The Exchanges

Q Now, you've had an astonishing career from being a tech blogger and entrepreneur through founding Engie Gadget, and then a product person, and now you're at Betaworks. So can you give us a little walkthrough and a snapshot of your career so far?

A Uh, yeah, so I started out Uh, actually as a technology journalist with a magazine called Red Herring, which was the magazine covering, uh, the business of technology, uh, sort of revolution in the first dot-com wave in the late nineties. And, um, Red Herring's innovation is as much as it, as you could, you know, looking back, it seems very obvious right now, but they're, uh, uh, Modus operandi was, let's follow where the VC investment dollars are going in technology, and that'll tell us the future of technology. And, um, and so it was a very venture capital focused business of technology publication that I joined in the late nineties. And, uh, so I started off sort of writing about, uh, VC funded startups and emerging technologies and stuff like that. And did that for a few years until, uh, the bubble burst in 2001 and red herring imploded. They laid off half the staff. Uh, me among them, and, uh, moved to New York. I was based in San Francisco at the time, moved to New York in 2001, and, uh, had started blogging a few months earlier and, uh, was really interested in it. I wasn't sure where it was gonna go. It seemed at the time blogging was a very, very, very small space. Uh, there were maybe, at that point, I think there was probably less than a thousand people blogging.

AI assessment note: “I started out Uh, actually as a technology journalist with a magazine called Red Herring”

Q Now, I'd love to delve into that a bit more. So could you explain a little more about your focus on the West Coast when Betaworks is based in New York?

A Yeah, I mean, New York, New York has been the home for Betaworks since its inception, and I think historically they've been very focused on New York Both in terms of, uh, the companies they've invested in, but also because they have the studio side of the business where they build and incubate businesses, uh, That's always been, if you wanted to do that, you, you do that in their space, right? You're in residence there in New York. Now, Betaworks has done about 25, maybe 30% of its investments historically have been on the West Coast with, with the majority of those being pretty much in San Francisco, a handful in Silicon Valley. And so I think, uh, as Betaworks wanted to ramp up its seed investing, um, It made sense to have somebody who understood the Betaworks DNA on the West Coast, uh, who could help. I mean, I think there's no substitute for having boots on the ground with this sort of thing. There's so many companies to meet with, so many people to work with, and I think also for a lot of, uh, startups now, they have a lot of options when it comes to deciding who they're going to take money from, and I think having somebody that they can sit down with and, and get, and help them out when they need it actually here in the Bay Area makes a difference, but I think also Taking money from a fund that has such a strong presence in New York, they kind of get the best of both worl…

AI assessment note: “It made sense to have somebody who understood the Betaworks DNA on the West Coast”

Q Now, you've had an astonishing career from being a tech blogger and entrepreneur through founding Engie Gadget, and then a product person, and now you're at Betaworks. So can you give us a little walkthrough and a snapshot of your career so far?

A Uh, yeah, so I started out Uh, actually as a technology journalist with a magazine called Red Herring, which was the magazine covering, uh, the business of technology, uh, sort of revolution in the first dot-com wave in the late nineties. And, um, Red Herring's innovation is as much as it, as you could, you know, looking back, it seems very obvious right now, but they're, uh, uh, Modus operandi was, let's follow where the VC investment dollars are going in technology, and that'll tell us the future of technology. And, um, and so it was a very venture capital focused business of technology publication that I joined in the late nineties. And, uh, so I started off sort of writing about, uh, VC funded startups and emerging technologies and stuff like that. And did that for a few years until, uh, the bubble burst in 2001 and red herring imploded. They laid off half the staff. Uh, me among them, and, uh, moved to New York. I was based in San Francisco at the time, moved to New York in 2001, and, uh, had started blogging a few months earlier and, uh, was really interested in it. I wasn't sure where it was gonna go. It seemed at the time blogging was a very, very, very small space. Uh, there were maybe, at that point, I think there was probably less than a thousand people blogging.

AI assessment note: “I started out Uh, actually as a technology journalist with a magazine called Red Herring”

Q Now, I'd love to delve into that a bit more. So could you explain a little more about your focus on the West Coast when Betaworks is based in New York?

