The Exchanges

Q Um, Uh, and, and talking about your time at Redpoint there, and how did you meet your investors then for, for accompli?

A So I had met Satish Dharmaraj, who was our lead investor, many years ago when I was CEO of Hyperic. He was CEO of a company called Zimbra, which he, uh, founded as well. And Zimbra was in the email space. They were an open source email server product. Uh, and, uh, They were also, they had the same investors that Hyperic did. They were also doing an open source thing that looked very similar to ours. Also a very successful outcome for, for Zimbra. Um, I had gotten to know Satish over the years, and then he was the one who kind of, uh, uh, convinced me to leave, uh, VMware and, uh, uh, come over and spend time with, with the folks at Redpoint, and, and it was a great, great experience. And so, uh, really it was Satish who initially had the real sort of burning desire to go, uh, do something in mobile email. I was, if anything, if you had asked me in February of 2013 when I was there, you know, midway through my time at Redpoint, if you, Thought I'd be doing an email company and much less be working at Microsoft as a result. I would have said, you're absolutely fucking crazy. But, um, the reality is, is here I am. So, uh.

AI assessment note: “I had met Satish Dharmaraj, who was our lead investor, many years ago”

Q And it's interesting you say there about Axel and Benchmark making great investors. So what makes a great investor for you?

A Another great question. I'm, I'm excited to be here. Um, uh, so the 20 minute VC podcast version of that question is basically a good investor is one that really, uh, Pushes you and inspires you to achieve more than what you think you can deliver, right? And, uh, in my case, uh, when we first, uh, started working with venture investors, uh, we had already bootstrapped the company for two years. We had taken it from a zero dollars to, uh, north of like 1.5 million in bookings, uh, strategic OEM relationships, all the, you know, two dozen customers, all of this, uh, By five guys who had never run a business before, a first time CEO, uh, et cetera, et cetera. So when we got there and started working with, uh, uh, particularly Peter Fenton, who I'm a big fan of and, and who, uh, uh, over the years has been a great friend, uh, who was initially at Excel and now at Benchmark. Peter just, uh, uh, was very good at sort of reminding me that the, the, The real goal, the real, sort of, winning opportunity for, ah, a technology company and a startup, ah, is to, is to build a great, large, enduring company and product, and that that's measured, you know, in a different scale, I think, than what typically, sort of, a more grounded and just equally, ah, valuable, sort of, ah, lifestyle business owner, ah, to use a very, sort of, controversial phrase would think of, right? So, Uh, we thought w…

AI assessment note: “a good investor is one that really, uh, Pushes you and inspires you”

Q Um, Uh, and, and talking about your time at Redpoint there, and how did you meet your investors then for, for accompli?

A So I had met Satish Dharmaraj, who was our lead investor, many years ago when I was CEO of Hyperic. He was CEO of a company called Zimbra, which he, uh, founded as well. And Zimbra was in the email space. They were an open source email server product. Uh, and, uh, They were also, they had the same investors that Hyperic did. They were also doing an open source thing that looked very similar to ours. Also a very successful outcome for, for Zimbra. Um, I had gotten to know Satish over the years, and then he was the one who kind of, uh, uh, convinced me to leave, uh, VMware and, uh, uh, come over and spend time with, with the folks at Redpoint, and, and it was a great, great experience. And so, uh, really it was Satish who initially had the real sort of burning desire to go, uh, do something in mobile email. I was, if anything, if you had asked me in February of 2013 when I was there, you know, midway through my time at Redpoint, if you, Thought I'd be doing an email company and much less be working at Microsoft as a result. I would have said, you're absolutely fucking crazy. But, um, the reality is, is here I am. So, uh.

AI assessment note: “So I had met Satish Dharmaraj, who was our lead investor, many years ago”

Q And it's interesting you say there about Axel and Benchmark making great investors. So what makes a great investor for you?

