The Foundr Podcast with Nathan Chan

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


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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!
  • ...more
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