Playing to Lose: Failure is the Foundation of Success

I’ve always loved games. So much so that I started my career building them: designing experiences and puzzles for my friends in high school, and eventually making video games professionally as a scrappy first-generation college student working in the San Francisco gaming industry. This early work taught me how to keep players engaged, how to tell stories through gameplay, and how to create systems that invited exploration and mastery.

And I can see now that the games that mean the most to me are the ones that can double as metaphors for life. Games like chess, like poker. They're not just contests of rules and tactics; they're tests of perception, patience, and psychology. They can reveal just as much about your opponent (and yourself) as they do about your next move.

Chess found me first. As a kid, I played game after game against myself, setting up endless puzzles to solve. I lived in that terrible middle space: good enough that my friends didn't want to play with me, but not good enough to beat anyone who actually knew how to play. 40 years later, I’m still in that spot (rated 1302 on chess.com!), but now I have the internet to help me find opponents. 

Poker came later, at that first gaming job. My boss would make me play on weekends. The thing is… when you’re young and in a creative job, where there can be stretches of time between your brilliant ideas… sometimes you have to justify your existence by indulging the owner of the company.  So every month I’d play with him and I'd lose. And lose and lose, over and over, effectively giving back a quarter of my paycheck each time. The problem was that I was always trying to outwit him, pull off some big trick and walk off with everyone’s money. I was objectively terrible.

But slowly, painfully, my time playing poker and chess was teaching me about strategy and  lending me wisdom – about timing ,resilience, , and the power of simplicity. Lessons that would eventually shape how I successfully build teams, products, and businesses.

Chess: The Power of Patience

Over my life, I’ve lost thousands of games of chess. Losing is hardly ever “fun,”, but collectively, all those losses taught me something priceless: tempo.

In chess, tempo is everything. Whoever forces the other player to respond sets the pace, runs the board, controls the narrative. You can feel invincible for ten moves... until one mistake flips the entire thing against you.

I’ve lived this in business negotiations too. Early in my career, I'd push too hard, too fast, or worse yet, I’d sit and wait, only to recognize the moment after it had passed me by. Savvier negotiators would simply wait me out, letting my eagerness erode my position.

Chess taught me that patience isn’t passive. It's a weapon.

Nowadays, my favorite way to play is as Black. I’m confident enough to know I can drive the tempo even if it doesn't look like it. I let my opponent believe they're controlling the game, while I slow the rhythm to a grinding slog, waiting for the inevitable slip — then striking with precision.

The best leaders don’t rush. They understand that controlling the tempo means controlling the outcome.

Stick to Your Strategy

A few hundred games more and I also learned that my strategy in chess only works if I commit to it completely. Every time I got too hungry and abandoned my strategy too soon, I lost. If my attention drifted and let “the moment” pass, I lost.

I used to make the same mistake in business and now I see it all the time in my consultancy. Teams develop a thoughtful strategy, start to execute it and panic when immediate results don't appear. They pivot. Then pivot again. And again.

You can absolutely pick the wrong strategy and lose. We’ve all done it. That’s life. But I promise, you'll never win if you don’t give your strategy time to work. Success isn’t always about a perfect plan. It’s about coherence and perseverance.

More businesses succeed with a good-enough plan executed well than with a brilliant plan abandoned halfway through.

Poker: The Long Game of Short Hands 

If chess taught me patience, poker taught me perspective.

In the movies you always see dramatic bluff: some reckless underdog pushing all in, winning everything in one hand. I spent so much time (and money) hoping for that story, playing each hand as if it were my last, chasing pots I had no business in and walking away empty-handed.

It took all those losses to learn the real lesson: Poker isn’t about getting lucky off one amazing hand. It's about surviving hand after hand, mostly folding small losses, waiting for the right moment to strike big.

There’s a cliché — “play the hand you’re dealt” — but good players know: most hands aren't worth playing at all. Folding isn't weakness. It's wisdom.

Now, I approach poker, and business, the same way: Play tight. Stay disciplined. Preserve your energy and capital for the moments when the odds shift in your favor, and when they do, act decisively.

Success isn’t about trying to force every opportunity. It’s about picking your battles and making them count.

Keep It Simple

When I first started playing poker, I tried to be the trickiest guy at the table, trying to play games and games within games, inevitably leading to my plans blowing up in my face and sowing unintentional chaos across the table. I would get so caught up in the moment that I'd forget the fundamentals and lose the plot.

Now, my approach is simple:

1. Play solid hands. 

2. Push when the odds favor me.

3. Bluff rarely, and when I do, make sure the story I’m selling makes sense.

If I'm betting like I have a three of a kind, I can't later pretend I have a straight. The story has to hold together.

In business, it’s the same. Simplicity builds credibility. If your strategy is clear, your team and your customers will believe it. If it's convoluted or constantly shifting, no amount of charisma will save it.

Complexity isn't impressive. Simplicity, discipline, and timing are.

Winning Is Overrated

The real gift of these games isn’t winning. It’s losing.

Every defeat is a rehearsal. Every time you’re beat, you’re being given a gift. Someone has taken the time to teach you the hard lessons of leadership and life. Your job is to actively listen to what they’re telling you: Read the room. Control the tempo. Stick to the strategy. Keep it simple.

One of my biggest lessons during Covid came during those early days, when everyone seemed to be thinking “this lockdown should have been over 2 weeks ago!", but it was becoming clear that no one was going back to the office.

At the time, I was working for a large NGO, surrounded by colleagues with impeccable pedigrees but who were dumbstruck with the loss we’d all been dealt. I looked around and realized: I wasn’t smarter, I wasn’t better credentialed, but I knew that I had something that could help us make it through the evolving crisis: resilience and grit.

Resilience is forged in the humbling experiences of failure — and the decision to keep showing up again, smarter and stronger. In those early months I stood up and led my team to grow and scale our products far beyond what anyone thought possible. It put me in front of our board, in charge of rescuing our most venerated domestic program. And we succeeded, raising hundreds of thousands of dollars to help those that needed it most in those dark times. 

Anyone can look good while winning.

The true masters are the ones who learn how to lose and keep playing.