On luck, judgment, and saying no to twelve million bucks

We cherish some memories. We want to forget others. And now and then, there’s a weird third kind that fits both buckets. 

I was digging through my Gmail the other day looking for a message, and I stumbled across an email from April 2011. 

A job offer that I rejected. 

Just before Airbnb announced its Series B in 2011, I was offered a mid-level growth marketing role. The salary was $68K, plus stock options vesting over four years that represented about 0.02% of the company. They wanted me to start within four to six weeks. 

I declined… to start my own aviation social media consultancy (RIP AIRticulate, but what a name 😂). I ended up making about enough from that venture to pay off my $23,000 Mitsubishi Galant, “Dr. Platinum,” and buy a few index funds. At the time, it felt like a win. 

Those stock options I turned down, though…they would be worth somewhere between $12 and $13 million today. 

The obvious lesson is that I made a bad call…an aww shucks, “what if” kind of tragedy. I’m not sure that’s the right lesson. 

Remember, this was April 2011. Airbnb wasn’t Airbnb yet. It definitely wasn’t a verb. They had around 75 people, and nothing obvious signaled what they would become. All I saw was a modest base salary in an expensive city, with some options that probably wouldn’t amount to much. When they raised a $112M Series B a few months later, I never really registered what that meant. 

I was comparing salaries and autonomy, not thinking about power laws. And I had already decided what I was going to try. I was speaking in Cannes that month! (At a nerdy aviation tech conference hosted by Amadeus, mind you. Nothing to do with films or fashion or the arts. But come on, airfare plus a free hotel in Cannes!)

Maybe it was a stupid decision in hindsight. But if I’m going to judge it fairly, the question to reflect on isn’t what happened next? It’s what could I have known? There’s one thing about it I regret, and it’s not the money. 

When I sent the old thanks-but-no-thanks, I had a pretty good idea of what Airbnb was, but I didn’t know who they were. I understood the business. I had ideas for how I could help them grow. But I hadn’t heard the now-infamous story of Obama O’s and Cap’n McCain’s. I failed to account for what was probably the most important data point: the grit and creativity of Brian and Joe as founders.

And honestly, knowing that probably wouldn’t have changed my decision anyway. As far as I was concerned, I was just as gritty and creative, and I was hacking out my own path. But I regret that I didn’t even think to ask the question.

Today I can point to 73 ways I was not as gritty or creative as Brian and Joe. In 2011, I couldn’t see the gap, because I didn’t yet know what that level of grit looked like. You don’t know what you don’t know. And a free trip to Cannes felt like real-time validation that I was on the right path.

So the “right” decision wasn’t really available to me. Which raises a set of questions I find more interesting than the $12 million:

1. What would have had to be true for me to say yes to Airbnb?
2. And if I had said yes, what exactly would people have been praising?

Here’s how that would have really had to play out: I would have had to miss a few random encounters that led to invitations to speak in the niche world of travel tech, which led to the idea that I could turn that stage into a good business, which led to the perhaps irrational confidence that I could pull it off. In other words, the answer to 1) is that I would have had to put myself out there less and be less self-confident, choosing the “safer,” more obvious path. 

If all that had been true and I had sent a different email in April 2011, I’d be mostly the same person. Same brain, same work ethic, same blind spots. But my resume would tell a completely different story. The post-rationalized narrative would have been about judgment: “he saw it early,” like I had some clear lens into the future. But that wouldn’t have been true at all. I would have simply been in the building when it happened because I hadn’t yet imagined another path.

That’s true for more people than we like to admit. Brian and Joe aside, plenty of early employees had careers supercharged and lives flipped upside down by being at Airbnb (and lots of other startups like it) at the right moment, and their stories now carry a halo of foresight that the moment itself may not have justified. 

I’ve sat on the other side of that table for years, and I’m sure I’ve made the same mistake: reading someone’s luck as foresight, or someone’s detour as a lack of it. We evaluate careers, and so much else in life, by outcomes, because outcomes are the easiest to see. The decision itself—the information available at the time, the timing, the proximity—those stay hidden. So we give people credit for the part they controlled least and ignore the part they controlled most.

If outcomes are such a poor proxy for judgment, then the only thing you can really build is how well you decide when you can’t see the ending. And the irony is that my “stupid” path gave me years of practice at exactly that: navigating non-linear, lightly traveled paths, and getting comfortable being uncomfortable. Rereading that email now, it’s almost exactly what Airbnb said they were looking for: people comfortable building, testing, and learning as they go. In a world where change keeps accelerating, all gas no brakes, that might be worth more than I gave it credit for.

And it gave me more than a skill. I’ve lived and worked on multiple continents, built a life in Tokyo, and collected random experiences I’m not sure I’d have found from a desk in San Francisco.

Maybe not $12 million more. But more.