The Exchanges

Q That's a tough meeting to come back to. I do want to ask you on the Scout program as well. Too interested here. How much do you give the Scouts? How do you think about tarry allocations for the Scouts? You know, we see it more and more, even in Europe now. How do you think about how you structure that Scout program?

A So in general, we want to continue to expand our network. And that's when I said earlier in this conversation that access is everything for VCs. And so we want to continue to spread out our network. We are, again, only five people, so how many people can we actually get to meet? Spread out the network, both in diversity and geographic location. And in order to do that, we need to invest in people who are themselves unique in the market. And so we have six Scouts. We have four in LA, one in Boston, and one in San Francisco. Three men, women, three men. Diverse as well. And we've given each one of them 250,000 dollars. They are to spend it in, um, unique opportunities which are B to B only. It has to be where we focus. These are investments we think we're actually going to make money on. Like, we hope that if all six of those fire starters make an investment, that's 30 investments over the next three years. If we can get three out of those 30 or two out of those companies where we end up leading the seed round and really doing a core investment check, and that company turns it, it was way worth it. Way worth it. Plus we're expanding and extending the bonfire brand by working with all these people. And we don't just give the money to scouts and say, call us later. We have monthly calls. We have monthly, we call them mastery series. So we might talk, Jim might give a presentation o…

AI assessment note: “we've given each one of them 250,000 dollars.”

Q one of the many reasons for my limited friendship group, is Portfolio construction. When we think about portfolio construction for you today, how do you think about this? You know, you're a storied venture investor. I'm sure you thought about this a lot with the hundred and one million dollars that you have in your new fund. Like what's the right number of lines and how do you approach it?

A Right. Look, we have made our bed. We said we are seed investors in B to B software and we're very good at it. We're getting better. We're always trying to get better, but we're not going to move out of that. So we have a very clear focus in what we do and we do about Seven to eight, seven to nine deals a year. We'll have a 24 to 28 company portfolio, and we do about 40% of the investments are the primary check and 60% follow-on. We have very methodical ways that we think about the follow-on and how much capital we're going to put into additional companies. But we stick to our knitting, and we're trying to get deeper and And not wider, if that makes sense. Look, we lucked out. We focused on Jim and I've been focused on for many years, the B to B cloud software, and that has turned out to be a pretty big business, but we want to stay focused there. And on the portfolio construction, we may dial up risk. Obviously we're monitoring the portfolio at all times. And we may dial up risk if the portfolio is kind of down the middle after, you know, maybe do three or four investments that are down the middle type of things that we like to do. We'll dial up risk for some opportunities that Maybe as a unique founder or some situation where there's not as much traction for us to make a decision.

AI assessment note: “We'll have a 24 to 28 company portfolio, and we do about 40%”

Q Can I ask, if you take it pre-board member status and actually pre-investment, I think another really interesting thing about the move from solo to partnership is Is that investment decision-making process? And I'm always fascinated by the consensus versus non-consensus. How do you think about, as Josh Kaufman said, finding the truth together? What does that process look like for you? And are you consensus or non-consensus driven?

A Well, we're consensus driven. Just as a reminder, Jim and I joined forces at the end of 2016. Brett joined us in 2018. Tyler joined us in 2019. Jen joined us last year. So we keep expanding this team that's a decision-making But in a very short period of time, like almost every year we're adding to that team. And so you're trying to welcome their thoughts, bring in their opinions, their expertise, and then apply that to a decision. When it was me, I just made a decision, right? And then it was Jim was on his own making decisions and it was the two of us. And so you can, you know how the math works here. And so we do have a consensus process because we're trying to make sure that everybody does the right amount of work, asks the right amount of questions or the right questions, for example, and And then presents it such that we all can make a decision. Now, when one of us says no, the deal can happen. When two of us says no, especially two of the partners, I mean, it's not going to happen, right? But what we've done in a couple different ways to manage some of that opportunity is we have implemented a small check program. So any one of the five of us can invest up to 500 grand in a company that we just absolutely believe in, whether it's the founder or the business, just absolutely believe in. And it may be not even a seed round. It's maybe a An angel round, maybe a million buck…

AI assessment note: “Well, we're consensus driven.”

