Matt MacInnis: evaluation

Transcript context

…Okay. And then with Rippling, complete opposite, extreme product market fit, up and to the right. What's something you've learned about just that that you think people maybe don't understand about what it feels like, what it takes to get to product market fit, how things change? There's a line that this venture capitalist, whose name I will not mention, said, which was that product market fit is a sort of thing where you absolutely know it when you see it, and therefore if you don't absolutely know it, you don't have it. And this kind of gets back to my point about learning from mistakes versus successes. It's like, ah, man, over and over again, over the course of the many years that I spent at Inkling, we thought we had it. We thought we had product market fit, maybe, maybe. And in hindsight, with the benefit of now having experienced solid product market fit, it was so, so obvious that we didn't. And I've invested in like 60 companies or 70 companies. I don't know, it's not something I actively do. But opportunities, by virtue, I think, of my role at Rippling, sort of show up. And I talk to lots of entrepreneurs and I love it and I find it super stimulating and I love the fresh ideas and it's just something I do as a real cherry on top of the sport that I play already. But when I get the investor updates for the guys who've been at it for like three, four years and I read the updates from them that I sent to my investors in 2011 and 2012, I'm kind of heartbroken. We talk in Silicon Valley about never quit, but that is complete absolute venture capital bullshit. The incentive of venture capitalist is to put money into your company and milk you dry. They never get their money back. There is no way for them to take that investment back. So the only logical desire that they would have is for you to keep trying against all odds because there is the occasional example where someone pivoted from A to X and it was wildly different and it worked. Slack was originally some sort of a gaming company and became corporate chat. Airbnb maybe. It's like there's some examples of companies having made wild pivots and succeeded, but man, is that rare. Just so exceedingly rare. And I think it's important to remember, I'm 45 years old, we're going to be on the planet, the average age of a man in the United States when he dies is something in the mid 70s. I got 20, 30, maybe if I'm lucky, 40 years left on the planet. Very conscious of the time that I have. And I don't regret what I did at Inkling, I learned a lot. It informed what I do now. I don't think the chapter I'm in right now could have come without the chapters before it. So it's a beautiful, wonderful thing that I did what I did. But when I read the investor update and I'm like, "You're where I was and you are not getting out of this." The Silicon Valley try until you die mindset is not pro-entrepreneur, it's pro-venture capitalist. And I know why that is, but I think it's important to say out loud that you should fucking quit. You should reset the clock, you should reset the cap table because trust me, product market fit when it arrives is insane and it's exciting and you should pursue it. And never delude yourself into believing you have it when you don't. ould reset the cap table because trust me, product market fit when it arrives is insane and it's exciting and you should pursue it. And never delude yourself into believing you have it when you don't. It is dangerous and regrettable. How's that for a speech?…

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