Matt Mazzeo (pt. 2) | Product Hunt LIVE

You can't get much shorter than that. I like it though.

At the end, he does it in like 10 minutes, at the end he's like, "$40." I was like, "What?" I could have done this myself.

By the way, that's my new startup. You come over to my house, I will do that for you, $40 a pop.

Absolutely.

I'll keep it looking fresh like that.

And then we'll play the arcade. How's the arcade?

I'll show you. This is my house, by the way, everybody. Hi, my name's Matt Mazzeo. This is officially half of the Lowercase office. We don't have office space, we never really had office space, so Jackson, who's the newest member of the Lowercase posse, literally works at this kitchen table, which is kind of a mess. Hold on a second, I'll show you around.

Yeah, please give us a tour.

Oh, Jessica is here at the house. No, she's gonna be upset, big mess. I'm showing them the arcade. So we've been building this arcade because we're big nerds. Almost done, as you can see. It plays literally every old-school arcade game you've ever wanted to play, 'cause I'm a big kid. Also, just ordered the HTC Vive, which is super exciting, because we built a computer to run all the VR stuff the other day. Oculus coming in a couple months, and the HTC Vive coming in a couple months.

Matt Mazzeo, I got a question for you. First off, this is Product Hunt Live. Matt Mazzeo, lowercase capital, welcome to Product Hunt Live. Thank you for being here again. Now, everyone's dying to know, how are you both a baller and a nerd? How are you both beautiful and like really geeky? You know, how do you—

The nerds shall inherit the earth, man. That's what happens. Say it again, say it again. The nerds shall inherit the earth. It's the truth. I don't know, man. I've always been a nerd. I think we're just lucky that nerds became cool in the last few years, 'cause back when I was in high school, being on like the Chem Olympiad team, no, I was a chemistry nerd. I like traveled around and did chem competitions.

Get out.

Yeah, man, that's how we do it.

You told me about your sort of ability to inject like You read deeply into very esoteric stuff.

I do. Tell us more about it.

A lot of science stuff, a lot of game stuff. Tell us more about your esoteric interests.

Recently, so I'm one of these, I go super deep on something. Something catches me, I don't know what it is, and I have to go super, way, way deep on it. It can be weird shit. So once upon a time it was anime and manga, and I went super deep into that world and learned everything you could imagine about Naruto and Bleach and all these— You make your own manga? What?

Make your own?

No, I don't make my own. Come on, come on, Eric. I still have a life. If you haven't checked out Naruto yet, you should go check it out. It's one of the greatest stories ever told. Recently, it's been really deep into genetics and genomics. A buddy of mine, D.A. Wallach, who if you don't know him is really scary smart. We went to college together, he was in Chester French. So any other generation, like if he was born in Italy a while back, he would have been sponsored by the Medici family, that would have been his patron fam, because he's one of these brains that sort of thinks both in art and science and math and philosophy. But he, after putting together Chester French, recently he's been putting together sort of investments into healthcare and healthcare tech. And so he got me really thinking deeply on genetics and put together a symposium where we had like 20, 30 of the sort of biggest thinkers around genetics and a handful of us that got our genome sequenced by Illumina. And it was an incredible moment. You sort of got to sort of hear what's out there. So I don't know how much people know about CRISPR, but if you haven't been paying attention to it, there's a great TED Talk that just came out like a week or so ago about what was Science Magazine's 2015 Award of the Year. And CRISPR technology, I'll try to do my best sort of layman's job of it. It's a technology that effectively turns the human genome, which used to be sequenced for $3 billion and now can be sequenced for roughly $3,000, into, you know, think about taking that entire sequence of 3 billion Gs, Ts, As, and Cs, and basically making a Word doc out of it. And now you can, with the simplicity of CRISPR, cut and paste out certain genomic sequences, which is incredible. Like, when you think about the implications of what that technology will do for the world. It is something I have been digging deeply on lately.

This brings a bigger question. From an outsider perspective, obviously, you joined Lowercase a few years ago. You and Chris Sacca have maybe the most successful seed fund ever, at least one of those funds, or a couple of them. Why not go big? Because the way you are describing when you mentioned symposium, I think of Andreessen Horowitz, who has a lot of symposiums and people that think about certain specific fields and have built this whole sort of roster that does a bunch of different things, not only services, but also allows Mark to explore his intellectual interests further, like economists on staff, so to speak. Why is Lowercase still, you know, so small? I know it's a deliberate decision, obviously.

Yeah.

So I think in venture you have these pressures, right? Like if you have a really successful venture fund, there's this pressure from LPs, from friends in the community, from companies. As you start to see these companies take off, there's this pressure to raise bigger and bigger funds and to start playing bigger or scaling up and like doing all these things that I actually think puts you at odds with your core mission. So we know what we're really good at. We're really good at picking companies in the early stage of seed, helping those companies grow, doing early product iteration, helping with the early marketing, customer acquisition, tweaking, tweaking the social nets, and sort of raising the next round of capital and partnering up with the best seed funds out there, or the best A funds, putting together syndicates at the seed round. Those are things that we do really, really well. We're not great at like helping you find your like public company vetted CFO and bringing them. Guys like Bill Gurley are gonna be better than us forever at doing that. That's just not our skillset. And so I think part of it was knowing our skillset and being honest about that. But also not falling prey to, I think, the short-term greed of venture economics where it's like, hey, we did really well in this seed fund. Let's raise $150, $200 million seed fund, and now let's compete at a totally different spectrum and frankly live off what are fat fees at that stage for a small fund. And I think that's not the direction we wanted to go. I think if you do that, you have to scale up and manage a whole group of people. And I don't think either of us have the appetite for doing it. And so that's— it's one, it's if your question is why not go big, I think we do pretty well at staying small and barbelling out.

We've—

not to say we haven't done late-stage stuff, right? We've done some of the later vehicles into Twitter and a handful of our other breakouts. But our core strength is seed. And rather than like deviate from that because of, you know, the opportunity for sort of a larger fund size and fee base, we've decided to stay super small. And I think it's better. I think it's made us better at what we do. Now the question begs like, how do you evolve seed stage financing? So like, we haven't hired a lot of people. In fact, Jackson Dahl, who might be in this, he's at school still, he graduates in May, is the first addition we've made since I joined 3 years ago. And he's enabled us to sort of do a bunch of these things in terms of servicing companies that I care about a lot. And so, In the last few months, you've seen us roll out a couple of these things that allow us to scale how we service seed stage companies without like scaling up a huge marketing team or a hiring team or any of those things. We've sort of pulled from the crowd, enabled things like Lowercase Alpha, which is a distribution platform I'm happy to talk about.

Alpha, you launched it, you know, a few weeks ago, maybe a month ago. I'm on it. It's fantastic. Tell us how that came about.

So, like, the challenge is it's Chris Jackson and I, right? And so how do you scale up services to a portfolio company without scaling up the people to service them? And so one of the ways that we've done is thinking about things that we can do really, really well. One of those is distribution. So, turns out anybody has a voice today over Twitter, over Blab, over Product Hunt. You can have a pretty sizable community, and Chris and I have managed to do that over the last few years. Of get a bunch of people in our atmosphere who are sort of in our space that are avid product testers, avid product users, first users on most products, who love talking about it, who love jamming on it, and that's sort of the people that we get to surround ourselves with. And so we put together Lowercase Alpha, which was just— for those that haven't gone on, go to lowercasealpha.com and check it out. Somebody can put the link in the chat. But effectively what it is is a beta community where if you're a product founder, you know, you're trying to get good feedback early in your product's lifecycle. Lowercasealph is a product where every month, every week or two, we send you a text message with a short description of an app that you might like that we're playing with, sometimes from lowercase founders, sometimes just from products we really love. The last one was from Polymail, which is an iOS mail product. Actually, I think it won Mac App of the Year on Product Hunt.. And, uh, it was just an amazing product and they wanted early feedback from a bunch of great users. And so getting product testers into that atmosphere that aren't friends and family is pretty hard. And so we scaled up the service. Now we have, I think it's like almost 4,000 users on the product converting into TestFlight app users. And so that's a service that we can provide to founders, say, hey, you know, we can get you 4,000 people playing with your product before you've even launched it. And have them give you feedback. And like, I think that's a different way of thinking about the value that a seed fund can give you, um, as opposed to just getting feedback from Chris and I. Now you're getting feedback from thousands of people who are early, and not just like your uncle who you beg to try your new product.

