The Exchanges

Q And the first and most important, I think, is how did you celebrate the acquisition? Was it, was it a time of great excitement? Obviously it was your first startup. Were you extremely excited or was it actually quite saddening? Was it, uh, selling off of a part of you?

A Uh, I think it was a little bit of both, but I think it was definitely a lot more excitement, um, especially sort of with, with, with the team. Everybody was really excited about, uh, like, like Salesforce as a company, and when we started, we sort of looked at, you know, companies that we admire, companies that we'd like to partner with, potentially get investments from, or potentially be acquired by, and Salesforce is definitely at the, the top of the list, and so, Um, the, the whole acquisition happened pretty quickly. We're, um, you know, they were pretty motivated, and it was pretty strategic to a new, um, division that Salesforce was launching, which, um, which is now called work.com, but prior to that was just sort of the generic kind of HR cloud that, uh, you know, Mark Benioff was super excited about back in, um, And, uh, we, we all went out to a very nice dinner, uh, you know, the entire team and, um, just sort of talked about the roller coaster and our good times and just talked about how exciting it was to be part of Salesforce. So, uh, but part of me again was, was sad because, you know, you always feel like you can build something, something bigger. And so there's always that, that aspect of it.

AI assessment note: “we all went out to a very nice dinner, uh, you know, the entire team”

Q And what was it like working in such a huge company such as Salesforce? Did your role change a lot from the startup system that you had going at Choice Pass?

A Um, it's definitely, um, adjustment in the, in the beginning, because you're moving from, you know, there were, there were 10 of us that we see every day, and, you know, the tech and product team, there was five of us, and so, from that to, you know, a massive organization where no one really, you didn't know, there's no way you can know everybody, it's quite a difference, and, you know, frankly, Um, Salesforce was the largest company I've worked for by several orders of magnitude, so, you know, having to kind of navigate that could be scary, but, um, because we were kind of our own business unit with, uh, with the HR cloud and with work.com, it felt very much, at least in the early days, like a startup within a much larger company, and so that was actually really exciting. We, you know, had our own, um, you know, we were essentially our own division, and so, Went from that, and then eventually I transitioned into Sales Cloud, which is the, you know, large multi-billion dollar entity, and I think if that were to happen from the beginning, I probably, you know, I don't think I would have enjoyed myself as much, so it was actually a good transition.

AI assessment note: “it felt very much, at least in the early days, like a startup”

Q Absolutely. And, um, moving then onto your investment strategy, um, When investing in a startup, are there aspects which really put you off, or, or really make you excited, uh, either one? Um, and, and why does that happen? What, so what really gets you going, and what doesn't? What is a red flag?

A Yeah, when I, when I, when I evaluate startups, um, you know, I'm really looking at kind of three major areas. The, the first is the team, and who's the co-founding team, or who, what's the background of the sole founder, and how do they interact and complement, complement each other, and how committed are they to, to, uh, you know, to this startup. Um, and, you know, there's, there's no replacing, um, in-person meetings here. I mean, you really have to Meet the person. Sometimes we, we meet entrepreneurs, uh, you know, maybe a dozen times, you know, to, to, to talk about everything from strategy, go to market, product, vision, hiring, before we make an investment. And I think the people, people element really can't be, um, you know, can't be underestimated. And then the second.

AI assessment note: “when I evaluate startups, um, you know, I'm really looking at kind of three major areas.”

Q And the first and most important, I think, is how did you celebrate the acquisition? Was it, was it a time of great excitement? Obviously it was your first startup. Were you extremely excited or was it actually quite saddening? Was it, uh, selling off of a part of you?

A Uh, I think it was a little bit of both, but I think it was definitely a lot more excitement, um, especially sort of with, with, with the team. Everybody was really excited about, uh, like, like Salesforce as a company, and when we started, we sort of looked at, you know, companies that we admire, companies that we'd like to partner with, potentially get investments from, or potentially be acquired by, and Salesforce is definitely at the, the top of the list, and so, Um, the, the whole acquisition happened pretty quickly. We're, um, you know, they were pretty motivated, and it was pretty strategic to a new, um, division that Salesforce was launching, which, um, which is now called work.com, but prior to that was just sort of the generic kind of HR cloud that, uh, you know, Mark Benioff was super excited about back in, um, And, uh, we, we all went out to a very nice dinner, uh, you know, the entire team and, um, just sort of talked about the roller coaster and our good times and just talked about how exciting it was to be part of Salesforce. So, uh, but part of me again was, was sad because, you know, you always feel like you can build something, something bigger. And so there's always that, that aspect of it.

AI assessment note: “I think it was a little bit of both, but I think it was definitely a lot more excitement”

Q And what was it like working in such a huge company such as Salesforce? Did your role change a lot from the startup system that you had going at Choice Pass?

