In short
Tony Conrad’s view of the psychology and mechanics behind “great founders,” including valuation discipline, founder selection, and why early-stage timing matters in consumer, AI, and culture.
Guest backgrounds
Tony Conrad is an early consumer investor and operator. He spent a decade at Danone (including New York, Paris, and running M&A for Southeast Asia), then left to pursue Silicon Valley startups. He built Sphere and About.me. At True Ventures, he invests early in consumer brands (e.g., Blue Bottle, Sweetgreen, Modern Animal) and focuses on consumer behavior, AI, and culture.
Key claims
Markets can be frothy (especially in AI), but misvaluation will correct. Investors should be “the very first institutional capital” (pre-pre-seed) to shape a company’s DNA. Founder mistakes are unacceptable; market misses are survivable. Fast rounds/high valuations compound pressure and misaligned expectations. Founders should move with strategy, not panic.
Notable examples
Blue Bottle (invested after a “perfect storm” thesis: Starbucks alternative + strong brand point of view). Modern Animal acquisition announced the morning of the episode. About.me: sold to AOL when it was “too young,” later bought back and exited again; used to illustrate redefining “winning” beyond money.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOTony's Journey to Tech Startups
0:45 to 2:02
Tony shares his transition from Danone to the tech startup ecosystem.
“So I always took that responsibility incredibly seriously.”
The Allure of Tech Over CPG
2:02 to 4:08
Tony discusses his preference for tech due to faster iteration cycles and direct consumer relationships.
“And they're one of the most, of course, one of the most powerful consumer machines on earth.”
The Early Days of Investing
4:08 to 8:04
Tony reflects on his early investing days and the changes in the ecosystem over time.
“Because tech has got faster iteration cycles.”
Navigating the Tech Bubble
8:04 to 12:42
Discussion on the late 90s tech crash and its implications for today's AI landscape.
“Yeah, you know, when I was thinking about leaving Group Nano, there was a couple of things kind of at play.”
The Future of AI Valuations
12:42 to 14:01
Tony provides insights on the current AI market and potential valuations corrections.
“I mean, I do, you know, crash is a strong word here.”
Market Corrections and Founder Challenges
14:01 to 14:48
Learn about the anticipated market corrections and their implications for founders.
“But I suspect that we'll have a lot of things in the beginning that are misvalued.”
The Path to True Ventures
14:49 to 16:00
Discover the story of how Tony Conrad joined True Ventures and the circumstances surrounding it.
“I'm so glad I ended up partnering with John and Phil and Pani and Tony and so many of our team members here.”
Innovating at OddPost
16:01 to 17:41
Hear about the innovative journey of OddPost and its impact on web interactivity.
“What had happened, I got a little lucky.”
Simultaneous Ventures as a Competitive Edge
18:21 to 19:52
Explore the advantages of being both a venture capitalist and a founder.
“And I said, you know, I wanted to do this company and I didn't think I could do both.”
The Demands of Dual Roles
19:53 to 21:30
Understand the challenges and time demands faced by those balancing multiple roles.
“It's when your company works and your venture firm is working.”
Show all 29 chapters
Four Walls and Retail Concepts
21:31 to 23:04
Learn about the unique perspectives on retail as a distribution node for brands.
“So I know that You came originally from CPG.”
Investing in Blue Bottle: A Case Study
23:05 to 26:42
Dive into the investment journey of Blue Bottle and its market positioning.
“What were some of the early signals that you felt had the ingredients where it could actually become a business that makes sense for venture?”
Investment Decisions at True Ventures
26:43 to 28:00
Discover how investment decisions are made at True Ventures and the collaborative process involved.
“And, you know, we never looked back and it became certainly one of the more notable.”
The Importance of Founder Decision-Making
28:00 to 31:26
Learn about the decision-making culture in venture capital and the importance of founder independence.
“I think you have a lot of independence to make the final decision.”
Angel Investments vs. Fund Investments
32:21 to 36:30
Understand the differences between personal angel investments and fund-level decisions in venture capital.
“But I think on the personal basis, for me, it's about taste driven.”
Identifying the Right Founder
36:31 to 42:01
Explore key traits that indicate whether a founder is suitable for backing.
“How do you know if you have the wrong founder?”
Valuation Insights from Personal Experience
42:01 to 43:00
Learn about the importance of being cautious with company valuations and structuring early rounds wisely.
“Like I go back to my own companies, you know, Sphere and About.me.”
The Importance of Partner Selection
43:00 to 44:26
Discover how choosing the right investment partners influences company culture and success.
“the way you structure your company in this era.”
Navigating Founder Dynamics
44:26 to 45:50
Understand the factors that might lead to a founder being ousted from a company and the importance of collaboration.
“at this stage, it just, your world is going to suck.”
The Role of Founders in Companies
47:40 to 49:18
Explore the significance of founders' involvement in their companies and the complexities behind leadership changes.
“There's all kinds of different ways that can happen.”
Lessons from About.me
49:18 to 55:28
Learn about the journey and challenges faced with About.me, including thoughts on success and identity in the digital age.
“30 years and yes there's a handful of people out there that probably if they were listening to this go like, well, wait, that wasn't my case.”
Consumer Trends and Investor Sentiment
55:28 to 56:00
Discuss the ever-evolving landscape of consumer versus B2B investment opportunities.
“And people who are curious like, oh, who's Tony Conrad?”
Consumer Trends and AI Opportunities
56:00 to 1:02:38
The discussion dives into the fluctuating appeal of consumer investment and the rise of AI in business.
“I just think your identity is so much broader than any one of these social kind of vertical channels that we're in.”
Navigating Overlapping Investments
1:03:31 to 1:05:23
Insights on managing overlapping investments and the challenges of VC relationships.
“that you're being upfront with it, by the way.”
Lessons from Leadership and Books
1:05:23 to 1:10:02
Exploration of impactful books on leadership and personal growth, particularly Shackleton's journey.
“I think more money you have, the sloppier you're going to be on valuations and rigor.”
The Leadership and Management of Founders
1:10:02 to 1:10:40
Explore the unique leadership skills and management styles of successful founders.
“just an amazing story as you know for sure i hearing about how he's done i mean just what I find amazing was just how he man manages people.”
Book Recommendations for Understanding Disruption
1:10:42 to 1:11:29
Discover key books that provide insights into disruption and historical contexts.
“Wait, so I probably will reread this book.”
