The $100M Entrepreneur Podcast

Built a successful business… but don’t feel free?

In this episode of The $100M Entrepreneur Podcast, Brad breaks down the “Freedom Pivot” — the shift from operator to owner to investor. He explains why what got you to $1M won’t get you to $10M, how growth can quietly trap you, and why real freedom isn’t just about money — it’s about time, choice, and control. 
You’ll learn the three stages of business evolution, how to eliminate bottlenecks, and why systems × leadership create freedom, along with practical strategies for auditing your calendar, redesigning decision flow, and building an asset that’s scalable, saleable, and built for long-term wealth.

If you don’t want to own a job — you want to own an asset — this episode will show you how to make the shift.
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/

Build a Business That Gives You More Time, Money & Life:
Get The $100M Playbook: https://go.bradsugars.com/100m-playbook-ebook

Most companies don’t stall before $100M because of strategy — they stall because the founder can’t see the business at $100M, and the team feels that ceiling.

In this episode of The $100M Entrepreneur Podcast, Brad Sugars sits down with Jeb Blount to break down what it really takes to scale: building momentum, moving fast, and replacing “sales heroes” with a repeatable sales system (recruiting, onboarding, ramp time, comp, playbooks, and leadership). They also dig into when growth requires acquisition — and why you can’t scale chaos.

Subscribe and share this with the founder who’s still doing it all.

About Jeb Blount:
Jeb Blount is the Founder and CEO of Sales Gravy, a global sales training and coaching organization. He’s a bestselling author of 17+ books on sales and sales leadership, including Fanatical Prospecting, Sales EQ, Objections, The AI Edge, and The LinkedIn Edge. He’s also a keynote speaker and the host of the Sales Gravy podcast.
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/

Build a Business That Gives You More Time, Money & Life:
Get The $100M Playbook: https://go.bradsugars.com/100m-playbook-ebook

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.
Subscribe, share it with the operator who keeps trying to do it all, and press play.
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/

Build a Business That Gives You More Time, Money & Life:
Get The $100M Playbook: https://go.bradsugars.com/100m-playbook-ebook

In this episode of The $100M Entrepreneur podcast, Brad Sugars sits down with Sharon Lechter for a real conversation about what actually creates wealth at the highest levels—and why most business owners never get there.
This isn’t about making your next sale. It’s about building a business that works without you and becomes a true asset. Sharon breaks down why founders become the biggest bottleneck in their own companies, and how failing to plan an exit quietly caps growth, valuation, and freedom. They talk through what separates businesses that stall at a few million from those that scale to nine figures and beyond.
You’ll hear why systems matter more than personality, why intellectual property is often a company’s most valuable (and overlooked) asset, and how strategic buyers think very differently than financial buyers. Brad and Sharon dig into exits that don’t involve walking away with a check—businesses that continue producing income, impact, and legacy for generations.
If you want your business to run without you, scale past your current ceiling, and one day give you real options instead of obligations, this episode will stretch how you think.
About Sharon Lechter:  Sharon is a CPA, entrepreneur, and one of the most influential leaders in financial education. She is best known as the co-author of Rich Dad Poor Dad and for helping build the Rich Dad brand into a global powerhouse through licensing, partnerships, and intellectual property strategy. Over her career, Sharon has worked behind the scenes scaling multiple companies to nine figures while focusing on systems, leverage, and long-term impact. Her work centers on helping entrepreneurs create businesses that outlive them. 
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/

Build a Business That Gives You More Time, Money & Life:
Get The $100M Playbook: https://go.bradsugars.com/100m-playbook-ebook

Most entrepreneurs work harder when they should be thinking bigger.
In this episode, Brad Sugars sits down with Dan Fleyshman to break down what actually drives growth at every level — from your first million to building a $100M business. This is a no-nonsense conversation about why sales cure everything, why demand must come before structure, and why doing low-value work is one of the fastest ways to cap your growth.
They unpack the real shifts required to scale: raising capital the right way, building an ecosystem that pulls major players toward you, hiring executives who’ve already done it, and letting go of the tasks and people that can’t take you to the next level.
If you’re serious about scale — not just staying busy — this episode will challenge how you think and how you operate. Subscribe, share it with someone who says they want $100M, and press play.
About Dan Fleyshman:
Dan Fleyshman is a serial entrepreneur, angel investor, social media mogul, philanthropist, and speaker — and holds the distinction of being the youngest founder in history to take a company public. By age 23 he had sold over $15M in apparel and launched the “Who’s Your Daddy” energy drink into more than 55,000 retail stores and military bases. He later built one of the top online poker brands worldwide, co-founded the 100 Million Mastermind Experience, and has invested in 40+ companies across tech, consumer products, and media.
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/

Build a Business That Gives You More Time, Money & Life:
Get The $100M Playbook: https://go.bradsugars.com/100m-playbook-ebook