Q one of the many reasons for my limited friendship group, is Portfolio construction. When we think about portfolio construction for you today, how do you think about this? You know, you're a storied venture investor. I'm sure you thought about this a lot with the hundred and one million dollars that you have in your new fund. Like what's the right number of lines and how do you approach it?

A Right. Look, we have made our bed. We said we are seed investors in B to B software and we're very good at it. We're getting better. We're always trying to get better, but we're not going to move out of that. So we have a very clear focus in what we do and we do about Seven to eight, seven to nine deals a year. We'll have a 24 to 28 company portfolio, and we do about 40% of the investments are the primary check and 60% follow-on. We have very methodical ways that we think about the follow-on and how much capital we're going to put into additional companies. But we stick to our knitting, and we're trying to get deeper and And not wider, if that makes sense. Look, we lucked out. We focused on Jim and I've been focused on for many years, the B to B cloud software, and that has turned out to be a pretty big business, but we want to stay focused there. And on the portfolio construction, we may dial up risk. Obviously we're monitoring the portfolio at all times. And we may dial up risk if the portfolio is kind of down the middle after, you know, maybe do three or four investments that are down the middle type of things that we like to do. We'll dial up risk for some opportunities that Maybe as a unique founder or some situation where there's not as much traction for us to make a decision.

AI assessment note: “We'll have a 24 to 28 company portfolio, and we do about 40%”

Q Can I ask, if you take it pre-board member status and actually pre-investment, I think another really interesting thing about the move from solo to partnership is Is that investment decision-making process? And I'm always fascinated by the consensus versus non-consensus. How do you think about, as Josh Kaufman said, finding the truth together? What does that process look like for you? And are you consensus or non-consensus driven?

A Well, we're consensus driven. Just as a reminder, Jim and I joined forces at the end of 2016. Brett joined us in 2018. Tyler joined us in 2019. Jen joined us last year. So we keep expanding this team that's a decision-making But in a very short period of time, like almost every year we're adding to that team. And so you're trying to welcome their thoughts, bring in their opinions, their expertise, and then apply that to a decision. When it was me, I just made a decision, right? And then it was Jim was on his own making decisions and it was the two of us. And so you can, you know how the math works here. And so we do have a consensus process because we're trying to make sure that everybody does the right amount of work, asks the right amount of questions or the right questions, for example, and And then presents it such that we all can make a decision. Now, when one of us says no, the deal can happen. When two of us says no, especially two of the partners, I mean, it's not going to happen, right? But what we've done in a couple different ways to manage some of that opportunity is we have implemented a small check program. So any one of the five of us can invest up to 500 grand in a company that we just absolutely believe in, whether it's the founder or the business, just absolutely believe in. And it may be not even a seed round. It's maybe a An angel round, maybe a million buck…

AI assessment note: “Well, we're consensus driven.”

Q You mentioned that kind of ramping the learning curve, and final one, but, you know, we chatted before about information overload, especially with regards to the decision-making process. When we chatted before about this information overload, what did you mean by this, and how does it impact your process?

A Look, I have two teenagers, right? So I get the iPhone. I've benefited from the iPhone. But in the last two years, I've gotten off of Snap. I'm off of Insta. I've never been on Facebook. I spend maybe 10 minutes a month on Twitter. But, I mean, I'm still inundated with what I call my slop. I call it slop, right? So this is text, email, Slack, Telegram, WhatsApp, LinkedIn, Signal, the phone, my family, my in-laws. It's a bunch of slop, and it never ends. And so in order to manage all that information flow, I try to continue to get a handle around it so that I can pull out the information that's important. Otherwise, I'm just kind of inundated. And, you know, the more information we have, in some ways, the harder it is to make a decision. I have found at Double M and Bonfire, when we spend a lot of time over time making, you know, trying to almost in reverse justify the decision we're about to make, those companies ended up not being the big winners. The ones where you come in and like, we got to do this deal. That founder is unbelievable. This opportunity is so cool. We got to do it. Those tend to be the winners, you know, so the more analysis paralysis you go through, sometimes it backfires.

AI assessment note: “the more information we have, in some ways, the harder it is to make a decision.”

Q Another big transition that you made is also moving from the solo VC and investor that you were with Double M to now the partnership that you have today with Bonfire. I'd love to hear, like, what are the main takeaways for you when comparing the life of the solo versus the partnership mentality? And how do you think about that comparison?

