Coach as Entrepreneur

He Was Successful, Wealthy, and Burning Out. Here's What He Learned.

David Chung — Wed, 17 Jun 2026 19:54:25 +0900

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 business was still successful. Now he helps cognitive professionals escape the productivity trap.

In this conversation, Craig and I get into why most new coaches get the order backwards (business person first, coach second), the burnout numbers leaders keep ignoring, and the practical tools he uses with clients, from chronotypes to the Eisenhower Matrix to using your calendar for more than meetings. Then I reframe the part Craig finds hardest, marketing, as simply creating visibility and connecting with real people, and you can hear it click.

Key Topics:

Business person first, coach second
Why over 50% of people in Australasia reported burning out last year
The training failure behind remote work, and why AI is repeating it
"Eat the frog" vs. working with your chronotype
Finishing tasks early to build slack into the week
Being the product: the discomfort of marketing yourself
The reframe that makes marketing feel honest: create visibility, connect with real people
You can't manage time, only what you do with it

Connect with Craig Fortune: Website: https://www.promind.co.nz/

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/

Turning Career Disruption Into Your Competitive Edge | Bill Bryant

David Chung — Thu, 11 Jun 2026 19:56:26 +0900

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 you about: building the business behind it. They dig into why AI looks a lot like the dot-com boom all over again, why emerging leaders get more out of coaching than the C-suite, and the reframe that finally made marketing feel honest — you're not selling yourself, you have an obligation to tell people you can help.

Key Topics:

From chemical engineer to coach

Why emerging leaders need coaching the most

Readiness to be coached as the real predictor of success

AI and the dot-com parallel

The lifequake and the messy middle of transition

Why building the business is harder than the coaching

The mindset reframe that makes marketing bearable

One piece of advice for new coaches: protect your network

Connect with Bill:

Website: https://billbryant.com.au

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/

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

From Yahoo Mail to Coaching CEOs: A Stanford Psychologist on the Hidden Price of Success

David Chung — Thu, 04 Jun 2026 20:00:00 +0900

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 Harvard, and built a Singapore practice that sits right on the line between clinical psychology and executive coaching.

In this conversation he shares the breakthrough with an already-fired executive who broke down and realized he treated his team the way he treated himself, why the drive behind most high performers is an old insecurity that success never fills, and why he tells aspiring coaches to get real about the money before they quit their day job. He is also candid about hating marketing, coasting for years on a waiting list, and why coaching is a harder living than the gurus admit.

Connect with Dr. Jonathan Marshall at marshall.com.sg and on LinkedIn.

Coach as Entrepreneur is hosted by David Chung. New episodes every week.

CONNECT WITH DR. JONATHAN MARSHALL:
LinkedIn: https://www.linkedin.com/in/jmarshallconsulting/
Website: https://www.marshall.com.sg/

READ THE FULL ARTICLE: https://kyberfive.com/articles/jonathan-marshall-ep32

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/

🔔 Subscribe for more episodes with coaches, entrepreneurs, and leaders who are doing the work.

AI Won't Replace Leaders. It Will REVEAL Them.

David Chung — Wed, 27 May 2026 18:21:26 +0900

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 the case that AI will not replace leaders, it will reveal them, because once the mechanical work disappears the only thing left to evaluate is judgment.

We also get tactical about the business of coaching. Why selling to a boardroom beats selling to an individual. Why she caps her roster at 8 to 10 clients and runs 6 on purpose. Why the hardest part of the corporate-to-coach pivot is not the coaching, it is learning to be your own marketing department. And the one piece of advice she gives every new coach: get credentialed, and do not just hang up a shingle.

If you are a leader navigating the AI shift, or a corporate expert thinking about coaching as your next chapter, this one is for you.

