The Exchanges

Q What is the single best board you're on? Who's the single best board member you work with? And what makes the best board the best board?

A So, uh, so a bunch of different questions there. Uh, the most, uh, fun I have regularly on a, on a board right now is, uh, with, I would say cross beam, uh, mostly because I just really liked the people around the table. Bob Moore, the CEO is fantastic. Uh, Matt Turk is a very good friend. He led the Series A. Andy McLaughlin from Uncork led the Seed, and then we have a fun group from Andreessen Horowitz as well involved. So I think as a group, we just have a lot of, uh, a lot of fun together of the boards I'm on right now. Uh, the best single board member I've worked with, Neera Jagarwal was my mentor at Battery. He was fantastic. Um, two that I've really appreciated, uh, getting to know are, uh, Rob Ward from Meritech, just

AI assessment note: “the best single board member I've worked with, Neera Jagarwal”

Q Tell me, for those that didn't listen to that show where I was like a BBC newsreader, um, how did you make your way into the world of venture, and how did you come to be a partner at Redpoint, obviously, today?

A Yeah, totally. So, so, uh, I kind of found it accidentally, which, um, I, you, you hear people today talk about, uh, when I talk to young kids in college or whatever, they're, they're so purposeful about what they want to do, and they want to go after venture and get into tech, and they're very specific about the firms they want to work with. I didn't even know what venture was until I was 23, 24 or something. And I, I actually, it sounds silly and this, this couldn't happen today, but I did investment banking out of undergrad, uh, ended up at a small boutique investment bank doing software advisory. And, uh, I worked alongside, um, the, the Vista equities of the world and the TA associates, the JMIs, uh, and actually got some exposure to folks like battery, Excel, Bessemer, uh, red point. So, Uh, I actually raised my hand and said I wanted to go over to one of those places. Uh, most of them said no, or, or who are you? But, uh, I actually had a handful of interviews, one of which was Redpoint, one of which was Battery. Uh, Battery gave me an offer. Redpoint did not. Uh, I, I went over to Battery. I was there for six years and, uh, the Redpoint folks kind of stay on, stayed on top of me and, uh, they wanted to correct the error of their ways and not making me an offer when I was associate. And so I went over, uh, to Redpoint, I guess it was December, 2019, and joined, uh, at th…

AI assessment note: “I went over to Redpoint, I guess it was December, 2019”

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

A So AcuityMD was the, uh, was the most recent investment that I, that I said yes to. Uh, the seed slash series A was done by Eric Vichria from Benchmark. I did what was called the series A, was more like a series B. Uh, what got me most excited about it was, it was in this underserved market That had an opportunity, uh, that the founders recognized to bring tech and specifically CRM and targeting. Uh, so they operate within the medical device space. And so what they're building is something akin to zoom info plus Salesforce for med devices. And these founders had that unique insight that this actually maybe wasn't a big enough market as a, as a standalone of any one of those two, but combined together, if you could bring these two things to market, Then it actually could be a really big, interesting, uh, interesting opportunity, and so they had that insight, and then the founders are just so tireless and thoughtful in their approach of building product and recruiting and building this company. Uh, the CEO, Mike, was a swimmer, and you can just kind of tell, I, I, I think swimmers in general are kind of crazy to begin with, that they put their head down for hours a day and don't talk to anyone and just put one arm in front of the other while you kick. There's a level of discipline that that requires, and I use that as an example of just how disciplined and thoughtful he is in the…

AI assessment note: “So AcuityMD was the, uh, was the most recent investment that I, that I said yes to.”

Q Often in the early stage, we hear about ownership sensitivity. I need 10%. I need 15%. When we think about the three to five X requirement with a 10 X upside, do you have an ownership requirement or is it merely a multiple on dollars?

A Multiple on dollars. I think typically, I mean, obviously it's easier to own 10, 15, 20% plus of a business and have those returns end up generating the three to five X with 10 X plus upside. But we've been fortunate enough to be involved in companies like Stripe and Twilio and, and Snowflake and DraftKings and, uh, SentinelOne and, uh, a bunch of others that had been just really, uh, uh, far hit home runs. And so when those ultimately happen, uh, they can far out Seed the ability of owning 12% of any individual company. So we really focus on the, the outcomes more than the percentages at our stage. I know our early stage team spends more time thinking about ownership.

