20VC: Is Now Really the Best Time to Be Investing? WTF is Happening at Growth Stage Investing? Why VCs Have Gotten Lazy Over the Last 2 Years? Investing Lessons from Hitting with Braze and Missing with Snowflake with Logan Bartlett, Managing Director @ Re

Logan Bartlett is a Managing Director @ Redpoint, a firm with a portfolio including the likes of Stripe, Nubank, Twilio, Netflix, Snowflake and many more incredible names. As for Logan, at Redpoint he has led investments in the likes of Ramp, Monte Carlo, Cribl, Crossbeam and Acuity MD to name a few. Before joining Redpoint, Logan spent over 5 years with the team at Battery where he made investments in Pendo, Amplitude, Dataiku, Braze and Kustomer. In Today's Episode with Logan Bartlett We Discuss: 1.) Entry into Venture: How Logan made his way into the world of venture joining Battery Ventures? What are 1-2 of Logan's biggest takeaways from his time with Battery? What does Logan know now that he wishes he had known when he started in venture? 2.) The Venture Landscape Today: Is now really the best time to be investing? How does Logan compare today to prior vintages? How does this differ when comparing consumer to B2B? How does Logan analyze the state of the growth market? Is anyone really doing deals today? If so, what is the discount on price vs last year? How do the public markets impact the later stage financings which have disappeared in the last 3 months? How do the later stage financings impact the early stage? Does Logan agree that "venture has never been less collaborative as it is today"? 3.) The Role of the Venture Investor: Why does Logan believe that VCs have gotten lazy over the last 2 years? Does Logan believe we will see even more GPs at the top retire in the downturn? How does Logan analyse his role as a board member today? How has his style changed over time? What is the single best board Logan is on? Why that one? Who is the best board member Logan works with? What makes this board member so good? How does Logan assess the importance of personal brand in venture today? Why does Logan believe no company should hire PR firms from the early days? 4.) Investing Style and Lessons: What has been Logan's single biggest hit as an investor? How did seeing that impact his mindset? What has been Logan's biggest miss? How did not doing the investment change how he thinks about making new investments today? How does Logan assess his own relationship to price? How has it changed over time? As a growth investor today, how important is ownership? How does this change with stage? Items Mentioned in Today's Episode: Logan's Favourite Book: Team of Rivals: The Political Genius of Abraham Lincoln Logan's Most Recent Investment: AcuityMD

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Harry Stebbings?

  Welcome back to another week in the world of 20VC with me, Harry Stebbings. And today's show is a fun one for me. I first met this guest over six years ago. I had him on the show then, and so much has changed since then that I've really wanted to make this round two happen for a while. And I'm so thrilled to welcome back Logan Bartlett, Managing Director at Redpoint. At Redpoint, Logan has led investments in the likes of Ramp, Monte Carlo, Cribl, Crossbeam and Acuity MD, to name a few. And before joining Redpoint, Logan spent over five years with the team at Battery, where he made investments in Pendo, Amplitude, Data IQ, Braze and Customer. And I do also want to say a huge thank you to Satish and Tom at Redpoint. Some amazing question suggestions today, and I so appreciated that. But before we move into the episode today, if you are a venture capitalist or corporate strategist,

• 0:43Harry Stebbings?

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• 1:28Harry Stebbings?

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• 2:13Harry Stebbings?

  And then you can sign up and start using your new business phone in minutes. Visit openphone.com/20vc. That's openphone.com/20vc to save 20% on your first six months. And finally, I love history. And you know what happens when you look at the history books of Silicon Valley? Cooley is all over it. They are the global law firm built around startups and venture capital. Since forming the first venture fund in Silicon Valley, Cooley has formed more venture funds than any other law firm in the world with 50 plus years. Working with VCs, they help VCs form and manage funds, make investments, handle the myriad of issues that arise throughout a fund's lifetime. So to learn more about the number one most active law firm representing VC backed companies going public,

• 2:56Harry Stebbings?

  head over to Cooley.com and also check out Cooleygo.com. But that is enough from me tonight. I'm so excited to welcome back to the show Logan Bartlett, Managing Director at Redpoint.

• 3:12Speaker 01

  You have now arrived at your destination.

• 3:15Harry Stebbings?

  Logan, this is such a joy to do. I remember years and years ago, and you don't even remember this. I remember everyone saying to me at a drinks party, there's this young associate, he's amazing, he's amazing. You've got to meet him, Harry. And they pointed to you. And this was way back in the day when I think you were at Battery. And we met years and years ago, you came on the show then. I'm so pleased that you're back. So thank you so much for joining me again.

• 3:37Speaker 02

  Of course. I'm glad to be here. I actually do remember that. We were at the, I think Mattermark was hosting a party at Saster. And this would have been probably 2015 or something. So way back when, but come in full circle. I want you to know that you were the only podcast I did from 2015 to 2022, the beginning of 2022.

• 3:56Harry Stebbings?

