Lenny Rachitsky: evaluation

Transcript context

…Again, this is one of those where I like to give very bespoke nuanced advice on a case by case basis to the folks in YC. But again, just to give you a preview of how I would think about it, I would look at how many more ideas the founder has on how to make it grow. If it's not going well and you're out of ideas, that is usually a good time to pivot. But when you have half a dozen or a dozen really good growth ideas that you haven't tried yet, try them. Right? Hey, give it a shot. Again, in the Airbnb story, right? They tried all sorts of stuff including cereal and conventions. They had a bunch of zany ideas on growth and they didn't run out of them. And so I think when there's still gas in the tank on an idea that might be a reason to stay the course. And when literally the founder is like, "Yeah, I don't know, I guess maybe we should pay influencers or something." When that's the kind of ideas they're coming up with, that might be a better sign to pivot. That is incredibly helpful. Coming back to Zip real quick, they went through I think six different pivots before they landed on this idea that is now a billion-dollar business. Is there anything from that specific journey that you found really interesting? Because they went in so many different directions like accounting, marketplaces and- Yeah. I think in the example of the Zip founders, they were both such great experts and I knew Rujul really well. He actually worked with me at YC as a visiting partner. And so I was really close to Rujul and he had done this marketplace called FlightCar when he was younger, which was raised a series B, it didn't work out, but it was a really cool company. And I had a lot of confidence in his competence on running a business and executing fast and just having great instincts. He really knows the fundamentals and the problem was they weren't as clear on what market to go into, is still with me. And so I actually suggested to do something in their case, again, this is very bespoke, but my suggestion was to start by looking at what companies are publicly traded and/or owned by private equity that are large and that also are hated by their customers, and to try to intentionally find where there's a knowable big market within incumbent combined with the software is horrible. And they did that. They basically found out about all this procurement software and what the state of the art was and that was the prompt. Again, maybe he told you this, that was basically the process.…

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