A very smart professor of mine once thought "They added pictures to hypertext, that's sort of cool I guess."
Looking backwards definitely biases you to seeing things you didn't see at the time. Even memories get tinged. But memories are probably the most accurate you can do.
I missed bitcoin entirely despite knowing many people who bought as I still don't understand what the appeal is. It doesn't seem efficient to me as a payments technology or from a privacy perspective. I kind of wish I bought early even though I probably would have cashed out way too soon, as the money would have been nice.
I liked Stripe due to my revulsion to PayPal but wasn't exactly going to be on them winning. I was pleasantly surprised. Ditto Shopify because of my dislike of Amazon stores. I think I underestimate the chances of good ideas and good products winning because I know it's very hard.
I took a few bets early in my career on start-ups. I think I underestimated the difficulty of selling into retail on one company that I still think had a good idea. The others ended up being acquisitions, although the products weren't continued. I still believe social notetaking is an interesting hard problem in need of a good solution but I don't think we had found it.
I think the big lesson for me is to not get taken in by the cult of personality around strong founders and focus more on the merits of the ideas. That can be tricky as you're not getting the full picture when you interview making it even harder to see a crazy idea as good for the right reasons but it's the right approach.
Looking backwards definitely biases you to seeing things you didn't see at the time. Even memories get tinged. But memories are probably the most accurate you can do.
I missed bitcoin entirely despite knowing many people who bought as I still don't understand what the appeal is. It doesn't seem efficient to me as a payments technology or from a privacy perspective. I kind of wish I bought early even though I probably would have cashed out way too soon, as the money would have been nice.
I liked Stripe due to my revulsion to PayPal but wasn't exactly going to be on them winning. I was pleasantly surprised. Ditto Shopify because of my dislike of Amazon stores. I think I underestimate the chances of good ideas and good products winning because I know it's very hard.
I took a few bets early in my career on start-ups. I think I underestimated the difficulty of selling into retail on one company that I still think had a good idea. The others ended up being acquisitions, although the products weren't continued. I still believe social notetaking is an interesting hard problem in need of a good solution but I don't think we had found it.
I think the big lesson for me is to not get taken in by the cult of personality around strong founders and focus more on the merits of the ideas. That can be tricky as you're not getting the full picture when you interview making it even harder to see a crazy idea as good for the right reasons but it's the right approach.