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

• 4:06Speaker 02

  Yeah, I kind of found it accidentally, which you hear people today talk about 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. Actually, it sounds silly, but I did investment banking out of undergrad, ended up at a small boutique investment bank doing software advisory. And I worked alongside the Vista Equities of the world and the TA associates, the JMI's, and actually got some exposure to folks like Battery, Excel, Bessemer, Redpoint. I actually raised my hand and said I wanted to go over to one of those places. Most of them said, "No," or "Who are you?" But I actually had a handful of interviews, one of which was

• 4:49Speaker 02

  Redpoint, one of which was Battery. Battery gave me an offer, Redpoint did not. I went over to Battery, I was there for six years, and the Redpoint folks kind of stayed on top of me. They wanted to correct the error of their ways and not making me an offer when I was associate. And so I went over to Redpoint, I guess it was December 2019, and joined at the beginning of 2020, and I've been here ever since.

• 5:09Harry Stebbings?

  Expensive error, Redpoint.

• 5:11Speaker 02

  That's right.

• 5:12Harry Stebbings?

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

• 5:23Speaker 02

  Literally, like Redpoint turned me down, and then all that happened in between them hiring me back as an equal partner and turning me down was my experience at Battery. I think Battery in general, one, they're awesome people. Two, 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 growth buyout-type opportunities, they'll do lower mid-market buyouts where they add on acquisitions to it 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?

• 6:04Speaker 02

  It seems sort of pedantic in some ways in that that should be the job in its entirety. But because they look at so many different things, it was very much a mashup of a bunch of different styles. Sales 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 I really appreciate today in looking at different investment opportunities.

• 6:33Harry Stebbings?

  Now, speaking of looking at investment opportunities today, we spoke beforehand about, you know, what is venture today and what are VCs doing in some respects today? Everyone tells me now is the best time to be investing. Interesting. Funny, when you have a tequila and you're not speaking to their LPs, they say something different. How do you assess the state of the venture landscape today? Is it really the best time to be investing, Logan?

• 6:54Speaker 02

  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, it is in that there's been a recalibration of price from entrepreneurs, what they're ultimately looking for from potential board members, investors on their cap table, that money isn't just money, that there are some other things that come along with that. 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,

• 7:39Speaker 02

  or fintech, or some of the stuff going on in healthcare. We're even seeing some pop-up of different consumer-type companies, which it's been a little while since we've seen companies like BeReal or whatnot. And so I'm really enthusiastic about the opportunity set and price is a little bit more rational than what it has been. 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.

• 8:02Harry Stebbings?

  As a pre-seed investor in BeReal, I now feel like Jason Calacanis with Uber in this moment.

• 8:07Speaker 02

  I started hearing about it six months ago, and it's one of those things, I'm mostly B2B software, but occasionally you hear about something and you're like, I really wish I wasn't so focused on what I do, because this sounds great. And it seems like they've just executed absolutely phenomenally.

• 8:21Harry Stebbings?

  It's an incredible business. 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 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?

• 8:42Speaker 02

  It's a funnel, right? It kind of goes to how public markets end up flowing through to private markets in general. 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 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. 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 last money post around valuations that you're not seeing them go out there and fundraise right now.

• 9:25Speaker 02

  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 say, "We would have invested $200 million at a $2 billion valuation. Now we're going to invest $20 million into 10 companies." And so take that same 20 million and invest it across the board. So that's squeezing the earlier-stage groups more and more. And I assume as you're seeing, it's pushing down into the seed, pre-seed part of the house because ultimately there are a finite number of these opportunities. I think at the earlier stages, people can really talk themselves into the difference of four posts versus six posts versus 12 posts really isn't going to matter.

• 10:06Speaker 02

  Just put this money to work and if it works, we'll be able to put in far more capital later on. While it might be 100% difference in price between 4 million and 8 million posts, you're not seeing the level of financial rigor and analysis that you probably would at the later stage, which to your point, probably leads to some inflation that's actually occurring at the earlier stages.

• 10:27Harry Stebbings?

  I've got two questions listening to you there. You mentioned there about kind of the dearth of Bs, Cs, and Bs because people are retreating with their cash deposits. 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 raise.

• 10:48Speaker 02

  Yeah, you know, right now is particularly weird, and I think it's most weird for those Series B folks, where to your point, see, 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 game on, and ultimately, people are investing. Series B is kind of the weird one, Series C maybe to a lesser extent, where there aren't a ton of data points out there in the market for what these businesses are worth. 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. 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

• 11:33Speaker 02

  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. And so I think what happened over the last couple of months is you were just seeing, while the market could have been higher from a price standpoint, you were seeing a lot of founders kind of get jerked around with regard to valuation, with regard to whether or not people were actually actively investing. And so my only advice in potentially holding off, and I agree with you, if you don't have

• 12:14Speaker 02

  the luxury to go raise, having capital is a prerequisite for success at all, and so I would go raise if you need it. If you're afforded a little bit more of a time horizon to wait, I've encouraged most of the founders that I work with, maybe wait till after Labor Day, maybe wait to sometime a little bit later in the fall. I think we're starting to get back to the point that one's willing to make investments. Everyone is within some zone of what valuations are worth. And so I think that leads to just a much more efficient fundraising process and ability not to say, hey, this person's at 500 posts, and this person's at 200 posts, how do we even make a decision? But instead, actually pick the partner that you want to work with, and usually, these people are going to be within some bound that hopefully you're able to get everyone

• 12:58Speaker 02

  to kind of march in line and pick the person you think is actually going to be most helpful to you as a founder.

