The Secrets of Venture Capital With Peter Livingston of Unpopular Ventures

David Melamed 7:03

Again, I assume that there’s some signaling. On the other side, this or I should be asked about, you know, bad investments. But were there ever in an opportunity that you saw that you’re like, This is the worst idea ever, I better invest. And then it turns out to actually be the worst idea ever.

Peter Livingston 7:24

Of course, I mean, that’s venture, I mean, so. So VC as a whole, you have a ton of losers. I mean, it’s just part of the game. But the thing is, in this game, you only lose one extra money when you lose, and you could potentially make 1000, extra 10,000 times your money when you win. And so so it always sucks to lose money. I hate it when it happens. But I try to let go of it. Because, yeah, it’s like, if it’s 50/50, if it works out, or even 25 chance of a win, and 75% of it doesn’t. If it wins, it’s 10 bucks or more, you should always make those investments. So sure, I have failures, try to learn from them. But the truth is, it’s really hard to predict. And you just got to get out there and try to make a lot of investments and hope some of them are those mega successes.

David Melamed 8:15

Got it. So something interesting, I noticed, you know, when you talked about these companies, you talked about their ideas, but when you talked about investing, you talked about smart founders. So like the Instagram and DoorDash examples, were, were those people that looking back, regardless of the idea if you had that kind of your risk that you have today about what type of founder you’re looking for what qualities, did you see that in them? Or were some of those complete surprises?

Peter Livingston 8:46

No, I should have seen it. Very smart guys, very driven. You know, so the, you know, the Instagram founder, for instance, had a ton of phenomenal experience. He had been through multiple startups, he had been a product manager at Google. When I knew him in college, like he was clearly a very smart guy. And, and same thing with the DoorDash founders. They were very smart and class very driven. And they were just people that you should bet on that. I think that kind of the way that I define what I look for in founders now is just a track record of success. Have they done things in the past where they were successful or did remarkable things that gives you at least some amount of confidence that they’re likely to succeed again, in the future? Or in anything they do? And when that’s the case, I base I try not to overthink it. In fact, right now, I’m at this point where any smart friend that I know who’s starting a company where I just think that they’ve been around the block and are pretty smart. I always invest even if the idea is that or even if I don’t get the idea I’m getting because these companies always pivot. Even if the initial idea doesn’t work. They often you know, the smartest most driven people often find something that does so When you’re investing at the beginning, it’s all about now

David Melamed 10:02

are most of the investments you’re making pre revenue, or fairly early, early on? Or what what makes a company ready for, you know, unpopular to step in and participate in around?

Peter Livingston 10:19

Yeah, so it depends. So we certainly invest pre revenue in a lot of companies. And when we, when we invest super early, it’s usually because the founder does have a remarkable track record of success. If there isn’t as much of that signal, or we’re not sure, they’re kind of operating in a space where they can find that product market fit, then we do like to wait a little bit more. So we do often invest, also went when there is some traction, and we’re happy to pay a higher valuation. I think that probably two thirds of our investments are what I’d call right in the middle seed stage. So like, they have some amount of traction, there’s some early evidence that they have a product market fit or something’s working. So we do usually look for that traction, but then it’s probably like 50%, or around or maybe 50 60%. About a quarter to maybe a third are that super early, where it’s just an idea, but it’s a workable founder and founding team. And then we do some that’s later, later, too. So we’ll do series A or Series B, but it’s it’s a real place.

David Melamed 11:24

Are there any investments or founders that you’re really excited about? Because he feels like, you know, this is just these people are just that no matter what they’re going to do, they’re just going to succeed? Is there anybody or any, any, any companies, you’re able to talk about that you just, you know, tomorrow, they’re going to be the, you know, the story that the people that didn’t invest are going to talk about how they are buddies from college, I missed that opportunity.