A Yeah, I mean, New York, New York has been the home for Betaworks since its inception, and I think historically they've been very focused on New York Both in terms of, uh, the companies they've invested in, but also because they have the studio side of the business where they build and incubate businesses, uh, That's always been, if you wanted to do that, you, you do that in their space, right? You're in residence there in New York. Now, Betaworks has done about 25, maybe 30% of its investments historically have been on the West Coast with, with the majority of those being pretty much in San Francisco, a handful in Silicon Valley. And so I think, uh, as Betaworks wanted to ramp up its seed investing, um, It made sense to have somebody who understood the Betaworks DNA on the West Coast, uh, who could help. I mean, I think there's no substitute for having boots on the ground with this sort of thing. There's so many companies to meet with, so many people to work with, and I think also for a lot of, uh, startups now, they have a lot of options when it comes to deciding who they're going to take money from, and I think having somebody that they can sit down with and, and get, and help them out when they need it actually here in the Bay Area makes a difference, but I think also Taking money from a fund that has such a strong presence in New York, they kind of get the best of both worl…

AI assessment note: “there's no substitute for having boots on the ground with this sort of thing”

Q And say that someone emails you now, and it looks like a good opportunity. What do you deep dive on? What KPIs do you always look at first? What are the metrics which really get your attention?

A So not metrics driven at this stage for me. Um, I think that what I care a lot about is I look at the product. And I, and I think that's also maybe my bias having, again, been a blogger and then a product person and an entrepreneur and product person. So I have a, I really like to dig in on a product and try to understand how it works. What is appealing about it? Does it have, how does it, how does something like this scale up and hit a large number of users or, or if it's not necessarily a large number of users, how does it become something that can drive a lot of revenue to, Someday. And, and I think that, that I have a good understanding of, of maybe the mechanics of those things now. And, and I, and I really love to, to kind of grapple with that and just frankly to sit down and talk with founders and, and kind of push them and press them on, on these, these things and say, well, you know, how does this grow and how do you acquire users and, and what about this and how does this sit within the ecosystem and what about this platform risk and, and those sorts of things. So that's the stuff that I care a lot about is, um, The product first. Is this something that is going, has a chance to find product market fit? And then if it finds product market fit, can it scale up into a large business? Uh, and you kind of need those two things. Then I also really care a lot about the foun…

AI assessment note: “So not metrics driven at this stage for me. I look at the product.”

Q And do you at BetaWorks now, being obviously based in the West Coast, do you, uh, portray yourselves to be very different to the other VCs you're competing against?

A Well, I think because of the studio side of the business, we are different. Uh, and so, not that there aren't other, uh, you know, incubators and accelerators and things like that, but we're not that. I mean, if you take, just, if you take an investment from us, you don't, Go and sit, go through an incubation program or an accelerator program. Uh, though there are circumstances where we've made an investment and brought a company sort of in-house for a few months to work, to kind of, to work on something. But I think one of the great things about Betaworks is you can tap into a whole network of people that have a tremendous amount of operational expertise. Uh, people that know and have a ton of experience building and scaling Businesses that know a lot about customer acquisition, that know a lot about monetization, and that frankly have a really kind of hacker mentality to how products get built and really understand how much it is, how experimental the process is, how important, uh, the trial and error, how much trial and error goes into finding product market fit and, and really have been, I mean, I think Betaworks has been remarkably successful in, uh, Uh, producing, uh, you know, hit products over the years, which I think is, is having tried to do it at AOL, I, I, I know it's no, no simple matter. Um, you have to really give them, them a lot of, uh, credit for, for the trac…

AI assessment note: “because of the studio side of the business, we are different.”

Q And do you at BetaWorks now, being obviously based in the West Coast, do you, uh, portray yourselves to be very different to the other VCs you're competing against?

