#074: The Secret to Raising Millions: Insider Tips from VC Taylor Brandt

From an investor's perspective, what do you think about that? Like, if you were an investor in those companies, would you be like, like, I guess push towards profitability is good, or is that like a negative signal?

We have this odd thing now where like $100 to $200 million businesses aren't going public. And so what do you do if like you then start to meaningfully slow between that? You actually don't really have an acquirer set and then you can't go public yet. So As an investor, I would say, do you have competitors on your heels?

Mhm.

And are you still growing?

Welcome back to Season 3, Episode 17 of the Turning Pro Podcast. Today we have Taylor Brandt, who's a principal at Headline. Thanks for joining us today, Taylor.

Thank you guys so much for having me.

So I have faith in you and this conversation because you have operating experience in your background.

I will do my best.

Look, I'll be the first to admit, I think like talking to a founder is a very different conversation than talking to an investor. Just not to say that like everyone has war stories, but they're very different.

100%. Being an investor, you get to ride the highs of the founders, but you just feel the lows like a notch less.

More than a notch.

Like a couple of notches.

Yeah, because it's like when, when the highs happen, you're like more invested and all in. And then when the lows happen, you're like, oh, fuck.

Fuck. Oh, it's devastating.

Like, you—

like, I'm writing this one off. I don't— I'm not going to allocate my— no, I'm just kidding.

I'm there for it. But you don't have, like, the, the, like, heart palpitations, like late nights, like sweating, like founders do. I was— I was an operator who felt founder pressure. So then when I tried— when I went to go try to be a founder, I realized that I would just be like a paranoid, anxiety-ridden human being that would have no life. And so I was like, I don't think that's the best route for me, which is why when you meet founders who have enough confidence to not have that deep anxiety that I would have had, you're like, oh, this is like— you have to have some level of both, like, like ability to block that out to be great.

What is your perspective on just like investor-founder empathy where like there are investors who are very good investors who've never been operators before, like their ability to relate with what a founder is really going through? Like, it's one thing to say, oh yeah, like, I understand it. It's another to actually truly empathize because you've been there before. And do you think that has any impact on how you— your relationships with the founders that you're dealing with every day?

I think if you have never operated, uh, you can be an incredible investor, but I don't think you can have founder empathy. Um, and probably that even is true if you've never operated at very early stages. Because you just, like maybe if you sat in management and you had a big team under you and you had to go through rifts, you can feel it in a certain way. One of my portfolio COOs, like that was like the turning point. She was like, I was at a big company and like I had to let go of a big team and that was hard. That was super hard. And now I'm ready to go like, early operator path. But no, I think it's a really hard— I think you can't feel it. And I do think it's where I lean the strongest. I hope my founders would say that, like, Taylor is actually willing to, like, get on the phone with me at every hour, work through hard problems and, like, feel like— because I do feel it because I was an exaggerated operator. I do feel it, but I'm never going to feel it in the same way that they do. It's you, you have a lot of investors who cannot sit in that shoes and be like, do you know what it was like to quit your job and take, take a $50K salary and have a family to go start this company? Because I don't think they do.

Take me back to Rockets of Awesome where you were director of growth by the end, right? Take us back to that. And then also I want to hear about the decision because I don't know if we've talked about this to go into venture because I know you're doing some angel investing. But I'm sure at that point there were two paths in front of you. You're like, all right, I have a pretty senior level at a brand. I could go do another brand. I could do commerce infrastructure. I could just go start my own company. I'm sure there are a lot of opportunities there that you were potentially interested in. Why go the venture path full time?

Yeah, so I didn't— I went to Emory where basically everyone goes into banking or consulting or accounting. There wasn't really like the startup ecosystem and venture were like not a topic of conversation.

I went to Colgate, so I understand that. Yeah, same.

And so So it wasn't until I moved to New York that I like found the like venture startup scene and I was like, that's really cool. I think I'm in the wrong place. And so I started talking to people in venture and they were like, fuck off, you're an accountant, you can't get a job here. And so I was like, okay, I'll go operate. I was like very lucky to— I made some like probably very wrong operating choices. I've had offers at companies that are now very, very large companies. But I think those taught me by far the most. I got to work with amazing people. I got to work with serial entrepreneurs and operators who were amazing and got me exposed to an ecosystem. And so I was advising and consulting on the side at Rocket. Because the like Warby Blumenthal like network was like so ingrained and was working with a ton of companies both on infrastructure, tooling and brands. And as someone who runs an agency, you very quickly can figure out that you can run a marketing agency and do pretty well. And so I was like, well, maybe I should be on the side running a marketing agency and do that. I think the like masochist need to build for myself, like I was like, okay, I don't— I was doing it And then basically the month before COVID started, February 2020, I was like, I'm going to leave. I was planning to go start a company, but in the back of my mind it was like, if I don't find the company, I should probably parallel path to venture. At this point, I had started like helping companies fundraise. I was, I was angel investing. I was like a little bit in the ecosystem. And I was like, but I was like pretty set on like being a founder. And I think a little bit for the wrong reasons. I was like, people were like, you have the, like, there aren't that many like female founders with like the hustle and the grit and like want to get in the weeds. Like you fit the mold. But I didn't have like the company idea, the like passion project that actually made sense. And so I came up with a bunch of ideas. I talked to investors about them. They were like, yeah, go do one of them. Like, and I— and then a couple of weeks later COVID hit and I had only met— I had met two investors at that point for like venture dating conversations. One of them was Red Sea at the time and they were like, yeah, it's great to meet you. We talked about some company ideas, we talked about some investing ideas. And Paul and I started hanging out. And so I continued down the founder route as COVID hit. I moved back to, I went and stayed with my parents in Florida. I was like grinding on ideas. I couldn't find a company that kept me up at night. And what's funny is every single one of the companies has been created. And all of them are okay. And none of them are great. And I think that that is like very clear that like, none of them were the right thing for me. And a lot of those founders that I ended up meeting had the better founder market fit than I did for those specific ideas. I didn't have the right co-founder, and I actually thought I'd be kind of a miserable person. I was like, I'm going to end up alone in my parents' basement building, like building a small company. And that sounds not so fun. And I think today I would feel very differently because I think I'm like a happier human being. But I was like just working around the clock. And so Now, and just trying to prove that I was worth something. Like I was just, I was just like, will people value me? Like when I started consulting, I was like, just let me help work for free. And then like all of a sudden people were like, we'll give you $50 an hour, $200 an hour. I was like, I can make money. Like who knew? But at the beginning it was just to like prove that I had value, I think to myself. I think I now feel that in a much different way. And now if I went down the founder path, it would feel very differently. But at that point it was for the wrong reasons. And so, um, I ended up meeting Paul. COVID had started, so now no one was hiring. So this is before— I think everyone forgets that before the boom, we really had the bust. And like, no one was hiring, no one was investing, no one knew what they were going to do with their firms, and no one knew if everyone was back in office. So like you were talking, like I was talking to firms in the Valley and they're like, well, are you moving here? But we can't even have you move here. Like, what's the situation? And I was really lucky because I had talked to many, many firms that like great dynamic with, still have relationships with to this day who weren't ready to make, pull the trigger. And Paul and Scott gave me that shot and said, hey, just like, hey, let's just start, start working together and see how it goes. And and was amazing and was an amazing experience for me and got me, and was absolutely the right decision for me.