Reflections on Economic History and its Lessons
1:11:30 to 1:13:22
Learn how historical economic events relate to current market dynamics and job loss concerns.
“And so, you know, it allowed a whole generation of retail investors to kind of come in that weren't accredited investors.”
Personal Reading Experiences and Recommendations
1:13:29 to 1:14:11
Discuss personal reading habits and favorites that have made an impact.
“but i'm optimistic that it'll it will work itself out yeah that's fair i yeah i yeah that was such a great such a great book i actually got it for for christmas and I couldn't put, I just couldn't put it down.”
Transcript
Automatic transcript. May contain errors.0:00Be careful, you might get what you ask for. You just got to be really careful about the way you structure your company in this era. Fast high valuations, fast rounds, you know, inflated this, that, blah, blah, blah. It only compounds the pressure. Tony Conrad left the known to chase the speed, experimentation and innovation of Silicon Valley startups. After building companies like Sphere and About.me, he became one of the most influential early stage consumer investors behind brands like Blue Bottle, Sweetgreen and Modern Animal at True Ventures. Today, Tony is investing at the intersection of consumer behavior, AI, and culture, backing founders, building the next generation of iconic companies.
0:37We have a miss on a market because a market, that's okay. I can live with that. But when we have a miss on a founder, that really upsets me. As your companies get to bigger and better scale, they demand more of your time. So I always took that responsibility incredibly seriously. I was working a lot more than most people, literally 15 hour days every day. I was dead.
1:02Tony, thank you so much for joining me today. How are you? Mike, you know, I am good. I'm a little, as I was telling you earlier, I'm a little tired. We, we announced our, one of our companies, Modern Animal got acquired. And the announcement went out at 6am this morning, East Coast time.
1:25so i've been uh i've been up uh doing stuff but uh but that's so exciting congratulations on the outcome you know i think this might be the first time i've ever done a podcast or you know anything public facing on the heels of good news so normally i'm coming normally i'm coming from some challenging news uh so it's great to be here thank you well i'm glad that you're i'm glad I bet you're tired for good news. Yes. Instead of it being for bad news. So that's very good. I wanted to first talk about the beginning of your career. You spent a decade inside Danone. And they're one of the most, of course, one of the most powerful consumer machines on earth.
2:08You walked away and you went into tech and tech startups. What happened? um well i think you know so first of all like in that time period working for you know a cpg kind of brand focused company that was a very coveted role it still is a coveted role i think for for a certain type of person but you know when i was coming out of college that was that was just something everybody was kind of gunning for because it was great general management p &l management training, you know, brand distribution, all that stuff. And I absolutely loved working at Danon. I never envisioned I would be working there for 10 years.
2:52In some ways, I kept kind of getting, they didn't dupe me, but I kept duping myself into it. And, you know, started off in New York, and then they dangled moving to Paris. And I went there for four years. And then from there, I ended up running mergers and acquisitions for Southeast Asia for the company. And so, you know, I just kept kind of teasing it out a little bit and I kept getting more and more out of it. And so I really, really loved it. But I think it's different when you're working on something that's already at scale versus trying to work on something that is at inception of idea. and that really attracted me right to kind of kind of really better understand what I was capable of and there's no there's no better way to kind of figure that out than to be a solopreneur for a minute and and then you know to get into doing things that are at the ground floor so I really wanted to move from zero you know excuse me I really wanted to move closer to zero from, you know, scale.
4:00And that was really it. Why on the tech side? Why not on like the CBG side? Because tech has got faster iteration cycles. And I think it was just, you know, the direct relationship that you could have with, you know, consumers in tech is very different than kind of an arm's length relationship that you have with them. So, you know, like if you're, you know, if you're a brand manager of a yogurt company, you certainly are talking to consumers and trying to understand them. But you're not really interacting with them in a direct way, right? And you're reliant on a lot of third-party data, your partners, you know, to kind of get a feel for it.
4:46And tech is just like immediate, like you see, like this thing works or it doesn't work, or, you know, I can run a few experiments and try to try to get it going. And if that doesn't work, then you can just move on. And so I really love the data driven aspects of tech. And once I got a little bit of that taste, I couldn't imagine going back. It's like, it's like texting versus snail mail, you know what I mean? And, and, and both are effective. Right. And I don't, you know, I don't mean that like in a disrespectful way, but it's just like, they're both very effective ways of getting to, you know, a means to an end.
5:22But the immediacy of tech was just really, really exhilarating to me. And I never stopped once I got a taste for it. Talk to me a little bit about that era. What was it like when it came to angel investing and also starting and also just being around the ecosystem? How did you get involved? Well, you know, I've been doing this now for 25 years, almost actually getting closer to 30 years. I don't want to age myself, but, you know, it's been a while. And I think, you know, when you get, you know, having access to founders, you know, in the beginning was part of the game. But then you kind of would wait around in the early days for a little bit of signal.
6:11Right. And kind of try to see where the idea was going. And as time has moved forward here, you know, you're able to move. You don't have to wait for that. It's almost too late. The way that our funds are set up is that we want to be the very first institutional capital that goes into a company. And so we're looking pre-seed, whatever is pre-pre-pre-pre-seed these days. We're just trying to get involved with the right caliber of founder that is working on an interesting idea that we kind of ask ourselves, what if, you know, if they were able to succeed, you know, what does that unlock in terms of value?
6:52And so I don't think that the game hasn't really changed over time. I think that's the basic premise of what we do. It's just the time cycles have become so much more compressed. And so it pushes you even harder to get, you know, to develop your networks and the kind of the flywheel in your network. So you're getting absolutely the earliest access to high caliber, interesting founders as possible. Right. And, you know, if your other funds have different strategy, they want to wait until there's there's something that is working and they want to make a bet that their involvement can help hyperscale it.
7:35But I'm more interested in being, and I think we as a fund are more interested in being involved in the earliest part of that cycle because we feel like we can help impact the DNA of that company in a way that's much more significant than we can at a later stage. So anyways, I don't know if it's changed all that much. It's just those time cycles are just so much faster than they were before. So back when you were starting angel investing and also kind of before you started your company, um, you just left the known. And whereas it seems like in, in the San Francisco Bay area, what was the approach to kind of get involved in the community, um, and actually meet founders and even, and how did you even think about when you were first starting on investing, what were the right founders that you actually wanted to partner with and back?