Um, what about, uh, what other services either have you rolled out or do you want to roll out? Are you effectively looking at all sort of functions of a seed stage and say, how can we build products to scale instead of—

Yeah, it's not just about like hiring, it's like, how can we use technology to distribute the work of like, of how can we use technology to leverage the work of Exceed Fund, right? And so now we have 4,000 beta testers that we can bring to an app, hopefully more soon as people start to play with it and realize that these are pretty awesome apps that are coming out. We've thought about building community for our founders. A lot of people have launched Slack networks, for their founders and people are finding a lot of value there. In the next few months, you'll see us launch a similar thing for our founders. We have over 85 companies now across our 4 funds. And so there's a lot of knowledge transfer and we're sort of right now shaping actually with Eric Mills and Stefan, 2 guys who are super active in the lowercase fam. We're building out sort of a plan for how we service our companies better. We're also thinking about like, I was on, I think like 150 flights last year. I just travel a ton. And so how do I do a better job of covering the tech events that I just physically can't get to? They're all over the world. And I've got a plan that I'm gonna start launching next few weeks around how to better cover tech events and see what's happening, whether it's at MIT Demo Day or, you know, at a tech event in India or the Product Hunt meetup in Berlin that you hosted a year and a half ago, which is how I found out about DubSmash and ended up doing that deal. Like, those are great moments that are happening everywhere, and there's no physical way— I'm not gonna scale up 15, 20, 30 analysts to go scour the world for that. But it turns out that there's a lot of people that are interested in talking about that stuff. And how do I shine a light on that and funnel their voices to the top? I've been spending a lot of time lately thinking about that. And so—

Can you tell us anything about what you're thinking in terms of how you could do that? Or is it still too early?

No, no, no. Again, we're pretty transparent about how we think about it. And I'll use these moments for people to jam in and chime in on it. One of the ideas that I've had is, I think, like, contributor network is really interesting. And so, the benefits of a contributor network are ones where you drive a lot of attention to the main channel, everybody promotes that main channel, and you get to sort of have a number of different voices in there chiming in simultaneously. And so, Eric's actually in the room, and so we've been talking a lot with Jackson and Stefan. Stefan, for those who don't know, is a 15-year-old who built lowercasejobs.com. Which is where it's a scraper that's gone through all of our portfolio companies and sort of promotes out any open job listings they've gotten, which is incredible, right? Like, that's the kind of service that, again, you don't need a whole team to do recruiting. You can build that. Now you have a way to promote all the open jobs in your portfolio. But I think, like, one of the things that we're thinking about is how do you create, like, a system where other people can contribute to all the great tech events that are happening all over the country, whether it's South by or YC, or Launch Festival this week, and sort of COVID those. I built, we built a coverage system back at CAA to cover all the different entertainment verticals, right? TV and film and sports and brands. And so how do I take the knowledge of how to build a contributor network and a coverage network and apply it to venture is something that I'm spending a lot of time thinking about.

Fascinating. Tell us about the grand vision for, for Lowercase. What does it look like in 5, 10 years?

I don't think it looks that different than what you're seeing. I think like we figure more ways to scale great services to our portfolio. You're seeing us actively think about it, right? Like as you get deeper into seed, and keep in mind like institutional seed is kind of a new entity, and most of those early seed funds have gone up that route that I told you earlier. Like they've scaled up and are now sort of moving into Series A and bigger check sizes and more aggressive round allocations. To be collaborative seed fund, what does it look like now that you've got a few funds under your belt? I don't think it looks that different, except I think you— we've built more technology and more services and more community in and around, uh, the service to it. And so does Lowercase Alpha have 100,000 or a million subscribers on it that are now like each month trying new products that are early and, uh, and sort of helping from that perspective? Does Does that community exist now around Lowercase Alpha where people bringing up more and more sort of events that they want to cover and talk about? But I don't think we've gotten to like 15 partners. I don't think that's in the cards for how we think about it. Chris basically did like a 10-year vetting process on me. We met like over a decade ago before he brought me into Lowercase. And, you know, not to say we wouldn't grow the team, but it's not like an aggressive, like we're looking for the next group to bring in and we want to scale a huge fund size. I still think early stage seed is the most exciting time to be investing, the most exciting part of the value stack. And hopefully this industry still exists and we can still keep building like this.

Yeah, I mean, you guys think really smartly about how to spend your time as VC and where it's most effective. I remember you telling me that it was a third, a third, a third, right?

It was a third.

Nice. Finding companies, a third helping companies, and yeah, what was the other third?

The third, so it's one-third, this is time management, just it's like a back, back look at sort of taking a step back and looking at how I spend my time. It's like one-third is spent on our existing portfolio, how do we help them, how do we service them, uh, whatever they need in that moment. Another third is, uh, identifying new companies that we can invest in And the other third is sort of portfolio management and LP management and conferences and brand building, just sort of like the network that contributes to all of those other things.

Right. And I'm curious, so part of the management, you're trying to cover a lot of events and that'll save time, but you make, just because of your experience at CAA and, you know, your relationships between entertainment and tech and then everything that comes from, you know, Chris Sacca's, you know, network and sort of brand, you make a ton of intros and connections and are consistently bringing people together. Is there, are there tech ways to make that easier? Or, you know, what do you think?

Yeah, I mean, like, I'm sure there are. I see a lot of those, like products that are built around how to better leverage your professional network and intro solutions and all of those kinds of things. But the more I've tried to like scale those and like take away the work of those or can load those responses, the less valuable they become. I think Chris and I spend an exorbitant amount of time and well worth it on like crafting good intro emails and like spending the time there. Turns out like, yes, you can scale up those connection like processes, like literally I can can a response. It's like, here's this person, here's this person, go. But like, if you've ever seen one of Chris's intro emails, he's hilarious. He like puts like an anecdote about one person, anecdote about another, sets up the opportunity, and he does it in like 6 sentences. And it's like a structure, right? Like, and he's amazing at it. And I try to emulate some of that. But I think introductions are actually one of the most important things that like you do in venture, connecting people and frankly in most industries. And it's a skill that I learned at CAA, I think, which is, Take your time with it, and it's really, really important to spend time making those introductions, 'cause the value isn't just in the connection, it's in the context, it's in the how you frame it, it's in how you disarm people so they sort of feel comfortable and bring more value to the table for each party.

Say more about the science, because people way less accomplished than you two will spend no time on an intro, and I've gotten intros from both you guys, and they're really, well-crafted and I can see that, but tell more about the long-term value. You think about it, it's a science. Explain the science.

Yeah, I do. Again, there is formula to it, right? The formula is, "So-and-so meets so-and-so. They are this," and then provide the context of what that is, who they are, what they are, something about them that's interesting or relevant to the moment, and then the same thing in reverse, and at the end of that, with the interest, like the point that you're trying, like the context specifically to why they're both gonna get value out of this conversation. So first line is so-and-so meets so-and-so. Next line is, you know, this is what the person B does and why I think you'll enjoy them and why, like what my interaction has been with them. Then it's what person A does and a little bit of like why they're valuable and then the context for why both of you will enjoy it and then immediately like let you two take care of it. And always, always opt in. So I never say I'm gonna make a blind intro. I literally— that is like the most aggressive thing that you could do to somebody. It's presumptive that they're gonna want that introduction, that they're gonna get value out of it. I always ask for that in advance. And so if there's a company of ours that wants that introduction, I usually have them frame the context in more full email before and forward that along with my version of why I think the relationship will be be valuable.

Right.

There's no cold intro that comes out of my world.

Why is it so valuable to have it so well crafted?

Because people are busy as shit, and it's social capital. And so the combination of like, I'm super busy, and this is gonna be an important moment, and like, people will usually take an introduction if I bring it to them in the right context. And so I don't want them just to take the meeting, I want them to actually get whatever the objective is out of the introduction. And so I don't just like set people up like, hey, I think you two will enjoy each other's time. You can do that through a lot of people, and social is a great vehicle for it. I do it like specifically, hey, here's the moment that I know you're gonna have value on, and I hope in addition to that you guys build a great long-lasting friendship. But I hate the cold moment. I think it's lazy. I think it's lazy both ways. I think when you make a cold outreach, unless you personally crafted it with like specificity and with like a reason why I'm reaching out to this specific person and some sort of a lot of personal specificity, I think it's gonna be really not worth your time. I think it shows lack of hustle.

You guys should write a book on this or something, like some content out there.

People write about this all the time. We do the same thing around like update emails. We care about communication. I think communication is the stuff that you like, you can send out, like you can do an update email and you, in that update email can be like all the data points and it can just be sent out with no context, no framing, no narrative, no storytelling. And you haven't done the job. We do an update email for our LPs every month, every quarter, or try to every quarter. And alongside like the financials of Lowercase is a narrative. And that narrative is, here's what the industry looks like. Here are the trends that we're seeing. Here are the companies that we've invested in, not just logos and amounts, but like why we're excited about it, why we're gonna help, and why we think you'll love this investment. And like that framing, that narrative is like really frickin' important. And if you bail on that because you're just putting context, content in there with like data, you're missing a huge part of the storytelling and narrative that goes into like the investment. And I just think that's lazy. I've spent the entire, last month and a half going through all of our portfolio, every single one, and trying to frame for them what I believe to be the perfect investor update. I think it's worth the time. Like, we've had catch-up conversations with all our companies, and I spend a lot of time putting out, like, here's what I believe the best version of an investor update is. And this comes out every once in a while, and like, some firms have done great versions of it. Like, uh, First Round, I think, does an amazing job of it. Um, but I have like a framework that I like for how to do an investor email, and I and I spend time with our companies on it. I think it's important.

