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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576: (Solo) This One Trademark Mistake Nearly Killed My Business - Here's What I Learnt

576: (Solo) This One Trademark Mistake Nearly Killed My Business - Here's What I Learnt

I got sued just a few months into starting Foundr—and it nearly crushed everything I was building. In this short episode, I’m sharing the full story behind how I was forced to change the name of my...

5 Aug 20259min

575: Ty Haney on Being Ousted From Her Own Company: The Lesson's Learnt & How to Bounce Back

575: Ty Haney on Being Ousted From Her Own Company: The Lesson's Learnt & How to Bounce Back

In this episode, Ty Haney, founder of Outdoor Voices, shares how she turned her public downfall into the blueprint for an even bigger comeback—building multiple new brands and redefining how community...

1 Aug 202551min

574: He's Building a $250M+ Business That Measures Success in Lives Saved | Andrew Lacy

574: He's Building a $250M+ Business That Measures Success in Lives Saved | Andrew Lacy

In this episode, Andrew Lacy, founder of Prenuvo, shares how he went from two startup exits to building one of the fastest-growing health tech companies in the world—revolutionizing preventative healt...

25 Juli 202551min

573: Building a $74M a Year Beauty & Community Empire | Trinny Woodall

573: Building a $74M a Year Beauty & Community Empire | Trinny Woodall

In this episode, Trinny Woodall, founder of Trinny London, shares how she turned her mission to help women feel confident into a multi-million dollar global beauty brand. She reveals: • Why she fo...

18 Juli 202551min

572: (Solo) How to Build a Brand That’s Uncopyable: Even If Your Idea Gets Stolen

572: (Solo) How to Build a Brand That’s Uncopyable: Even If Your Idea Gets Stolen

Worried someone’s going to steal your business idea? You’re not alone — and you’re not powerless. In this short episode, I’m sharing exactly what to do when copycats come for your product — because...

11 Juli 202510min

571: No Funding, 104 Rejections & $411 Left in the Bank - How She made $65M+ on Flowers

571: No Funding, 104 Rejections & $411 Left in the Bank - How She made $65M+ on Flowers

In this episode, Christina Stembel, founder of Farmgirl Flowers, reveals how she built a $65M+ floral business from her dining room—with no funding, no degree, and no industry experience. She revea...

4 Juli 202542min

570: Your Toothbrush is GROSS - They Fixed it and Made MILLIONS | SURI

570: Your Toothbrush is GROSS - They Fixed it and Made MILLIONS | SURI

In this episode, Mark Rushmore and Gyve Safavi, co-founders of SURI (Sustainable Rituals), share how they turned a simple personal care item into a sustainable, design-led movement—challenging legacy ...

27 Juni 202559min

569: The Email Expert - How to Get Your Customers Attention

569: The Email Expert - How to Get Your Customers Attention

In this episode, Rytis Lauris, co-founder of Omnisend, shares how he bootstrapped a leading email and SMS marketing platform used by over 125,000 eCommerce brands worldwide. He shares: • Why most eco...

20 Juni 202548min

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