Peter Livingston 11:51

Well, so So first, I, we love all of our children equally, they’re all great, we really want them all to succeed, I wish I could talk about all of them, our portfolio is pretty big now, where we’ve invested in over 150, it might actually be over 160 or 170. Companies. Now, I haven’t looked at the exact number lately. But we do. It’s not just me, it’s a team of five, we’re investing very actively, big portfolio, and we have a lot of companies that are doing great. And we I feel incredibly lucky that they allowed us to participate in their journey. So so thank you to all of our portfolio founders for letting us invest. You know, if you want to zero in on one tie, you know, when you’re when you’re investing in startups, you’re going with a long time horizon, you expect it to take 10 or more years. And oftentimes, the best investments are quiet for many years, it’s not clear they’re gonna be successful. So it might be three or four years after investment, or they’re still figuring things out. And then they hit the group and then are wildly grow like crazy, wildly successful later. But then sometimes also, you get these early winners, so they just take off right away. And so given that we’re early in this process, we don’t know who the biggest long term winners will be. But we do have a few that are really breaking out quickly. And so one that I could talk about in that vein is a company called Jeeves. It’s a they’re building a global business bank. They started as a corporate credit card for international international startups. So kind of like a bricks or ramp, but focused on initially Latin American startups, but now a lot of other countries around the world. Last I heard they’re in 26 countries on three continents. And they’ve now expanded beyond just corporate credit cards to full expense management. And now they’re doing revenue based financing. And they’re building a whole suite of products. They were there, their vision has to be the global cross border business bank. 

David Melamed 13:43

So I didn’t I didn’t catch the name cut out for yes. Sorry,

Peter Livingston 13:47

the company is called Jeeves, J E E V E S. And we just got incredibly lucky to so we were the first investor after Y Combinator was technically the first investor. And then while they were in Y Combinator, we were the first you know, actual investor aside from yc. We saw because the founder was a good friend of mine from business school. And they also were building a great product, yet he had a great experience. And they also had some early traction with the customer sales were growing fast. And so we were able to invest quite a bit and $10 million valuation initially, and they’ve just been a rocket ship, that is public news, I can talk about it. They raised six months after we invested on 10 Andreessen Horowitz came in with a lot more money at a much higher valuation. And then just in the last month or two, they’d raised another round from CRV and Andreessen Horowitz at a $500 million round from 10 to 500. And about a year. So it’s at least on paper, it’s doing great and the XP attraction is there, the executions there that their numbers are phenomenal, and they’re growing like crazy. So if you want to judge today, that seems to be our first real breakout winner. Oh, there are a lot of They’re doing great.

David Melamed 15:01

That’s amazing. So was the fact that they were Y Combinator important signal early on, or what, you know, do recall your initial discussions with them. What made you feel like this was, you know, a good? A good bet?

Peter Livingston 15:16

Yeah, well, so I don’t know that they needed Y Combinator. But But YC does help. Both YC picks great people, and great companies that tend to be successful. But then the coaching that they give, and the network that they give is really helpful as well. In the case of this company, they’re selling to other startups, particularly global startups, and yc, plugs into a huge network of global startups. So it’s a good way to get customers. The, you know, the founder, had a great background. He had previously co founded another company, that they raised a good amount of money from Great Investors grew it to 45 million arr. And the company’s doing great. So you know, startup experience, it’s not always required. But I do find that founders that have been part of the startup before they hit the ground running much more quickly in their next one. And so just as a signal of how likely they are to be successful in the current venture that we’re investing in, seeing that they’ve kind of been around the block a couple of times in startups finding that product market fit growing yet. It gives us a lot more confidence that they’re likely to succeed again.

David Melamed 16:27

Yeah, that reminds me, I think I read somewhere once upon a time that one of the things YC always used to push early on is showing weak growth week over week, for sure, when you’re in the program, so that hit the ground running piece seems to be really important. You know, just speeding up that learning cycle.