A Another great question. I'm, I'm excited to be here. Um, uh, so the 20 minute VC podcast version of that question is basically a good investor is one that really, uh, Pushes you and inspires you to achieve more than what you think you can deliver, right? And, uh, in my case, uh, when we first, uh, started working with venture investors, uh, we had already bootstrapped the company for two years. We had taken it from a zero dollars to, uh, north of like 1.5 million in bookings, uh, strategic OEM relationships, all the, you know, two dozen customers, all of this, uh, By five guys who had never run a business before, a first time CEO, uh, et cetera, et cetera. So when we got there and started working with, uh, uh, particularly Peter Fenton, who I'm a big fan of and, and who, uh, uh, over the years has been a great friend, uh, who was initially at Excel and now at Benchmark. Peter just, uh, uh, was very good at sort of reminding me that the, the, The real goal, the real, sort of, winning opportunity for, ah, a technology company and a startup, ah, is to, is to build a great, large, enduring company and product, and that that's measured, you know, in a different scale, I think, than what typically, sort of, a more grounded and just equally, ah, valuable, sort of, ah, lifestyle business owner, ah, to use a very, sort of, controversial phrase would think of, right? So, Uh, we thought w…

AI assessment note: “a good investor is one that really pushes you and inspires you”

Q And, and how was the fundraising process in general for you? Were there any surprises or challenging aspects?

A Not really. You know, we, we were, uh, uh, very, I would say, grounded in our, in our process for, the, the fundraising process was in, in many ways, very simple. Satish and I, after I, I sort of really came up with the, the problem statement and really described the opportunity that I thought existed around mobile email to Satish, he agreed without a doubt. I said, absolutely, this must be done. And I said, okay, well, I think it's going to take, Uh, uh, a significant investment. It's not going to take, uh, you know, seed capital to validate it along the way to blah, blah, blah. And by the way, I'm not into that, right? Like I, if I'm going to go build a company, I'm picking something very hard, uh, on purpose because I've already had, you know, a different kind of opportunity with, with Hyperic, um, which was also hard, by the way. I don't mean to suggest that, that one was actually, if anything, Hyperic was infinitely harder for, for many, many reasons. Um, it was a very short conversation. Satish and I agreed that, that, uh, you know, ostensibly a five million dollar investment was probably what it would take to go build out the product and take it to market and then see what happens. And we were fortunate that in doing that, along the way, the company was generating so much buzz and momentum, even before launching the product, that we were proactively, uh, sort of approach…

AI assessment note: “Not really... the fundraising process was in, in many ways, very simple.”

Q And, and how was the fundraising process in general for you? Were there any surprises or challenging aspects?

A Not really. You know, we, we were, uh, uh, very, I would say, grounded in our, in our process for, the, the fundraising process was in, in many ways, very simple. Satish and I, after I, I sort of really came up with the, the problem statement and really described the opportunity that I thought existed around mobile email to Satish, he agreed without a doubt. I said, absolutely, this must be done. And I said, okay, well, I think it's going to take, Uh, uh, a significant investment. It's not going to take, uh, you know, seed capital to validate it along the way to blah, blah, blah. And by the way, I'm not into that, right? Like I, if I'm going to go build a company, I'm picking something very hard, uh, on purpose because I've already had, you know, a different kind of opportunity with, with Hyperic, um, which was also hard, by the way. I don't mean to suggest that, that one was actually, if anything, Hyperic was infinitely harder for, for many, many reasons. Um, it was a very short conversation. Satish and I agreed that, that, uh, you know, ostensibly a five million dollar investment was probably what it would take to go build out the product and take it to market and then see what happens. And we were fortunate that in doing that, along the way, the company was generating so much buzz and momentum, even before launching the product, that we were proactively, uh, sort of approach…

AI assessment note: “Not really. You know, we, we were, uh, uh, very, I would say, grounded”

Q And if you were to start a startup again, and were to be raising money again, would you do anything differently?

