The Exchanges

Q Now, I'd love to get started today by hearing a little bit about you and how you came to rock the world of venture with Foundry. What's the brief synopsis?

A Yeah, well, I started out life in the technology industry as an entrepreneur, so I moved out I went to California Bay Area in, in 1989 to go to Stanford as an undergrad, and I met five of my classmates in my freshman dorm, and as we moved on to graduation, decided it would be much more interesting to start a company and work for ourselves rather than someone else, and it was literally that sort of flimsy of motivation that ultimately led us to creating search engine Excite, which was one of the sort of first wave of successful search engines. Uh, we went public in 1996, I stayed on through the end of 99 after we had merged with At Home, which was a broadband over cable provider. Ultimately, the combined company met its demise due to, shall we say, the cable companies not really wanting to revenue share this new internet broadband subscription source with a cheeky Silicon Valley startup. Like I said, I left at the end of 1999 and got into venture. Started hanging out at Mobius Venture Capital, which is, which is the firm where Brad and Jason and Seth and I all met. I thought I would hang out there for a short period of time and find another company to start, and instead I found myself becoming really excited about the investing side. I had made a few investments, and then in a somewhat sort of unplanned path, found myself as a full-time VC, and that led to us starting Foundry Gr…

AI assessment note: “led to us starting Foundry Group in 2006”

Q And then, and then we're going to finish on a question from Brad, and this one's hard, so, uh, you've got no escaping this. Your favorite investment?

A My favorite investment. Yeah, that's, uh, that's a real, uh, Brad, that's a real, uh, Sophie's choice. Cause of course I love, uh, you know, I love all of our investments, I would say, and probably the answer, frankly, changes with the recency effect of, you know, how, how much time I've spent, uh, with a particular company most recently. But I would say the investment that I'm sort of proudest of and is at A really interesting scale right now is, you know, one of the early investments we did back in the 2007 fund, which is send grid. Again, a developer focused go to market transactional email for developers. These guys are running at an incredible scale. They send over a billion emails a day. They've been profitable this year and they're an IPO candidate in, uh, in 2017. So I just couldn't be prouder of, uh, sort of how far that company has come and the scale that they're operating at. And again, it's sort of The standards bearer in many ways for this sort of application infrastructure developer focus, you know, investing thesis that I've been working on for, you know, the past several years.

AI assessment note: “one of the early investments we did back in the 2007 fund, which is send grid”

Q And then Brad also asked a second follow-up question, and it's, was it a hard decision for you to make the move to the tech ecosystem now that it is, but it wasn't then of Colorado when you were in SF and moving from Mobius with the next thing being Foundry? Was that a tough decision?

A Yes, it was. I, I think that interestingly, um, and both Both Jason and I moved out to Colorado, and I would say, you know, somewhat surprisingly, if you know perhaps me and Jason and our personality types, you might have expected, you know, Jason to be more methodical in his thought process about, you know, weighing the pros and cons of moving from California to Colorado, and he actually committed to it earlier and easier than I did. Now, you know, I had wife and kid. I'd been there for 17 years. I had been sort of a core part of the sort of Internet One Dot O entrepreneurial ecosystem, and so You know, I did have concerns about moving to Boulder. You know, my wife and I thought we were Bay Area lifers, and so making that move and leaving, quote unquote, the center of the tech universe and moving to Boulder was a big change, and so, you know, it took me a bit longer, both in terms of convincing myself, convincing my wife, et cetera, to, to make the move. Now, all that being said, I spent my junior high and high school years down in Colorado Springs. I had a Brother who went to CU and was living in Boulder. Catherine and I had spent a summer in 2002 before we had our son living out in Boulder next door to Brad and Amy and just working in the Mobius Colorado offices. So after we had spent that summer, you know, Catherine even remarked at one point, hey, if we, if we were ever to…

AI assessment note: “Yes, it was.”

Q Now, I'd love to get started today by hearing a little bit about you and how you came to rock the world of venture with Foundry. What's the brief synopsis?

A Yeah, well, I started out life in the technology industry as an entrepreneur, so I moved out I went to California Bay Area in, in 1989 to go to Stanford as an undergrad, and I met five of my classmates in my freshman dorm, and as we moved on to graduation, decided it would be much more interesting to start a company and work for ourselves rather than someone else, and it was literally that sort of flimsy of motivation that ultimately led us to creating search engine Excite, which was one of the sort of first wave of successful search engines. Uh, we went public in 1996, I stayed on through the end of 99 after we had merged with At Home, which was a broadband over cable provider. Ultimately, the combined company met its demise due to, shall we say, the cable companies not really wanting to revenue share this new internet broadband subscription source with a cheeky Silicon Valley startup. Like I said, I left at the end of 1999 and got into venture. Started hanging out at Mobius Venture Capital, which is, which is the firm where Brad and Jason and Seth and I all met. I thought I would hang out there for a short period of time and find another company to start, and instead I found myself becoming really excited about the investing side. I had made a few investments, and then in a somewhat sort of unplanned path, found myself as a full-time VC, and that led to us starting Foundry Gr…

AI assessment note: “that led to us starting Foundry Group in 2006”

Q And then Brad also asked a second follow-up question, and it's, was it a hard decision for you to make the move to the tech ecosystem now that it is, but it wasn't then of Colorado when you were in SF and moving from Mobius with the next thing being Foundry? Was that a tough decision?