Peter Livingston 16:48

So it’s exactly right. No, I mean, the best startups move fast and track their metrics, super granularly. So like, I see a lot of startups out there, where it’s like, they’re presenting their growth year over a year. And when I see them and often meet with these companies and say, you’re a startup, you’re supposed to be moving lightning fast. Why are you showing? Why are you tracking and reporting numbers? On a year over year basis, you should be doing at least month of a month, if not week over week, and month and trying to improve it every every week, every month, those wants to kick us because they they’re trying to be quick and move fast and learn as quickly as possible. And I think why see it helps a lot with getting in that mindset.

David Melamed 17:35

Yeah, I’m sure the cohort also creates that kind of peer pressure. It’s I think they stumbled upon a really brilliant insight that maybe Napoleon Hill talked about with the mastermind. But I think that cohort idea is That’s my feeling. Sometimes product market fit is not this like a mate. Like I look at taking micro acquire. For example, if you see that see them right now there. They feel like a rocket ship to me what I see them doing. And to me, the idea was just like, I’m not quite sure what they did that was so special or so unique. That was different than all the other marketplaces and forums and places that you could buy, you know, micro SaaS companies and startups. And I think that one of the things that Andrew hit on with that startup is maybe the anonymous nature of the seller, where a seller can kind of like on AngelList to you have syndicates and you have to be invited in before they even I mean, that’s probably because of compliance reasons around marketing securities, but that it creates a certain I don’t know I just I am certain comfortability people are able to share more information, be more transparent when the people they’re sharing with are carefully vetted. And I feel like sometimes, you know, like with YC, I think my guess is just the cohort was a smart enough insight that almost everything else was was irrelevant. I feel like sometimes you just have these startups. I don’t know if Jeeves is hitting that with what they’re doing right now that they have that traction, but sounds like an amazing company. So that’s very cool. I just think you mentioned you mentioned earlier, you know, I have your your quarterly update from November open in a tab and you mentioned you you didn’t recall how many investments you’ve made so far. It’s actually more than you you recalled, you have a little graphic on our graph table that shows you you only started in 2019 with 24 investments or 22 companies, and you’re at 193 investments in 150 companies. So I guess that’s 43 that you’ve done follow on invest Since an existing companies, when you do those follow ons are those also offered to all your LPs? Okay, very cool. 

Peter Livingston 20:12

So like it’s really all it’s it’s a delicate situation. So sometimes our follow on allocation will be too small. And so we do first offer that to the people that invested before. And also our fund LPS get priority for that. But if we have additional allocation beyond that, then it goes to everybody else.

David Melamed 20:30

So yeah, that’s something I’m very curious about it. It feels like there’s so much money in the market right now. And maybe it’s just because I joined a ridiculous amount of syndicates on AngelList. When I look at my No, I mean, I’m, I think I’m in like 100, or some crazy number. And I’m also I must have made 150 investments by now. Some of them really small bats just because I wanted to, I want to really learn everything going on. And one of the things I loved about about your investments, and I’ve only done a few small, small ones, were you’re very thorough, and the information that you write and that you share, and I don’t know if that’s something you picked up in business school, or you just put in the hard work and other people are willing to do it. Your your quarterly updates are I mean, you have to want to read it and read it because there’s so much information, which is like a dream come true for me, because I’m literally part of the My goal here is just to learn, I love learning new things. And it’s fascinating seeing how all this plays out, I can’t wait to fast forward a year to actually see what happens with a lot of these these positions. But I’m so I’m curious. You know, I don’t see you overselling with your offerings, I always sometimes actually even see messages for the same offering from two or three different syndicates. And I even know this once or twice with different terms. So as an LP, what I’ll look for typically is what their investment is, in, um, you know, if they’re only putting in 1000, and they have a minimum of 2500. That, to me, that’s a signaling problem. But when their investments they’re at 20,000, or something like that, and then you know, you can invest 2000 or more, you know, to me that says that they really buy into this, I one thing I’m really afraid of, because I don’t understand the fee structures super well, I understand cary, but I you know, this podcast called fixing incentives, I everything I do about marketing, it’s about really just understanding people and what drives their behavior. So I you know, I’m very curious why you’ve been able, like, you’ve been a little unpopular in the way that you’re not selling overselling these deals with, you know, just really pushing FOMO and pushing, you know, Elon Musk’s cousins, twin brothers, you know, a lead investor, you’re not pushing this like narrative that other people are in said, you’re providing, like, really thorough information. At least that’s what I’ve noticed on the deals that I’ve seen, is there something that drives that within you, or how you approach these investments that that allows you to do that or that inspires you to do that?