AI assessment note: “Multiple on dollars.”

Q if you are in an untenable market, Even the best founder will not be able to get out. Like, truly untenable. Social, political unrest. Currency destroyed. One of these situations can absolutely tank a company, no matter how good the founder is. Emerging markets company. Um, my question to you is, when you think about your biggest miss or mistake, what is it, and how did that change your mindset?

A I think at the, at the growth stage, uh, to some extent I have, uh, at times gotten hung up around the individual machinations of the market at that moment in time, rather than looking far off in the future and just saying yes or no, do we think this will happen? And yes or no, will this be the company to do it? And so, uh, while we were fortunate enough to be an investor, uh, uh, in Snowflake at Redpoint, I remember back at Battery looking at the opportunity and just thinking, hey, it just, the, the customer calls at the time were kind of raw about the business and, and how well the cloud was actually working. Amazon and Redshift seemed like such a formidable competitor. Who app ever wanted to compete with Amazon on their home turf, which was AWS and, and what we thought was Redshift and EC two at the time. Like, why would you make that investment? That seems like something that you're, you're jumping into a, uh, you know, shark filled waters there. And, uh, and I think what, what, what I learned from that is one, if you look far enough in the future, do you think something is inevitably going to happen? And in this case, the, the cost of compute and the need for performance was just so apparent that Redshift wasn't going to be able to meet that need. That there was going to be someone else that ended up coming in and doing it, and if we had looked at the founding team and the…

AI assessment note: “what I learned from that is one, if you look far enough in the future”

Q relatively low prices, given the fact that they would take additional money at this stage. You should be concentrating capital into winners and being very aggressive about it. But I'm not, because I don't quite know where the knife's falling, and I don't want to catch a falling knife. How do you think about the level of aggression with which you concentrate capital into existing portfolio, given the moderated pricing?

A I think it's a function of stage, right? And so to some extent, if, uh, at the later stages, you have to be very beholden to what public markets ultimately are going to be willing to pay. And we saw a dislocation that existed at the later stage versus, uh, the public markets that occurred over the course of the last couple of years. And it certainly has existed, uh, in a meaningful way in the last six months where we're still seeing businesses get done at, uh, or we were this summer seeing businesses get done at 200 times, 300 times ARR. When the public markets were saying like at best you could trade at, I don't know, 20 times forward revenue or something. And so at the later stages, you need to be careful there because ultimately that's where liquidity is going to come from in some of these high flyers. At the earlier stages, I think if you have businesses that are working and it's a low enough absolute valuation and you need to think through what your blended cost is going to be and what your portfolio concentration makes sense and all of that stuff that are kind of the fund level construction things. But I actually think it is a great time to be doubling down into the winners or just providing them more runway because ultimately, hey, if you get into a business at 50 post and you really think it's going to be an important company, it's going to be a great investment whether…

AI assessment note: “I think it's a function of stage, right?”

Q pray optionality at the early stage, and then we're going to concentrate capital into our winners and really build our ownership. I go, it's lovely in theory, but building ownership in the best companies, truly the best companies, is very difficult to do. Do you think that it is possible to really build ownership in your best companies when you have the best multi-stage funds hunting them harder than ever?

A I've seen some folks do it really well. I think, um, Sequoia has always done a good job of this. I think Founders Fund has done a good job of this. I think one of the, the people that do it well don't view, uh, the, the initial investment as a call option on later investment opportunities. They instead view it as, hey, we've made this investment and if it works and we're going to treat it like it's a full investment, like we're on the board, whether or not we are, we're going to give it the full support of our partnership, all the portfolio services we may have, all of that stuff. And then if the opportunity arises that, uh, it's really working, then we're going to lean in and provide them more capital. And the ones that don't do it well are the ones that really view this as out of the money call options. And if, if, if the opportunity presents itself, we're going to try to get sharp elbowed and box out other groups. And I've yet to see that really work. It might work for one round, but then you really piss off the founder and the round construct and all that. And then they go out of their way to make it not work at later stages. So I, I'm kind of mixed. There are some groups that do this really well. Um, and then I think there are a lot of groups that are a little sloppy with it.

