159: A Lifelong Founder Teaches Critical Lessons for New Entrepreneurs on Products, Investors, and Selling with Jonathan Siegel

159: A Lifelong Founder Teaches Critical Lessons for New Entrepreneurs on Products, Investors, and Selling with Jonathan Siegel

Jonathan Siegel has started close to a dozen different companies—some have been hugely successful, others didn't quite go as planned, and for one, he sold his shares after a falling out with his co-founders. Siegel has been a serial startup founder since he was just 12 years old. Now at 40, he has seen it all, and he's sharing his lessons—on products, investors, and selling a business—with Foundr. "It doesn't feel like a job, as much as it just feels like I'm getting paid to do something for fun," Siegel says, about his love for the entrepreneurial life. Siegel has had a knack for entrepreneurship since he was putting together and selling computers all the way back in 1989. From there, he's had a lifelong passion for creating something new every chance he got. Whether it was starting his own businesses, constantly creating new products, or building products for other people. For Siegel, entrepreneurship isn't so much a money-making exercise or a career, but a lifestyle that constantly allows him to strive forward and look into the future. "If you do something as a creative outlet, the amount of money is not the goal. And I don't believe that every entrepreneur is running around thinking about how much money they have in their accounts. I think that every entrepreneur runs around thinking, 'Hey I want to bring this thing to life. I want to create something bigger than myself. I want to see the thing that I create influence other people in the way that they work and the way that they live,'" Siegel says. This passion has helped Siegel learn many valuable lessons on his own journey, not just about himself, but about what entrepreneurship is all about. In this episode you will learn: How to turn entrepreneurship from a career to a creative outlet Understanding the difference between a startup that's successful on paper, and one that works in real life How to handle disputes between co-founders Why it's so important to understand your motivation as an entrepreneur The lifecycle of building companies that you intend to sell & so much more!

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614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

614: (Solo) Running on Fumes? Reset Your Mindset Before The Year Ends

If you’re dragging yourself toward the end of the year feeling exhausted, overwhelmed, and mentally drained, you’re not alone. This is one of the toughest stretches for founders — you’re still runni...

16 Dec 20259min

613: Why Most Beauty Brands Fail - and How to Beat The Rest | DIBS Beauty Founder

613: Why Most Beauty Brands Fail - and How to Beat The Rest | DIBS Beauty Founder

DIBS Beauty went from zero to one of America’s fastest-growing makeup brands in just four years, with founder Jeff Lee scaling the business into the mid–8 figures and landing a top spot on the Inc. ...

11 Dec 202552min

612: (Solo) Funding vs Bootstrapping - The Real Tradeoffs EVERY Founders Needs To Know

612: (Solo) Funding vs Bootstrapping - The Real Tradeoffs EVERY Founders Needs To Know

Should you raise money or bootstrap your business? It’s one of the biggest questions every founder faces — and the wrong decision can shape the entire future of your company. In this episode, I share...

9 Dec 202512min

611: From Homeless to Multi-Billionaire - His Success Habits | John Paul DeJoria

611: From Homeless to Multi-Billionaire - His Success Habits | John Paul DeJoria

John Paul DeJoria went from being homeless twice to building two global billion-dollar brands, Paul Mitchell and Patrón Tequila, using nothing but resilience, sales mastery, and a refusal to quit. ...

4 Dec 202559min

610: (Solo) The Secret to Finding Agencies That Don’t Burn You

610: (Solo) The Secret to Finding Agencies That Don’t Burn You

When you’re just starting out, the fastest way to grow isn’t automation, ads, or scaling systems — it’s doing things that don’t scale. In this episode, I share why the most successful founders — fr...

2 Dec 20259min

609: From $0 to $20M in 3 Years Selling Suppliments | Damien Fitzpatrick

609: From $0 to $20M in 3 Years Selling Suppliments | Damien Fitzpatrick

From professional rugby player to successful entrepreneur, Damien Fitzpatrick built a sports recovery brand trusted by elite athletes around the world. In this interview, Damien shares how he went...

27 Nov 20251h 4min

608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business

608: (Solo) Why Short-Term Wins Can Quietly Kill Your Business

When I first started Foundr, I made a lot of short-term decisions — and most of them hurt us more than they helped. It took years (and a few hard lessons) to understand that sustainable growth only co...

25 Nov 202510min

607: How I Built a $120M/Year Cookie Business From My Appartment | Loren Castle

607: How I Built a $120M/Year Cookie Business From My Appartment | Loren Castle

Loren Castle turned a life-threatening cancer diagnosis at 22 into the spark that built Sweet Loren’s, a $120M-a-year clean food brand now sold in over 5,000 supermarkets nationwide. In this inter...

20 Nov 202551min

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