Winning is a Habit
All Things Venture #088
A few weeks ago, I was at a work dinner in Soho with a bunch of my colleagues here at FirstMark. We were at a lowkey Italian spot off of Spring street, and it was a chance for myself and other team members to connect, to get to know each other better, and to get some career advice from one of our founding partners, Rick Heitzmann. We talked about a bunch of things that night. We talked about what this current paradigm shift (and hype cycle) in AI means for us as we evaluate investments. We talked about where our ambitions are as a firm, and how we can compete in this particular market. And on top of that, we talked about a bunch of other shit, like whether or not The Godfather is a top 5 movie of all time and if an Eight Sleep is actually a good investment. In any event, it was a great night. It was informative, casual, and fun and maybe most importantly - it didn’t drag on too long.
However, as we talked about all of the above, there was one piece of advice from Rick that stuck with me. It was in response to a question I asked him as we delved into more of the career-advice(y) portion of the night. In not so many words, I asked Rick basically what were the traits that he looked for when evaluating founders in the context of making investments, and his response was jarringly simple and familiar. He told me and the rest of the team there that, “Winning is a habit” and, “Winners win.”
The simplicity of the statement to me, lies in the fact that, investing is a game of capital allocation, risk tolerance, and qualitative and quantitative judgement. Here’s how legendary Howard Mark’s describes the process of investing in a similar manner:
Superior investment results can only stem from a better-than-average ability to figure out when risk taking will lead to gain and when it will end in loss. There is no alternative. Superior skill is an essential ingredient if superior investment results are to be achieved reliably. No tactic or technique will lead to superior results in the absence of superior judgment and implementation.
The familiarity of the statement comes from the fact that over the course of playing basketball competitively for nearly 20 plus years I have been similarly told by coaches, friends, and teammates at all levels, that winning players, make plays.
A very recent example of a “winners, winning” taking shape in the real world, is with Databricks’ $1.3bn acquisition of MosaicML. Now this example is important because Mosaic has barely been around the past two years, it’s an extremely fast exit and by all accounts a win within the world of venture. But what really makes this acquisition so representative of Rick’s advice is that for Naveen Rao, MosaicML’s CEO and Co-Founder, this isn’t his first sale of an AI company to a leading enterprise player.
This isn’t his first win.
In 2016, Naveen guided his first venture backed company, Nervana Systems, to a $400mm acquisition by Intel. According to LinkedIn, the business was started and sold in 2 years and 7 months.
The timeline for MosaicML?
The exact same thing.
Now obviously I’m not an insider here, I don’t know all of the details of how Mosaic or Nervana were built, nor do I ascribe to the ideology that every successful venture backed startup needs to be led by a second time founder (I’ve looked at the data, they don’t). But I think what is extremely important to takeaway today is, that at the end of the day, whether you’re an investor, a founder, or a startup operator we are all, in different but interconnected ways, playing a game. We are playing a game where if you win, you hit the money printer and you can go buy an island, or a sports team, or a second house or whatever. If you lose, you just get to keep working and take everything you learned about what didn’t work with you. But it is a game nonetheless that will prioritize, incentivize, and reward the individuals and teams that just figure out how to get shit done. We play a game that rewards, winners.
So play the game! Play it fiercely, play it with intent, play it with desperation. Play it in a manner where you fundamentally believe that you will never get to play again. Play with a foundational belief where your losses are merely training grounds for your future wins. Focus on building winning habits in whatever your domain is, become the expert in your field of choice, challenge yourself to go above and beyond, and hold yourself to a higher standard because the person in life that truly dictates your limits, is not the crowd, it’s not the individuals observing the arena, it’s you. We’re not all going to be the next Elon Musk, or Jeff Bezos, or Sergey Brin but there’s no barrier to trying. There’s no penalty to having steadfast belief in self. Sure you may rub people the wrong way at times, but I’ve never met a successful person that was universally well liked. Don’t be an asshole to people, that’s not what I’m saying but if you’re constantly winning, you’re going to have haters. At the end of the day though, what I love about the field of entrepreneurship and startups is that when these things work, your life can fundamentally change. When these things work, you will have an ability to direct resources against the problems you care about. When these things work, you can foster a culture that affects communities in an extremely positive way. So play the game. See how good you can be, see what the world is waiting for, from you and know that when you get your first big win, it’s probably not going to be your last.
That’s it for this week everyone. I promise I will try and put out articles more consistently. Big shout out goes to Rohit for being a helpful catalyst to get this particular one finished. Have a Happy July 4th and enjoy all the time off.