Peter Livingston 23:22

Oh, gosh, so Well, thanks for saying that. And you cut, you touched on a lot of different things just now. And I want to, I want to answer a few different things that you brought up. The first thing that I want to go back? And answer is you mentioned that you’ve done 100 150 investments on AngelList. And my honest opinion is that you’re already in a better position than the majority of people that try angel investing. One of the biggest mistakes that people make when they first started angel investing is that, well, they probably don’t have much deal flow. Yeah. So the first company that comes along, that they see, they get super excited about and plunk a third of their money into it, or a third of their, their, their angel allocated money to and, and they just don’t build it big enough portfolio. And so kind of the two ways that I see people lose money in Angel Investing is one, they don’t build too big. They don’t build a big enough portfolio. And two, they they deploy it all at once. And but specifically on this first, like, I don’t know anybody, I haven’t come across anybody who built a large portfolio of at least 50 investments. And was understood that the timeframe understood was a while I don’t know anyone who did that and lost money in ancient history. Certainly, there’s a spectrum of how good the outcomes are, but the very fact that you went in putting small amounts, you built a big portfolio, sure, a lot of them are gonna fail. But in aggregate, I feel extremely confident that you’re going to end up with with decent returns and you’re going to get at least your money back and good return somehow. It’s great that you build a big portfolio. That’s what I’m trying to say. Thanks to so to your point. About the overselling the height, all this stuff, it’s a really tricky issue. What makes it tricky is that it works on people. So I probably before he joined, I experimented with that in the past, it’s actually crazy. So you’ve probably noticed that on AngelList. People are always talking about how oversubscribed they are to x oversubscribed or have subscribed or this or that. And they’re always the reason they’re doing that is that when you send out a message on AngelList, with the word oversubscribed in the title, you get a bunch more money. It’s like it sucks. But it is clearly some kind of hack that hits people psychologically, with scarcity or social proof or some something about this, that causes more money to put money more into those deals. I hate that it works that way. I wish it didn’t. But the reason all those people are doing this is that it works on people. I think it’s kind of like how nobody likes to think advertising works on them. But clearly advertisers spend a lot of money because it says clearly working on on people. Even though people don’t like to believe it. It works. But with with me and our team, we’ve talked about it and we just think it’s it’s gross, it feels like people are lying. In fact, somebody syndicates will go and get a half million dollar allocation. But then they’ll that they’ll agree with the founder, we’re gonna do half a million, but then they’ll put it up as 100k in the syndicate. And then once they fill that 100k They go in, they’re like, oh my god, we’re so oversubscribed. Like, oh, like I went back to founder for more and Oh, luckily he gave us more of thank God, now we’re at a coordinate or it’ll be like, Okay, now we have 150k They feel that man, they sent another email. They’re like, Oh, my gosh, we’re so oversubscribed again. And it’s all a lie. They had a half million dollar allocation. They were never oversubscribed. They’re merely hacking people’s psychology. And so anyway, the behavior, in our opinion, is gross and unethical. And we’ve decided to stop doing it. Probably to our detriment, like we we often don’t raise as much money as if we had been overhyping these things and talking about oversubscribed we are. But we we do really care about our reputation. We’re up here in front of 2700 LPS in our case, and we want we want to do everything we can to earn the respect of everybody. We think that way. That’s why we behave that way. pause there and see if you have any questions. And then I could answer another thing that you hit on?