A Well, obviously, there's positive and negatives. The positives outweigh the negatives. I mean, look, I came from a partnership mentality. I understand and understood what were the benefits from being in that partnership. Really, the hardest thing to do is scale yourself and scale an individual. And so, me going from sole GP, sitting in my office, perhaps being lonely, looking at deals, trying to get things done, to now we have a five-person investment team and a I mean, that just has introduced me to such a larger brain trust, right? Such a larger amount of deal flow. Imagine how many good deals that I may have turned down as a sole GP because I had limited knowledge of the space, or frankly, limited time. And now I have exponentially grown our networks, our deal flow, our knowledge with the team. And you know, access is key in venture. So I think that the, for sure, the positives have outweighed the negatives. One thing that we need to be careful of, and I try to push this a little bit, is still being nimble. I can give you examples. When I first met Walter Driver from Scopely or Jeff Green from the Trade Desk, I invested in the first meeting. I committed to them in that first meeting. We don't do that anymore. It's really hard, right? And especially since I have a team, I can't just walk in and go, yeah, we're going to invest in this company. We need to really talk about it, …

AI assessment note: “Really, the hardest thing to do is scale yourself and scale an individual.”

Q Another big transition that you made is also moving from the solo VC and investor that you were with Double M to now the partnership that you have today with Bonfire. I'd love to hear, like, what are the main takeaways for you when comparing the life of the solo versus the partnership mentality? And how do you think about that comparison?

A Well, obviously, there's positive and negatives. The positives outweigh the negatives. I mean, look, I came from a partnership mentality. I understand and understood what were the benefits from being in that partnership. Really, the hardest thing to do is scale yourself and scale an individual. And so, me going from sole GP, sitting in my office, perhaps being lonely, looking at deals, trying to get things done, to now we have a five-person investment team and a I mean, that just has introduced me to such a larger brain trust, right? Such a larger amount of deal flow. Imagine how many good deals that I may have turned down as a sole GP because I had limited knowledge of the space, or frankly, limited time. And now I have exponentially grown our networks, our deal flow, our knowledge with the team. And you know, access is key in venture. So I think that the, for sure, the positives have outweighed the negatives. One thing that we need to be careful of, and I try to push this a little bit, is still being nimble. I can give you examples. When I first met Walter Driver from Scopely or Jeff Green from the Trade Desk, I invested in the first meeting. I committed to them in that first meeting. We don't do that anymore. It's really hard, right? And especially since I have a team, I can't just walk in and go, yeah, we're going to invest in this company. We need to really talk about it, …

AI assessment note: “positives outweigh the negatives. I mean, look, I came from a partnership mentality.”

Q years ago, 20% ownership was pretty feasible and possible. Now I think it's a lot more challenging. How do you think about the centrality of ownership today when you're making a decision? And this is where I've made big mistakes, honestly, Mark. I've said no because it was eight percent, and I wanted 13 or 14, and it was Huge mistakes. How do you think about the centrality of ownership?

A Right. So we focus on it. I heard you with David Tish the other day. I mean, everybody has their opinions, and I think they're all valid. Depends on what you believe and what your fund is set up to do. We invest in the seed, as I keep saying, and we really like to take ownership in the seed because we understand and believe we'll be diluted over time. We like to take as much ownership in the seed. We almost double down because of the amount of capital we put in, not necessarily the ownership, but we'll maintain our pro rata in the A round. We might do a little bit in the B, and then we're done. And so we believe that if we are going to be the type of investors we are, which is we get very involved with our companies. We spend time. We want to be the first call you make for bad news and good news. If we're going to be putting all that work into these companies, we want to have ownership, and such that when this company takes off or has an exit, that we've actually been rewarded for both the time we put in and the capital we put in.

AI assessment note: “we really like to take ownership in the seed”

Q Now, I have to ask you, and it's not on the schedule, but you know, you mentioned Bill Daniels and that incredible career and the many different routes that he took. From working alongside him and being around him, were there some big takeaways from you in terms of how he impacted your mindset and how he got engaging?

A Yeah, and his right hand person is a man by the name of Brian Devey, who was much younger than Bill and is an LP in all my funds and has been my, one of my mentors forever. They just, the way they dealt with people was straight up. You told people what you thought. You helped people do what they wanted to do. You lived by a handshake. And those were things that sound very trite, but are super important today still. I think that everybody knows when I'm having a conversation with them, I'm telling you the straight up story. And that's really one of the things I learned. Of course, I learned that from my father as well, but seeing that in a business setting and how you worked with and dealt with people was very impactful for me.