CONNECT WITH JANE WILLIAMS:

LinkedIn: https://www.linkedin.com/in/janeparkerwilliams/

Website: Find Your Fire Coach (findyourfirecoach.com)

New venture: Make Working Work

READ THE FULL ARTICLE:

https://kyberfive.com/articles/judgment-is-the-moat

READY TO CLOSE THE GROWTH GAP?

Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5post

ABOUT COACH AS ENTREPRENEUR:

Subscribe for new episodes every week.

CONNECT WITH DAVID:

Website: https://kyberfive.com

LinkedIn: https://www.linkedin.com/in/davidchung-01/

Why This Executive Coach Rejoined the Military at 50 | Episode 30

David Chung — Wed, 27 May 2026 17:23:20 +0900

"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 research, an MBA, a consulting career, then a transition to coaching in 2000 when coaching was still the Wild West. Seventeen years later, at age 50, he rejoined the military and deployed as a NATO peacekeeper, then again four years after that with the UN in the Middle East. We talk about why he went back, the imposter syndrome he carried for years, the leadership factory concept, his ideal client (the arrogant jerk), and the practical advice he gives to anyone starting a coaching business today.

Key Topics:
Radical humility as a leadership framework
Rejoining the military at 50 to live the leadership world of his clients
The leadership factory: measuring success by how far your team members go
Imposter syndrome in early coaching ("who am I to coach executives?")
The two-channel marketing system: speaker bureaus and direct inbound
Why new coaches should give it away and get the reps in

Connect with Urs Koenig:
Website: https://urskoenig.com
Book: Radical Humility https://www.urskoenig.com/book

READ THE FULL ARTICLE:
https://kyberfive.com/articles/rejoined-at-fifty-urs-koenig-ep30

Ready to close the Growth Gap?
Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5post

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

Find us on your favorite podcast apps:
Apple Podcasts: https://podcasts.apple.com/podcast/coach-as-entrepreneur/id1843243824
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Amazon Music: https://music.amazon.com/podcasts/98fa3ba9-56dc-4eb3-989f-d890ab21bf02

Stop Throwing Spaghetti at the Wall: Coaching Lessons from Year 1

David Chung — Wed, 20 May 2026 17:27:21 +0900

"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 behavior to the conversation on leadership, culture, and the realities of building a coaching business. We unpack the Index Card test that exposes the true culture of any leadership team, why yearly performance reviews destroy growth, and how to escape the "minnow in the ocean" feeling when you're a new coach finding your voice.

Key Topics:
The Index Card test for revealing true company culture
Why yearly evaluations are broken and what to do instead
The "minnow in the ocean" problem for new coaches
The Final 1% framework: turning success into lasting legacy
How to spot when a "fear state" is killing creativity on your team
Year-one advice: put blinders on, keep the path narrow

Connect with Dr. Lani Jones:
Website: https://drlanijones.com
LinkedIn: https://www.linkedin.com/in/drlanijones/
Company: HBL Advisory Group

Ready to close the Growth Gap?
Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5post

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

Watch on YouTube: https://youtu.be/g7Vqn8EsUSw

How to Build Business Systems So You Can Take a 2-Week Vacation | Laurie Hollinger

David Chung — Wed, 06 May 2026 19:46:00 +0900

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 another decade-plus helping a small business scale to $10 million. Then she woke up almost 50 and thought: what's next? The answer became a coaching practice — and a 10-week mastermind called Design Your Decade.

In this episode, David and Laurie dig into what it actually takes to build a business that supports the life you want — not just the work. They cover the Design Your Decade framework (values, wheel of life, Working Genius), the three pillars every business owner needs to grow with ease (clear vision, empowered team, great systems), and the vacation litmus test for knowing whether your systems are real or just theoretical. Plus the North Star Laurie has carried since day one: better daycare pickups.

Key themes: Intentional business design | Fractional teams | Systems building | Coaching as a second act | Vision and values alignment

Connect with Laurie Hollinger:

Website: https://hollingerco.com

LinkedIn: https://www.linkedin.com/in/lauriehollinger

Ready to close the Growth Gap?