Yeah, I do wanna talk about one side note there about being really passionate about a pain point or the idea. I'm sure you've gone through this too as Platter's now serving huge enterprise customers and maybe a different ICP than at the beginning. I think early on, the first year or two of a company, you do need to be absolutely obsessed with that archetype of whether it's a founder or head of sales or whoever you're selling into. But I will say, at least my experience at Verbatim, because it's my first company, like I needed that obsession the first couple of years. But after a certain point, you're just going to have different ICPs. Like you may be like, hey, this business isn't scalable selling to this ICP. We need to go sell to this ICP. And like, as we've gone into enterprise now, at first I was just like, I need to help a pre-seed, seed stage, like B2B founder. We still do that, but only like 50% of the time. And like to build a really big business now, I need to solve the head of content at a Series D. Specific pain point. And that's like not the original archetype that I actually wanted to help out. But I think over time you fall in love with like the process of building a company and you actually like really like the craft of business building. And so I think over time, like you do need that obsession. But once you start like enjoying the craft, then you can— it doesn't matter who you're selling to as long as you like, like, like the craft of company building.

Totally. I think there are like— it's funny that that like obsession thing is also like serves on the investing side. There is, there is like an adjacency away from like your passion that I can invest into and like a standard deviation away. But 3 standard deviations away, I meet a company and I'm like, I'm not the right investor. I'm like, you might be. I'm like, I can, I can look at it from like growth investor, like eyes. And be like, this is a great business, but I actually don't think like I'm the right fit because if I can't, like, if that company doesn't keep me up at night, if that business model doesn't solve something that's like interesting and like believe wider, just like in just some sort of way, I'm like, I have like, I sort of like go through a checkbox for myself. I'm like, am I the right investor fit? Is there an ethical fit? Like, and, and is the risk reward there? And if I can like check all of those, like I can get, get over the finish line. But getting to conviction is the hardest part. And if it's like off, if it's something I truly cannot even like get excited about and keep me up at night, it's just not.

Are there instances where there's businesses that you're attracted to and you see like the outcome potential of some business idea, but you just don't feel like it's in your lane? And you just have the humility to be like, this is awesome, but I'm not the right person for you.

100%.

What, what are like the characteristics that you look for when you think about what suits you best as a, as an investor?

Um, I look— so I, I've like built— most of my investments like fall under, um, a category of like sort of take it back coming from the commerce side and then coming up. But like being someone who's obsessed with like data and infrastructure and tooling, I like almost went down every route. I was like, I went, I was like, should I be a data infrastructure investor? Should I be a consumer investor or should I be— and like once I started investing, it was like very clear. I like clearly liked B2B software the most. This goes back to a little bit of founder risk. I think that consumer is more risk-on versus like finding diversified risk. I loved, like when I started operating commerce, we were built on Solidus, everything was point solutions, watched as Shopify like ripped through a generation, had friends building in a B2B marketplace. And I was like, oh, I think we're gonna see the world of like vertical software and commerce and global trade start to shape differently. And so most of the things that I look at either have vertical SaaS, procurement, marketplace, or commerce infrastructure, which includes like supply chain and enablement of those layers. I tend to find, and so like there's a lot that fits under there. Like I get nerdy about a weird like niche industry and like want to understand about like bioinformatics or something like that. Like if it's weird and nichey, there's a lot of like similarities between vertical software. But, I, outside of that, infrastructure tooling, I very quickly found like I cannot, I can look at the numbers and know that cybersecurity businesses are great. Not it, even if it's on the app layer for me. Super horizontal businesses where there's like a lot of competition. I think that they're just hard for me to like find the like why is this, the winner. So I tend to just bow out. I'm like, okay, unless you have like, you wedged in through a certain unique customer base, like I'm just not the person that can like, that sees it that clearly. And yeah, you need a certain gut for consumer that I don't think I have.

Very fair. I have a question about investors more broadly. 'Cause I started in venture, I had no idea what I was doing. But coming from that space, I was like 22 and 23, and I think I was just like younger and had more of like a hustler energy. And anyone that pinged me, I'd respond within like minutes or hours because I just had nothing else going for me. And so I was like, I got to do this. Now running companies, we both are responding to each other in like minutes via Slack or email. Even people that I don't know, if I do want to respond, it's usually going very quickly. I think most founders that are like on it, that is usually their default response. There are— I can name like a couple investors, yourself included, where I'll text you and you'll just like call me immediately and you're like, what's up? There's a weird transition that I've seen of like career VCs as well as founders that used to respond to me that way that are now VCs that not just the classic, like I'm on vacation, but sometimes they just won't respond to me and I'll send them like a great deal or a great founder and they'll get back like 3 weeks later. I was like, oh, I'll take an intro.

Why?

Why does that happen? Happen?

I can tell you why that happens. You can want to be like all of the things that I think every VC says they are. I think there is some diminish of scale. Like VC is not a scalable asset class. You are committing your time to companies over sequence of years and you giving more to your portfolio versus new companies has trade-offs. So when you're a first-year VC or your third-year VC and you are not managing that portfolio, your job is just to find companies and talk to companies. All of a sudden those trade-offs become like very clear where you're like firm, like firm things, LP things, portfolio things, and then deal sourcing becomes the last one. And I give so much credit, like, looking back at Red Sea, I understand why seed funds, like, are the hardest because you're doing that predominantly yourself, like, all of those jobs. And so, like, I'm very lucky to have an analyst now who I, like, wholeheartedly trust and, like, would, uh, can really lean on for, for the deal side. Because when I was at, like, when I moved to headline, I was like, zero shot will I let anyone talk to a founder before me. I was like, this is a me thing. Like if they're choosing me, they wanna work with me. But now I understand like you do, you have to make the assets scalable. You have to figure out where to draw trade-offs. And some of that is where you just like have to just like ruthlessly prioritize. And Sometimes that's also prioritizing yourself at like night. You're like, I could go like clean my CRM and respond to all the people that of the meet, like of all, if you were in back-to-back meetings all day, all the people of emails that I got that day, or you can just be like, I need this time for myself. And it feels really shitty, but then you realize that's also where people burn out and where founders, and like, I think you'll, you see it where founders do this the same way, but they do it with a team where they can, sort of start to trade off.

But I'll play devil's advocate there. You respond within an hour most of the time. Paula at Red Sea still responds within an hour.

Yeah, but all because she responds to you quickly doesn't mean she's responding to everyone quickly.

Yeah, there— you don't want to see my unread emails and text messages.

