The Exchanges

Q Or they become CEO because they're brilliant storytellers and they can inspire, and they see that a lot too. I think you're like Kit Bodnar at HubSpot. This guy's a born CEO. Like, I want to fund his company. Sadly, he's CMO of HubSpot, but, uh, I totally agree with you there. Um, tell me, why shouldn't you pay PR firms or consultants as you get going?

A I think it's one of those things that you just need to in-house. Ultimately, uh, every industry is going to be bespoke. Uh, in terms of your ability to get out there, get reach, get message, and, uh, paying a PR firm to go about doing it. One, they're gonna have a whole bunch of clients that they're, they're horse trading on who goes where. And two, over time, it's gonna benefit you much more to build these, uh, longstanding relationships with the reporters that are on your beat and give you an opportunity to tell your story yourself early on. And you know what? It probably is going to mean that people don't really care initially when you're telling your story, but at least you're going about figuring out one, who the people are that care about your industry to what message even kind of resonates. And it gives you a much quicker iterative feedback loop where I see oftentimes early stage founders think about the PR side of things and they just dump it over the line and give it to the PR agency. The PR agency goes out, runs around, does a bunch of stuff they don't really have visibility into. Then they come back and say, oh, sorry, it didn't really work out. And there's no iterative cycle or relationship development that's been built at all in that, in that funnel. And so even if it doesn't work, you're much better in-housing it than, than throwing it over to someone else and hav…

AI assessment note: “One, they're gonna have a whole bunch of clients that they're, they're horse trading”

Q I totally agree with you. Uh, tell me, what's the hardest element of your role with Redpoint?

A I think right now it's, uh, it's just managing the, uh, the market that we're in today and trying to figure out, um, where the best investment opportunities exist and what valuations ultimately are going to be worth in the end state and making sure we're picking correct between the difference between the A businesses and the A plus companies. Uh, that requires a level of discipline. Uh, it requires a level of, uh, ability to win. It requires a level of patience, uh, in making sure that we're holding the bar really high and willing to say no to stuff. And so that in this market right now where things have, have ground fairly to a halt at at least the stages we play in in series B and C, it just requires a lot of patience and a lot of willingness to not have FOMO, not feel like we're missing out on opportunities, and instead we're going to wait for the great ones to, to come across our desk.

AI assessment note: “managing the, uh, the market that we're in today and trying to figure out”

Q What crossover fund have you been most impressed by?

A Um, oh, well, I guess, I guess the, if I were to say pure crossover fund, I've, uh, I've really, uh, admired what, uh, the folks at KOTU have done in terms of building their brand and awareness at the, uh, the late stage growth market. I think that they've done a lot of, a lot of amazing stuff. I think in pure growth, uh, I, I just have infinite amounts of respect for, uh, Sequoia's growth fund, the folks over at Meritech and the guys over at Iconic. Uh, I think that all those groups do a really good job picking and, um, I, I, I want to beat all of them every single day and I wish them very poorly, but, uh, I have a lot of respect for what they're doing and a lot of friends at those places. And so, uh, I know when we're going head to head in an opportunity, you can't go wrong if, if a founder picks to work with them and, and they all do a very good job of picking, uh, to be in great companies. And so I, a lot of respect For the, for the game on the field, we play against all those firms.

AI assessment note: “if I were to say pure crossover fund, I've, uh, I've really, uh, admired what, uh, the folks at KOTU”

Q And then you recently tweeted the Andy Grove statement, only the paranoid survive. And I'm interested, how do you address the issue then of FOMO as a new investor?

A Yeah, totally. Uh, well, I think the way we think about it is at the end of the day, 2000 companies in a given year, uh, will get funded from venture investors and 200 of those will probably be done by, uh, firms that, that We would consider peers of ours and quality, um, investors. And, uh, at the end of the day, 10, 10 of those will drive something like 97% of the return for that vintage year. Uh, I'm always worried that there's a deal going on that we're not going to be a part of that's going to drive a ton of, uh, a ton of returns for, uh, for their investor base. And so it's one of the things that, uh, if you're not, if you're not worried about someone, uh, beating you and getting to something earlier than I think You're, uh, you're probably slipping and falling off your game. So it's certainly something that I think about all the time and always trying to find the best companies out there in the ecosystem.

