I hate being called a futurist. I think it's more important to understand the present, because then you can try and influence the future rather than just predict it.
Esther, it's a real pleasure to meet you and thank you for letting us honor you. We're super excited to induct you into our New York City Tech Hall of Fame. You've been an inspiration as a New Yorker and entrepreneur. Your name, your presence here has been felt for a long time. I think you consider yourself a New Yorker, having lived here for most of your adult life. You've been part of the New York City Tech community since its inception, when it got officially on the map. You've been part of the New York Angels since 2000 and New York Tech Meetup, absolutely, as a first investor in Meetup and first investor in EZRA. When you think about that journey of where New York Tech started, tell us what that was like back then.
Oh, it was kind of a small shoot in a very fancy flower garden or something like that. It was not the major industry. Whereas out in Silicon Valley, you go into any coffee shop and people are talking about options and 'oh my gosh, he's worth 400 million,' and here you get on the subway and people are reading real books and they're ballerinas and accountants. So it was very much a subculture for much longer here. I like the diversity here. I never moved to Silicon Valley. People often thought I lived there because I wrote about it so much, but I felt like this is where I live. I go to Silicon Valley to go to conferences and to work, but this place is much more in touch with the real world. So I think the tech that grows here is also more in touch with the real world.
I think right after college you moved to New York and started as a journalist and media.
I started out when I was 8 years old. I wrote the Dyson Gazette on carbon paper, which was like family happenings. I went to Harvard, but I spent most of my time writing for the Harvard Crimson, the newspaper. In the end, I joined Forbes Magazine as a fact checker, and if I could come up with a good enough story, then I could go be a reporter. I started writing about tech companies. After 3 years, I thought, 'I want to do something where I'm not just telling stories. I want to help people make real financial decisions.' I joined this fund, New Court Securities, that had already invested $100 million in this startup, and it was now doing a down round at $15 million, losing money, had not yet shipped its first package. Its name was Federal Express. Wow. And it turned out pretty well.
Can I ask you why there was a natural inclination to learn more about tech after coming from FedEx?
When I was applying to Forbes, my alternative was Variety, but more people wanted to write about movies than about business, so I got the job at Forbes. But by then, tech was getting really interesting, and it was the natural thing to do. So here you're in Oppenheimer, you basically carved out a job for yourself in software, and then finally I joined this guy who had a newsletter at a conference about the emerging personal computer world. After about half a year, it became clear that he had a conflict of interest because he was chairman of both Lotus and Compaq, which were the hot companies of the day. So I bought the newsletter from him, and then for 25 years ran the conference and the newsletter. I'd like to call myself a court jester. You're at court but you have no official standing, and everybody talks to you and tells you the truth, and you speak truth to power, but you also know how to keep secrets. It's really being present at the creation. It was an amazing 25 years. What I really liked was discovering new stuff, not so much news but analysis: what is going on, what's really happening. I hate being called a futurist because I think it's more important to understand the present, because then you can try and influence the future rather than just predict it.
It seemed like more of a path of instead of selling stock as an analyst, you're trying to seek the truth. I mean, that's the whole point of being honest, the truth, explain the truth, what is really happening.
Somebody once asked me, 'What's the most interesting technology right now?' and I think it's counterfactuals. Understanding what is, what could be, what won't be, what might have been.
Interesting. So you take over this newsletter, you rebrand it Release 1.0, right? From Rosen Electronics Letter to R1L, and it's credited to Ben Rosen who founded it. Amazing. But then you take it another step further, and it was read by some of these amazing technology leaders at the time, whether it be Steve Jobs or Bill Gates.
Steve Jobs once got really mad at me because I wrote this somewhat half-hearted review of the Lisa, and he blamed me for trying to pretend I was Ben Rosen and said nasty things.
Was that the first time you ever talked to him?