Get the Growth Gap resources here: https://growthgap.kyberfive.com/?ref=k5post

About Coach as Entrepreneur:

Connect with David:

Website: https://kyberfive.com

LinkedIn: https://www.linkedin.com/in/davidchung-01/

Why Your Brain Wants You to Stay Mediocre (And How to Fix It)

David Chung — Wed, 15 Apr 2026 20:00:00 +0900

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 successful.

In this conversation, David and I dig into the root fear that stops most coaches from charging what they're worth, putting themselves out there, and building real businesses. He shares his own journey from £350 for five sessions to premium leadership coaching, and the stories that shaped how he thinks about fear, identity, and contribution. We also talk about why money is a measure of contribution, the "Filing Cabinet Error" that keeps people living into their past, and the coaching conversation that may have shifted a Brexit negotiation.

Key Topics:

Why your brain is designed to keep you mediocre, not help you thrive
Fear vs. danger: how your imagination hijacks decision-making
The "Filing Cabinet Error" — stop filing past failures into your future
Charging what you're worth: from hourly rates to value-based pricing
Three tiers of coaching and why transformational work changes everything
Why every coach needs a coach
Book picks: The Chimp Paradox and Man's Search for Meaning

Connect with David Edmonds:
LinkedIn: https://www.linkedin.com/in/david-edmonds-31603020/
Website: https://www.certuscoaching.co.uk

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

Why Today's Business Leaders Must Become AI-Savvy

David Chung — Wed, 08 Apr 2026 20:21:19 +0900

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 himself through his first experience with executive coaching, and why he believes we are looking at the "last generation of leaders that will only manage humans." We also tackle the realities of running a coaching business, the fear of selling, and how to reframe marketing as a responsibility to help others.

Key Takeaways:
- [00:01:10] From the garage to 5,000 employees in the pharma space.
- [00:08:52] The brutal feedback that reshaped Rob’s leadership style.
- [00:33:07] Why this is the last generation of leaders to only manage humans.
- [00:47:58] How AI will expose the "lazy leader" and close the performance gap.
- [01:05:45] Reframing marketing: If you can help someone, you have a duty to let them know.

Connect with Rob Ott:
- LinkedIn: https://www.linkedin.com/in/rob-ott/
- Website: www.ottmgt.com
- Substack: The Spark of Leadership

Connect with David Chung / KyberFive:
- Website: https://kyberfive.com
- LinkedIn: https://www.linkedin.com/in/davidchungk5/
- Growth Gap Diagnostic: https://kyberfive.com/growth-gap-insights/

Coaching at Spotify: Building Systems for Scaling 10,000 People

David Chung — Wed, 01 Apr 2026 20:37:11 +0900

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, the networking systems, and why your job as a coach is to become completely redundant.

What you'll hear:

How Spotify's viral coaching culture evolved as the company rapidly scaled
Why Fiona and her partner aligned on a "survival threshold" before taking any clients
The "Gorilla Facilitation" style for influencing leadership teams without a mandate
Why "don't look real" is a trap and why you don't need a perfect website
The "System of 4" networking habit that replaces traditional hustle marketing
Why the ultimate goal of the best coaches is to not be needed anymore

Connect with Fiona Siseman:

Website: https://frankandeddy.com/
LinkedIn: https://www.linkedin.com/in/fionasiseman/

READY TO CLOSE THE GROWTH GAP? Get the Growth Gap resources here: https://kyberfive.com/growth-gap-insights/

ABOUT COACH AS ENTREPRENEUR:

Subscribe for new episodes every week.