I think my, my one thing I'll add to this is you're in a very different seat as an investor versus founder where like if you ignore something as a founder, shit can go south really quickly. If an investor doesn't respond to an email about like a new deal, sure, that company might go on to be like a unicorn, but that's not going to be like the make or break of your fund and your job. So I think that like the stressors that are urgent are very different for an investor versus a founder.

That's fair, right?

Like when someone at your company pings you because you're your business went down, or like a client's pissed or whatever. It's very different than if she gets an email from a founder who's just like, oh, I'm frustrated, like I can't get through to my co-founder about this thing or whatever.

If my portfolio texts me, like if they don't hear from me in 30 minutes, I would be upset. Um, that is also true of people that I am close to and trust. Um, that is a, that is a like a small circle, like of people in venture, of like people that I am like I will go, I would go lose the deal to you and I would kill for like, they're like my people. That's not everyone. Like, I think at some point you realize like it's still a transactional business in some sorts, like it's a human business, but it is transactional. And you realize in some cases these are like business relationships and the people who are like my inner circle, like I will like immediately get back to them. But you actually risk like you tend to get into venture because you probably, I won't speak for, I'll speak for myself. Like you probably have some form of ADD or ADHD where you are like, are good at contextual switching. You're probably like high EQ, IQ and have like this contextual switching thing where you can't stick to things for too long. It's hard to say no to that email. Like it's actually, it's actually harder to ignore that email than to spend time focusing on the deal that's active. But if the deal that's active is the deal you're trying to get done, if you're going to do 2 to 3 deals a year, like that's actually the most important thing in your active portfolio and everything else is like moot. And, and, and so I actually give a lot of respect. I texted it, I sent a deal to a friend and she was like, I'm active on something, like I can't. I was like, I was like, respect.

Yeah, she takes the time to at least tell you that, which is awesome. I'm curious your perspective on just the venture landscape over the last couple of years. My perspective as a founder is that the barrier to entry has become so low because people can just find like one rich family office and all of a sudden they're an emerging manager. And so I think there's been a lot more noise that has come into the ecosystem, which makes it a lot harder for founders themselves to sift through their own level of bullshit to know like, is this actually an investor that I even want involved in my business? What's your perspective being on the other side of the table?

Yeah, I think that will get much harder than it was. So I think that, like, um, I think we will see, uh, very quickly, like, not that many emerging funds stick around. I think new funds starting today, uh, will have to have had quite a track record, um, to have built that fund. I had friends who went and fundraised 2 weeks ago, and then they called me and where like, I have a term sheet from a VC that I had never— I'd never heard of the fund. But then he was like, oh, it's Fin Barnes Fund. And I was like, oh, like, of course he could raise a lot of cash, like 100%.

Yeah.

And if you, if you leave and everyone knows his name more like who— like they're like, that's a good investor. He was a great investor in first round. He was there for like nearly a decade and then went and started a fund. I don't think that it will be easy to start new funds. I think if you are raising a seed round, you to have a fund, like if they have raised $40 or $50 million, like that's not a small feat. I think smaller than $40 to $50 million funds are hard to keep going. And so you're gonna see that. And you see, so new fund managers, Fin, if you talk about like Taylor and Byron at Twelve Below and you see where they got like, Did it have large institutionals attached? Like, it's very clear, like, those are not one-and-done funds. But it's all through reputation. I think that, like, the small fund managers that, like, get into a lot of deals do it all through word of mouth. And I think just, like, really looking at their portfolio and asking their founders, like, How did you find them? And seeing their fund size. I think if they have been able to raise a quantum of capital and/or raising a second fund is not trivial. So if they've done either of those two things, like I think they're doing something pretty good.

Are you planning on being in venture for the next couple of decades? Like, are you really invested in like the craft of investing?

Yeah, 100%. I think there's, I get asked like fairly frequently why I haven't gone the founder route and/or like drawn to the dark side of like an executive seat. And I love what I do. I'm lucky because most people when they get recruited in adventure don't, like are told something and something else happens. You're going to get promoted. You're going to have this happen almost entirely. That has been true at Headline for me, where I've had an amazing opportunity to go like find who I am as an investor within their brand and within their like collaboration and friendship, but like also giving me room to be me, which I like love. And I think they know in some room of me being me is like an entrepreneur. And that might not look like at Headline, like we kind of joke, we're all like a little bit different. A couple of my colleagues were at my wedding this week and they were like, people kept joking about your weird sense of humor, but we didn't really know you had that. I was like, oh no, I think I'm just Headline weird. Like, I think we have like, I fit the brand of weird and I think that they know that like part of that is that I'm like an entrepreneur at heart. And that might look different in the way that I operate in the fund, whether that's I want to incubate something, whether that's I want to do a deal that looks a little bit different or a little bit misshapen. I think that they're okay with letting me like thrive under that umbrella. I think that's like the main reason that I've continued to feel that passion. And I have amazing portfolio companies. Like, I could not ask for more and love working with them.

I have a lot of friends from college. I'm curious if you've had this experience of like people used to be friends with that went into like IB or consulting, are finishing up business school, maybe did private equity, hedge fund again, and now are getting into like early or growth stage venture. And I've caught up with a couple randomly over the past few weeks that I went to school with and just talking to them, I'm like, why the hell are you in early stage investing? This does not fit your personality at all. You don't have like an entrepreneurial bone in your body. I don't understand how any founder would like trust you or want to work with you. Like, why is that happening? And what do you think is going to happen to those people?

I, I think growth is a different animal. I have amazing growth colleagues who like I learned so much, but they I think you can be an amazing growth investor with a different, like, without the same, like, I need to have worked in a company of 5 people and know what that feels like. You— so growth, I put in a different landscape. I do think we're seeing more of the private equity and venture start to collide as an asset class and get way closer together. So if you think about that, it actually, it actually takes more operating experience to go like private, like buy out a company and then put in new executives like that. Actually. So if you think about those, I think of them sort of in parallel. I think that starts to look different C and above. B starts to be the middle ground of like, there's still some shit going on at the Series B, like at Series B, you're like still figuring it out. And I think people underestimate that and think it's like a de-risked asset. I think at Series B, you're like, Yeah, momentum is in your favor. Something is working, but like things are still being figured out. At C, it's starting to like have become like a mature company.

And at D, it's like, like probably actually real data that you could actually look at by the time you get to Series D. That's why, like, what you're just talking about is you went to banking for 2 or 3 years, you went and got your MBA, and now you're telling me that you're like a pre-seed investor? Like, how many models do you want to look at of a company that's like pre-revenue or maybe doing like a little bit of revenue to be like, okay, yeah, like their economics check out.

