5 Years Sailing a Startup Sea

Yesterday, our team gave me these custom Nike’s.

They know me well.

🔥 🔥 🔥 🔥 🔥

We gathered in person, all 13 of us, for our quarterly business review.

They surprised me with this incredible gift for our 5 year birthday.

I can’t pack 5 years worth of lessons in one post, but I will hit a few of the highlights and lowlights of the journey.

– Survive & Persevere. 20% of startups are extinct after a year. 35% after 3. 50% after 5. I’ve said, “I’m grateful there still is one,” more times than I can count in response to, “How’s the business going?”

– The Seas are Stormy. Watching others from the shore is a hell of a lot easier. But not nearly as fun. Sailing on the sea is scary. But storms pass, they always do. And when it does, you’re still on the sea.

– Cash is King. As a bootstrapped, growing, evolving enterprise, cash is a source of comfort. And the lack of it produces massive anxiety. We’ve been at both ends of the spectrum, often, and to varying degrees. The rollercoaster is real.

– Hire Unicorns. You’re only as good as your team. We’ve been ridiculously fortunate to build a team who over-indexes in every category. Past and present, they came to be a part of a place where they put their fingerprints on everything. Building from scratch is hard work, and it takes gritty, brave, big-hearted people.

– Invite Responsibility. My ego says I should be involved in every decision. A healthier road for all is a team who is offered, and then takes, radical responsibility.

– Invest in Infrastructure. At my worst, I’ve tried to grow our way through pain. Just out earn it, out hire it, or out run it. Turns out, I can’t. Deeply invest in the how you do a thing, get it out of your brain, and into a document. Great wine grapes can only grow on great trellises. Build a bunch of trellises, and watch the grapes run wild.

– Care Deeply. Genuine care for another (team member, client, competitor) covers a lot of other stuff as you figure out your way. Celebrate birthdays, grieve losses, know dog’s names, be a caring human who others enjoy being around.

– Solve the Right Problems. Because there will literally always be 1,000 you could solve. “Is this the right problem to solve right now?”

– Don’t Take Yourself So Seriously. Smile, relax, take a deep breath, have fun. Unless you’re operating on brains, then be really serious.

– Gather Honesty. Building something is hard, and at times, lonely, work. Put people in your corner who are optimistic and for you, but who also love you enough to be honest with you.

– Envy is a Bitch. Don’t compare yourself to others. Everyone loses when you do.

– Love is Better Than Hate. Shame, criticism, fear may feel good in the moment, but it burns out quickly and burns everyone around. Bring light, love, and hope to the table more often.

– Wear Good Shoes.

Thanks to all the friends who have been part of this story. I’m deeply indebted to each of you. We sailed the sea, and we’re still sailing.


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