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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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🔥 Want to Add $50k–$250k/Month to Your Coaching Business? 👉🏼 Get your FREE Demo Now: https://jointherainmakers.com/demo (Note sure if it’s for you? You’ll know in the first 2 minutes.)
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You don’t want a business that looks good on paper but feels like hell to run. I’m qualified to say this because I built one (more than once).
Seven figures, great margins, solid team.
And it nearly cost me everything that actually mattered.
My energy. My family. My freedom.
So I burned it to the ground. Just kidding, but I did sell it.
Took the lessons. Rebuilt better.
Now I help other founders avoid the same trap.
This episode breaks down what actually gets you from $100K/month and stuck...
to $250K+/month with a life you actually want to wake up to.
Here’s what we cover:
• Why most coaches plateau at $100K/month (and what to do about it) • The real shift from founder to CEO • The structural changes needed to scale without killing your lifestyle • The chessboard strategy: how to pick your piece (or leave the board entirely) • The moment I realised “being the CEO” was my biggest bottleneck • What team culture really takes (hint: it starts with how you show up) • The power of removing your own label and playing a better role • Why selling the company didn’t mean retiring... it meant choosing a better game
If you’re scaling a coaching or expert business...
And it’s starting to feel more like a prison than a pathway, This one’s for you.
And it’s the truth I wish I’d heard earlier.
Chapters: 00:00 – Why Most Coaching Businesses Become Prisons 00:35 – The Trap of “Looking Successful” but Feeling Miserable 01:30 – The $100K/Month Plateau (And What Breaks It) 02:40 – How Big Do You Actually Want to Grow? 03:25 – $250K/Month vs $1M/Month: Two Totally Different Games 04:10 – The Chessboard Analogy: Picking the Right Role 05:20 – Why I Replaced Myself as CEO 06:30 – Transcending the Chessboard: From King to Player 07:25 – Labels, Identity, and Playing a Bigger Game 08:30 – What Being a Great Leader (and Dad) Actually Requires 09:45 – Culture Starts with You: The Asana Lesson 10:50 – My Real Role as Founder: Architect and Operator 11:45 – The Cost of Too Much Freedom 12:30 – Final Thoughts: Build the Business That Serves Your Life
121 episodes
