

In today’s tech-driven business world, the title “serial entrepreneur” is a coveted badge of honor. A quick look at Google, for example, yields no less than 830,000 mentions — with “how to become a serial entrepreneur” topping the list of popular searches. And all the while, the phrase increasingly pops up in personal bios, job applications and everyday conversation. Of course, it’s easy to understand the appeal of the phrase. It suggests that someone is so full of groundbreaking ideas they can’t channel all of them into just one company. Instead, they choose to focus their genius on creating an array of world-changing, money-making businesses.
Who wouldn’t want that to be in that club?
But there’s a problem with glorifying serial entrepreneurs: It suggest that the number of companies someone has built and sold and the money they’ve made as a result are the ultimate metrics of success — not the actual impact on society. By exalting entrepreneurs for a series of financial wins, we attract the wrong kind of people, promote an income-first, outcome-second mindset and create serious potential to stall true innovation.
America’s never exactly been known for its moderation. The thinking goes that if some is good, more is better, whether that’s referring to money, portion size or hours spent at work. So when tech started to shed its geeky image and Mark Zuckerberg and Steve Jobs became household names, applying the same logic to entrepreneurs was a natural progression. And it wasn’t long before multi-venture mavericks like Elon Musk, Jack Dorsey and Max Levchin achieved rock-star status.
To be clear, there’s nothing inherently wrong about starting more than one company (and for the record, I’m a big fan of all the aforementioned founders).
But somewhere along the way, the praise for serial entrepreneurs’ passion and innovation got distorted — as it so frequently does — the more it spread. As much as you hear about entrepreneurs’ business endeavors in and of themselves, you also hear about their net worth and lavish lifestyles. So what exactly does this all lead to?
For one, this results in an influx of entrepreneurial hopefuls who are eager, but not always prepared. College and MBA students in particular are quick to turn to the startup world, even as their schools caution against building their own businesses too quickly. There’s even been buzz about the pre-college crowd getting in on the action. Despite their best intentions and high aspirations, the reality is that most startups fail — and in order to beat those odds, you usually need a decent amount of experience under your belt first.
But more worrisome is that the allure of serial entrepreneurship also brings in those who have less lofty ideals, their sights set on monetary gain or personal glory. The well-documented brain drain from Wall Street to Silicon Valley stands testament to that (as do the small but growing number of would-be entrepreneurs we all know who seem to spend most of their time building their brand through social media, trade shows and networking events). If there’s anything we’ve learned from Wall Street, it’s that a deluge of incoming talent and a voracious appetite for profit leads to bad behavior and, potentially, crises.
On a tactical level, the serial entrepreneur mindset often manifests in a focus on “successful exits” rather than meaningful change. In a society where we place value on the number of entrepreneurial notches on somebody’s belt, a series of acquisitions is seen as the ultimate goal.
There’s a reason, after all, that the term acqui-hire exploded over the past few years. And while evidence suggests that the frequency with which tech titans buy out relative newcomers is slowing down, you can still find a steady drumbeat of people asking and advising others how to successfully get acquired.
There’s certainly nothing wrong with acquisition in itself, but making it your ultimate goal from the beginning is short-sighted. The world’s most innovative and world-changing companies — Google, Apple, Facebook — didn’t get to where they are today by hoping they would be sold to someone else.
And, ironically, if acquisition alone is your strategy, you may be setting yourself up for failure. In an attempt to grab the attention of major players, ideas often get regurgitated. Startups developing an “Uber for X” or “Spotify for Y” are so common that it’s become a cultural in-joke — and these “recipes for success” are usually anything but.
What’s worse, the myth of the serial entrepreneur with the Midas touch perpetuates a false notion that there will always be another opportunity waiting on the other side. I worry that if this thought process continues, temporary hurdles will start to become viewed as a signal to start searching for greener pastures, leaving more and more companies — along with any difference they could have made — left for dead.
With that in mind, I think we need to stop using the phrase “serial entrepreneur” altogether. You might argue that words alone are harmless, but there’s no doubt that language has a powerful role in shaping how we think.
My goal here isn’t to bash people who call themselves serial entrepreneurs, or criticize anyone who’s gotten in on the ground floor of more than one organization. Instead, I want to encourage others to reflect on how they define entrepreneurial success, and think critically before they move onto their next passion project or publicly applaud somebody for the number of companies they’ve built.
There’s a big difference between founding a startup for the sake of founding a startup and using business ventures as a vehicle to achieve wide-scale impact, as the Elon Musks of the world have done. And if we want to communicate that to the world, we should first strive to build our current startup to the point that it’s sustainable and successful enough to be the last one we ever work at. If we can do that, we might just move toward a culture that truly walks the walk when it comes to promoting innovation and change.