A Well, I think because of the studio side of the business, we are different. Uh, and so, not that there aren't other, uh, you know, incubators and accelerators and things like that, but we're not that. I mean, if you take, just, if you take an investment from us, you don't, Go and sit, go through an incubation program or an accelerator program. Uh, though there are circumstances where we've made an investment and brought a company sort of in-house for a few months to work, to kind of, to work on something. But I think one of the great things about Betaworks is you can tap into a whole network of people that have a tremendous amount of operational expertise. Uh, people that know and have a ton of experience building and scaling Businesses that know a lot about customer acquisition, that know a lot about monetization, and that frankly have a really kind of hacker mentality to how products get built and really understand how much it is, how experimental the process is, how important, uh, the trial and error, how much trial and error goes into finding product market fit and, and really have been, I mean, I think Betaworks has been remarkably successful in, uh, Uh, producing, uh, you know, hit products over the years, which I think is, is having tried to do it at AOL, I, I, I know it's no, no simple matter. Um, you have to really give them, them a lot of, uh, credit for, for the trac…

AI assessment note: “Well, I think because of the studio side of the business, we are different.”

Q And then you've seen also now the West and the East Coast. So how do you compare the two technology environments and ecosystems?

A Well, I think the biggest difference is just more of size than anything else. It's just, it's so big here in the West Coast compared to New York. And New York is very strong. And I, I, I feel like I grew up in that community and, uh, and, and, uh, was in some ways it was very bittersweet leaving New York for me. Uh, just having been there for so long and having, uh, moved there really at the beginning, in some ways, basically at the beginning of my career, even though I was here for a few years before that. So I, I think that, That there are some differences in the kinds of companies that get built, which I think is kind of natural, if that may, just given, uh, the interest that people have in, in stuff in New York, I think tends to be more, maybe design focused and somewhat more commerce focused, um, though not exclusively. I think people are building more, say, on-demand startups and things like that here, um, So there obviously are differences, but, but for the most part, it's more about just the, the, the, there are so many more people working on so many different things here versus New York.

AI assessment note: “I think the biggest difference is just more of size than anything else.”

Q And say that someone emails you now, and it looks like a good opportunity. What do you deep dive on? What KPIs do you always look at first? What are the metrics which really get your attention?

A So not metrics driven at this stage for me. Um, I think that what I care a lot about is I look at the product. And I, and I think that's also maybe my bias having, again, been a blogger and then a product person and an entrepreneur and product person. So I have a, I really like to dig in on a product and try to understand how it works. What is appealing about it? Does it have, how does it, how does something like this scale up and hit a large number of users or, or if it's not necessarily a large number of users, how does it become something that can drive a lot of revenue to, Someday. And, and I think that, that I have a good understanding of, of maybe the mechanics of those things now. And, and I, and I really love to, to kind of grapple with that and just frankly to sit down and talk with founders and, and kind of push them and press them on, on these, these things and say, well, you know, how does this grow and how do you acquire users and, and what about this and how does this sit within the ecosystem and what about this platform risk and, and those sorts of things. So that's the stuff that I care a lot about is, um, The product first. Is this something that is going, has a chance to find product market fit? And then if it finds product market fit, can it scale up into a large business? Uh, and you kind of need those two things. Then I also really care a lot about the foun…

AI assessment note: “So not metrics driven at this stage for me.”

Q And then deal sourcing, what tools do you use?

A Well, so this is the part where I'm still getting up to speed. Um, I mean, we have a lot of inbound with Betaworks, uh, which is great, and so we haven't necessarily had a, a challenge finding deal flow, um, I think for me, uh, getting referred deals from other investors that I know has been really important, and the first deal that I did for Betaworks, which I can't announce yet, but, uh, closes on Wednesday, uh, that, uh, was referred to me by an investor who I've been friends with for a really long time, so that was, you know, those sorts of relationships, again, are critical. I actually do, uh, look at AngelList, uh, which I know, again, is a tool that probably everyone you, you would interview would look at, but I, I think that What I like about it is that it does democratize the process for a lot of people and gives you a chance to, if you're starting out and again, outside these existing networks, you can create a profile on there just like anybody else. And so I do really try to look at the new companies that are joining AngelList. Absolutely.

AI assessment note: “I actually do, uh, look at AngelList”

Q And then deal sourcing, what tools do you use?

