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The Last Five Years (at Crew)


A look back on the company, the myth, the legend. And what it feels like to sell your (figurative) baby.

This week we announced that we sold Crew to Dribbble.

Crew, this thing we created and worked on tirelessly for the past five years, is now in someone else’s hands. I'm no longer working on it.

It’s hard to explain how that feels. To go from full-force to full-stop.

Sad, sure. Proud, that we created a company with legs. Relief, even, for not having to worry about it anymore and then a little guilt for feeling that way.

You make a ton of difficult decisions running a business, and selling Crew was one of the hardest. And for me, personally, the decision to move on after the sale was just as difficult.

It’s a tough decision to open yourself up to the unknown and give yourself the space to figure out what that next thing could be. It can be scary. The easy choice is to keep doing what you've always done.

But First We Have To Look Back

My co-founder Mikael put together a "graduation" slideshow of photos from Crew offices and events and retreats and meetings. Watching it, I couldn’t believe so much had happened. It seems like it was a blink.

And yet so much has happened. Pivots, fundraising, expansion, company splits, a cafe!

I posted last year about the opening party of the Crew Cafe, and what a night it was and that it was one to remember.

There were plenty of nights like that. But there were even more days when nothing in particular was happening, but you just felt good. Maybe something was going right, maybe it was the pride of creation. Hard to pinpoint the why, but there were those days when you just knew this was a great god damn thing to be doing.

We were creating a company with great people and doing our damnest to do right by them, and everyone else who believed in us.

Of course, inevitably, sometimes things didn't go right.

Sometimes, we let a teammate down or let the company down or a great idea didn’t pan out the way we imagined. We kicked ourselves in the ass harder than you might imagine - no one is harder on themselves than a founder who let down the team they care so much about.

We pushed every damn day to get better. (I'm not nearly as mean now.)

I Know I've Been Lucky

What I’m saying is this: I lucked out.

Ask anyone and they’ll tell you same thing: the team is what made Crew great. I got to work with amazing people. Working with them every day was, for no better word, fun.

Without the joy of working with this team everyday, we never would have been able to push the way we did or get to where we did. We had to love being there or we all would have folded under the pressure.

The pressure of building a new company is intense.

It’s why investors invest in teams first. The right team can move mountains. The wrong team will look at a mountain and think, “That's fine where it is, it’s almost 5 anyway.”

I also got the best education I could hope for. I thought I knew a ton when I started this but, as the saying goes, you don't know what you don't know. Now I know what I didn't know and it was a lot. I'm glad I know it now.

I’d worked in new companies before, started my own before, and I went to business school way back many years ago. Yet Crew taught me things those places didn’t. Like how to manage a team, and how to market products, and how to build a brand and community, and how to build a big ol’ product.

You don't get to keep your company if you don't do all of those well.

It also taught me how not to do those things next time. Expect a lot of posts here in the coming months about all the lessons learned and strategies I've developed and things I'll never ever do again.

It’s Only The End of Act I

I’m talking about Crew in the past tense as if it’s gone, but we’re only at an inflection point in the history of the companies we created. The new owners of Crew will figure out what to do with their shiny new Crew. Unsplash and the Cafe, meanwhile, will carry on as the old Crew before it. I won’t be there physically, but I’ll be there in spirit. I know all the work we’ve done together over the past five years will give Unsplash even more fuel for its rocket ship.

Startups come and go all the time. Somehow, through a combination of luck and hard work, we got to create not one, but two great tech companies and a stunning cafe.

That’s a lot more than I expected when I packed up all my shit, moved to Montreal, and started working on a little thing called ooomf.

Here's to Crew. And the best five years a person could ever ask for.

The Last Five Years is one of many musical soundtracks that I listened to quite often while building the first few versions of Crew.

Banner photos, TL to BR:

1. Hiking in Hawaii, 2015

2. Bowtie day, 2015

3. Some of the product team in Floria, on the last Crew retreat, 2017

4. Moving out of our tiny one-room office, 2013

5. Moving into our slightly-bigger two-room office in Old Montreal, 2014

6. Packing up all the Kickstarter Unsplash book rewards, 2016

7. Our Old Montreal office, 2015

8. Video call during a product launch night, 2016

9. Data, data, data. Our board next to the Crew letters, 2015

To quote a song in Avenue Q, "I wish I had taken more pictures."