Coach as Entrepreneur

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 the ribs, mission as the planking.In this episode, David Chung and David Campbell talk about the early days of coaching (when you had to explain what a coach even was), why sales is the hardest part of coaching, how to build a LinkedIn-only visibility strategy, and why the question "where are you going?" is the most powerful one a coach can ask.Key themes: Purpose-driven coaching | LinkedIn strategy | Sales for coaches | Visibility vs. marketing | Client selection | Building communityConnect with David Campbell: LinkedIn: https://www.linkedin.com/in/david-campbell-business-coach/Website: https://david-campbell.com GYM Program: https://gymevents.com.auReady to close the Growth Gap? Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5postAbout Coach as Entrepreneur: Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Connect with David: Website: https://kyberfive.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

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, not just a coaching practice. Marcia is direct: if you're not willing to sell, market, and show up consistently, your coaching career won't last.They also dig into why AI is actually a *gift* to coaches (not a threat), how to leverage your corporate past instead of running from it, and what Marcia updated in the second edition of her landmark book *Coach the Person, Not the Problem* to address the age of AI and the crisis of human connection.**Key themes:** Building a coaching business | Identity shifts | Niche & visibility | AI vs. human coaching | Purpose-driven entrepreneurship🔗 Connect with Marcia Reynolds 🌐 Website: https://outsmartyourbrain.com 🌐 Website: https://covisioning.com/ 💼 LinkedIn: https://www.linkedin.com/in/marciareynolds/📖 Get the Book Coach the Person, Not the Problem (2nd Edition) — available on Amazon and major online bookstores, or visit https://covisioning.com/coach-the-person-not-the-problem-2nd-edition/Ready to close the Growth Gap? Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5postAbout Coach as Entrepreneur: Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Connect with David: Website: https://kyberfive.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

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 credibility, managing imposter syndrome, and her current transition from a solo practitioner to a scalable business owner.Key Takeaways:The Portfolio Strategy: Why "strict selection" of free clients is better than random free work.Curiosity over Bias: How to step back from your own triggers to serve clients better.The Gender Lens: Observed differences in how executives seek help and portray confidence.The Scale Transition: Moving from "doing everything" to focusing on the Zone of Genius.🔗 Connect with Alexandra:LinkedIn: https://www.linkedin.com/in/alexandrapopkova/Instagram: https://www.instagram.com/empower_leaders/Website: https://alexandrapopkova.com🔗 Connect with David & KyberFive:Website: https://kyberfive.comLinkedIn: https://www.linkedin.com/in/davidchung-01/

 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 one question from his coach changed Darren's entire career trajectory.The "Double-Sided Coin" of Entrepreneurship: Why total freedom also means total responsibility (and how to handle the pressure).Networking 101: Why asking for "clients" kills the conversation, and why asking for "introductions" saves it.Checking Emotions: Why the old-school corporate advice of suppressing emotions is actually destroying leadership performance.Connect with Darren:LinkedIn: https://www.linkedin.com/in/darrenkanthal/Website: https://thekanthalgroup.com/Ready to close the Growth Gap?Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5postABOUT COACH AS ENTREPRENEUR:Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Subscribe for new episodes every week.CONNECT WITH DAVID:Website: https://kyberfive.comLinkedIn: https://www.linkedin.com/in/davidchung-01/

"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 are "waffling instead of winning," and how she iterated her way from hourly consulting to a simplified $10,000 package. We also explore the "Rule of Thirds" for business health and why influence is the only currency that matters in an AI-driven world.Key Topics:- The "Niche Advantage": Why "a product for everyone is a product for no one"- Productizing Coaching: Moving from complex menus to a set $10k offer- "Deputizing" vs. Delegating: Creating true ownership in teams- The "Just Not Sorry" Story: How a side project became a viral career-maker- Influence Without Authority: The core skill for modern leadersConnect with Tami Reiss:Website: https://tamireiss.comLinkedIn: https://www.linkedin.com/in/tamireiss/Ready to close the Growth Gap?Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5postABOUT COACH AS ENTREPRENEUR:Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Subscribe for new episodes every week.CONNECT WITH DAVID:Website: https://kyberfive.comLinkedIn: https://www.linkedin.com/in/davidchung-01/

