The Happy Hustle Podcast

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caryjack3@gmail.com

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10 Areas Every Entrepreneur Must Master, The S.O.U.L.M.A.P.P.I.N. System with Cary Jack & Serial Entrepreneur, Founder of Speakeasy Mastermind, Eric Berman

August 25, 2026

Have you ever hit every single goal you set out for yourself and still felt completely empty inside? That's the exact moment I found myself in years ago, staring at a stack of investor paperwork worth millions, and I couldn't sign it. I was recently interviewed by Eric Berman on Inside The Speakeasy. It was a great experience! We discuss my journey from extreme burnout to creating a life centered around freedom, fulfillment, and intentional success. Inside The Speakeasy, hosted by Eric Berman...

The SHOCKING Truth About Selling Your Business, Hike & Pod from the Montana Mastermind with Strategic Business Advisor Michael Sauer

August 21, 2026

Have you ever built something you love, poured years into it, and never once stopped to ask what it's actually worth? Most business owners haven't. And that one blind spot could cost them everything they worked for. In this episode of The Happy Hustle Podcast, I sit down with Michael Sauer also known as Bone, an exit planning expert who has helped guide business transactions up to a hundred and twenty million dollars. He works with business owners to figure out exactly what their company is w...

The 3 Mountains of Life: Turn Entrepreneurs' Pain Into Purpose and Impact with International Speaker and Best-Selling Author Philip McKernan

August 18, 2026

Have you ever caught yourself repeating a story about your life that, if you're really honest, isn't even true anymore? Maybe it's the "I had a perfect childhood" story, or the "I love my business" story, or the "I just don't know what I want to do" story. We tell ourselves these things so often we forget to check if they're real. That's exactly where this conversation with Philip McKernan took me, and honestly, it wrecked me in the best way. In this episode of The Happy Hustle Podcast, I sit...