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 refreshingly honest about the early misconceptions she had—thinking clients would just show up once she hung out her shingle. Spoiler alert: they didn't. She walks us through the mindset shifts, business investments, and strategic decisions that transformed her from struggling solopreneur to sought-after executive coach working with legal professionals across multiple continents.
Here's what you'll learn:
This isn't motivational fluff. It's a practical masterclass in building a coaching business that serves high-level clients while maintaining your authenticity and avoiding burnout.
CHAPTER TIMESTAMPS:
00:00 Introduction: The Missing Element in Coaching
00:28 Meet Annise Pezo: Executive and Leadership Coach
02:01 From Law to Coaching: Annise's Journey
04:46 The Importance of Leadership in Law Firms
07:33 Effective Coaching Strategies
11:00 Building a Coaching Business
16:05 Challenges and Realities of Running a Coaching Business
22:45 The Value of Coaching and Meat Analogy
23:19 The Importance of Writing and Authenticity
24:58 Building Visibility and Trust
27:19 Challenges and Rewards of Running a Coaching Business
30:57 Advice for New Coaches
39:44 Overcoming Difficult Times and Writing a Book
43:00 Future Plans and Conclusion
CONNECT WITH ANNELISE PESA:
🌐 Website: https://www.annelisepesa.com/
🔗 Linktree: https://linktr.ee/annelisepesa
💼 LinkedIn: https://www.linkedin.com/in/annelisepesa/
Annelise Pesa is a Senior Executive & Team Coach (PCC/ICF) and former international finance lawyer who spent nearly a decade at Morgan Stanley. She specializes in empowering legal professionals and senior executives to unlock their unique strengths through a holistic approach that integrates positive psychology, NLP, and stress management.
ABOUT COACH AS ENTREPRENEUR:
Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, we explore what it actually takes to build a sustainable coaching practice, from client enrollment to systems that scale.
Connect with David Chung:
Website: https://kyberfive.com
LinkedIn: https://www.linkedin.com/in/davidchung-01/
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#coachingbusiness #executivecoaching #leadershipdevelopment #CoachEntrepreneur #LegalCoaching #businesscoaching #coachingforlawyers #BuildACoachingBusiness #icfcoach #entrepreneurmindset #coachingcareer #professionaldevelopment #leadershipskills #CoachingSystems #solopreneurlife
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 why focusing on people—not products—is the only way to create lasting organizational change.
Nicole Greer
CEO, Training, Recruiting, Coaching, Speaking and Consulting
As CEO of Build a Vibrant CultureTM, Nicole Greer helps individuals, corporations, government, and non-profits become leaders who fulfill a mission, energize their teams, and build a vibrant culture. Using the S.H.I.N.E.
Coaching MethodologyTM and training programs, Nicole offers foundational tools and uncommon wisdom.
Email: Nicole@vibrantculture.com
Website: www.vibrantculture.com
CoachOps by Kyber Five:
If you’re a coach trying to get more consistent clients and you want to see how the CoachOps system works, here’s the link: https://kyberfive.com/coachops/
ABOUT THE SHOW:
Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, we explore what it actually takes to build a sustainable coaching practice—from client enrollment to systems that scale.
Subscribe for new episodes every week.
Connect with David Chung:
Website: https://kyberfive.com
LinkedIn: https://www.linkedin.com/in/davidchung-01/
#CoachingBusiness #EntrepreneurCoaching #BusinessSystems #CoachAsEntrepreneur #LeadershipCoaching #ExecutiveCoaching #CoachingPractice #EntrepreneurMindset
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 disqualification tool, not a lead magnet. Plus, the networking framework that builds practices through relationships, not funnels. This is systems thinking for coaches who want to scale without burning out.
QUICK NOTE: The audio quality on this episode isn't what we'd usually release. This was supposed to be our first episode, but I held it back, hoping to fix the sound. Eventually, I realized the conversation is too valuable to keep on the shelf. Thanks for your patience.
ABOUT DAVID TAYLOR-KLAUS:
David Taylor-Klaus, MCC, is a Master Certified Coach who reintroduces successful entrepreneurs and senior executives to their families. After 30+ years as a serial entrepreneur—including co-founding and running an internet strategy company for 14 years—David experienced his own wake-up call standing on the proverbial bridge, wondering how he got so lost despite outward success.
