The Exchanges

Q That is hilarious. I wish I had been there for one of the John Fine knowledge bombs in the early days. I want to finish today, John, on your most recent publicly announced investment, and why did you say yes?

A Probably the most, the most recent publicly announced investment was in a company called The Mint, and The Mint is a hotel-style housekeeping service for multi-tenant buildings, and we had been tracking them for about a year before we invested. And so by the time we really engaged, they had, first of all, they had incredible traction. And what's really was a complete reflection of the founder, Kathleen Wilson, who is fantastic. Um, they're based in Chicago and they sell their services to, to multi-tenant buildings. And by the time we got some, they had already signed on a multitude of property managers, including two of the largest multi-tenant property managers in the U S clearly were onto something. And so we were thrilled to invest in, and, We have followed on since then, and it's one of our fastest growing companies in our portfolio now, so it's been absolutely fantastic.

AI assessment note: “by the time we really engaged, they had, first of all, they had incredible traction.”

Q be too afraid by that. And even if actually they want to do it and they just can't fit the timeline, they'll probably tell you anyway. But I do want to ask, and it's a question from Brad. Well, it's two actually. He says, were you surprised by the amount of time it took to raise the first fund? And what advice did you get that really stuck with you?

A Yeah, I wasn't surprised, but I didn't like it. I'm not a patient person by nature. And so I knew the data, right? I knew that at that time, I, you know, I think I'd read something in 2016 that the average amount of time it takes to raise a first fund is 17 months. And of course, you know, I'm, I go in there thinking, well, not for me, you know, I'm not going to take that long. And so as it went on, it was, it's actually funny because, and that this question is coming from Brad, because I had dinner with Brad and one of his partners, Lindell, about halfway through my raise. I was in Boulder. It was like one of these really raw winter Boulder evenings. And I still remember Brad was a real trooper because he had to go to the dentist. He had like some dental work done or something with his tooth. And he still came out for dinner and we were halfway through our raise and we had hit our Minimum target, which was seven million. And one of the questions, I just peppered them with questions the entire dinner. I'm sure it was very annoying. And one of the questions I had was we hit our minimum. Should I just stop? Am I done? And of course, looking back, they were like, no, what are you talking about? You're not done. Like you're never going to be done fundraising anyway. You're always gonna be fundraising in some way. Like keep going, see how much you can raise. And that was, you know, …

AI assessment note: “Yeah, I wasn't surprised, but I didn't like it.”

Q Harry, once you have your anchor, you're done. You're practically done. Harry, once you're halfway there, you're done. It'll be easy from there. 75%. Oh, now it's Easy, Harry. Tell me, with every stage, everyone said it would be easy. Did you find the same, and did you find there was an inflection point when suddenly the table did flip, and it did become a little more fluid and easy?

A It never got easy. It got a little easier, but it never got easy. Our anchor came in in our second close, and again, this was a very well-known person in our community, and it made it a little easier. To me, the easiest part was just mentally taking a Fund was to a size where I felt like, okay, this is going to happen. I'm actually going to be able to raise this fund. I'm actually going to be able to have an income from this fund. To me, that was the part that got easier. The raise itself never got easy. It didn't get easy after 50%. It didn't get easy after 75. All the way through, and we experienced the same thing that a lot of VCs experience, is a big percentage of our fund was raised fairly close to the final close. You know, when you put a deadline in front of people, that's when they tend to really get off the fence, and that happened with us, too.

AI assessment note: “It never got easy. It got a little easier, but it never got easy.”

Q I, I love everything about it, but it does mean maybe there's more meeting requests and inbound than maybe most. How do you advise me on the right way to say no? It's something that I can never get comfortable with, as you said. What have you found tends to work and is a gracious way to not sound arrogant, but also just preserves your time when you have to?

A Yeah, it's always the ongoing struggle, and I heard this advice. I forget who said it, but it was this phrase that I really loved, and the I'm sorry, I can't right now, and I love it because it's super direct, but you actually are sorry that you can't meet with this person, but also making it clear that your plate is completely full, and your job is to focus on these things right now. It doesn't mean that you're never going to be able to meet with this person, just that right now, it's just not possible, and so I use a variation of that when I respond, and I feel like it's not ever, you know, something I feel great about, but it's sort of, you know, that's what the situation is, and You know, you're at least expressing a little bit of remorse that you can't meet with everybody that you really would love to meet with. I used to have this whole, like, canned text thing. It's like this paragraph that was really descriptive, like, well, I'd love to meet with everyone who asks. I really can't because right now in the middle of all of that, I was like, I don't need to explain every single little thing. I just need to get across the fact that I really would love to, but just not able to right now.