I think they're going to just dislike the craft. I think venture, like, was like people thought it was a cool job, definitely cooler. My husband is a corporate lawyer. And if you think about like jobs of like smart individuals that like it seems cooler, but it's— there's like, I think people just don't like— many, many people told me like, I don't think you'll get a job in venture. I don't think you'll do well in it. You have to like overcome that to get into venture. But the reality is those walls that are put up, I actually think need to be even like even firmer of like there's many things about this job that are not fun. And most of the job, like the networking social VC is not like a— like is not the job of venture. That's actually probably the thing that you're just doing in your own free time, like at the time that you're doing your— you feel like that is a pressure you need to do alongside of your full-time job. And you need to like stay in the flow and still be in like getting deal flow. And even when you're active on live deals, like it becomes— and like you have a life and a family and maybe all of those things, it just feels cool and fun in your 20s when people are like, I think that sounds like an interesting job that I'm not behind a desk 24 hours a day. And for sure is probably more fun than being a Goldman banker. But I actually think being a Goldman banker has like might be more transferable if you're like a first-year venture person. Like it's not you, but it will teach you what you do. Figure out what business models start to work. You see enough pattern matching that like if you want to get into venture out of like and you just want to like see a lot and then go operate, I do think it tells you what company to then choose. Like if I knew now what I knew when I was going into operating, it would help me find the right company to go work for.

I think that's an interesting perspective though, because I feel the same on the founder side of like being almost 3 years into this journey. What I know now about like investors compared to what I knew like on day zero of the company is so different. And I think I would have approached just like the conversations I was having and the way I would have gone about it had I known. But like the only way you learn is by doing. Yeah, right. You're falling forward and just like learning from experience. But I think, I think venture is very much glorified in the worst way possible where there's a lot of naive people who are like, oh, so you're telling me that I'll just go get like a couple million dollars and like go hang out at you know, private events and just throw big checks into companies that are ripping, and then I'm going to be rich one day and retire. Like, that's really what I think a lot of early-stage emerging managers think.

Yeah, I think so too. And I think emerging managers— like, when you think about— like, you have two ends of the spectrum in venture. You have— I'm like, gonna get hurt— but you have like Andreessen Horowitz on one end, where you're playing a management fee game, where you're stacking management fees, and you're returns, like, might— like, can you deploy that and still drive the returns they did in their heyday? Or you have like solo fund managers who do that, who actually know what they're doing, know that they are doing something that is going to be painful. Because if you actually just think about the economics of 2% on a $20 million fund where you probably give people a discount on that 2% in, in, in your first fund, and then you have to do that to pay your lawyers and pay your accountants and pay for your office and do all that stuff. Like your salary at the end of the day is for sure lower than whatever you were doing before. And realistically, most people who can do that either have already seen very large success and therefore probably can, like people want to take their money because they are, have founded something or been extraordinarily successful. Or they're naive.

There was a tweet from Andrew Chen from Andreessen like a few days ago. I think they're doing some like accelerator sprint program. And what don't they have? I mean, they got a lot of employees now, but he's uber more experienced than I am. And maybe I'm missing something, but the tweet, it got like thousands of likes and it was like, we're giving $30 million away in the next 3 weeks. I don't know if you guys saw this. I was like, I don't know if I'm missing something here. That seems like a weird use of capital.

I think that, I think that there's a lot of ways to make money. I don't think that there's one way to drive a 10x fund. You could have a zero loss ratio fund that like every deal is like a, like you can, you are so consistent. You have a gangbusters one deal. The like Y Combinator has many, many companies that do not work and or people just took the money and, and like had a little pet project and it, and it went nowhere. But the economics of what they get in on are so large. My, some of my portfolio companies, I look at their, their pre-seed rounds or their friends and family rounds and you're like, wow, those people are, are doing really, really well and we're hitting the B and the C and they can take liquidity. And so I think that like, no, I think when you're playing in $30 million in the Andreessen fund size, it's not going to drive the fund. Like it's a, it's just a funnel. It's like marketing.

It's a, it's a, it's a marketing budget.

Marketing budget.

$30 million. Yeah. But their, their philosophy on it is this $30 million marketing budget is going to get us 7% of 20 more companies that maybe we wouldn't have gotten before, and 2 of those are going to go on to be billion-dollar companies and we're going to make back 9 figures on this $30 million marketing budget.

If you—

they're just playing a different game.

Yeah. If you like, they're— I am sure that their goal of $30 million is to then write X check after that. And so it has to be that if the $30 gets them $150 million deployed or something like that. And that's how I would think about it.

Yeah. I want to talk about like new models of company building because I initially wanted to go like raise venture, did not go that route and things have worked out. I have a lot of other bootstrap friends that are building like pretty sizable companies. You and Cyrus and a lot of our friends went the let's raise small rounds, but still like multimillion dollar rounds from angels, maybe really early stage funds where you have a bit more optionality about, okay, things are really working. I can go raise $10, $20 million, or I can kind of keep going in this path. Why are those getting more popular? Are you seeing like pretty serious entrepreneurs now going down that route?

I'm going to add one detail to further clarify that. Software businesses that are building in the services revenue component earlier in the lifecycle than I think we've seen in the past.

Yeah, I think that, um, we got a lot of tourist founders when capital was flowing freely and saw friends that got quick liquidity, found success, took money off at the B, it was fun. They got $10 million in their pocket. And, and, and you saw a lot of tourist founders that were like, that seems cool. And, and I, And no offense to the males in this room, you also saw more in men. Where I think like, I will say as a woman who was in those shoes, like was more, okay, well, like, what if I do this and it doesn't work and I want a family and all of those things that went through my head at the time. I think that now you're gonna see, like, we're seeing more of like, two definitive directions, which is like, I am all or nothing. Like, I am going all in. Justin, the founder of RepRally, like, you meet him and you're like, that is someone that wants to build a multibillion-dollar company and would rather like just not have a business exist for it to be a middle or company. But middle or companies for venture are generationally wealthy people. So you sell your company for $300 million, you are generationally wealthy. And I think we're coming back to that reality of people actually understanding that. So I've had founders who have gone down the path of until I am sure I'm not going to raise that very large round. And once I'm sure and I'm committed to that, then I go raise the very big round. And at every, every round you close one door at a pre-seed with angels. Like if you get a $100 million option on the table, they'll, have that conversation. They might not say yes, they might not agree with it, but like the conversation will be had. If you raise your seed round, the couple hundred million dollar outcome is still a discussion. Once you raise your Series A and definitely once you raise your Series B, like doors start to close for what your optionality is on sales. And I think founders should be more thoughtful on when they make that decision. I think venture capitalists need to deploy dollars and I think we're seeing the trade-offs between that where they're saying, well, I need 20% of your company. But at the same time, like, uh, I have a founder in my portfolio who his first company didn't succeed. So because of that, he was like way more thoughtful in how he deployed capital, found product-market fit, hit scale, and then was like, okay, like, now I'll go raise a Series B. Um, and, and, and I deeply respected that choice. Now, that founder tends to look a little different than the all-or-nothing founder. And the all-or-nothing founders have a lot of zeros and also some really, really big wins.

But when you say the, like, venture based on unit economics typically has to overindex on like the all-or-nothing founder to get like the returns that you're wanting. Or do you think now in the market with so much capital that funds need to deploy, they're actually willing to invest in companies that might have like a $200 million outcome versus, you know, the unicorn business?