AI assessment note: “the way they dealt with people was straight up.”

Q And it goes to my next question, which is actually Time allocation, which is something I struggle with a lot, which is like, how do you think about time allocation across the portfolio? Like rational minds would say, spend it with the winners. That's where all your dollars will be returned. But actually it's not always that simple. How do you think about like effective time allocation across the portfolio?

A I'm obsessed with time management myself. The reality is, and you've heard this before, sometimes the winners need you the least. And it just goes that way. Like you would love to say, look, I'm on the board of these three companies. They're going to the moon. And I'm just hanging out and getting the accolades because I happen to be on the board of this company that's going to the moon. No, what you end up having is that the companies that are struggling need us the most because that's how we put ourselves out there. We have a lot of experience. We've seen a lot of things. We actually are telling you when we're investing, we will be there when you need us. And that is the hard part because we promise it. And then it takes away from the time that we need to maybe focus on winners or new investments, but it's okay. It's the life we made for ourselves and we really enjoy it.

AI assessment note: “the companies that are struggling need us the most”

Q Now, I have to ask you, and it's not on the schedule, but you know, you mentioned Bill Daniels and that incredible career and the many different routes that he took. From working alongside him and being around him, were there some big takeaways from you in terms of how he impacted your mindset and how he got engaging?

A Yeah, and his right hand person is a man by the name of Brian Devey, who was much younger than Bill and is an LP in all my funds and has been my, one of my mentors forever. They just, the way they dealt with people was straight up. You told people what you thought. You helped people do what they wanted to do. You lived by a handshake. And those were things that sound very trite, but are super important today still. I think that everybody knows when I'm having a conversation with them, I'm telling you the straight up story. And that's really one of the things I learned. Of course, I learned that from my father as well, but seeing that in a business setting and how you worked with and dealt with people was very impactful for me.

AI assessment note: “the way they dealt with people was straight up. You told people what you thought.”

Q years ago, 20% ownership was pretty feasible and possible. Now I think it's a lot more challenging. How do you think about the centrality of ownership today when you're making a decision? And this is where I've made big mistakes, honestly, Mark. I've said no because it was eight percent, and I wanted 13 or 14, and it was Huge mistakes. How do you think about the centrality of ownership?

A Right. So we focus on it. I heard you with David Tish the other day. I mean, everybody has their opinions, and I think they're all valid. Depends on what you believe and what your fund is set up to do. We invest in the seed, as I keep saying, and we really like to take ownership in the seed because we understand and believe we'll be diluted over time. We like to take as much ownership in the seed. We almost double down because of the amount of capital we put in, not necessarily the ownership, but we'll maintain our pro rata in the A round. We might do a little bit in the B, and then we're done. And so we believe that if we are going to be the type of investors we are, which is we get very involved with our companies. We spend time. We want to be the first call you make for bad news and good news. If we're going to be putting all that work into these companies, we want to have ownership, and such that when this company takes off or has an exit, that we've actually been rewarded for both the time we put in and the capital we put in.

AI assessment note: “we really like to take ownership in the seed because we understand and believe we'll be diluted”

Q And it goes to my next question, which is actually Time allocation, which is something I struggle with a lot, which is like, how do you think about time allocation across the portfolio? Like rational minds would say, spend it with the winners. That's where all your dollars will be returned. But actually it's not always that simple. How do you think about like effective time allocation across the portfolio?

A I'm obsessed with time management myself. The reality is, and you've heard this before, sometimes the winners need you the least. And it just goes that way. Like you would love to say, look, I'm on the board of these three companies. They're going to the moon. And I'm just hanging out and getting the accolades because I happen to be on the board of this company that's going to the moon. No, what you end up having is that the companies that are struggling need us the most because that's how we put ourselves out there. We have a lot of experience. We've seen a lot of things. We actually are telling you when we're investing, we will be there when you need us. And that is the hard part because we promise it. And then it takes away from the time that we need to maybe focus on winners or new investments, but it's okay. It's the life we made for ourselves and we really enjoy it.

AI assessment note: “the companies that are struggling need us the most because that's how we put ourselves out there.”

