Having been through this myself a few times, I can’t help but wonder: what exactly motivates these ultra-successful people to walk away from thriving businesses and start all over again? Sure, my ventures weren’t anywhere near as successful, but I’ve definitely felt the grind—the long hours, the setbacks, the little wins, and the pure excitement of building something from scratch.
For me, the real drive came from the excitement of creating something, being imaginative, and watching it take shape, almost like stacking wooden blocks into a pyramid. Of course, my little pyramids never reached billions, and a lot of my motivation was simply creating financial security for my family. But what about someone who’s already made it big—who’s built a multimillion-dollar empire? What pushes them to walk away and start something completely new? It may sound crazy, but this happens more often than you’d think.
Entrepreneurs are wired differently. They crave growth, excitement, and innovation. The rush of a new challenge is often far more appealing than the comfort of an already successful business. So, what’s really behind the decision to leave a well-established business for something fresh? Let’s take a closer look.
I get it. I think this is something all successful entrepreneurs have in common. Once they’ve built and scaled a business, things start to feel a bit... predictable. The early excitement starts to fade, and without that constant rush, it can be hard to stay motivated.
Take Elon Musk for instance. He’s the genius behind Tesla and SpaceX, but before that, he co-founded Zip2, which he sold to Compaq for almost $300 million. Instead of taking it easy, he jumped straight into another startup, X.com, which later became PayPal. And even after PayPal was sold, Musk didn’t stop—he just kept moving forward. Whether you love him or not, he thrives on facing new challenges and pushing the boundaries of what’s possible.
Sometimes, it’s less about the business and more about what the founder is passionate about. As we grow, so do our interests. The things we were once passionate about may no longer spark that same fire, and that can push entrepreneurs to explore new opportunities or causes that align with their evolving values.
Look at Richard Branson, founder of the Virgin Group. He’s not just resting on his successes in everything from music stores to airlines. He’s now reaching for the stars—literally—through Virgin Galactic, aiming to make space travel accessible. He’s also focused on sustainability through his Virgin Earth projects. His interests continue to lead him into new, exciting areas, which keep him inspired and moving forward.
Running a business is emotionally and mentally draining, especially when you’re at the top. The stress, the long hours, the constant pressure to innovate—it can all eventually lead to burnout. For some entrepreneurs, stepping away from their current venture and starting something new is the best way to rediscover their passion.
Steve Jobs is a prime example. After being ousted from Apple, the company he founded, he didn’t retire. Instead, he started NeXT, a new computer company that was later acquired by Apple in 1997. He took time to recharge, refocus, and return to Apple with a new vision that turned the company around and led to its most innovative era.
Once financial success is achieved, many entrepreneurs start thinking about their legacy. It’s no longer just about making money—it’s about making a real difference in the world. For some, that means venturing into businesses that tackle societal issues or push the boundaries of technology.
Take Jeff Bezos. After creating and growing Amazon, he shifted his focus to Blue Origin, his space exploration company, aiming to make space travel more affordable and accessible. His desire to make a significant impact beyond e-commerce shows how a founder’s goals can evolve once they've found financial success.
This one hits close to home. When a business grows large, it can feel like you’re trapped in a web of responsibilities, bureaucracy, and endless meetings. Some founders leave their companies simply for the freedom to control their time and decisions.
Look at Mark Zuckerberg. While he’s still deeply involved with Facebook, he’s always exploring new areas, like virtual reality and the metaverse. Facebook has already established itself as a dominant player in the social media world, which gives Zuckerberg the flexibility to experiment with new ventures and shape the future of technology without worrying about his existing empire.
For many entrepreneurs, the real joy comes from the process of building—creating something new from the ground up. It’s not about the destination, but the journey itself: assembling the team, crafting a new idea, and bringing it to life.
Evan Williams, co-founder of Blogger and Twitter, is a great example. After Twitter became a global success, Williams didn’t stop. He founded Odeo, a podcasting company that eventually evolved into Twitter. His drive to create and build led him right back into the startup world after his first big success.
Once entrepreneurs achieve financial freedom, they can afford to take more risks. With a solid safety net beneath them, they’re free to explore ideas that might have seemed too risky before.
Larry Page and Sergey Brin, co-founders of Google, didn’t just sit back after creating one of the world’s most powerful tech companies. They launched Alphabet Inc., a parent company that houses experimental projects like Waymo (self-driving cars) and Verily (health science). With their financial success, they had the resources to take on bold, ambitious projects without fear of failure.
Building a business is a high-stakes, intense journey, and for many successful founders, it’s never just about reaching the top. The drive to innovate, tackle new challenges, and create something meaningful keeps them going. Whether it’s the call for new challenges, the desire for greater freedom, or the need to leave a lasting legacy, the entrepreneurial spirit doesn’t fade with success—it just evolves.
So, next time you hear about a business icon stepping away from a thriving company to chase a new idea, remember: they’re not just walking away—they’re setting out to create something even bigger. And who knows? The best idea might be the one that’s just around the corner.