# Winning Team, Losing Team

By James R. Stewart · Published September 11, 2026
Source: https://jamesstew.art/notes/winning-team-losing-team/

![Pen-and-ink drawing of a number 10 football jersey draped over a desk](https://jamesstew.art/img/winning-team-losing-team.jpg)

There is a type of football player who looks much better after being traded. Same arm. Same speed. Same brain. Different offensive line.

Suddenly he has another second to throw. The receivers are open. The play calling looks smarter. He stops forcing passes because he doesn’t have to. The team wins, so the coaches trust him more. Because the coaches trust him more, he plays better. A year earlier everyone was debating whether he belonged in the league.

This happens in business too.

I’ve spent much of my career moving between winning teams and losing ones. The main thing I’ve learned is that it’s surprisingly difficult to tell how good you are while you’re on either.

At one startup I worked harder than I have almost anywhere else. It was an early-stage financial technology company serving a difficult customer segment. We needed banks and infrastructure companies to let us operate on their rails. Those companies had their own risk committees, regulators, economics, and reputations to protect. And they did not particularly want our customers.

Partners dropped us. We found replacements. Those replacements dropped us too. Each time, the company mobilized. New meetings. New plans. New integrations. New risk controls. New spreadsheets demonstrating why things were definitely going to be different this time. People worked nights and weekends.

It didn’t matter much. We were playing uphill.

There is an appealing story in Silicon Valley that sufficiently talented people can overcome almost anything. This is useful propaganda if you are trying to convince talented people to join startups. It is also plainly false.

Sometimes you can execute well and still have a bad business. Sometimes the market doesn’t want what you’re selling. Sometimes your suppliers have more leverage than you do. Sometimes the economics are wrong. Sometimes the entire industry has decided that your particular type of customer is radioactive.

Effort matters. But effort is multiplied by circumstances. Ten times zero is still zero.

I didn’t understand this as clearly until I later found myself on the other side.

At a large financial company, I work on crypto products. We have a recognizable brand, millions of customers, capital, lawyers, compliance teams, engineers, and a banking charter. People answer our emails.

This is an underrated corporate asset.

When we started negotiating with a group of infrastructure vendors, several competed for the business. Fees came down. Terms improved. People internally were understandably pleased with the negotiations. They should have been. Good negotiation still matters.

But I remember thinking: of course they gave us a good deal. Look at the jersey.

A small startup might spend months trying to get the same vendor to return an email. We walk into the room carrying customers, distribution, credibility, and future revenue. The negotiator is playing the game. The organization has already moved the ball forty yards down the field.

This is one of the pleasant things about being on a winning team. The world cooperates with you.

Good candidates want to work for you. Partners want your logo on their website. Reporters return calls. Investors assume you know something. Customers are more willing to trust a new product. Even mistakes are interpreted generously.

When a losing company changes strategy, people call it desperation. When a winning company changes strategy, people call it optionality.

The dangerous part is what happens next. You start thinking it’s you.

I saw a more extreme version of this at another company earlier in my career. For a while, we were one of the dominant firms in our corner of crypto. Business came to us. The company grew quickly. Smart people joined. The numbers went up.

Winning creates its own weather.

You become more confident because things are working. Your confidence makes other people more confident in you. Their confidence produces more opportunities, which produces more evidence that your original confidence was justified. It is a nice loop.

Until it reverses.

When the crypto markets collapsed, the company went from winning to fighting for survival remarkably quickly. The personalities did not change overnight. The environment did. And yet behavior changed almost immediately.

People who had been cooperative became territorial. Conversations became sharper. Information became political. Everyone started thinking about who would be blamed, who would survive, and where the exits were. It had a faint Lord of the Flies quality.

This taught me something uncomfortable about company culture. Some cultures are strong because the culture is strong. Others are strong because everyone is getting rich. It is difficult to tell which one you have while the number is going up.

There is another version of the same problem in venture-backed startups.

Sometimes a company raises a huge round, hires famous people, gets glowing press, and starts receiving all the social signals associated with winning before it has actually won anything.

This can be worse than losing. At least losing gives you information. Premature winning can remove it.

People begin optimizing for status inside the company instead of results outside it. Titles matter more. Territory matters more. Meetings multiply. Everyone has a theory of how the organization should work. The company begins behaving like the defending champion while it is still in preseason.

Money makes this easy. A startup with $3 million in the bank has to confront reality fairly often. A startup with $300 million can postpone the meeting.

So I’ve become suspicious of both winning and losing as sources of personal feedback.

If you are losing, you may conclude that you are bad when you are merely playing on a bad team. If you are winning, you may conclude that you are exceptional when you are merely standing in the right place.

The hardest career question may be figuring out what travels with you.

Did the deal happen because you negotiated brilliantly, or because the other side badly wanted your company as a customer? Did the product fail because you made bad decisions, or because the market was structurally hostile? Did everyone listen to you because your judgment was excellent, or because your title was impressive?

You rarely get a clean answer.

This is why changing teams can be so educational. The variables move around. You discover that something you thought was one of your great strengths was mostly institutional leverage. You also discover that something you blamed yourself for was nearly impossible from the beginning.

Both discoveries are useful.

I would still rather be on a winning team. Winning is more fun. It gives you resources. It attracts talented people. It lets you spend time building instead of constantly trying to avoid death.

But winning may be the more dangerous teacher.

Losing constantly tells you that you are not as powerful as you think. Winning constantly tells you that you are. Neither is entirely true.

The trick is to enjoy the wins without confusing the scoreboard for a personality test. Sometimes you made the play. Sometimes the offensive line gave you six seconds.

It helps to know the difference.