• 13:03Harry Stebbings?

  I'm actually questioning myself here, Logan. I'm looking at myself going, okay, I've got a portfolio of what I think is very good assets. Harry, what are you doing? You should be much more aggressive in concentrating capital at 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?

• 13:34Speaker 02

  I think it's a function of stage. And so to some extent, if 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 the public markets that occurred over the course of the last couple of years. And it certainly has existed in a meaningful way in the last six months, where we're still seeing businesses get done at 200 times, 300 times ARR, when the public markets were saying like, at best, you could trade at 20 times forward revenue or something. 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

• 14:16Speaker 02

  and you need to think through what your blended cost is going to be and what your portfolio concentration makes sense. But I actually think it is a great time to be doubling down into the winners or just providing them more runway. Because ultimately, 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 or not you put in more at 55 or 70 post as well. So I would be doing that with some pragmatism associated with fun construct and absolute valuation, blended cost, all that stuff.

• 14:46Harry Stebbings?

  Can I ask, I often hear about managers say, we're going to spray and pray optionality at the early stage and then we're going to concentrate capital into our winners and really build our ownership. I guess 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?

• 15:08Speaker 02

  I've seen some folks do it really well. I think Sequoia has always done a good job of this. I think Founders Fund has done a good job of this. The people that do it well don't view the initial investment as a call option on later investment opportunities. They instead view it as, hey, we've made this investment 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 it's really working, then we're going to lean in and provide them more capital. The ones that don't do it well are the ones that really view this as out of the money call options. And if the opportunity presents itself, we're going to try to get sharp elbowed and box out other groups.

• 15:50Speaker 02

  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. There are some groups that do this really well. And then I think there are a lot of groups that are a little sloppy with it.

• 16:06Harry Stebbings?

  The challenge with that is then you have to be super good at picking. If you're going to take that very active role, you need to pick well.

• 16:12Speaker 02

  Yeah, you have to hold a really high bar there. At the end of the day, our only constrained resource oftentimes is time. If you're going to be treating this small investment like it's a big one, then you could be really upside down in terms of if that business doesn't work, how much you invested just from a time cycle standpoint into that company.

• 16:28Harry Stebbings?

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

• 16:37Speaker 02

  The laziness occurred because venture has been a pretty cottage asset class for the last 30 years. And it's been institutionalized more in the last five than it had in the previous 25. And so what you saw were a bunch of people that were SaaS 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. They came of age in 2005 through 2015, and founders came to them and founders pitched them in a meaningful way. Beg them for capital to support their business and their ideas.

• 17:22Speaker 02

  And there wasn't this tension that existed between buying and selling that I think is healthy in the ecosystem in general, where entrepreneurs are looking for both capital, but then also looking to pick who they want to work with. 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 was this tension that I think is healthy in the ecosystem. For a very long time, it was 100% on the side of the investors where the power existed. The last two years, I think it moved all the way to the entrepreneurs. Now we're back to a little bit of an equilibrium, but you've seen a lot of people retire in the last five years. A lot of very famous investors retire. I don't blame them at all because the game on the field has definitely changed and it's far more competitive than it was in their day.

• 18:07Speaker 02

  And you're chasing around people trying to earn the opportunity to invest. And when you came of age, when people showed up at your door and gave you a month to respond, I think it's probably pretty jarring to be chasing around founders or sending DMs or begging for intros. And so I think there was a group that got very rich, very fat and very happy, and ultimately decided it made more sense to take a step back than to try to adjust to the game on the field.

• 18:32Harry Stebbings?

  So when you're in a multi-stage fund like you are with RabPoint and you're sitting thinking, huh, where 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 Lucky Groomer eating our lunch? Is it, huh, the Harrys of the world are taking media in a different way? Where is the competitive element that you guys go, eesh?

• 18:55Speaker 02

  Yeah, I mean, I think it's all. I think the venture capital world that we live in today is more akin. We were in the generation of broadcast television, right? Where there were only a handful of channels. 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. Then we moved to the cable news era where there was some level of personalization. There might have been ESPN or Fox News or CNBC or MSNBC or MTV. There was some level of personalization, but it wasn't super personalized to each individual. And now in this era- Streaming wars or Tik Tok or whatever you want to call it. Everything's hyper personalized, every individual entrepreneur. And so if you want an early stage fintech only fund to support you.