A No, I don't think so. You know, I think from a fundraising perspective, I understand, uh, uh, you know, unlike, I would never claim to be good at raising money. That seems to be, uh, uh, a really sort of shallow skill to cite. It's important, but it's not what makes a great entrepreneur, frankly. Like, oftentimes, the best conversations with potential investors are, uh, uh, really more about, uh, The challenges and, and the big questions that are left to be answered in the path to growing a great company, and less about the terms of the pre and the post and the party pursue and whatever other sort of fun term sheet like BS that you want to cite, right? Like, uh, I remember very distinctly Um, our, uh, when we, when we built Hyperic, I, I just, every time, people just seem, you go to these gatherings, you talk to other entrepreneurs, and everybody was like, hey, what was your valuation, and all this stuff. I'm like, what are you guys fucking talking about? Like, this is, this is not even a real, like, a real market. Like, VC, you know, venture capital is not a true market in the sense that it's a very limited number of players, um, often colluding with Uh, uh, and, and really incestuously sort of managing deal flow back and forth, and, and it works. It, it's an amazing part of the United States, uh, economy, and certainly of the global economy, but it's hardly something to brag …

AI assessment note: “No, I don't think so. You know, I think from a fundraising perspective”

Q And you said about bootstrapping the business there, and then accepting investment. So often when, when that happens, uh, maybe more likely with, uh, inexperienced CEOs and founders as you were, their spending adjusts massively when they suddenly get investment having been bootstrapping. Uh, Uh, did you, how did you kind of control your burn rate?

A Part of the virtue of, of growing a business with zero capital, there was no friends and family money, there was no, all we had was this product that had cost about fifteen million dollars to build, and we had been lucky enough to buy it for a dollar, and, uh, Embarked on this journey, that first bootstrapping journey, knowing that the company was coming, or the product was coming from an over-capitalized scenario, and that the chances of us really being able to make an argument of any kind about further investment in something that was, by many people, including Sequoia, considered a sort of a product in search for a market, and something that was very misguided, um, was It just meant we thought about it very differently, and there was a genuine sense of urgency and consequence. We were all in our early thirties at the time. Some of us had kids. I didn't, but, you know, two of my business partners had kids. And you become very, very good at sort of managing around scarcity, and it's very clarifying, frankly. So in the transition from that into being a well-capitalized, you know, top-tier venture-backed company, The seed of the soul of the company was planted around this idea of winning customers was the only thing that mattered, because it's what kept us alive. And, uh, in a sense, I became very, I don't know that it was cynical. I was always very cautious, I guess, of the, th…

AI assessment note: “you become very, very good at sort of managing around scarcity”

Q And if you were to start a startup again, and were to be raising money again, would you do anything differently?

A No, I don't think so. You know, I think from a fundraising perspective, I understand, uh, uh, you know, unlike, I would never claim to be good at raising money. That seems to be, uh, uh, a really sort of shallow skill to cite. It's important, but it's not what makes a great entrepreneur, frankly. Like, oftentimes, the best conversations with potential investors are, uh, uh, really more about, uh, The challenges and, and the big questions that are left to be answered in the path to growing a great company, and less about the terms of the pre and the post and the party pursue and whatever other sort of fun term sheet like BS that you want to cite, right? Like, uh, I remember very distinctly Um, our, uh, when we, when we built Hyperic, I, I just, every time, people just seem, you go to these gatherings, you talk to other entrepreneurs, and everybody was like, hey, what was your valuation, and all this stuff. I'm like, what are you guys fucking talking about? Like, this is, this is not even a real, like, a real market. Like, VC, you know, venture capital is not a true market in the sense that it's a very limited number of players, um, often colluding with Uh, uh, and, and really incestuously sort of managing deal flow back and forth, and, and it works. It, it's an amazing part of the United States, uh, economy, and certainly of the global economy, but it's hardly something to brag …

AI assessment note: “No, I don't think so. You know, I think from a fundraising perspective”

Q And you said about bootstrapping the business there, and then accepting investment. So often when, when that happens, uh, maybe more likely with, uh, inexperienced CEOs and founders as you were, their spending adjusts massively when they suddenly get investment having been bootstrapping. Uh, Uh, did you, how did you kind of control your burn rate?