AI assessment note: “I'm always worried that there's a deal going on that we're not going to”

Q at the end of the day, they're building brands to a large extent to get Deal flow, and to be kind of recognized within a space as a leader, which then gets deal flow. So, so I'm intrigued as, you know, that's one method of deal sourcing. What's your method of deal sourcing? We've heard the likes of Paige Craig say he's a hunter. How would you describe your methods?

A Yeah, uh, no, that's, that's a great question, and I, I think as you build a brand, uh, the ability for inbound flow, uh, to come about is, uh, is only enhanced, but I certainly don't think I'm smart enough to think in a vacuum of what's going on in, in a bunch of different markets, and, uh, and then try to go out and proactively work with people to create opportunities, or create businesses, or anything like that, so from a, A deal flow perspective, you know, there's certain things that I look for in businesses, ah, but it is very much networking and outbound kind of oriented where I'm as thoughtful as I possibly can be in approaching the entrepreneurs and coming in, uh, from either referrals or introductions, uh, from people that I know, but as it, if there's an interesting company that I don't know, I'm more than willing to send the CEO an email and say the, these are the three reasons that I find it interesting. We'd love to talk to you. Um, and I think that that ultimately, uh, is, is much a part in the way that I find deals as anything else.

AI assessment note: “it is very much networking and outbound kind of oriented”

Q And then what's your view on the kind of juxtaposition in VC branding between the branding of yourself as a VC investor, you know, Logan Bartlett, uh, Versus branding battery. You know, there's, there's some rockstar marketer VCs, you know, Mark Soosters, uh, who are upfront in many ways, just from their marketing perspective plays alone. So how do you view that juxtaposition between branding the VC and branding yourself?

A Yeah. Well, I, I will say, uh, it's, for the first time, it seems like there is more celebrity, uh, there are celebrity VCs, uh, to some extent, where the personality is first and foremost, and then the investment is secondary to that. We'll always be, or I'll certainly always be much more focused on the investment side of it, uh, and actually building value and working with the companies and all of those things. And so, I sort of view the, the branding aspect of it as a means to, uh, have people kind of self-select into the right person to work with and the right partner that they want to have for their business. But it's not a means to an end in and of itself. And I will say, you know, coming over to battery, I, uh, you sort of have a brand associated with the entity itself. And so when I was coming from a boutique merchant bank, boutique, no one's heard of you. Merchant bank. Uh, no one really wants to talk to you to, uh, I get the battery and now I'm smarter, I'm funnier, uh, and people want to talk to me a lot more. So it, you know, just being authentic to, to your own voice, I think is probably what's most important. Um, and if that happens to line up with the, the firm itself, then that's great. Uh, but if not, you know, you need to be true to who you are.

AI assessment note: “just being authentic to, to your own voice, I think is probably what's most important.”

Q And talking kind of outbound, I'm really intrigued to see your thought process on, on how you approach new and potential markets. So, you know, you could look at Slack and see, uh, a massive rise in the potential of bots and Slack bots. Uh, so how do you approach new markets and kind of think about the strategic thinking that goes into opportunities in new markets?

A Yeah. So I think there's two components to that. One is kind of having predefined thesis around Things. And then the other one is discovering things that seem to be working and, uh, digging into the various aspects around a particular business that's working and understanding why it's working. And so I would say we do both. Um, we will look at, you know, SAS software and say, all right, well, a lot of these applications are going to need to be mobilized. What's enabling Uh, enterprise mobility. And if things do, uh, get turned into mobile applications, well then what does that mean from an analytics perspective? What does that mean from an end user perspective? And all of those things. So we do take kind of a top down approach in thinking about some of those things, but then oftentimes, uh, it really is monitoring who's getting traction and knowing what's going on in the ecosystem and figuring out what's resonating with the end customer. Cause ultimately, um, We're, you know, we can sit in our office and try to think about what's going to resonate to an individual customer themselves, but we're thinking about so many different markets, particularly when you start thinking about horizontal software versus vertical software and selling into all these nuanced verticals. It starts to become difficult for us to have any perspective on what's going to resonate in the trucking market,…

AI assessment note: “One is kind of having predefined thesis around Things. And then the other one is discovering”

Q And then what's the most recent investment, and why did you say yes?