8:26Yeah, you know, when I was thinking about leaving Group Nano, there was a couple of things kind of at play. One is I really wanted to get back home, right? And San Francisco, I grew up in Indiana, so this is not where I'm from. But figuratively speaking, I wanted to be back in the United States. And also in 1993 or 1994, 1995, I was using the Netscape browser out in Asia. and I was like watching Chicago Cup, not watching, I was like watching on a screen Chicago Cubs baseball and it would be like ball one.
9:07You know what I mean? I've been there. I've been there. But to me it was like, oh my God, this is going to be amazing. And so everybody kind of knew that the Bay Area was happening and where the movement was. And so I decided, A, I wanted to get back to the U.S. It was really clear to me I wanted to live in the Bay Area because I wanted to be around this ecosystem. And thirdly, I also needed to take a year off. Like I just, you know, I had my children, my two boys, while I lived in Asia. And I'd always fancied, I'm one of those odd people that at the age of five or six, I'd kind of always fancied being a father.
9:47And here I had these kids and, and I was just constantly on an airplane. You know, the job I had in Asia was a, it was a big geography to kind of cover. And so I just was never home and I really needed, I was burnt out and I needed a year off. And so I told my wife, I'm going to take a year off. And she says, good luck with that. And, and, and she, she was working and she's an architect. And so we moved here and I did take that one year exactly to the day. But in that time frame, I started, you know, just meeting with people, getting to know people. I didn't really know anyone in the Bay Area.
10:23And so I was just constantly networking and just, you know, what people were up to. And eventually I started writing a couple of little checks. And so, you know, it was a great time to be an investor in 1997, that's for sure. And you didn't have to be very skilled and you'd probably have a good outcome. So anyways, that's how I got into it. And then, you know, the crash happened. And I think that's such an amazing moment in the history of Silicon Valley because it kind of showed a glimpse to the future, you know, the speed of the future. and valuing companies in a different way, valuing what could happen.
11:07And, you know, how could it unlock additional TAM and all that kind of stuff? But it also, it was, well, yeah. I mean, I just think it was just a perfect moment to kind of like pause and see a lot of the people, I don't know how to phrase this, is why I'm struggling a little bit, but like a lot of the posers, I guess is what I'll say. You know, a lot of people thought it was kind of quick, easy money. And those people had kind of gotten involved in tech and they weren't really in it, I think for the right set of reasons, which is about creating, you know, it's about making something from nothing.
11:50It just, I mean, yes, it comes with great rewards, but that can't be the primary driver. And I just think the community had become overly populated with that type of, you know, kind of professional. And so a lot of those folks kind of went back to their corporate jobs and comfort, you know, places that were a little bit more comfortable for them. But a handful of us kind of stayed back here because we could see the data doesn't lie. And it was like a, you know, every time you looked up the stadium was getting fuller and fuller and fuller of people. And while there weren't business models it's clear that there was traction and that it was working and there was something really interesting here so i knew at that moment like this is what i'm doing this is this is this is how i'm going to ride out the rest of my career i'm going to be working around this stuff because i knew it would work and it eventually did work so do you think looking at that era that late 90s early 2000 era when there was a big tech crash and there obviously was a bubble and then a crash since you i know that you've been through you know you know quite a few cycles um how do you think about this ai era do you think that right now there's a bubble when it comes to ai and there's going to be a crash or or or going to be like a um a uh a change in terms of valuations that's quite substantial?
13:22Yeah, I think all of that. I mean, I do, you know, crash is a strong word here. Is the market frothy, I guess. Maybe that's a better way to say it. Sure. And I think, you know, markets correct themselves when things get misvalued and overly valued, right? And so I think what's tricky about AI in this kind of era of new company is the TAMs on some of these companies, you know, I mean, these foundational models are just extraordinary. And how it plays out in the application layer is to be seen. But I suspect that we'll have a lot of things in the beginning that are misvalued. And we can get back, we can get into that a little bit later, you know, when we talk about, you know, some of the risks and pitfalls for founders in this era.
14:21But I, yeah, I just think, I do think there's a correction that will have to happen in order for, in order for the models to work for everybody, right? For the founders, for the entrepreneurs, the team members, for us as investors, RLPs, I do think there has to be a correction at some point in time. So I think that's coming. Yeah, that's fair. It's very, very fair. So how did you end up at True?
14:56I'm so glad I ended up partnering with John and Phil and Pani and Tony and so many of our team members here. Um, you know, it was Phil Black and I, um, were sharing an office. This is back in that moment when like the market had crashed, it was 2003. And he said, just come work out of my office. And I was like, okay, I'll come do that free office. It's great. Had a pool table. It was fun. Um, and he asked me if I wanted to join him in the fund. He was raising a different fund at that point in time called blacksmith capital and i said you know no i want to actually see if i can start a company um i feel like this is the moment right and so that was when i found it why why sorry why did you feel like that was the moment when you said that so many people were kind of going back to their corporate jobs i understand if you went back to your corporate job you'd be travel around asia or role but was that was that ever on the table for you no that was never on the table that's never been on the table since that moment.
15:59Like never one second have I actually dreamt or thought about that. What had happened, I got a little lucky. In 2003, I invested in a company called OddPost and founded by Ethan Diamond and Ian Lamb. And the CEO of it was my partner now here at True, Tony Schneider, who subsequently became the CEO of Automatic WordPress and was also my co-founder in another chapter in a company called Sphere, which we're going to get to here in a second. So OddPost, though, was amazing because they were really innovating on the edge of DHTML, which is Ajax. And it's what makes the web interactive and asynchronous.
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17:23And here's the best part. David Drexler, the founder, is offering his service free forever to anyone in the ConsumerBC community who mentions the show. So if you're thinking about hiring an agency, talk to the hidden gems first. It's free service, biggest bang for your buck you simply can't lose. Link in the show notes. Seeing these guys develop this company with$1 million total, they were living in a library. They were using things like a shared server, which became cloud, obviously. Costs were really low. And they had a massive success. And I thought, wow, the cost to do these things has gone so far down that I think I can, with a half million dollars, I think I can get something up and running and see if I have a good idea here.
18:15So that was really how that transition happened. At the exact same time, though, Phil and John Callahan were getting together and founding True Ventures. And they asked me if I wanted to join. And I said, you know, I wanted to do this company and I didn't think I could do both. And they said, well, we get to write our own rules. We're starting our own funds. So why don't you join and you can do both? And I was like, how is that going to work? And they go, we'll figure it out. So one of the first things that they did, which was amazing, was they moved our partner meetings to Tuesday because for both Tony and I, it felt disingenuous for us to go work on our companies and show up on Monday morning, be the first thing that we did.