Will you ever publish one of those as an example, or are they super private?

Why don't we do it right now? I'll do it really quick, and somebody hopefully who's watching can take a note on it, and maybe they can type it up. But yeah, I'll eventually do like, not just write up a Medium article on it, but maybe have some of our portfolio companies share with like the numbers blurred out. We have some of them, just killer, killer updates.

Sweet.

You ready?

Yep.

You wanna rip it? Alright, so it starts with, like, let's imagine Eric Thornberg Co. It starts with the definition of what Eric Thornberg Co. is. It's like a reframing. If you ask most of the employees of Eric Thornberg Co. what Eric Thornberg Co. is, they wouldn't be able to describe it with the same language. Companies change so damn fast that like how you frame your company day to day, even for the people that are in the company, Right. Shifts. And they probably aren't all on the same page in terms of like describing the value proposition of the company. Right. And so for an investor who's a month removed or 2 months removed from your last update, the company may have totally shifted its value proposition. And so start every version of this email like, what is Thornburg Co.?

Mm-hmm.

Sentences. And what that is, is like, if I'm out there or any of your investors, advisors are out there, or even your employees are out there talking to press, partners, other funds, whatever, they'll have exactly the right framing for how to describe the company.

Right.

Two, most investors nowadays are also distribution. If you have Hunter Walk in your fund or if you have Sacca in your company, like, turns out like they have huge distribution. MG, Souster, Fred Wilson, all these people have built out like big, big blog networks, right?

Yep.

They can be your mouthpiece. And so they can talk about trends that are happening in this industry that you care about, new evolutions, whether it's about your company or not, success stories. Literally frame for them 3 things, tweets, social posts, whatever, that you want to send out. Literally copy-pasteable, so they can push something out that speaks to the movement that you are pushing towards. I believe it's actually a really sort of missed opportunity for those updates to be like, these are all homework assignments. I treat like the update not as like a moment where you're reporting back to investor, but like as a homework assignment for all the people that are in your world. I was also like, I care about the framing of it. Don't BCC people. CC everybody that's on your team. Make them all aware that like, hey, we're all sitting around this fire together and we're all like responsible for helping together. Like the BCC makes it seem like, oh, I don't wanna reveal emails. Turns out like your investors should feel like they're employees. Right?

Um, when do you BCC people? Do you BCC people at all?

Yeah, you BCC people when it's like, uh, an event, or like when you have like— we've all seen those like crazy emails that go out with like everybody's like email on the list. Um, it's lame. Don't do that. But for your investors, that's an appropriate time to CC you, right? Like, hey, we're all on this team together. We've all— we're all moving in the same direction. You're all partners in this endeavor. Yeah, CC. Next, it's so Tornberg Co. Tweetable shareable moments stories. 3 is the asks. This is the homework. This is like specific asks, not just like I'm looking for a dev for iOS. It's parentheses Matt Mazzeo looking for a dev in iOS. Here's the, here's the profile. Here's a forwardable email that you can push out to everybody and with a link to the job description. Next, and it's like looking for partnership in PR, like need introductions to firms, and whoever you think is gonna be best capable of accomplishing that goal, assign it out like that, okay? And so what this does is it puts personal responsibility on the people who are your investors to go and accomplish tasks for you. Have them take shit off your plate. And then right below that are thank-yous. Thank you for so-and-so for getting this done., and then in bold, still on the plate, the person's name that you assigned it to last month. If somebody didn't get shit done, call them out, and be like, hey Mazzeo, I asked you for this last month and you didn't get it done. What the shit? Yep. And it actually really, really helps in people getting things done. Number 4, it's the same thing, accountability that you would have for your employees, right? You wouldn't let your employees off the hook. You shouldn't let your investors off the hook when you ask for help. Right below that, and by the way, we keep track of that stuff with other— like, I keep track to see which investors are getting those things done. Like, I just know inherently from the, from the companies that I've, uh, invested in that do the updates like this who's getting those kinds of moments done. Like, oh, I love that TX at Carlin is executing on that, and like, he's super helpful, um, and I'll keep bringing him in when I know that he's going to be valuable to that process. Into the companies that we invest in because I know he's amazing. Below that are KPIs starting with bad news. Like, put the bad news first, don't sugarcoat it. Give like a chart that's like whatever your 5, 10 KPIs are, put them all together and put some under the bad news category, some under the good news category, and make sure that those charts are continuous. And like, you can automate a lot of this, by the way, like by assigning it out to different people in your department, in your company, be like, hey, does anybody have an ask for the investors in X, Y, or Z? And make different employees responsible for different parts of this, the good news, bad news chart. Below that is something about the company, like culturally. This is actually one that most people forget. Like, turns out you're building these great memories and like, I recommend to all of our companies that they like store some of the narrative of like the evolution of their company. Like that big client they sold, that big, you know, an internal birth, a company photo, like all of those things are like milestones along the way. And it's easy to lose sight of like the humanity of this in like just the numbers of the update. The more you make it feel like this is a company and we're all in this company together and it's a culture and a family, the better I believe you will be long-term. And so I always include like something about whether it's a customer success story or an internal success story, something about the company and the team.

Now let me ask, let me ask, what, you just open this open window?

Yeah, yeah, you've been asking, you've been asking a bunch, right?

Why you do you have the— I hear an echo. Do you hear— have this page open in a separate window or— no, it's good.

I don't.

No, no, now it's good, that's good. And don't worry, this will be edited. Uh, okay, let me ask you this. So you've been investing, uh, at Lowercase 3 years now?

Yeah, a little over 3 years.

Over 3 years. I'm curious about the evolution as an investor. And obviously, you've done a great job. What is the 20% of work that you do that brings 80% of the results?

20% of the work that I do brings 80% of the results?

What is the really— what have you found like really moves the needle in terms of where you should double down and spend your time where you weren't spending enough time previously?

This is the hardest part about seed investing, right? Like, there's a venture trend that we're talking about where like the time to liquidity is like longer than ever. The feedback loops in seed are so long that you made an assumption there that I'm good at this. I won't know for a decade whether I'm good at this, right? Like, I, I'm fully aware, and it's actually the thing that scares the shit out of me day in, day out, is I have no clue how successful I will be if you measure success by return on capital. Like, It takes a long time to figure it out. I believe, and I'm measuring my success in proxies, right? But those proxies are skewed a little bit from follow-on rounds, from hype around some of those companies, from an early acquisition that, you know, those things help. But like, I won't know how good we are at this for a long, long time. I think Chris's, you know, legacy is pretty secure in lowercase one. From the early investments there. But for me, I got a long way to go before I figure it out. Let's be straight about that. I think the stuff that I spend my time on that will be most valuable— it's a hard question. I think it's been time spent with portfolio. Like, that is always the best time. And then also, like, this second evolution of what we're trying to do in terms of, like, scaling out services. I think long-term, if I look back, like if I'm putting myself 5 years out, I think things like Lowercase Alpha will be some of the most valuable that we do. But I'm figuring this out as we go. Like, do I believe that the future of early-stage venture will be around like the things that I've talked about in the past, like site selection and service, right? Like, I believe that we will see the most deals because we have a collaborative fund that's small and nimble. Chris has a great reputation, I'm building hopefully a good reputation, and our companies like working with us, and so we'll recommend people. Yes, I believe like our site will be good. Selection, I'm not sure, I'm hopeful. We've seen early success, I hope that continues. I'm not positive yet, data will tell. And the service piece is where I believe that I can make the most difference, right? Like Lowercase Alpha is a service to companies who wanna get early beta testing. I will build more of those types of services with the help of people in our network like Stefan who built LowercaseJobs to help people recruit better. I believe there's things like that that I can do to improve how we service companies. I'm spending a lot of time on that. So looking forward, I think that will be the best 20% that I can provide both to portfolio companies and increasing our ability to select and service those companies long-term.

Khosla, I believe tweeted this or something, said something along the lines of 70% of VCs actually provide negative value. Is that true? And more importantly, you know, when you work, talk with founders, and when you work with founders, where do you see you bringing the most value? Like, what is most helpful? What do they want from you? And how can you provide value?

Um, how can we provide value? I think we do it in a few ways. I think it's gotten better over time. I think we're really good at understanding how to tell a story and how to tell a narrative around companies. I think that's a lost art. I brought this up before, we care about it a lot. How you tell your own story and how you pitch it is something that takes years to learn. Some people are just natural orators, some people are just natural at framing beginning, middle, and end to a story and understanding how to craft that pitch for different audiences. It took me years at CAA learning from guys like Richard Lovett, who is probably the best salesman I've ever met, and some of the people there who are literally the greatest salespeople of all time, and they just tell stories.

Richard's so good. Why is he the best?

