The other day, I got to thinking about how starting a company can be like playing bridge. I know I’m speaking to an extremely niche audience here—the Venn diagram overlap of entrepreneurs and bridge players is not particularly great—but hey, this is my blog, so bear with me.
Solo bootstrapping is playing 1 NT. You look down at your hand and see you’ve got an Ace, King, Queen or Jack in every suit, and no voids. It’s not a knockout hand, but it’s pretty good: 15+ high-card points and at least 2-3 cards in every suit. You think, hey, this looks pretty balanced and I’ve got strengths in every suit…maybe I’ve got enough here that this could be good.
You bid 1 No Trump.
Hopefully, you think, maybe you’ll find a partner — a co-founder, an investor— who can bring this to the next level, or to the big leagues. The person to your left passes. Your partner comes… and instead of giving you a suit or raising you… just passes. No support whatsoever. The person to their right passes. Looking around the table and realizing you’re the only one who’s got anything, you pass, and resign yourself to playing 1 No Trump without the support of a partner.
They lay down their cards, and somehow, they’ve only got cards under 10 in every suit. You’re on your own.
Any bridge player can tell you that 1 No Trump is probably one of the hardest hands to play and win. It requires attention to every single card. There is no room for error. You have to count each suit and know where every card is. To make it work, you need to be a high-performing generalist.
Bootstrapping with a co-founder is playing 2-3 of a suit. You look down at your hand. You’ve got 13 points and one suit that looks pretty good — 4-5 cards with maybe an ace and a jack. You can’t make a 1 bid on your own, but with the right partner, perhaps this could work. Let’s say it’s hearts.
You bid 1 heart.
The bidding gets to your partner, and they bid… 2 hearts. Alright. Not quite what you hoped for, but they’ve got enough to say something back, and maybe a few hearts. You take a chance and say 3 hearts, thinking that between the two of you, you can cover each other’s gaps and make it work. Maybe if you’re really strong together, you end up at 3NT and build a $5-10M+ ARR company. It’s hard as fuck but it’s possible. Congratulations, you’ve won the game.
In rare cases, you might find yourself with that 15+ point hand, and a partner who’s also got decent points, and take it to game (i.e. 4 level). This is your Wistia and Basecamps of the world: two co-founders who make a powerful combination and can create a $25M+ ARR bootstrapped business.
Taking funding after bootstrapping is a jump-shift. Maybe you were ready to play 1 NT on your own if you had to. But maybe… sometimes your 1 NT gets a 3 spades response. They’re powerful in a way that you aren’t and in a way that can really help you level up. Alright, let’s play a suit and go to game. You’ve got the fundamentals, and now you have a partner—an investor—who can help you specialize and pull in some serious points with what you’ve got.
Maybe it turns out spades are your best suit even though you’re pretty balanced. If your partner has 5 spades and you’ve got 4, you could end up at 4 or even 5 and go big. This is Laravel taking $57M from Accel.
Getting acquired after Series A is playing 4 of a suit. You bid one suit, your partner bids another, and between the two of you, you’ve got game and then some. Maybe you can’t get to slam—intergenerational wealth— but you’re walking away with high tens of millions of dollars at a minimum and you’re set for life. Play it well and you’ve won the game.
Series A-Z to IPO is a slam. You open with 1 NT… and get 4NT back. Blackwood, baby. You figure out how many aces you have between you, and go to town. You’re ready to go to town and take every trick and dominate the market. This is an extremely high-stress hand to play, but whew, is it a rush, and you get alllllll the points in the end if you pull it off. You’re set for life and then some.
No matter what hand you’re dealt or whether you’ve got support from a partner or not, bridge and business both boil down to the same fundamentals: making your best guess at might work, seeing what you have in front of you, deciding on a strategy, and executing.
Sometimes you have to be creative. Maybe you’ve got to finesse a queen.
Sometimes you need luck. Perhaps you need to pray for good distribution.
Sometimes you do a lot better than you planned on. Perhaps you bid two and end up taking four.
And sometimes you lose. 3 hearts seemed doable but you got burned on distribution or your finesse failed. Maybe you mis-bid. It happens.
It’s the hand you’re dealt and how you play it.