• 19:38Speaker 02

  Q E D is out there or Ribbit's out there. If you want the preeminent brand that exists with the biggest access to capital and all of that. That firm's out there. If you want 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 all of these different forces, like if you're looking for any one thing out of a potential investor, there's going to be a firm or a person that services that. What does that mean for us? Well, I, I think it means that each individual at Redpoint has to stand for something and be known in some way, shape or form for what it is that they do to help rise above the noise. And then I think we need the sum of the parts of Redpoint to be greater than any of the individual coming together so that the brand actually stands for something.

• 20:21Speaker 02

  And when people think about it, Redpoint actually means something to them beyond any individual. The accumulation of the individuals, the accumulation of the brand, the accumulation of the companies we've been involved with actually stands for something. Because that's the only way we can cut through the noise of all the specialization that exists out there. And it's not going to work every single time for every single entrepreneur. We don't need any one individual thing to necessarily carry the day. But we do need the sum of our parts to be greater than who we're competing with. That's where we really focus is to make sure we have a suite of services or a suite of personalities or a suite of domain expertise that makes us rise above the noise and makes us win that individual hand to hand fight.

• 21:05Speaker 02

  And we're not always going to beat you or Lucky or Buckley. We're not always going to beat Sequoia or Founder's Fund or Andreessen. But we need to win our fair share of the great opportunities that exist out there. And so that's what I wake up every day kind of thinking about.

• 21:18Harry Stebbings?

  We said we'd have a discussion and I'm trying more and more Logan not to be like just yes, you're right. And I agree. I think that that two competing strategies of individual partner increase brand and fund increase brand sum of parts. I think that's actually idealistic. And what I mean by that is actually, I think you either go in the partner led star routine, which is like your Mark Suster at front. If you're Alexa, Hany at seven, seven, six style. Or it's your all in unison Sequoia. I think you could say benchmark, but I think it's like idealistic to try and do both at once. Do you not think?

• 21:51Speaker 02

  I think it's idealistic to try to do both at once. Inevitably, you're going to be pulled in one direction or the other. And you can look at where people kind of pick. One quick test of where people pick orientation of individuals versus the firm is like, where do blogs reside, right? Do blogs reside on someone's own Substack or someone's own domain? Or do they reside on the firm's website or the firm's medium or the firm's Substack? And there's definitely gray areas that exist between the two. But ultimately, I think 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, Andreessen Crypto, you don't think of as the same way of Andreessen Enterprise.

• 22:34Speaker 02

  You don't think Chris Dixon or Martin Casado or David George in the same way that you do Mark Andreessen or Ben Horowitz or Jeff Jordan. Maybe that's an exception to them. 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? 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, [email protected], I want to make sure that Logan means something more than it did the day before and that redpoint.com does as well. Where the pendulum exists on that spectrum, I think it's going to change for every individual, for every firm and all of that. But I think we're at least striving to have elements of both that are important for us.

• 23:17Harry Stebbings?

  We mentioned like competition and things that worry us. Things that worry me right now is actually the amount of GPs that are maintaining book value despite the book value not being what it is. Let's be clear. And we all know that not. And I tweeted this and I got quite a lot of hate, actually, probably unsurprisingly. 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?

• 23:47Speaker 02

  I was having a conversation with an LP yesterday about this. Interestingly, it's a function of stage initially. What is a Series A worth in today's environment versus what it was six months ago or nine months ago? And you could argue based on performance. It should be written up potentially, right? If the company is 15x in the last 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 if you're holding at the last round price, you're probably being a little superficial in your analysis of like what that business would be worth today in the public markets. It is an important part of the flywheel, though, of how you go about this and not just

• 24:29Speaker 02

  with discretion, broad-based, kind of writing everything down across the portfolio 15%. Or if you're going to do that, being very, very transparent and upfront with your 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 on your own analysis today. We would prefer you not do that. Some other people might be overexposed to venture because these marks are at a high level right now and their public books come down and their private book's still sitting high. And so they're saying, hey, can you take this down or take a little bit of pressure out

• 25:12Speaker 02

  of this system because we still want to be re-upping with managers and we can't if our target was 12% venture and now we're 18% venture or whatever it is. And so it is some level of delusion. If you actually believe that all of these companies are worth what they were worth six months ago and you're saying that with a straight face to your limited partners, then I think you're losing trust, right? 100%. I don't think you can be a prudent manager and look every person in the eye and say, hey, this is worth exactly what we thought it was worth six months ago. That just doesn't make sense to me. The construct by which you write down these investments or how to think about the holding value of these investments and how you go about communicating how you're adjusting

• 25:53Speaker 02

  these things, I think just doing broad-based write downs of late-stage companies, I think ultimately there's probably some nuance in there. I will tell you in talking to this LP yesterday, they said they saw Q2 was the big reckoning for people taking it down, but even then there were still a handful of people that didn't. And so they're expecting it to kind of flow through to the end of the year. But even still, I mean, is that actually an accurate reflection of what the market's worth? It's hard to say. These are very illiquid, private valuations. Until these things are in the public markets or until they trade hands, it's really hard to put the price to any of this stuff. And so Just having a disciplined structure of how you're doing it, I think is more important than taking down the marks themselves.

