Coach as Entrepreneur

David Chung
  • 5.0 (1)
  • ENTREPRENEURSHIP

You became a coach to help people — but no one told you how to build the business behind it. Coach as Entrepreneur is the show for coaches who want to go beyond referrals and create a real business that supports both their clients and their family. Each episode explores the systems, strategies, and stories that help coaches simplify marketing, attract the right clients, and grow sustainably, without burning out. Whether you’re just starting or looking to scale, this is your roadmap to running your coaching practice like a business… and doing it with heart. Build the system. Serve your clients. Support your family.

  1. The Productized Coach: How to Build a Scalable Business & Influence Without Authority(w/ Tami Reiss)

    1D AGO

    The Productized Coach: How to Build a Scalable Business & Influence Without Authority(w/ Tami Reiss)

    "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 leaders Connect with Tami Reiss: Website: https://tamireiss.com LinkedIn: https://www.linkedin.com/in/tamireiss/ Ready to close the Growth Gap? Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5post 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.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

    1h 4m
  2. Why You lose 2 Months a Year to Distraction (And How to Fix It)

    FEB 4

    Why You lose 2 Months a Year to Distraction (And How to Fix It)

    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=k5post 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. CONNECT WITH DAVID: Website: kyberfive.com LinkedIn: linkedin.com/in/davidchung-01/

    56 min
  3. From Corporate VP to Coach: The Truth About Starting Over

    JAN 28

    From Corporate VP to Coach: The Truth About Starting Over

    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=k5post 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. CONNECT WITH DAVID: Website: https://kyberfive.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

    1h 4m
  4. Executive Coaching for Leaders: Boeing Veteran Kurt Richardson on Building Authentic Leadership

    JAN 22

    Executive Coaching for Leaders: Boeing Veteran Kurt Richardson on Building Authentic Leadership

    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 retirement Connect 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=k5post 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.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

    1h 2m

  5. JAN 14

    Building a Coaching Business Without Burning Out

    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 + service CONNECT WITH JEREMIAH: LinkedIn: https://www.linkedin.com/in/jeremiah-teo-charisma-business-coach Website: https://www.ctsolutionsglobal.com/charisma-accelerator NEED 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.com LinkedIn: https://www.linkedin.com/in/davidchung-01/

    57 min
  6. From Disney Executive to Solo Coach: Building Systems That Actually Work

    JAN 7

    From Disney Executive to Solo Coach: Building Systems That Actually Work

    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/

    1h 3m
  7. From Military Service to Coaching Freedom: Building a Life-First Business

    12/17/2025

    From Military Service to Coaching Freedom: Building a Life-First Business

    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.

    59 min
  8. The International Lawyer Who Quit to Save Toxic Workplaces

    12/10/2025

    The International Lawyer Who Quit to Save Toxic Workplaces

    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 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.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

    45 min
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About

You became a coach to help people — but no one told you how to build the business behind it. Coach as Entrepreneur is the show for coaches who want to go beyond referrals and create a real business that supports both their clients and their family. Each episode explores the systems, strategies, and stories that help coaches simplify marketing, attract the right clients, and grow sustainably, without burning out. Whether you’re just starting or looking to scale, this is your roadmap to running your coaching practice like a business… and doing it with heart. Build the system. Serve your clients. Support your family.

Information

  • Creator
    David Chung
  • Years Active
    2025 - 2026
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © 2025 Kyber Five