Having done this a few times myself, I still wonder: what drives these super successful people to leave thriving businesses and start all over again? Well, my businesses were nowhere near that successful, but I can relate to the grind: the effort, the excitement, the setbacks, and the little wins along the way.

For me, the motivation was the thrill of building something from scratch, being creative, and watching it grow, kind of like stacking wooden blocks into a pyramid as a kid. Of course, my pyramids never hit multibillion-dollar values, and a big part of my drive was always creating financial stability for my family. But what about a multimillion-dollar business owner who’s already reached the top? Why would they walk away from all that? It sounds crazy, right? But it happens more often than you might think.

Entrepreneurs aren’t like most people, they crave excitement, innovation, and growth. For them, the thrill of a new challenge can often be more enticing than the comfort of a successful business. So, what’s going on in the minds of these business legends when they decide to leave a thriving empire for something fresh? Let’s dive in.

They Need a New Challenge

Well, I needed it. I think this is the thing all those successful guys have in common. Once they’ve successfully built and scaled a business, they start feeling a little… routine. The energy that drove the first few years can fade, and without that constant rush, the excitement of building fades away too.

Take Elon Musk, for example. Sure, he’s the man behind Tesla and SpaceX, but before all that, he was the co-founder of Zip2, an online software company that he sold to Compaq for nearly $300 million. But instead of sitting back and counting his millions, he dove into the startup world again, founding X.com (which eventually became PayPal). And after selling PayPal, he didn’t stop—he just kept creating. You may like him or not, but he thrives on his new challenges, pushing the limits of what’s possible.

Their Interests Evolve

Sometimes, it’s not about the business itself but about where the founder’s heart lies. As people grow, so do their passions. The things they once loved might not be the same anymore. They may want to explore entirely new industries or pursue a cause that aligns with their current values.

Richard Branson, the founder of the Virgin Group, which includes everything from music stores to airlines, didn’t stop at just being a successful businessman. He’s ventured into space travel with Virgin Galactic and is committed to sustainability through his Virgin Earth projects. His personal interests keep pushing him into new areas of business that he finds exciting, meaningful, new.

Burnout Happens

Running a successful business can be an emotional and mental rollercoaster, especially when you’re at the top. The long hours, constant stress, and pressure to keep growing can eventually lead to burnout. For some entrepreneurs, stepping away from the grind and starting something new is a way to rejuvenate their passion.

I think Steve Jobs would be a good example of this. After being ousted from Apple (the company he founded), he didn’t just go home and relax. Instead, he started NeXT, a new computer company, which eventually became part of Apple when it was acquired in 1997. Jobs took the time to recharge and refocus, ultimately returning to Apple with a new vision that led to the company’s greatest era of innovation.

They Want to Make a Bigger Impact

Once you’ve hit the financial success mark, it’s no longer just about making money. Many entrepreneurs want to leave a legacy—something more meaningful than just profits. For some, this could mean starting a business that addresses bigger societal issues or pushes the boundaries of technology.

Look at Jeff Bezos. After founding and growing Amazon into the giant it is today, Bezos turned his attention to space with Blue Origin, aiming to make space travel more accessible. His focus shifted from just e-commerce to something far more futuristic, showing how an entrepreneur’s ambition to create an impact can evolve beyond their original business.

They Call for Freedom and Flexibility

I think I can relate to this one. When a business becomes successful and large, it can become a bit of a cage. There are more employees to manage, more stakeholders to please, and a lot of bureaucracy to deal with. So, some founders leave their businesses for a new startup simply because they want more control over their time, freedom, and decisions.

This makes me think about Mark Zuckerberg of Facebook (now Meta). While he remains involved with Facebook, he’s continuously diving into new areas, like virtual reality and the metaverse, trying to shape the future of the internet. With Facebook already in a dominant position, it gives him the freedom to experiment with newer, riskier ventures.

The Joy of Building Something New

For a lot of entrepreneurs, it’s not just about building a business—it’s about the process of building. They get a unique thrill from starting from scratch, putting together a team, and bringing new ideas to life. It’s not the end result that excites them; it’s the journey.

Look at Evan Williams, co-founder of Blogger and Twitter. After Twitter became a global phenomenon, he didn’t sit back and enjoy the ride. Instead, he started Odeo, a podcasting company that eventually evolved into the now-famous Twitter. Williams’ need to create and build was so strong that he jumped right back into the startup world after his first big success.

They Can Afford to Take More Risks

Well, an entrepreneur who’s achieved financial success has the luxury of taking bigger risks. With a safety net in place, he/she is free to explore ideas that might have seemed too risky before.

Larry Page and Sergey Brin, the co-founders of Google, eventually moved on to other ventures after selling Google’s advertising business to make it one of the most powerful tech companies in the world. They launched Alphabet Inc., a parent company that houses multiple experimental businesses like Waymo (self-driving cars) and Verily (health science). With their wealth and success, they had the resources to go after ambitious, long-term projects without worrying about failure.

Starting and growing a business is an intense, high-stakes journey, and for many successful founders, it’s not about sitting on their laurels once they’ve made it. I think it’s mainly the drive to innovate, take on new challenges, explore new ideas, and make a lasting impact that keeps them going. Whether it’s the desire for freedom, the need for something new, or the push to create something meaningful, these entrepreneurs show us that the entrepreneurial spirit doesn’t die once success is achieved—it just evolves.

So, the next time you hear about a business legend stepping away from a successful company to chase a new idea, remember, it’s not about leaving something behind—it’s about creating the next big thing. And who knows? Maybe the best idea is yet to come.