Lenny Distilled

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

July 03, 2025

Featuring: Andrew Wilkinson (Co-founder and CEO, Tiny)

8 quotes · 8 insights

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Structural problems masquerade as people problems

There are no problems. There is only people problems. As long as I'm surrounded by really great smart people, I feel fine. But when we have a bad actor, we have a psycho or a narcissist or a really horrible, difficult person we're dealing with, all bets are off.
Andrew WilkinsonCo-founder and CEO, Tiny 00:38:12

Build for 10x transformation, not incremental improvement

I think the biggest thing that a lot of entrepreneurs miss. They say, 'I don't want to do that for the rest of my life. I don't want to be in the back of a dry cleaner dry cleaning clothes.' And to me it's just a question of scale.
Andrew WilkinsonCo-founder and CEO, Tiny 00:11:26

Big bets require accepting failure as the price of breakthrough success

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 WilkinsonCo-founder and CEO, Tiny 00:00:00

AI is reshaping everything - adapt urgently or become obsolete

I think the fundamental question is, do all jobs just become a single prompt? For example, does a CEO just grow the business while making the customers happy and turning a profit or something like that?
Andrew WilkinsonCo-founder and CEO, Tiny 00:00:38

Hire for potential and hunger, not just experience

I've never been able to change someone. You can never mentor someone out into being a good employee. I think you need to hire someone who already is fully formed and can do what you need.
Andrew WilkinsonCo-founder and CEO, Tiny 00:38:12

Detachment from outcomes improves performance

No amount of money or success or attention or anything else had done what this little tiny yellow pill could do for my mental state.
Andrew WilkinsonCo-founder and CEO, Tiny 01:13:01

Fire fast when you know it's not working

The kind of heuristic I have is if I ever think, should I fire this person even once, I should fire them immediately. When someone's a superstar, I can't imagine firing them. I think it's impossible, I'd be lost without them.
Andrew WilkinsonCo-founder and CEO, Tiny 00:38:12

Hard choices now prevent harder problems later

Easy choices, hard life. Hard choices, easy life. I often find that anytime that I'm making the easy choice, my life gets hard. And when I make the hard choice to shut down the business, fire the person, say bye to a project that I was excited about, it's almost always the right choice.
Andrew WilkinsonCo-founder and CEO, Tiny 01:24:07

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