Q Final one. What's the most recent publicly announced investment? And why did you say yes and get so excited, Mark?

A Well, I think you saw recently, it's a company called Copia. Jen and Brett led that. Jen was very passionate about the business. We ended up using them. I don't know if you've seen it kind of entering into the metaverse here for business. We used it for a event that we did with a bunch of bonfire founders. And it's really cool and different in terms of how you interact with The team, instead of just using a Zoom, this is your own world that you can make. We can make a bonfire world. So it's very different than you'd ever think that we would do maybe as a bonfire firm, but it is software. It is cloud. And we were there early. We started to get to know the founding team. And as you see, um, Alexis Sohanian from seven, seven, six did the deal with us. And he was there early too. We both saw and believed that being a partner in that deal would be great for each other in the firm. I mean, the fund, I mean, excuse me, the company.

AI assessment note: “it's a company called Copia. Jen and Brett led that.”

Q Can I ask you a hard one? And it's, I asked David Tisch this at Box, and I said, if you were to think about your biggest miss, what would your biggest miss be? And I guess, what were the tangible takeaways that changed how you think about investing because of that miss?

A Yeah, I can give you two quick examples because they're related to what I just said about the individuals that I met in one meeting and invested. I met Sean Radd from Tinder, and I met the guys from Honey. And I turned down honey twice. And actually, I go back to the email exchanges I had with them. And I actually turned them down, as I said in the email, because I didn't have the time. That's a terrible answer, right? A terrible answer. And I think it was more, maybe I just didn't understand the business as well. And so there's going to be those types of situations. And I think that the learning is that as I get deeper into our investment career, both at Broadfire and Double M as a professional VC, I guess, Maybe professional's not the right word, but you still end up investing, and we invest in the seed stage. We're really investing in the founder, and the person, and the team, and we need to be, I just need to continue to be, to get conviction on those types of feelings when I have with a founder.

AI assessment note: “I met Sean Radd from Tinder, and I met the guys from Honey.”

Q Final one, and it's just like, as we said, going back to the preemptive rounds, with them coming faster, you have to make the decision on whether to double down sooner. What does that reinvestment decision-making process look like, and how do you think about when to double down versus when not to?

A Yeah, well, we, of course, take a fresh look at the company, but we also have the most information on that company. We do about seven to 10 deals a year. We will take seven board seats of those 10, right? We're involved with these companies. We're seeing the information flow. So we should have the best feel and look at real information for how to make that investment. And if we're seeing poor traction, they're not going to get these types of rounds that are getting done. Right now, we are sticking to our process of investing in few deals. We have high conviction on these deals, but the rounds are coming faster. And they're coming bigger. And so we're seeing an investment period compressed, right? It's not necessarily we're going to go out and raise a fund sooner, but we're seeing the investment dollars go out in a quicker way because they're bigger rounds and because we're doubling down and we're seeing fantastic growth in some of our portfolio companies. So we're making the decisions on how to invest based on really what they have been able to achieve in comparison to many other metrics and seed companies that we've already invested. And so we can see who is going to be an outlier a little bit quicker than most because we're so involved with the company. We tried to make that investment decision. There are situations, of course, where we are extending capital. We'll call it an…

AI assessment note: “making the decisions on how to invest based on really what they have been able to achieve”

Q about the 500 K check program, Love that. Concern I always have with these programs is when you kind of minimize that barrier to investing, it kind of allows for someone to go, ah, great founder, big market, ah, let's see. How do you ensure you still retain that high, high bar without losing that quality? Do you see what I mean? And without kind of ending up with that?

A Well, you can only do one or two, right? And they are being watched. So in fairness, you have a lot of almost, I wouldn't call it this way, but there is peer pressure to make sure that these Two small checks you make over a three-year period are ones that are going to be really good companies that you just feel like, you know, a little bit more or get a situation where there's new. Look, we have two young members of the team who have a lot of different relationships, a lot of different experiences with technology that's different than mine. So when they come to me and say, this is a really cool technology that a lot of people are using and I don't understand it, I have to be careful and say, well, I would never use that. So why are we investing? I can't, I don't do that. We can't do that. If Jen wants to do an investment she really thinks isn't passionate about, she should have the chance to do that. But there is a bar, right? You definitely don't want to come back at the end of three years, and you made three small-check investments, and they all turned to zero.