AI assessment note: “I'm sorry, I can't right now, and I love it because it's super direct”

Q over the time is the relationship with the founder, and it was really interesting when we chatted before. You said a couple of really striking things about the VC to founder relationship, and what was starting on the first was the importance of building trust with the founder before writing the check. So I love this, but I couldn't agree more. However, what's your framework and process for doing so?

A We've been fortunate on a handful of occasions where we've, we've already known the founders for years, and that's easy. That's an easy one to solve. There's already relationships, there's already trust there. I would say for most of our investments, you know, we don't know them super well, or maybe we've been recently introduced to them. And as you mentioned in the past, it's sort of this compressed time period where all of a sudden you have to get to know each other. And in our minds, you know, one of the most important parts of that is you can't completely build this amazing trusting relationship in four weeks, but you can put the foundation in place. And so through these touch points, I think paying close attention to each touch point that you have is super, super important. Paying attention to the details, how the founder reacts, how the founder, how they do what they say they're going to do, what they're saying they're going to do. And also probably the most important part of our evaluation process is when we have a face-to-face meeting with the founders, because sometimes we only end up having one face-to-face meeting if they're not local to us. And the What we'll do is we'll typically, we'll go to them, we'll fly into their city, we'll spend several hours with follow-up questions that we've had from the previous phone calls or video calls we've had with them, and then w…

AI assessment note: “dinner is the most important part to me because it kind of tends to let the guard down”

Q much cash in the ecosystem? In a case, I met a very young first-time founder recently, went out to raise 300 K, clearly from an engineering perspective, phenomenally talented, soon was bid up to a three million round on a 12 pre, and that's not unusual. Is that just too much cash then in these core hubs, do you think? How do you think about that, if you were me?

A There's a lot of capital, and valuations are higher, and that does make it more challenging for us. I mean, certainly our target valuation has changed, like I'm sure everybody's has in the past three years. But, you know, we also try to counsel founders to not overextend early on. I think everyone, not everyone, but I think a lot of founders are right from the get go are just going for the highest possible valuation at the earliest possible round. And as you very well know, Harry, I've heard you talk about this a little bit on your show with other investors. I mean, that, that can back founders into a corner and it gets you, you don't want founders to back themselves into a situation where they have to execute perfectly. Because nobody does. And in order to get to the next required valuation for their next round. And so that's sort of how we think about the capital that's in the system and the, and the resulting, you know, higher valuations that have happened. It's been a trend. You can't fight it, but you know what? That trend is not going to last forever. This boom economy is not going to last forever. Everything's cyclical. I've worked through two recessions so far, and you know, it's, it's going to come back down. So the main thing is you want to build a sustainable business, a high growth business where you have room to To get to that next plateau and achieve your mileston…

AI assessment note: “There's a lot of capital, and valuations are higher, and that does make it more challenging”

Q ground and up and running. And so I do want to start with that and really kind of a really interesting element. Let's start with that actually. So the cool part obviously of the fund is the fund itself. And for you raising the first time fund in maybe a more financially conservative Midwest. So how was that for you without knowing any of the super high net worth community?

A Simultaneously exciting and terrifying, I would say. So what I did early on is sort of like a forcing mechanism is sort of contrary to the advice of my attorneys publicly announced it. And so I stayed away from a fundraising talk, but I publicly announced the fact that Firebrand was going to exist before I had raised one dollar for the fund. So it sort of put even more pressure on me to make this thing happen. And as it turned out, it was a good call. I had no idea what I was doing, but had hoped that that was going to get some momentum going and get the word out. At least in the region. And so that helped a little bit build some awareness. And I started really what I did is I just started with one or two people. I still remember I had an early supporter who himself didn't invest right away, but I went to him. He's a very well-known person in Kansas City and a big, huge champion for the ecosystem and has done a lot for it. And I sat down with him for the very first time. And I said, you know, I'm raising this fund. The So I think I'm going to be able to raise maybe one or two million in Kansas City, and then I'm going to go outside to my broader network and raise the rest. And he said, no, no, no, you're not going to do that. You're going to raise the whole thing here in Kansas City. I was like, okay, well, maybe if you can help me do that, I will go for it. And he did. He made…

AI assessment note: “Simultaneously exciting and terrifying, I would say.”

