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Ben Sun

Oct 8, 2026

25:48
I'm curious how you have shifted and evolved your strategy over time as you guys have taken on more capital and obviously made a lot of great investments.
Ben Sun
Ben SunGUEST
25:57
Yeah.
Ben Sun
Ben SunGUEST
25:57
So, you know, we started investing our first fund.
Ben Sun
Ben SunGUEST
25:58
It was a $60 million seed fund focused on New York and starting in 2015.
Ben Sun
Ben SunGUEST
26:03
Um, [lip smack] and to rewind the clock at that point, you know, 2015, the biggest exit in New York City tech history was Tumblr.
Ben Sun
Ben SunGUEST
26:11
It got acquired by Yahoo for a billion dollars, right? So we had one unicorn exit in its history.
Ben Sun
Ben SunGUEST
26:16
So, you know, people would ask, like, "Why would you want to focus on a market that's produced barely any big outcomes?" And, uh, Brad and I, our response was, "We think it's all about the change." Um, and the thesis was New York was always this great magnet for talent.

15 MINS LATER

41:15
Just wanna hear more about the origin story and what all you're doing there.
42:04
Is that more... disconcerting in the moment when you do a seed round based on maybe an alumni of a bigger tech company or someone that's going it alone in this environment?
Ben Sun
Ben SunGUEST
42:16
Yeah, people look at historical data and they say, well, the round size has gotten bigger, so it hasn't become irrational.
Ben Sun
Ben SunGUEST
42:24
The reason why it has become bigger is because it's become more rational.
Ben Sun
Ben SunGUEST
42:28
Think about the founding talent alone.
Ben Sun
Ben SunGUEST
42:31
I started my career as a founder 30 years ago.
Ben Sun
Ben SunGUEST
42:36
What we knew about the internet and how to scale a technology company back then, I mean, it's night and day to where you see the market and the type of talent you have now.
Ben Sun
Ben SunGUEST
42:47
A lot of the talent are coming from best in class tech companies that have gone from zero to a billion dollar type outcomes, if not more.
43:23
What are the corners of the technology industry or opportunities where the technology just doesn't exist yet?

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