A Yes, it was. I, I think that interestingly, um, and both Both Jason and I moved out to Colorado, and I would say, you know, somewhat surprisingly, if you know perhaps me and Jason and our personality types, you might have expected, you know, Jason to be more methodical in his thought process about, you know, weighing the pros and cons of moving from California to Colorado, and he actually committed to it earlier and easier than I did. Now, you know, I had wife and kid. I'd been there for 17 years. I had been sort of a core part of the sort of Internet One Dot O entrepreneurial ecosystem, and so You know, I did have concerns about moving to Boulder. You know, my wife and I thought we were Bay Area lifers, and so making that move and leaving, quote unquote, the center of the tech universe and moving to Boulder was a big change, and so, you know, it took me a bit longer, both in terms of convincing myself, convincing my wife, et cetera, to, to make the move. Now, all that being said, I spent my junior high and high school years down in Colorado Springs. I had a Brother who went to CU and was living in Boulder. Catherine and I had spent a summer in 2002 before we had our son living out in Boulder next door to Brad and Amy and just working in the Mobius Colorado offices. So after we had spent that summer, you know, Catherine even remarked at one point, hey, if we, if we were ever to…

AI assessment note: “Yes, it was.”

Q I'm intrigued with such a partnership like yours. Is it the one vote says yes in the investments made? What does the investment decision making process look like for you in the partnership at Foundry?

A Technically, uh, three of the four need to vote affirmatively to make, uh, to make an investment decision. I think in practice, all of our investment decisions have been, been unanimous. So, you know, I think all of us would take it really seriously if somebody was, you know, pounding on the table saying, no, we have Absolutely. Should not do this investment. And, and again, we're in the fortunate position of having opportunities to invest in far more great companies and entrepreneurs than we actually have the capacity to do in any given year, right? We do between seven and 10 investments per year, and there, there's probably, you know, 10 times that in terms of companies that we would invest in, in terms of the qualities of the teams or the entrepreneurs, but, you know, we have to, uh, keep a very, a very high bar. So, you know, it tends to be the case that when we are evaluating a company, you know, part of our process often is to get the one among the four of us who's most likely to be skeptical about that particular company or sector or opportunity and get them involved early on in, in the process really as a way to work through our thinking and understand, you know, what the likely sort of points of skepticism and friction will be in the process. And so we kind of do that as a matter of course now, which is again, builds, Builds a lot of efficiency into the decision-making…

AI assessment note: “Technically, uh, three of the four need to vote affirmatively”

Q So as a board member, and when you look back to your first ever board seat that you took, how have you seen yourself develop and change within that board role as a board member?

A I think that, and, and I think my partners would, would, would agree, particularly, uh, particularly Jason, who, you know, knows me really well because we also spend a lot of time doing music together and whatnot. But I would say that, interestingly, when I became a VC, I think it was really partially as it was a personal challenge for me in terms of personal growth with respect to communicating directly, not avoiding conflict, things like that, right? I think I would be the person around the table early on in my board days who would sort of be the last person who was willing to deliver bad news or challenge somebody or Point out something negative. And, uh, you know, I think over time that tension has, has gone away and I've certainly become, you know, become far more direct and comfortable with, um, conflict. And, you know, I think people can do that in a way where, you know, they're still genuine and they're not an asshole, but, uh, it's really important obviously to be able to talk about challenging things. And in fact, that's really the only way you make progress with a company or a business or life or her relationship at the end of the day. And so, So I do think my, my path as a venture capitalist has, I think, really paralleled my sort of personal growth, you know, as a human over the, over the past 17 years as well.

AI assessment note: “I've certainly become, you know, become far more direct and comfortable with, um, conflict.”

Q Yeah, and there's only one road now, but Brad actually has two questions for you, and similar to that, he asked Jason, your partner, when was the transition for you from general counsel to investor? When was the transition for you, when was the catalyst for changing your mindset from entrepreneur and builder looking for the next thing to start to I'm a VC now?

