I have never been an investor, but I have been a consultant who focused on short-term, strategically important projects for startups. So I got to see a lot of companies, both successful and unsuccessful.
After a while, patterns really do become obvious. When you've seen some winners, and some doomed companies, and some that will just muddle along forever, you start to notice things.
One thing is that when your customer base is truly energized, they'll practically crawl over your desk to write checks. With other companies, you'll need a sales team to push things uphill. But those companies can still win, if the sales department is humming. Other companies have poured their heart into their product, but they've never figured out how to sell it, or even how to talk to customers. (I can fix product problems, but I can't fix teams that don't talk to their customers.)
Sometimes all it takes is a 5 minute phone call with a founder, and you can tell which is which. I've turned down pretty generously funded projects because it was clear that no amount of software would help a particular company connect with its market.
Now, a successful investor has seen far more companies than I ever saw. I imagine the best investors can filter quickly and surprisingly well.
The learnings:
1. The number of companies of a batch affect how YC should work
2. Bad founders don’t understand what problems they have (or miscalculate its relevance)
3. Founders don’t listen
None of those come from listening to founders. Number 1 not even came from founders, it was an internal realization that didn’t affect founders.
It was kind of interesting to read, just odd due to its title and hook.