Podcast

Why I Left Full-Time Entrepreneurship to Work at a Startup

Jeremy Chevallier
December 2019

Every so often in life, we’re gifted with sudden opportunities.

That’s what happened last month when my first freelance growth marketing gig unexpectedly turned into a full-time offer.

I’ve been my own boss for four years–as a freelancer, as the founder and creative director of Conscious Creative, and then again as a cofounder of PubLoft.

I used to believe I was unemployable, and the only option left was building my own thing.

It Doesn’t Have to be Freelance


Note: You can read about how I got my first freelance growth marketing client for some backstory. This piece picks up the second half of the story.


During my freelance sales process, I stumbled upon a few really cool employment opportunities–content marketer at Notion, growth marketer at Trend, growth hacker/wizard at Crash. And I realized something very, very important:

It doesn’t have to be freelance to feel like it’s within your control.

In my previous role at GigLoft, I’d been ragging on full-time jobs and touting the “work for yourself, not the man” mentality without realizing how blurry the line between the two actually is.

I realized a full-time role at a startup could still be fulfilling, could still be remote, could still feel entrepreneurial.

And that’s why I ended up accepting a full-time offer to join the Crash team on their quest to help people discover and do what makes them come alive.

Why I Took the Offer and Left Full-Time Entrepreneurship Behind (For Now)

I’ve been my own boss for four years. I wasn’t exactly jumping at the chance to work on something I don’t entirely control (but then, are we ever entirely in control?).

Opportunities come in many shapes, sizes, and colors. I’ll never stop being entrepreneurial at heart, and will continue to have a blast projecting GigLoft on the side until I decide to go full-time on it again.

Even when I was interviewing for the content marketing position at Notion, a rocketship with an amazing culture, I still ranked Crash higher in my mental list of opportunities.

Here’s why.

1. Crash invests in its people.

Just one week into our freelance contract, CEO Isaac Morehouse offered to fly me out to Colorado Springs for the six-person team’s in-person vision retreat–a three-day crash course, you could say. We jammed hard on product vision, customer success, and strategy moving forward. We also had a delicious dinner at Dave’s, our lead engineer, and hiked through the Garden of the Gods. Overall, it was a pleasure to work and play with the Crash team.

Not only did this experience help me build rapport with the whole team, but it also left me convinced they are people who care about the problem they’re solving, the people they solve it with, and the results their users get.

2. Crash has a proven, exemplary leader who trusts his team.

Isaac may laugh this kind of statement off, but it’s true. His leadership style and qualities are the primary reasons I decided to accept this role.

Every day, I’m learning to be a better leader myself, and there’s perhaps no better combination to learn than absorbing excellent leadership firsthand and applying it in my own department, my own body of work, and my own life. (Renting a townhome, planning a wedding, considering a cross-country move…oh my! These all benefit from leadership.)

“At Crash, you work when you want.”

That’s what Isaac told me when we were discussing this opportunity. It was important to me to be able to work only a couple hours during the day, if necessary, and still be trusted to get the job done–that’s how freelance/entrepreneurship operates, and I need that kind of freedom in my work.

I constantly see Chris Herd discussing how trust is one of the key components of remote work:

Freedom to work where you want is a form of trust a leader or employer grants. Freedom to work when you want–that’s another dimension entirely. And it’s going to work wonders for Crash and me.

3. Crash is betting on the type of young person I once was, and they deeply want to help.

I’ve worked with hungry, wide-eyed teens who yearn for more and don’t know how to get it.

I was one.

Had Crash been around when I was in college, I would’ve landed way cooler opportunities. Still, I talked my way into studio graphic design courses when I was taking a non-studio concentration. I earned a graphic design internship at a startup before I even knew what startups were. I got hired for my Illustrator and InDesign skills before I actually had them–and taught myself on the job during the first two weeks.

At Crash, we’re for the individual who is deeply motivated to create value and learn along the way but doesn’t have much experience in the field yet. We’re helping these people rethink the job hunt and approach it differently. We’re helping people start careers in fields they care about, rather than just “what’s available.”

We’re helping people discover and do what makes them come alive.

And that’s just freakin’ awesome. How could I not join? 😀


Jérémy is the Director of Marketing at Crash, where he’s helping people discover and do what makes them come alive. Connect with him on LinkedIn, say hello on Twitter, or email him at jeremy [at] crash [dot] co.

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