David Melamed 27:28

Sure. Yes. So I think I have so many around that, you know, this, this goes to every deal I see on AngelList has this big warning about confidentiality. I know that there is one company. I want to say it’s called Travis, probably getting it wrong. Vinson get Vincent or something with Vincent is trying to be an aggregator of alternative investments, but with the need for confidentiality and the speed of transaction, you know, for me to invest? I’m literally checking five boxes and hitting invest. What, you know, is this something that AngelList or other places should be fixing? Is there. Like what would be like how would you solve that broken incentive or that problem where the the LPS don’t really have the time to do that same type of due diligence that they’re hoping the syndicates are doing. And more importantly, if there’s fees that they make up front, they might be incentivized to just bring up as long as there’s a lead investor, and they could get an allocation just floated out and, you know, partner with their buddies and, you know, across Angeles for their allocations and just copy and paste, you know, some things that they have, and just, you know, push it out, like, what do you think? I mean, is this pushing people off platform to do private deals with a sure is it like, like, what do you see? I’m curious, like from the, the LP side, whether you think is is the right way to fix some of those broken incentives?

Peter Livingston 29:22

Absolutely. Well, I love that you’re so interested in focused on incentives, and it’s something that I’m too I believe, incentives make the world go round. And I spend a lot of time thinking about them. So it’s, I think it’s really cool that you’re similarly Well, nerd made me maybe nerdy about it in the same way that I am. So I’ve actually thought that’ll get a lot on AngelList. So, to put it in context, so on AngelList there is no upfront fee that any lead receives At least in syndicates. So when you invest in a syndicate, the lead does not get any cash right away. So that’s good. At least they’re not incentivized just put up a lot of crap too much. But there is actually still a broken incentive in how this is set up. So it’s a problem, a potential incentive problem is that a lead could potentially put up a ton of deals, to the absolute minimum, do one cave themselves, put up everything that they see, raise a lot of money on each one. And they could potentially lose money in aggregate to their LPs. But if they have one of those deals, that does pretty well and exits for a multiple, that we can make money, even though on average, all their investors will lose. And so that is a broken incentive where, because of that, a lot of leads put up just tons and tons of crap that they haven’t diligence. Because they know they’ll probably get the money. And even if they lose on most of them, hey, at least probably a couple of work. And they get this free optionality where they’ll probably get some cash out at the expense of their investors. So it’s something that people have complained about in the past. And it’s something that I think is dangerous and concerning. And, and I’ve actually tried to fix it in the way that we behave. And the way that we have tried to fix it is that we publish our numbers on a quarterly basis, and show both the detail portfolio of like, what we’ve invested in how it’s all doing. And then also the aggregate numbers with the intense that, hey, sure, we could go and try to make money at the expense of our investors. But that’s not what we’re trying to do. We’re trying to make money for everyone. And when our investors win, that’s when we want to win too. And so by holding ourselves accountable and reporting on our metrics, and in fact, on our own team, we have our own dashboard, where we show each partner’s metrics by year. And the expectation is that every partner should be doing deals in a way so that they produce an aggregate net positive return for the investors. Got it? It’s not perfect, but at least by holding ourselves accountable and trying to produce good returns, and, and not leading into that, that potentially misaligned syndicate instead, we’re trying to do we’re trying to do better. And luckily, so far

David Melamed 32:23

do you find that? Investing enrolling funds? Or I think you have preferred access funds, does that help fix some of that incentive a little bit, because at least you’re participating in multiple deals?

Peter Livingston 32:39

Yes, and no. With the funds. So most rolling funds charge a management fee, and the management fee, most of it actually gets paid out upfront. So if you if you do invest in rolling funds, those leads actually do get cash out upfront. So they are incentivized to raise as much money as they can, and they’re going to make money even if they might. Having said that, in terms of the investing in the portfolio level, they don’t get into their carry until they return the whole portfolio. So at least they can’t make money off of just one deal. It does well, even if all their investments, they do have to return the portfolio to get to here

David Melamed 33:17

Got it. But I guess if they’re getting that money up front it, you know, it’s a different broken incentive, but it doesn’t solve a problem completely. So I guess over time, there’s a certain amount of trust that people can build up. I guess that that’s that’s one solution here, but I, it’s interesting.