AI assessment note: “I've seen some folks do it really well. I think, um, Sequoia has always done”

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 Often in the early stage, we hear about ownership sensitivity. I need 10%. I need 15%. When we think about the three to five X requirement with a 10 X upside, do you have an ownership requirement or is it merely a multiple on dollars?

A Multiple on dollars. I think typically, I mean, obviously it's easier to own 10, 15, 20% plus of a business and have those returns end up generating the three to five X with 10 X plus upside. But we've been fortunate enough to be involved in companies like Stripe and Twilio and, and Snowflake and DraftKings and, uh, SentinelOne and, uh, a bunch of others that had been just really, uh, uh, far hit home runs. And so when those ultimately happen, uh, they can far out Seed the ability of owning 12% of any individual company. So we really focus on the, the outcomes more than the percentages at our stage. I know our early stage team spends more time thinking about ownership.

AI assessment note: “Multiple on dollars.”

Q if you are in an untenable market, Even the best founder will not be able to get out. Like, truly untenable. Social, political unrest. Currency destroyed. One of these situations can absolutely tank a company, no matter how good the founder is. Emerging markets company. Um, my question to you is, when you think about your biggest miss or mistake, what is it, and how did that change your mindset?

A I think at the, at the growth stage, uh, to some extent I have, uh, at times gotten hung up around the individual machinations of the market at that moment in time, rather than looking far off in the future and just saying yes or no, do we think this will happen? And yes or no, will this be the company to do it? And so, uh, while we were fortunate enough to be an investor, uh, uh, in Snowflake at Redpoint, I remember back at Battery looking at the opportunity and just thinking, hey, it just, the, the customer calls at the time were kind of raw about the business and, and how well the cloud was actually working. Amazon and Redshift seemed like such a formidable competitor. Who app ever wanted to compete with Amazon on their home turf, which was AWS and, and what we thought was Redshift and EC two at the time. Like, why would you make that investment? That seems like something that you're, you're jumping into a, uh, you know, shark filled waters there. And, uh, and I think what, what, what I learned from that is one, if you look far enough in the future, do you think something is inevitably going to happen? And in this case, the, the cost of compute and the need for performance was just so apparent that Redshift wasn't going to be able to meet that need. That there was going to be someone else that ended up coming in and doing it, and if we had looked at the founding team and the…

AI assessment note: “I remember back at Battery looking at the opportunity and just thinking”

Q What is the single best board you're on? Who's the single best board member you work with? And what makes the best board the best board?

A So, uh, so a bunch of different questions there. Uh, the most, uh, fun I have regularly on a, on a board right now is, uh, with, I would say cross beam, uh, mostly because I just really liked the people around the table. Bob Moore, the CEO is fantastic. Uh, Matt Turk is a very good friend. He led the Series A. Andy McLaughlin from Uncork led the Seed, and then we have a fun group from Andreessen Horowitz as well involved. So I think as a group, we just have a lot of, uh, a lot of fun together of the boards I'm on right now. Uh, the best single board member I've worked with, Neera Jagarwal was my mentor at Battery. He was fantastic. Um, two that I've really appreciated, uh, getting to know are, uh, Rob Ward from Meritech, just

AI assessment note: “The best single board member I've worked with, Neera Jagarwal was my mentor at Battery.”

Q And then, speaking of pattern recognition, as a relative newbie to the VC scene, how are you looking to develop your own personal pattern recognition when it comes to startups?

A Yeah, no, it's a hard one, uh, because you've only seen as much, I've only seen two years worth of, uh, information here in, uh, in what companies have done and what's been successful. So from a pattern recognition standpoint, I would say I'm a big reader of just everything I can possibly get my hands on about businesses and how they got started, uh, particularly in the last 20 years. Um, so I go back and read the, you know, the story of eBay, uh, the story of, there's a book about the PayPal wars is the name of the book, and understanding how PayPal got to where they were, um, understanding the story of Amazon, understanding LinkedIn, and Salesforce, and Oracle, and PeopleSoft, and all those businesses, and, and that kind of, uh, serves as the pattern recognition to some extent, and then everything else outside of that is really by osmosis. Um, being around, Having a firm that's been around for 33 years, uh, like Battery has, and having partners that have been here for, you know, 1520 years, um, they've seen a lot of things, and so I'm really trying to learn from the people around me on a day-to-day basis and, and pick up little snippets of information from what they've seen in their, their history, and so it's kind of those two components inform my own, uh, pattern recognition capabilities.

