Should you rethink everything?
Why you should question...everything.
Many of the CEOs I am working with are facing some sort of existential crisis, largely driven by the impact or the opportunity of AI.
Their business could be growing nicely. They’re beating plan. Things are “working.”
But there is a gnawing feeling deep inside them that they are no longer on track or that everything has changed and they haven’t.
Every investor is feeling this too. What were once investable benchmarks for your next fundraise have changed. There will only be so many PE roll-up exit opportunities for your business.
Something needs to change.
If this resonates, consider doing a Radical Rethink of your business.
Start with asking yourself and your team:
1. What would you do if you were starting this business today?
Not tweaking what you have. Starting over. Same market, same insight, but no legacy code, no inherited processes, no sunk costs. Total blank slate. What do you actually build and how do you build it?
Would your team be the same size? Would pricing be different? Would you burn the boats?
2. If a pure AI-Native YC company launched today to compete with you, what would they be doing?
They’re not constrained by what you’ve already built. They have no installed base to protect. They’re using AI from day one. What does their version of your product look like, and how much time would you have before your customers notice?
3. What hard truth are you ignoring?
Every CEO I work with knows. There’s something they’re not saying out loud. About their product. Their team. Their competitive position. AI just made that thing more urgent, and maybe a Radical Rethink gives you the moment to change it.
4. Have you made any changes to your business because of AI?
Not “we’re exploring it” or “we have a working group.” Actual changes. To how you operate, what you build, who you hire, what you stop doing. What percent of your code is written by AI? How are you using AI to source and qualify your leads? Is AI accelerating your customer onboarding? These are table stakes today. If your team isn’t proactively driving this, you’re way behind.
5. Have you personally built anything with AI?
Not ChatGPT for emails. Built something. Automated something. Changed your own behavior. Because if you haven’t felt it yourself, you don’t actually know what you’re asking your team to do. I’ve written about that here.
6. How much runway do you have?
Once you get real clarity on the above, it’s time to think about how quickly you can get there. As one CEO said to me “I know what company I want to have in three months. Why not start today?!”
If you’re considering a Radical Rethink, please reach out, I’d love to help.
You got this.
LFG.
If this post helped you — or made you think of someone — please forward it. And let me know what resonated or missed. I read every reply.
#leadership #RealTalk #ceocoaching #HowToCEO #founder