Peter Livingston 33:35

So you’re actually I realized I meant to answer that as well. You’re exactly right, that the LPs are in a position where they have to trust Billy. It’s hard to tell how much diligence they’ve done, other than what they’ve written? It’s hard to know. Yeah. If you invest behind leads on AngelList. A lot of it is basically trusting leads. And so with that, as well, we’ve been trying to build our track or republish our numbers report regularly, with the intent of saying look like we’re doing the best we can, we’re not always right. We do lose money. But on our route, we do well, and we think that we are worth trusting. And certainly it’s up to the LPS. LPS would prefer to best direct, they can go and try to do that. And so it really it’s an individual decision on it.

David Melamed 34:33

Um, so you I do have one other question I want to cover but you you mentioned that I asked the question earlier that have a different point that you want to address too. So what would you rather do first?

Peter Livingston 34:42

You go ahead. I think I think I got most of the things that I thought were worth addressing and Good morning, sir.

David Melamed 34:49

Okay, so um, I there is one company I participated in that you are working with. I don’t know if I’m allowed Talk about it or not? You can say me. But it’s, it’s because the topic I care about, which is frame fertility.

Peter Livingston 35:08

Oh, yeah, no.

David Melamed 35:11

So I, I’m married for 11 and a half years now we don’t have kids, we went through the infertility journey. At this stage, I’m comfortable talking about it publicly, it took a long time, I, I understand the emotional stress and pain that goes through it goes deep to your core. But in our case, it was it was male factor. So it’s an issue with me, not my wife, it took us three years, three years of doctors to even start testing the the male side, even though 50% of them have explained infertility as male factor. So, you know, I think I don’t recall everything you guys wrote about for infertility, and I’m not trying to get into fertility discussion. But anytime I see a startup addressing the issue, especially around early information, that helps you understand because, you know, in my case, what was that I’m dealing with is it has impacted my life in any way, shape, or form, medically or anything like until we were ready to start trying to have kids. So I’m very curious about either about frame fertility, what you liked about their do what they’re doing, or, or I don’t know how much you could share about what they are doing and what progress they’re making. But it’s, you know, it’s, this is one of those markets, that the data might not even be there to let you know how large it is, even though it’s, I don’t know, one eight couples experience some sort of, and the numbers probably even bigger than that, when you start getting into secondary, you know, people that have one kid, and then you know, go eight, nine years, and you know, treatments are insanely expensive, and doctors are and half of the time they don’t know what’s going on. So I’m curious about that, about that company in that investment? Are you kind of bullish on them? Do you feel like they’re doing real, you know, I love to see what they’re actually doing to know if they’re, they’re gonna actually put a dent in making life easier for people with this, like very private, very personal and very painful topic.

Peter Livingston 37:21

Happy to share. So first, I’m very sorry to hear about about your challenges on this front yourself, that must be incredibly hard to go through, especially with how opaque system is, and that is crazy that you went through three years of trying to figure this out. And they didn’t even look at you for three years, which is really the system is broken. I’m so sorry, you went through that. I appreciate that. Congratulations on your on your 11 years of marriage. That’s fantastic. So this one is actually easy to talk about. And we want to talk about anything confidential. So So there are a few kind of signals in that exists in startups where I almost just always auto invest, like, like, it doesn’t matter what the so being completely transparent. I know very little about the fertility market, it’s not a space I have expertise in, in this case, is primarily a judge of the team and the signals around. So the first is that I’d known the founder for a long time, or one of the two founders. So Cory has no life team. Cory I’ve known since 2007. And we actually spent a lot of time together and Cisco knew him then knew he was super smart, very driven. And, and, and then since then, he’s been very successful in his career. So he, you know, I don’t only invest in Harvard and Stanford graduates, but it’s certainly nice. You know, he went to Harvard Business School, you know, clearly smart guy to, to, to have gone through that. Just to be clear, with all founders, you don’t have to go to Harvard for me to invest in you. But sure, it’s a marker of past success. But then, in addition to that, he went through multiple startups, very successfully. So he was at synapse, and I’m not going to remember all them. But basically, he had very specific expertise in health tech startups, and so did his wife in separate health tech startups. And then the clincher for me was that they left to start this new company, and two of their former bosses that founders or CEOs of the prior Health Tech Stars that they worked at, were angel investing in this company. And, you know, when I think about checking references, I really think there’s no higher reference, then your former boss investment, particularly when they have expertise in what you’re trying to do. And so that right there, literally, that’s all I needed to know to say, I want to invest. And I don’t know if the ideal will work. I don’t know. You know, we will. I don’t know how big the market is. But I think that if there are people like that with that kind of experience, and all these people who have worked closely with them who believe in them so much. Even if this initial idea isn’t exactly right, they’re gonna find success. So it was a bet that I thought was where