18:58Right. And so it just it just kind of felt our way around it. And I think what we realized really quickly, Mike, was what an unfair advantage it was to be both a venture capitalist and a founder simultaneously. I guess Reid Hoffman had done that. Andreessen had done that and a handful of others. But it wasn't that wasn't a thing that most people did. and it was it was just like in the boardroom we were learning so much about growth you know hacks and things that were working that we could apply to our company and you know when we were just being you know entrepreneurs we were mixing with other entrepreneurs and so deal flow was great and it made it really really easy to kind of do both and so we did both until until eventually we couldn't do both.
19:50Eventually you can't. Eventually that breaks. When was that moment? When was that moment for you? It's when your company works and your venture firm is working. I think honestly, that is when it breaks. And you're like, oh my God, I'm going to blow my brains out. Like, how am I, uh, how am I going to do both? You know, like I just, you know, I was just, I was dead, you know? And by the way, I did, I signed up for this, you know, duality gig, you know, for over a decade, um, because I went on to do another company as well. So twice. Yeah, no, exactly. Well, talk a little bit about when you actually at the moment said, I can no longer do, do true and kind of had to focus on, you know, not that you weren't full time, but all of your energy onto the company.
20:36Um, I don't think I ever got to that where like, I felt like I can't do this. It just, it was just tiring, you know? And, um, as your companies get to bigger and better scale, you know, they demand more of your time and, and the stake, the table stakes are much higher and you owe it to those founders. And so I always took that responsibility incredibly seriously. Um, it just meant that I felt like maybe I was working a lot more than most people. Probably not true, but like, you know, at least in my head, I was just like, my God, I mean, I'm working, you know, literally 15 hour days every day and I got my family and I'm going home and I've got to make sure I'm going to be there for dinner and bedtime.
21:20And then I'm going to pop back up on my screen, you know, in the basement, you know, my gluing machine in a dark basement, you know, the optics were pretty bad, you know, for sure. So I know that You came originally from CPG. You started tech investing and investing in tech. You started two tech companies as well. What fascinated you about four wall and retail concepts? I think that most people just see four walls, but I just see it as a distribution node for a brand. and you know if it works it's not about the unit or you know for me it's more about what it unlocks there's brand there's product expansion there's cultural relevance and then i think if you can get to scale one thing people don't really understand about four wall is it it's incredibly highly defensible right the the the cost for somebody to get into that game or so much cap Yeah, it's a lot of capital.
22:26And that's kind of the knock on it. And that's why it's, you know, it falls out of favor in a moment like this, where AI is so super scale and all that, that, you know, it's kind of hard to justify working on four wall stuff, you know, in this moment. But that'll change. That'll change. Because those same things I just said about defensibility and your ability to create very large scale businesses, you know, is real. And that's not going to go away. It's not like physical part of our world is going to disappear, at least in my lifetime. Maybe in yours. You're younger than me, but not in mine. Well, okay.
23:03So one of the first four-wall concepts, I believe one of the first one, one of the first four-wall businesses that you invested in was Blue Bottle. I thought it was one of the first ones. What attracted you about Blue Bottle? What were some of the early signals that you felt had the ingredients where it could actually become a business that makes sense for venture? Yeah, it's a perfect storm. I wasn't looking for it. It was always a coffee kind of aficionado. And it was a space that I thought was interesting. I knew Blue Bottle. They'd had their one cafe here. a buddy of mine Brian Meehan who had founded a couple of other companies and very successful guy he came over for dinner one night and he you know asked him what he was working on he said you know I'm working on you know don't tell anyone but there's this cafe called Blue Bottle do you know and I was like yeah of course I know it in fact I even know the founder like he serves in the farmer's market and I always talk to him and extraction techniques and all this stuff like whatever we were kind of geeking out about.
24:14He goes, well, I think, you know, he's open to actually a venture kind of type investment. And I go, how much do you think it would be? He goes, I think we're going to need$10 million. I go, I'll do half. And I literally shook his head. He'll tell you the same story. I literally, I just leaned forward, I go, I'll do half. And he goes, like, for real? And I go, guaranteed. So then I came back and we had a policy here. true that you have to you kind of have to disclose anytime you're investing over a certain amount and you know in anything just to make sure and I think one of my partners asked me like why why I thought it was interesting that I would do that and I was like well oh my god I just laid out this thesis around you know there's Starbucks there's obviously going to be an alternative to that this is a very different kind of approach and can they take five to ten percent of the market cap of Starbucks.
25:11Absolutely. Like, you know, and for me, it was like the question I kept asking myself was no matter any place in the world where there was a Starbucks, if you were to open a blue bottle or a kind of a artisanal based coffee shop across the street, how would it do? And the answer was it would do incredibly well. Would it kill Starbucks? No. But would it like, would it do incredibly well? Absolutely. And for me, that was so that was the market sizing. I just kind of understood intuitively. And then the brand and what James, you know, Freeman, the founder kind of stood for was to me, the same things you always look for in any tech investment, high conviction, a real like point of view around how you, you know, the entire, like, from the moment you walk in, what's the door handle to getting to the point of sale, you know, using a square machine, having limited menu, having espresso drinks only consumed in porcelain kind of cups.
26:18Now they now do them in paper cups, but in porcelain cups at the time on premise because it should be consumed at a certain temperature. All this kind of stuff, this level of detail, just so like amazing to me. And it's the same thing that you find in the best founders, period, like of any probably industry, but certainly in tech. And I was just like, you know what, this is a no brainer. The combination of Brian and him, this is like, let's go do this. And, you know, we never looked back and it became certainly one of the more notable. It's not by an order of magnitude, not the largest outcome we've ever had.
26:56But it's just a very notable brand moment for us as a firm. And still today, you know, people, people think of me as blue bottle Tony. And I'm like, well, I've done these other things. I know you've done a lot of other things, by the way, modern animal just sold to this morning, right? There was a sweet green that we did. And then we have another one, you know, Madison Reed, which is massive in the, in the hair space and uh you know in amy eric who is a phenomenal founder phenomenal founder and one of our bench partners here at true as well so you know it can work for sure what how does how does true invest meaning when you decide that you want to that you found a company that that you want to invest in on, on true, how does it actually work?