A Well, I think part of it was as I started making some investments, I really became enamored with the sort of portfolio approach, both From, uh, being somebody who has a lot of different interests, and I enjoy the context switching, I enjoy on, sort of, enjoy being able to parallelize, if you will, entrepreneurial efforts, and also, quite frankly, early on, after I had done Excite, I, I found it really hard to commit myself to any one particular idea. I had been doing some angel investing, had been advising a host of companies, and really found that, sort of, being able to parallel process and context It really worked for my interests and personality, and so I sort of found my way into being an investor, uh, as a result of that.

AI assessment note: “after I had done Excite, I, I found it really hard to commit myself”

Q So as a board member, and when you look back to your first ever board seat that you took, how have you seen yourself develop and change within that board role as a board member?

A I think that, and, and I think my partners would, would, would agree, particularly, uh, particularly Jason, who, you know, knows me really well because we also spend a lot of time doing music together and whatnot. But I would say that, interestingly, when I became a VC, I think it was really partially as it was a personal challenge for me in terms of personal growth with respect to communicating directly, not avoiding conflict, things like that, right? I think I would be the person around the table early on in my board days who would sort of be the last person who was willing to deliver bad news or challenge somebody or Point out something negative. And, uh, you know, I think over time that tension has, has gone away and I've certainly become, you know, become far more direct and comfortable with, um, conflict. And, you know, I think people can do that in a way where, you know, they're still genuine and they're not an asshole, but, uh, it's really important obviously to be able to talk about challenging things. And in fact, that's really the only way you make progress with a company or a business or life or her relationship at the end of the day. And so, So I do think my, my path as a venture capitalist has, I think, really paralleled my sort of personal growth, you know, as a human over the, over the past 17 years as well.

AI assessment note: “I've certainly become, you know, become far more direct and comfortable with, um, conflict.”

Q I'm intrigued with such a partnership like yours. Is it the one vote says yes in the investments made? What does the investment decision making process look like for you in the partnership at Foundry?

A Technically, uh, three of the four need to vote affirmatively to make, uh, to make an investment decision. I think in practice, all of our investment decisions have been, been unanimous. So, you know, I think all of us would take it really seriously if somebody was, you know, pounding on the table saying, no, we have Absolutely. Should not do this investment. And, and again, we're in the fortunate position of having opportunities to invest in far more great companies and entrepreneurs than we actually have the capacity to do in any given year, right? We do between seven and 10 investments per year, and there, there's probably, you know, 10 times that in terms of companies that we would invest in, in terms of the qualities of the teams or the entrepreneurs, but, you know, we have to, uh, keep a very, a very high bar. So, you know, it tends to be the case that when we are evaluating a company, you know, part of our process often is to get the one among the four of us who's most likely to be skeptical about that particular company or sector or opportunity and get them involved early on in, in the process really as a way to work through our thinking and understand, you know, what the likely sort of points of skepticism and friction will be in the process. And so we kind of do that as a matter of course now, which is again, builds, Builds a lot of efficiency into the decision-making…

AI assessment note: “Technically, uh, three of the four need to vote affirmatively to make”

Q Yeah, and there's only one road now, but Brad actually has two questions for you, and similar to that, he asked Jason, your partner, when was the transition for you from general counsel to investor? When was the transition for you, when was the catalyst for changing your mindset from entrepreneur and builder looking for the next thing to start to I'm a VC now?

A Well, I think part of it was as I started making some investments, I really became enamored with the sort of portfolio approach, both From, uh, being somebody who has a lot of different interests, and I enjoy the context switching, I enjoy on, sort of, enjoy being able to parallelize, if you will, entrepreneurial efforts, and also, quite frankly, early on, after I had done Excite, I, I found it really hard to commit myself to any one particular idea. I had been doing some angel investing, had been advising a host of companies, and really found that, sort of, being able to parallel process and context It really worked for my interests and personality, and so I sort of found my way into being an investor, uh, as a result of that.

AI assessment note: “after I had done Excite, I, I found it really hard to commit”

Q And talking about kind of the partners that exist within Foundry and the investments, all of you are now board members, obviously, having, having been such experts in the field for so long now. So meta question here, but having seen many boards, what do you think makes the truly brilliant board members?

A I think it's hard to give a blanket answer to that question in the sense that, of course, every board is unique, And it's a, it's comprised of a team of people who each have their own different strengths and weaknesses. I would say much in the same way we place a premium in our partnership in communication. The bigger thing I think we all place a premium on is a high level of self-awareness among ourselves and the entrepreneurs and members of management teams that we work with. And I'd say that sort of self-awareness of, you know, your own role and dynamics in a team, what you bring to the table, what others bring to the table, um, Knowing where your strengths are, where your weaknesses are, that level of having an extreme level of self-awareness, to me, is sort of the, you know, one of the most important aspects of being somebody who's, you know, can contribute well and constructively in a team dynamic, and that's certainly the case on a board, right? And you have people from all sorts of different backgrounds. They may have entrepreneurial experience. They may have senior leadership CEO experience. They may be super techie, You know, they may, um, you know, sort of be able to, uh, you know, glance at a hundred page set of financials and, you know, immediately find like the one, you know, one thing to drill down on that's meaningful.