AI assessment note: “Well, you can only do one or two, right? And they are being watched.”

Q I do want to start, though. I love a bit of context. So tell me, how did you make your way into the world of venture, and how did you come to co-found Bonfire over the last few years? I think it was four years ago or so.

A Well, really, I, when I came out of college, I was already getting into finance. I worked for a bank, and then I became an investment banker. More like a merchant banker because we also made investments for a very famous entrepreneur. His name was Bill Daniels and is currently still known as the father of cable TV in the US. I got a chance to work for him and ended up working for the firm for 20 years. He was one of those stories you don't hear about anymore. Didn't finish high school. Lied to get into the Navy. Golden Glove boxing champion for two years. Flew 250 missions as a fighter pilot. Came back to the US. Started selling insurance. Wanted to see a boxing match on closed circuit TV and started Cable television in 1953. This is the kind of person I got to work under, and all the people that worked for him, and so we had an investment bank, about 75 people that did M&A in the cable world, and ISPs, and towers, and broadband, wireless, et cetera, across the world, as well as we owned a bunch of different companies. I ran international, so I got a chance to live in both Paris and London, and so for many years, that's what I did, and we also invested in companies ourselves, as well as other funds. And so when we sold the firm, we sold all the assets upon his death in 2002 1001. Then we had still the investment bank, and we sold the investment bank in January, 2007 to RBC Capi…

AI assessment note: “that's really the taste of investing and where I got the taste of investing from.”

Q Can I ask, how do you think about preventing board meetings being a reporting function? How do I stop that and go, let's talk about strategic decisions and the core problems that we're facing?

A Well, you hear this from the really great investors. For example, Fred Wilson, for example. You know, the board meeting is for some reporting, but it really is to talk about strategy and making decisions, and so all that perfunctory reporting should have been discussed and evaluated and reviewed prior to the meeting. Every board meeting I have, when I get the deck or get the information, by the way, we're talking to these founders all the time, so it's not like we wake up the week before each quarter and start having a conversation with the founder for the first time, and I like to make sure, and I go through the details with that founder so that we're not I'm actually not the one doing it on the board meeting. I do try to push because I can do that in my position now. I do try to push other board members to be that same way. I'm like, please talk to the founder about any detailed questions you have in terms of numbers or the funnel or the hiring process we're doing. Please try to get that over with so that we can really help the founders or the team or meet more of the team in the board meeting instead of just waiting for the CEO to tell us what to do. Let's do that before the meeting. And when we get to the meeting, let's really focus. I'm maniacal about trying to get board decks shortened. Right. We have a template here at Bonfire, which we give to all our founders. They've …

AI assessment note: “all that perfunctory reporting should have been discussed and evaluated and reviewed prior to the meeting”

Q a more kind of firm-wide perspective, but it's the element of boards. You said there about kind of maybe taking seven, eight out of 10 of the investments as board sees. How has your board member style changed over the years? You've been a board member on many companies for many years. How has your style changed, and what do you think were those, like, inflection points in them changing?

A Well, my style has changed. I mean, I'm on the board of one big public company. It's a ten billion revenue company with five billion of EBITDA, and I'm about to join another public company. And then I have my seed investments. So one day I'll be having a conversation with the founder about helping her win a 50,000 dollar ACV contract or hiring her head of marketing, right? And the next day I'm talking about a two and a half billion dollar financing with my company, and I'm the chairman of the audit committee on these public companies. So I have these serious conversations. They're all serious, but they're just serious in different levels. And as a board member, I have luckily lived in several countries and I've worked on deals in 30 countries, many, many different entrepreneurs. I've learned how to work with and advise lots of different types of entrepreneurs, and so I tend to be, you know, we've heard this before, I'm the psychiatrist, right? Like, I know when to motivate you, I know when to challenge you, I know when to comfort you, and so I've really dug deeper into that as a board member, as opposed to a board member that comes in and kind of whips through and wants to talk about, you know, your, of course I talk about funnels, I talk about all this stuff, but I want to talk about really Strategy and how to make you a better person, or not a better person, but how I can hel…

AI assessment note: “when I was younger coming into boards, it was more like going through the board deck”

Q that founder centricity and the relationship with them, my concern is today that With the liquid markets that we have and the proliferation of capital that we have, you don't have the time on the fundraisers themselves, and bluntly, you just have to make decisions faster than ever before. How do you balance that centricity of founder relationship with the need to make decisions very, very fast in these markets?