Now in his third decade of entrepreneurship and 17+ years as a professional coach, David helps his clients create the kind of life rhythm that enables them to build profitable businesses, raise thriving families, and live wildly fulfilling lives. He combines candor, intelligence, and humor with masterful coaching to challenge leaders to reach their highest levels of performance both professionally and personally.
David has lived with ADHD and depression for most of his life, giving him a deep understanding of and compassion for the neurodivergence common among entrepreneurs and maverick leaders. His bestselling book, Mindset Mondays with DTK: 52 Ways to Rewire Your Thinking and Transform Your Life, is available on Amazon.
Connect with David:
Website: https://dtkcoaching.com/
LinkedIn: https://www.linkedin.com/in/davidtaylorklaus/
Find us on your favorite podcast apps:
Apple Podcasts: https://podcasts.apple.com/podcast/coach-as-entrepreneur/id1843243824
Spotify: https://open.spotify.com/show/0hpKBTpaHH5qT1mzilKRu6
Amazon Music: https://music.amazon.com/podcasts/98fa3ba9-56dc-4eb3-989f-d890ab21bf02
ABOUT THE SHOW:
Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, we explore what it actually takes to build a sustainable coaching practice—from client enrollment to systems that scale.
Subscribe for new episodes every week.
Connect with David Chung:
Website: https://kyberfive.com
LinkedIn: https://www.linkedin.com/in/davidchung-01/
#CoachingBusiness #EntrepreneurCoaching #BusinessSystems #CoachAsEntrepreneur #LeadershipCoaching #ExecutiveCoaching #CoachingPractice #EntrepreneurMindset
Want to hit six figures as a coach? David Taylor-Klaus did it in 10 months.
In this episode, he breaks down the difference between selling and enrolling, why "life coaching vs. business coaching" is a false choice, and the exact systems that scale a coaching practice profitably. From celebration practices that accelerate results to the question "what will this look like when it's easy?" that transforms how you build, David shares frameworks that work.
QUICK NOTE: The audio quality on this episode isn't what we'd normally release. This was supposed to be our first episode, but I held it back hoping to fix the sound. Eventually I realized—the conversation is too valuable to keep on the shelf. Thanks for your patience.
KEY TOPICS:
ABOUT DAVID TAYLOR-KLAUS:
David Taylor-Klaus, MCC, is a Master Certified Coach who reintroduces successful entrepreneurs and senior executives to their families. After 30+ years as a serial entrepreneur—including co-founding and running an internet strategy company for 14 years—David experienced his own wake-up call standing on the proverbial bridge, wondering how he got so lost despite outward success.
Now in his third decade of entrepreneurship and 17+ years as a professional coach, David helps his clients create the kind of life rhythm that enables them to build profitable businesses, raise thriving families, and live wildly fulfilling lives. He combines candor, intelligence, and humor with masterful coaching to challenge leaders to reach their highest levels of performance both professionally and personally.
His bestselling book, Mindset Mondays with DTK: 52 Ways to Rewire Your Thinking and Transform Your Life, is available on Amazon.
Connect with David:
Website: https://dtkcoaching.com/
LinkedIn: https://www.linkedin.com/in/davidtaylorklaus/
ABOUT THE SHOW:
Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, we explore what it actually takes to build a sustainable coaching practice—from client enrollment to systems that scale.
Subscribe for new episodes every week.
Connect with David Chung:
Website: https://kyberfive.com
LinkedIn: https://www.linkedin.com/in/davidchung-01/
Harry Hastings didn't just leave a 33-year career in education—he built something entirely new. After decades of leading schools and mentoring educators, Harry made the bold decision to launch The Sherpa, an executive coaching practice dedicated to helping leaders navigate their most challenging transitions with clarity, confidence, and purpose.
In this candid conversation, Harry shares the real story behind his first year as an entrepreneur. From landing his first paying client (a former student) to building a practice of 30+ active clients across diverse industries, Harry opens up about what actually works—and what doesn't—when building a coaching business from the ground up.
