One morning recently, while beset with jetlag, my daughter and I awoke very early. The sun had not yet risen, and we passed the time by playing a game of Uno. As we played, we discussed some of the strategies one could use while playing to best set them up for success.

This particular game lasted over half an hour, which is uncharacteristically long in my experience. And in that time, I began musing about how there exist parallels between those same strategies we were discussing and my own experience as a startup founder.

Most of what I write is about the intersection of business, politics, or technology with concepts in science and math. In this particular case though, I found that another unexpected intersection exists: between the lessons it took me years to learn as a startup founder and the lessons I discussed with my daughter during a thirty minute game of Uno.

I’ve played countless games of Uno over the years where I had tons of greens, a perfect steady stream of one color to take me to the finish line… only to find that the top card in the discard pile was any color but green.

I’ve seen the same happen in my own startup journey, and in those of many other founders. You may have something amazing in hand, but if it’s not what the world needs at that particular moment in time, it has little to no value.

They say timing is everything, and this is true both in entrepreneurship and in Uno. Timing is what determines what has value and what doesn’t. But there is a counter-lesson to be gleaned here too: Just because what you have doesn’t have value today, doesn’t mean it won’t one day in the future. All it takes is for one green card to make it to the discard pile.

One of the most interesting aspects of Uno is that the game becomes increasingly complex and competitive as you logically deduce information about your opponent’s hand. For instance, when I play a red card and my opponent takes from the draw pile, I can conclude that they don’t have any red cards. If I play a six, and they draw, they lack sixes. And those pieces of information become more valuable as I choose which cards to play on subsequent hands.

The same is true in business. Starting a new initiative of any kind doesn’t exist in a vacuum. It exists in a space inhabited by legacy players, competing interests, and both divergent and convergent strategies. And it takes time and patience to understand these factors through careful observation of what people do and don’t do. No one is going to show you their hand. But that doesn’t mean you can’t figure out what they’re holding.

When I was young, a wild card in Uno, like a joker in any card game, was thrilling. And playing it was a power move. Yet I have come to learn that the power of a wild card isn’t in its short term impact but in its ability to serve as a safety net.

I cannot understate the importance of safety nets in startup life. As I and others have learned the hard way, most early assumptions one makes are bound to be wrong. It takes time to course correct. Moreover, the journey is long, and during that time, the macro environment will undergo dramatic swings (whether the cause be the economy, the state of the competition, or something entirely unpredictable and cataclysmic like COVID). Saving money in the bank and preserving lots of optionality may seem less glamorous than audaciously playing that wild card when you draw it… But it could mean the difference between winning and losing in the long term.

Related to the notion of holding onto your wilds, in both Uno and startups, one’s decision tree can either have breadth or depth, but it can’t have both. In other words, you can either focus on the now by doubling down on something (such as a business decision or a particular color of card), or focus on the future by preserving optionality (via spreading resources across parallel strategies, or via holding onto each of the colors of cards so you always have something to play later on).

This tradeoff is tremendously tricky to navigate, and every company (and Uno player) faces it. I call it the Startup Uncertainty Principle (or, perhaps in the Uno case, the Color Uncertainty Principle).

When I played Uno against my daughter on that day at 4 AM, there were a number of times that one of us was down to only one card. It’s a good feeling when that happens, when you can proudly proclaim “Uno” and excitedly wait for that next card to be put down so you can win.

But what usually happens (right around three out of four times) is that you can’t put down your last card, because it’s not the color or the number you need.

My startup journey had a lot of ups and downs. They all do. And when you’re up, you can’t get too proud or excited. That’s because most of the time (much more than three out of four times), you’re not close to winning. In fact, you’re very far away.

But the silver lining? The downs shouldn’t get you too down either, because most of the time, you’re not that close to losing either.

One morning recently, while beset with jetlag, my daughter and I awoke very early. The sun had not yet risen, and we passed the time by playing a game of Uno. As we played, we discussed some of the strategies one could use while playing to best set them up for success.

This particular game lasted over half an hour, which is uncharacteristically long in my experience. And in that time, I began musing about how there exist parallels between those same strategies we were discussing and my own experience as a startup founder.

Most of what I write is about the intersection of business, politics, or technology with concepts in science and math. In this particular case though, I found that another unexpected intersection exists: between the lessons it took me years to learn as a startup founder and the lessons I discussed with my daughter during a thirty minute game of Uno.

I’ve played countless games of Uno over the years where I had tons of greens, a perfect steady stream of one color to take me to the finish line… only to find that the top card in the discard pile was any color but green.

I’ve seen the same happen in my own startup journey, and in those of many other founders. You may have something amazing in hand, but if it’s not what the world needs at that particular moment in time, it has little to no value.

They say timing is everything, and this is true both in entrepreneurship and in Uno. Timing is what determines what has value and what doesn’t. But there is a counter-lesson to be gleaned here too: Just because what you have doesn’t have value today, doesn’t mean it won’t one day in the future. All it takes is for one green card to make it to the discard pile.

One of the most interesting aspects of Uno is that the game becomes increasingly complex and competitive as you logically deduce information about your opponent’s hand. For instance, when I play a red card and my opponent takes from the draw pile, I can conclude that they don’t have any red cards. If I play a six, and they draw, they lack sixes. And those pieces of information become more valuable as I choose which cards to play on subsequent hands.

The same is true in business. Starting a new initiative of any kind doesn’t exist in a vacuum. It exists in a space inhabited by legacy players, competing interests, and both divergent and convergent strategies. And it takes time and patience to understand these factors through careful observation of what people do and don’t do. No one is going to show you their hand. But that doesn’t mean you can’t figure out what they’re holding.

When I was young, a wild card in Uno, like a joker in any card game, was thrilling. And playing it was a power move. Yet I have come to learn that the power of a wild card isn’t in its short term impact but in its ability to serve as a safety net.

I cannot understate the importance of safety nets in startup life. As I and others have learned the hard way, most early assumptions one makes are bound to be wrong. It takes time to course correct. Moreover, the journey is long, and during that time, the macro environment will undergo dramatic swings (whether the cause be the economy, the state of the competition, or something entirely unpredictable and cataclysmic like COVID). Saving money in the bank and preserving lots of optionality may seem less glamorous than audaciously playing that wild card when you draw it… But it could mean the difference between winning and losing in the long term.

Related to the notion of holding onto your wilds, in both Uno and startups, one’s decision tree can either have breadth or depth, but it can’t have both. In other words, you can either focus on the now by doubling down on something (such as a business decision or a particular color of card), or focus on the future by preserving optionality (via spreading resources across parallel strategies, or via holding onto each of the colors of cards so you always have something to play later on).

This tradeoff is tremendously tricky to navigate, and every company (and Uno player) faces it. I call it the Startup Uncertainty Principle (or, perhaps in the Uno case, the Color Uncertainty Principle).

When I played Uno against my daughter on that day at 4 AM, there were a number of times that one of us was down to only one card. It’s a good feeling when that happens, when you can proudly proclaim “Uno” and excitedly wait for that next card to be put down so you can win.

But what usually happens (right around three out of four times) is that you can’t put down your last card, because it’s not the color or the number you need.

My startup journey had a lot of ups and downs. They all do. And when you’re up, you can’t get too proud or excited. That’s because most of the time (much more than three out of four times), you’re not close to winning. In fact, you’re very far away.

But the silver lining? The downs shouldn’t get you too down either, because most of the time, you’re not that close to losing either.