A Well, so this is the part where I'm still getting up to speed. Um, I mean, we have a lot of inbound with Betaworks, uh, which is great, and so we haven't necessarily had a, a challenge finding deal flow, um, I think for me, uh, getting referred deals from other investors that I know has been really important, and the first deal that I did for Betaworks, which I can't announce yet, but, uh, closes on Wednesday, uh, that, uh, was referred to me by an investor who I've been friends with for a really long time, so that was, you know, those sorts of relationships, again, are critical. I actually do, uh, look at AngelList, uh, which I know, again, is a tool that probably everyone you, you would interview would look at, but I, I think that What I like about it is that it does democratize the process for a lot of people and gives you a chance to, if you're starting out and again, outside these existing networks, you can create a profile on there just like anybody else. And so I do really try to look at the new companies that are joining AngelList. Absolutely.

AI assessment note: “I actually do, uh, look at AngelList, uh, which I know, again, is a tool”

Q And then you've seen also now the West and the East Coast. So how do you compare the two technology environments and ecosystems?

A Well, I think the biggest difference is just more of size than anything else. It's just, it's so big here in the West Coast compared to New York. And New York is very strong. And I, I, I feel like I grew up in that community and, uh, and, and, uh, was in some ways it was very bittersweet leaving New York for me. Uh, just having been there for so long and having, uh, moved there really at the beginning, in some ways, basically at the beginning of my career, even though I was here for a few years before that. So I, I think that, That there are some differences in the kinds of companies that get built, which I think is kind of natural, if that may, just given, uh, the interest that people have in, in stuff in New York, I think tends to be more, maybe design focused and somewhat more commerce focused, um, though not exclusively. I think people are building more, say, on-demand startups and things like that here, um, So there obviously are differences, but, but for the most part, it's more about just the, the, the, there are so many more people working on so many different things here versus New York.

AI assessment note: “biggest difference is just more of size than anything else”

Q And having so many financing options, does that mean the valuations are getting higher and higher, making it more difficult for you as a seed fund?

A I think that they've actually started to rationalize a little bit more. Um, it's, it's one of these things where, uh, it depends on what stage you're at in the business. And I think that, that, uh, if you have a really hot deal, uh, there's sort of a, can be a pile on effect and the valuation can go, can go quite high. I think that also you have a lot of great platforms that startups can use, uh, Um, if they get access to them, like Y Combinator, where they can, uh, get on a literally and figuratively a very large stage and present, uh, what they're doing to the, to the, uh, the venture capital community. And so I think those make a big difference. And I think one of the things that I think is actually great about what's going on now is that, uh, if you, it's, it's probably, it's, it's easier to get access to these networks that you need to get access to, to be able to raise capital, uh, Uh, and that's, it's venture capital is very relationship driven game. Uh, a lot of, a lot of VCs, they like referrals and they like to have deals come to them through somebody they trust rather than it being sort of a cold email. I'm actually pretty open to the cold emails for what it's worth. Uh, I, I take a look at everything and, um, but I, but I, but I think that if you are outside of that world, outside of that network, it can seem very opaque. How do you Break, you know, break into it an…

AI assessment note: “I think that they've actually started to rationalize a little bit more.”

Q And having so many financing options, does that mean the valuations are getting higher and higher, making it more difficult for you as a seed fund?

A I think that they've actually started to rationalize a little bit more. Um, it's, it's one of these things where, uh, it depends on what stage you're at in the business. And I think that, that, uh, if you have a really hot deal, uh, there's sort of a, can be a pile on effect and the valuation can go, can go quite high. I think that also you have a lot of great platforms that startups can use, uh, Um, if they get access to them, like Y Combinator, where they can, uh, get on a literally and figuratively a very large stage and present, uh, what they're doing to the, to the, uh, the venture capital community. And so I think those make a big difference. And I think one of the things that I think is actually great about what's going on now is that, uh, if you, it's, it's probably, it's, it's easier to get access to these networks that you need to get access to, to be able to raise capital, uh, Uh, and that's, it's venture capital is very relationship driven game. Uh, a lot of, a lot of VCs, they like referrals and they like to have deals come to them through somebody they trust rather than it being sort of a cold email. I'm actually pretty open to the cold emails for what it's worth. Uh, I, I take a look at everything and, um, but I, but I, but I think that if you are outside of that world, outside of that network, it can seem very opaque. How do you Break, you know, break into it an…

AI assessment note: “I think that they've actually started to rationalize a little bit more.”