CONNECT WITH DAVID:

Website: https://kyberfive.com

LinkedIn: https://www.linkedin.com/in/davidchung-01/

Ep 24 - Lukasz Kalinowski: From Military Recon to Resilience Architect

David Chung — Wed, 25 Mar 2026 20:30:00 +0900

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, Lukasz is learning that the hardest part isn't the coaching itself - it's building the business around it. He shares his journey of finding a niche in resilience, the marketing reality check every new coach faces, and a powerful client story that proves coaching ROI in real time. His honest take on the loneliness of C-suite leadership and why those leaders need coaches more than anyone is one of the most striking moments in the episode.

Connect with Lukasz Kalinowski:
Website: lukaszkalinowski.com
LinkedIn: Search "Lukasz Kalinowski" or "Resilience Architect"

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/

The Grand Adventure

David Chung — Wed, 18 Mar 2026 20:59:00 +0900

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.

Connect with David Campbell:
LinkedIn: https://www.linkedin.com/in/david-campbell-business-coach/
Website: https://david-campbell.com
GYM Program: https://gymevents.com.au

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/

Marcia Reynolds: From Corporate Trainer to Global Coaching Pioneer

David Chung — Wed, 11 Mar 2026 20:45:00 +0900

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=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/

The Hidden Difference Between How Male and Female Executives Ask for Help

David Chung — Wed, 04 Mar 2026 20:58:00 +0900

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.com
LinkedIn: https://www.linkedin.com/in/davidchung-01/

Why C-Suites Are Just As Dysfunctional As Everyone Else

David Chung — Wed, 25 Feb 2026 22:00:00 +0900

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=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/

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

David Chung — Wed, 18 Feb 2026 20:55:00 +0900

"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:

Subscribe for new episodes every week.

CONNECT WITH DAVID:

Website: https://kyberfive.com

LinkedIn: https://www.linkedin.com/in/davidchung-01/

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

David Chung — Wed, 04 Feb 2026 20:00:00 +0900

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/

From Corporate VP to Coach: The Truth About Starting Over

David Chung — Wed, 28 Jan 2026 17:10:22 +0900

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 past
The "Amplify" Framework: Accountability, Mindset, and Purpose
Positive 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 marketing
Practical 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/

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

David Chung — Thu, 22 Jan 2026 17:03:54 +0900

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:

Subscribe for new episodes every week.

CONNECT WITH DAVID:

Website: https://kyberfive.com

LinkedIn: https://www.linkedin.com/in/davidchung-01/

Building a Coaching Business Without Burning Out

David Chung — Wed, 14 Jan 2026 16:07:50 +0900

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 experience
Client fit: who to say “no” to (and why)
Jeremiah’s approach to chemistry calls vs intake forms
Scaling lessons: why a lean team can outperform “going big”
AI tools in coaching: using them to improve reflection and questions
Charisma 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:

Subscribe for new episodes every week.

CONNECT WITH DAVID:

Website: https://kyberfive.com

LinkedIn: https://www.linkedin.com/in/davidchung-01/

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

David Chung — Wed, 07 Jan 2026 14:52:33 +0900

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 coach
Building systems through trial and error (calendars, invoicing, graphics, content)
Going from 4 hours/day on LinkedIn to 25 minutes
Why humility is your competitive advantage as an entrepreneur
The business development challenge coaches face
Working with global freelance teams
Adding value through small, incremental changes

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

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

David Chung — Wed, 17 Dec 2025 15:24:00 +0900

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 business
The power of "getting comfortable being uncomfortable"
Why failure isn't fatal—it's part of the process
How one client's transformation brought them both to tears
Why he caps his roster at 12 clients to prioritize family and freedom
Building a coaching practice through relationships, not just social media

Whether 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.