A Yeah, so, uh, there's one that's not announced, but it's in the marketing space, and it's a Series C, and we, We spent time with these guys in their Series B, and ultimately weren't able to get there on terms, and over the course of the last 24 months, I think we probably talked to them every month at least, and we turned over literally every stone, talking to as many customers as we possibly could, as many competitors in the ecosystem, as many of the large players that kind of play in the same area that they do, and Uh, by the end of it, these guys were probably a little worn out with our exhausted diligence, but yeah, we're excited. You know, that, that's just getting to the starting line now for us. So now we need to, we'll go work with them to, uh, to build a longstanding company. So we're pretty excited about that, but we certainly did our work as they will, as they will fully tell you.

AI assessment note: “there's one that's not announced, but it's in the marketing space”

Q I do want to ask you, you said about price recalibration there. Honestly, I'm not seeing it at all. In seed and A, nothing's changed, because all of you guys, have cut and girls, have come down earlier, and so actually, you're almost seeing price inflation at the pre-seed and the seed with the migration of growth funds earlier. So help me out here. How are you seeing prices recalibrate?

A Yeah. Well, I think it's a funnel, right? It kind of goes to how public markets end up, uh, flowing through to private markets in general. And so obviously we've seen it in the public markets and the private markets, late stage privates right now, we're not seeing a ton of repricing, but we are seeing when, when they're making investments, it's typically converts into the IPO at some discount or something like that. We're seeing some like structured terms associated with it. Then there's this big gap where There aren't a ton of deals getting done right now. That's the Series C, Series D, maybe a little Series B stage. And so what you are seeing is there's a dearth of opportunities that even exist right now because those companies have raised so much capital and have such high post, uh, last money post round valuations that you're not seeing them go out there and fundraise right now. Instead, they're kind of waiting to grow through or wait for the market to normalize in some way. And so what does that mean? Well, You're seeing a bunch of people, uh, say, hey, well, we would have invested, I don't know, two hundred million dollars at a two billion dollar valuation. Well, instead, now we're going to invest twenty million dollars into 10 companies, right? And so take that same twenty million and invest it across the board. And so that's squeezing the earlier stage groups more and m…

AI assessment note: “it's pushing down into the seed, pre-seed part of the house”

Q Mark Suster at, um, up front. It's your Alexa Haney at seven, seven, six style, or it's your all in unison Sequoia. I think you could say benchmark. I mean, obviously Bill's got a bigger brand on social, but generally the brands are pretty heavy hitters all across, largely built through track. But I think it's like, it's idealistic to try and do both at once. Do you not think?

A Uh, I think it's idealistic to try to do both. At once in that, like inevitably you're going to be pulled in one direction or the other, right? And you can look at where people kind of pick one quick test of where people pick an orientation of individuals versus, uh, versus the firm is like, where do blogs reside, right? Do blogs reside on someone's own sub stack or someone's own domain, or do they reside on the firm's website or the firm's medium or the firm sub stack? And there's definitely Uh, gray areas that exist between the two, but ultimately I think there, there are some firms that have done a really good job of elevating the brand of individuals along with the brand of the firm. I think Andreessen's done a great job of this. Now, they, Andreessen Crypto, you don't think of as the same way of Andreessen Enterprise, right? You don't think Chris Dixon or Martine Cassato or David George in the same way that you do Marc Andreessen or Ben Horowitz or Jeff Jordan. And so, Maybe, maybe that's an exception to them, or maybe, um, there's something unique in the way that they've done that. But I think the way I think about it is how much accumulating benefit exists between the before the at sign and the after the at sign on the email address, right? And I just want to make sure that both of them mean something and that both of them mean more every day than it did before. And so L…

AI assessment note: “I think it's idealistic to try to do both. At once in that”

Q kind of the dearth of B's C's and D's because people are kind of retreating with their cash deposits. Um, are you advising founders now to not go out and raise? Because for me, I'm like, you cannot align your fundraise To macro markets, because six months time, it could be worse than it is now. 12 months could be even worse. If you need to raise, just fucking raise.