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 this episode, Regina and David discuss why most executives lose over two months of their year to task-switching and how to reclaim that time through "Freedom within Limits." They dive into the "GPA mindset" that keeps coaches terrified of mistakes, and why "Friendliness to Error" is actually the key to innovation. Regina also shares her journey of homeschooling nine children while building a business, and why coaches must embrace being entrepreneurs—not just practitioners.Key Topics:Focus vs. Concentration: Why time management isn't enough for deep work.The 40-second distraction trap and how it wastes 2+ months of your year.Friendliness to Error: Replacing fear of mistakes with faster prototyping.Freedom within Limits: Setting the heuristics that prevent "shiny object syndrome."Onstage/Backstage/Offstage: A simple framework for organizing your week as a coach.Attracting clients through psychographics vs. demographics.Connect with Regina: Website: reginasweeney.com Check out her hidden Spotify Playlists and current cohort at reginasweeney.com/cohort.Ready to close the Growth Gap? Get the Growth Gap resources here: growthgap.kyberfive.com/?ref=k5postABOUT COACH AS ENTREPRENEUR: Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.CONNECT WITH DAVID: Website: kyberfive.com LinkedIn: linkedin.com/in/davidchung-01/

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, mentoring, and coaching, and why Amy believes coaching is 80% muscle building (mental fitness) and 20% insight.If you are a coach struggling with the "visibility" hurdle or an executive trying to balance high-stakes leadership with family caretaking, this conversation provides a clear framework for moving forward with purpose.Key Topics:Moving from VP to Coach: The transition and "aha moments"Psychology vs. Coaching: Why the future matters more than the pastThe "Amplify" Framework: Accountability, Mindset, and PurposePositive Intelligence: Identifying and disarming your internal saboteurs"Anything worth doing is worth doing poorly until you get good at it"The visibility struggle: Why even top VPs shy away from marketingPractical tips for executive caregivers in the "sandwich generation"Connect with Amy:Website: https://www.amplifyyourjourney.com/ LinkedIn: https://www.linkedin.com/in/amy-minor-fletcher-amf-pcc-08a18311/ Ready to close the Growth Gap? Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5postABOUT COACH AS ENTREPRENEUR: Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.CONNECT WITH DAVID: Website: https://kyberfive.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

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 organizations fail to develop their leaders and how "accidental managers" can take control of their own growth. He breaks down actionable frameworks like "Above the Line" thinking, the power of removing apologies from your vocabulary, and how to use open-ended questions to transform both your business and personal relationships.Key Topics:- Transitioning from subject matter expert to executive leader- The "Above the Line" vs. "Below the Line" accountability framework- Practical tools: 5-Second Rule, Radical Candor, and stopping apologies- Why "hire slow, fire quicker" still requires investing in your people- Building a high-impact coaching practice in retirementConnect with Kurt:LinkedIn: https://www.linkedin.com/in/kurt-richardson-mba-07850615/Ready to close the Growth Gap?Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5postABOUT COACH AS ENTREPRENEUR:Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Subscribe for new episodes every week.CONNECT WITH DAVID:Website: https://kyberfive.comLinkedIn: https://www.linkedin.com/in/davidchung-01/

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 experienceClient fit: who to say “no” to (and why)Jeremiah’s approach to chemistry calls vs intake formsScaling lessons: why a lean team can outperform “going big”AI tools in coaching: using them to improve reflection and questionsCharisma as self-acceptance + serviceCONNECT WITH JEREMIAH:LinkedIn: https://www.linkedin.com/in/jeremiah-teo-charisma-business-coachWebsite: https://www.ctsolutionsglobal.com/charisma-acceleratorNEED HELP WITH YOUR COACHING BUSINESS OPERATIONS?If you're struggling with the backend of your coaching business (client management, scheduling, systems, and automation) check out CoachOps: https://kyberfive.com/coachops/ABOUT COACH AS ENTREPRENEUR:Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Subscribe for new episodes every week.CONNECT WITH DAVID:Website: https://kyberfive.comLinkedIn: https://www.linkedin.com/in/davidchung-01/

