Right. But again, the tech giant is also buying you because you’re a founder who has had some amount of success. The reverence for the founder might sound silly, but it’s based on something real, which is that it’s really hard to measure why a company is successful.
There are too many factors at play: market timing, staffing decisions, choices about the technology stack. It’s impossible to know why a particular startup succeeds. So you find something to control for, and that’s the people. That’s why big tech companies like to bet on founders. This is something I’ve noticed in my career: there are people who are just very effective, and the things they touch seem to work. And most people aren’t like that.How have your views of the acquisition experience, and of the tech industry more broadly, changed over time?
I felt I was succeeding while the acquisition was happening. I had worked hard and I was being rewarded for it. The system was working.
But today I look back and think of it as a failure. Why didn’t I work on something more challenging? Why didn’t I take a bigger swing? At the time, I thought I was working on something groundbreaking. Now, with some hindsight and maturity, I think I just got lucky doing something small.
I definitely feel like this was a silly chapter in my life. I’m very glad I got to pay off my student loans. But I don’t feel good about the work. In fact, I feel pretty embarrassed about it.
It’s not that I consider myself a failure for not having built a successful business. The failure I feel is more personal: it’s that I spent my time on building a small social app instead of something that would have been more meaningful.What would’ve been more meaningful?
I could have worked on something that actually had a positive impact on society. Or I could’ve set out to solve a problem that had more interesting technology behind it.
Making the World a Better PlaceWhat do you think changed your mind? Because you didn’t feel that way at first.
I think it was seeing more of the industry, spending time at these big companies, and observing certain things.
One of those had to do with bias. Silicon Valley has been under attack for the past several years for having a lot of bias in its compensation practices around gender and race. As a result, the big companies have tried to standardize the way they pay people. They’ll break compensation into salary bands that are supposed to match an employee’s level. So if you’re at a certain level, your pay falls somewhere within the corresponding salary band. Which means that if a man and a woman are in the same band, they’re going to be paid roughly the same.
That’s supposed to help correct gendered pay discrepancies. But it doesn’t really work, because there are all sorts of escape hatches built in. Salary bands only cover your salary. There’s lots of other ways that people get paid.
As we discussed, talent acquisition is one of them. Talent acquisition gives companies a way to pay a premium to people who have more social capital. But that’s not the only way that people are rewarded unequally. There’s also the sign-on bonus. The sign-on bonus in Silicon Valley today can easily be a hundred thousand dollars. Even for somebody coming off their first job, or maybe even right out of school, it can be upward of fifty thousand dollars. And the recruiters have a lot of leeway in setting that number. Then there’s your annual bonus, which is a percentage of your salary at most companies. Finally, there’s your stock-based compensation.
When you take an offer at a company, you’re given either stock options or grants of shares in the company. Those options or grants vest over a four-year schedule. And there’s really no restriction on how high that can go. So for a lot of people, a majority of total compensation comes from stock. Salary typically tops out at around $200,000 or $250,000 at a big company. But it wouldn’t be surprising to be given another $100,000 in stock grants. If you’re joining a company early on, that stock, by the time you’re done vesting it, could be more like a million dollars.What about ageism in the industry? Silicon Valley tends to be very young. Does that worry you as you get older?
I don’t know where all the old programmers go. They must go somewhere. It is a little worrisome. I’m in my thirties, and I feel like I have less energy. I’m an iOS developer and I haven’t learned Swift.3 Five years ago, definitely ten years ago, the day Swift was announced I would have become an expert on it. And I just don’t have that energy now.So it sounds like issues around equity and bias played a determining role in changing how you think about the industry.
Well, come to think of it, those are issues I’ve only come to understand in the past few years.
I think what really shifted my thinking about my success was observing that most of the startups that are getting crazy amounts of venture capital aren’t solving interesting problems. There is a lot of money going into squeezing more ad dollars out of users, and getting more attention and eyeballs. Yo is a good example.4 My app wasn’t much dumber than Yo. And they got millions of dollars of funding.
I also felt like people were becoming founders
