There are tournaments everywhere–jobs, admissions, promotions, startup funding. Are you playing the game? — Tournaments are everywhere in life. And the sooner you can identify them, the better you can compete. College admissions, getting into grad school, getting your first job, raising money, hiring a team, making partner at a law firm, getting promoted to executive, getting YouTube subscribers, getting tenure as a…

Being first doesn’t matter— but you do need to be better, faster, or cheaper. — Should you work on a startup idea that already exists? Well, Snapchat wasn’t the first messaging app, Facebook wasn’t the first social network and Discord wasn’t the first chat app. You don’t have to be first, but you do need to…

Autonomous car with no safety driver for $50M, not $10B — You’ve heard of Waymo and Cruise (Initialized was actually an early seed investor in Cruise, too). Each of those teams has spent more than $10 billion to deliver something that can drive normal roads without a safety driver. But there’s another way, and I’m excited to share that with…

Just because co-CEO worked for Google doesn’t mean it will for your startup — Picture this… it’s 2010, and me and my co-founder are pitching on Sand Hill Road. We’re sitting in the offices of Andreessen Horowitz, pitching Marc Andreessen and Ben Horowitz. We thought it was going fun, just like the others. Ben turns to us and asks, “Who’s the CEO?” I…

Software is coming to revolutionize global trade finance — Drip Capital started as two people with an idea in 2015. Today, they have over 138 employees, have raised more than $45M, and will do more than $1 billion in trade volume since inception by the end of 2020. They have over 2,000 importers and exporters on the platform…

Often the easiest choice is to make no choice at all, but you might kill your startup that way — Picture this… we were raising our Series A for my startup Posterous. My co-founders and I were at Benchmark Capital on Sand Hill Road, meeting with Peter Fenton, legendary investor in Twitter and Yelp. We think it’s going fine until Peter asks this question. So, are you a platform…

They build long-lived teams that beat all competition — How long do you think it takes to win a championship? Did you know that it takes a pro-level basketball team an average of 4.5 years to maximize their odds of winning a championship? Today we’re talking about teams and how teams win championships together. …

A guide to learning, earning, and minimizing regret — There’s an episode in Star Trek: The Next Generation where Captain Jean-Luc Picard never makes it past Lieutenant junior grade— a low level astrophysics engineer. He was “thorough, dedicated . . . steady, reliable, punctual.” …

Even Steve Jobs couldn’t contain his rage when his team failed— but you can choose to do better. — When I do a bad job, I feel shame. I feel worthless and it makes me feel worthy of only being abandoned. And if this is you, hey, you’re not alone. And yet shame is a part of a functioning society. University of Texas, Austin, psychology researcher, Daniel Sznycer…