I disagree with him about " My best guess is that a truly great consumer service needs to be something that is can be used every day. " I use Wanderlog (YC19) almost every trip I do, a lot of my friends after I recommended this tool started using it. Yet it is kinda right - Wanderlog doesn't seem to be making big progress, although pandemic is probably responsible for that
[0] https://blog.garrytan.com/travel-planning-software-the-most-...
1) I would argue that that perspective misses a number of travel consumer apps like AirBnB.
2) I've bootstrapped this business and, while I do think that it could eventually morph into a regularly engaging social network or a tool for professional trip leaders (who would invalidate the limited usage point as power users), a healthy lifestyle business outcome would be reasonably ok (if not desirable) by me personally. I don't believe that I could have bootstrapped this company in 2012 (the date of that article) given the startup ecosystem and, frankly, this is a passion project after having previously worked at and founded SaaS fintech companies.
3) I do expect group travel to grow a ton over the next few years if people continue to work remotely. The evidence of mass social alienation is clear and folks have previously unheard of flexibility to travel.
2) It most likely won't lead to a successful social network because people mostly think about travel a handful of times per year. That was one of my tough learnings while working on Sherpa[0]. It could be a useful tool though! Maybe there's a solid B2B angle. Bootstrapping is also very smart. We tried to raise VC for Sherpa and ran out of runway.
3) I think you're right. There's probably something interesting there!
[0] - https://techcrunch.com/2017/06/02/sherpa-turns-instagrams-be...