The Exchanges

Q And having seen how the VC world operates now, do you have a kind of set of VCs who you really admire and look up to?

A You know, because this, the whole topic of this discussion is around venture capitalists as well, is, uh, I think It's been so noisy, um, in the past five years since I've started doing this. It's been five years now, um, that it's almost so hard to know if a VC is truly someone you want to look up to or respect until you actually know them. So it's, you know, you read a lot, you know, there's a lot out there. There's people who love blogging and people who have a great persona, but until you truly know them, um, You know, it's really, really hard. So the folks that I truly know, because I've literally been married to them for almost five years now, are my VCs. And, uh, the, the, the, my main VCs are True Ventures, um, Hummer Winblad, Relay Ventures.

AI assessment note: “the folks that I truly know... my main VCs are True Ventures”

Q And who's a thought leader to you in the industry? Who do you look to emulate as a founder?

A You know, I always like to say I don't necessarily want to follow or emulate someone because what worked for them may not work for me. What I do do, though, is I get sort of inspired and energized by some of these people and just what they've been able to accomplish. Um, and so, you know, there's the classics, like the Elons, and then the, now there's the Elizabeth Holmes of the world. Um, but one thing that, you know, really strikes me are founders that are just Really not as loud, but are there to really solve big problems. So, um, you know, one I actually just recently spent a lot of time with, I was actually at a road hockey tournament, a charity road hockey tournament with him. Over the weekend was, uh, the guy, a fellow named Mike Serbenes. He's actually one of our investors. He's the, uh, well-known for the, being the founder of Kobo, which is the e-book reader that Rakuten, uh, acquired a few years ago. Um, and he actually recently started a new company called League, which is basically a, uh, sort of a preventative health Care type of app that, you know, the whole premise of it is you have a, a league of people that help, uh, basically maintain your health levels at the best you could possibly have them at, which is folks like nutritionists, uh, you know, toxicologists, uh, physiotherapists, pretty much all those folks that you can now bring around you, uh, folks that …

AI assessment note: “a fellow named Mike Serbenes. He's actually one of our investors.”

Q And I have to ask, as a huge fan of Kevin Rose's myself, what was it like working with such an amazing founder like Kevin and like Jay when you were at Dig, and what were your biggest takeaways from that experience pre-Keep?

A Actually, I learned quite a bit with that dynamic between Kevin and Jay, right? Because, as you know, Jay was brought in, uh, Kevin was the founder, but at the time that I was there, it was kind of during this transition period Uh, because, uh, I mean, there's a lot of turmoil at the time, right? It was, it was, you know, it was, um, uh, you know, Jay was, had left, uh, you know, Kevin was back in, uh, and then as CEO, and then they were finding, uh, a new CEO with Matt Williams, uh, Who came in right when I got laid off. Um, and then there was sort of this, uh, head of product, Cable Desai, that Kevin hired. Uh, and there was a, there was a head of design, Jeffrey Kalmakoff, who was also sort of a head of product at the time, but that Jay had hired. So I'm not going to go into too many details, but basically during that period of time, I learned about sort of where, um, Where founders reclaim their territory is kind of a good way to explain, express that. Um, and where, and where rightfully so, uh, in the way that the company had kind of lost its way, um, not that Jay didn't do a great job, but there was also sort of this need for a founder to come in and reinstate their, their sort of, um, the reasons why the company was started in the first place and kind of bring things to this original vision. And so, there's just a lot of things that I saw that helped me understand how to…

AI assessment note: “helped me understand how to structure teams, think about products”

Q And having seen how the VC world operates now, do you have a kind of set of VCs who you really admire and look up to?

A You know, because this, the whole topic of this discussion is around venture capitalists as well, is, uh, I think It's been so noisy, um, in the past five years since I've started doing this. It's been five years now, um, that it's almost so hard to know if a VC is truly someone you want to look up to or respect until you actually know them. So it's, you know, you read a lot, you know, there's a lot out there. There's people who love blogging and people who have a great persona, but until you truly know them, um, You know, it's really, really hard. So the folks that I truly know, because I've literally been married to them for almost five years now, are my VCs. And, uh, the, the, the, my main VCs are True Ventures, um, Hummer Winblad, Relay Ventures.

AI assessment note: “my main VCs are True Ventures, um, Hummer Winblad, Relay Ventures.”

Q And I have to ask, as a huge fan of Kevin Rose's myself, what was it like working with such an amazing founder like Kevin and like Jay when you were at Dig, and what were your biggest takeaways from that experience pre-Keep?