A Well, we're all in the same boat, so we talk a lot about this, the need to move. It's been fun to find a situation where we all have this feeling around the founding team. We gotta move fast. We have done a meeting to term sheet In nine days, which is now apparently a little bit long, I'm hearing things are happening over the weekend, but nine days is a big move for somebody investing in a seed company. You know, we can talk about the Tigers and D ones and all those guys. They're doing great. Fine. They're looking at companies that have quite a bit more traction and things happening so they can make those decisions faster. We still need to go back. We're trying to understand how big the market is. There's very little traction with these companies. We're trying to understand that founding team. And in order to understand that funny team, you need to do those types of references. You need to have the conversation with people around them. And the other side of the coin, which is very hard, I think, for all of us, is the expectations for these founders now. They can do 20 Zoom meetings in a week, and they want a decision faster, and so we're all dealing with that and learning to move faster, and we'll see how it plays out.

AI assessment note: “we're all dealing with that and learning to move faster”

Q a more kind of firm-wide perspective, but it's the element of boards. You said there about kind of maybe taking seven, eight out of 10 of the investments as board sees. How has your board member style changed over the years? You've been a board member on many companies for many years. How has your style changed, and what do you think were those, like, inflection points in them changing?

A Well, my style has changed. I mean, I'm on the board of one big public company. It's a ten billion revenue company with five billion of EBITDA, and I'm about to join another public company. And then I have my seed investments. So one day I'll be having a conversation with the founder about helping her win a 50,000 dollar ACV contract or hiring her head of marketing, right? And the next day I'm talking about a two and a half billion dollar financing with my company, and I'm the chairman of the audit committee on these public companies. So I have these serious conversations. They're all serious, but they're just serious in different levels. And as a board member, I have luckily lived in several countries and I've worked on deals in 30 countries, many, many different entrepreneurs. I've learned how to work with and advise lots of different types of entrepreneurs, and so I tend to be, you know, we've heard this before, I'm the psychiatrist, right? Like, I know when to motivate you, I know when to challenge you, I know when to comfort you, and so I've really dug deeper into that as a board member, as opposed to a board member that comes in and kind of whips through and wants to talk about, you know, your, of course I talk about funnels, I talk about all this stuff, but I want to talk about really Strategy and how to make you a better person, or not a better person, but how I can hel…

AI assessment note: “when I was younger coming into boards, it was more like going through the board deck”

Q some respects. And I'm not sure if that Makes the firm more successful or less successful, because it, it almost allows you to see the upside beauty in a lot of things, and it loses that downside protection fear, but it also lowers the bar in some respects. What are your experiences on this, having had winners very early in portfolios, and then deploying the rest of them in tandem?

A Well, one thing, early on, the companies you think are going to be super winners sometimes don't become ones, and ones you think are dogs become great winners, and so that's just life, right? And you have to be careful not to overemphasize the winners in the early couple of years and underemphasize the ones who are not performing. And so we need to keep kind of a clear head about that. I've had a conversation with another VC who said, well, the rest of our portfolio is just killing it. So we think we're just going to throw in, you know, we're going to just leave this deal and throw in three and a half million bucks. I think that's what you're referring to here. He's like, you kind of, well, we're going to make so much money on the rest of the portfolio. Let's just throw in money here. I don't think many people do that. We can't do that. We have a, um, like I said, a team that kind of keeps each other true, but I get it. If your portfolio is doing really well, what if your portfolio is doing really poorly early on? What does that make you feel like, are you going to be riskier on the next investment or less risky? Are you more worried about your portfolio? I'm not going to do it. We're not going to do any more deals because, uh, the rest of this portfolio is in trouble.

AI assessment note: “We can't do that. We have a team that kind of keeps each other true”

Q But the hard thing also for me is like, bluntly, you have to proactively forecast your reserves deployment before you've even allocated those additional lines in the portfolio. Often, you know, the best companies come back faster. And so you've got to essentially project out on the complete unknown lines in the portfolio and you'll double down on them. How do you think about that challenge?