Q mean, eight weeks is an incredibly short time frame, so congrats on that. Can I ask, in terms of your closing strategy, what was your closing strategy? Was it when you had a certain amount on the table, you'd take it off, Was it, we're going to plan three closings, and that's very formulaic and structured. How did you think about closing and the right time to close on what?

A Yeah, hats off to our fund administrator, because they have a lot of experience in this field, and they're big advocates of when there's a certain amount of money on the table, you just do a close. You don't want to leave it hanging out there for too long. And I would say maybe that's especially true in Midwest communities where you may not have as many LPs that have invested in a lot of different venture funds. So for quite a few of our LPs, Firebrand was the first fund they've ever invested in, and so it worked out roughly to about, looking back, about every quarter, we ended up doing a close, and it was definitely great that I got in, and that's how we just repeated that pattern until we did our final close.

AI assessment note: “when there's a certain amount of money on the table, you just do a close.”

Q the fund size. I always remember a friend of mine, Dan at Maveron says, Harry, your fund size is your strategy. And I always remember that one. I do want to dig in a little bit more into now in terms of managing the fund itself. What are the biggest challenges in terms of the fund management and really running of the funds, so to speak, day to day today?

A Sure. Well, in the beginning, it was just me. And so I It was all the challenges that a sole partner has. You have to time management and prioritization. That's what it was all about. And it's still about that, especially when it's just a sole partner. And so I think early on, it was like, the good news is it's just me. I feel like I have this independence and, you know, it's just, it's just my decisions. And the bad news was, it was just me. It was, oh no, what if I screw up? What if I make a bad decision? I mean, I had some great advisors, That were formal advisors to the fund, and they've been fantastic, but still, it's not quite the same as having a peer partner to bounce things off of, and someone who can really challenge the biases that you have, and so that was a big challenge early on, I would say, and then the other one is just bandwidth. When you're starting out, and you have a small team, and in this case, it was just me for the first about year and a half, it's like, how many different places can I be at the same time? How many different things can I do? I was on four boards in the community. I had to step off all but one I just start saying no a lot, which took some getting used to, and it's not an enjoyable thing to turn down meetings and things like that, especially when it's folks in our community, but like, I had to really focus on making investments, raising c…

AI assessment note: “time management and prioritization. That's what it was all about.”

Q I would absolutely have loved to have seen that canned one. But I do want to ask, with the benefit of hindsight now, there's a lot of prospective fund managers who this What advice do you wish you'd been told when you started? What should they know?

A You know, I kind of knew this early on, but I think it just bears repeating. And the wonderful thing now is I was given all this incredible advice early on. So I was incredibly lucky to have known all these VCs right from the start. And now I get asked for feedback from new fund managers who are raising, especially those who are raising between the coasts. And one of the things that I tell them is two things. One is it's not a hobby. It's not something to do. You know, just because it seems like a good idea at the time, this is a long-term game. Venture is a long game. Every fund that you raise, you're making a ten-plus-year commitment to your LPs and to your companies, and so first of all, you have to be thinking long-term, and also, this is not a career for someone who needs frequent positive feedback. The feedback loops are very long. You're not going to know how you're doing for at least five years, and you're not going to have someone who's there on a regular basis saying what a great job you're doing, and there are some types of people that like that, and there's Absolutely nothing wrong with it, but if you need that frequent positive input that you're doing this amazing job, it's probably not the best fit. On the flip side, if you love building for the long term, and you love doing it for the sake of helping founders, and you have a true obsession and passion for being a…

AI assessment note: “this is not a career for someone who needs frequent positive feedback”

Q absolutely love these conversations. You mentioned kind of the need for perfect execution in those cases. You also need perfect execution if you're a little bit light on the runway side. How do you think about, at this stage specifically, the right amount of time to raise for? I always err on the side of 24 over 18, just for that little extra buffer. How do you think about it?