Um, I think there's a difference between Adam Neumann, Travis Kalanick, Brian Chesky. Like, I'm not putting Brian in the same category, but like, you go big and you go for a business model that is hard, complex, like, and, um, like And those outcomes are not billion-dollar companies. Those are tens, like tens, twenties, thirties, $100 billion companies. And we are gonna continue to see bigger companies than ever before. I actually don't think you necessarily need like go big or go home to see a billion to $2 billion outcome. I actually do think there are, there is a, I found a market, that market unlocked for me. And actually like that compounds on itself and you start to see those outcomes. Like I could name multiple in our portfolio historically that that happened for that I would put in those $1 to $4 billion companies. I think when you start to see the larger than that, it probably was a pretty crazy business model and like you need a, you need a, like Jeff Bezos did something extraordinarily special and unique.

And yeah, I'm curious to get like investors' take here. I feel like over the past few months I've been seeing more founders post like, we're profitable and never raising again. I don't know if you guys seen those on like Twitter and LinkedIn. I think like Fondo posted one of those, like the tax and accounting one. Meow, I think posted one of those like, we haven't touched our investor capital and we're profitable and we're never raising again. On one hand, like I'm a customer of Meow. I think they're awesome. Heard great things about Fondo. From an investor's perspective, what do you think about that? Like, if you were an investor in those companies, would you be like, like, I guess push towards profitability is good, or is that like a negative single signal?

I think there is. I think that the public markets like value rule of 40. And so if you can grow without, without that without using capital? Sure. I think that if you can't grow and sustainably, like if you look at most of the, it's not like these companies are just pouring capital in and then not seeing best-in-class payback dynamics like 1Password and folks like that who are like, you put money in, you still continue to get 12 to 14 month payback periods. You should keep investing in growth. And if you start to slow, like we have this odd thing now where like $100 to $200 million businesses aren't going public. And so what do you do if like you then start to meaningfully slow between that? You actually don't really have an acquirer set and then you can't go public yet. So as an investor, I would say, do you have competitors on your heels? And are you still growing? Um, I have portfolio companies and, and I have, I have friends who built in like a very nascent space and became like dominant market leader and like have continued to grow very profitably and still I think could be a public company. Um, but there's not that many of them. Most spaces have multiple players. I have a couple portfolio companies in these like weird like spaces where, but most of the time if you find a space that works, someone will come after your heels and very quickly either they'll take market share from you. And, and so you got to continue to invest in product and growth.

Yeah. Have you thought about raising capital, especially as I think Platters started to like build a name in the ecosystem and potentially competitors starting to build in the same space?

I think— I mean, this episode, by the time it'll air, this conversation will probably be different, but We raised less than $1 million in our pre-seed, which for us was really like, okay, we have a couple of proof points here. Like we bootstrapped to profitability before we took in any money, but still wanted like a little bit more conviction before— like I had multiple people that were like, oh, you should do like a proper round and we'll lead it. And I was like, that's really nice of you. But I have a lot of founders, founder friends who take the money and then think about like, okay, now what? Right? Where you, you get to like too high of evaluation or you raise too much money before you actually had any conviction on like what the end of the story looks like, which I think is a really big piece to this, which I've learned from a couple of my friends who've sold their businesses, which is like you have to know what the potential end of it looks like to reverse engineer how you think about approaching it, right? Which has resulted in us being extremely intentional about every decision that we make. We are about to do an extension, uh, actually next week, but by the time this is live, it'll be over, hopefully. Um, and it's still gonna be like a very small amount of money on a relative basis, right? Like after this all-in, we'll have raised less than like $2.5 million, um, at which point we'll probably be 30 people and profitable by, by February, uh, and so we know, we know what we need to do over the next couple months. And I don't think if you injected like $10 million into the business today it would change like the short-term goals that need to happen. And so for us it's been about like doubling down on solutions, not like raising money to try to go solve a problem. And because of that we've been a lot more patient with not making these decisions too early where we're like, all right, well, we can't go backwards now. Like, we raised way too much. We don't actually know what the full outcome looks like. And so I think that's a long-winded way of saying we've just like humbled ourselves in this process. It's like, it doesn't matter if someone tells you that you're great and that they want to give you a lot of money, because at the end of the day, you know your business better than anyone. And don't get like mesmerized by an opportunity that could potentially come back and bite you in the ass until you know what the end of the story looks like.

Yeah, that's totally fair.

Different businesses need different quantums of capital at different points in time.

I think the last point you made is the most important one, is like the different points in time.

Yeah.

It's not to say that like in a year from now I'm like, all right, I'm calling Taylor, we need money because like we don't know what to do. But like today, if you put $5 million in front of me, it wouldn't change the way that I'm going to operate over the next 6 months compared to if I just had like $1 million in front of me. Because we've made like pretty crazy strides from when we first started this business. I mean, you've been following it intimately, and sure, we've gone a little faster with a little bit more money, absolutely. But I don't think it's like the right thing for our business based on where we're at today.

Yeah, I've seen it go each— every direction. I've had companies that have needed a lot of capital at the front because they were like complex builds and hard, um, and then never burned again. I've had companies that were like marketplace businesses that take a little while to get off the ground, but like never really burn capital. But as you get to scale of a marketplace, typically like you need, like you need to be building adjacencies, you need to be building financial products. Like then all of a sudden capital becomes a real weapon and instrument. And I think at every stage it's just a different, a different equation. And as a, as a founder, you know, Like the funny thing is like investors try to quantify like product market fit and, and capital needs. Like founders tend to like, like if you look into yourself, like they really know they can tell a story. Good founders can, can, can say it with conviction. But like you tend to know, like, do I really need this? Do I just not want to make that hard decision? Do I not want to make those cuts? Or what do I need to keep this business going?

My only— the only issue that I have, and I mean, you, you're in and around the same like ecosystem, so you've seen a lot of these businesses. I think there's too many founders who aren't willing to do the hard thing. Like there's capital available to them and so they take it even if you really take a deep dive under the hood and like, I don't know if you actually need this today, but it's there, so you take it versus like building more leverage for yourself by just being willing to eat shit for a little bit longer to be in a place of leverage versus desperation. And there's a lot of founders that we both know who've raised a lot of money who are struggling to grow into the valuation. And then you get into this game of like down rounds versus layoffs and like all these things. And I would say a big piece of it as well is I'm a first-time founder. Like, I think my— I think a big fear that I had when we started this company, and my co-founders felt the same, was that I didn't want to go down this path of like the hype train, having never navigated these waters before, and then like kicking myself 5 years from now because I made some really stupid decisions all because it was there for me. So I think that's forced us to, to be willing to just endure a little bit more, to allow us to like learn more about how this works before we make any decisions. Back to what I said before, like I've learned more in the last 2 and a half years. Like, I wish I knew that when I started, but I'm glad that I didn't make any like out-of-pocket decisions until I got to this point. I'm like, all right, like I actually understand how this works now.