• 26:32Harry Stebbings?

  Can I ask you, everyone last year, they invested faster and they invested with less price sensitivity, I being one of them. Did you?

• 26:39Speaker 02

  No, I didn't. I only, no, I'm, how did you do that, Harry? I'm sorry. You're really showing your age here. No, listen up. Anyone that invested last year lost some level of price sensitivity. I for sure changed the underwriting framework by which we were evaluating companies, not in terms of what we thought they could be. Our simple underwriting framework for growth at Redpoint is three to five X with 10 X plus upside. And we really want to be investing in things that we think can be important longstanding public businesses. By that definition, we kept the framework the exact same as we always had. Now, when you're underwriting to a three to five X with 10 X plus upside and things are trading at 30, 40, 50 times in the public markets, inevitably, there's going to be some level

• 27:22Speaker 02

  of price sensitivity that adjusts, right, to the new state of the public markets. In that regard, for sure, like, we didn't have the same price sensitivity that we had had a year, two years before, mostly because the public markets had changed what things were worth. I think the good news, or at least what allows me to sleep at night, is while I wish that I invested at today's prices last year, there isn't a single investment that I wish I had back. That keeps me optimistic that maybe the 10 X plus upside case that we underwrote to, if things go right, maybe now that's 5X, 6X, 7X on some of these investments. But they still have that outsized tail opportunity, that they should be great, important companies

• 28:06Speaker 02

  for us if we picked correctly. Inevitably, there's going to be price pressure and returns are going to compress, but pretty proud of the portfolio composition that was built out last year for us, even if some level of price sensitivity was lost.

• 28:19Harry Stebbings?

  You mentioned the three to five X though with 10 X upside. That instantly correlates, obviously, to outcome scenario planning. The one learning that I have from doing the memo, which is a show where we study hypergrowth companies, is that you always underestimate how big your winners will be consistently across all of them. Twilio, great example. Would any of... Put to will you anywhere near it is today. And so you always are led to say no by outcome scenario plans, I find and underestimate them. Why do you still do them? And is it not dangerous?

• 28:47Speaker 02

  Yeah, it can be dangerous. At the end of the day, there's only a single outcome. Annie Duke's 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. In terms of the probability weighting, I think that there is no certainty by which I can make decisions. I don't know for other people, but ultimately I sort of view that there's a spectrum of potential outcomes that can exist in some world in the future. Ultimately, there is only going to be one of those outcomes 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 what the likely outcome can potentially be.

• 29:25Speaker 02

  And sometimes you're wrong and it far outseeds the outcome that you actually thought was most likely. And so therefore, were you wrong in your probability weighting? Or was it a outsized outcome that actually ended up occurring? That existed on the very far end of the distribution scale. 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 split tens when the dealer's showing a six potentially and that could work out for you. Or you could end up holding and staying where you are and that could work out for you. Sometimes you make the right decision based on the information you have with the wrong outcomes.

• 30:10Speaker 02

  Sometimes you make the wrong decision and get the right outcome. One of the best investments in my career was an investment in a company called Braze. And they were called Appway at the time. I remember really haggling with them. It was like 18 months of haggling with them on and off over price about whether or not we would pay 90 posts, 100 posts, 110 posts, 120 posts. Today, it's a $5 billion public company, right? Did any of those things matter? No, they didn't. Like, none of those things would have determined whether or not they were a good investment or not. At the time, I was convinced that the most likely outcome was that it was going to be a 300 or $400 million acquisition by Salesforce or Adobe or someone like that. And so I felt like I had to be really disciplined. On the entry price because it just seemed like such a long tail opportunity that I was

• 30:55Speaker 02

  going to be a public company. Now, clearly, I was wrong there. How did that inform me going forward? Well, it's definitely informed my, if you want to be in the company within the margin, just find a way to get into it and don't get too hung up on the 10 million here, 10 million there. But I can't say that that was the only outcome that I thought could occur, that it was inevitably destined to be a $4 or $5 billion company. I sort of think the world has enough randomness in it that I find comfort in trying to come up with the likelihood that something's going to happen, even if it's false precision.

• 31:25Harry Stebbings?

  Often in the early stage, we hear about ownership sensitivity. I need 10%, I need 15%. When we think about the 3 to 5X requirement with a 10X upside, do you have an ownership requirement, or is it merely a multiple on dollars?

• 31:38Speaker 02

  Multiple on dollars. I mean, obviously, it's easier to own 10%, 15%, 20% plus of a business and have those returns end up generating the 3 to 5X with 10X plus upside. But we've been fortunate enough to be involved in companies like Stripe and Twilio and Snowflake and a bunch of others that have been just really far hit home runs. And so when those ultimately happen, they can far exceed the ability of owning 12% of any individual company. So we really focus on outcomes more than the percentages at our stage. I know our early-stage team spends more time thinking about ownership.

• 32:13Harry Stebbings?

  You mentioned braids being the biggest win. I think you learn a lot from your biggest miss or your biggest mistake. When you think about your biggest miss or mistake, what is it? And how did that change your mindset?