27:51Do you need other partner buy-in or are you how much, um, how much independence do you actually have in terms of, in terms of making the bet? I think you have a lot of independence to make the final decision. You do not have carte blanche independence to, to run the traps on. Is this a good idea? you know what are the pros and cons of doing it all by yourself in a little silo and then go make that decision that that doesn't work for us i think what we want to do is free us up to have healthy discussion right and to depersonalize it so we can just talk about the merits of a deal or a space or a founder in a way that's much more authentic.
28:43But ultimately, you know, each one of us has experienced enough and has hopefully kind of earned the right to be able to make the call. Right. You know, it's like it's like it's like being the head coach at the end, like on each deal, you're kind of like the head coach. You know, you assemble a bunch of players, you go off, you diligence it, you do all the work, you know, you figure out whatever you're you're open to listening to different kind of plays, but ultimately you got to make the call. And, and, and so that's what the kind of culture that we've tried to create here and not second guessing each other.
29:14Right. And I've had, I've had deals where people are just like, oh, please don't do that. And you know, by, by the way, I should have probably listened on most of those cases, but a couple of times I've had deals and I won't tell you which was, but where I was just like, you know what, I'm going to make the call. i'm gonna make it i'm gonna do it it's worked out just fine you know do you think in some ways it's an advantage of being in multi-categories beyond just software businesses yeah massive that's massive um i mean it'd be this would be great there's there's thesis investors out there which i'm not one of them that we could sit here with and we have a great debate on that right how you know your understanding of a space compounds really quickly the more that you're in it and I do believe in that like I do believe I could go pull a trigger on another coffee investment and and I don't want to and I'm not going to because I don't want to I don't want to diminish what we accomplished with Blue Bottle but like I do I think I could go be successful again in that space Absolutely.
30:24Because like, I understand it. But I do think that there's for a fund. I love that we have a bunch of contrarian bets and lots of different categories, everything from biology to I mean, we have massive, massive unicorn companies. And, you know, at the intersection of biology and AI stuff that I don't even I have no clue about. Right. Thankfully, we have partners that do. Rohit and Adam and Paneet. Paneet does all kinds of stuff in security. He did Duo Security and they did Veza. Veza just had a$1.6 billion exit. But, you know, it's just like there is a real value in that, but not for if all of us were just security folks, you know, or biology folks.
31:19I think we'd be missing out on a broader set of opportunities that are quite interesting and can be real fun makers for us. This episode is brought to you by the Hidden Gems. Let's be honest. There's a lot of bullshit in the marketing agency world. So much under delivering, overcharging and incompetence. You truly don't know who's good until you engage. And by then, it's too late. That's what The Hidden Gems solves for. Powered by deep agency insider knowledge, they provide founders and brand operators with only brand beloved, highly vetted boutique agencies at preferred rates. Agencies across media, creative, dev, design, events, social, and beyond, all well covered.
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31:56The Hidden Gems serves brands like Dr. Squash, Monster Energy, Gorilla Mind, Figs, and Sattva to achieve some of their biggest growth. And here's the best part. David Drexler, the founder, is offering his service free forever to anyone in the Consumer V.C. community who mentions the show. So if you're thinking about hiring an agency, talk to the hidden gems first. It's free service, biggest bang for your buck. You simply can't lose. Link in the show notes. How do you think about, because I know you also have an extraordinary angel investment portfolio. How do you think about what makes sense from an angel investment perspective, like flower and water and trick dog versus, you know, fund investments like blue bottle, sweet, green um what's actually different and do you know when you talk to a founder and if you're interested in the company which bucket something kind of goes into i do i do i do um and we try we try not to do a lot of personal investing right especially anything that can be around the edges and as we've done things like blue bottle and these you know it makes it harder and harder to find a kind of unique edge out there.
33:02So over time I've done less, less so. But I think on the personal basis, for me, it's about taste driven. They're often smaller, sometimes non-scalable ideas, but they're things and they're, they're people I want to back. They're people that I can turn a very modest amount of capital into a three X, you know, or maybe a four X, five X in a reasonable timeframe. And, you know, it's great. And it's, it's fantastic. On the fund level, there needs to be a path. You got to really believe on every investment you make that if things went right, you got a few lucky breaks and you got the right team, you know, the, the right founders as, you know, protagonists that you could return the entire fund.
33:46Like in each one of our funds we're now on our eighth fund we've always had a company you know well let's just go through the first four funds which are the mature funds we've always had a company that does that that returns the entire fund right um and and so that's you just have to you have to have a real understanding nuanced understanding of the different buckets there i know it all depends about check size and that sort of thing. But when you under it, I know if thing goes right, as you say, it has to return the whole fund. Does that mean like a 10X return, for example, based on the portfolio or maybe based on the actual company specifically or is that upwards?
34:31I think it's upwards. I think it's 25X and above. 25X. So you're underwriting. If everything goes right and you have a couple of lucky breaks, that you can get a 25x on that return on that investment. We have investments where we've made 75x. Yeah. Yeah. That's amazing. That's extraordinary. It's extraordinary, right? But you've got to really push for that. You've got to make sure. And by the way, when we've got it wrong, which is most of the time, and that's the nature of this, most of the time you're kind of – I mean, we even have lower batting average than probably, you know, the the like low end of a baseball, you know, professional baseball player.
35:17You know what I mean? But when you get it right, it's just so crazy good. And when it doesn't go right, you know, there's two things that well, one thing one thing is inexcusable to me to get wrong, which is the founder that we back. And, you know, that is the thing where we need to over-index and make sure that we're getting the right founder. Now, obviously, we don't get 100%. We have misses there, too. But when that happens, when we have a miss on a founder, that bothers me. Like, that really upsets me. When we have a miss on a market because the market didn't develop or kind of become something that we didn't, you know, it didn't become what we envisioned that it might be able to become.
36:03that's okay. Like, that's okay. That's just, you know, you just, you just, there's a why in the road and you just ended up on the wrong side of it. And that's okay. And execution, that's okay too. Like if you know, if you mis-execute, you know, it's a bummer, especially when that market is real and you just mis-executed, that is a bummer, but I can live with that, but I can't live with it when we get the founder wrong. It's just that, that to me is like, that's basic one-on-one stuff that we got to get right. How do you know if you have the wrong founder? Well, the first, well, how do you know if you have the right founder?