David Melamed 40:09

the market is massive except for it’s a problem that people don’t think that they have until they have it. So if part of the goal is early intervention or early access to information. And I don’t know exactly what they’re building, I wasn’t sure if it was more behavioral health tech that was, I don’t know, I mean, I don’t know if you’re able to share anything about what they’re actually the current iteration that they’re working on is, but 

Peter Livingston 40:38

it’s well, so actually, that that is stuff that is more confidential. And the fact they didn’t want all that information up on AngelList. But in general, it’s a digital fertility advisor, they collect data from a whole bunch of different things, but the questionnaire tests you do, they aggregate a ton of information that allows them to basically judge how fertile you are likely to be probabilistically. And that it can then also recommend actions that you can take to increase your likelihood of being able to actually go.

David Melamed 41:08

So I could just address that point you just mentioned, the first probably nine to 12 months of fertility, treatment, or when you start going to a doctor, when you start realizing there’s a problem is almost all around timing. So that’s the first their first attempt is because I think the numbers something like 40, or 50% of infertility is actually unexplained. They actually don’t know why it’s happening. And in many of those cases, it is as simple as just, you know, the stars aligning, um, so if that’s what they’re covering that first, that first year and that unexplained, you know, at least with that one point you raised about them. About that, yeah, just, you know, collecting information and give you good information. That is it’s actually clinically what they do right now. And it’s, it’s a pain, because the way they do that is you’re you’re going to a doctor early in the morning, you’re drawing blood, they’re doing ultrasounds or whatever else, it’s kind of annoying and invasive, and uncomfortable. And it’s, it’s a challenge. The My only advice to that sector is anybody approaching that market should recognize that, while couples go through it together, they also go through a very private, personal, individual journey. So it’s important to recognize that what I experienced is going to be different, what my wife experienced, and my perceptions of it are going to be limited to me, even though the actual challenge is also together. Um, so that’s just just an insight there. But very interesting, you know, obviously, having that in the portfolio. I’m really happy about participating. You know, just I thank you for joining us. Yeah. And I look forward to more opportunities, and the seeing updates on that over time. My, I guess I like to wrap up with with a question. And my number one question I really have for you is who, if you could just give me one second, I want to expand this because I have it written down. But who are some colleagues or other people in the industry that you admire? Or that you really look up to? Or that you feel like are doing things? You know, really well? In the angel investing space?

Peter Livingston 43:29

Hmm, good question. already doing things. Well.

David Melamed 43:39

Who do you admire?