A Um, it's definitely, um, adjustment in the, in the beginning, because you're moving from, you know, there were, there were 10 of us that we see every day, and, you know, the tech and product team, there was five of us, and so, from that to, you know, a massive organization where no one really, you didn't know, there's no way you can know everybody, it's quite a difference, and, you know, frankly, Um, Salesforce was the largest company I've worked for by several orders of magnitude, so, you know, having to kind of navigate that could be scary, but, um, because we were kind of our own business unit with, uh, with the HR cloud and with work.com, it felt very much, at least in the early days, like a startup within a much larger company, and so that was actually really exciting. We, you know, had our own, um, you know, we were essentially our own division, and so, Went from that, and then eventually I transitioned into Sales Cloud, which is the, you know, large multi-billion dollar entity, and I think if that were to happen from the beginning, I probably, you know, I don't think I would have enjoyed myself as much, so it was actually a good transition.

AI assessment note: “it felt very much, at least in the early days, like a startup”

Q Absolutely. And, um, moving then onto your investment strategy, um, When investing in a startup, are there aspects which really put you off, or, or really make you excited, uh, either one? Um, and, and why does that happen? What, so what really gets you going, and what doesn't? What is a red flag?

A Yeah, when I, when I, when I evaluate startups, um, you know, I'm really looking at kind of three major areas. The, the first is the team, and who's the co-founding team, or who, what's the background of the sole founder, and how do they interact and complement, complement each other, and how committed are they to, to, uh, you know, to this startup. Um, and, you know, there's, there's no replacing, um, in-person meetings here. I mean, you really have to Meet the person. Sometimes we, we meet entrepreneurs, uh, you know, maybe a dozen times, you know, to, to, to talk about everything from strategy, go to market, product, vision, hiring, before we make an investment. And I think the people, people element really can't be, um, you know, can't be underestimated. And then the second.

AI assessment note: “I'm really looking at kind of three major areas. The, the first is the team”

Q Okay, we'll leave that on for another day. So we've got the team. What are the other two aspects?

A Yeah, the other two elements is the market as a whole, the market that they're, that the company is looking at, and that I think is important for a few reasons. You have, um, a few different types of VCs. You have Some VCs that are generalists, where they've done a ton of different deals across different industries and different markets, and then you have VCs that are very focused. And I think that, ah, the value of being very focused on specific industries is that you really build, you know, deep knowledge in those industries. So you have VCs that focus just on, um, just on fintech, for example. Me, personally, I've been looking, ah, a ton into Mobile-enabled services, so sort of the on-demand space. I've also been actively looking at, um, drones and, uh, the drone space and, and AI, which is quickly emerging, uh, and as you, and also obviously enterprise software, given my, my, my prior experience. And so when you're, when you're kind of diving deep into specific industries, you can really provide tremendous amounts, tremendous value, right? And I'm sure other VCs say this, but Capital is a commodity. There's so many different sources of capital now that you need to really provide things that are different, and I think that having that, um, difference, uh, you know, having that industry knowledge is, is, is quite important. And then, um, the third area is, you know, metrics. …

AI assessment note: “the other two elements is the market as a whole... third area is, you know, metrics.”

Q Now, as, obviously, as founder of Choice Pass, you experienced a lot of difficulties, uh, in growing a startup. What would you say was the most difficult element that you faced in your time at Choice Pass?

A Yeah, I think that's a great question. So the, you know, our original idea for Choice Pass was a mobile membership platform for local merchants. So, um, back in 2011, 2012, your Groupons and Living Socials were the king of the world, and we wanted a way for, for, um, local merchants to be able to, to cheaply bring back those customers. And we actually raised our seed round based on that. But As we, you know, as the months went by, uh, the data was showing that it wasn't working, and so we had to pivot, um, and so my co-founder and I, you know, we locked ourselves in a room, we had an all-day, uh, several-day strategy session where we were talking about what are the problems we can solve, and then, that ultimately led us to ChoicePass, because a lot of the local merchants that we were talking about, uh, talking to, Um, really wanted more corporate business, and they really wanted more regular business rather than the clientele that was coming from, you know, daily deal sites. And so, that ultimately led us to create the first version of Choice Pass, which is a, uh, corporate perks platform, which then evolved into focusing more on, um, employee rewards, which is actually the side of the business that, um, was most appealing for Salesforce and what we focused on at Salesforce.

AI assessment note: “the data was showing that it wasn't working, and so we had to pivot”

Q Thank you very much. I'm glad we've entertained you. Um, now, I'm really curious about how you yourself Got into the technology industry, and then later made your transition into your current venture capital status. Could you tell us a little about that?

