders start strong, but growth stalls as they remain the bottleneck, “wearing too many hats” and keeping control instead of building real leadership structures. His approach centers on four pillars: revenue generation, organizational design, process...

Nate Amidon is a former United States Air Force officer, former C-17 pilot, and CEO of Form 100 Consulting, and we spoke about why many companies execute well at small scale but begin to fail once complexity increases. His core argument is simple: a great idea is not enough—“if you have a great business idea, but you can't execute on your great business idea, then it doesn't really matter.” Drawing directly from military operations, he explains why scaling a startup after funding often resemb...

Brett Penager is an entrepreneur, former wrestling coach at Olympic level, and co-builder of a multistate healthcare business that grew beyond $100 million, and we spoke about what it actually takes to fail repeatedly, learn precisely, and eventually build something measurable at scale. His story starts unusually early: in sixth grade, after hearing Earl Nightingale ask, “Why do people become who they become?”, he decided he wanted to own a business, serve millions, and create extraordinary f...

Peter Holtz is a CPA and certified tax planner with nearly 40 years of experience, and we spoke about why most entrepreneurs misunderstand taxes, profits, and the real role a financial advisor should play in growing wealth. Rather than acting as what he calls “box fillers,” accountants who simply submit returns, Peter focuses on helping business owners understand their numbers and build what he calls a business wealth cycle — a repeatable system for turning profits into long-term financial se...

Julie Wilson is a Canadian family physician and healthcare entrepreneur, and we spoke about how she built one of the largest primary care groups in British Columbia by redesigning work itself to eliminate burnout instead of accepting it as inevitable. During the pandemic, when clinics were closing and healthcare workers were overwhelmed, she saw an opportunity to rethink the system—creating workplaces where flexibility, autonomy, and culture became growth drivers rather than perks. As she exp...

Bo Jacob is a CPA, investor, and entrepreneur, and we spoke about his book Unstuck Economics: How Ordinary People Turn Smart Hustles into Real Wealth and the practical path to financial freedom in a world where the old career blueprint no longer works. He argues that many people feel trapped because “the blueprint that we saw a long time ago… has changed,” with unstable careers, rising costs, and fewer traditional safety nets—but also more opportunity than ever to build income independently. ...