36:42Let's talk about that. All right. Now I'm like my mother. Let's keep it positive. I'm an optimist, right? You know, You know, I like it when a founder is not rushed, is does not think of this as a game, is incredibly thoughtful, as thoughtful as we are about working with them as they are about working with us. Like I like a founder that asks questions. And it's always a telltale for me at the end of a pitch if they actually ask any questions. If they don't ask, you can't tell you how many times people don't ask questions. And I may have even liked the idea up until that point in time and the founder, but then they didn't ask any questions and it gnaws on me.
37:31And I've learned that that's a pattern recognition moment. Like you got to ask questions. like otherwise they're not going to ask the right questions to their partners to prospective employees you know teammates you know all kinds of stuff right they're just they're just not they're just going to be so in their own head they're not going to be curious about what makes you tick and so I like that I like a founder that understands storytelling I mean, and not like a fictional story, but like help, help me understand your narrative. Like, I'm really interested in like the humanity of all of this.
38:09Like, who's the human behind, you know, the, the, the name. And, you know, sometimes I'll walk into and you'll have a founder that's maybe less experienced or nervous or whatever. And, and they'll have their presentation up, you know, on the screen by the time you walk and they're ready to just kind of jump into it. And I'm just like, let's just spend 10 minutes, 15 minutes. Let's just talk. Not doubt about the Chicago Cubs, you know, but let's talk about like, you know, like who are you? Like tell me a little bit about you so I can understand, you know, the journey that you've been on, how you ended up sitting across the table from me.
38:48And I also like to share that back, you know, in a much more cryptic way, but, you know, I like to share that back So I don't want to waste their time. This is their show, not my show. But I do want to share a little bit about that. So that's it. That's how I know if we've got the right founders or not. How in this age where it seems like some categories like AI, for example, are moving super quick and founders are raising so much money and things are just going really quick and maybe they kind of have to be rushed in a lot of senses. what's what's your view on that when it comes to talking with founders if they have to move really quickly you have to work you have to move in a calculated way so you do have to have a certain cadence to the way that you you know process and you kind of the the decisions that you make and the boobs that you make.
39:46My partner, John Callahan's pilot, and John, by the way, is one of the top venture capitalists in the world. You know, we don't talk about it because we don't publish our data, but I know the data and John is exceptional. And he always says, no quick hands is one of the first things he teaches you as a pilot. And so when you're up there and something goes wrong in your aircraft, you, you, you gotta like, you gotta like process very quickly, but at the same time, you just can't help just panic. Yeah, panic, right? And so you really, you really need to do that. You need you need people that are going to move with a strategy in place and tactics, but in a very calculated way.
40:29And I think that what we see is that, you know, like certain things like fast high valuations, you know, fast rounds, you know, inflated, you know, this, that, blah, blah, blah. You know, it only compounds the pressure later, right? And it shows up, it's harder to fall on rounds. There's less room to grow into the story. It's misaligned expectations. It's just all this stuff. And I've been seeing this now for 30 years. And it's hard in a moment like this, in particular, where like, yeah, you got an idea, let me value it at$50 million. But like, be careful, you might get what you ask for. Like, and founders, if you're that one founder, and every founder thinks they're that one, right?
41:15Unicorn, we're like, damn it, I should not have given away 20 % of my business early on for 5 million bucks, right? You know, or even worse. it's like you know seriously just slow down and like structure your business in a way that is smart and creates an opportunity for you to to to be able to capitalize that company with the right people at the right valuations um that makes sense right that create an opportunity for you to have exits later or to eventually become a you know a sustainable you know public you know standing company. Like all that stuff is really important to get right. And in this moment, I think most people are getting that wrong.
42:03I really do. And that's not being self-serving. Like I go back to my own companies, you know, Sphere and About.me. Like I was an accomplished person already in the community. I could have named valuations much higher on Sphere than I did. I could have certainly when I did about.me, I could have named kind of whatever I wanted in terms of valuation, because it's a success of sphere and the stuff that we were doing with WordPress and automatic and Matt and Tony. Right. Like, but I didn't like, I valued my company at$5 million. I took, you know, I took 20 % dilution for a million dollars. Like I didn't need to do that.
42:40I could have taken 5 % dilution, you know, but I'm glad I did because it presented itself. It presented, there was an early opportunity to have a great exit that was accretive to all of us and meaningful to my co-founders and team members. And we were in a position where we could go do that, right? And feel great about it. And so we, you know, you just got to be really careful about the way you structure your company in this era. No, totally. I mean, I've, I've heard you on past shows say that founders should resist overheating their early valuations. And, you know, I know that you obviously as you mentioned pat um you priced your own last last company very modestly um and when he could have gone higher talk to me about like what seed is currently at and because it seems like it's pretty in inflated and if that's the case how do you compete um it is inflated for sure and the there's lots of things where we just we're going to be disciplined and we're not gonna to, we're not going to succumb to the pressure, but luckily because of our reputation and our, you know, our performance, you know, in the marketplace, we have an amazing flywheel of founders that we've worked with in the past who either go on to create new companies and they want to come back and work with us, or they're sending us, you know, team members that spun out of their successful company, right?
44:09And so those type of founders, I think are the ones that we're working with. I think they're a little savvier in a lot of ways. And they're over-indexing on getting the right partner at this stage because it changes everything. If you get the wrong partner at this stage, it just, your world is going to suck. I can't say it any better. I've just been on too many boards where I've seen the wrong type of investment partner come. And I always say, thankfully, we're there because we can help protect the cultural DNA of the company. We can make sure that we buy. I mean, we have so many crazy stories, Mike.
44:52Companies that have gone public where the growth investors want to throw the founder CEO who got us to that spot, you know, overboard, like six months, nine months before they went public, like just crazy, crazy stories where we've had to say, like, we're not voting for that. No way. They've earned the right to take this thing public. You're like, we're going to go all the way. Like, so there's just a lot of behavior out there that, that I think people Or they want their people in. I want my people in to run this. And I think that you just have to be careful about as a founder and make sure that you're getting the right partners around the table.
45:35So I think we're able to get our deals still. We've never had a median ownership under 20 % in any of our funds. Well, at what point does it make sense to oust the founder? What do they have to do? If there's anything fraudulent where we've had, you know, we've had that. We've had founders that are not collaborative and are hiding. They're not transparent. They're not open about what's not working and what, you know, what is working is easy, but what is not working. You know, just like in life, there's certain people that know how to manage up, but they don't know how to manage laterally or down.