Like, that's actually why I was terrified to go down the founder path. The like honest truth was I had seen enough people fail in and around me that I was like, I went immediately went to that. Now some people can really block that out. I was like, well, what if I do this? And it doesn't work and it isn't perfect and it isn't the perfect story. Well, today I think I'm like sure enough in myself and who I am and like happy in life that I'm like, yeah, if it failed, it'd be fine. I know that there's a lot of ways to be successful and make money and, and, and do cool things and it doesn't have to be it. But like, I don't think I would have known how to deal with that then. And I really thought about that. I was like, okay, if this happens and this happens and, and, and it was right around a lot of like female founder takedown stories and a lot— I was like, I was like, no. I was like, I don't— I think there are people who have the resilience, and I think I have that resilience today that I don't think I had then.

I also think there's different types of failures, right? Were you the one that failed because you just sold a sack of shit and raised so much money as like a first-time founder, and now all these people are like, dude, what? Like, I'm not trusting you again. Like, this was completely reckless. Or were you someone that like was more calculated, but maybe the business just didn't hit like the growth that it needed to and it like evolved into a lifestyle business and it wasn't like a zero, but it wasn't the return maybe some people were looking for, or was it something in between? Um, I think as someone who sees relationships as like decades, I very much was not going to jump into an ocean of like selling people on something that I didn't wholeheartedly believe in myself until I actually believed it. Because I don't want to like burn bridges before my career actually starts because like I think when I call you at the age of 40, odds are people who are involved in my business now will probably be involved in some capacity, some way, somehow, like down the line with whatever, whatever else happens.

We're all going to be working for Taylor and whatever.

I'm going to be an analyst at Taylor's fund.

No, I totally agree. I think the human piece is like, these are my, like, my friends. They're people I care about. I deeply care about all the founders I work with and need to, like, have some sort of like interpersonal trust. You might not be best friends with everyone you work, but like, you, you want— you, you can choose who you work with.

Yeah, which is beautiful. I have a question for you about your experience with founders raising. What would you say, or like, what are moments that stand out to you of founders where you're like, wow, they ran an amazing process, versus somewhere you're like, what the hell was that? And my— the reason I'm asking that is because I have a couple friends who've recently raised from really legit people who refused to make a deck. They did under no circumstances. Like, I listened to him on a call, the investors like, oh, this is great, like, send me a deck. He's like, you're not a good fit. And so I'm like, wow, that's crazy.

Um, what stage?

Probably earlier, I think. I would say pre-Series A or Series A at most. Okay, probably before you have enough like data to be sitting there like modeling all sorts of outcomes and Yeah.

So I, I had friends go raise 2 weeks ago and I—

On the company side or fund side?

On the company side.

Okay.

And I introduced them to 10 VCs within that week. They had multiple term sheets and had many more introductions. So like that 10, that 10 teed off the other, which I think will show that like if you have foot in the door, it helps. Not to discount what they are building in any respect, because I think that there is both the extreme knowledge of their domain where if you pressure test them on, on anything in their domain, people are like, I trust these guys. You're like, wow, those are smart dudes who like know something that I don't know about. I bet you every— I bet you probably 1 out of the 20 VCs they talked to actually knew about the space they were building in. It was quite a complex space. It was very nuanced. It was cool and interesting in AI and people with domain expertise to go build there. But kicking off a concise process in which they had 10 VC meetings introduced by a VC to start their round or by a founder, even better to start their round, made the process really fast because then you have like all of the same people either getting interested or not at the same time, make introductions and then like runs a very concise process. So I think that, so I think both having this extraordinary, and they did not have a deck. They did have a memo that laid out the complexities of their space and understanding of the market of their space because very oftentimes like people are trying to reverse engineer TAM and they're like, okay, I love the founder. I love the space seems cool and interesting. I have no idea the size of the market. So understand, like, giving them contextual information about the market, actually in detail, I actually thought really worked in their favor. And then, um, and then, uh, and, and then more on them and why they were the right people to solve their problems. And then they had an MVP that was working, and you could watch a video and engage with it. So I don't think a deck— like, decks are great typically at pre-seed and seed, it's required. I think after that, like, you're seeing most of these rounds getting preempted anyway if they're best-in-class businesses. So like, most of the things that you're getting up to speed on other business are founder and outside-in work where you're understanding the market or customer calls. So I'm not a deck person. Some people are big deck people. I'm not one of them. I'm very oral in the way that I ingest information. So talking to customers is the thing that really gets me over the line at the most. Like a founder could say anything, but I'm like, if your customers are raving about you, like that's the thing I care about.

Is there something personality-wise you can call it like a reality distortion field or something else that causes capital to just like materialize around some people? Like, yes, on the infrastructure side, like Scott at Taido or Richard at Farmat, like capital just materializes around them. Again, there's like underpinnings or on the consumer side, Kevin from Immi or Seth at MasaChips who came on it. Again, there's like product underpinnings there. But there's something about personality too, that it just appears and seems very simple.

Um, 100%. There are people and it is very often around like one, people who understand venture capital, they understand how to navigate venture capital, they understand how to navigate firms. And how to drive competition in firms. And they also have like an instinctual, like, just confidence in themselves. Like, just true. Like, I— you don't see— there's like— I have founders in my portfolio who are extraordinarily good and are a little bit paranoid, and VCs can see through that. And sometimes when they raise, they actually have like the Sequoias of this world will actually just say no to that. They're like, that's not— like, we want to back founders that are like, just shoot for the moon, and we're okay with the zeros. Now, founders need to make choices when they choose capital partners, but that's what they're looking for, is like, we want the unicorns, not the middlers. And so, and they have pattern matched that more often, even if they see implosions, they're okay with it. I think the people that you mentioned are charismatic and charming and have command of their space and are very intelligent. Like, there's like consistencies to these people. They're really smart. They're very social and well-networked. They understand venture capital as an asset class. They understand how to drive competition and they know how to keep people apprised, but just enough and not too much. And like, very oftentimes those people build great businesses and sometimes they don't. And so whether they have to— whether they raise ahead of their traction or in their traction, I gave Rishabh a term sheet. I think he's like— I've— so I— and I think his business is great.

Do you think it's— do you think it's pure? I think a big part of it is the understanding of venture as an asset class. Because a lot of those folks that we named are also like active angel investors.

Yep.

Been around the block, maybe haven't raised capital before, but I think that understanding from the other side of the table matters a ton because I also— there's a bunch of founders we work with at Verbatim who I'm like, compared to some of those, have like much stronger business fundamentals and are just as smart, maybe as charismatic, but they don't understand the other side, whether they haven't personally invested or they just haven't. Maybe they're not a former investor. I'm like, why are you struggling to raise? And It seems to be like a lack of understanding of just as an asset class, like what they're looking for.