AI assessment note: “I'm a big reader of just everything I can possibly get my hands on”

Q One in the end, baby. I do want to ask, and again, fuck it, off schedule. Battery, it's a phenomenal institution as well. Um, takeaways from that. Are there one or two big takeaways where you're like, that really shaped how I think about investing?

A Yeah, it's funny. I mean, uh, literally, like, Redpoint turned me down, and, uh, and then all that happened in Between them hiring me back as an equal partner and, uh, and, and, uh, turning me down was my experience at battery. I, I think battery in general, one, they're awesome people. Uh, two, they just very, um, they're very prudent about returning money to their limited partners and consistently delivering great returns. And they do that across a bunch of different strategies. So they'll be, they'll do early stage venture, late stage venture. They'll do growth equity. They'll do, uh, growth buyout type opportunities. They'll do lower bin market. Buyouts where they add on, uh, acquisitions to it and, and leverage with debt and all of that. And so I think honestly what battery does best and what I internalized most was just how to evaluate investment opportunities in general, right? It seems sort of, uh, pedantic in some ways and that, that, that should be the job in its entirety, but, but because they look at so many different things, it was very much a, uh, uh, a mash mashup of a bunch of different Styles of investing with everyone aiming just to be a good investor and deliver great returns to the limited partners. And so internalizing those different styles and understanding there's a bunch of different ways to make money under a single umbrella, I think was something that…

AI assessment note: “internalizing those different styles and understanding there's a bunch of different ways to make money”

Q today and what are VCs doing in some respects today? Uh, everyone tells me now is the best time to be investing. Um, interesting. Um, funny when, when you have a tequila and you're not speaking to their LPs, they say something different. But, uh, talk to me. How do you assess the state of the venture landscape today? And is it really the best time to be investing, Logan?

A It's up there for the best time that I've seen in my career. I think there was probably that stretch in 2014, 15, 16, that not a lot of people knew that software was going to be a big thing. And so that was certainly a great time to be investing as well, particularly when you saw the multiple appreciation that occurred over the next, whatever, six years. But right now, I think it is in that there's been a recalibration of price. And from entrepreneurs, what they're ultimately looking for from, uh, potential board members, investors on their cap table, all of that, that, that money isn't just money, that there are some other things that come along with that. And so I, I've never been more bullish about the different trends that are going on in the overall tech landscape right now, be that software digital transformation or FinTech or some of the stuff going on in healthcare. We're even seeing some pop up of, uh, of, of different consumer type companies, which it's been a little while since we've seen, but, but companies like Be Real or whatnot, we're even seeing some of the consumer businesses pop up again. And so I'm really enthusiastic about the opportunity set and price is a little bit more rational than what it has been. So I don't know best ever, but it's certainly a fantastic time to invest right now, particularly when compared to the last two or so years.

AI assessment note: “It's up there for the best time that I've seen in my career.”

Q pray optionality at the early stage, and then we're going to concentrate capital into our winners and really build our ownership. I go, it's lovely in theory, but building ownership in the best companies, truly the best companies, is very difficult to do. Do you think that it is possible to really build ownership in your best companies when you have the best multi-stage funds hunting them harder than ever?

A I've seen some folks do it really well. I think, um, Sequoia has always done a good job of this. I think Founders Fund has done a good job of this. I think one of the, the people that do it well don't view, uh, the, the initial investment as a call option on later investment opportunities. They instead view it as, hey, we've made this investment and if it works and we're going to treat it like it's a full investment, like we're on the board, whether or not we are, we're going to give it the full support of our partnership, all the portfolio services we may have, all of that stuff. And then if the opportunity arises that, uh, it's really working, then we're going to lean in and provide them more capital. And the ones that don't do it well are the ones that really view this as out of the money call options. And if, if, if the opportunity presents itself, we're going to try to get sharp elbowed and box out other groups. And I've yet to see that really work. It might work for one round, but then you really piss off the founder and the round construct and all that. And then they go out of their way to make it not work at later stages. So I, I'm kind of mixed. There are some groups that do this really well. Um, and then I think there are a lot of groups that are a little sloppy with it.