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 uses, the mistakes he made, and the mantra that guides his coaching: leave your corner of the world a little better than you found it.Key Topics:Transitioning from corporate executive to solo coachBuilding systems through trial and error (calendars, invoicing, graphics, content)Going from 4 hours/day on LinkedIn to 25 minutesWhy humility is your competitive advantage as an entrepreneurThe business development challenge coaches faceWorking with global freelance teamsAdding value through small, incremental changesConnect with Jim Fielding: LinkedIn: https://www.linkedin.com/in/jimfielding/ Website: https://www.hijimfielding.com/ABOUT COACH AS ENTREPRENEUR: Coach as Entrepreneur is the show for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, each episode features honest conversations with coaches about the realities of building a sustainable coaching practice.Subscribe for new episodes every week.CONNECT WITH DAVID: Website: https://kyberfive.comLinkedIn: https://www.linkedin.com/in/davidchung-01/

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 found him (and why every coach needs a coach)Overcoming introversion to build a coaching businessThe power of "getting comfortable being uncomfortable"Why failure isn't fatal—it's part of the processHow one client's transformation brought them both to tearsWhy he caps his roster at 12 clients to prioritize family and freedomBuilding a coaching practice through relationships, not just social mediaWhether you're a coach building your business or someone exploring what coaching can do, this conversation will challenge how you think about success, legacy, and what it means to truly serve others.CONNECT WITH LES BRITT: Website: https://lesliebritt.net/ LinkedIn: https://www.linkedin.com/in/leslie-les-britt-0b88557/NEED HELP WITH YOUR COACHING BUSINESS OPERATIONS?If you're struggling with the backend of your coaching business—client management, scheduling, systems, and automation—visit https://kyberfive.com/coachops/We help coaches build the systems that let you focus on what you do best: coaching.ABOUT COACH AS ENTREPRENEUR: This show is for coaches building real businesses with systems, strategy, and heart. Hosted by David Chung, we explore what it takes to serve clients, build a sustainable practice, and support your family—without sacrificing what matters most.