Dude, it's the art of storytelling. It's—

you're telling—

you're like, I really— you're, you're telling a story, you're creating FOMO. Like, it's— I think there's certain people, like ones that you named, where you can give them a fake business, it's not real, and they would figure out a way to convince someone to give them money.

It catches up to you at some point.

Yeah, no, I'm not 100%— I'm not saying it's, uh, ethical or the right thing to do. But just in terms of like someone who's good at fundraising, it's just like a personality in a way to like read a room and just navigate a conversation where I think they'll be able to do it regardless of the business, you know, God willing, the reputation catches up and it's a whole nother conversation. But I don't necessarily think that the best businesses are the ones that have the easiest time raising because it's all about the person who's driving the conversations and how you actually navigate that. It's not an investor to be like, all right, you might not be the most charismatic person to sell the story, but like when I look deep under the hood, your business is fucking awesome. The unfortunate part is that 99% of investors don't operate that way.

It depends on— okay, this goes back to stage and this also goes back to like understanding the right person for the right business. I'm an investor in a company called Navoda, which is a B2B marketplace in the diamond and jewelry industry. And I think Dave would himself say that like capital raising was not the thing he knew best when he started. I was the first institutional investor in the fund. They had come out of EF's accelerator and raised from friends and family and angel investors prior to us doing their Series A. But I think there's a point in which when we did the round, you could have said the— there was still risk on like the business fundamentals still had some risk to it. At some point the business just overcomes that. Like you just see the numbers and you see performance and you see markets evolve. I think what is, what really good founders do is they understand markets really well. It doesn't even matter what the product is at the start. It's, I understand markets and their adjacencies and this is why it's big. And so in the case of Novota, it's just like, it, you have to sort of, there's a lot of complexity in understanding that market and the things that move around it. The nice thing is there isn't a lot of software in and around it. So it may, it's very different than playing in a market with a million competitors and saying, well, like we're gonna build here and then go and build the next thing. Like we're, we were early investors in a company called Housecall Pro. And if you look at how the business has evolved, it's, it's, it's wild. But I don't think we're in the same world today of building tools for plumbers and HVAC professionals that it was 10 years ago when the Housecall Pro started. And the ability to build adjacencies is just not as easy. So I think that founders that are able to raise capital and the people that we discuss understand those markets and those adjacencies and they're like, this is how we're going to expand. This is why, this is why that TAM is really big. And that's the thing that found that like I think investors are drawn to because they're like, even if they're wrong, they know how to navigate it.

Yeah, yeah.

To solve the problem. What would you say looking back, are there commonalities amongst the founders that you've backed? Whether it's from a personality perspective, skill set, etc.

Um, in like immense knowledge of their space. Um, opposite of hype founders. Um, and that's not to say I will not— I will not and have not tried to back some of them. I think that, um, I've been a little scared of the, like, cap— the people who are that good at attracting capital. I sometimes think it's like a little bit of a scary land to play in. So I, having come from the operating side, I tend to look for people that, that just have like that just are so knowledgeable in their space and are so obsessed with the craft of building. And have a little bit of paranoia of what could go wrong. That looks different than I think a lot of, a lot of peers in the space where they just want someone that's, that's not thinking about all the— that's just going as big as possible. But in, in two of my portfolio companies, they, they had built in those spaces before in real subject matter and like knowledge. In one of them, I'd say both in, both in Pression and Vers Medical, they just became obsessed where like you just felt like they knew enough and there was something that their customers were obsessed with. That's the last piece is customers were obsessed with all of the products. And even if, even where there are like holes on the business in any of these examples in which they've overcome them over time, that customer obsession was the thing that got me over the line.

I think that obsession plays out. Have you heard the cupcake analogy about customer obsession?

No.

Oh my God. Okay. So it's basically if you come in the door before this podcast and unprompted you say, Adrian, Ben, I just had the best cupcake of my life and you tell me you have to go and it's completely unprompted. We're talking about investing. That's like the top tier of customer obsession and referrals that you want. The next tier, if you come in and I'm like, hey, do you know any great cupcake cupcake spots, you're like, oh, this one's fantastic. So you have to prompt. And then again, you go down the ladder. The worst here is like I ask a specific ask and you're like, do not go there, right? That's like the different ladders. And seeing— I think working with Pression has been great. We had Mike on the podcast like a month or two ago or something. And what's really cool about that product is sometimes I'll randomly talk to a brand and they'll just bring it up. Like I remember Will before I think he joined the team, we were just hanging out. And he was like, I don't think he was even in the conversation. And he was like, these guys are just killers and I've heard such good things and it just spreads that way. So I don't know if you've seen the commonalities there and like teams you work with.

Yeah, Pressient was like a— and Mike and I talk about it all the time. It's like a notch before I typically like find and get excited about a company. I was on 10 customer calls about other companies and Pressient came up on them. I think half the calls. And I was like, I think I need to invest in this company. And I called Mike and was like, can you, can you introduce me to 5 more? And I said, if this continues and I was like very candid, I was like, here's what I think is going to go right. Here's what I think is going to go wrong. But I had also forepresent in motion, like I was a commerce operator. So the pain points I had, I was obsessed with data and data to operate. Brands and the two major beliefs I had have proven true thus far. Let's hope that all, I like, I will fingers crossed for all of them that, but like my belief was as someone who is running growth and someone who is building all of our multi-touch attributions is one, omnichannel measurement will change and we need something that will automate and like in a lot of ways will probably do a lot of the job of the growth marketer. I was trying to like kind of like automate myself away, which I had done. I was an accountant, I learned SQL, I tried to automate accounting away. And then I believed that creative should like sort of run your business as a brand. Like you need your product to be good and you need your creative to be good and creative should run your brand. And so those were probably more operator instincts than I think the other pieces, which is why I spend more time, like I definitely spend more time diligencing learning about industries when they're in like random spaces versus commerce.

Yeah. Using that same analogy, how have you thought about getting to that top tier at Platter?

In terms of which—

a cupcake analogy of getting to the point where like you're building a product people are so obsessed with that they'll just start talking about it.

I mean, I thought the one yesterday was pretty good.

Yeah, that was damn good.

That was unprompted. He completely took a left-hand turn. He was like, by the way, I literally asked it at all. No unrelated. I messaged my team. I was like, I think we just got the best review we've gotten since we started the company. We had a customer on the podcast yesterday who just interrupted whatever we were saying and just started raving about Platter for 3 minutes. I was like—

Not to hype you up either.

No, it was unrelated to me. I was like, I didn't do anything. This is my team that actually helped execute this.

I think also when those happen, you should isolate, are we doing anything different for this customer subset? That happened. We were at a row in Haven, did a retreat in the Hamptons a couple of months ago. And I got there the day after. Two founders came up to me who are now customers. So big shout out to Mike, or in the process of becoming customers. And both said, Mike was like raving about you yesterday about content and things you can do. Like, can you help us? And I was like, that's, that's happened once in a while, but it's usually a pointed question. Like, hey, like we need to do content. Who is a good fit? And then someone will say, oh, like, oh, Verbatim could be a good fit. But in recent months, I think he was one of the only ones that completely out of left field was just like talking about us without us there. And I sat down with my team and I was like, what are we doing differently here? Because there's got to be something. And part of it may just be like they're growing like crazy. And part of it is like, okay, either we're serving— servicing differently, communicating differently. Maybe they're using our product in like a different way. And we're sitting down with their team like, how are you using the stuff that we're giving you versus other teams?

