As you know if you're reading this, we closed Outlaw, our business of twelve years.
And I want to talk about the F word: FAILURE.
When we started Outlaw in 2013, my hope was that we would create an industry-changing company. That we’d go public. That we’d be part of an international movement that changed the industry. I believed that we would become a publicly traded company. That we’d create a massive, massive impact.
Not for profitable reasons (though I'd love to be wealthy, that wasn't the reason). I want wealth to be for the people. I want to build something that helps people remember who they are at their best. I want to build something world-changing for the better.
And as my mom said, “That seems like kind of a long shot.” Well, yeah. Of course it does.
In fact, many people would say that’s impossible.
But is it impossible? No. People have done it. It’s not completely impossible.
Are those people much smarter than I am? No.
Are they more charismatic? Possibly. Probably.
But I can outwork most people. And I think I’m pretty smart. I’m a good team member. I’m very good at finding incredible talent and working with wonderful people. I’m great at building long-lasting friendships and building a brand over time.
So no, it’s not impossible to think we could change the industry and build a multi-billion dollar company. It’s just hard. And hard and impossible are two separate things.
Walt Disney said, “I love the impossible because it means there’s less competition.”
So that was my definition of success. And if I’d kept that as my definition of success, then anything short of that is a failure.
We did amazing things. We changed people’s lives. We employed people. We gave people a good, safe place to work with full health insurance during the pandemic. And not only that, our customers have been writing me personally—thanking me for the changes our products made in their lives. How many of them found themselves in using our products. That happened. And it’s impossible to see that as anything but a success.
And when we made the decision to close the company, I wasn’t going to call it a failure just because we didn’t do the thing we set out to do.
As my friend, board member, and advisor said, "You either succeed, or you learn."
What I learned is that I could change my definition of success. That's not hard. That's just letting go of some stories. Sure, the ego puts up a bit of a fight. But my ego has never driven good decisions. Death to the ego.
Still... We turned the company around from a $1.2 million loss to profitability in just a matter of years. That’s a huge success. That’s an undeniable, measurable, real success.
But again—if I was still holding on to that original definition of success, the big dream of a multi-billion dollar industry-changing company—then yes, by that strict definition, I failed.
We were in financial distress—some might say irreparable. But I’ve always heard: you’re not out of business until you’re out of hope and you’re out of money.
We still had hope. Just no money. And I was going to hang on.
But I stepped back and looked at my life. Looked at what I really wanted in terms of success. And I realized I didn’t want to spend my life fighting to make a business profitable and calling that the win. I didn’t want survival to be the story.
Whatever "success" is, it's not a daily struggle for survival.
I still believe I am destined to have a world-changing impact. Not for my ego, but because I feel like the world deserves my contribution, and I have to have the courage to contribute.
But Outlaw wasn’t going to get me there.
So I had to choose: either keep failing at the big dream with something that wasn’t going to make it… or call this chapter a success. A success at building something iconic. A success at learning. A success at becoming someone who could try again.
Because I am going to try again.
What if, like the Tao says, you don’t climb up to success and you don’t drop down into failure—you just stand with your feet on the ground?
Concepts like these are only worth it if they make you happy. If they bring value and meaning.
Here’s what he wrote:
“Roshi said something nice to me one time. He said that the older you get, the lonelier you become, and the deeper the love you need.
Which means that this hero that you’re trying to maintain as the central figure in the drama of your life – this hero is not enjoying the life of a hero.
You’re exerting a tremendous maintenance to keep this heroic stance available to you, and the hero is suffering defeat after defeat. And they’re not heroic defeats; they’re ignoble defeats.
Finally, one day you say, ‘Let him die – I can’t invest any more in this heroic position.’
From there, you just live your life as if it’s real – as if you have to make decisions even though you have absolutely no guarantee of any of the consequences of your decisions.”
— Leonard Cohen
I wasn’t enjoying anything about it. It was clear I was never going to get to where I wanted to go.
Russ and I didn’t just invest money into Outlaw. We invested everything. Time. Energy. Our whole lives. As my dad said, “I can always make more money, but I can never make more time.”
We invested both. And I held nothing back.
So when I think about whether Outlaw was a success or failure, I have to include that too.
I did my best. I could not have done better.
For our customers, for our team, for our investors—I was relentlessly committed.
And yes, it still ended. It didn’t go the way I wanted. Outlaw wasn't economically viable at the end. I lost investor money. I lost money from friends. I wish that hadn’t happened. I really do.
But am I a failure because of that? No.
It was my first business. I had a lot to learn. The learning was expensive. If I add it all up, that education cost more than any MBA. And honestly, I think the quality of my education over the past 12 years wasn't even all that great. So it cost millions of dollars and I would like a refund.
But that doesn’t matter. Because, like my dad also said, “That’s sunk cost.”
You can’t worry about sunk cost. You can only worry about what you’re investing from this point forward.
And now, we’ve closed Outlaw.
And I’m proud of what we did.
That’s it.
