A founder's letter to himself

I made the leap from my full-time gig to my startup five years ago this month. Today I’m sharing that resignation letter, and the letter I would write to my past self, if I could.

I didn’t leave a job I hated. In fact I loved my team, job and boss. Still, it was time to start building my own company. This wasn’t some romanticized celebration. The truth was I was losing my health insurance and security, all while my wife was nearly nine months into carrying our second child.

Many early stage founders ask me the same question:

"How did you know when it was the right time to make the leap?"

I could write a book on that question. Maybe one day I will, but here is the truth:

I didn't quit my full-time gig to go make a fat CEO tech salary and ride off on a J-curve rocketship into the sunset. I also didn’t starve, eating boxes of noodles. It really wasn’t that clean of a break, either.

In fact, it was very muddy.

Yes, I left to get GoWild off the ground, but what many don't know is I worked a part time gig to make ends meet for months. For about 20 hours a week, I worked as an Interim Marketing Director for a local insurance tech company, where I started building a team, setting up a CRM, building out marketing collateral, and eventually hiring my replacement.

I was still working two jobs.

Some have crystal clear moments of "I have to do this right now." I had one of those moments, sort of, but it wasn't like I was rolling up to the GoWild office 5 days a week after I quit.

OK, that was partially because we didn't have an office yet. The office did come that summer though.

October 2018, I made the true full-time leap. I'll forever be grateful to Russ Carroll, Seek Now's founder, for being the change agent who made my leap of faith possible. He saw what I was trying to do, and saw an opportunity to help.

Today I could apply some revisionist history and say that everything was the perfect result of my genius. It would be easy and certainly the common thing to do. However, I was anxious about it all. And looking back at the resignation letter below, I recall the sadness.

The resignation letter:

“Brad Luttrell        Feb. 5, 2018

Dear Kate,

I am resigning from my position as Creative Director, effective as of Feb. 23, 2018 or the birth of my child, whichever event happens first. I also understand OOHology may choose for this time to be sooner.

Working at OOHology has changed my life. This place has evolved my career, shaped my character and bonded friendships that will last a lifetime. You took a gamble on the kid who walked in, freshly fired but eager—and I will never forget it. You were the first person in advertising who believed in me, and I see that day we first met as a pivotal moment in my story. You made it possible to chase my dream to be a Creative Director, and your leadership has shed much wisdom upon me. OOHology has meant the world to me over the last five years and has provided more than a job. Despite my pride in what we’ve built and my love for you and my team, I have to take this step.

Thank you so much for the opportunities you’ve given me. I look up to you, and see you as a friend, so I hope you know I mean it when I say this was a very hard decision—one I’ve agonized over. I will miss working with you more than anything.

I promise to help you in any way I can over the next few weeks and even beyond. I would love to help finish up some projects, if possible and deemed appropriate by you, but most of all, I want to transition however you and the OOHology leadership team see best.

With more love and gratitude than I can possibly convey,

Brad Luttrell”

I have no mixed feelings about admitting I was conflicted about this decision. I truly did love working for Kate, and I had a fantastic team, most of whom I had hired. Arica and Donovan would eventually follow me to GoWild. Donovan as a Cofounder, and Arica took over our marketing efforts and eventually became Director of Member Experience.

While I won’t apply any revisionist history, I wouldn’t mind sending myself a letter from the future. I can hear Doc telling me not to influence anything, as it could shift the future. But screw it, I’ll go for it.

Here is the letter I’d write to that founder back in 2018, taking the leap:

“Dear Brad,

First, this is your future self. I know, it’s weird. Trust me, this isn’t even the weirdest part of what’s coming for you over the next five years. I can’t share it all—that’d take the fun out of the journey—but these tips will come in handy.

• Congrats on making the leap to GoWild. Soak this moment in, because it’s a milestone that will remain among your favorites for the rest of the ride. You’re living the glory days.

• When your cofounders bring a six pack into the conference room to share to celebrate some milestone, celebrate with them. The highs from the wins are short, and the withdrawals you’ll feel while trying to earn another win are going to take a toll on you.

• Never half ass fire anyone. You brought them into the company, and their failure is ultimately yours. Take the time to properly let people go when they don’t work out.

• Learn to get to “no” faster. Whether it’s investors or client partners, one of your biggest weaknesses is thinking you can will things to happen. You can’t. Watch for common themes in rejection and learn to see it coming.

• Keep that hard-nosed Appalachian fighting spirit. In fact, hone it. It comes in handy in a couple of years. Be ready to fight for your company’s life.

• Soon you’ll have people showing up to try and buy what you’ve built. Just focus on building the company and don’t go down these rabbit holes until you’re ready.

• Big companies are going to bully, belittle and even threaten you. Just know it’s not because they’re confident in their product, it’s that they’re threatened by yours.

• Stay focused on your core product. A pivot is coming—one I can’t tell you about, you have to earn that yourself—but please, stop chasing squirrels and stay focused on the target. This is one of your biggest weaknesses as a leader. You can’t and shouldn’t do it all.

• No check is worth working with assholes, whether it’s investors or client partners. Stay morally and ethically straight and don’t let these people get in your head.

• Take more runs.

• Start buying snowglobes when you travel. They’re fun trophies from your travels. (Just trust me here.)

• You’ll build a better team with love and respect than an iron fist. Learn to shut up, make fewer team speeches and just listen to the smart people you hired.

• Hire and fire fast. It’s what’s right for you, the team and the person who needs to be let go.

• Your kids and wife are still the most important thing in this world. Don’t forget it. Put the phone down in the evenings, soak in those laughs and get all the hugs.

• You are going to have a great mentor network. Lean on it. You don’t have all the answers and no one expects you to, but they do trust you to find the right answers. Mentors help get to the right answer faster.

There’s plenty more I could say. Honestly a book could be written about everything you’ll learn over the next five years. But if I’ve learned anything, it’s that the fun of it all is figuring it out. To handover the keys to the castle of wisdom would be to steal the joy of the journey. I won’t deprive you of the joy of figuring it out, beyond these tips.

Stay strong and love hard,

- You, but a little wiser”

One tip to wrap up today: Document and reflect

If you’re a regular reader, you know I do a lot of reflecting on milestones. I have more coming soon, too. I find it to be really rewarding in keeping my confidence strong but also realizing that I make mistakes. I could look back at myself in 2018 and think about all I’ve learned, but I also see all of the things I’ve screwed up over the years (such as being distracted by cool ideas that were distractions to our core product, or “squirrels” as we call them). Reflecting on my past mistakes keeps me on my toes, because I am constantly wondering what I’m screwing up now that future Brad would be embarrassed by. Sure, I do find things I’m proud of that make me realize how much I’ve learned. But realizing how “unknown unknowns” never stop coming is also a great reminder.

Who I’m listening to: S.G. Goodman

What I’m reading: “The Rise and Fall of the Third Reich”

Follow me for mid-week updates:

LinkedIn | TikTok | GoWild | Twitter | YouTube