A Yeah, absolutely. So, I actually started my career in finance, so after I graduated from college, I did a two-year, um, private equity analyst program similar to the banks, and was promoted straight through, and thought I would sort of stay in that area, um, you know, for the, for most of my career, um, even spent a few years in Asia, um, and it wasn't until, uh, I got to Harvard Business School that I started, um, exploring technology, so, um, You know, when you get an MBA, it's a great time to sort of reassess what, what you'd like to do, and, uh, you know, I took a course called Launching Tech Ventures, which was really, you know, the first class that I've taken that's technology-oriented, and as part of that, did a project with, um, project, uh, a product management director at Google, and then from there, decided to kind of focus much more into technology, and ultimately, that led me to start a company.

AI assessment note: “decided to kind of focus much more into technology, and ultimately, that led me”

Q And where do you see the future of incentivizing people, and how important do you feel it is?

A Well, I mean, I've always had this thesis that your people are your most valuable resource, and there's no other place that, where that's more true than in the Valley, where, uh, you know, talent really has a number of different options that they can go to, and so I really believe that, um, having the right culture and having the right, uh, incentives and rewards is critical for the success of a company, and I felt that there was a lot of unfinished work Um, you know, with Choice Pass and with Work.com, and then now having moved into venture, and so I've kept in close touch with the Any Perk team, and I think that they've done a really good job of, um, executing, of delighting their customers, and, um, and I think they're well positioned to, to really own this, this market.

AI assessment note: “having the right incentives and rewards is critical for the success of a company”

Q Awesome, awesome. Now, with the recent deregulation of marijuana consumption in the US, we've seen a lot of marijuana startups. I know Founders Fund recently made a substantial investment in Leafly, um, and you yourself have invested in one being Ease, the Uber for medical marijuana. Are you concerned about the prospect of possible increasing regulation, and where do you see the future of integrating tech with marijuana?

A Yeah, no, I think, I think that's a great question. On, on the, on the regulation side, I, I think that, you know, VCs generally have to take, ah, a bit of regulation risk, right? You, you either make a call that regulation is going in, in the direction that's favorable towards, towards, um, you know, the potential investments you're looking at, or they're not. And it's not, um, specific to marijuana. If you look at, Um, anywhere from, if you look at things like, um, like, uh, the, the drone space, for example, and the FAA just recently coming up with regulations, which largely have seen to be positive towards the development of commercial drone space, or if you look at education as an, as another example, or, um, you know, a number of other industries, even like Uber, when they first started, it was technically illegal, and a ton of, Um, municipalities, so I think that you have to make a call on where you see regulation going, and, you know, specific to your question, I think that, ah, there is increased, um, acceptance that medical marijuana is something that should be legal, not just, ah, you know, in certain states, but potentially federally, and I think that, you know, we, we as a DCM, as a fund, really saw that, ah, regulations were shifting Uh, in a way that we hadn't seen in the last, uh, couple of decades, and so, uh, this led to a real market opportunity for, for inno…

AI assessment note: “we as a DCM, as a fund, really saw that, ah, regulations were shifting”

Q Now, as, obviously, as founder of Choice Pass, you experienced a lot of difficulties, uh, in growing a startup. What would you say was the most difficult element that you faced in your time at Choice Pass?

A Yeah, I think that's a great question. So the, you know, our original idea for Choice Pass was a mobile membership platform for local merchants. So, um, back in 2011, 2012, your Groupons and Living Socials were the king of the world, and we wanted a way for, for, um, local merchants to be able to, to cheaply bring back those customers. And we actually raised our seed round based on that. But As we, you know, as the months went by, uh, the data was showing that it wasn't working, and so we had to pivot, um, and so my co-founder and I, you know, we locked ourselves in a room, we had an all-day, uh, several-day strategy session where we were talking about what are the problems we can solve, and then, that ultimately led us to ChoicePass, because a lot of the local merchants that we were talking about, uh, talking to, Um, really wanted more corporate business, and they really wanted more regular business rather than the clientele that was coming from, you know, daily deal sites. And so, that ultimately led us to create the first version of Choice Pass, which is a, uh, corporate perks platform, which then evolved into focusing more on, um, employee rewards, which is actually the side of the business that, um, was most appealing for Salesforce and what we focused on at Salesforce.

AI assessment note: “the data was showing that it wasn't working, and so we had to pivot”

Q And where do you see the future of incentivizing people, and how important do you feel it is?

A Well, I mean, I've always had this thesis that your people are your most valuable resource, and there's no other place that, where that's more true than in the Valley, where, uh, you know, talent really has a number of different options that they can go to, and so I really believe that, um, having the right culture and having the right, uh, incentives and rewards is critical for the success of a company, and I felt that there was a lot of unfinished work Um, you know, with Choice Pass and with Work.com, and then now having moved into venture, and so I've kept in close touch with the Any Perk team, and I think that they've done a really good job of, um, executing, of delighting their customers, and, um, and I think they're well positioned to, to really own this, this market.

AI assessment note: “having the right, uh, incentives and rewards is critical for the success of a company”