A Yeah, you know, right now is particularly weird, and I think it's most weird for those Series B folks, where to your point C, Series A, it's mostly business as usual. Maybe it's a little higher at the earlier stages, maybe it's a little lower at the Series A stages, but in those two buckets, I think it's, you know, game on, and ultimately people are investing. Series B is kind of the weird one, Series C maybe to a lesser extent, where, where there aren't a ton of data points out there in the market for what these, Businesses are worth, right? And so there aren't a lot of comps. There aren't a lot of people that are actively making the market for these potential investment opportunities. And so while I think that if you go out right now to raise, or if you went out two months ago to raise, you might ultimately get a far higher price than you would two months from now. Ultimately, the market was kind of reeling in such a way that there's people that are doing a bunch of different things. Some people are saying they're actively investing, but they're not, you know, they're kind of wasting your time. Some people are actively investing, but they're actively investing at, you know, 50% below what you think you're worth. And then there are some people that are saying, hey, the market was this a month ago. In my mind, it's still this today, right? And so I think what happened over the …

AI assessment note: “And so my only advice and potentially holding off, and I agree with you”

Q is technically, I think it was Brad Feld said on the show to hire and fire the CEO single job. Like when you think about your role as a board member, how do you view your role then? If you don't want to remove this, not want to, but if you're not willing to ever remove the, CEO. And how has it changed over time? You've changed. How's it changed?

A Yeah. Um, I, so I don't view, uh, the role, my role as a board member necessarily to hire and fire the CEO exclusively. Um, I, I think that, uh, that's certainly an element and can be a part of the job, but the very literal, if ever you're going to the votes, Uh, that, uh, are, hey, do you have the power to get something done with regard to removing the CEO barring something, uh, that is totally, uh, ethical or cataclysmic for the business? Um, I think if ever you're going to the votes and using your role as a board member to oust the CEO, something else is broken down along the way in the journey and the relationship you built with, with the founder and, and the rest of the board. Uh, so I don't know. I mean, Brad, Brad has done this a lot longer than I have, and, uh, I'm sure he's been in a lot more of these situations in which this has been totally necessary on behalf of either existing investors or on behalf of other, uh, employees at the business. Um, but that's, that's not how I wake up every day and thinking about my role. I view my role as being, earning the right, uh, to be a trusted confidant to the CEO and the executive team. And I, I very much, uh, view all those words as important, earning the right to be a confidant. And if, if part of that ultimately involves helping the individual to see that there might be a better path for the business going forward, for their…

AI assessment note: “I view my role as being, earning the right, uh, to be a trusted confidant”

Q which is a show where we study hyper growth companies. Is that you always underestimate how big your winners will be consistently across all of them. Twilio. Great example. Would anyone put Twilio anywhere near it is today? Never. And so you always are led to say no by outcome scenario plans, I find, uh, and underestimate them. So why do you still do them? And is it not dangerous?

A Yeah, no, I, I definitely think it, uh, it can be dangerous. At the end of the day, there's only a single outcome, right? And what is it? Annie Dukes in her book, Thinking in Bets calls it resulting when you end up looking back based on the result and having that inform the decision. I ultimately think, um, in terms of the probability weighting, uh, I, I think that there is no certainty by which we, uh, I can make decisions. I don't know for other people, but, uh, ultimately I, I sort of view that there's a, uh, there's a spectrum of potential outcomes that can exist, uh, in, in some world in the future, and ultimately there is only gonna be one of those outcomes that, that, that ends up being the actual one, but at the end of the day, you have to take in all these disparate inputs and think through, uh, what the likely outcome can potentially be, and sometimes you're, you're wrong in it. Far out seeds the, uh, the outcome that you actually thought was most likely. And so therefore, were you wrong in your probability waiting? Or was it, was it a, uh, outsized outcome that actually ended up occurring that existed on the very far end of the distribution scale? Um, I tend to think about just making the best risk adjusted return that you potentially can sort of like playing blackjack and you can see the dealer's hands on the other side. And while You can, you can split, you know, w…

AI assessment note: “Yeah, no, I, I definitely think it, uh, it can be dangerous.”

Q you are with Redpoint and you're sitting thinking, huh, why are we getting challenged? What does that conversation look like? Is it Another multi-stage fund, Andreessen, Sequoia, Founders Fund, you name it. Is it, huh, Josh Buckley and Lockie Groomer eating our lunch? Is it, huh, the Harry's of the world are taking media in a different way? Like, where is the competitive element that you guys go, yeesh, shit?

