I'm a three-time founder, and what I do now grew straight out of that. Even when I was running my own companies, I enjoyed talking to my founder friends about their businesses more than I enjoyed talking about my own, for better or worse. I always loved helping people solve their basic business problems, giving them an outside perspective and helping them figure out a new angle. And then one day I realized I was actually good at it.

At this point it's become a hobby more than anything. I always say some people do Sudoku, I do startup mentorship. It's my half hour a day, or a couple of days a week, that genuinely helps me think outside the box, tackle different problems, and learn about new ones. There are so many industries out there I didn't even know existed, and they're fascinating. You start finding these weird threads that jump between them. That's why I mentor, and as far as I can see, I'll keep doing it.

One happened recently. I had a mentee building an AI coach that jumps into meetings to understand team dynamics, basically to tell you whether you're being a good manager. Great product if it works, but it wasn't really solving a pain point. It was a nice-to-have, like knowing I should be working out but telling myself I'll get to it tomorrow. Without a pain, it's hard to sell.

Then one quick switch: why not point the same tool at customer success teams instead? Rather than looking inward to manage internal dynamics, you build the same collaboration tool but aimed outward, at the relationship with your customers. That was an aha moment we both had at once, and we immediately started running with it. How do we test this, where does it go, who can we use? I even pulled people out of my own network to help her build it. That's what mentorship really is. It's not just the advice, it's the other little cards you get to pull out.

It's mostly one-winged. I don't have a set process or a fixed list of questions. The reality is that when you're talking to a founder, sometimes they don't even understand the core problem they have. Someone told me the other day, look, we really need to get to product-led growth, how do I grow on my product? And I had to say, you don't have product-market fit yet. You need a product people want before you can grow on it.

So my process is to ask questions until I get down to the core, and then we solve that, because everything else is a symptom. If you're not getting enough marketing conversions, maybe you're going after the wrong ICP, so what have you actually done to prove you've got the right customer? It's scratching down into the core of the onion to find what's rotten before you build it back up. I don't prepare much beyond reading what the problem is. It's a bit like being a doctor: the years of experience are just there, and the right question pulls out the part that's relevant.

I always recommend The Mom Test. The number of people who don't know that book surprises me, because if you're going to start a business it seems like the best place to start. It's a constant fallback for me. The other one is an analogy: Amazon started with books. You don't need to take over the world with your first idea. Find the one good idea you have and work on that before expanding into everything else.

I learned that one the hard way. I had a company fail because I tried to go too general too quickly. I had a small core of users who really, really loved the product, and if I'd just doubled down on them I bet it would still be alive today instead of dead in a ditch. So now I always come back to it: find your ICP, look at where it's going, and grow from a small, solid base. Amazon started with books is something most people can get their head around, and it sticks.