A Part of the virtue of, of growing a business with zero capital, there was no friends and family money, there was no, all we had was this product that had cost about fifteen million dollars to build, and we had been lucky enough to buy it for a dollar, and, uh, Embarked on this journey, that first bootstrapping journey, knowing that the company was coming, or the product was coming from an over-capitalized scenario, and that the chances of us really being able to make an argument of any kind about further investment in something that was, by many people, including Sequoia, considered a sort of a product in search for a market, and something that was very misguided, um, was It just meant we thought about it very differently, and there was a genuine sense of urgency and consequence. We were all in our early thirties at the time. Some of us had kids. I didn't, but, you know, two of my business partners had kids. And you become very, very good at sort of managing around scarcity, and it's very clarifying, frankly. So in the transition from that into being a well-capitalized, you know, top-tier venture-backed company, The seed of the soul of the company was planted around this idea of winning customers was the only thing that mattered, because it's what kept us alive. And, uh, in a sense, I became very, I don't know that it was cynical. I was always very cautious, I guess, of the, th…

AI assessment note: “I was always very cautious, I guess, of the, the, the responsibility that comes”

Q Yeah. And what were your reasons for selling then?

A By the time we start, started having more serious conversations with Microsoft, we had, uh, We were in the middle of a transition from a deeply loved and widely adopted end user email application into a where, what is the enterprise, uh, sort of business that you're going to build around this product. In other words, how are you going to make money? Like, what is really the, the, where's the business? Other than this, you know, great app, what, what else is there? Um, at the time, We were very, very, very fortunate to already have, like, multiple millions of dollars of, of sales pipeline, and customers actually, uh, two in Europe, one in the UK, and two in the US, who were working with us very closely to, uh, uh, really sign up and, and craft what would become the accompli enterprise service, uh, and I was pretty excited about that. That's the part of the business that I was, You know, much more familiar with. It really, uh, uh, was, it's kind of an exciting transition into, you know, really growing up as a, as a team and as a company. Um, and as we were going through these, uh, uh, early customer conversations, it was very, uh, interesting to see, you know, how eager people were to have this problem be solved, and then sort of be reminded of the importance of, of vendor credibility and the difficulty that you, you had to walk through to establish yourself as somebody who can r…

AI assessment note: “be reminded of the importance of, of vendor credibility and the difficulty”

Q Yeah. And what were your reasons for selling then?

A By the time we start, started having more serious conversations with Microsoft, we had, uh, We were in the middle of a transition from a deeply loved and widely adopted end user email application into a where, what is the enterprise, uh, sort of business that you're going to build around this product. In other words, how are you going to make money? Like, what is really the, the, where's the business? Other than this, you know, great app, what, what else is there? Um, at the time, We were very, very, very fortunate to already have, like, multiple millions of dollars of, of sales pipeline, and customers actually, uh, two in Europe, one in the UK, and two in the US, who were working with us very closely to, uh, uh, really sign up and, and craft what would become the accompli enterprise service, uh, and I was pretty excited about that. That's the part of the business that I was, You know, much more familiar with. It really, uh, uh, was, it's kind of an exciting transition into, you know, really growing up as a, as a team and as a company. Um, and as we were going through these, uh, uh, early customer conversations, it was very, uh, interesting to see, you know, how eager people were to have this problem be solved, and then sort of be reminded of the importance of, of vendor credibility and the difficulty that you, you had to walk through to establish yourself as somebody who can r…

AI assessment note: “be reminded of the importance of, of vendor credibility and the difficulty”