46:21and so they're really good managing their board but then we'll start to hear horror stories about how they're interacting with their executive leadership team or the culture is toxic those kinds of things those are areas where i think it's like it's not so much like outsting but but it's evolving you know moving away from a founder you know like this episode is brought Brought to you by The Hidden Gems. Let's be honest. There's a lot of bullshit in the marketing agency world. So much under-delivering, overcharging, and incompetence. You truly don't know who's good until you engage. And by then, it's too late.
46:59That's what The Hidden Gems solves for. Powered by deep agency insider knowledge, they provide founders and brand operators with only brand-beloved, highly-vetted boutique agencies at preferred rates. Agencies across media, creative, dev, design, events, social, and beyond, all well-covered. The Hidden Gems serves brands like Dr. Squash, Monster Energy, Gorilla Mind, Figs, and Sattva to achieve some of their biggest growth. And here's the best part. David Drexler, the founder, is offering his service free forever to anyone in the Consumer BC community who mentions the show. So if you're thinking about hiring an agency, talk to The Hidden Gems first.
47:35It's free service, biggest bang for your buck you simply can't lose. Link in the show notes. I mean, I'm still of the school of belief that there's never a scenario in which a company benefits by not having its original founder or founders involved in the company. That may be an advisory role. It might be in a board role. It might be an operating role. There's all kinds of different ways that can happen. That doesn't mean that they're CEO. And that's OK. Like I like I'll I will line up on that if I think it's the right decision for the company. Um, but rarely, rarely does that come to that. Most of the time, I think that the founders that we've worked, that we're working with and why I say selecting the right people that you want to work with and then getting them, convincing them to want to work with you is that they're going to have a lot of self-awareness, you know, the type of founder that we like working with.
48:32and they're going to know even before I do most of the time that it's time for them to to maybe step aside and I would say in over 80 percent of the cases when somebody has stepped away from being or when somebody we have made a change in things I've been involved with where we've made a change at the CEO level they've been driving that or co-driving that with us right as opposed to us kind of like hey this is not going to be a good day we're going to sit down and have a bad tough conversation with you right i just that just almost rarely it never that almost never really happens you know but it but to be clear it has happened i've been doing this for 30 years and yes there's a handful of people out there that probably if they were listening to this go like, well, wait, that wasn't my case.
49:26But that's not the norm here. How do you think, though, balancing that with your fiduciary responsibility with LPs and obviously investors to obviously get the highest return on your investment? I think if all you're trying to do is get the highest return on your investment through hardcore execution,
49:58that's going to present problems later. Without naming any of these companies, I'm sure there's like five that just flashed in front of your mind where we know these kind of CEOs that just drove, drove, drove, drove, drove, and then everybody kind of knew. Everybody swept it under the rug because they're executing really, really well. and there's a massive price to pay down the road. And so I think that's not a healthy company. That's not a good company. And so you either pay the price now or you pay the price later in those situations. That's fair. That's fair. I want to talk a little bit about DotMe.
50:44You've described About DotMe as a capital efficient win. You've had two exits, a loyal user base, even if it didn't quite become the identity layer of the web that it was supposed to. What did that outcome teach you about how founders should define winning for themselves?
51:06I'm proud of the work that we did at About.me. And as you noted, we did have a very successful outcome, bought it back, then had another successful outcome. Which is so rare. I mean, it is rare. And we're lucky that that happened. Or maybe we were skilled in making that happen, you know, hopefully a little bit. But I felt like it was a colossal failure for a bunch of different reasons. One is I shouldn't have sold it the first time, even though we had a great outcome, because it was way too young and it wasn't ready. And AOL bought it. AOL was fantastic. I have nothing but nice things to say about AOL, Tim Armstrong, their team there.
52:00They over-delivered everything from what we expected. But the reality was it wasn't even a year old. It wasn't ready for that. It needed more time to become. Why did they buy it? Why did they buy it? Well, because I think Tim, you know, Tim had built the revenue business at Google on the ad side. And then he became, you know, very high profile CEO, you know, for AOL. You know, AOL still had juice. It had a lot of assets and a lot of potential. and you know so so you know he came in and i think he looked around he's like okay i've got a bunch of legacy business here that are that are good but i gotta find my my you know my ipod um you know and i need to take some shots on goal and so i was you know they had also bought sphere and so i was leaving as he was coming in.
53:02And I think he said, Hey, you know, like, but you're the kind of person I need to have here. And I'm like, but Tim, I'm a, I want to go, I want to go start another business. And I've stayed longer than, you know, my lockup, like, you know, I was above board here. He's like, well, how about you be an advisor to me into the AOL? And I'm like, okay, sure. And so we just stayed close. And then just kind of over the course of that year, kind of working on this idea, Yeah, he just loved it. He totally rocked it and loved it. And I really liked him and respected him. And so he made us offer. And it's one of those moments where for me that that offer, it was meaningful because it was like second time success.
53:44So like from that, but the financial rewards of it, I didn't need those. You know, and I don't mean that in a disrespectful way, but I just did not need those. I had enough money already at that point. But I had co-founders and I had team members and other people that this was going to be their first exit and it was meaningful to them. And so I just felt like, you know, let's do it. And so I kind of talked myself into it a little bit. Yeah.
54:12I still think the premise, like somebody out there, I wish if I had more energy, I'd go do it again.
54:22Because I think the way that we learn about each other, we're just kind of outsourcing our identity to Google. And who knows, you know, AI, I guess, you know, here in the future. But we're just really outsourcing it. And I don't know, like, you know, if anybody's listening to this, I don't Google myself every day. So, in fact, I don't think I ever Google myself. I have no idea why it might come up. But you really want you want to control that narrative of how you see yourself. And by the way, I don't want to also I don't think of LinkedIn as my I love reading in that team there. But that's my professional identity.
55:05That's not who I am as a holistic person. And Facebook was kind of in that era was like, that's my social that's my social graph. and all that kind of stuff. And that also doesn't cover the professional side. So about.me was just like this little simple idea that you could put it in your email signature, put it in your Twitter bio, put it wherever you are on the web. And people who are curious like, oh, who's Tony Conrad? They click on that. There's a picture of me. And here's a little bit about me. And then here's all the links to the things where you can find me on the web. And that's it. And I just think that that idea is still relevant today.
