If you're financially secure, why force it to stay in a position you don't enjoy? Besides, having a C-level title from a successful startup makes it a whole lot easier to get funding for the next thing you want to build...
Wishing him the best with whatever he's planned!
Edit: Typos
And yes, it's certainly a tradition that we hope to keep up!
(We're three equal founders and not all male, for what it's worth).
Their api is truly a piece of art and one of my favorite software projects to look at. I always find myself taking example from it when building an api.
Reading the preceding post to the one mentioned here, his decision suddenly seems not so surprising. Like his role in the sprint of building a company is done now and not all people make the transition once the company grows up to the next level
A few days back, I actually realized that I had never seen a talk by Greg, and actually googled for one, and found one about hiring at Stripe[0].
I can't wait to see what comes next.
Please fix the payments industry by building something that just plugs into a site without having to care if it's Stripe/Datacash/Paypal/Sagepay et al.
The costs of switching are too high in this industry and a "nicer API" isn't a good enough feature for any of my clients to want to switch. A product which lets customer failover and chase competitive pricing is what's needed.
The codebase you have contributed to (built), is just incredible.
I still owe you a 50lb bag of rice!
Larry and Sergey have been working on Google for 17 years. Mark has been working on Facebook for 11. Drew and Arash have now been working on Dropbox for 8 years. Brian, Nate, and Joe have been working on Airbnb for 7 years.
Things change, of course, and you shouldn't work on a company that isn't working for 10 years. But I think it's a reasonable question to ask.
If you go into something with a plan to do it for only a couple of years, you are unlikely to create anything important.
I don't buy public or private equities I don't want to hold for 10 years (I have held some Apple shares 17 years now!), and I don't do jobs I can't see myself doing for 10 years (I ran my company, which was an ok but certainly not huge success, for 7+ years).
I think more people would benefit from taking a long-term view on where they decide to spend their time and money--it's a really useful way to think about opportunity.
One of the benefits of the long term view is that it forces you to address sustainability, so you focus on real revenue.
Our startup is now 6 years old. We decided early on that chasing funding meant focussing on the wrong thing, and that we would suck up the pain of little income and slower growth. Being able to focus on the product instead of investors was great, but that slower growth also turned out to be healthy. It meant a better relationship with our first customers, which lead to more useful feedback, a better product, and organic growth that this year will give me 4 times the best salary I ever earned before.
And it's still fun - as well as the financial compensation, we still control 100% of the company so we can do things our own way. We employed one of our support people in a city hit by a devastating earthquake; we carried an agent for a few months while she escaped an abusive marriage; we make a sizeable donation to a kids' charity in lieu of sending out Christmas cards.
One way to counter this would be startup founders tweeting & sharing more but I know how little time you have for anything when you're building a business.
If a founder doesn't think a company will be worth running in 5 or 10 years what does it say about their long term plans for it? Are there many examples of successful start-ups where the founders left within the first few years?
And in any case I don't think it would change much if an investor knew with perfect foresight that AirBnB would be a $10 billion dollar company but one of the founders was planning on leaving after 7 years (or even 4). The same is true if it was a $100 million dollar company or a $0 company.
It seems to me what really matters is whether the founders will stick with it for the first 1-3 years when things are toughest.
(edit: And Larry and Sergei tried to cash out immediately).
I generally reply openly about my ten-year plan, I promise that it's going to change, and I restate how large a challenge it is to maintain excitement and interest at their company for the next ten years of my life.
I feel like the ambitious people (the kind that start these sort of companies) do not feel comfortable working on the same thing for more than a couple of years. They get that itch, understandably.
Quite obviously that question is more about how you answer than it is about what you answer.
He's trying to escape his failure. DO NOT TRUST