A Uh, you just keep adjusting the model. You know, you're watching the model and adjusting it. One thing I want to say as well is One of the reasons that it was important to commit to doing your pro rata was there was this thing called signaling risk, which people were worried about. And that still is relevant today, but less relevant. So using my example, the A investor comes in, they're putting in 19 of a 20, 18 of a twenty million dollar round. They want to take as much ownership. They don't care about signaling. It's not a signaling issue that we're not going to put as much pro rata in. They're actually like happy we're not putting as much pro rata in. I think the companies that are struggling, you have to put in more money and there's a signaling risk. That may be a little bit of a canary in the coal mine saying that that company's really not on the right track.

AI assessment note: “you just keep adjusting the model. One thing I want to say as well is”

Q I do want to start, though. I love a bit of context. So tell me, how did you make your way into the world of venture, and how did you come to co-found Bonfire over the last few years? I think it was four years ago or so.

A Well, really, I, when I came out of college, I was already getting into finance. I worked for a bank, and then I became an investment banker. More like a merchant banker because we also made investments for a very famous entrepreneur. His name was Bill Daniels and is currently still known as the father of cable TV in the US. I got a chance to work for him and ended up working for the firm for 20 years. He was one of those stories you don't hear about anymore. Didn't finish high school. Lied to get into the Navy. Golden Glove boxing champion for two years. Flew 250 missions as a fighter pilot. Came back to the US. Started selling insurance. Wanted to see a boxing match on closed circuit TV and started Cable television in 1953. This is the kind of person I got to work under, and all the people that worked for him, and so we had an investment bank, about 75 people that did M&A in the cable world, and ISPs, and towers, and broadband, wireless, et cetera, across the world, as well as we owned a bunch of different companies. I ran international, so I got a chance to live in both Paris and London, and so for many years, that's what I did, and we also invested in companies ourselves, as well as other funds. And so when we sold the firm, we sold all the assets upon his death in 2002 1001. Then we had still the investment bank, and we sold the investment bank in January, 2007 to RBC Capi…

AI assessment note: “that's really the taste of investing and where I got the taste of investing from.”

Q The final one I do have to ask, you know, before the quickfire, you've also invested in, you know, many funds, I think it's 16 or 17 now. How did fund investing change how you also think about direct investing? Because it's such a unique hat to actually have both on at the same time.

A Yeah, I mean, we, we, I've been lucky to invest in a couple of funds that do things very differently than what I've ever done or they do. For example, they might focus on consumer, or BAM Ventures, or Maven Ventures, or Halogen, and Mac Capital, for example, doing, having access to different types of deals that I would ever see, and getting expertise and information flow from them is helpful for what we do. I'm not taking their information and using it, I'm just saying it keeps me abreast of what's happening in the market. But, you know, I've had my first investment as an angel, which was never called that, as you know, until later on in life, was in And they needed 10,000 dollars for a server to start their ISP, right? The web hosting company. And I gave them the 10,000, and then they paid me 15% interest plus warrants. So I got the 10,000 dollars back, and then the warrants, and then they went public, and I made forty-x on the warrants. By the way, 2500 dollar investment. So I had the bug. Now, of course, I lost money going forward, but I had the bug. And then I started to invest in other companies that were our clients, and then we as a firm were investing in other funds, and And it just gave me a real good feeling for how to manage and become a professional investor, which is where we are now.

AI assessment note: “getting expertise and information flow from them is helpful for what we do”

Q But the hard thing also for me is like, bluntly, you have to proactively forecast your reserves deployment before you've even allocated those additional lines in the portfolio. Often, you know, the best companies come back faster. And so you've got to essentially project out on the complete unknown lines in the portfolio and you'll double down on them. How do you think about that challenge?

A Uh, you just keep adjusting the model. You know, you're watching the model and adjusting it. One thing I want to say as well is One of the reasons that it was important to commit to doing your pro rata was there was this thing called signaling risk, which people were worried about. And that still is relevant today, but less relevant. So using my example, the A investor comes in, they're putting in 19 of a 20, 18 of a twenty million dollar round. They want to take as much ownership. They don't care about signaling. It's not a signaling issue that we're not going to put as much pro rata in. They're actually like happy we're not putting as much pro rata in. I think the companies that are struggling, you have to put in more money and there's a signaling risk. That may be a little bit of a canary in the coal mine saying that that company's really not on the right track.

AI assessment note: “One thing I want to say as well is One of the reasons”