We explore the philosophy behind The Sherpa name and why the metaphor of a mountain guide perfectly captures Harry's coaching approach: support, challenge, and guidance delivered with wisdom earned from decades in the trenches of leadership. Harry shares powerful stories from his work, including how he supports head teachers navigating school closures, helps young professionals discover their values and direction, and coaches executives across venture capital, real estate, and beyond.
You'll hear Harry's honest take on the challenges of irregular income, the discipline required to constantly "sow while you harvest," and why LinkedIn became his most valuable client acquisition tool. He breaks down the difference between coaching and mentoring (a distinction many potential clients don't understand), explains his values-driven coaching methodology, and shares the beautiful client testimonial that coaching is like "pumping up your tires"—you can't complete your journey on flat tires.
But perhaps most powerfully, Harry offers one word of advice for every coach starting out: enjoy. In a world that glorifies hustle and overwork, Harry reminds us that if you're your own boss, you need to actually be your own boss—which means protecting your well-being, setting boundaries, and remembering that "enough" is a complete sentence.
Whether you're launching your coaching practice, scaling to your next level, or simply curious about what it takes to make a major career transition successful, this episode offers both tactical strategies and profound wisdom you won't want to miss.
About Harry Hastings
Harry Hastings is a Level 7 ILM Executive Coach and founder of The Sherpa, an executive coaching practice specializing in leadership development and transformational change. After 33 years in education—including distinguished Headteacher roles at Ardingly and Brighton College Prep Schools—Harry made the transition into full-time coaching in 2024.
Since launching The Sherpa in September 2024, Harry has accumulated over 300 coaching hours and currently works with 30+ active clients spanning multiple sectors, including education, venture capital, executive search, real estate, and luxury travel. He is also pursuing his ACC (Associate Certified Coach) certification through the International Coach Federation (ICF).
Harry's coaching philosophy centers on three core pillars: support, challenge, and guide. Drawing from his extensive leadership experience and his Level 7 ILM training (facilitated by Love Your Coaching), Harry helps clients clarify their values, navigate high-stakes transitions, build confidence without arrogance, and create sustainable success in both their professional and personal lives.
His client roster includes senior executives, head teachers, emerging leaders, and even former students—now in their 30s and 40s—who return to work with Harry in what he calls "chapter two" of their relationship. Harry is known for his values-driven approach, his emphasis on accountability and action, and his ability to create safe spaces where leaders can be vulnerable, process difficult emotions, and discover their own solutions.
When he's not coaching, Harry enjoys walking in the Sussex woods with his dog (where he first conceived The Sherpa name), playing golf (though not as often as he'd like), and continuously learning from his own network of coaches and mentors.
Connect with Harry:
📧 Email: harry@thesherpa.pro
🌐 Website: www.thesherpa.pro
Phil Hayes-St.Clair sat in a military hospital chair, breaking out in full-body sweat as the doctor delivered devastating news: his dream of becoming an Australian Army pilot was over. With zero Plan B and his entire identity wrapped up in that goal, Phil entered what he calls the "spin cycle"—trying to figure out what comes next when everything you planned is ripped away.
Twenty years later, Phil uses that experience—and lessons from building 8 companies—to help CEOs and founders navigate their own profound transitions. His approach? Start with the end: "How do you want to be remembered?" Then work backwards.
In this episode, Phil reveals:
For coaches building sustainable practices that honor both clients and family, Phil offers a masterclass in intentional business design.
About Phil Hayes-St.Clair
Phil Hayes-St.Clair coaches CEOs who are winning externally but losing internally. After building eight companies over 20 years, he learned the hard way: your business can't grow faster than you can.
His unconventional journey—from aspiring Australian Army pilot to triathlon team member to serial entrepreneur—shaped his approach to helping leaders scale themselves, not just their businesses.
Phil works with CEOs through one-to-one coaching and runs The Partnership Lab, a 6-week program where clients close six-figure deals within 60 days. His clients achieve 5–20% revenue growth while getting their lives back.
Host of Partnership Playbook podcast.
