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[Sep 10, 2023 · 3 min read][work]

When to Stop Playing

Honestly, some of the money we made in the bull market wasn't ours to be proud of.

I've been sitting with that sentence for a few weeks now, trying to decide whether to write it down, because it's not the kind of thing founders usually say out loud. But I think if I don't say it I'll start telling myself a nicer story, and nicer stories are how you end up making the same mistake twice.

When we started, the market was on fire. Every brand wanted an NFT strategy, every agency deck had the word "metaverse" on slide two, and budgets were being approved for things nobody fully understood, including, at times, us. We were good at what we did, and I'm proud of the work. But if I'm being straight with myself, the market was paying us for the mood as much as for the product. Dehidden scaled too fast in the bull market - we were making more money than the value we were providing. And I was always trying to deliver more value to catch up with the absurd prices.

That gap is dangerous, and it's dangerous in a sneaky way, because from the inside it feels exactly like success. Revenue's up, the team's growing, clients are calling you. Nobody sends you an email saying "hey, just so you know, a big chunk of this is the market being silly". You have to notice it yourself. I've watched enough cycles to know how this bubble pops.

I've sort of turned one idea into a personal rule over the years. My purpose in life is to play positive sum games. Life is just a game. And it's important to keep playing. The deals I love most are the ones where everyone walks away better - the brand gets a community that actually cares, the users get something fun and real, we get paid for creating that. When it works like that, you want to play forever.

But a bull market bends the maths. When the value you're being paid for is bigger than the value you're creating, somebody on the other side is losing, even if they don't know it yet. Often it's a VC taking that 1-in-33 gamble that one of their startups will moonshot, and even they're wrong a lot of the time. But the layman buying in at the top can't stomach that kind of risk appetite. The game stops being positive-sum and quietly becomes something else, and you're still smiling on the call because the numbers look fine.

I don't think we did anything wrong, exactly. We built what people asked for and we built it well. But if there's one thing I've learned this time, it's how to walk away. When you know calamity is coming, don't be the doomsayer running around warning everyone - they'll just think you're crazy. Quietly get your own house in order. Everyone talks about grit and never quitting (I'm guilty of this, I love that stuff), but there's a different kind of courage in looking at a game you're winning and asking whether it's still a good game.

There's a small list of questions I've started asking myself, usually late at night:

Would the people paying us be happy with what they got, if the hype disappeared tomorrow? Would I still build this if the market cared a lot less? Is everyone at the table still having fun?

When the answers start going the wrong way, that's a signal. It doesn't mean panic, and it doesn't mean burn it all down. It means be honest with yourself about what you're actually being paid for, and be ready to stop playing.

Life's longer than a bull market, and your mind and business should be resilient to it. Plant seeds that grow slowly over seasons, and don't play games fueled by fear and greed.

Be good, do good, the rest will figure itself out.