A Yeah, I used to suggest 18, and now we say 24, and it's mainly just because of the uncertainty that's out there. With the economy right now, and it's just, you know, better safe than sorry. I think 24 is a safe number, but also, I think it's important, while you can't necessarily predict all of the rounds that you're going to raise, nor should you, I do think it's important to think your fundraising strategy sort of as a chess match, and that you're thinking two to three moves ahead, and so that ties back to not necessarily taking the very, very highest valuation you could get, because you want to leave yourself room. Same thing goes for runway. You want to make sure you have enough runway to get to the next stage, and if you think you'll need to raise another one, two, three rounds, however much it is, making sure that at least you're planful about it, and making sure, obviously, that you have enough cash in the bank, and more than anything, it's not optimizing for your round, it's optimizing for your milestones. It's all about what milestones you're going to achieve with this capital to make it even possible to either raise the next round, maybe you don't need to raise the next round, maybe you can go Some number of years, maybe even forever without raising another round. I have a great deal of respect for startups that don't necessarily conform to it's a C, then it's a C plu…

AI assessment note: “I used to suggest 18, and now we say 24, and it's mainly just because of the uncertainty”

Q think of Qualtrics as the example to that, and what an incredible story that was. I do want to ask you, we mentioned kind of milestones to hit, and on the investor side, when investing, a lot of What we want to hit is often ownership centric. I'm intrigued. How do you think about ownership? And more importantly, maybe, how do you think about ownership and increasing ownership over time?

A We assume that we won't be able to. So we assume that the ownership we get with our first check is going to be it, and that the best we're going to be able to do after that is to maintain that ownership over time. And we probably won't be able to forever. You know, as a relatively small seed fund, eventually, you If the startup is going to continue to raise a C, a D, an E, and onward, we're going to get diluted, but we don't assume that we can build ownership over time. Having said that, we will certainly take that opportunity, especially in that seed phase that Hunter talked about, that if we can increase ownership in one of those subsequent seed rounds or seed extensions, of course, you know, if the company is doing great, we jump on that opportunity, and we've done that, and so that's how we think about it. We don't want to assume Assume that we can build on ownership over time, but if we can, and it makes sense for us to do it, of course, we love doing that.

AI assessment note: “We assume that we won't be able to. So we assume that the ownership”

Q Listen, I think we're hugely aligned on, on the way we think about building the relationships. It's interesting. Puneet at True Ventures said on the show last week, he said, um, the best firms of the next decade will be separated by EQ. Would you agree with that? It sounds very much so from your approach, but would you agree with that?

A Totally agree. You know, I think there's a lot to be said for not, uh, Pretending that you have it all figured out where as an investor, you know, your strengths, you know, your weaknesses, you know how to say, I don't know, but we're going to get you the answer. Somehow someone else is, we're going to bring someone else in to help. I just think it's hugely important. I mean, let's face it, you know, like nobody has it all figured out. We're all works in progress. The learning is the most important part. We look for a learning mindset and the founders we invest in, and we have to have a learning mindset too. And so that's a lot of how we think about What our job is as far as how we help founders and also the relationship to founders is that we just try to be authentic. We're just sort of what you see is what you get. And if they like that and they're aligned with our approach, awesome. And if they're not, that's okay too. And maybe there's, there's not going to be a long-term fit, but that's just how we operate. And because we know at the end of the day, our job is to help. And if we're not helping our founders when they need us, then we're failing. And it's not going to be us having all the answers and And claiming to be able to build their business or be this, like, hugely integral part of, like, they couldn't do this without us, and if it wasn't for us, it would have failed.…

AI assessment note: “Totally agree. You know, I think there's a lot to be said”

Q Ok, so what's your favorite book and why?

A It's by Jerry Colonna, and it's just a fantastic book. It's all about radical self-inquiry. Um, so we're just talking about EQ, and a lot of it is about understanding sort of these self-defeating patterns that we sometimes fall into our habits that were actually formed during childhood, and it's about understanding those, identifying them. Jerry has this wonderful phrase that he uses this question, which is, how have I been complicit in creating the conditions I say I don't want? And it's not that everyone is responsible for the problems they have. It's what role have we played in sort of creating these conditions and how can you break out of them? The subtitle of the book is called leadership and the art of growing up. And it's not growing up like a grow up, you know, this condescending thing it's, it's growing up as in growing out of these habits that have been ingrained in you for so many years. So it's, it's a wonderful book for founders and for investors, anybody.