AI assessment note: “I've seen some folks do it really well. I think, um, Sequoia has always done”

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: “they confused the fooled by randomness of being at the right place in the right time”

Q this today. I got quite a lot of hate, actually, probably unsurprisingly. Um, but I basically said, Hey, it's a chance to build trust. Actually mark down your book and be very clear with your LPs about what really is in the portfolio and what its true value is. Do you agree that we're not seeing the markdown? And how do you think about that transparency on markdown of book?

A I was having a conversation with an LP yesterday about this, interestingly, and, uh, To some extent, it's, well, again, it goes back, it's a function of stage initially, right? And so, what is a Series A worth in today's environment versus what it was, ah, you know, six months ago or nine months ago? And you could argue based on performance, it should be written up potentially, right? If the company's 15 X'd in the last, whatever, 18 months, then you could say, hey, should we write this up altogether? At the later stages, I do think there's a handful of these businesses that, uh, if you're holding at the last round price, uh, that you're probably being a little superficial in your analysis of, like, what that business would be worth today in the public markets. I do think that there's an important, um, uh, it is an important part of the flywheel, though, of how you go about this, and not just with discretion, broad-based, kind of writing everything down across the portfolio, 15%, Or if you're gonna do that, being very, very transparent and upfront with your, uh, limited partners about how you're doing this. Now, some people are going to be very incentivized to say, hey, can you please keep your marks where they are? A fund to fund, for example, because that helps us go raise our money and we don't really need you subjectively and artificially writing down your marks just based …

AI assessment note: “being very, very transparent and upfront with your, uh, limited partners”

Q Do you, do you communicate that to the founder? This is one thing where I often struggle, which is like, okay, you lose faith. Do you say, Logan, I'm really sorry for these reasons? I actually don't, Believes that you have what it takes to lead this business anymore?

A I have yet to have that specific conversation with a founder, uh, in the case that I'm, I'm thinking about, uh, there was a board member, uh, who, who ended up leading the charge on that conversation. And, uh, ultimately I think the opportunity passed by anyway, and so it was kind of neither here nor there. Uh, in this, in this specific situation. Inevitably, if I, if I'm afforded the, the luxury of doing this for a long enough time, I, I'm sure that's a conversation I'm gonna have to have. And, um, that's kind of where it comes down to trust and building relationships with, uh, with the founders that you work with. That, uh, I, I found that people that at least I like working with are very pragmatic and, and understanding of themselves. That, uh, if, if I'm seeing it, there's probably a path To, uh, them also seeing it as well. Uh, I, I never want to be the one that's in there replacing the CEO if they also don't agree that there might be an opportunity for a better person to step in. Um, I, I just don't view that as, as something that's, uh, something that's a core part of the job. I think founders are sort of the lifeblood of what we get to do. And, uh, and so regularly replacing founders, I, I just don't view as an ethical thing that I want to be a part of, but If there, there are ways of soft diplomacy of convincing founders to, uh, to that, that maybe that's the right pat…

AI assessment note: “I have yet to have that specific conversation with a founder”

Q What the fuck is gonna happen to crypto?

A I think there's some value to be had in the crypto ecosystem. Uh, I don't think it's to the tune of twenty five billion dollars or whatever was put out last year from the venture ecosystem. I think there's a handful of use cases. I don't know what number that exactly adds up to. Uh, speculation and, uh, and gambling seems to be a, uh, decent enough use case. You throw in NFTs and I, I think there's some value there. And then some of this cross currency Border exchange related stuff. I think there's some utility there. I don't think that's nearly commiserate with the amount of money that's gone into the ecosystem. And so I think we're going to see a lot of zeros pop out of, uh, of the vintages of these crypto funds that we've seen recently.

AI assessment note: “we're going to see a lot of zeros pop out of”

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: “gives you a much quicker iterative feedback loop”

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 One in the end, baby. I do want to ask, and again, fuck it, off schedule. Battery, it's a phenomenal institution as well. Um, takeaways from that. Are there one or two big takeaways where you're like, that really shaped how I think about investing?