I think our— my barometer has 3 pieces to it. The first one is how many customer referrals are we getting? I think that's a really good way to see like, do people actually like what you're doing? Because if they're referring their friends to your product, then that's probably a good sign. Um, that's something that I monitor very closely. I would say the second one is if you have instances when things don't go well, like, why? And then the third one is continuing to try it, to your point, try to isolate of the people who like rave about you, who will tell the whole world to you, what are the commonalities of those personas? And is there a difference between them and then like other customers who maybe like what you offer, but they're not the ones that are like screaming from the mountaintop? And I think that I've started to see a lot of commonalities of just like the ICP of the person who uses it, who's like, oh my God, I can't live without this. And so then it's like, how do we just over-index on getting more of that type of person? Yeah. But the other piece I'll say is that I believe, given just like the size of the market, if you have like a subset of people who are absolutely obsessed with it, like I can't live without it, live without it, that means there's more of them out there, right? Like this goes back to this conversation of product-market fit, like If you have over 100 customers, do you have product market fit? Not necessarily. I mean, I think the barometer is different depending on the ACVs and whatever, but I think in the earliest stages, like if you have triple digit customers, you have a pretty large subset that love what you're doing. Odds are, given there's millions of brands, there's probably more out there that if they heard about you, they would feel similarly. Or at least that's the conviction you want as a founder to understand like why you should start to double down on things.

Yeah, I think as a data person, like this goes to usage and like, I think like you can pretty quickly if you get, if you had like perfect dataset of like, give me every customer, every user, like let me understand and like I could group that, I would like pretty quickly understand your business. And that's what people like founders find that request odd and some people don't have the infrastructure even set up there, but like, I was telling a portfolio company, I was like, I am going to highly guess that your customers that have more than 3 users that have different titles never leave. If it only succeeds in one user group, then you might see churn.

Yeah.

And I— that's mostly just from working in data long enough, but like, and being close enough to some of these portfolio companies. But, um, you typically like, is it, uh, Air talks about this, um, uh, that when you become like infrastructure to the entire organization, like no one rips out Air. Like it's, it's like it's impossible.

Um, that's why I love where we're at on the layer in terms of, dude, it's, it's like really, yeah, we're the infrastructure layer of the storefront. So our churn that we've had was like downmarket brands when we first started and we were just saying yes to people.

Yeah, it's like Shopify.

Yeah, I'm like, all right, I'm losing you because you're going out of business, like, understood. But we haven't had like an 8-figure brand that was like a year in, was like, you know what, like, we're actually going to migrate away from this.

Um, uh, you can find a lot of success in like the feature in getting to market, but once you become like sticky, probably multi-user, probably across the organization, like, you're probably not losing them. Like, and that's so you can— and, um, or it's always on. So like Segment, Fiverr, like, there's— there are some businesses where you can where you might— people might not actually give the cupcake review. Yeah, but like the usage is nuts.

Yeah, because it's maybe just not something they're thinking about. I think, I think it depends where in the stack you are in terms of how top of mind your product is, right? Because there's a lot of tools that are maybe like background, like background type tools where you're not literally sitting there touching it every day, but it's like powering a lot of things all the time.

Yeah. If people used Stitch before Fivetran, then you would hear them rave. And then people that just started on Fivetran were like, I could just do it and the data would come in and I wouldn't have to deal with it. And then, and so like, there is, that's the one time where I like, my company is like infrastructure investors can look at this differently, but like most companies I have people that are raving and you do see the difference in usage of whether it's a feature or whether it's a platform for them. And not every customer has the same usage of any of my, like one sample set is not enough. But you're like, okay, why I'm investing in you is I think you you can become that infrastructure layer across that organization.

I love the framing of multi-user, and I need to like sit down with my team to run through this because I think we've, I think we finally figured it out, but like real time over the past, I think about 6 months ago, we started to do some like more deep user interviews because something kept happening where our pitch is like, hey, at a big Series B, you should go build a content team in-house. We can silo out and just do case studies and stuff, but like, I want to take you from seed to B, whether that's a year, 2 years, whatever it is. And then you should bring it in-house. And we kept hitting this point basically for the first like 2 years of the company where we'd work with someone for like 10 to 12 months at the seed. The CEO would be using us directly as their content arm. Then they'd hire the head of marketing and we'd churn. And I was like, they still need the thing because they're going to hire someone else or they're going to try to figure it out themselves. And I like, I know they're not doing it themselves, but there's something about our current offering that it's like not working for them. And then it just kept happening over and over and over. And I was like, what is happening here? And we finally got two folks where they hired the head of marketing. We did a very specific like research with that new ICP. What do you want from us? How do you want us communicating? Because it's very different than how the CEO is using us. Like Mike uses us very differently than Vadim or someone else on the team. So we slowly started to figure it out, but there's still so much room to be done because even now at a B and C, we've seen some head of contents now using us. It's like, okay, that is a very different ICP. They want to siloed on a specific thing. They want different communication patterns. And so we still got a lot of work to do, but that's like a real-time thing that we were working through. Super painful.

I realize that we're over time here. It was rapid, which is usually a good indication of a, of a good conversation. So I appreciate you for coming on. I'm going to leave you with one more question. Looking back on your journey, what would you say was the biggest turning pro moment you've had thus far?

Like in my venture career or just in general?

Maybe venture specifically, like when you went from like a kind of entry-level VC to when you were kind of just like, all right, I'm playing a different game now. Like, I get it. This thing happened and now the world just looks different to me.

God, that— okay, so there's two on the operating side. I'll just use like, um, Annika Jong on my operating side. Like, for sure, like, she's was an amazing operator and mentor. And people who like in venture who meet me and they're like, oh, you know Annika Jong, you must not suck. I'm like, I'm definitely not as cool as her, but like was an amazing mentor and guide. COVID was the second, which was like, I think, like put me into like making the right decision for myself. And then on the venture side was learning what real conviction was and being willing to fight for that. And And like, because when you're junior venture, you're like, my job is to find deals. My job is to show deals with good metrics. Getting to like the next step is getting to conviction. And then the last step is winning. And I think that learning what conviction really meant was that turning point for me. And like, can remember the company where that turned. And now like, I will never go fight for a deal in which I am not at conviction.

Hell of an answer. Can you talk to the camera on your left? Tell them where they can find you and Headline.

You can find me at Taylor@headline.com. I'm in New York and SF most of the time, so hit me up anytime.

Oh yeah. Thanks for coming on. Thanks for coming on. For having me.

It's a wrap.

Well done.