AI assessment note: “It's by Jerry Colonna, and it's just a fantastic book.”

Q ground and up and running. And so I do want to start with that and really kind of a really interesting element. Let's start with that actually. So the cool part obviously of the fund is the fund itself. And for you raising the first time fund in maybe a more financially conservative Midwest. So how was that for you without knowing any of the super high net worth community?

A Simultaneously exciting and terrifying, I would say. So what I did early on is sort of like a forcing mechanism is sort of contrary to the advice of my attorneys publicly announced it. And so I stayed away from a fundraising talk, but I publicly announced the fact that Firebrand was going to exist before I had raised one dollar for the fund. So it sort of put even more pressure on me to make this thing happen. And as it turned out, it was a good call. I had no idea what I was doing, but had hoped that that was going to get some momentum going and get the word out. At least in the region. And so that helped a little bit build some awareness. And I started really what I did is I just started with one or two people. I still remember I had an early supporter who himself didn't invest right away, but I went to him. He's a very well-known person in Kansas City and a big, huge champion for the ecosystem and has done a lot for it. And I sat down with him for the very first time. And I said, you know, I'm raising this fund. The So I think I'm going to be able to raise maybe one or two million in Kansas City, and then I'm going to go outside to my broader network and raise the rest. And he said, no, no, no, you're not going to do that. You're going to raise the whole thing here in Kansas City. I was like, okay, well, maybe if you can help me do that, I will go for it. And he did. He made…

AI assessment note: “Simultaneously exciting and terrifying, I would say.”

Q Harry, once you have your anchor, you're done. You're practically done. Harry, once you're halfway there, you're done. It'll be easy from there. 75%. Oh, now it's Easy, Harry. Tell me, with every stage, everyone said it would be easy. Did you find the same, and did you find there was an inflection point when suddenly the table did flip, and it did become a little more fluid and easy?

A It never got easy. It got a little easier, but it never got easy. Our anchor came in in our second close, and again, this was a very well-known person in our community, and it made it a little easier. To me, the easiest part was just mentally taking a Fund was to a size where I felt like, okay, this is going to happen. I'm actually going to be able to raise this fund. I'm actually going to be able to have an income from this fund. To me, that was the part that got easier. The raise itself never got easy. It didn't get easy after 50%. It didn't get easy after 75. All the way through, and we experienced the same thing that a lot of VCs experience, is a big percentage of our fund was raised fairly close to the final close. You know, when you put a deadline in front of people, that's when they tend to really get off the fence, and that happened with us, too.

AI assessment note: “It never got easy. It got a little easier, but it never got easy.”

Q I would absolutely have loved to have seen that canned one. But I do want to ask, with the benefit of hindsight now, there's a lot of prospective fund managers who this What advice do you wish you'd been told when you started? What should they know?

A You know, I kind of knew this early on, but I think it just bears repeating. And the wonderful thing now is I was given all this incredible advice early on. So I was incredibly lucky to have known all these VCs right from the start. And now I get asked for feedback from new fund managers who are raising, especially those who are raising between the coasts. And one of the things that I tell them is two things. One is it's not a hobby. It's not something to do. You know, just because it seems like a good idea at the time, this is a long-term game. Venture is a long game. Every fund that you raise, you're making a ten-plus-year commitment to your LPs and to your companies, and so first of all, you have to be thinking long-term, and also, this is not a career for someone who needs frequent positive feedback. The feedback loops are very long. You're not going to know how you're doing for at least five years, and you're not going to have someone who's there on a regular basis saying what a great job you're doing, and there are some types of people that like that, and there's Absolutely nothing wrong with it, but if you need that frequent positive input that you're doing this amazing job, it's probably not the best fit. On the flip side, if you love building for the long term, and you love doing it for the sake of helping founders, and you have a true obsession and passion for being a…

AI assessment note: “One is it's not a hobby... you're making a ten-plus-year commitment”

Q absolutely love these conversations. You mentioned kind of the need for perfect execution in those cases. You also need perfect execution if you're a little bit light on the runway side. How do you think about, at this stage specifically, the right amount of time to raise for? I always err on the side of 24 over 18, just for that little extra buffer. How do you think about it?

