Coaching with Jay: Leadership Through Stages

Jay Bacrania, growth consultant at Crews & co., returns for another session of "Coaching with Jay," this time focusing on how leadership has to change as a company grows. Jay and Dave discuss unique ability, flow state, and the personal calendar exercise that helps founders see what fills them up versus what drains them. They talk through the crossroads every owner hits when the company starts to outgrow its leader, including whether to stay the right size, grind through, grow into the next seat, or bring in someone else. Jay also covers the shift from operator to leader and when to hire people who know more than you.  Links: Jay's LinkedIn: https://www.linkedin.com/in/jaybacrania/ Jay's Email: [email protected]  

Mike Wystrach is the founder of Freshly, the ready-made meal delivery company he launched in 2015 and sold to Nestlé for US$1.5 billion five years later. In this episode, he shares his journey from growing up in an entrepreneurial family on a cattle ranch in southern Arizona to starting Freshly. He and Dave discuss what it takes to scale a physical food business fast, how Freshly hit a US$8 million run rate in five months, and the exhaustion that eventually compelled him to sell. They also cover his current work at PetFolk, his US$75 million consumer VC fund Cutting Horse, and how he thinks about evaluating founders. In his view, grit and coachability are more vital than product and market size. Related Links: Mike's Website: https://mikewystrach.com/ Mike's LinkedIn: https://www.linkedin.com/in/michaelwystrach Mike's Instagram: https://www.instagram.com/mikewystrach/?hl=en  

Ethan King is an entrepreneur, AI advisor, and author of " Done: Let AI Do Your Work So You Can Live Your Life." In this episode, he returns to the show for a mid-2026 update on where AI actually stands for business owners. He and Dave dig into why most entrepreneurs are still stuck at the chatbot level, what it looks like when AI stops answering questions and starts completing tasks, and how Ethan published 12 blog posts in 40 seconds without a word of generic slop. They also get into the anti-AI backlash, the stark contrast with how China is approaching it, its impact on jobs, and Ethan's six levels of AI autonomy, a framework for honestly assessing where you are and what to tackle next.  Related Links: Ethan's Website: https://ethanking.com/ Ethan's Book: https://donebook.ai/  

Gorm Tuxen is a Danish-born entrepreneur and author of "Immigrant Entrepreneurship in America." In this episode, he shares his journey from arriving in the U.S. in 1982 to founding the Tuxen Group, a holding company spanning tech, security, parking, and transportation. He and Dave explore what makes immigrant entrepreneurs disproportionately successful, including the statistic that nearly 50 percent of billion-dollar U.S. tech companies are founded by foreign-born founders, and dig into the mindset advantages that come from starting with nothing in an unfamiliar country. They also discuss the "American dream" then and now, the immigration system, and why Gorm is still more focused on building than on selling. Related Links: Gorm's LinkedIn: https://www.linkedin.com/in/gorm-tuxen-784a767b Tuxen Group: https://www.tuxen.com/ Immigrant Entrepreneurship in America: https://a.co/d/0bodEKGj  

With the Tour de France coming up in July, Tyler Hamilton's story remains relevant. Tyler is a former professional cyclist who competed at the sport's highest levels — from the Olympics to the Tour de France — throughout his extensive career. Tyler joins the podcast to discuss his book The Secret Race and his involvement in the doping culture that surrounded professional cycling.  Related Links: The Secret Race: Inside the Hidden World of the Tour de France: https://amz.run/5dYQ Adventure Base Camps: https://www.adventurebasecamps.com/

Kimberly Moffit is an international relationship expert and the founder of KMA Therapy, one of Canada's premier psychological care clinics. Over the last 14 years, she has scaled KMA into a multi-location practice while amassing over 1.5 million social media followers and 70 million views on her YouTube channel. In this episode, Kimberly talks about her research on entrepreneurial isolation, the psychological realities of carrying a team, and how founders can leverage consumer empathy to unlock rapid growth on social media. Links: KMA Therapy: https://www.kmatherapy.com/ Kimberly's Instagram: https://www.instagram.com/kmatherapy/ Kimberly's YouTube: https://www.youtube.com/c/kmatherapytoronto Kimberly's LinkTree: https://linktr.ee/kma_therapy

Jay Bacrania returns to another session of "Coaching with Jay," this time focusing on common founder challenges. In this episode, Jay and Dave discuss feeling "stuck" — from stalled growth and constant business chaos to feeling trapped or bored even when things look good externally. Jay frames stuckness as both external (markets, leads, team, execution) and internal (feelings, body cues, and the "talk tracks" and stories in your head), arguing that mindset and narrative often shape outcomes. They discuss role clarity, delegation, and how leaders can outgrow their role as their companies scale. Jay shares a practical "dump and sort" approach — writing everything down, identifying a starting thread, building a simple story, and then ultimately planning to create momentum. Links: Jay's LinkedIn: https://www.linkedin.com/in/jaybacrania/ Jay's Email: [email protected]  

In this the second part of the wellness series, Dave interviews his trainer Craig Huntington, a strength coach for more than three decades, about why the fitness industry promotes fads and why "smart, consistent training" beats complicated programs. Craig explains his shift away from high-volume training after overuse pain, crediting Mike Mentzer's approach that emphasizes short, high-intensity workouts taken to failure. They debate the merits of endurance sports and strength training, discuss exercise safety, and cover practical travel workouts that rely on slow, controlled bodyweight movements.  Links: Craig's Website: https://b2htotalfitness.com/ Craig's Instagram: https://www.instagram.com/cdhunting/  

Gershon Ben Keren is a fifth degree black belt in Krav Maga, an academic criminologist, and former close protection professional. In this episode, Gershon shares how growing up in violent 1980's Glasgow and working club doors in the U.K. helped shape his understanding of real-world chaos. He focuses on the importance of predicting and avoiding violence, especially in a real world setting. He also explains de-escalation techniques, practical scenarios, distance management, and when to fight or run away.  Links: Gershon's Website: https://www.gershonbenkeren.com/ Krav Maga Yashir Boston: https://www.bostonkravmaga.com/  

Todd Hauptli is the President and CEO of the American Association of Airport Executives, the field's largest professional organization. Beyond his impressive career in aviation leadership, Todd has become a remarkable example of what radical commitment to personal fitness can do for your body and your business. In the first episode of Dave's two-part series on fitness, Todd opens up about his extraordinary health journey, including racking up over 12,400 Peloton rides and slashing his metabolic age by more than a decade. Todd emphasizes that a healthier body sharpens your thinking, steadies your nerves, and makes you a better leader.  Links: Todd's Linkedin: https://www.linkedin.com/in/todd-hauptli-00133a52 American Association of Airport Executives: https://aaae.org