• 32:23Speaker 02

  I think at the growth stage, I have 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? While we were fortunate enough to be an investor in Snowflake at Redpoint, I remember back at Battery, looking at the opportunity and just thinking, the customer calls at the time were kind of raw about the business and how well the cloud was actually working. Amazon and Redshift seemed like such a formidable competitor. Who ever wanted to compete with Amazon on their home turf, which was...

• 33:05Speaker 02

  AWS and what we thought was Redshift and EC2 at the time, like, why would you make that investment? That seems like something that you're jumping into shark-filled waters. 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 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. If we had looked at the founding team and the infrastructure they built, I think we would have looked past the individual customer feedback, a data point here, a data point there, that said, hey, this is still not quite ready for prime time, and instead

• 33:49Speaker 02

  focused further downfield and said, we think in the long term, this is all going to work out, and made the decision to invest. And so that's informed a handful of investments for me. If something just feels like an inevitability, and you might be a little early on the tech or on the market, we're talking months or maybe years, not decades, then it's worth just getting on board if you think the company's going to be the one to execute on it. That's really informed a handful of investments I've made. If you feel like it's inevitable, get on board, because the details can be figured out along the road.

• 34:23Harry Stebbings?

  Have you ever lost faith in a founder, Logan?

• 34:26Speaker 02

  Yes. It's typically been some window of opportunity was missed to execute on the business that I felt like the company could have been. I guess it's one specific instance where this occurred. It felt like it could have been a really, really, really big opportunity, but because of some execution decisions along the way, it didn't ultimately prove out.

• 34:49Harry Stebbings?

  Do you communicate that to the founder? Do you say, Logan, I'm really sorry for these reasons. I actually don't believe that you have what it takes to lead this business anymore.

• 34:57Speaker 02

  I have yet to have that specific conversation with a founder. In the case that I'm thinking about, there was a board member who ended up leading the charge on that conversation. Ultimately, I think the opportunity passed by anyway, and so it was kind of neither here nor there. In this specific situation, inevitably, if I'm afforded the luxury of doing this for a long enough time, I'm sure that's a conversation I'm going to have to have. And that's kind of where it comes down to trust and building relationships with the founders that you work with. I've found that people that at least I like working with are very pragmatic and understanding of themselves. That if I'm seeing it, there's probably a path to them also seeing it as well.

• 35:41Speaker 02

  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. I just don't view that as something that's a core part of the job. I think founders are sort of the lifeblood of what we get to do. Replacing founders, I just don't view as an ethical thing that I want to be a part of. But if there are ways of soft diplomacy of convincing founders that maybe that's the right path through enough data points and conversation. So that's the tact I hope I'll be able to take.

• 36:09Harry Stebbings?

  So I agree with you, but the role of the board is technically, I think, as Brad Feld said on the show, to hire and fire the CEO. 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?

• 36:26Speaker 02

  Yeah, my role as a board member necessarily to hire and fire the CEO exclusively. I think that that's certainly an element and can be a part of the job. But if ever you're going to the votes that are, hey, do you have the power to get something done? With regard to removing the CEO, something else has broken down along the way in the journey and the relationship you built with the founder and the rest of the board. Brad has done this a lot longer than I have. 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. I view my role as earning the right to be a trusted confidant to the CEO.

• 37:07Speaker 02

  CEO and the executive team, I very much view all those words as important, earning the right to be a confidant. 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 employees, for other investors, with someone else at the helm, then I hope to be able to use that soft diplomacy to get it done. I'm sure there'll be a date in which I will need to use my board power to vote against a CEO. I'm thankful that it hasn't happened yet and I certainly don't hope to find myself in that situation anytime soon.

• 37:39Harry Stebbings?

  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?

• 37:47Speaker 02

  The most fun I have regularly on a board right now is with Crossbeam, mostly because I just really like the people around the table. Bob Moore, the CEO is fantastic. Matt Turk is a very good friend. Andy McLaughlin from Unkork led the seed. And then we have a fun group from Andreessen Horowitz is well involved. So I think as a group, we just have a lot of fun together. The best single board member I've worked with, Niraj Agarwal was my mentor at Battery. He was fantastic. Two that I've really appreciated getting to know are Rob Ward from Merit Tech. Just is very similar to Niraj in style. He has a ton of gravitas, is able to handle the soft diplomacy with CEOs in a very tactful and smart way.

• 38:31Speaker 02

  The one that I've internalized the most from and that I just have infinite amounts of respect for is Eric Vishria from Benchmark. Eric and I worked together on the Amplitude board and now we have a new company Acuity MD together. Eric is just A++ as a board member.

• 38:47Harry Stebbings?

