The Underrated & the Underdogs

I started off with many advantages, and yet — as is the case for most — I had less leverage at the beginning for my career than I have now and now still less than I hope to have in the future.

Less resources, less of a network, less know-how, fewer successes to point to to attract future teammates. (But a lot of energy, as is often true for people who have everything to prove.)

Over time things usually do become easier for these reasons. The only counterbalancing force is that I’ve seen many people have a big first success and then lose their hunger. Why not after all? Life’s good when you’ve made it. Why suffer trying to build new things? Why not just invest and live?

But not everyone slows down, and if the engine still runs just as strong, everything is now also in higher gear.

And yet, even though things have gotten a little easier, I have felt profoundly underrated at every point of my story so far. Like people never understood what I was doing, wanted to do, and was capable of. And I have always weirdly enjoyed this feeling, enjoyed being glanced over and disregarded compared to more obviously established people and brands. It’s not the only thing that motivates me but it has been a major force pushing me forward. I love that feeling of “us against the world,” a few misfits hacking away in a garage somewhere. And frankly I think that a lot of the great stories are born this way.

At least in my experience, the most successful companies I have helped start or investments I’ve made have been in teaming up with people unknown to the world, also possessed with the underdog mentality. People who were ignored or overlooked for a long time.

Take my friend Krishna from Catalina Crunch, now a nationwide brand. Krishna and I became friends hacking on some web apps together in New York, back when he was trying to start an auto-insurance company and I was figuring out what startup I wanted to work on, putting together one Rails app after another and trying to drive traffic to them. For more than a year after quitting his quant hedge fund job, Krishna tried to raise money and attract partners for this auto-insurance idea and wasn’t able to.

After a while, he totally changed directions and decided to create a healthy keto food brand, based on his own experience and needs as a diabetic. With no previous experience, he started baking cereal in his tiny NY studio. When he tried to raise money for that, showing up to meetings in his shorts and flip flops and extremely “relaxed” style, he was entirely overlooked. I had the advantage of knowing him well and having sat next to him coding together and seeing him not get up from his chair for 10 hours straight. I knew he was brilliant and a workhorse and that it just wasn’t obvious to the world yet. So I was lucky enough to be his first investor.

People like Krishna will grind harder than anyone else. They are not fancy or entitled and usually are scrappy as hell. Even to this day Krishna runs his company in an incredibly cautious and capital efficient way. I really do believe that the Krishna’s of the world are the best types of entrepreneurs. They continue to be underdogs. I have a dozen more examples that I’ll share some other time.

You of course have stories of senior executives at known companies starting very successful new things, but you also have many examples of grittier, less fancy teams starting off with a lot less funding and just making it work. You see very rich people try to incubate new things with hundreds of millions or sometimes even billions and those usually don’t end up anywhere. Too much money, too many fancy people, no urgency, no grit, no burning desire to prove everyone wrong. I think there has to be some sort of law of nature that favors the scrappy.

Being able to retain this underdog quality as you find success is invaluable. More resources can make you more powerful but more comfort will make you weak.

Back when I started working on startups and investing, almost no one sent me anything. I was living in San Francisco and — fair enough — there was no reason for an established VC firm to include me in an investment. Then I moved to New York and met a few people who were nice and made room for me (people like Ryan Darnell and Shana Fisher and Nick Chirls) — this of course is a great tell of their character… What was in it for them? It so happens that they are some of the very best early investors I know.

Every week I have people underestimate me and the teams I work with, and I hope it stays this way. (I also have people in my life who keep believing in us and opening doors in whatever way they can.)

But it’s nice to be shunned at a cocktail party or get the door shut in your face once in a while. It means you’re continuing to push out of your comfort zone, continuing to reach further even as the resources available to you expand. And it’s a great motivating reminder that you have to recreate yourself every day and that you certainly have not arrived.

Nothing is earned for good.

Everything has to be fought for day after the day, in the trenches, with your people.