21st Century Entrepreneurship

Zach Rapaport is the Founder and Principal of Meerkat Development, and we spoke about what it takes to transform big dreams into scalable realities. With a rich background in construction, project management, and development, Zach shared his journey from working on his father’s job sites to leading national expansion projects for global brands like Joe & the Juice. He now brings his expertise...

Scott McCrady is a seasoned cybersecurity expert and Chief Executive Officer at SolCyber Managed Security Services with decades of experience shaping security strategies for businesses of all sizes. We spoke about the evolving challenges in cybersecurity, why small and medium businesses (SMBs) are now prime targets for cyberattacks, and how to proactively embed security into your organization&apos...

Benjamin  Lightburn is a pioneer in the development of natural psychedelic drug candidates. We spoke about his groundbreaking work at Filament Health, where he and his team are redefining how psychedelics are developed and utilized in clinical settings. Benjamin shared his extensive experience in botanical extraction, the challenges of building startups, and the immense potential of psychedelics f...

Oddi Aasheim is a seasoned leader and problem-solver who has worked with organizations like Shell, Accenture, and First Human. We spoke about what true leadership looks like when there are no clear answers and how to mobilize teams to create impactful futures rather than just solve problems. Aasheim shared how most leaders get trapped in a cycle of accumulating knowledge to solve immediate issues...

Rugare Gomo is a high-performance business and leadership coach who embodies resilience and purpose. We spoke about his incredible journey—from growing up in Zimbabwe to carving out a life of freedom and leadership in Australia. His story sheds light on the courage it takes to break free from societal expectations and redefine your identity on your own terms. Rugare’s upbringing was marked by syst...

Brian Anderson is an entrepreneur who mastered the art of balancing work, family, and business growth—and we spoke about why defining your principles is the secret to sustainable success. In this episode, Brian shares his journey from humble beginnings—living in his grandmother’s garage—to building a multimillion-dollar company while staying true to his core values. He talks about the importance o...

Daniel Callahan is a renowned trial attorney with a story that exemplifies resilience, creativity, and relentless preparation. We spoke about his journey from humble beginnings—graduating near the bottom of his high school class—to becoming the "Trial Lawyer of the Year" multiple times and securing some of the largest verdicts in U.S. history. In this conversation, Daniel unpacks what it...

Matt Strippelhoff, partner and CEO of Red Hawk Technologies, is a seasoned entrepreneur, and we spoke about navigating the emotional and professional storms that come with unexpected setbacks. Matt shared how a single January morning in 2017, during a foggy drive along the Ohio River, became the defining moment of his career: "I thought I was having a panic attack for the first time in my lif...

Mike Andes is an entrepreneur who dropped out of medical school after starting college at 13 and built a lawn care empire from scratch. We spoke about the pivotal moments that shaped his journey—from a near-death experience to redefining success through systems and procedures. Mike’s story isn’t just about mowing grass—it’s about resilience, strategy, and creating value in ways that scale. Key top...

Samantha Upchurch is a passionate entrepreneur and health advocate who shared her transformative journey from poverty to building multimillion-dollar businesses. We spoke about her life-altering experiences, the five-step process she developed to achieve success, and how resilience and health play pivotal roles in sustaining it. Samantha's story began in a small Greek village, where simplicit...

Jay Tobey is an entrepreneur and founder of Northstar Recovery and Wellness who combines passion, philanthropy, and strategy to tackle one of the most pressing challenges of our time—creating a seamless continuum of care in the fragmented behavioral health industry. We spoke about his entrepreneurial journey, the cracks in the mental health and substance abuse system, and his innovative investment...

Oleg Romanov is a seasoned IT entrepreneur and AI expert based in London, with a mission to help businesses harness the transformative power of artificial intelligence. We spoke about practical ways AI can solve real business challenges, such as streamlining operations, boosting efficiency, and unlocking new growth opportunities. Oleg shared an inspiring case study from the real estate industry, w...