A Yeah, I mean, I think it's all, right? It's, it's, I think the venture capital world that we live in today is, uh, is more akin, we went from a generation, and I, I've made this analogy, that we were in the generation of Broadcast television, right? Where there were only a handful of channels and what you were, the TV you were making was what was most broadly appealing to as many people as possible. And so you made happy days and I love Lucy and all that stuff, right? Then we moved to the cable news, uh, era where there was some level of personalization, right? There might've been ESPN or Fox news or CNBC or MSNBC or whatever MTV, there was some level of personalization, but it wasn't super personalized to each individual. And now in this era of streaming wars or TikTok or whatever you want to call it, everything's hyper-personalized to every individual entrepreneur. And so if you want an early stage FinTech only fund to support you, QED is out there or Ribbit's out there, right? If you want, you know, the preeminent brand that exists, uh, with the, the biggest, uh, access to capital and all of that, that firm's out there. If you want the, the, the firm that's going to leave you alone and give you as much capital as they possibly can, that firm's out there. And so I think, uh, I think all of these different forces, like if you're looking for any one thing out of a potential, uh…

AI assessment note: “Yeah, I mean, I think it's all, right?”

Q What crossover fund have you been most impressed by?

A Um, oh, well, I guess, I guess the, if I were to say pure crossover fund, I've, uh, I've really, uh, admired what, uh, the folks at KOTU have done in terms of building their brand and awareness at the, uh, the late stage growth market. I think that they've done a lot of, a lot of amazing stuff. I think in pure growth, uh, I, I just have infinite amounts of respect for, uh, Sequoia's growth fund, the folks over at Meritech and the guys over at Iconic. Uh, I think that all those groups do a really good job picking and, um, I, I, I want to beat all of them every single day and I wish them very poorly, but, uh, I have a lot of respect for what they're doing and a lot of friends at those places. And so, uh, I know when we're going head to head in an opportunity, you can't go wrong if, if a founder picks to work with them and, and they all do a very good job of picking, uh, to be in great companies. And so I, a lot of respect For the, for the game on the field, we play against all those firms.

AI assessment note: “I've really admired what the folks at KOTU have done”

Q which is a show where we study hyper growth companies. Is that you always underestimate how big your winners will be consistently across all of them. Twilio. Great example. Would anyone put Twilio anywhere near it is today? Never. And so you always are led to say no by outcome scenario plans, I find, uh, and underestimate them. So why do you still do them? And is it not dangerous?

A Yeah, no, I, I definitely think it, uh, it can be dangerous. At the end of the day, there's only a single outcome, right? And what is it? Annie Dukes in her book, Thinking in Bets calls it resulting when you end up looking back based on the result and having that inform the decision. I ultimately think, um, in terms of the probability weighting, uh, I, I think that there is no certainty by which we, uh, I can make decisions. I don't know for other people, but, uh, ultimately I, I sort of view that there's a, uh, there's a spectrum of potential outcomes that can exist, uh, in, in some world in the future, and ultimately there is only gonna be one of those outcomes that, that, that ends up being the actual one, but at the end of the day, you have to take in all these disparate inputs and think through, uh, what the likely outcome can potentially be, and sometimes you're, you're wrong in it. Far out seeds the, uh, the outcome that you actually thought was most likely. And so therefore, were you wrong in your probability waiting? Or was it, was it a, uh, outsized outcome that actually ended up occurring that existed on the very far end of the distribution scale? Um, I tend to think about just making the best risk adjusted return that you potentially can sort of like playing blackjack and you can see the dealer's hands on the other side. And while You can, you can split, you know, w…

AI assessment note: “I definitely think it, uh, it can be dangerous.”

Q So our biggest asset is time, and when we chatted before, you said VCs have gotten lazy over the last two years. Um, what did you mean by this, Logan?