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:Why lawyers desperately need coaching and how toxic "prove yourself" cultures are driving talented professionals out of the industry—plus the specific leadership gaps that coaching fills when law school doesn't teach you how to actually lead peopleThe chemistry session framework that actually converts including why Annelise shifted from offering 90-minute sessions to focused 30-minute consultations, and how meeting clients "where they are" emotionally makes all the difference in closing dealsHow to build authority through publication and why being a regular contributor to multiple industry publications creates a compounding visibility effect that brings clients to you (even when individual articles don't convert immediately)The brutal truth about "everyone and their mom" becoming a coach and why Annelise predicts most new coaches will fall away—plus what separates those who build sustainable businesses from those who give upTreating coaching as a real business with systems and discipline including the specific tools Annelise uses (like Capsule CRM), why she compares marketing coaches to personal trainers, and how she structures her time when there's no boss telling her what to doThis 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 Coaching00:28 Meet Annise Pezo: Executive and Leadership Coach02:01 From Law to Coaching: Annise's Journey04:46 The Importance of Leadership in Law Firms07:33 Effective Coaching Strategies11:00 Building a Coaching Business16:05 Challenges and Realities of Running a Coaching Business22:45 The Value of Coaching and Meat Analogy23:19 The Importance of Writing and Authenticity24:58 Building Visibility and Trust27:19 Challenges and Rewards of Running a Coaching Business30:57 Advice for New Coaches39:44 Overcoming Difficult Times and Writing a Book43:00 Future Plans and ConclusionCONNECT 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.comLinkedIn: https://www.linkedin.com/in/davidchung-01/🔔 Subscribe for weekly episodes with coaches who are actually doing the work and building profitable businesses.#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 GreerCEO, Training, Recruiting, Coaching, Speaking and ConsultingAs 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.comWebsite: www.vibrantculture.comCoachOps 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.comLinkedIn: 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/id1843243824Spotify: https://open.spotify.com/show/0hpKBTpaHH5qT1mzilKRu6Amazon Music: https://music.amazon.com/podcasts/98fa3ba9-56dc-4eb3-989f-d890ab21bf02ABOUT 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.comLinkedIn: 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:The transition from tech entrepreneur to full-time coachThe "bridge moment" that changed everythingWhy you can't coach half a personSelling vs. enrolling: the difference that makes or breaks your practiceBuilding systems that create ease (not just efficiency)Why celebration accelerates growthValues as your lens for decision-makingThe acceleration point in every coaching engagementABOUT 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.comLinkedIn: 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 HastingsHarry 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:Why confidence unlocks matter more than achieving specific goalsHis unconventional business model: 10-person monthly cohorts + 4 CEO clients per yearThe 4-pillar marketing system that built his practice without sleazy tacticsWhy he invested in a post-production team and overseas VAs while keeping tools simpleHis best advice for new coaches: hire a journalist (not a marketer) to tell your storyFor coaches building sustainable practices that honor both clients and family, Phil offers a masterclass in intentional business design.About Phil Hayes-St.ClairPhil 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.comLinkedin: https://www.linkedin.com/in/philhsc/

When Leaders Can't Lead: The Courage Crisis in Education with Phil RobertsWhat 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:Why courage and vision matter more than any strategic frameworkThe hidden cost of altruistic leadership (and why it's unsustainable)How to coach the whole person, not just their professional capabilitiesWhy DISC and EQ assessments reveal what strategy sessions never willThe reality of building a coaching practice at different life stagesWhen to address personal imbalance before tackling strategic gapsPhil 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 AccidentWhat 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:The pivotal moment Eileen became a coach (before certifications, before clients, before feeling "ready")Why self-awareness is a leader's most powerful tool – and how the Enneagram reveals itThe critical difference between coaching, advising, consulting, and facilitating (and where Eileen found her sweet spot)Her "serve more, sell less" philosophy and why coaching isn't a "maybe" – it's hell yes or hell noWhat separates six-figure coaches from those making under $40K (hint: it's about value, not volume)How to structure group coaching programs that create transformation and communityWhy she never coaches anyone she doesn't like and respect – and how that one-hour chemistry session protects both coach and clientThe difference between success, milestones, and achievement (and why confusing them keeps leaders stuck)How to build a coaching practice around lifestyle first, income second – and still serve at the highest levelWhether 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:Website: https://onecreativeview.com/LinkedIn: https://www.linkedin.com/in/eileenrogers/Resources Mentioned in This Episode:The Prosperous Coach by Steve Chandler and Rich LitvinThe Gifts of Imperfection by Brené Brown (used in her forum programs)Dare to Lead™ by Brené BrownThe Enneagram (Integrative Enneagram approach)

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:The "queue at my office" story that led him to discover coaching as a leadership toolThe financial reality of coaching vs. corporate (and why he still chose it)His "abundance mindset" approach - he always presents clients with 2-3 coach options, including his competitorsThe 12-month rule - why you need a full year of financial runway before starting a coaching businessThe identity shift - what it feels like to go from Fortune 500 recognition to "Sam who?"The number one struggle for new managers - why technically excellent people fail at leadership (and how coaching helps)His collaborative business model - how he built a network of coach partners for referrals and large projectsHard truths for aspiring coaches - including why younger coaches struggle to serve senior executives in Asian marketsThe difference between coaching friends and real clients - and why you need paying customers to develop your skillsWhy he turned down scaling opportunities - choosing one-on-one depth over group programs and maximum incomeThis 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