Millennials Weren’t Supposed to Be Entrepreneurs - Here’s Why I Was

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Today, we’re going back in time. Twenty years and one day, to be exact.

This may be the most foundational piece I’ve ever written for COLLIDE. You’re one of thousands of leaders who read this newsletter each week, but this story, the real beginning, has not yet been shared.

It was Thursday, August 25, 2005, when the paperwork finally arrived in the mail. My first business was official.

Just a month earlier, my dad had driven me to the Kane County Courthouse. I was fourteen, sitting on a bench with a one-page form in my lap, filling out the details of a company I wasn’t sure I was ready for, but knew I wanted. I handed over the application and the cash I’d saved from lemonade stands and odd hustles.

Then I waited.

For weeks, I checked the mailbox daily. When that certificate finally came, I took it straight to Bank One of Chicago, opened a checking account, and got my first debit card. In my blue vinyl Velcro wallet, I tucked away a newspaper clipping where my business name had run in the classifieds. The ink faded, but the sense of purpose never did.

This week marks twenty years in business.

And while COLLIDE usually dissects generational signals and leadership trends, today I want to reflect on entrepreneurship itself across generations. Where I fit, where I don’t, and what that says about how we understand entrepreneurs today.

By the data, I was never supposed to be an entrepreneur.

Millennials have often been called the least entrepreneurial generation in modern history. Using self-employment as the yardstick, fewer than 4% of Millennials were self-employed at age 30, compared with 5.5% of Gen X and 6.7% of Boomers at the same age (NWBC, 2017). The Kauffman Foundation also shows that the share of new entrepreneurs ages 20 - 34 fell from 34.3% in 1996 to 25.7% in 2020, while the share aged 55 - 64 nearly doubled. This illustrates that entrepreneurship has shifted older over time (Fairlie et al., 2021).

It’s not that we lacked ideas. We lacked freedom to try.

We came of age during the Great Recession, saddled with record student debt, skyrocketing rent, and fewer safety nets. Plus, we had all of those “necessary Millennial expenses” I wrote about last month.

The risk tolerance that previous generations could afford, often backed by savings, home equity, or a stay-at-home spouse, wasn’t as accessible to us. In fact, only 28% of Millennials described themselves as “not risk-averse,” compared to 40% of Gen X and 43% of Boomers in one multi-generational survey (Monster/Millennial Branding, 2013).

Yet entrepreneurship hasn’t died. It’s evolved.

From Primary Income to Side Hustle

Boomers started businesses to make a living. Gen Z starts businesses to make a statement and a side income, too.

Today, the very definition of entrepreneurship is blurring. In a 12-country survey conducted by Talker Research, 36% of Gen Z and 39% of Millennials said they consider themselves entrepreneurs, compared with 29% of Gen X and 25% of Boomers (Talker Research, 2024).

Wait! Am I contradicting the earlier stats I shared? Not at all.

When we look at primary income indicators, yes, Millennials and even Gen Z are trending toward being the least likely to derive their main source of income from self-employment. But those numbers, interpreted in isolation, paint the wrong picture.

The reality is that younger generations are, in fact, more entrepreneurial than previous ones; it just manifests differently.

For Boomers, entrepreneurship often meant opening a brick-and-mortar shop or going all-in on a business as their primary livelihood. For Millennials and Gen Z, it often takes the form of freelancing, reselling, content creation, or passion-based gigs layered on top of a traditional paycheck.

Deloitte reports that about 45% of Gen Z and 36% of Millennials hold side jobs (Deloitte, 2023). Upwork found that 52% of Gen Z and 44% of Millennials freelanced in 2023, compared to just 30% of Gen X and 26% of Boomers (Upwork, 2023). Meanwhile, the U.S. Census Bureau counted 28.5 million nonemployer businesses, mostly solo or side enterprises, in 2021, generating $1.5 trillion in receipts (U.S. Census Bureau, 2024).

And honestly? I get it.

Entrepreneurship has always been central to me. My first company launched when I was a freshman in high school. While balancing homework and hall passes, I was also building a marketing business that grew to more than 200 clients in 25 countries and helped nonprofits raise nearly $50 million.

That early spark carried me forward. Sometimes it meant running my own ventures from the ground up. Other times, it meant joining venture-backed startups, where I had the chance to pair entrepreneurial drive with the structure of a salary, including leading one company to a $750 million valuation during my tenure as president.

Through it all, I’ve led teams across every generation from Boomers and Gen Xers when I was still a Millennial teenager, to peers in my own cohort, to Gen Zers entering the workforce, and now even Gen Alpha as I raise kids of my own. That experience taught me that leadership isn’t just about people or process, it’s about perspective.

Since 2021, I’ve shifted into a new chapter: helping leaders and businesses optimize their teams, fuel growth, and prepare for what’s next. My passion is organizational behavior, approached with a futurist lens rooted in where we’ve been, but always vision-casting where we’re going.

A Generational Mutt - A product of the generational blur

I often say generational identity isn’t just about your birth year. It’s about birth order. Family dynamics. Geography. Parental style. Socio-economic status. Technological exposure. All of that creates what I call generational blur.

And by that definition, I’m a mutt.

By birth year, I’m a Millennial. But my dad is a late Boomer, and my mom is an early Gen Xer (just three years apart). They gave me a largely Gen X upbringing: long leash, minimal coddling, lots of experiential learning. If I failed, they didn’t always catch me in a safety net, they coached me through getting back up. However, unlike Gen X, I had a firm foot planted in the technological world. Also, my parents were far more involved in my life and school than most Gen X parents—but they were not helicopter parents.

By 7th grade, they had enrolled me in so many musical lessons that I could play nearly every instrument in the band room. That’s very Millennial. I had played quite a few different sports, many of which I failed miserably at. And that same experimental mindset extended to technology: I was dabbling in Adobe Photoshop before most people had home computers. That edge is what sparked my early business, offering design services to nonprofits.

I didn’t grow up expecting to be a founder. I just started solving problems. Sometimes out of passion. Sometimes out of necessity. But always with that same Velcro-wallet pride that I had at 14.

Why COLLIDE Exists

That’s the real reason for this piece.

The COLLIDE newsletter was born from that same origin story. As a Millennial who began managing employees, many of them older, before I could drive, I was constantly being asked: “Why is your generation so different?”

Eventually, that question turned into a keynote. Then a book. Then this community.

We often treat generational conflict as a people problem or a process problem. But in most cases? It’s a perspective problem.

COLLIDE is about shifting that perspective so leaders can better inspire, manage, mentor, and collaborate across generations. Whether you’re building a business, managing a multigenerational team, or parenting your own future founder, the lens matters.

So yes, this post is different than most.

But it's also exactly what this space is about.

Because generations don’t exist in silos, and neither do we.

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