A I think, um, the laziness occurred because there were a bunch of, uh, people, ventures, Venture has been a pretty cottage asset class, right, for the last, whatever, 30 years, and it's been institutionalized more in the last, you know, five than it had in the previous 25, in my opinion, and so what, what you, what you saw were a bunch of people that were SaaS, uh, maybe software investors, or maybe they were early to fintech, or maybe they got lucky with one consumer company that hit it big, and they confused the fooled by randomness of being at the right place in the right time With them actually being good investors, and I think we saw a whole vintage of people that, that sort of fit this bill, and they, they came of age in, I don't know, 2005 through 20 15, and founders came to them, right, and founders pitched them in a meaningful way, and founders asked or begged them for capital to support their business and their ideas, and there wasn't this tension that existed between buying and selling, That I think, uh, is healthy in the ecosystem in general, where, uh, entrepreneurs are looking for both capital, but then also looking to pick who they want to work with, right? And investors are also looking for who they want to invest in, what ideas they believe in, but also earning the right to invest in those opportunities. And so there is this tension that I think is healthy in th…

AI assessment note: “the laziness occurred because there were a bunch of, uh, people”

Q mentioned also what you look for in startups, you're very much located in the B to B space, a space where a lot of investors are very much focused on whether you can get to ten million ARR by two, by year two, and what your churn is, and all these metrics. Is that very much your thesis in approaching startup evaluation, or do you take a more holistic approach?

A Yeah, no, there's definitely two aspects of it. One is just the framework of, uh, points in time that will look at businesses. This is, this is as much pattern recognition as anything else, but I sort of think about it as the ones, uh, of stages, and so there's the one million in ARR standpoint, there's the one million, uh, that you're adding a quarter, and then there's the one million that you're adding a month, and so those are Three different points in time in a business's journey, and I think we'll, we'll take it from a different perspective at each point as we're looking at it, and I think we have a pretty good framework of evaluating those types of opportunities. Um, so that's certainly the pattern recognition side from a metric standpoint, but at the end of the day, we do need to understand the markets, and so seeing the kind of pull through from a customer standpoint is important, but if it's an area that we don't have a thesis in, Uh, we're not going to get up to speed quick enough to make a decision, and I don't think we'll ultimately be the right partner for you if we really don't know your market and the ability to, to speak to it, at least in some form, initially on the conversation.

AI assessment note: “there's definitely two aspects of it. One is just the framework of”

Q is technically, I think it was Brad Feld said on the show to hire and fire the CEO single job. Like when you think about your role as a board member, how do you view your role then? If you don't want to remove this, not want to, but if you're not willing to ever remove the, CEO. And how has it changed over time? You've changed. How's it changed?

A Yeah. Um, I, so I don't view, uh, the role, my role as a board member necessarily to hire and fire the CEO exclusively. Um, I, I think that, uh, that's certainly an element and can be a part of the job, but the very literal, if ever you're going to the votes, Uh, that, uh, are, hey, do you have the power to get something done with regard to removing the CEO barring something, uh, that is totally, uh, ethical or cataclysmic for the business? Um, I think if ever you're going to the votes and using your role as a board member to oust the CEO, something else is broken down along the way in the journey and the relationship you built with, with the founder and, and the rest of the board. Uh, so I don't know. I mean, Brad, Brad has done this a lot longer than I have, and, uh, I'm sure he's been in a lot more of these situations in which this has been totally necessary on behalf of either existing investors or on behalf of other, uh, employees at the business. Um, but that's, that's not how I wake up every day and thinking about my role. I view my role as being, earning the right, uh, to be a trusted confidant to the CEO and the executive team. And I, I very much, uh, view all those words as important, earning the right to be a confidant. And if, if part of that ultimately involves helping the individual to see that there might be a better path for the business going forward, for their…

AI assessment note: “I view my role as being, earning the right, uh, to be a trusted confidant”

Q So as a young chap entering the industry, I'd love to hear how you, how you've gone about trying to build your, your own personal brand and identity in, in a sea of, uh, identities and people vying for the attention, you know, VC blogs are second to none now. So how have you gone about trying to build that personal brand, and what strategies have you used?

A Yeah, totally. So I, I think, uh, first and foremost, it's just about being authentic to who you are. Um, and I've always, you know, before going into venture, before that I was kind of exposed to it, uh, there was always a veil of secrecy around it. It seemed, at least to me, and it was kind of a, a black box, um, that I didn't really understand what the inputs were. I understood the outputs, but I, I didn't really know what went on into the decision making process. And so, I think podcasts like this are great and kind of unveiling how, who the people are and how they think about it. But, uh, my approach has just been to be as, as authentic to who I am and what I care about. And so hopefully that resonates with, uh, the people that I, that I work with. You know, it's not necessarily if you're, if you're very transparent about who you are and what you care about and some of those things, it's not necessarily going to be for, for all people. Uh, but, but I found kind of building a brand or at least, uh, thinking, um, thoughtfully about who you are can be, uh, pretty taxing unless you're being authentic to, uh, to your personality. And so that's been kind of the most consistent thing that I've thought of in, uh, approaching my thought process from a more public perspective.