AI assessment note: “we all place a premium on is a high level of self-awareness”

Q And talking about kind of the partners that exist within Foundry and the investments, all of you are now board members, obviously, having, having been such experts in the field for so long now. So meta question here, but having seen many boards, what do you think makes the truly brilliant board members?

A I think it's hard to give a blanket answer to that question in the sense that, of course, every board is unique, And it's a, it's comprised of a team of people who each have their own different strengths and weaknesses. I would say much in the same way we place a premium in our partnership in communication. The bigger thing I think we all place a premium on is a high level of self-awareness among ourselves and the entrepreneurs and members of management teams that we work with. And I'd say that sort of self-awareness of, you know, your own role and dynamics in a team, what you bring to the table, what others bring to the table, um, Knowing where your strengths are, where your weaknesses are, that level of having an extreme level of self-awareness, to me, is sort of the, you know, one of the most important aspects of being somebody who's, you know, can contribute well and constructively in a team dynamic, and that's certainly the case on a board, right? And you have people from all sorts of different backgrounds. They may have entrepreneurial experience. They may have senior leadership CEO experience. They may be super techie, You know, they may, um, you know, sort of be able to, uh, you know, glance at a hundred page set of financials and, you know, immediately find like the one, you know, one thing to drill down on that's meaningful.

AI assessment note: “having an extreme level of self-awareness, to me, is sort of”

Q But, but, but, but when you invest in Roley, say, how do you, with such passion in, in your kind of physical being about music, how do you remain core to the true, what's the TAM, what's the go-to-market strategy, how brilliant is the team, do they have any IP, you know, the academic approach, is there a, is there an intersection?

A Yeah, there's absolutely an intersection, and I think in, in the case of Roley, it's actually, you know, something, uh, Jason and I had been aware of the company for several years because we would see them at the NAMM conference, uh, Every January down in Anaheim, that's the big sort of musical instruments, you know, annual, annual convention. And so we, we first saw them in this kind of funky new keyboard type instrument, the seaboard that they had developed. And I remember the first year we saw it and we didn't even know they were, they were venture backed and thought, okay, this is interesting. But you know, the sort of opportunity for new instruments to really emerge is, you know, only happens, you know, once every few decades. But we kept seeing them, and, you know, saw more and more buzz around it, and then, you know, they just launched their newest product, Rolly did, just this week, rather just last week, actually, in London, at one of the Apple stores in London, and it's this sort of new category of instrument, the Rolly Block, which is a modular platform that sort of brings the best of, you know, digital and analog music together, really, and sort of enables this It can extremely expressive level of control, but, and also does it in an extremely accessible way, uh, where it's a lower, you know, lower entry price point and the blocks are amazing. So go, you know, go ch…

AI assessment note: “there's absolutely an intersection... Hey, it's a passion, but they're also redefining a category”

Q you have two very clear passions, music and developing and developer centric tools. So talk to me, when investing in spaces that you love as much as you do these, how do you look to retain the same investing discipline and mindset that you would have for other sectors that you're not so inherently passionate about? What are the kind of guidelines you put in place to maintain this level-headedness?

A I think it's a good question, and I think there's, there's two different answers to that. First of all, on, on the music side, I'll come back to that in a second, on the, um, sort of developer-focused Tools and ecosystem, you know, API-driven, self-serve-driven, go-to-market approaches, you know, that are exemplified by sort of a lot of the investments I've made at, uh, at Foundry Group, be it SendGrid or Mapbox or Pantheon as, as, as some examples there. That, for me, is much more, you know, a direct consequence of, you know, what I did at Excite back in the day. I started off life as a software developer, though I haven't You know, written code for money in over 20 years at this point, but that going through the early phases of Excite, where really there was no off-the-shelf internet infrastructure software, Linux was in its infancy, and so we had to build a lot of tools, you know, now that are sort of commonplace and have created entire sort of ecosystems and industries, right? We built server-side scripting languages, application servers, you know, ops tools, and whatnot, and all of those things You know, have become sort of valid ecosystems and industries in their own right over time, and so that really just informed my thinking as a developer in terms of, you know, how important some of these kind of infrastructure-type tools are, and then with the birth and emergence of …

AI assessment note: “I don't think my passion for what's possible there Anything other than an advantage”