A Actually, I learned quite a bit with that dynamic between Kevin and Jay, right? Because, as you know, Jay was brought in, uh, Kevin was the founder, but at the time that I was there, it was kind of during this transition period Uh, because, uh, I mean, there's a lot of turmoil at the time, right? It was, it was, you know, it was, um, uh, you know, Jay was, had left, uh, you know, Kevin was back in, uh, and then as CEO, and then they were finding, uh, a new CEO with Matt Williams, uh, Who came in right when I got laid off. Um, and then there was sort of this, uh, head of product, Cable Desai, that Kevin hired. Uh, and there was a, there was a head of design, Jeffrey Kalmakoff, who was also sort of a head of product at the time, but that Jay had hired. So I'm not going to go into too many details, but basically during that period of time, I learned about sort of where, um, Where founders reclaim their territory is kind of a good way to explain, express that. Um, and where, and where rightfully so, uh, in the way that the company had kind of lost its way, um, not that Jay didn't do a great job, but there was also sort of this need for a founder to come in and reinstate their, their sort of, um, the reasons why the company was started in the first place and kind of bring things to this original vision. And so, there's just a lot of things that I saw that helped me understand how to…

AI assessment note: “I learned about sort of where, um, Where founders reclaim their territory”

Q And who's a thought leader to you in the industry? Who do you look to emulate as a founder?

A You know, I always like to say I don't necessarily want to follow or emulate someone because what worked for them may not work for me. What I do do, though, is I get sort of inspired and energized by some of these people and just what they've been able to accomplish. Um, and so, you know, there's the classics, like the Elons, and then the, now there's the Elizabeth Holmes of the world. Um, but one thing that, you know, really strikes me are founders that are just Really not as loud, but are there to really solve big problems. So, um, you know, one I actually just recently spent a lot of time with, I was actually at a road hockey tournament, a charity road hockey tournament with him. Over the weekend was, uh, the guy, a fellow named Mike Serbenes. He's actually one of our investors. He's the, uh, well-known for the, being the founder of Kobo, which is the e-book reader that Rakuten, uh, acquired a few years ago. Um, and he actually recently started a new company called League, which is basically a, uh, sort of a preventative health Care type of app that, you know, the whole premise of it is you have a, a league of people that help, uh, basically maintain your health levels at the best you could possibly have them at, which is folks like nutritionists, uh, you know, toxicologists, uh, physiotherapists, pretty much all those folks that you can now bring around you, uh, folks that …

AI assessment note: “one I actually just recently spent a lot of time with... Mike Serbenes.”

Q So, in terms of how have that altered from the True Ventures style seed fund, like, what was surprising to you?

A Oh, actually, yes, yes. So, I mean, then it became very industry-related, right, um, and customer-relevant, because in the beginning, it's like, kumbaya, it's kind of like, um, it's like, it's like college, right? In the first year, you kind of want to hang out with everyone, and You know, you kind of meet everyone from all different, you know, faculties and different subjects and whatever, and you become good friends, and then later on, you just spend more time in, you know, small groups with, you know, the people that are in your, in your subject, or even when you get your master's and your PhD, same thing. Um, same goes with this and that, you know, later on, everything becomes more subject matter focused. You know, our VCs are related to what we do, right? Our investors are related to what we do, and I care less about investors that are generally cool, Right? And I care more about investors that can help us generate more revenue.

AI assessment note: “then it became very industry-related, right, um, and customer-relevant”

Q So, in terms of how have that altered from the True Ventures style seed fund, like, what was surprising to you?

A Oh, actually, yes, yes. So, I mean, then it became very industry-related, right, um, and customer-relevant, because in the beginning, it's like, kumbaya, it's kind of like, um, it's like, it's like college, right? In the first year, you kind of want to hang out with everyone, and You know, you kind of meet everyone from all different, you know, faculties and different subjects and whatever, and you become good friends, and then later on, you just spend more time in, you know, small groups with, you know, the people that are in your, in your subject, or even when you get your master's and your PhD, same thing. Um, same goes with this and that, you know, later on, everything becomes more subject matter focused. You know, our VCs are related to what we do, right? Our investors are related to what we do, and I care less about investors that are generally cool, Right? And I care more about investors that can help us generate more revenue.

AI assessment note: “later on, everything becomes more subject matter focused”

Q And I'd love to hear about, kind of, with the evolution of technology and the progression of time, how are you addressing the growing competitive market, and how are you navigating Keep into the new social media channels?

A I think that There's a lot of cool tech, and there's always a need to be on top of those new technologies, and obviously connected devices is one, and we caught, we caught on to it quite early, and we ended up integrating Keep into connected device companies, like connected cars, and most recently connected breathalyzer, which is hysterical of an example, but we kind of learned about this area and started dabbling in it, and the whole point is, Making sure that you have some bandwidth as a CEO to keep your head above the water to sort of see what's going on and really understand what you could try doing and knowing that it is part of your job to go out there and think of very strategic ideas, uh, that people can then look at and then think of their own ideas and actually helping you execute. Like your job isn't to like do the whole thing and Implement the new technology, it's to jog people's thinking into kind of looking at what you're building, and then go, hmm, that's really cool, maybe we should actually build this into a full product line. So, um, that's kind of been my methodology to it, and I think we've, we've done a pretty good job at it so far.

