Thanks for sharing Tim!
I had a similar(ish) experience when I was working out of V.G. back in ‘12-’13. We were working on an e-commerce product that neither of us were super interested in, and we’d just brought someone on part-time and had been about to put in significant personal cash and try to raise money.
However, we started doing some more intense customer research, and realized that there were some serious issues about our product mix and fulfillment process (shipping items from USA -> Japan was going to take 3–5 weeks, which people didn’t like).
In the end, though, it weren’t the specific problems we faced that led us to shut it down. We had some ideas about how to approach them. However, after 8–12 months of working on this in all our waking hours, we realized that we didn’t want to spend the next year of our lives working on a problem space we couldn’t care less about.
It definitely was rough emotionally, and there was a lot of self-doubt, but ultimately it was the right decision and paved the way for other, better opportunities to come along.
Also, in this day and age, I don’t think it makes a lot of sense to raise a seed round and then try and pivot your way to an idea that works. For most ideas, you can build out and test the tech with minimal resources, and it seems like raising money just serves to add pressure and constrain the space of problems (and solutions) you can explore.
I spend a lot of time with bootstrapped / lifestyle entrepreneurs nowadays, and also some time with people who have raised money. The way I think about it personally now is that I would only want to raise money if I already had product-market fit, I was looking to scale up, and money was the primary constraining factor.
Anyway, that’s my $0.02. Hope to connect next time I’m in Tokyo!