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

• 38:52Speaker 02

  I think he has the right level of empathy and passion and he knows the inside out details of the companies he works with. He knows the right altitude to talk to the different entrepreneurs and you just know he genuinely cares. So he's willing to spend as much time as you want as an entrepreneur with you 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 all the things that he's seen in his career as an operator or his career as an investor. I think just his ability to synthesize all that stuff down and speak to people at the right

• 39:35Speaker 02

  level with the right tone is just unlike anything I've really seen before. I've learned a ton from him and wish I could spend as much time as possible kind of learning from the style that he takes to operating with these companies.

• 39:48Harry Stebbings?

  Logan, I want to move into a quick fire. So I say a short statement and then you give me your immediate thoughts. About 60 seconds per one. I'm going to bring in some other stuff here because there's so much that I want to pack in. Ready?

• 39:57Speaker 02

  Do it.

• 39:58Harry Stebbings?

  Favorite book and why? What should I read?

• 40:00Speaker 02

  I absolutely love Team of Rivals about Abraham Lincoln and how he assembled his cabinet. I think there's a lot of applicability to really successful CEOs I've worked with and their ability to have a bunch of different conflicting personalities, styles, opinions, and ultimately synthesize down what is the most insightful decision for, in Lincoln's case, the presidency and the CEOs I've worked with, the business. And so I learned a lot from that book.

• 40:25Harry Stebbings?

  What the fuck is going to happen to crypto?

• 40:28Speaker 02

  I think there's some value to be had in the crypto ecosystem. I don't think it's to the tune of $25 billion 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. Speculation and gambling seems to be a decent enough use case. You throw in NFTs and 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 commensurate 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 the vintages of these crypto funds that we've seen recently.

• 41:04Harry Stebbings?

  Why do B2B marketers suck?

• 41:06Speaker 02

  Because if you cared about marketing and you were really good, you would go into consumer because the budgets are much bigger and you get an opportunity to be much more creative and come up with things like Super Bowl advertising and all that. So if you were really good about marketing in general, you would pick consumer. If you really care about B2B, you'd probably go into sales or product because oftentimes that has much more budget or influence within these organizations. And so. What you're left with with B2B marketing is typically people that fell into it from some way, shape or form. And then there's three different buckets typically of B2B marketers. There's sometimes brand marketing or PR. There's product marketing and then there's demand gen. And ultimately, not all of those things are going to be exactly what you need as a company.

• 41:48Speaker 02

  And so not only are you getting picked over for all the quality people, but then it's also often down selected to specific skillsets that aren't totally transferable. And so you end up just having to pick one of three, but you can't get all three. And so it just ends up being a very limited pool of people that go into it that are talented.

• 42:07Harry Stebbings?

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

• 42:25Speaker 02

  I think it's one of those things that you just need to in-house. Ultimately, every industry is going to be bespoke in terms of your ability to get out there, get reach, get message. And paying a PR firm to go about doing it, one, they're going to have a whole bunch of clients that they're horse trading on who goes where. And two, over time, it's going to benefit you much more to build these 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. Two, what message even kind of resonates? And it gives you a much quicker iterative feedback loop.

• 43:08Speaker 02

  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 funnel. Even if it doesn't work, you're much better in-housing it than throwing it over to someone else and having them give probably not their best performance and trying to get you placement.

• 43:36Harry Stebbings?

  I think this is one massive mistake I always see founders make. I say, this press release is dogshit. Who did it? And they're like, oh, we just gave it to the PR firm. Why was this, oh, I just gave it to the PR firm? If this was a cool piece of product, you wouldn't just say, I just gave it to an outsourced house in wherever. You would do it in touch. You would build it. You would spend time on it. It would be an art. Why is it like, oh, whatever the release? It fucks me off so much.

• 43:57Speaker 02

  It needs to be a core competency of what you're going to do. And ultimately, it's kind of taking a shortcut because you don't think it matters. But if you're going to build an important company, it is going to matter. And so you should only really do stuff that you think are going to be needle movers for you. And I just think PR can be one of them.

• 44:12Harry Stebbings?

  Tell me, what's the hardest element of your role with Redpoint?

• 44:15Speaker 02

  It's just managing the market that we're in today and trying to figure out 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. That requires a level of discipline. It requires a level of ability to win. It requires a level of patience 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.

• 44:59Speaker 02

  And instead, we're going to wait for the great ones to come across our desk.

• 45:02Harry Stebbings?

  What crossover fund have you been most impressed by?

• 45:05Speaker 02

  If I were to say pure crossover fund, I've really admired what the folks at COTU have done in terms of building their brand and awareness at the late-stage growth market. I think that they've done a lot of amazing stuff. I think in pure growth, I just have infinite amounts of respect for Sequoia's Growth Fund, the folks over at Merit Tech and the guys over at Iconic. All those groups do a really good job picking and I want to beat all of them every single day. And I wish them very poorly, but I have a lot of respect for what they're doing and a lot of friends at those places. I know when we're going head to head in an opportunity, you can't go wrong if a founder picks to work with them. And they all do a very good job of picking to be in great companies.

• 45:47Speaker 02

  And so respect for the game on the field we play against all those firms.

• 45:51Harry Stebbings?

  Which crossover funds most in trouble?