AI assessment note: “we ended up integrating Keep into connected device companies, like connected cars”

Q And then finally, what do the next five years hold for you and for Keep?

A Uh, a lot. And, uh, maybe an IPO, uh, you know, maybe, uh, more, uh, you know, there's just a lot that could be an horizon. You know, we, we've been obviously tackling the connected device space. We released our loyalty platform a few months ago with MasterCard as our lead client, and we've got a bunch more announcements in the coming month. Um, Um, and just, there's just a lot of exciting things. I mean, especially with two major forces guiding the industry today, one being the ad blocking is now at an absolute fever pitch, and we are right at the center of being the ones that can actually help it. Uh, and then the other forces working in our favor is, You know, everyone looking for this, this ability to, to understand, uh, app data, and usage data, and, uh, and of course we have, uh, been sitting on a lot of that over the past five years, so just a lot of really good things are working in our favor right now, and I'm very excited for the next five years.

AI assessment note: “maybe an IPO”

Q Okay, so, so now with Keep, you're, you're quite, well, very famous for raising VC funding at 19. How difficult, though, this, this question's actually from Chris Redliss, um, who I actually spoke to before the interview, and he wondered, how difficult have you found it to raise growth capital beyond Series A?

A So there's two very interesting questions there. So from a, from a, from a early stage standpoint, I would say at the time I was, again, a lot of right place, right time, which, you know, a lot of preparation leads to luck and all that fun stuff. But, uh, I ended up, uh, being able to raise 300,000 in our seed round. Um, if you recall in 2010 it was kind of like the financial crisis of oh eight was just recent memory and a lot of really smart investors were starting to really think about seed investing again. And that's when true was kind of there. And they had just raised the fund and, you know, 300,000 is not exactly a massive amount of money compared to the 200 and fifteen million I think was in their fund. Um, So, you know, made a lot of sense. And then, of course, at the time, I had now some references at Digg. I at least was, you know, execution, um, oriented enough that I had projects that could show for my, my work. And, uh, and the idea was spot on in a space that was growing extremely quickly, which was, you know, mobile and mobile apps and games and, and, and then advertising.

AI assessment note: “from a early stage standpoint... able to raise 300,000 in our seed round.”

Q Okay, so, so now with Keep, you're, you're quite, well, very famous for raising VC funding at 19. How difficult, though, this, this question's actually from Chris Redliss, um, who I actually spoke to before the interview, and he wondered, how difficult have you found it to raise growth capital beyond Series A?

A So there's two very interesting questions there. So from a, from a, from a early stage standpoint, I would say at the time I was, again, a lot of right place, right time, which, you know, a lot of preparation leads to luck and all that fun stuff. But, uh, I ended up, uh, being able to raise 300,000 in our seed round. Um, if you recall in 2010 it was kind of like the financial crisis of oh eight was just recent memory and a lot of really smart investors were starting to really think about seed investing again. And that's when true was kind of there. And they had just raised the fund and, you know, 300,000 is not exactly a massive amount of money compared to the 200 and fifteen million I think was in their fund. Um, So, you know, made a lot of sense. And then, of course, at the time, I had now some references at Digg. I at least was, you know, execution, um, oriented enough that I had projects that could show for my, my work. And, uh, and the idea was spot on in a space that was growing extremely quickly, which was, you know, mobile and mobile apps and games and, and, and then advertising.

AI assessment note: “So from a, from a, from a early stage standpoint, I would say”

Q And I'd love to hear about, kind of, with the evolution of technology and the progression of time, how are you addressing the growing competitive market, and how are you navigating Keep into the new social media channels?

A I think that There's a lot of cool tech, and there's always a need to be on top of those new technologies, and obviously connected devices is one, and we caught, we caught on to it quite early, and we ended up integrating Keep into connected device companies, like connected cars, and most recently connected breathalyzer, which is hysterical of an example, but we kind of learned about this area and started dabbling in it, and the whole point is, Making sure that you have some bandwidth as a CEO to keep your head above the water to sort of see what's going on and really understand what you could try doing and knowing that it is part of your job to go out there and think of very strategic ideas, uh, that people can then look at and then think of their own ideas and actually helping you execute. Like your job isn't to like do the whole thing and Implement the new technology, it's to jog people's thinking into kind of looking at what you're building, and then go, hmm, that's really cool, maybe we should actually build this into a full product line. So, um, that's kind of been my methodology to it, and I think we've, we've done a pretty good job at it so far.

AI assessment note: “There's a lot of cool tech, and there's always a need to be on top”