Coach as Entrepreneur

You became a coach because you're great with people. Craig Fortune says that's not enough, and he learned it the hard way. Craig is an executive and productivity coach and the founder of ProMind Solutions in New Zealand. Before coaching he ran a multi-million-dollar business for twelve years until COVID forced him to liquidate it, and he burned out and was diagnosed with depression while that busi...

Bill Bryant spent 40 years leading teams across 8 countries and 6 industries. Then a corporate restructure ended that life and he had to build something new from zero. Bill is an executive and career-transition coach (TQ® certified, ICF ACC) who turned his own "lifequake" into a framework he now uses with clients. In this conversation he and David get honest about the part of coaching nobody warns...

What does a former naval officer who helped build Yahoo Mail learn about leadership once he becomes a psychologist to CEOs? Dr. Jonathan Marshall has lived several lives. A transposed phone number on his CV left him jobless in Silicon Valley, and he talked his way into the startup that became Yahoo Mail. Then he went to grad school instead of cashing out, earned a PhD at Stanford and a postdoc at...

What happens when a 20-year IBM veteran and former CIO graduates from the corporate world and becomes an executive coach? Jane Williams spent 20 years at IBM and was inside the building when Watson was first being trained, back when every professional had to teach the machine their own domain by hand. She rose to CIO, then built a coaching practice for IT leaders. In this conversation she makes th...

"My success as a leader is measured by how far my team members go." Urs Koenig is a Swiss executive coach, NATO and UN peacekeeper, ultra-endurance athlete, and author of Radical Humility. He has worked with leaders at Amazon, Microsoft, and Starbucks. In this episode, Urs takes us through one of the most unusual coaching journeys you will hear on this show. A geographer with a PhD in climate rese...

"If your employees are hearing feedback for the first time at the annual review, way too late." Dr. Lani Jones is a clinical psychologist turned executive coach and founder of HBL Advisory Group. She helps ambitious leaders stop chasing conventional success and start architecting a lasting legacy through her Final 1% framework. In this episode, Dr. Jones brings her deep understanding of human beha...

Laurie Hollinger didn't plan on becoming a coach. She planned on fashion. Growing up in a town of 900 in North Dakota, she told her mother she was going to live somewhere she could actually touch the clothes in the magazines. She got to New York. She got recruited into the Saks Fifth Avenue training program. And she became a designer sportswear buyer. What followed was 15 years in corporate and an...

Your brain doesn't want you to succeed. It wants you to survive. David Edmonds explains why that difference is the thing keeping coaches stuck. David Edmonds is an ontological leadership coach and author of Becoming You . After 20+ years in architecture, he took a 75% pay cut to coach full-time. He now works with leaders and executives who sense they've outgrown the identity that made them success...

In this episode, we sit down with Rob Ott, former co-founder of a global pharmaceutical powerhouse that scaled from zero to over 5,000 employees. Today, Rob is an executive coach helping leaders navigate a rapidly changing world, where AI isn't just a tool—it's shifting the very fabric of leadership and management. We dive into Rob’s entrepreneurial journey, the hard truths he learned about himsel...

Fiona Siseman spent seven years at Spotify mapping the coaching culture for an organization that scaled from 3,000 to over 10,000 employees. Then, she walked away to build a private coaching partnership, Frank and Eddie Leadership. In this episode, Fiona shares the real story of transitioning from the safety of a global tech brand into the messy reality of entrepreneurship—the financial alignment,...

Lukasz Kalinowski spent two decades in the casino industry, climbing from croupier to General Manager overseeing hundred-million-dollar operations. His military reconnaissance background taught him to make fast decisions under pressure - a skill that served him well in casinos, and now serves the senior leaders he coaches through high-stakes transitions. In his first year of full-time coaching, Lu...

Most businesses have never stopped to ask where they're actually going. David Campbell has spent 20+ years helping them find out. David is a former naval officer turned business coach who calls himself the "navigation expert." After a cancer diagnosis forced him to confront his own purpose, he built an entire coaching framework around the metaphor of a sailing ship — purpose as the keel, values as...

