Lenny Distilled

Big bets require accepting failure as the price of breakthrough success

Strategy → Prioritization

I'm a big believer in big bets, high risk, high reward. I don't get as excited about incremental things. But, I get excited about big bets. And if you make big bets, you're going to get a lot of it wrong.

Paul Adams What AI means for your product strategy

You either decide to pay the price or get out. Don't half-ass it. You see all these companies saying, we do AI and they've just sprinkle a little bit of crappy AI and they've got the same cultures. It won't work.

Eoghan McCabe How Intercom rose from the ashes by betting everything on AI
Supporting

Most of the time CEOs want options. They want to hedge their bets, but what you really want to do in these strategic inflection points is go all in one thing.

Drew Houston How embracing your emotions will accelerate your career | Joe Hudson (Art of Accomplishment)
Supporting

Concentration is what builds wealth, diversification is what preserves wealth. And you're a startup. You're not trying to preserve anything. You're trying to build something. It requires concentrated bets, not hedging.

Jag Duggal Be fundamentally different, not incrementally better
Supporting

Not taking bold risks, not making bold moves, it's a risk for itself. Many times people want the inertia, people want just the incremental value. But if you want to do leaps many times you need to let go of things that were successful for you in the past.

Daniel Lereya Daniel Lereya
Supporting

I would really love it if more people were like, 'Screw it. I'm going to do something that's probably going to fail. It's important and it's worth doing and I'm going to do it well.'

Hilary Gridley How to build a team that can "take a punch"
With caveats

You don't want to walk into the gym on day one and try and deadlift 300 pounds. So when someone comes to me and they're a first time entrepreneur and they say, 'I'm going to make the next great AI company,' I think that is the equivalent.

Andrew Wilkinson I've run 75+ businesses. Here's why you're probably chasing the wrong idea.
With caveats

If a software project could get built in two to three weeks, what does that really mean about the true complexity and differentiation of what you built? It's probably not very high, unless you believe you are way smarter than everyone else. But I think that's hubris.

Varun Mohan Building a magical AI code editor used by over 1m developers in 4 months: Inside Windsurf