What made Richard so good? Empathy. He was one of the first people I ever met, he'd spend most of the conversation just listening to what you wanted. Listening and understanding like what drove you. And at the end of every conversation, he tried to like deliver value. He's like, what's one thing that like you most wanna accomplish in the next year? And from that, he would leave. I don't care who the meeting was with. It could have been the biggest person in the world, it could have been somebody who's just on the up and up, but like he would end a conversation like that and take the note on like who that was, what they were doing, and then try to execute that. It was a crazy value proposition for anybody, 'cause Richard was one of those guys who could make anything happen. And he would try to for everyone he spent time with. Like, that's an amazing sort of talent and skill. But beyond that, he just listened really well. And so he knew who he was talking to and he crafted a pitch. The most, the worst pitches are the ones that are crafted for like one size fits all, as opposed to like knowing exactly who you're talking to and like what's gonna resonate with those people. And so we spent a lot of time with our founders, like helping them craft like the perfect pitch for hires and for sales and for the press and for the next round of financing. And leading into their Series A or leading into their Series B, like that's really, really important. And you build that with reps and turns out we get a lot, a lot of reps. We had, you know, whatever it is now, 85 companies. We built a lot of reps around that storytelling and different funding cycles and different exit moments. And like, that narrative is really, really important for us. But we also like, I like to think that we're good at product too. We play just by, again, reps help. I play with like every product that comes out. Really early on Product Hunt, really active on Product Hunt. I downloaded most of those products just because I love doing it, never felt like work. And so I was probably one of the first people on Blab too, just because I love it. And I— this is what I do like in my downtime, is just like jamming on fun products, whether I invest in them or not. Like, I get to take something from all of those conversations with founders. And like, why did you make this product decision? That onboarding is really interesting. How did you come up with that? What's the intent? What's the trade-off that you're making with this? With this feature set. And like, hopefully that some of that comes through osmotically to the rest of my portfolio, is that I can take in that information and then disseminate it. Like, this is the best onboarding, this is the best way I've seen social done. And so I like to think we're good at that. The BD stuff, it comes easy, right? Like, I think that's a unique value proposition. There aren't many people that spent 8 years in entertainment. And so anything that comes to entertainment stuff, it's just Easy. At CAA, I was responsible for doing BD for a bunch of tech companies and got to know most of the people at studios and networks and talent and agencies and management companies. I got pretty good at that, if I'm gonna brag.

Your first one. When you said osmotically, did you mean— is that by osmosis? Is that the adverb form of by osmosis? You said osmotically?

Yeah.

That's awesome. I'm a nerd.

You are a fucking nerd. That is awesome. Okay, so I'm just sort of amazed by your energy and your ability to consistently put in the reps and put in the work. I want to get sort of around any sort of habits or rituals you have around that. Tell me about your first 90 minutes of your day.

First 90 minutes. I'm up usually— it doesn't matter anymore. I used to be a night person. Now I'm a morning person. I'm up at 6:30. 6:30, I immediately reach over. I think my time to cell phone is freakishly small. My girlfriend would tell you that it's compulsively small, but I'm up and reading for the first hour of every day. I just, I can't stop. She tell you it's really small?

I'm just kidding. I'm all right. Okay, you get your cell phone, you're up.

Yeah, I'm up, I'm reading. Techmeme, Nuzzel, Politico, HuffPo, my Twitter feed. I'm like trying to pound as much of that information as possible. By the time 7:30 rolls around, I like to think that I've cut medium. I like to think that I've covered almost all of what's happened in the last 24 hours and will be talked about in the next 24 hours. It's just, it's how I spend my first hour. I love, I love that moment. I probably like, I've gone through my front, my homepage of my phone, which is like, see, Product Hunt, shout out. Uh, uh, Nuzzle, my Slack, Twitter, and, uh, and the, the 10 sites that I check every day. Um, it's just how I have to start. Like, like, even when I'm half asleep, like, I'm laying in bed reading through all that. By 7:30, 8, probably, uh, work out, coffee, back home jamming. And then the days lately have been packed with a lot of meetings. I think this is the biggest differentiator between Chris and I is like I get excited and sort of in my zone when I'm sitting down with people and interacting with them and understanding why they're doing what they're doing. I spend more of my time in meetings than I probably should, but I still enjoy it. So—

Are you anywhere from 5 to 10 meetings a day?

Yeah, at least. And that's not including the calls that you're doing back and forth. I don't have a lot of time during the work day, that I'm spending just thinking, and so I get that in the morning and then I get that super late at night.

Right, and do you, and Chris spends more time sort of writing, would you say? Or, you know, he's also got kids.

Yeah, he's way better at like, I'm gonna dive in for this 2-hour period, I'm gonna crush email and get through that. And I'm the kind of person that like, I'll have an idea, I'll pick up the phone, I'll give him a call and like try to jam with him, and he just hates phone. Like I think it's his least favorite medium. I'm like, the exact opposite. If you know me at all, if you're in this chat, you can attest. I FaceTime people, like, I'm a FaceTime assassin. I want face-to-face, I wanna see your reaction to thoughts, I wanna jam with you like that. I do that to you like half the time too. You've been overseas, and like, I'll have an idea for like, hey, this is an interesting one for you guys to think about, and I'll like FaceTime you. It's a holdover, but it's also like, for me, this job's a little bit, it can be lonely at times because I'm sitting, you know, at this desk until Jackson came on about a month or two ago. It was literally just me at the house, like in my own world. And so I get my interaction from like all of these different meetings I'm taking. It makes me sharper.

Do you have any other sort of rituals that you swear by? Rituals, like in terms of like anything you do every night or something you do in the middle of the day or something every week or? Every quarter, just something that you've, a habit that you've picked up, or something that you, has been a good luck thing, or just?

No, I think, you know what, there was a ritual that I got into before where I did like the live streaming stuff, and I was kinda doing like the morning jam session every day, and I kinda miss doing that. I don't have a ritual around like, ritual around, ritual around, ritual around like getting feedback. Okay, um, I don't have a ritual around, um, most things. It kind of— the answer is no. The morning read, the workout, the coffee, that sets me up for a good day. Um, the live streaming stuff where I'm like consolidating my thoughts, or like I try to do at least one or two jam sessions with people who I love and respect, like a week where I just talk about something that I've been thinking about for a long period of time. And that's how Lowercase Alpha came about. That's That's how the next evolution of like some of our community stuff came about. And that's how there's another product that we're like gonna sort of announce soon that we've been building just as a service to portfolio companies and non-portfolio companies. Like all of those come out of like little jam sessions. You and I do it all the time. Like we'll sit down and like have dinner and those moments, I treat that like a ritual. I try to have those kinds of like creative moments with friends talking about products that we wish existed all the time.

Absolutely. Now, I want to get— there's a couple questions here from people asking, how would you give advice for a young person to break into VC? But I wanna broaden the question to ask, how would you, just a person outside of San Francisco or outside of the tech scene, how do you break into tech? What are some principles you would advise both maybe on the startup level or on the VC level and how should people even even think about sort of building?

Okay, so two different things, right? Like, starting out, like, let's do the VC one first. I think to do the VC one, like, if you wanna be in VC, there's no direct path, obviously. It's actually, it's really hard to sort of like come up with like a strategy to get into venture. Because if you look at the sort of paths of all the different partners out there, Some have been operators, some have been finance people, some have been analysts on Wall Street, one has been an agent. Like, there are all these different paths towards it. But the universal sort of thread for all of those is they had some unique angle across one of those three spectrums, right? Site selection or service that they were able to prove out. I think as a— as somebody trying to jump in, you can nail the service piece way before you can do the site and selection piece. But you can sort of start to prove points across all of those. And if you prove points against all of them, you can sort of make a case for why a firm should bring you on. And that's what they want to see, right? Like, and if you start to say like, okay, if I need to prove out site, maybe I'm the one that's writing the post. Maybe I'm not writing, maybe I'm not investing my capital, but I'm writing a post before that company has gotten traction saying this is going to be an amazing company. If I were an investor, I would invest. I'm coming up with this off the top, so bear with me. For selection, Same sort of same kind of thing for the service piece. You can actually do that right now. Like Stefan, who I've talked about a couple times in this podcast, is a 15-year-old in 9th grade who built lowercasejobs on an off day and decided he was going to spend a few hours of his time, or God knows how much of his time, collecting all the job sites that exist for lowercase companies, publishing them to a website that was like branded with lowercase stuff. He didn't ask permission, he just knew it would be valuable. And posted it out. I'm like, that's amazing hustle, and it's a huge value proposition. I've given this advice to a few people, like, even who are, you know, principals or associates at different companies. Like, if there's a firm that you wanted to work at, right, or a partner that you wanted to mentor, that you wanted to be your mentor, identify their portfolio companies, start adding value to those portfolio companies. Just reach out and like literally just deliver whatever value you can. And find a way to say to them, "Hey, I don't need any payment. I don't need any recognition socially with the exception of if you would say a thank you in your next investor update. That would be hugely helpful." And so if your name, person X, kept appearing in my investor updates as, "Hey, we had this amazing, you know, person come in and help like across all of these things," and I kept seeing your name appear over and over in all of these investor updates, I'd be like, Who is this human being that's like delivering more value than half of the cap table? That's incredible. And you can just start doing that now. You don't have to ask permission. You just go and help all of those portfolio companies. I would make that case, right? Like, turns out I'm of service already to your portfolio. I'd like to do even more and make it my full-time job. Hire me. That'd be an interesting pitch.

