The Invention of the 20-Something-Year-Old Founder

Yes, friends, there was a time in the days of startup yore when being a 20-something-year-old Founder was unheard of. It was the best of times, it was the worst of times, but mainly it was 1994, and rollerblading was still a thing.

I was a 19-year-old college student that had been living inside the Internet long before the Web browser came along (thank you, Marc Andreessen). I had this notion that these new "Web Pages," as we called them, would be a big deal, so I set up shop to build them for people.

Things were just starting to take off, and I went to my guidance counselor, full of excitement, to tell her I was dropping out of college. She was startled. "What's wrong? Is everything OK?" she inquired, to which I emphatically responded, "Of course! I'm going to be the Founder of an Internet company!"

She looked at me blankly and asked, "What's the Internet?" (There was a time...)

The Invention of the 20-something Founder

What most people don't realize, because it was 3 decades ago, is that being a young startup Founder is a relatively new concept, mostly ushered in by the Internet craze of the 1990s. That's not to say young Founders didn't exist before (Gates, Jobs, Dell), but they always existed as a total anomaly among what was almost exclusively old, silver-haired men who were CEOs.

The gold rush era of the Internet did something that would forever change the fabric of startup culture — it gave really young people a tremendous amount of power and opportunity. The problem is that the rest of the world hadn't gotten the memo yet, so we looked like a circus act to everyone else. Imagine that same thing happening today, but all the funded Founders are 11 years old.

For the first 5 years of running my Web design agency, no one recognized me as the CEO when I walked into a room. They kept waiting for the CEO to show up as if I were an intern who had arrived to prep coffee. And no meeting ever began without at least 15 minutes of banter about how "adorable" it was that this child in a poorly-fitted suit was actually running a company.

While that may sound quaint in retrospect, I can assure you it was absolutely humiliating.

Starting at Less than Zero

Compared to the 90s era, what it means to be a young Founder today is dramatically different. Today if someone wants to start a company at 21 years old, you can cite a dozen references to a similar success story. That's relatively new. When that comparison doesn't exist (like it didn't for me), there is no baseline to suggest you'll be particularly successful, which demotivates the Founder, potential investors, and every single person that would ever consider working for us.

We also had absolutely zero support. There was no Startups.com, or local incubator, or the entire friggin' Internet to help us on our journey. Best case we'd find a business book at Barnes & Noble written in the 1980's about "How to Start a Small Business." There were no active angel investors we could contact or local hometown startup mentors to tap. Nothing.

More importantly, we didn't have any way to compare notes with other Founders because we couldn't find them. In 1997 I had to hunt down and make a phone call to the offices of every Founder in town in order to invite them over to my house to start my first "Founder Group." It was the first time I learned how other Founders had the same struggles as me.

Standing on the Shoulders of Giants

The foundation for what it means to be a 20-something Founder today exists because of the bravery and hard work of a ton of early Founders before us. No, I don't mean Elon Musk.

I'm talking about names that Founders today may not even know, like Jerry Yang (Yahoo!) and Marc Andreessen (Netscape) whose early Internet success (and baby faces) got the whole world familiar with the fact that us 20-somethings were more than just a silly sideshow. I'm talking about people like Mark Zuckerberg (Facebook) and Larry Page (Google), who, instead of selling out early, decided to create massive Internet juggernauts before they turned 30.

Their success at such a young age proved that a 20-something CEO could be a force of nature. They helped inspire a massive ecosystem of Founders, investors, and startup junkies that are willing to take huge risks because of the ROI they have shown us.

Today an entire generation of young Founders exists in a world that never before embraced them. Which begs the question — who else have we yet to unlock? I can write volumes, but here's to all of us starting their journey like ours was created before us.

In Case You Missed It

What to Expect in the First Year (podcast) As Founders, we think we know how our products and businesses will look and function for years to come, but, as with time, it's nearly impossible to expect the unexpected.

Why No One Tells Founders "It's over, move on." No one ever actually tells Founders it’s okay to quit. No one except other Founders, of course.

Retiring Early is a Broken Concept Retiring isn't really our end goal, so we shouldn't aspire to it. What we really want is to shape our life the way we want it to be.