Imagine a world, where connecting to the internet means dialing a special phone number on a dedicated landline and praying that the call actually goes through. Or where homeowners and apartment-dwellers are solely responsible for disposing of their own trash. Or where launching a payload into orbit is so astronomically expensive that no one can afford to do it except the wealthiest governments. These scenarios aren’t ripped from some work of dystopian fiction. They were reality in the not-too-distant past.
We’ve moved past these and other inconvenient realities thanks to the tireless efforts of a very special group of people: serial entrepreneurs. Serial entrepreneurs love to build big, bold new businesses, and they often make the world better in so doing. Here’s a look at five of the most active, including some you’ve probably heard of.
- Oprah Winfrey
Oprah Winfrey was and probably still is the biggest name in independent media. Most know her as an influential and always-on talk show host without realizing that she’s also one of the wealthiest self-made women in the world.
Winfrey achieved this outrageous level of success by launching and scaling multiple related media ventures. She’s living proof that great things can happen when you intuit what your target audience — which in her case is just about everyone — really wants.
- Sky Dayton
Sky Dayton is best known as the founder of EarthLink, one of the first companies to commercialize dial-up internet access. If you remember the days before solutions like EarthLink, you understand how impactful they were — and can imagine how profitable they were for the people behind them.
Dayton parlayed his EarthLink success into several additional ventures, some nearly as transformative. He helped bring wireless hotspot provider Boingo to market around the turn of the millennium and helped launch the ghost kitchen phenomenon with his startup CloudKitchens. Sky Dayton also launched an early smartphone solution that predated the iPhone.
- Richard Branson
Is it a for-profit company with the world “Virgin” in the name? If so, it’s almost certainly owned by (or inspired by) Richard Branson, a famously brash serial entrepreneur with more than a dozen companies in his portfolio, including Virgin Mobile, Virgin Atlantic, Virgin Hotels, and Virgin Galactic. Branson is also a core investor in Breakthrough Energy Ventures, a diversified climate technology portfolio patronized by fellow serial entrepreneurs (and billionaires) like Jeff Bezos and Bill Gates.
- Elon Musk
Elon Musk needs no introduction these days. But if you only recently started paying attention, you might be surprised to learn just how many companies he’s responsible for. An incomplete list of Musk’s successes includes:
- PayPal (he was an early employee)
- Tesla
- SpaceX
- OpenAI (yes, that OpenAI, but he’s no longer involved)
- The Boring Company (a tunnel-drilling company)
- Neuralink (which is working on brain-machine interfacing)
- Wayne Huizenga
The late Wayne Huizenga might best be remembered as a co-owner of the Miami Dolphins, Florida Marlins (now Miami Marlins), and Florida Panthers. But he made his money before he bought into the NFL, MLB, and NHL.
How? Through three companies you’ve almost certainly heard of: AutoNation, Waste Management, and Blockbuster Video. He founded the first two and was a key early decision-maker in the last, so much so that he’s often regarded as a co-founder. And while Blockbuster Video is no more, AutoNation and Waste Management are still dynamic, impactful brands decades after their founding. Two out of three is not bad!
Final Thoughts
Anyone who runs their own business is technically an entrepreneur. But to be blunt about it, some entrepreneurs are more “entrepreneur-y” than others. Some people are born to build and scale businesses and brands.
The five people on this list are among them. There are many more not mentioned here, and others working on their first big thing. We’ll know their names soon enough. They’re living proof that big ideas can transform the world for good.