Let's dive deep because a lot of people get, you know, add value without return. What they don't understand is sort of how can they add value? You know, one example is what Stefan did, help people, you know, get jobs or sort of make it easier to find what jobs are open. What are other ways people can—

Eric Wills isn't here. Eric Wills is like one of the most active human beings, you know, in tech, I think. He's just like a superhuman. I don't know, he's incredible, right? Like you've interacted with him. You introduced me to him.

He's 4 people in 1. Yeah, he's amazing.

I think there's 9 of him. I actually believe that entirely. And Eric, Eric's one of those people who's just like, likes to be helpful and has a system. He's got a systems brain and he likes setting up systems and he likes being like, he likes being active and voicing his opinion. He's got strong and really well-researched, thought-through opinions. And so he just comes in, he's like, hey, whatever we need. And they start doing things to push the ball forward and ask for forgiveness rather than permission. I think he's one of those people that's just present. So if your first question was how does somebody just start like being active in tech, it starts by just going to the events, right? Like I started in this world by like going to YC Demo Day and going to like South by Southwest and going to like, you know, all the demo days that I could get my butt into because like that's where I wanted to be in the room and just hearing. TC50 or whatever it was then, TC30 when Jason used to, what was the precursor to Jason's Launch Festival? Was the first tech event that I ever went to. I was 23 or 24 at the time, and I just sat there and like absorbed as much as possible and went up to Jason at the end. I was like a little schmuck, and like, I was like, hey, this was amazing. Like, thank you. I learned more in 2 days than I ever thought I could about tech. And I just started going to a lot of them. And so I would say just start being in the room is a good way to start. I've said this to you before. Oh, sorry, go ahead. I said this to you before, which is, if I were starting out in tech, the way that I would do it today is you just go work and mentor an apprentice under a great founder and find it. So here's the very specific process. I hate when people are like, just hustle down a job and like hustle down a company and you'll get in. I'm gonna be very, very specific. If you wanna work at a startup, I believe, I believe a startup is the best place when you're really young to get your hands dirty, to add value, and have your age not be a detriment but be an asset to you. And the most important thing is to find somebody to apprentice under. So I would go out if I were trying to work in startup land, and I would look at all of the companies in the last 6 months to a year that had raised seed or Series A funding. I would do a list of those companies. So you can go to Crunchbase, AngelList, wherever you want to find it. Make a list of those companies and the cities that they're in. Be okay with the cities that they're in, but be flexible that you might want to move to one of those cities if you found the right company. Make a list of like what the mission of those companies was. Identify the mission, and if you love them, and then make a list of the founders and which one of them had been sort of seasoned founders, and then a list of the VCs and which VCs you, you thought were respected. And now you've sort of hedged your risk. Identify in those companies which of those you believe have the best mission possible, something that you're gonna brag about to your family, that you're gonna be passionate about. And like bragging is actually a great metric for it 'cause you all wanna feel like proud about what you're working towards. Find a company whose mission you wanna brag about and start thinking about how you can add value to that founder's life immediately. With some of the things that we've been talking about, like do a project for them, put together a list of customers for them, start talking about them to publications, whatever's in your toolkit that you can add value on, do it. And then reach out to that founder with an email that says, I love your company. And if you can get a warm introduction to that person, even better. But I love your company, I love the mission, I'm more passionate about it than anything in my life. I wanna come and apprentice under you and work for this company. And I'll add more value than you've ever seen. Here's the work that I've already done. And I just, I believe in the future of your company. And I will literally, I will work harder and further than anybody you've ever hired to improve the life of that company. And give examples of exactly what you've done to this date and what you would do in the future and say, I don't care where you put me, I will find a role and I will be affordable and start for you.

And you've done this in your own life, right? Like tell us how you got the CAA gig.

CA gig was funny. I was interning for a guy named Milan Papelka at a production company here in LA, and I was just the most obnoxious human being. I took home every contract that he'd ever written and like came back on Monday morning on my first week on the internship. I was still 22, and I highlighted all of this term that I didn't know, and I was like, hey, I read everything, can you teach me what I'm missing? He was like, sweet God, get me out of here, I'm getting you out of this office. And he got me a job working for his old boss at CAA. And then I kind of did the same thing there. I failed miserably off of my first desk. I crashed my boss's car on the first day. Somehow landed working for a guy named Michael Yanover and Richard Lovett and Michael Rubel. And they let me apprentice under them. And I just, I was good at writing PowerPoint decks. And so that was, I was terrible as an assistant, but great at writing PowerPoint decks. And they kind of let me just keep doing it. So the first one I got to write was for Funny or Die. At like 23 or something, and they just let me go off on a tear because that was actually a skill that I had. And so I was just writing decks all day long. Turns out it's still a good skill set to have. I spend a lot of time helping companies today write up their pitch decks.

But at this point, you were going to be an agent, or what did you think you were?

Uh, I— what did I think I was going to rise up to? I didn't know. Uh, I had the belief that like that adding, that the right path would be one that like opened me up to as many opportunities as possible. The business development group at CA sort of sat on top of all the different business divisions at CA while the company was quintupling in size and starting a sports group and a digital group and an office in India and an office in China and all these different things. And I got to see sort of like the 30,000-foot view of the entertainment world. And I knew that would be valuable. I knew the learning would be valuable and I just needed to stick right in that spot Then nobody cared about digital, and I was like, "That's what I love doing." I read Slashdot. I was super into all the tech blogs, and so I just sort of made that my niche. I was cheap, and nobody cared, so I kind of got to build. Timing was perfect for me. I got lucky.

Let's go back to even 5 years ago, before Lowercase, but you've been a bunch— you become an exec at CAA. Life is good. But how did you think, you know, hey, these are my skill sets, these are my assets I've built up, what's the opportunity? How were you sort of, what's the long-term opportunity? How—

I wasn't. I was just head down. I wish I could say that like this was all a planned trajectory. None of it was a planned trajectory. It was like, heads down, what's the opportunity right now? Am I building more? Am I learning more? Am I like head down on the projects that I'm excited about? Am I passionate about it? Do I have good mentors who have my best interest at heart? And am I part of a growing organization that's exciting, that I feel proud to work at? And like, there wasn't even—

Wait, let's— What? Let's say you were evaluating it, knowing what you know now about sort of, you know, the tech industry and your skill sets and the opportunities. Did you think, you know, if you go back, did you think you might wanna start something? You know, obviously you have the dream gig, but how does it, what ties this thread together? Like, what's that?

What thread ties the people? The people is the answer. Like, I've always gotten to work with people I like really, really admire and respect. And so I wasn't looking to leave CAA. The clients were incredible. My mentors were amazing, like Richard Lovett, Michael Yanover, Michael Rubel, Brian Lord. Like, those people are— and all of my closest friends still. I still go to like New Orleans every year and build houses with like 40 of my old CAA colleagues. Like, I could walk down the hall and like see like some of my favorite people in the world. I get to work with any clients and like build any kind of project we wanted. There was like literally never a no, and the company was fun and exciting and growing. Like, I love that place more than anything. But you follow mentors, right? Like, I believe that this world is all about mentorship. I believe that like the people above us make us better and challenge us and like drive us. And so I— that's why I think school is really important. It's a really great a great meeting ground to find mentors, peers, and those above us. But more important than that, like, there was a guy who I got to know a decade ago who was the closest to the man that I wanted to be when I grew up. He was a great father. He was a great thinker. He was honest, and he was great in terms of moral compass. And he told me that he would train me. And you don't find people all the time that tell you that they will make you better. That invest that into you, that have the same moral compass as you, that like I've seen repeatedly exchange long-term— exchange short-term for long-term and like continue pushing to build something that they're proud of. And that was the person that called me one day out of the blue. Like we'd always been close and we'd always been jamming on content and products and like companies that he was building and he was trying to get me to go and join different companies. But when Chris called me and said, hey, I've never had an apprentice, I've never had somebody that I wanted to train, and you were that person. And here, if you build— if I'm bringing you in for Fund 2 and 3, and if you're great, you can, you can lead Fund 4. Like, that's the opportunity of a lifetime, not just because of the economic opportunity, but because there's a person who you really deeply respect who's going to be your mentor. That's a really hard thing to find. And it was hard to leave my crew at CAA. They're family to me. But I, uh I will follow that opportunity every time. It's the best—

What? Was it— It put you in the right position.

Helping out? Oh, you're breaking up a little bit, Eric. Sorry.