• 45:53Speaker 02

  I think the crossover firms that are most in trouble are the ones that got into the market hot and heavy over the last two years and didn't necessarily have the history of delivering outsized returns over a long period of time at their existing shop. And so I think that there's a few that you can think of that people spun out and maybe started new funds or went really, really big over the course of the last two years and brought in a whole bunch of new LPs. And I think anyone that either doesn't have their existing track record of the last, whatever, 10 years attached to the name of their existing firm, or anyone that scaled well beyond what they had in the prior five years in the last two years, I think anyone that fits that

• 46:36Speaker 02

  bill is probably going to have a little bit of a reckoning here right now. I'm surprised, honestly, we haven't seen more firms move to the family office model. I think it's kind of a function of how much money exists in the ecosystem right now from all the different pension plans, but all the different foreign sovereign wealth entities out there that you haven't seen some of these people have to close up shop and say, hey, we're just going to manage our own money going forward. But I keep waiting for that to happen. I think it's bound to happen at some point here. Who's the most underrated angel, you think? The one that I just have infinite amounts of respect for is Zach Weinberg and Nat Turner and what they do over at Operators. It's their own money. They're very long oriented and they have such a pragmatism by which they approach investing

• 47:21Speaker 02

  and the types of people that they want to work with. Whenever I talk to them about a potential opportunity, it's not just a something about a big market size or something about someone else investing. It's usually something very specific about the individual entrepreneur and something very specific about their insight. Zach had a great insight that I've kind of internalized is that the best founders can tell a very high level story about their business, but also can drill down very deep into all the nitty gritty specifics about their opportunity, about their company, all of that. And I think That type of insight, I just get out of him all the time and it really amazes me that he's able to take some very specific insights and bring them to a part of the market

• 48:03Speaker 02

  that I just view as such a black box and such an art and to know that there are people like that, like him out there, that really have these set of core principles that they operate with that lead to the investments, I just think is really impressive for me to see.

• 48:17Harry Stebbings?

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

• 48:20Speaker 02

  I haven't yet. Now, we've been in a eight-year bull run since I've been investing. I was on a board of a company that had to do a full recap. I've thought about this. I give the founder a lot of credit because actually after the recap, he was able to turn it into a really successful outcome for all the people that participated in the recap. The thesis that was wrong at the point of the original investment was ultimately, it was a little too beholden to 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. I wonder at the point of investment if that was actually one of the real internalized

• 49:01Speaker 02

  probabilities that could happen, or if that was something that snuck up on the investment team over time. What I'll always tell our team internally is, I really don't care if something goes wrong in an individual investment, 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 and do all the work so that we understand that, so that we're at least not surprised by things when they ultimately do hit bumps along the way.

• 49:32Harry Stebbings?

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

• 49:38Speaker 02

  QDMD was the most recent investment that I said yes to. The seed slash Series A was done by Eric Vishria from Benchmark. I did what was called the Series A, was more like a Series B. What got me most excited about it was, it was in this underserved market that had an opportunity that the founders recognized to bring tech and specifically CRM and targeting, so they operate within the medical device space. And so what they're building is something akin to ZoomInfo plus Salesforce for med devices. And these founders had that unique insight that this actually maybe wasn't a big enough market 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 opportunity.

• 50:22Speaker 02

  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. The CEO, Mike, was a swimmer and you can just kind of tell, 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 tireless nature by which he works. And so it was a big market, a great founding team. And honestly, I think that there's not going to be a ton of venture backed competition going into this space. And so I think they have the right to win and the right to earn a lot

• 51:05Speaker 02

  of these customers' trust and ultimately turn this into a really big vertical market, à la Viva, à la Service Titan, à la Procore and a bunch of those other successful ones that we've seen in the public markets. So a really exciting opportunity that yeah, we're really fortunate to work with.

• 51:20Harry Stebbings?

  Logan, I've loved doing this. I so appreciate you not reading the schedule very much before, otherwise you'd be totally fucked. I can't thank you enough. This has been so much fun. So huge thanks, my friend.

• 51:30Speaker 02

  Awesome. Thank you for having me. We'll do it again in another six years or so.

• 51:35Harry Stebbings?

  I just love doing that with Logan. Such a free and natural discussion. Huge thank you to him for giving up the time to be on the show today. As always, I so appreciate all your support for the show, but before we leave you today, if you are a venture capitalist or corporate strategist, I want to tell you about Tegus. Tegus is the only company in the world that aggregates qualitative information on private companies from seed stage to pre-IPO. With Tegus, you can access other VCs and founders' expert call transcripts from previous rounds to help source fast growing companies, create compelling emails to get a founder's response and diligence companies when a round is moving fast. I use it personally and I think it's insanely brilliant. Tegus is also providing the most flexible and highest quality way to run your own expert calls.

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• 53:01Harry Stebbings?

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• 53:44Harry Stebbings?

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• 54:04Harry Stebbings?

  As always, I so appreciate all your support and I cannot wait to bring you a fantastic set of episodes this week with one on Wednesday and one on Friday.