How to Keep Winning

I've always been fiercely competitive. I enjoy everything about it—from training to get better, to building and developing teams, to the stress, pressure, and intensity. And while I love winning, there are very few things I dread more than losing. It just feels awful. This meant that I had to get good at constantly not losing. Here are six tactics and principles I learned along the way to protect against failure and keep winning.

1. Don't Die

Almost everything else you can come back from except death. I'm using "death" both literally and figuratively to mean the point of no return. First, know the death boundaries, and obsess over the extreme downside scenarios and prioritize survival. Visualize all the ways you could die—all the time. In that way I'm very careful, almost paranoid. I ran Replit for eight years with little commercial success, but at no point did we ever get to the red zone when it came to runway—we always had plenty of cash on hand. You'd be surprised by the number of brilliant founders that reach out to me for advice when they're three months from death.

Once you're deeply familiar with the death conditions, you can take extreme risks because you know you'll always come back when things go sideways. Especially in America, and especially in Silicon Valley, people are forgiving of failure. You can come back from almost anything.

At Replit, there were many times when the business sort of worked and any rational founder would have decided to scale it. For example, we had a decently growing business in education and recruiting, but both markets felt unexciting to me—we couldn't build a big company or achieve our mission that way. So we pivoted. The most recent pivot was from being primarily a coding editor to becoming a natural-language creation interface (vibe coding). Some employees and customers were upset and left (some have since returned), but I knew I had to align with the biggest revolution the world has seen since the internet. When you eventually make it, people won't just forgive you, they'll join you.

2. Never Quit

Everything takes time. Some startups explode from day one and some prodigies play piano at three, but those are rare—and often fleeting. Most sharp rises end in sharper declines. If you've set your mind to something, then why ever quit? If you're not dead, then you're still in the game.

When you talk to entrepreneurs who quit on their dreams, even when they still get massively rich through investing, they always have a look of immense pain in their faces when they tell you that they timed it wrong. That they were too early.

Well, you're only "too early" if you actually quit (or died). They had all the right ideas but stopped short of striking gold. Often, gold is only two strikes away. Don't let that be you.

When you consider quitting, try to find a different scoreboard. Score yourself on something else: on how many times you dust yourself off and get up, or how much incremental progress you make. Almost always, in your business or life, there are things you can make daily progress on that can make you feel like you're still winning. Start compounding.

Some of the best businesses started off slow and just compounded all the way to heaven. One of my favorite charts is Amazon's growth because it's consistent over many years—and it's still compounding. It's really hard to stop companies like this. It's impossible to stop founders like this. So maybe you're not winning on some external scoreboard, but you always have your internal scoreboard to measure yourself and your team on. Have patience.

3. Lock In

I remember doing a spelling bee when I was maybe in third grade, standing in line waiting to get called on to spell the next word. I looked around me and all the other kids were talking and joking around. I thought that was strange. How could you ever win if you're not in the mindset of winning. If you're not locked in?

For me, I would stand there and keep reciting difficult words. And although I was slightly dyslexic, I still won every freaking spelling bee. With this simple trick, I dominated it so much to the point that my teachers, who loathed me for being a slacker, once tried to rig it in favor of their obedient A-students (I still won).

On a day I have to perform, I'm impossible to be around. I'm in the winning mindset. If I can observe how others are doing, I will study their every move. I recently participated and won a timed car race. While waiting, I watched everyone's mistakes and learned from them. By the time I went to do my trial, I knew exactly the bare minimum I needed to do to put myself in a winning position. After you eliminate risk, it's all upside from there.

4. Do Hard Things

Most people do the obvious thing. They don't want to look weird or different—but winning is weird and different. You're definitionally different because you stand apart from everyone else as the ultimate winner.

I used to be a pro gamer, and when my friends and I picked up a new video game, everyone would follow the game's instructions and do the obvious thing. On the other hand, I would explore the edges of the game. I'd explore every weird build, every different weapon, and frankly look like a noob for a long time. That's good. They'll underestimate you. But you're compounding. And eventually, you'll go vertical, creating a massive distance between you and the next participant before they know what hit them.

People by nature take the path of least resistance. If it's working, they'll keep going. Doing hard things means you're going on an untraveled path. It's risky.

When I started working on Replit many years ago, venture capitalists would look at our competitors and see that they were growing faster or making superficially more progress, and they'd ask us "why not just do this or that?" But it was never that simple. I wanted to build real technological depth. Something lasting. If it's easy, then there is no real lasting advantage. It's easy to create the surface thing, but the right (hard) infrastructure technology compounds.

In building a technology company, you're often faced with a strategic decision of whether to build or buy. Every build-or-buy decision should be treated with care, but what's certain is that buying tech is strategically fraught because once you run into the limits of the technology, you can't fundamentally change it. But when you build, you'll be able to adapt a lot faster and find ways to win on the tail events—e.g. valuable yet rare use-cases—that are impossible to handle with an outsourced platform.

For example, at Replit we built a distributed file system to solve the problem of collaborative coding. The easy solution was to buy any one of those services that give you an API to do collaborative editing. Instead, we took the problem one level deeper and built a powerful abstraction. A filesystem where any operation can be reversed, where it can be forked in a fraction of a second, and can be easily stored and backed up. When coding AI agents became possible, we quickly adapted the technology, and now we use this tech to do parallel agents—and as a side effect of concurrency features we were able to build a time-travel feature that's important for reversing destructive agent actions.

5. Play by the Rules

You might think that maximizing risk means you can break the law or do unethical or immoral things. But in my opinion, there's something about the universe that really doesn't reward that. Yes, there are exceptions—there are slimebags that make it really big, and evil companies that maintain a winning position—but those are either the exceptions or their time will come. For the most part, if your competitors are lying, deceiving, or taking unethical shortcuts, it'll only help them in the short term. Don't be tempted to do the same. Stay focused.

Playing by the rules is hard. It's doing the hard thing, and that has the side effect of forcing you to innovate your way out of problems. Those innovations might compound in interesting and weird ways resulting in longterm moats. Think of Apple and how taking privacy and security seriously—despite competing against Microsoft, which didn't care about either at the time—created a lasting consumer trust advantage.

6. Put Something Back

Steve Jobs talked about "putting something back in the pool of human experience." He said that putting something back was "extremely neat"—I agree!

But it's not just neat. It's not just an ethical good, it might also benefit you in the future. Karma seems real. When you put something back into that pool, your reputation will grow, people will be familiar with your work, and they will want to be around you and work for you. Winning can compound by giving back. Win and give to win more later.

I always liked open-sourcing software, sharing my experience, and talking publicly about how I'm building things—in some cases an entire roadmap. For example, Replit Agent was the first fully generative software creator on the market that's accessible to anyone. I shared the roadmap for that in its entirety in a TED talk almost a full year before launch. Our roadmap was public—it still is—but I can't remember a time where that was a disadvantage. Ideas are important, but what's precious is the generating function. The well from which those ideas spring.