What put you in the right position? To take advantage of that opportunity.

Still breaking up. You wanna type it? Can anybody else hear him? Or am I breaking up? Eric, refresh. How do you set yourself up for the opportunity? Um, interesting question. Um, so Eric's gone. I'm gonna answer that question anyway. How did you set yourself up for that opportunity? Uh, I set myself up for that opportunity, um, luckily I got to know Chris over a number of years. I was always helpful to some of the companies he was working with. And one day we were sitting randomly next to each other on a flight to San Francisco. I was going up at the time, uh, building out CA's venture practice, flying up to San Francisco every week. He was going up, no joke, for an Obama meeting. And I'm sitting next to him on a Southwest flight, which I think was randomly the only time Chris has ever taken a Southwest flight. And he asked me like what I thought about the digital video space because he was putting together a vehicle, an investment vehicle called Stampede, which I would later go on to sort of run., but at the time he was just like, what would you do to invest in this space? Turned out it was a space that I knew really, really well. And so when he asked me that question, I gave him an entire breakdown, not just like on the, like a few parts of the digital video space, but on every part of the digital video space. And I thought about it for a long time afterwards. And without him asking me, I spent the weekend putting together a deck, again, back to the decks. I put together a deck breakdown of what the video ecosystem looked like. Here's what Fullscreen, Revision3, Maker Studios, AwesomenessTV, like here's what all of these companies look like, and here's how I would think about piecing them together to build like what a media company of the next generation looks like. And it's just something I was passionate about. I used to represent Michelle Phan and Phil DeFranco, and a lot of people that went on to start those companies, like George and Ezra at Fullscreen, and the team at Austinist, like I just knew a lot of those people. And so, right place, right time. It was just the skillset in an area I knew intimately. I was ahead on that market and it was valuable enough to Chris and the write-up, the effort, the hustle that I put into writing up that deck and giving it to him as an investment thesis opened up the door for me to then come in and build that and then have him train me in all the other areas and then eventually trust me enough to take over the fund in the early stage investing.

It goes back to telling stories, the ability to do that and help other people do that.

Yeah. I didn't know. I was happy at CAA. Who knew that spending like an entire weekend putting together an investment deck and thesis on like digital video, because Chris without telling me had a fund that he had built for digital video, would turn into the career of a life, like my dream job. I had no idea. It was just like I knew about it, I knew I could be helpful, and I was helping a buddy. And it turned out that like that was enough that he pushed him over the edge, and he already had the 10 years of diligence of knowing that I wasn't an asshole. Or at least that was the kind of asshole that you want to work with.

So I want to close by ending with a game. I just want to respect your time. Do you have to bounce in 3 minutes?

I also like— we didn't get anybody else in here. I want to like— let's play around with people.

Perfect. Let me ask this last question and then we'll let a bunch of people hop in, or as long as you can stay. Yeah. So I'll play this game. I'm going to name a person. That you've worked with in some capacity. I want you to say something special about the person, or maybe a nuanced opinion of them, or agreement, or thought on them that a bunch of us don't know about, that isn't public.

Oh God, okay.

But nothing too revealing. So first, Ethan, talk about Michelle Phan. What don't we know about Michelle?

What about Michelle Phan? So I met Michelle, I don't know how, she was like 21 years old. She had just moved out here from Florida. She couldn't get a job at Dillard's. So Dillard's, she applied for a job back in the day at Dillard's doing makeup behind the counter and they wouldn't allow her to do it. And Michelle, Michelle to this day, like she was taking care of a bunch of family, she was helping them out. Michelle is one of the most humble and down-to-earth human beings you have ever met. Like, and it's not an act. It's not like, um, it's not like a character. She just helps people all the time. Like, um, she really is one of the most humble human beings I've ever met. Like, that job at Dillard's, um, that they rejected her on, like, just drove her. She's also incredibly curious. Like, the other thing you might not know, she like She studies everything from like Eastern medicine to like, what's it called, to astrology, to tech and science. She's like one of the biggest nerds you've ever met. Like first on all the products, like loves playing with products. She's a gaming nerd too. She's just like this incredibly well-rounded, humble, awesome individual, and I got to see it like firsthand early. And she treated everybody with like this incredible respect too, everybody that she ever worked with. With incredible respect. She's one of my favorite people, period. I think she's like this generation's Oprah. Like, she just comes from the best place ever and wants to empower other people to do better. I don't know what else to say about her. She's really— it's not just like makeup videos. You knew from the very beginning that she was like building something incredible, and all of it, all the success you're seeing now was like a decade of work in advance. She really is that, that Special.

How about our man Gary Vee? What is he so great at?

Gary Vee, what's he so great at that you don't know? Gary Vee's, you know what, this is something interesting about Gary. I think, and I've known Gary, Gary was a client at CA back when he was like the Wine Library guy, and he was becoming a wine lifestyle expert, so pre-Gary Vee that we know him today.. He was just a person who loved wine and built his parents' wine business into the most successful wine e-commerce retailer in the country. But what you don't know necessarily about Gary is, because he talks a lot today, is that he's an incredible listener. Like, he spent— the way he got into this world was by taking his skill, wine, holding like wine jam sessions with people, and putting that group together in a room, and just being a sponge for it. Yes, he had opinions. Clearly he has opinions if you follow him on anything, but he just, he knows also when to stop and listen to people and absorb ideas from people. And so those jam sessions from back in the day, I remember Gary basically like emceeing some of those moments and saying like, I really wanna learn about social, or I really wanna learn about VR or Bitcoin, and having a corral of the best people in the room start to take on those challenges and just be a sponge in those moments. Interject an opinion, but as a way to like spice a conversation that like made him better. And he remembered those moments and took in that feedback. So you might think of him as a person who's like just a guy with opinions, but he's actually like the best listener I've met. That's his superpower. That you might not know. Isn't super obvious.

Or competence or something, or something that makes him great that, that, you know, isn't the first thing.

God, um, I mean, his moral compass is incredible. He's got a great way of like— I've never seen somebody long-term optimize better than Chris. Um, like, even at the point where I know it is going to cost him millions or tens of millions of dollars, I've watched him step away fearlessly from tens of millions of dollars. And because it didn't line up with the way that he felt on a deal, it's like a lot of people say they would do that, and then you see $10 million or $20 million, you're like, that's a lot of money for any human being, and he will walk away every time if he doesn't believe in the vision and the moral rectitude of that company, or of that business. It is, it's really impressive, and it's like the kind of thing that inspires you to wanna work with somebody. I've never felt pressured in 3 years to do a deal that I didn't feel like I was going to be proud of, and in business, that's something that is rare, and I think that's one thing that he's just like, incredible at. In addition to that, I think he's also, um, he's, uh, he's kind of an introvert. You might not know this about him. Like, he's like a very extroverted guy. He like loves those moments, but I think he's like at his best when he's like in a small conversation with one person or writing and by himself. He's an incredible— like, uh, it's gotten me to rethink about how I, uh, how I analyze people. I spend a lot of time thinking about like the qualities that define different people, and he's like, at his core, I think, an introvert. That's why he left, that's why he left San Francisco years ago. People think he's in San Francisco. He hasn't been in San Francisco forever because he left to go to Truckee so he could bring in people and build deep, deep relationships with them. I think that's like, it's really easy to sort of mistake this like brand and this persona for what is actually like very thoughtful, very focused time with individuals. And it's easy when you're like thinking of yourself, when you're thinking about somebody as like a shark on Shark Tank, like he can get joy out of those moments, but he's really at his best when he's like isolated and focused and with somebody like this. Yeah, yeah. Oh, anybody else want to come in? Somebody else dial in. Show callers, accept. Patrick, see if we can get you in before we get, uh, Eric. Hey dude, how are you?

Good, how are you, Matt?

Hey, thanks for being so active, by the way. You're always, uh, you're one of those people I think that's really active in our, in the mix, and it's sort of the lowercase ecosystem. I appreciate it.

You got it, always trying to, uh, add some value where I can. So let me pull up, I had a couple questions for you. You, I think some of you, you kind of touched on what was the one skill that you brought from CAA that's helped you the most at lowercase.

Um, the one skill Skill follow-up. I built like a really crazy system for follow-up. Even at the volume that I'm at, like things are falling through the cracks every once in a while and I need to improve on it, but people really care about follow-up. Leaving people hanging is like the worst way to— is the easiest way to piss people off. And so even if it's a pass, like following up in those moments, I screw up because now like My inbox is a damn war zone, so I need to get even better at it.

I can only imagine.