Lior Weinstein is a lifelong entrepreneur, founder of CTOx, and a pioneer in fractional leadership. Starting his first company at 14, Lior has since built and sold multiple tech companies. Now, as a fractional CTO and CRO, he helps businesses unlock their potential by bridging the gap between vision and execution. We spoke about the challenges CEOs face in navigating technology, the transformative...

Darius Ross is a seasoned entrepreneur with over 40 years of experience, and we spoke about navigating the global economy's seismic transitions. From the challenges posed by AI and escalating unemployment to opportunities in selling businesses strategically, this episode explores how to survive and thrive in uncertain times. Darius shared his journey of rising from the inner city of Chicago t...

Michael Stone is the leader behind one of the largest players in the North American painting industry, holding a remarkable 1% of a $60 billion market. We spoke about how CertaPro Painters has grown fivefold in its space, yet still sees massive growth potential. This conversation dives into the essence of what fuels that success—not painting, but leadership, people development, and community impac...

Nick Foy is the CEO, founder, and chief evangelist of Silverdale, a consulting company revolutionizing ERP implementations. We spoke about why most ERP projects fail, the critical mistakes businesses make, and Silverdale's innovative approach to creating successful outcomes. Nick shared that 75% of ERP projects fail to meet their objectives, a statistic that often deters companies from starti...

Brad Sugars is the #1 business coach in the world, an entrepreneur with a $2.5 billion track record, and the founder of ActionCoach, the largest business coaching franchise operating in over 80 countries. We spoke about his six-step framework for building a thriving business, the common pitfalls entrepreneurs face, and the formulaic principles behind achieving both business and personal success. A...

Charlotte Watts is a resilient entrepreneur who turned her burnout and frustration into a thriving business. We spoke about the challenges of starting and growing a company, the personal sacrifices involved, and the mindset shifts that helped her navigate adversity and build success. Charlotte’s story is a testament to perseverance. From balancing a grueling work schedule with raising four childre...

Matt Tait is on a mission to make entrepreneurship more manageable. We spoke about how adaptability, intentional leadership, and leveraging technology are key to running and growing a successful business in today’s ever-changing landscape. Drawing from his journey—from being a "recovering attorney" to leading Decimal, a tech-driven accounting company—Matt shared lessons learned from his...

Kapil Dhiman is the visionary co-founder and CEO of Quranium, a company dedicated to building the next-generation quantum-secure infrastructure for a decentralized future. In this episode, we explored the urgent need for blockchain evolution as computational threats grow and security risks increase. Kapil shares his journey from consulting at PwC to leading a team that aims to safeguard the future...

Dr. Thomas Cowan is a retired medical doctor, prolific author, and alternative health visionary who has spent over 40 years questioning the foundational principles of science, medicine, and biology. We spoke about the surprising gaps in scientific literacy, even among experts, and the profound implications of living in a world shaped by unexamined assumptions. Dr. Cowan challenges widely held beli...

Ken Lundin, Founder & CEO of RevHeat, is a seasoned sales strategist who has lived through the highs and lows of building, losing, and rebuilding companies. We spoke about the most critical mistakes CEOs and business leaders make when trying to scale their sales teams and what it takes to fix them. Ken shared insights from decades of experience, including growing a company from $2M to $78M in...

Garrett Delph is a seasoned entrepreneur and founder of Clarity Ops, a boutique consulting firm specializing in transformational breakthroughs for small and medium-sized businesses. With 25 years of experience building three international businesses and hiring over 550 employees, Garrett has mastered navigating the "messy middle" of entrepreneurship. In our conversation, we explored his...

Isaac Saul is a seasoned political journalist and founder of Tangle News. We spoke about his journey from feeling disillusioned with traditional media to building a platform designed to provide a balanced, nuanced approach to political news. Isaac’s mission is bold yet simple: to offer a space where readers can engage with perspectives from the left, right, and center on divisive issues—all in one...

Magda and Jason Schappert are a dynamic entrepreneurial couple and the founders of Moola, a groundbreaking financial tool that turns earnings into a foundation for financial freedom. From humble beginnings—crawling under houses in Florida summers and navigating life as an immigrant—to building an eight-figure business, their journey exemplifies resilience and innovation. We discussed their path to...