Connect: philsc.com | hello@philhsc.com
Linkedin: https://www.linkedin.com/in/philhsc/
When Leaders Can't Lead: The Courage Crisis in Education with Phil Roberts
What happens when the most dedicated leaders become their own worst enemies?
After 21 years as a principal and 30+ years in educational leadership, Phil Roberts has seen it all from transforming failing schools into thriving communities to coaching drowning executives back to shore. Now, as an ICF-accredited coach and consultant to Australia's independent and Jewish education sectors, Phil reveals the uncomfortable truth about leadership that no one talks about.
In this raw conversation, Phil shares the story of a Melbourne school leader who's sacrificing everything family, health, and ironically, his ability to lead—in pursuit of serving others. It's a pattern Phil sees repeatedly: the most altruistic leaders often need the most help.
Key Takeaways:
Phil drops truth bombs about the coaching industry itself, including the stark difference between knowledge and wisdom, why life experience trumps certifications, and the years-long journey to land C-suite clients. His advice to aspiring coaches? "Buy your time. Don't rush into being a 20-something coach unless you've got real experience to draw on."
Whether you're a coach working with educational leaders, an executive struggling with work-life balance, or someone considering the leap into coaching, this episode delivers hard-won insights from the intersection of leadership, education, and personal transformation.
The conversation peaks when David challenges the notion of compartmentalized coaching: "You can't just coach half of somebody. If you're gonna coach them, you have to coach the whole person." Phil's response will change how you think about leadership development forever.
Building a Coaching Business with Intention – Not by Accident
What does it really take to build a coaching business that creates deep impact without desperate selling? And how do you design a practice around the life you want – not just the income you need?
In this episode, David sits down with Eileen Rogers, a former CEO who built and sold a multimillion-dollar marketing company after 40 years before transitioning into executive coaching. Eileen is one of only 500 people worldwide trained by Brené Brown to facilitate Dare to Lead™, and she uses the Enneagram alongside her decades of leadership experience to help executives transform from armored to courageous leadership.
This conversation goes deep into the realities of building a coaching business, the good, the challenging, and the intentional choices that separate thriving coaches from struggling ones.
In this episode, you'll discover:
Whether you're just starting your coaching journey or refining an established practice, Eileen's wisdom on building with intention, serving from abundance, and creating sustainable impact will shift how you think about your business.
About Eileen Rogers:
Eileen Rogers built and sold a marketing company after 40 years before founding One Creative View, where she works as a leadership coach and advisor. She's one of only 500 people worldwide trained by Brené Brown to facilitate Dare to Lead™ and is a Certified Enneagram Practitioner. Eileen coaches executives, facilitates yearlong women's leadership forums, and supports leaders in creating transformational shifts.
A recipient of the ATHENA Award, Golden Heart of Business Award, and named a Top 30 Businesswoman by Phoenix Business Journal, Eileen has served in board leadership roles for the Arizona Humane Society, The YMCA, Homeward Bound, Planned Parenthood of Arizona, and multiple chambers of commerce. She co-led US delegations to Uganda, Rwanda, Cambodia, Nepal, and South Africa through the Foundation for Global Leadership, and after a medical mission trip to Mali in 2009, she built a village school there. In 1998, she created a Baby Diaper Drive that became the Diaper Bank of Central Arizona.
Eileen is a committed lifelong learner and change agent who believes entrepreneurs don't retire – they evolve. With unbridled joy for life, she continues to travel internationally while coaching leaders who want to lead with courage, authenticity, and open hearts.
Connect with Eileen:
Resources Mentioned in This Episode:
Sam Chia spent 35 years in corporate leadership - VP roles, Fortune 500 companies, running regional businesses across Asia. He was successful by every traditional measure. Then he discovered coaching by accident.
While traveling 60-70% of the time as a regional VP, Sam noticed his team constantly queuing outside his office like patients at a clinic - waiting for him to solve their problems and approve their decisions. Frustrated by being a bottleneck, he learned coaching techniques to empower his team. The results were immediate: his team became more self-sufficient, learned faster, and stopped waiting for him to make every decision.
That experience planted a seed. But Sam didn't immediately jump into coaching. It took an acquisition that changed his organization's culture and leadership to make him realize: "In the corporate world, this is the kind of thing you have to face. Is there something I can be more in control of?"