I'm always working on it, but that and knowing how— the other thing is knowing how to apologize quickly, I think, is one that gets underrated. When you fuck up, be quick to say I'm sorry and take the blame for yourself and not pawn it off on other people. I'll do that all the time. I think people— I screw up all the time. Like, I'll miss something, something will drop, I'll put something the wrong way, but like, I'm always the fastest to just take it on the chin myself. And it's something that I advise to anybody that's ever worked with me or for me is like, I will never be upset if something gets fucked up and you take the blame. Just be quick on it. That kind of expectation management, people can forgive really quickly. The second you try to defend or obfuscate or like throw somebody else under the bus, then we have a real problem. The last is like, CAA is a service job. It's really easy to think about venture as a buying position. Like, oh, I'm in here and I've got a checkbook and I'm like the one slinging out checks. And it's the opposite of that. Like, the second you believe that you are the buyer and not the seller of services, then you are missing this job. I think that's the fastest route to to people failing in this ecosystem is like getting, believing the check is like the most important piece and not treating it like I'm of service at all times. I meant it seriously when I said like, when you write an update, that update needs to be like treating your investors like employees. And so I treat like this job, like I'm of service to everybody, to my LPs, to my companies, to my partner, to people in the ecosystem whenever I can help, even people that aren't like investments of ours. I care about treating everything like a service job and being proud of that. I'm not— I don't treat it like, oh, I don't treat it like a chore or a burden. I think about it like that is a— that is an okay and a proud thing to be of service to people.

Yeah, I think that's cool. I was surprised by When you talked about asking for specific things from each of the investors and treating them like employees, that was an interesting insight to how you suggest a startup founder should be leveraging the investors that way.

Yeah, like I've had a couple founders over the past few years like thank us for investments. And I kind of always, I kind of flip those moments like you don't need to, like that's not a thank you moment. That is a like, okay, now you've just been hired. Like, like, right, um, yeah, it'd be, it'd be weird if you gave a job, if you gave somebody a job and said thank you. Does that make sense? Right, yeah.

So if you, if you couldn't be on the investor side of the table right now and had to go start your own startup, is there a certain space that you're most interested in or intrigued by?

Um, live video.

Okay, just like Vlad?

Yeah, I like, it's just an area I've always been passionate about. Like, these are the products that I tend to gravitate towards. I love meeting new people online. Like, I've gotten to know both of you guys through stuff like this, and I think this live video space is one of the most intimate things we've created as an internet. And so, I love the idea that I can get to know people through these channels. And so, I think there's still a lot to be done in terms of how to meet people, and how to interact with people in live and the kinds of formats that are being created and like the spontaneity around like building trusting relationships with people. Like you and I have never put a face to it. Like this is the first time we've talked, but like, I know who you are. We've had these interactions before and live still makes this feel like an infinitely more intimate moment for us. And so that's stuff that I fricking love. And I think it's like, we're just getting started on in terms of how to build new relationships online. And I think that like, Live will be at the core of that because this is fun. Like, we get to talk and have a conversation. You're in my living room. Like, welcome to my house.

Jam chest for the win. Yeah, love it. I had a similar experience with Anchor. I've been playing around with that a little bit.

I love that team.

And it's been interesting to have voice connected to it and get the inflections in it, and the personality comes through a lot more than, say, just tweeting at somebody.

I love that team, and that product's been really fun to watch that evolve over the last 6 months.

For sure.

Cool, man.

Eric, I'll throw it back to you.

Thanks, dude.

Yeah. Appreciate it, guys.

Thanks.

Matt, do you have any systems for following up with people, or are you just sort of—

I have an email system. Jackson and I work pretty religiously around a tagging and urgency system. So like, if something comes in from a founder, click urgent if something comes in from Saka, click urgent if something comes in like from like a trusted source, click urgent. That's the stuff that I get to first and sort of try to plow through all of that. Again, like I said recently, my inbox has been an absolute war zone, and so I'm not as good on it right now as I want to be. But inbox management is still sort of like, unfortunately, the my work list.

We'll take another call. Accept. Jason, welcome.

Jason Meeks, it's also another person that's in our world. Somebody wrote, thoughts on the future of conversational commerce? I'm hugely bullish on it. I think that like you're— I do this thought exercise with people, I'm like, How many emails would you say you open of the emails you get? Most people are like, oh, like 75%, 80%. And then, you know, some people say like, oh, how many, you know, tweets do you respond to? Oh, 75%, 80%. And I ask like, how many text messages do you respond to? And the answer is like 100%. Every single person, you get a text, you keep that SMS like box at zero. And so I think text is actually like one of the most underrated channels for distribution, which is kind of why I had this thesis a while ago and that's why we built lowercasealpha over SMS and not over email and not over some other channel because I just believe that if you do it right and you're conversational with it and it's opt-in and people can do it through that medium, text is going to be the highest converting channel possible for a lot of products. App downloads happen to be one of those. I'm firmly bullish on the idea that conversational commerce will be a huge opportunity. And it's not just for sales, it's for customer service. We have a company called Digital Genius based in New York that ingests all the chat logs of a company's customer service and then creates an AI-powered sort of chat log for people so they can interact quickly and immediately and get all the answers they need through customer service over text. Jason, what's going on, man?

What's up, Mazzeo?

How you doing, man? What's up, Eric?

Um, it's good, can't complain. So two things. First of all, uh, when can we expect the GoPro Skiing Remix? And second of all, um, I'm on lowercase group as well, and I was curious about the latest, uh, the latest product is Rex, and I'm curious what specifically you guys saw in Rex that, uh, jumped out to you that you wanted to get involved with.

Yeah, um One, thank you for being a part of that community. Two, all that feedback goes straight to the founders. So like anytime you have a product thought, if you just text back your thoughts, they'll get that note. So appreciate any feedback you have because you're part of that world. So Rex is one of those companies that I just— Chris and I had kind of been looking for forever. I think people have tried to identify like product recommendations for a long time and built things like OpenLikes and like If you go back and look at the products that I liked and the things that I liked on Facebook, it's like the worst representation of all of my favorite things. It's been butchered by years of like, was I liking a page or was I liking a product? I think that this world of like, I want to recommend products has been taken from a bunch of different angles. People have tried to do it for commerce recommendations, like my wishlist, and nobody ever thought about products as like social in my mind. And so, and everybody that's ever tried to do this that I'd seen tried to like ingest the Open Graph from, or the, the, the Like Graph from Facebook and automate like, here are all the things that you like. And it's just the worst representation of me. And so what I love was that they took this cue of like, we need to create a visual social network that the products that you love are actually some of the best definitions of the person and, uh, and do it in a way that was like visually pleasing and like felt like its own social graph. And so I started playing with Rex, and I was like, if you go through my Rex likes, it's actually the best way to get to know me. You'll see books that I love, movies that I love. It felt like the kind of conversations that you would have on a really intimate date, loaded into a platform where you were constantly sharing those things. And it felt visual. It didn't feel just like a product. Nobody was trying to sell me on anything. And so what they did was they turned products into something that I would brag about, like a social currency. And like, I feel like right now still, the Rex Vault, the things that I like, that I have posted out there, are a really simple way for you to get to know me. And it doesn't exist anywhere. Like, I could talk about things on Twitter, on Facebook, and it kind of falls into this like milieu of like stuff that like, it's really hard to see the restaurants that I've liked or recommended, or places that I've, or books that I've read. I'll post it out every once in a while, but there wasn't a repository for it. And there wasn't a repository for me to save that from the people that I loved and respected. And they, they just knew everybody. Ashley Lent and Chris, the founders there, are like the most connected, interesting human beings ever. They know artists and writers and publishers and tastemakers and all these different people. And so they had the right combination of empathy, new product, not growth hackers who are going to just try to juice the community by pulling in like all the things you've ever recommended from Twitter and Facebook and smashing it into like one app. It felt visual, it felt fresh. And so we backed it. I'm excited for everybody to get to play with it. If you've been, if you're on lowercase alpha, you just got it. And in the next couple of weeks, they're gonna have a bigger launch. And so hopefully you feel the same and—

Yeah, it's been super cool playing around with it. And I guess one other question is, I've spent a lot of time in San Francisco and LA myself. I actually live in San Diego, so I spend some time up in LA. But I was curious, you seem to have a good perspective on both scenes. What's one big difference that you see between the LA tech scene and what's going on in Silicon Valley up in San Francisco?

I love the LA tech scene. I think, here's the difference. So San Francisco for the last like 7, 8 years has built out all of these platforms that enable us to have these huge social graphs, right? Like we build massive distribution channels. Facebook, Twitter, Instagram, you know, all of those platforms have enabled us— YouTube— have enabled us to reach out to huge swaths of people really cheaply, mostly free. The best people for those platforms are great storytellers and content producers. That distribution pipe was built for LA. All of those distribution pipes were built for LA. And so the people Yes, the platforms all exist in San Francisco with the exception of Snapchat, which is awesome, but most of the people that have the biggest distribution live in LA. There's a place, if you've been to Hollywood, there's a place on Vine, literally on Vine near Hollywood, that is home to all of the biggest Viners on the planet. They all live in an apartment building together on a floor. It's like Shahidi and King Bach and like Rudy Mancuso, like the channels for distribution got built in San Francisco, but they got owned in LA. Like they got the, the best way to reach out to that community is to be in this community. Um, and so I think that's a huge difference is the people in LA are just natural storytellers and know how to use those platforms to tell narratives and to build audience. And so I'm excited to see, uh, I'm excited to see sort of like the products that come out of here. Also, you have things like, uh Snapchat, you have great commerce down here. We have an amazing manufacturing and arts district. We backed a company named Lumi, which is creating all these custom branded supplies down in LA. There are all of these different categories happening here. It's also more affordable. I like the social scene better. I like the food here better. You're never gonna find a bigger fan of this city. I think we've got a great ecosystem growing up here.