A Yeah, it's funny. I mean, uh, literally, like, Redpoint turned me down, and, uh, and then all that happened in Between them hiring me back as an equal partner and, uh, and, and, uh, turning me down was my experience at battery. I, I think battery in general, one, they're awesome people. Uh, two, they just very, um, they're very prudent about returning money to their limited partners and consistently delivering great returns. And they do that across a bunch of different strategies. So they'll be, they'll do early stage venture, late stage venture. They'll do growth equity. They'll do, uh, growth buyout type opportunities. They'll do lower bin market. Buyouts where they add on, uh, acquisitions to it and, and leverage with debt and all of that. And so I think honestly what battery does best and what I internalized most was just how to evaluate investment opportunities in general, right? It seems sort of, uh, pedantic in some ways and that, that, that should be the job in its entirety, but, but because they look at so many different things, it was very much a, uh, uh, a mash mashup of a bunch of different Styles of investing with everyone aiming just to be a good investor and deliver great returns to the limited partners. And so internalizing those different styles and understanding there's a bunch of different ways to make money under a single umbrella, I think was something that…

AI assessment note: “what battery does best and what I internalized most was just how to evaluate investment opportunities”

Q Have you ever had a company go bust and what was the biggest learning?

A I haven't yet. Uh, now we've been in a eight year bull run since I've been investing. I, I was on a board of a company that had to do a full recap. I had inherited the board and I, I thought about this. I, I give the founder a lot of credit because actually after the recap, he was able to, uh, turn it into a really successful outcome for all the people that participated in the, in the recap. I think the, uh, The thesis that was wrong at the point of the original investment was, ah, was ultimately, it was a little too beholden to, ah, trends associated with Google, Facebook, Amazon, some of these big players, and you dance with elephants, and there's a real risk that you get stepped on, and so I, I, I wonder at the point of investment if that was actually one of the real internalized probabilities that could happen, or if that was something that, that Snuck up on, ah, on the, the, the investment team over time. What I'll always tell our team internally is, I, I really don't care if something goes wrong, ah, in an individual investment, that's gonna happen, but it can't be something that we didn't have written out in the investment memo before. We have to know the entirety of the potential risks to the extent we can on the way in, ah, and do all the work so that we understand that, so that we're at least not surprised It's by things when they ultimately do hit bumps along the way…

AI assessment note: “I haven't yet. Uh, now we've been in a eight year bull run”

Q today and what are VCs doing in some respects today? Uh, everyone tells me now is the best time to be investing. Um, interesting. Um, funny when, when you have a tequila and you're not speaking to their LPs, they say something different. But, uh, talk to me. How do you assess the state of the venture landscape today? And is it really the best time to be investing, Logan?

A It's up there for the best time that I've seen in my career. I think there was probably that stretch in 2014, 15, 16, that not a lot of people knew that software was going to be a big thing. And so that was certainly a great time to be investing as well, particularly when you saw the multiple appreciation that occurred over the next, whatever, six years. But right now, I think it is in that there's been a recalibration of price. And from entrepreneurs, what they're ultimately looking for from, uh, potential board members, investors on their cap table, all of that, that, that money isn't just money, that there are some other things that come along with that. And so I, I've never been more bullish about the different trends that are going on in the overall tech landscape right now, be that software digital transformation or FinTech or some of the stuff going on in healthcare. We're even seeing some pop up of, uh, of, of different consumer type companies, which it's been a little while since we've seen, but, but companies like Be Real or whatnot, we're even seeing some of the consumer businesses pop up again. And so I'm really enthusiastic about the opportunity set and price is a little bit more rational than what it has been. So I don't know best ever, but it's certainly a fantastic time to invest right now, particularly when compared to the last two or so years.

AI assessment note: “It's up there for the best time that I've seen in my career.”

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: “I think it's a funnel, right? It kind of goes to how public markets”

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: “I think it's all, right? It's, it's, I think the venture capital world”

Q this today. I got quite a lot of hate, actually, probably unsurprisingly. Um, but I basically said, Hey, it's a chance to build trust. Actually mark down your book and be very clear with your LPs about what really is in the portfolio and what its true value is. Do you agree that we're not seeing the markdown? And how do you think about that transparency on markdown of book?