A Yeah, I used to suggest 18, and now we say 24, and it's mainly just because of the uncertainty that's out there. With the economy right now, and it's just, you know, better safe than sorry. I think 24 is a safe number, but also, I think it's important, while you can't necessarily predict all of the rounds that you're going to raise, nor should you, I do think it's important to think your fundraising strategy sort of as a chess match, and that you're thinking two to three moves ahead, and so that ties back to not necessarily taking the very, very highest valuation you could get, because you want to leave yourself room. Same thing goes for runway. You want to make sure you have enough runway to get to the next stage, and if you think you'll need to raise another one, two, three rounds, however much it is, making sure that at least you're planful about it, and making sure, obviously, that you have enough cash in the bank, and more than anything, it's not optimizing for your round, it's optimizing for your milestones. It's all about what milestones you're going to achieve with this capital to make it even possible to either raise the next round, maybe you don't need to raise the next round, maybe you can go Some number of years, maybe even forever without raising another round. I have a great deal of respect for startups that don't necessarily conform to it's a C, then it's a C plu…

AI assessment note: “I used to suggest 18, and now we say 24, and it's mainly just”

Q over the time is the relationship with the founder, and it was really interesting when we chatted before. You said a couple of really striking things about the VC to founder relationship, and what was starting on the first was the importance of building trust with the founder before writing the check. So I love this, but I couldn't agree more. However, what's your framework and process for doing so?

A We've been fortunate on a handful of occasions where we've, we've already known the founders for years, and that's easy. That's an easy one to solve. There's already relationships, there's already trust there. I would say for most of our investments, you know, we don't know them super well, or maybe we've been recently introduced to them. And as you mentioned in the past, it's sort of this compressed time period where all of a sudden you have to get to know each other. And in our minds, you know, one of the most important parts of that is you can't completely build this amazing trusting relationship in four weeks, but you can put the foundation in place. And so through these touch points, I think paying close attention to each touch point that you have is super, super important. Paying attention to the details, how the founder reacts, how the founder, how they do what they say they're going to do, what they're saying they're going to do. And also probably the most important part of our evaluation process is when we have a face-to-face meeting with the founders, because sometimes we only end up having one face-to-face meeting if they're not local to us. And the What we'll do is we'll typically, we'll go to them, we'll fly into their city, we'll spend several hours with follow-up questions that we've had from the previous phone calls or video calls we've had with them, and then w…

AI assessment note: “we'll fly into their city, we'll spend several hours... and then we'll go out to dinner”

Q mean, eight weeks is an incredibly short time frame, so congrats on that. Can I ask, in terms of your closing strategy, what was your closing strategy? Was it when you had a certain amount on the table, you'd take it off, Was it, we're going to plan three closings, and that's very formulaic and structured. How did you think about closing and the right time to close on what?

A Yeah, hats off to our fund administrator, because they have a lot of experience in this field, and they're big advocates of when there's a certain amount of money on the table, you just do a close. You don't want to leave it hanging out there for too long. And I would say maybe that's especially true in Midwest communities where you may not have as many LPs that have invested in a lot of different venture funds. So for quite a few of our LPs, Firebrand was the first fund they've ever invested in, and so it worked out roughly to about, looking back, about every quarter, we ended up doing a close, and it was definitely great that I got in, and that's how we just repeated that pattern until we did our final close.

AI assessment note: “they're big advocates of when there's a certain amount of money on the table”

Q the fund size. I always remember a friend of mine, Dan at Maveron says, Harry, your fund size is your strategy. And I always remember that one. I do want to dig in a little bit more into now in terms of managing the fund itself. What are the biggest challenges in terms of the fund management and really running of the funds, so to speak, day to day today?

