When’s the Right Time to Jump?

So the first question, how did you know it was the right time to start a company? I'll tell you a couple things. One is don't be in a rush. So much about Silicon Valley, I think, insists that we as entrepreneurs must do things faster, must do things younger. Whether it's Peter Thiel and the Thiel fellows saying, don't even go to college, or it's Y Combinator saying, screw normal jobs, just come in and do this incubator thing. The sort of ethos is to go faster and faster and being younger and younger. But it doesn't have to be that way, right? If the stars align for you, and that's true for you, great. But they didn't for me. I mean, I was 31 years old when I started my company, and I had been through an incredible arc of a career that gave me a really great base of knowledge and a network, Right? It was frankly, that network that allowed me to get the offer of being an entrepreneur in residence, that gave us the this sort of backbone that we needed to build an enterprise software business. So I'd say, don't be in a rush. The second thing I'll tell you is there's no right time. So at Google, this was at the September 2008, my co founder and I had reunited. So he was one of my former tech leads. We knew we liked each other, we liked working together, we had shipped some really impressive products together, and we both wanted to start a company and we were both ready. The time was right. And so we had worked on some ideas, we had a handful of ideas, one of which became telepart. And we turned in our resignation at Google, and there was just one little problem, which is, as you can see from this chart, it was like the worst time to leave your cushy big company job. This was two weeks before Lehman Brothers blew up, right? Like, anybody who was kind of plugged into what was going on was probably stockpiling like tuna and dog food for the end of days. And we're just like, yeah, sounds great. Forget the free food and the stock options and everything. Let's just go out on our own. And it's funny now, looking back, I sometimes think, what were we thinking? And yet the act of entrepreneurship is so difficult. No matter what, there is no right time. Reid Hoffman, who's one of my partners at Greylock, likens it to jumping off a cliff and building an airplane on the way down. Elon Musk says it a little more morosely where he says, starting a company is like Eating glass and staring into the abyss of death. So to the extent that is true, and it feels like that from time to time, there's basically no good time to start a company. But there's also no bad time to start a company. And if you start a company when the consumer confidence index is at its lowest point it's been in decades, the nice byproduct of that is that there's kind of only one way to go. And yes, I did Photoshop Drake's head on an emoji, but really you get steeped in how bad things are and then things just keep getting better and you get this tailwind at your back. So there's no right time. And the worst times can also be the best times. The other thing I'll say about how you know it's the right time is when you can surround yourself with people who have yes energy. Not yes people, not people who aren't challenging you. But by and large, whether it's your co founder or in this case James Slavitt, who is now our managing partner at Greylock and was our sponsor as entrepreneurs in residence at Greylock, he is the kind of individual who just like they exude this yes energy, right? You bring him an idea and he says yes if or yes and. But it starts with a yes, right? It's not this skeptical, like no cross arms view of the world. It's like, yeah, actually I think I believe in you guys. Like you're smart, you're from Google, you can probably figure it out. Why don't you come in and like use one of our offices here at Greylock for you know, for a few months until you get your feet under you. Just that yes energy is really empowering as an entrepreneur. So I implore you, encourage you to seek it out. And then I'll offer you this statement that has proven very valuable for me over the past year, which is simply everything you want is on the other side of fear. So there will be a point at which the stars are aligning. You found your co founder, you have the idea, maybe you've been offered some seed money or an entrepreneur in residence position, something the universe is conspiring with you and then you will be gripped by, by fear because you're about to jump off the cliff, right? In a proverbial sense. And I just, I really, really believe that when at that moment you can just like say this mantra, everything you want is on the other side of fear. How do we get what we want? Let's get on the other side of fear. Let's just go for it.