The Exchanges

Q I'd love to kick off though now by hearing how you made your way into the wonderful world of venture. What was your start?

A Oh, sure. Um, that's the question we all get all the time, which is a good one because there's no clear answer. There's a There's no path. There's no formula. There's no, if you do this, you'll be able to get into venture. I've got it. It's a healthy dose of luck and timing and hard work and all of those things. But, um, for me, I took a bit of an unconventional path. If you start at college and move on, I actually was pre-med undergrad and went to medical school immediately after college. I dropped out, um, before Before the end of the first semester, I figured if I wasn't going to do the med school thing, I didn't need to take finals. So quit right before that. And, um, it took a few months to figure out what on earth I was going to do. From there, I ended up starting off at Summit Partners, which is the growth capital private equity firm in Boston. So that was an immersive experience. I basically didn't know how to use Excel and was suddenly, uh, at a private equity firm. So that was, to say the least, an interesting few years. Learned a ton And what I got there was exposure to a broad range of industries, broad range of business models, learned a little bit about a lot of things. And, you know, really, it was a, it was a great learning experience. From there, I wanted to see the other side. I liked the work I was doing, but wanted to understand it more in context and less i…

AI assessment note: “I ended up starting off at Summit Partners, which is the growth capital private equity”

Q And talking of wearables and blah blah blah, what is your take on investing in hardware? It's a space that many VCs maybe shy away from, but your investment in bubble bar suggests that's not you. So what's your thesis on this?

A Sure. So, so bubble bar is a little bit different, right? So they're, you know, a fashion jewelry brand and wanting to be kind of the go-to place for that, uh, for that category, which, you know, doesn't really exist. So they've done a nice job being able to kind of build that awareness. Build a brand around it. And they did, they'll do, you'll see them do, um, some of these collaborations in adjacent spaces. And that's what this was with, with Jawbone. So kind of this collaboration, although Jawbone was still manufacturing that hardware. So, you know, I don't really classify that as hardware. We've looked at, uh, a number of Hardware companies. There's a lot of really interesting stuff. Internet of things, obviously. The challenge that we've had is, you know, where we're focused today, usually, uh, what we expect is that the product is out in market. Um, there is some early data. We can, you know, we can at least look at that early data and start to understand if you found a core market who really loves your product and start to wrap our heads around where that could go. The issue that I've seen with a lot of hardware companies is that When they come to me or come to us for a series A, they haven't really shipped product yet, which just makes it difficult for us to determine, um, what the risks are in the manufacturing process. I mean, you see a lot of folks who have very succ…

AI assessment note: “that's not something that we've yet gotten comfortable with”

Q And before we dive into a quick fire round, talking of brands there, as a big investor in the consumer space, does the diminishing brand loyalty within the millennial sector concern you? I mean, is that something that you yourself have noticed?

A Sure. So, um, I think that a lot of that research that, that, you know, and a lot of those thought pieces around that are about brands or heritage brands, brands that are, you know, have been around a while that millennials don't necessarily identify with. I think what that really is, is an opportunity for the next generation, um, of people who are building brands today, most of which are being built online first and then moving offline. Um, but you know, that's an opportunity to have a brand that people actually, and this generation can identify with, um, you know, kind of shared values. So rather than it being threatening, I think it's actually an opportunity to be, you know, kind of the brands that this generation grows up with.

AI assessment note: “rather than it being threatening, I think it's actually an opportunity”

Q And talking of wearables and blah blah blah, what is your take on investing in hardware? It's a space that many VCs maybe shy away from, but your investment in bubble bar suggests that's not you. So what's your thesis on this?

A Sure. So, so bubble bar is a little bit different, right? So they're, you know, a fashion jewelry brand and wanting to be kind of the go-to place for that, uh, for that category, which, you know, doesn't really exist. So they've done a nice job being able to kind of build that awareness. Build a brand around it. And they did, they'll do, you'll see them do, um, some of these collaborations in adjacent spaces. And that's what this was with, with Jawbone. So kind of this collaboration, although Jawbone was still manufacturing that hardware. So, you know, I don't really classify that as hardware. We've looked at, uh, a number of Hardware companies. There's a lot of really interesting stuff. Internet of things, obviously. The challenge that we've had is, you know, where we're focused today, usually, uh, what we expect is that the product is out in market. Um, there is some early data. We can, you know, we can at least look at that early data and start to understand if you found a core market who really loves your product and start to wrap our heads around where that could go. The issue that I've seen with a lot of hardware companies is that When they come to me or come to us for a series A, they haven't really shipped product yet, which just makes it difficult for us to determine, um, what the risks are in the manufacturing process. I mean, you see a lot of folks who have very succ…

AI assessment note: “that's not something that we've yet gotten comfortable with.”

Q And we spoke there about the effectiveness of emails in marketing new products. So how effective do you think we'll see push notifications in the emergence of the new mobile first world?

A It's a fine line. Um, they need to, push notifications generally need to be smarter. Um, you know, the push overall in this ecosystem is, and it's been talked about for years, but the hope is that eventually we'll, you know, and hopefully in the near term we'll see it, but it's personalization and customization. So you're seeing customization even on the product side, but on the personalization front, it's about getting the right product or the right service to the right person at the right time and notifying them about that in the right way. Right. You know, having a blast push notification to all of your app users, you know, that's, that's tough unless it's going to be, you know, unless it's something like guilt that only, you know, as we'll have one sale a day or that's not even the model anymore, but you know what I mean? Like, you know, that someone, a consumer is trained to expect if they're going to get a push notification, it's going to be at noon. There are, but if you are more of a broad based service, You know, you need to be really smart about that, um, and it really needs to be relevant. It needs to be to the right set of users, and it needs to be something that you know is going to be relevant at that moment in time. So I think it can be very powerful. I think it also has to be used intelligently, and you know, it can really alienate if it's done poorly, and you k…

AI assessment note: “So I think it can be very powerful. I think it also has to be used intelligently”

Q And we spoke there about the effectiveness of emails in marketing new products. So how effective do you think we'll see push notifications in the emergence of the new mobile first world?