A Sure. Well, in the beginning, it was just me. And so I It was all the challenges that a sole partner has. You have to time management and prioritization. That's what it was all about. And it's still about that, especially when it's just a sole partner. And so I think early on, it was like, the good news is it's just me. I feel like I have this independence and, you know, it's just, it's just my decisions. And the bad news was, it was just me. It was, oh no, what if I screw up? What if I make a bad decision? I mean, I had some great advisors, That were formal advisors to the fund, and they've been fantastic, but still, it's not quite the same as having a peer partner to bounce things off of, and someone who can really challenge the biases that you have, and so that was a big challenge early on, I would say, and then the other one is just bandwidth. When you're starting out, and you have a small team, and in this case, it was just me for the first about year and a half, it's like, how many different places can I be at the same time? How many different things can I do? I was on four boards in the community. I had to step off all but one I just start saying no a lot, which took some getting used to, and it's not an enjoyable thing to turn down meetings and things like that, especially when it's folks in our community, but like, I had to really focus on making investments, raising c…

AI assessment note: “time management and prioritization. That's what it was all about.”

Q think of Qualtrics as the example to that, and what an incredible story that was. I do want to ask you, we mentioned kind of milestones to hit, and on the investor side, when investing, a lot of What we want to hit is often ownership centric. I'm intrigued. How do you think about ownership? And more importantly, maybe, how do you think about ownership and increasing ownership over time?

A We assume that we won't be able to. So we assume that the ownership we get with our first check is going to be it, and that the best we're going to be able to do after that is to maintain that ownership over time. And we probably won't be able to forever. You know, as a relatively small seed fund, eventually, you If the startup is going to continue to raise a C, a D, an E, and onward, we're going to get diluted, but we don't assume that we can build ownership over time. Having said that, we will certainly take that opportunity, especially in that seed phase that Hunter talked about, that if we can increase ownership in one of those subsequent seed rounds or seed extensions, of course, you know, if the company is doing great, we jump on that opportunity, and we've done that, and so that's how we think about it. We don't want to assume Assume that we can build on ownership over time, but if we can, and it makes sense for us to do it, of course, we love doing that.

AI assessment note: “We assume that we won't be able to. So we assume that the ownership”

Q Ok, so what's your favorite book and why?

A It's by Jerry Colonna, and it's just a fantastic book. It's all about radical self-inquiry. Um, so we're just talking about EQ, and a lot of it is about understanding sort of these self-defeating patterns that we sometimes fall into our habits that were actually formed during childhood, and it's about understanding those, identifying them. Jerry has this wonderful phrase that he uses this question, which is, how have I been complicit in creating the conditions I say I don't want? And it's not that everyone is responsible for the problems they have. It's what role have we played in sort of creating these conditions and how can you break out of them? The subtitle of the book is called leadership and the art of growing up. And it's not growing up like a grow up, you know, this condescending thing it's, it's growing up as in growing out of these habits that have been ingrained in you for so many years. So it's, it's a wonderful book for founders and for investors, anybody.

AI assessment note: “It's by Jerry Colonna, and it's just a fantastic book. It's all about”

Q That is very kind, and you know how to get my ego going, but I do want to start with a little bit on you. So tell me, how did you make your way into, as I always call it, the wonderful world of venture, and come to found Firebrand?

A Sure. My road to venture has been a winding one. I'm originally from a town right outside Boston, Massachusetts called Brookline. My dad worked for Digital Equipment Corporation for years. Right from the time when I was about nine years old, I was on a computer. Actually, it wasn't a computer. It was a terminal in this Vax BMS terminal in our basement, which was weird at that time to be nine years old and to be on a computer. Really, nobody did that, and so I always had a love of computers from a very early age, but I actually went to college for psychology. I got a degree in psychology. At the time, that's the I thought I wanted to go into. I learned soon thereafter, graduating, that that just wasn't for me, and so I gravitated to the only thing I really knew at that time, which was computers and technology, and so I ended up moving to Southern California about a year after I graduated, which was one of the times in my career that was just fortunate because I got there soon before the internet boom, and I joined my first startup in 97, and it was great because the The startup had a big office in San Diego, which is where I was living, but they had a headquarters in Silicon Valley. And so I also got a really good taste of what it was like to be in the Valley during the internet boom, which was, which was incredible. And I worked for a succession of five startups during that tim…

AI assessment note: “My road to venture has been a winding one. I'm originally from a town”

Q That is very kind, and you know how to get my ego going, but I do want to start with a little bit on you. So tell me, how did you make your way into, as I always call it, the wonderful world of venture, and come to found Firebrand?

