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.
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
Watch Full EpisodeStructural problems masquerade as people problems
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.
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.
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?
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.
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.
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.
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.