A It's a fine line. Um, they need to, push notifications generally need to be smarter. Um, you know, the push overall in this ecosystem is, and it's been talked about for years, but the hope is that eventually we'll, you know, and hopefully in the near term we'll see it, but it's personalization and customization. So you're seeing customization even on the product side, but on the personalization front, it's about getting the right product or the right service to the right person at the right time and notifying them about that in the right way. Right. You know, having a blast push notification to all of your app users, you know, that's, that's tough unless it's going to be, you know, unless it's something like guilt that only, you know, as we'll have one sale a day or that's not even the model anymore, but you know what I mean? Like, you know, that someone, a consumer is trained to expect if they're going to get a push notification, it's going to be at noon. There are, but if you are more of a broad based service, You know, you need to be really smart about that, um, and it really needs to be relevant. It needs to be to the right set of users, and it needs to be something that you know is going to be relevant at that moment in time. So I think it can be very powerful. I think it also has to be used intelligently, and you know, it can really alienate if it's done poorly, and you k…

AI assessment note: “So I think it can be very powerful. I think it also has to be used intelligently”

Q And obviously Chris Sacker, the legend of investing. I think he's got the most successful fund ever with Lowercase's first fund. But what were your biggest takeaways then from that first experience working with Chris?

A Oh man. Um, I mean, he was, he was very much in the flow, right? Um, in terms of, in terms of deal flow, in terms of, um, seeing the things that he wanted to see. I mean, he had access to, And that was because he had a pretty extensive network and was well known and, um, was well liked by founders. And, and that's, you know, that's how that builds. You know, he had hustled his way there and, um, you know, it's, it's great to see, you know, where he's gone from there. Uh, obviously very exciting. I mean, he, he, it was fun to, you know, kind of sit in meetings with him and, and, you know, hear how he went about it. He was always very founder centric and Wanted to, you know, hear the story from their point of view and would always kind of riff with them on where things were going, was pretty collaborative, uh, because these companies were pretty early on when he was talking to them. So it was interesting, of course, to see, to see that and see him get deep into the product and, you know, get really excited about what they were doing.

AI assessment note: “He was always very founder centric and Wanted to, you know, hear the story”

Q And obviously Chris Sacker, the legend of investing. I think he's got the most successful fund ever with Lowercase's first fund. But what were your biggest takeaways then from that first experience working with Chris?

A Oh man. Um, I mean, he was, he was very much in the flow, right? Um, in terms of, in terms of deal flow, in terms of, um, seeing the things that he wanted to see. I mean, he had access to, And that was because he had a pretty extensive network and was well known and, um, was well liked by founders. And, and that's, you know, that's how that builds. You know, he had hustled his way there and, um, you know, it's, it's great to see, you know, where he's gone from there. Uh, obviously very exciting. I mean, he, he, it was fun to, you know, kind of sit in meetings with him and, and, you know, hear how he went about it. He was always very founder centric and Wanted to, you know, hear the story from their point of view and would always kind of riff with them on where things were going, was pretty collaborative, uh, because these companies were pretty early on when he was talking to them. So it was interesting, of course, to see, to see that and see him get deep into the product and, you know, get really excited about what they were doing.

AI assessment note: “He was always very founder centric and Wanted to, you know, hear the story”

Q And I'd love to hear who you think has really embraced the mobile first approach. Are there any consumer facing companies that can really stand out as being effective in this sector?

A Well, if you, if you, if you bank it in just retail, then it's harder. Um, if you, if it's more broadly kind of just transactionally based, um, consumer businesses, then there's some obvious ones like, you know, some of the mobile first companies. Like, you know, the hotels, hotel tonight's of the world. Um, but in, in a pure kind of retail context, it's almost dependent upon when the company was founded, like almost dependent on what year they were founded as to how good their mobile experience is right now and was off the bat. Uh, you know, a lot of people have done a nice job backfilling it, but if you were founded in You know, you did not have a great mobile experience. It wasn't necessary. It wasn't necessary really until probably the middle of 2014. Maybe that's a little bit late. Maybe it was more early 20 14. Um, but so the, the companies that were founded then or right around then tend to have a better mobile experience right off the bat.

AI assessment note: “Like, you know, the hotels, hotel tonight's of the world.”

Q And I'd love to hear who you think has really embraced the mobile first approach. Are there any consumer facing companies that can really stand out as being effective in this sector?

A Well, if you, if you, if you bank it in just retail, then it's harder. Um, if you, if it's more broadly kind of just transactionally based, um, consumer businesses, then there's some obvious ones like, you know, some of the mobile first companies. Like, you know, the hotels, hotel tonight's of the world. Um, but in, in a pure kind of retail context, it's almost dependent upon when the company was founded, like almost dependent on what year they were founded as to how good their mobile experience is right now and was off the bat. Uh, you know, a lot of people have done a nice job backfilling it, but if you were founded in You know, you did not have a great mobile experience. It wasn't necessary. It wasn't necessary really until probably the middle of 2014. Maybe that's a little bit late. Maybe it was more early 20 14. Um, but so the, the companies that were founded then or right around then tend to have a better mobile experience right off the bat.

AI assessment note: “in a pure kind of retail context, it's almost dependent upon when the company was founded”