A Sure. My road to venture has been a winding one. I'm originally from a town right outside Boston, Massachusetts called Brookline. My dad worked for Digital Equipment Corporation for years. Right from the time when I was about nine years old, I was on a computer. Actually, it wasn't a computer. It was a terminal in this Vax BMS terminal in our basement, which was weird at that time to be nine years old and to be on a computer. Really, nobody did that, and so I always had a love of computers from a very early age, but I actually went to college for psychology. I got a degree in psychology. At the time, that's the I thought I wanted to go into. I learned soon thereafter, graduating, that that just wasn't for me, and so I gravitated to the only thing I really knew at that time, which was computers and technology, and so I ended up moving to Southern California about a year after I graduated, which was one of the times in my career that was just fortunate because I got there soon before the internet boom, and I joined my first startup in 97, and it was great because the The startup had a big office in San Diego, which is where I was living, but they had a headquarters in Silicon Valley. And so I also got a really good taste of what it was like to be in the Valley during the internet boom, which was, which was incredible. And I worked for a succession of five startups during that tim…

AI assessment note: “My road to venture has been a winding one.”

Q I, I love everything about it, but it does mean maybe there's more meeting requests and inbound than maybe most. How do you advise me on the right way to say no? It's something that I can never get comfortable with, as you said. What have you found tends to work and is a gracious way to not sound arrogant, but also just preserves your time when you have to?

A Yeah, it's always the ongoing struggle, and I heard this advice. I forget who said it, but it was this phrase that I really loved, and the I'm sorry, I can't right now, and I love it because it's super direct, but you actually are sorry that you can't meet with this person, but also making it clear that your plate is completely full, and your job is to focus on these things right now. It doesn't mean that you're never going to be able to meet with this person, just that right now, it's just not possible, and so I use a variation of that when I respond, and I feel like it's not ever, you know, something I feel great about, but it's sort of, you know, that's what the situation is, and You know, you're at least expressing a little bit of remorse that you can't meet with everybody that you really would love to meet with. I used to have this whole, like, canned text thing. It's like this paragraph that was really descriptive, like, well, I'd love to meet with everyone who asks. I really can't because right now in the middle of all of that, I was like, I don't need to explain every single little thing. I just need to get across the fact that I really would love to, but just not able to right now.

AI assessment note: “it was this phrase that I really loved, and the I'm sorry, I can't right now”

Q more and more is almost the eradication of the friends and family, almost pre-seed round. I don't see sub-five hundred K rounds today. Really brilliant founders, especially, and I'm speaking purely from a London perspective, can go out and raise one and a half, two million with a PowerPoint if they're very clearly bright, have good pedigree. How do you think about this potential eradication of pre-seed? Would you agree?

A I don't think so. I think there's always going to be a place for pre-seed, especially for those founders, maybe first-time founders, maybe founders that are not found in the typical places. I think there is always going to be a place for very early stage rounds. We still see it from time to time. We don't see it as much as we used to. I think it's very important. I think it's an incredibly important funding mechanism to have. And I think if it does get eradicated, I think it's also going to eradicate sort of that category of founder, which we can't do. There are plenty, as you know, multi-billion dollar successes that were led by first-time founders, and sometimes they're not found in the typical places. And so I do think it's really important to have that full spectrum of sources of funding right from the early pre-seed stage all the way through.

AI assessment note: “I don't think so. I think there's always going to be a place for pre-seed”

Q more and more is almost the eradication of the friends and family, almost pre-seed round. I don't see sub-five hundred K rounds today. Really brilliant founders, especially, and I'm speaking purely from a London perspective, can go out and raise one and a half, two million with a PowerPoint if they're very clearly bright, have good pedigree. How do you think about this potential eradication of pre-seed? Would you agree?

A I don't think so. I think there's always going to be a place for pre-seed, especially for those founders, maybe first-time founders, maybe founders that are not found in the typical places. I think there is always going to be a place for very early stage rounds. We still see it from time to time. We don't see it as much as we used to. I think it's very important. I think it's an incredibly important funding mechanism to have. And I think if it does get eradicated, I think it's also going to eradicate sort of that category of founder, which we can't do. There are plenty, as you know, multi-billion dollar successes that were led by first-time founders, and sometimes they're not found in the typical places. And so I do think it's really important to have that full spectrum of sources of funding right from the early pre-seed stage all the way through.

AI assessment note: “I don't think so. I think there's always going to be a place for pre-seed”