A I was having a conversation with an LP yesterday about this, interestingly, and, uh, To some extent, it's, well, again, it goes back, it's a function of stage initially, right? And so, what is a Series A worth in today's environment versus what it was, ah, you know, six months ago or nine months ago? And you could argue based on performance, it should be written up potentially, right? If the company's 15 X'd in the last, whatever, 18 months, then you could say, hey, should we write this up altogether? At the later stages, I do think there's a handful of these businesses that, uh, if you're holding at the last round price, uh, that you're probably being a little superficial in your analysis of, like, what that business would be worth today in the public markets. I do think that there's an important, um, uh, it is an important part of the flywheel, though, of how you go about this, and not just with discretion, broad-based, kind of writing everything down across the portfolio, 15%, Or if you're gonna do that, being very, very transparent and upfront with your, uh, limited partners about how you're doing this. Now, some people are going to be very incentivized to say, hey, can you please keep your marks where they are? A fund to fund, for example, because that helps us go raise our money and we don't really need you subjectively and artificially writing down your marks just based …

AI assessment note: “being very, very transparent and upfront with your, uh, limited partners”

Q Do you, do you communicate that to the founder? This is one thing where I often struggle, which is like, okay, you lose faith. Do you say, Logan, I'm really sorry for these reasons? I actually don't, Believes that you have what it takes to lead this business anymore?

A I have yet to have that specific conversation with a founder, uh, in the case that I'm, I'm thinking about, uh, there was a board member, uh, who, who ended up leading the charge on that conversation. And, uh, ultimately I think the opportunity passed by anyway, and so it was kind of neither here nor there. Uh, in this, in this specific situation. Inevitably, if I, if I'm afforded the, the luxury of doing this for a long enough time, I, I'm sure that's a conversation I'm gonna have to have. And, um, that's kind of where it comes down to trust and building relationships with, uh, with the founders that you work with. That, uh, I, I found that people that at least I like working with are very pragmatic and, and understanding of themselves. That, uh, if, if I'm seeing it, there's probably a path To, uh, them also seeing it as well. Uh, I, I never want to be the one that's in there replacing the CEO if they also don't agree that there might be an opportunity for a better person to step in. Um, I, I just don't view that as, as something that's, uh, something that's a core part of the job. I think founders are sort of the lifeblood of what we get to do. And, uh, and so regularly replacing founders, I, I just don't view as an ethical thing that I want to be a part of, but If there, there are ways of soft diplomacy of convincing founders to, uh, to that, that maybe that's the right pat…

AI assessment note: “I have yet to have that specific conversation with a founder”

Q I, I'm sure he is. I don't have the luxury of sitting on board with him, but why is he so good?

A Yeah, I think he has the right level of, of empathy and passion, and he knows, uh, he knows the inside out details of the companies he's, he works with. He knows the right altitude to talk to the different entrepreneurs, and you just know he genuinely cares and all this stuff is coming from a very good place. So he's willing to spend as much time as you want as an entrepreneur with you, uh, on all the problems that you have. He's willing to roll up his sleeves and be helpful, but he's also, Not only going to be a pushover and not only going to be your friend, he's going to push back when he thinks you're wrong, and he's going to help you learn from not just your own mistakes, but all the things that he's seen in his career as an operator or his career as an investor. And I think just his ability to synthesize all that stuff down and speak to people at the right level with the right tone. It's just, um, unlike anything I've really seen before, and so I, I, I've learned a ton from him and, uh, wish I could spend, uh, you know, as much time as possible kind of learning from the style that he takes to operating with these companies.

AI assessment note: “I think he has the right level of, of empathy and passion”

Q What the fuck is gonna happen to crypto?

A I think there's some value to be had in the crypto ecosystem. Uh, I don't think it's to the tune of twenty five billion dollars or whatever was put out last year from the venture ecosystem. I think there's a handful of use cases. I don't know what number that exactly adds up to. Uh, speculation and, uh, and gambling seems to be a, uh, decent enough use case. You throw in NFTs and I, I think there's some value there. And then some of this cross currency Border exchange related stuff. I think there's some utility there. I don't think that's nearly commiserate with the amount of money that's gone into the ecosystem. And so I think we're going to see a lot of zeros pop out of, uh, of the vintages of these crypto funds that we've seen recently.

AI assessment note: “we're going to see a lot of zeros pop out of, uh, of the vintages”