AI assessment note: “my approach has just been to be as, as authentic to who I am”

Q kind of the dearth of B's C's and D's because people are kind of retreating with their cash deposits. Um, are you advising founders now to not go out and raise? Because for me, I'm like, you cannot align your fundraise To macro markets, because six months time, it could be worse than it is now. 12 months could be even worse. If you need to raise, just fucking raise.

A Yeah, you know, right now is particularly weird, and I think it's most weird for those Series B folks, where to your point C, Series A, it's mostly business as usual. Maybe it's a little higher at the earlier stages, maybe it's a little lower at the Series A stages, but in those two buckets, I think it's, you know, game on, and ultimately people are investing. Series B is kind of the weird one, Series C maybe to a lesser extent, where, where there aren't a ton of data points out there in the market for what these, Businesses are worth, right? And so there aren't a lot of comps. There aren't a lot of people that are actively making the market for these potential investment opportunities. And so while I think that if you go out right now to raise, or if you went out two months ago to raise, you might ultimately get a far higher price than you would two months from now. Ultimately, the market was kind of reeling in such a way that there's people that are doing a bunch of different things. Some people are saying they're actively investing, but they're not, you know, they're kind of wasting your time. Some people are actively investing, but they're actively investing at, you know, 50% below what you think you're worth. And then there are some people that are saying, hey, the market was this a month ago. In my mind, it's still this today, right? And so I think what happened over the …

AI assessment note: “my only advice and potentially holding off, and I agree with you”

Q integrating that to the branding. One thing I always get concerned about is if you're too outwards in Displaying your thoughts and feelings on a particular market. Say, uh, mobile payments. I can't stand mobile payments, and I'm very outward in stating so on my Medium blog. Do you ever worry that by having such a set thesis that you could deter startups from coming to you with their idea?

A That's, that's an interesting point, and it's certainly, um, I think you want your arms around the types of things that you like to do, and, uh, that you like to spend time on. And, uh, and so, at the end of the day, I, I like looking for opportunities that are going to turn into transformative businesses. There are certain of those that I feel like I have my arms around and can get up the speed much quicker, and you're not talking to someone that, that has no perspective on where you're coming from, and you need to go through and explain the last 20 years of the industry and how we got to this point. And so, I prefer, uh, every conversation that, that I have with a company I'm coming with some framework and some ability to assess what they're doing and whether or not I personally find it interesting. And so there's a lot of ways to, to build companies and there's a lot of, uh, value to be created in doing so. But the more you can stay kind of targeted and focused, I think the ability to get up the curve and have meaningful conversations with, with entrepreneurs happens much quicker. And so I really do try to stay within the bounds of what I understand for that reason.

AI assessment note: “the more you can stay kind of targeted and focused”

Q So as a young chap entering the industry, I'd love to hear how you, how you've gone about trying to build your, your own personal brand and identity in, in a sea of, uh, identities and people vying for the attention, you know, VC blogs are second to none now. So how have you gone about trying to build that personal brand, and what strategies have you used?

A Yeah, totally. So I, I think, uh, first and foremost, it's just about being authentic to who you are. Um, and I've always, you know, before going into venture, before that I was kind of exposed to it, uh, there was always a veil of secrecy around it. It seemed, at least to me, and it was kind of a, a black box, um, that I didn't really understand what the inputs were. I understood the outputs, but I, I didn't really know what went on into the decision making process. And so, I think podcasts like this are great and kind of unveiling how, who the people are and how they think about it. But, uh, my approach has just been to be as, as authentic to who I am and what I care about. And so hopefully that resonates with, uh, the people that I, that I work with. You know, it's not necessarily if you're, if you're very transparent about who you are and what you care about and some of those things, it's not necessarily going to be for, for all people. Uh, but, but I found kind of building a brand or at least, uh, thinking, um, thoughtfully about who you are can be, uh, pretty taxing unless you're being authentic to, uh, to your personality. And so that's been kind of the most consistent thing that I've thought of in, uh, approaching my thought process from a more public perspective.

AI assessment note: “my approach has just been to be as, as authentic to who I am”