The International Lawyer Who Quit to Save Toxic Workplaces

David Chung — Wed, 10 Dec 2025 17:25:58 +0900

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 people
The 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 deals
How 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 up
Treating 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 do

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/

🔔 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

How to Build a Profitable Coaching Business: Systems, Speaking & Culture Change with Nicole Greer

David Chung — Wed, 03 Dec 2025 16:27:18 +0900

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

Zone of Genius: Why Your Best Work Is Killing Your Practice (with David Taylor-Klaus) - PART 2

David Chung — Wed, 26 Nov 2025 16:59:38 +0900

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/

Connect with David Chung:
Website: https://kyberfive.com
LinkedIn: https://www.linkedin.com/in/davidchung-01/

#CoachingBusiness #EntrepreneurCoaching #BusinessSystems #CoachAsEntrepreneur #LeadershipCoaching #ExecutiveCoaching #CoachingPractice #EntrepreneurMindset

Enroll, Don't Sell: How David Taylor-Klaus Hit 6 Figures in 10 Months

David Chung — Wed, 19 Nov 2025 16:30:00 +0900

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 coach
The "bridge moment" that changed everything
Why you can't coach half a person
Selling vs. enrolling: the difference that makes or breaks your practice
Building systems that create ease (not just efficiency)
Why celebration accelerates growth
Values as your lens for decision-making
The acceleration point in every coaching engagement

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.

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/

From Head Teacher to 30+ Coaching Clients in One Year: Harry Hastings on Building The Sherpa

David Chung — Thu, 13 Nov 2025 09:47:02 +0900

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

Building a Coaching Business: Systems, Partnerships, and the Power of Your Story with Phil Hayes-St. Clair

David Chung — Wed, 05 Nov 2025 15:00:00 +0900

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 goals
His unconventional business model: 10-person monthly cohorts + 4 CEO clients per year
The 4-pillar marketing system that built his practice without sleazy tactics
Why he invested in a post-production team and overseas VAs while keeping tools simple
His best advice for new coaches: hire a journalist (not a marketer) to tell your story

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

David Chung — Wed, 29 Oct 2025 18:00:00 +0900

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:

Why courage and vision matter more than any strategic framework
The hidden cost of altruistic leadership (and why it's unsustainable)
How to coach the whole person, not just their professional capabilities
Why DISC and EQ assessments reveal what strategy sessions never will
The reality of building a coaching practice at different life stages
When to address personal imbalance before tackling strategic gaps

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.

How to Build a Coaching Business with Intention (Not by Accident)

David Chung — Wed, 22 Oct 2025 14:30:00 +0900

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:

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 it
The 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 no
What 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 community
Why she never coaches anyone she doesn't like and respect – and how that one-hour chemistry session protects both coach and client
The 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 level

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:

Website: https://onecreativeview.com/
LinkedIn: https://www.linkedin.com/in/eileenrogers/

Resources Mentioned in This Episode:

The Prosperous Coach by Steve Chandler and Rich Litvin
The Gifts of Imperfection by Brené Brown (used in her forum programs)
Dare to Lead™ by Brené Brown
The Enneagram (Integrative Enneagram approach)

Building a Coaching Business Without Sacrificing Your Family (or Your Sanity)

David Chung — Wed, 15 Oct 2025 13:24:52 +0900

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 tool
The 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 competitors
The 12-month rule - why you need a full year of financial runway before starting a coaching business
The 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 projects
Hard truths for aspiring coaches - including why younger coaches struggle to serve senior executives in Asian markets
The difference between coaching friends and real clients - and why you need paying customers to develop your skills
Why he turned down scaling opportunities - choosing one-on-one depth over group programs and maximum income

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

The Uncomfortable Truth About Building a Real Coaching Business

David Chung — Wed, 08 Oct 2025 10:30:00 +0900

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.

How Loss, Leadership, and Curiosity Led to Coaching with Mel Rosenthal

David Chung — Wed, 01 Oct 2025 09:20:29 +0900

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:

Purpose vs. goals: using values to steer offers and capacity
Early client acquisition without overwhelm: coffee, trust, and timing
Reflection rhythms: weekly peer coaching + journaling cadence
Coaching technical leaders: context-setting, culture, and outcomes
Designing a business you can run for years, not months

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/
https://www.52conversations.com/ - a card game that creates conversations that matter