Seems like it.

I believe it.

Cool.

Thank you, Jason.

Yeah, thanks, guys.

Take it easy.

I got time for one more, Thornburg.

All right, one more. I'll give someone 30 seconds to call in, and if not, I will ask the last one.

All right. Jason, thanks for being a part of it, dude.

Perfect.

We got it.

One sec here. We got a couple callers. All right, we got Gregory. He called a little bit first, so I'll get him first.

Okay, Gregory.

In the meantime, I have a quick question. Yes. When you've made, uh, when you were just starting out and maybe you made a mistake on an investment, or, you know, looking, looking back What mistake did you, if you did make one, what was something you realized, oh, I shouldn't have done that, I didn't see this about the company, or something that you—

Okay, yeah, that's a good one. So I have a bunch of flaws. One of them is that I get super excited about a business potential, right? Like, I'm a crazy optimist. I'm like the furthest end of the optimist spectrum. But also, like, sometimes you see the world with a founder and you're like, they'll identify a problem set and you'll start playing into the hand of the founder and start like imagining what your solution would be. And so sometimes at Seed, especially if there's not like a defined product, sometimes we're really early in this. The earlier, the harder— the easier it is to make this mistake. Where you will imagine what you would build as the solution and start like filling in the blanks that exist in a founder's pitch with your own belief or your own projection of how the future is going to work. And when you do that, it's really dangerous because you start to like direct your vision towards like what you believe as opposed to like letting the founder really explain how they believe it. I get excited about a product, I'll dive in, I'll be like, yeah, that's amazing. Here's a way that you could build in the future. And it's really easy for the founder who's, who's at that moment in time raising capital from you to say yes. And when that happens, this disconnect create is created in terms of what you believe the product will be and what they believe the product will be. And so sometimes you have to temper your excitement in those moments and not fill in the blanks no matter how much you want to. Uh, and I made that mistake a couple of times early and what it set up was like a world where like, hey, aren't you building this? And the founder was like, no, this is actually the bigger priority. And it turns out that in that shift, I probably wasn't the best investor for that business, right? We didn't have the same belief in where that product needed to go, and so I couldn't be as helpful as I wanted to be. And that led to problems. Even in success, it was just like I wasn't the investor that I wanted to be for that company because the value that I thought I would be able to bring wasn't where the product was heading. And so it's not that the company's necessarily failed, it's just that I failed in what I would expect myself to bring to the table.

What's up, Gregory?

Hey, how you doing?

Where are you at right now?

Hey, Matt. I'm in LA. I'm in Glendale.

Yeah, the promised land.

Yeah, absolutely. It's nice to meet you guys. I actually came across with Protocon very like accidentally a couple of days ago, and the first thing I came up with was this video chat session. So I go like, you know, I frankly speaking, I never knew Matt and Eric.

Cool.

I just knew Lowercase Capital, and I know Chris Saka, I follow him on Twitter, and I've been always, you know, been interested in actually learning more about Lowercase Capital and trying to, you know, present you our pitch. But later when I actually went on your site, it sounds to be a really, really interesting company. I mean, it's a very creative venture capital firm in my opinion. And your approach is also very creative. But one thing that I actually joined today to ask you a question about is you mentioned that Basically, pitches should be addressed through an email, as I understand. But Lowercase Capital states that turns out that you guys never end up backing a company that approached you through email. And also, your website states that you guys don't accept any pitches or you guys don't fund any companies that came out of the blue. So you prefer some kind of a connection. So what's my question? My question is for a guy like me who works day and night on a startup, who has a big dream and is a dreamer, you know, how do I approach lowercase capital if I don't know any connections, I don't have anybody? Meaning, I mean, I know a lot of people in tech, but not necessarily like my people I know don't know lowercase capital. I mean, they know the company, they don't know any people out there. So what are the chances for me as an entrepreneur who's been, you know, working very hard to, you know, create his product. But so how do I present my pitch deck to you? And are there any chances? And what does it take to do that?

Yeah, so part of the challenge of working at the seed stage level, and with our fund, we're really, really broad in our focus, so our funnel ends up being pretty, pretty wide, is that we have to find signals in that to like identify potential opportunities. The best signals that we found just as we analyze that is like signals that come in from Matt Mazzeo, from, uh, before, who are experts in fields recommending companies in those fields. So it's just the best way for us as a fund to quickly segment out, hey, this is a high signal, it's from a founder in that segment and somebody they've worked with in the past. We have to use those tools, otherwise it'll be a totally blinding amount of information and I won't be able to sort of process any of that. And that's just a fact, I think, for almost everybody today. It's like, if I just came to you as a stranger on the street and said, like, I've got an idea for you, it's this business, and you never had met me before, it'd be really hard for you if that volume got to thousands or tens of thousands of inbounds, right? And so you'd eventually have to find those signals to work through. That's just the signal that we found. And so we don't— it's not that we don't take investment over email. It's that the best signals and the ones that get the highest priority are the ones that come through relationships that we've built inherent trust in. And that's just the only way we've found to scale with 2, now 3 people on the team. The way to break through that though, and by the way, it's not to say that we haven't actively gone out and found investments that came just from companies that we didn't have a direct connection to. Dubsmash being a perfect example. I didn't have a direct relationship with those founders. Everything falls by the wayside if you execute. So the other signal that we pay attention to is like, who is executing on products that we really love? And so like, if there's a product out there that we really love, turns out I just spend a lot of time in this world playing with products, like working on new things, like seeing, paying attention to the signals that come from my social sphere. And so Sometimes I actively find things. If you are executing on a product, it's not just that you're working hard, but if your product starts to get that kind of traction at an early stage, and it's an area that I'm passionate about, then I will find it, because that's the stuff that I love doing, and I just pay attention to it. And so you can start by being active in the Product Hunt community, by being active on Twitter, by interacting with us, by showing up to these Product Hunt Jams. Like, and also, like, I push back on you, if you really are active in this space, like, I'm a pretty open guy, like you can get to me fairly easily. There's a lot of people in this chat, Stefan included, Jason, you know, Eric Willis, like there are people in this chat that I hadn't met personally that started by adding value and being active in the community, and then I pay attention to those signals. But if you're just coming with nothing other than an ask for cash, and I have nothing to base it on, no social signal, no product signal, no traction, that will fall to the bottom of a deal flow pipeline, and I will miss things. I will miss good opportunities for good companies that hit me in that realm, because if I don't pay attention to those signals, I'll miss all of them. And so I have to ignore those things that don't hit some of those metrics. I'm okay missing some of those things, knowing that like, that's the best way for me to manage my flow.

That's a perfect answer to my question, Matt. I really appreciate that. I'll try to stay focused and I'll try to stay connected with you guys and see if, you know, something is going to work out. I'll tell you a little about, like, I'll just finish up my conversation by saying that I'm the founder of Forkspot. The company is called Forkspot.

So, uh, Gregory, you're breaking up a little bit, so if you don't mind, put it in the chat and I will go back and take a look at it. Uh, and I appreciate you jumping into this call.

Great.

Thank you.

Eric, thank you so much for giving me this opportunity to talk to you.

Thank you, Matt.

This was fantastic. Thank you for going overtime with us. I know you gotta jump. Uh, you are a friend, mentor, but one of the best guys in the business. Talk to you soon, bud.

Thank you, brother. Thanks, guys, for participating. It's super fun.

Peace. Everybody give it up for Matt. Take it easy, bud.

Later, team.

Alright, I'll talk to you later. Okay, everybody, thank you for coming on to Product Hunt Live. Matt is off to a call. Everybody who's got feedback, tweet @Mazzeo, @M-A-Z-Z-E-O. Let him know you love that episode. Let him know you're a big fan of Lowercase. Check out Lowercase Alpha, lowercasealpha.com. I believe I will put this in the show notes of the podcast and tweet it out as well. Yep, Jason's got the link. Mazzeo is one of the best guys in the game, not only talent-wise, but also one of the kindest and most respectful, and a lot to learn from him. This was a fantastic, fantastic episode, and definitely check it out. I have an earlier episode from Mazzeo a year ago. We got sort of smaller episodes, some of them into these things, but this is a much longer one. So definitely shout out Mazzeo. Thank you for another episode of Prodigent Live, and we will have more fantastic stuff upcoming. Guys, I'm inspired by this episode. Aren't you inspired by this episode? Doesn't it make you want to go do something incredible? That's the effect he has. All right, take it easy, everybody. I'll see you guys the next time.