Peter Livingston 43:42

Yeah, well, I mean, I do read a lot about kind of some of the VC greats or I read blogs. So read Fred Wilson’s blog very religiously. He’s not an angel. He’s a very established VC. I. Yeah, I

David Melamed 43:54


Peter Livingston 43:55

I love his transparency. Absolutely. I read him a lot. I read all of Sam Altman’s blog posts. They’re, they’re less frequent. You know, Peter Thiel is a controversial figure. But I really think everything he says is super thought provoking. So I love watching him when he talks and reading everything that he says. Reading Scott Kupor’s book right now Secrets of Sand Hill Road, and I think it’s been very good, very thoughtful and educational. I know this doesn’t answer your question. Quite Exactly. In terms of angels. These are all basically VCs. I mean, yeah, I guess I’ll leave. I’ll leave my question there. Those are the people that I read the most respect and then and then I spent a lot of time on VC Twitter as well. Just following kind of the latest happenings. They’re talking about,

David Melamed 44:53

is there anybody specifically that you think is worth following besides her following you and I’m popular ventures

Peter Livingston 45:01

Hmm. Not really to be honest, nobody’s coming to mind. I’m sorry to say I wish I could. Sorry, I don’t have any one very specific. But if they’re not following this person in Britain in aggregate, it’s pretty, pretty interesting.

David Melamed 45:17

I mean, those are great choices. I mean, Fred Wilson is just amazing. Although I remember, I wonder how he feels about these syndicate investments. Because I remember at a post, probably 2014 2015, I’m an event. He was really upset about these companies, these VC funds raising $500 million, are these huge funds. He said it was causing all sorts of, I guess, problems that, you know, they were paying crazy valuations. So they couldn’t get access to the right deals, or he just he felt like NGOs are irresponsible. So I wonder how he if he thinks this is helping the market, you know, obviously, LPs in the syndicate can help be early customers, they can help grow company. They can, you know, help with specific asks from founders. But I be I don’t recall if he ever wrote anything about it. I’d be curious as thoughts on the topic. But Fred’s amazing and Sam Altman also, I’ve never, I can’t think of anything I’ve ever seen, like videos of him, or tweets or blog posts that wasn’t deeply insightful. And the other is beer kill. And Scott, before I haven’t followed their stuff as closely, although I probably should. That’s very interesting. And then I guess, to wrap up, Where can someone find you, if they’re both a founder that, you know, has the art? You know, is there a way to reach you? And also, if someone’s interested in being an LP, um, what would be the best ways to get ahold of you or define you?

Peter Livingston 46:55

Yeah, you can find us at That’s that routes straight to our main webpage, which is on AngelList. In terms of founders approaching, it’s like me. So we do. I know, this is kind of a stereotypical old stodgy VC thing. But we do rely heavily on warm intros, or I, in particular, some of my partner’s look at a lot more cold stuff. But we do tend to be inundated with cold emails, I probably get at least 30 a day. And it’s really hard for me to kind of look through all of them and figure out what is worth spending time on. And so I actually rely heavily on warm intros. And the best warm intro you can get is from one of our portfolio CEOs. I always read the emails from from our portfolio founders, and CEOs. And, and we have a lot of the way Yeah, we have over 150 companies we’ve invested, you’re right, that we’ve done over 193 investments, we’ve kind of follow up. You know, the warm intro thing, in a way, it’s kind of like a test of a founders hustle, can they kind of figure out how to get to somebody that that make the case to them, and convince them to make the intro onto who they’re trying to get to. So anyway, I find referrals from our portfolios to be very helpful. And I take a lot like almost all of those those meetings when when our portfolio founders and CEOs who for companies anyway, for LPS you can find us on unpopularVC. And for founders who are looking for funding from us. The best way is to try to try to get it through one of our portfolio founders or an LP listen to her.

David Melamed 48:29

I appreciate that. Very cool. So you know, I was talking you were talking today with either Peter Livingston from Unpopular Ventures and I’m David Melamed, the host of Fixing Incentives Podcast and until next time, have great day.

Outro 48:46

Thanks for listening to the Fixing Incentives Podcast. We’ll see you again next time and be sure to click Subscribe to get future episodes.

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About David Melamed

David Melamed is the Founder of Tenfold Traffic, a search and content marketing agency with over $50,000,000 of paid search experience and battle tested results in content development, premium content promotion and distribution, Link Profile Analysis, Multinational/Multilingual PPC and SEO, and Direct Response Copywriting.

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