Go Big Once: The Mindset Behind Building Generational Wealth with John Pennington

Most entrepreneurs try to scale by working harder. John Pennington scaled by changing the structure.

In this episode of The $100M Entrepreneur Podcast, Brad Sugars sits down with John Pennington — a 14-time entrepreneur who built a fund platform that snowballed into $28B in assets under management, 1,000 employees across 33 states, and a New York Stock Exchange listing.

They break down what actually makes growth “unstoppable”: why a fund structure scales when most businesses stall and how to recruit people who are smarter than you by offering ownership instead of a paycheck. John also explains the real mechanics of raising capital — from high-net-worth investors to institutions — and why you must become “institution-ready” before they take you seriously.

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About John Pennington:
John Pennington is a serial entrepreneur and fund builder who has started 14 businesses and learned the hard way why most companies struggle to scale. His breakthrough came through building a general partnership / limited partnership fund platform across multiple asset classes — from real estate lending to multifamily, senior living, office, and industrial — ultimately helping grow a firm to $28B AUM and a public listing. He’s known for pairing structure with elite talent, using equity to attract high-level partners, and playing the long game to raise institutional capital.

About Brad Sugars
Internationally known as one of the most influential entrepreneurs, Brad Sugars is a bestselling author, keynote speaker, and the #1 business coach in the world. Over the course of his 30-year career as an entrepreneur, Brad has become the CEO of 9+ companies and is the owner of the multimillion-dollar franchise ActionCOACH®. As a husband and father of five, Brad is equally as passionate about his family as he is about business. That’s why, Brad is a strong advocate for building a business that works without you – so you can spend more time doing what really matters to you. Over the years of starting, scaling and selling many businesses, Brad has earned his fair share of scars. Being an entrepreneur is not an easy road. But if you can learn from those who have gone before you, it becomes a lot easier than going at it alone.

Please click here to learn more about Brad Sugars: https://bradsugars.com/

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