Marcia Reynolds was coaching before the ICF had a single competency published. She joined Coach U in 1995, became the ICF's 5th President, and has since built a globally recognized coaching practice spanning 47 countries and six books. In this episode, David sits down with Marcia to unpack the real challenges coaches face — chief among them, the shock of realising they've just started a business,...

Alexandra Popkova is a PCC with 15 years of experience leading organizational development across NGOs, startups, and major corporations. In this episode, she breaks down the pragmatic side of building a coaching business. Coaching isn't just about service delivery; it’s about business administration, networking, and authentic visibility. Alexandra shares her tactical approach to building credibili...

 If you've ever felt like you're "too much" for the corporate world—too loud, too direct, too emotional—this episode is for you. Darren Kanthal explains how he turned his "Achilles heel" into his greatest asset as a coach. Plus, we get tactical on how to network without looking desperate and why "listening" is the most underrated sales tool in your arsenal. Key Takeaways: The "Sandbox" Moment: How...

"You aren't married to being right. You're married to your client being successful." Tami Reiss (aka "Tami from Miami") brings high energy and deep product expertise to the world of executive coaching. In this episode, Tami breaks down exactly how she transitioned from corporate product management to a high-ticket coaching business. We dive deep into why most coaches struggle to scale because they...

What if the secret to executive performance was hidden in a 100-year-old educational philosophy? Regina Sweeney joins us to discuss integrating Montessori principles into high-stakes leadership. Regina Sweeney is an executive coach who uses Montessori’s observations on human development to help leaders solve modern business problems like overwhelm, lack of creativity, and terminal distraction. In...

She was a VP managing a $25M division and 350 staff. Then she found coaching. Amy Minor Fletcher is a certified executive coach holding a PCC credential, helping professionals navigate "Career 2.0" by integrating work, life, and self-care. In this episode, we explore Amy’s leap from high-level corporate leadership into the world of coaching. We discuss the critical differences between therapy, men...

From shop floor mechanic to President of major aerospace companies, Kurt Richardson knows exactly what it takes to bridge the gap between technical expert and true leader. With 40+ years of experience at giants like Boeing and Spirit, Kurt now uses his "systems, strategy, and heart" approach to coach executives on navigating the complexities of leadership. In this episode, Kurt reveals why so many...

Jeremiah Teo (Hong Kong-based Charisma Business Coach) joins Coach as Entrepreneur to talk about what it really takes to build confident, influential leadership. We dig into credibility, imposter syndrome, client selection, and the systems behind a sustainable coaching business. IN THIS EPISODE: Building credibility early (proof, reps, testimonials) Why imposter syndrome doesn’t disappear with exp...

Jim Fielding knows what it's like to go from running teams at global brands to learning how to tie his shoes again as a solo entrepreneur. After three decades at Disney, Dreamworks, and the Clippers, Jim launched his coaching practice and had to build every system from scratch. In this episode, Jim shares his journey from overwhelmed beginner to confident business owner, including the tools he use...

After 24 years in the Navy and 14 more as a government contractor, Les Britt discovered his true calling: coaching others to build lives of purpose and legacy. In this episode of Coach as Entrepreneur, Les shares his journey from military service to entrepreneurial freedom, and how he helps clients transform through three core pillars: vision, mindset, and strategy. We dive into: How coaching foun...

What You'll Discover in This Episode: Ever wonder what it takes to leave a prestigious legal career at Morgan Stanley and build a thriving coaching business from scratch? Annelise Pesa pulls back the curtain on her decade-long journey as an executive and leadership coach, sharing the raw truth about what it really takes to succeed as a coach entrepreneur. In this conversation, Annelise gets refres...

Most coaches struggle to scale because they don't think like entrepreneurs. Nicole Greer is different. As the CEO of Build A Vibrant Culture, she's built a thriving practice by combining coaching, training, and speaking—each feeding into the other. In this episode, she shares her business-building playbook: the tools that matter (Zoom, Basecamp, High Level), the programs leaders actually need, and...

Your zone of excellence is killing your coaching practice. David Taylor-Klaus explains why spending time doing things you're great at, but that aren't your genius, cheats both you and your clients. In this conversation, we unpack the systems that free coaches from busywork: four-hour monthly content creation, AI tools that extend your coaching capacity, and why your website should be a disqualific...