The transition wasn't romantic. It was brutal.
Sam faced what he calls an "identity crisis" - going from having a Fortune 500 brand backing every conversation to being just "Sam." People who used to eagerly take his calls suddenly went cold. He went from high earner to zero income overnight. He had to learn functions he'd always delegated: marketing, sales, website building, funnel creation.
His first business model, running an HR consulting firm with 15 full-time consultants, taught him "the hard way" that overhead kills coaching businesses. So he pivoted to a solo model with a collaborative network of trusted coach partners.
Today, Sam runs a sustainable coaching practice that earns about 50% of his corporate income - but on his terms.
He works primarily with executives and emerging leaders in middle management and above, helping them navigate the challenging transition from individual contributor to people manager. His coaching engagements typically run 6-12 months, allowing him to see real transformation - not just training attendance.
In this episode, Sam shares:
This conversation is raw, honest, and packed with practical wisdom.
Sam doesn't sugarcoat the challenges of building a coaching business. He talks about trusting the wrong people who stole clients (who eventually came back). He discusses the cultural dynamics that make experience and shared background crucial in Asian coaching markets. He shares why some new managers discover they don't actually want to be leaders - and how that's still a successful coaching outcome.
If you're considering leaving corporate to become a coach, this episode is required listening. Sam provides a realistic roadmap that balances passion for helping people with the business fundamentals required to survive and thrive.
About Sam Chia: Sam is an ICF PCC-certified leadership coach with over 35 years of corporate leadership experience, including VP and MD roles across Fortune 500 companies, government agencies, and nonprofits. He holds an ACC, MBA, and has completed executive education at Harvard. Sam is co-author of two books on coaching in Asia and has been running his coaching practice in Singapore for over a decade.
Retry
In this episode of Coach as Entrepreneur, David sits down with Francis Strickland, a business strategist and coach who brings 30 years of global corporate HR leadership to small and mid-sized businesses. Now based in Switzerland after a remarkable career journey from South Carolina to Wisconsin and beyond, Francis shares powerful insights on what it truly means to build a coaching business with clarity and purpose.
Key Topics Covered:
- The shift from corporate coaching to entrepreneurship – How COVID-19 revealed the need for authentic leadership and sparked Francis's transition into professional coaching
- Authentic leadership vs. performative leadership – Why leaders must connect with their genuine selves rather than just executing mandates
- The harsh realities of scaling too fast – A cautionary tale about hiring corporate talent for a small business and the importance of values alignment
- What coaches really need before building a website – Why message clarity trumps professional branding in the early stages
- Selling safety, not services – How to communicate value in a way that builds trust with potential clients
- Vertical vs. horizontal development – The difference between skill-building and transformational mindset shifts for entrepreneurs
Francis offers candid advice for new coaches: get crystal clear on who you are and the impact you want to make before your first client conversation. She's currently building a community to provide straightforward, high-impact business foundations for coaches and entrepreneurs who need guidance beyond just coaching methodology.
This conversation is essential listening for any coach struggling with messaging, scaling decisions, or the transition from service provider to true business owner.
In this episode of Coach as Entrepreneur, David sits down with Mel Rosenthal—a Melbourne-based coach and mentor to founders and executives—about shifting from corporate leadership into purpose-driven coaching. Mel shares how informed curiosity, constant reflection, and simple systems create sustainable practices; why purpose can be a better north star than goals; and how relationships and reputation outcompete ads and funnels for long-term growth. We also dig into coaching the “whole person,” leading in technical environments, and building supportive peer rhythms so you don’t do this alone.
Show Notes:
Guest Bio
Mel Rosenthal is a coach, mentor, and writer based in Melbourne, Australia, who helps founders and executives navigate the messy challenges of growth and leadership. With over 4,500 coaching conversations and 15 years leading product, marketing, and innovation teams, she’s known for her “informed curiosity”—spotting patterns others miss, cutting through complexity, and challenging with care.
How to connect with Mel:
https://www.linkedin.com/in/rosenthalmelissa/
https://melissajrosenthal.com/
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