55:44So somebody go out there and do it. And then we had the name about.me, which was amazing to have that name. So that's why. For sure. For sure. Thank you so much for explaining it. And also the premise and the thesis that you had that you still don't, you still think there's an opportunity there in terms of building something for it. Absolutely. Absolutely. Absolutely. Yeah. I just think your identity is so much broader than any one of these social kind of vertical channels that we're in. I know you're a generalist investor. I know we talked a lot about your consumer portfolio, which I really do appreciate you talking about it.
56:32Over the years, consumer has kind of constantly been out of favor, at least the past few years. what's your view and do you feel like you're spending more time looking at b2b versus consumer i am right this second um so consumer may go in and out of favor with investors but it never goes out of favor with consumers right like literally so you know pause on that and then you're like okay, consumer has this twisted relationship with tech where it kind of comes and it goes and it comes and it goes. Right now, though, we're clearly in a platform shift to AI. In fact, that shift has already happened now.
57:17It's not even happening. Where I think the infrastructure layer and the tool layer is the most interesting here in the beginning, but soon it will be the application layer, both on the enterprise side and on the consumer side. And what we do know is that if you look historically in any of these, you know, big waves, the infrastructure layer, excuse me, the application layer is about 10x the value of the infrastructure layer. So there's a lot of amazing outcomes that will happen, you know, around applications. But right now I think it's important for us to double down on some of the bigger kind of infrastructure type problems, you know, security being like, you know, foremost in our mind right now.
58:13And the entire stack, as we all know, like it's boring. Anybody's listening is like, yeah, I already know that dude. Like, like the entire stack is, is being rewritten. And, And so, I mean, there's just incredible opportunities out there. And so that's what we're a little bit focused on. Now, we have three investments, or I have three investments that, you know, on behalf of True, that I've kind of co-sponsored or sponsored, that I'm very excited about that start to, I think, they're kind of like prosumer. business and i know a lot of people hate that word and i kind of hate that word but it's the best way to describe it so there's a company called autos another one called pulsia both these companies oddly enough are chasing the same idea which is using ai as your co-founder right and you know you know it's kind of the idea is you you click once give a few prompts and you go to bed and you wake up in the morning, you've got a company.
59:16And then that company, all the ops around it, the infrastructure stuff, all the marketing, consumer acquisition, videos, ads, all that stuff is just being created by the agents. And these companies are growing incredibly fast. So Autos and Pulsia are the two that are both, they're coming at slightly different angles, but they're both attacking kind of the same, same area. We can talk a little bit about how that happens because we don't typically do bets in the same space. And then the other one is Nectar Social, which I know Mizba. Well, she's great. Mizba and Farah are, wow. You know, ex-meta, you know, they, they know their, they know all this social stuff incredibly well.
1:00:04And if you think about like websites being the, you know, the, the consumer engine, you know, the DMs are now, you know, where the consumer is, you know, interacting. Right. And interacting. And so Nectar Social is, I think, I mean, I think all three of these companies are going to be monster sized companies. And they all have great, you know, Henrik and Nicholas at Autos, Ben, who's a solopreneur at Pulsia, and, you know, Ms. Benvera. They're just all fantastic founders to work with. So anyways, I think we're starting to move closer to this maybe consumer application area. So why are you able to make two bets in the same space?
1:00:57Well, we invested in one of the companies. We'll go into the total history here, but this happens sometimes where, you know, you invest in a space, you invest in a company. It's really clear. Company A, you know, going after that idea that I just described. And you invest in something that's over here and really not at all there, but they're working on some different stuff. And they kind of pivot a little bit and pivot a little bit more and pivot a little bit more. And the next thing you know, like, oh, you wake up and you got two companies in the exact same space. And that's what happened in this particular case.
1:01:36And so, you know, it's a little tricky. But luckily, you know, all of those founders understand, you know, nothing was done intentionally. And now we've got these companies in our portfolio, and our job is to be as supportive to both of them as possible, right? And to have great guardrails around no sharing of information and all that kind of different stuff. So it's working out. I think it's always tricky. You've just got to be in open dialogue. And on our end, we have to not overreact. I think if I was in their seat, I'd be a little bit upset, right? I'd want to understand. But once I think I understood what happened or how that happened, then I'd be okay with it.
1:02:30It'd be like, okay, I got it. Let's move forward here. This is not what we should focus on. Focus on our own company and go for it. This episode is brought to you by The Hidden Gems. Let's be honest. There's a lot of bullshit in the marketing agency world. So much under-delivering, overcharging, and incompetence. You truly don't know who's good until you engage. And by then, it's too late. That's what the Hidden Gems solves for. Powered by deep agency insider knowledge, they provide founders and brand operators with only brand-beloved, highly-vetted boutique agencies at preferred rates. Agencies across media, creative, dev, design, events, social, and beyond, all well-covered.
1:03:06The Hidden Gems serves brands like Dr. Squash, Monster Energy, Gorilla Mind, Figs, and Sattva to achieve some of their biggest growth. And here's the best part. David Drexler, the founder, is offering his service free forever to anyone in the ConsiderBC community who mentions the show. So if you're thinking about hiring an agency, talk to the hidden gems first. It's free service, biggest bang for your buck. You simply can't lose. Link in the show notes. Yeah, well, I mean, it's great that you're being upfront with it, by the way. I mean, you're saying it here even publicly. So that's really impressive.
1:03:39I will say it because, you know, it sucks. It does suck. It sucks for me. It sucks on one level. But once again, any fund of our size, and we have$4 billion under management, you're just going to have things that end up overlapping. It's just the reality. I remember there's been lots of times where we did not invest in things because - Being so concerned that it would be overlapping. Well, we knew it was overlapping and yet there were big outcomes. Like, so, you know, when I was on the board of Automatic and WordPress, you know, we did not invoke Best and Tumblr and we could have, you know. Oh, that's interesting.
1:04:22There's things like that out there because it was so clear to us that that was whatever. It turns out that Tumblr and WordPress are kind of very different. Very different. Yeah. But in the time, it felt like they were the exact same thing, you know. And I know Andreessen had some stuff around Instagram and some other company. And they think they, yeah, I can't remember what happened, but I think they kind of had a falling out with the Instagram guys. And so they ended up having a stronger relationship with the other company. That other company went out of business in Instagram, we all know, had a fabulous success.
1:04:57So, you know, I think it's best if you can just avoid getting to a, you know, we're going to detonate the nuclear option here. You know, there's a reason we're all working well together. And, you know, these hiccups happen and, you know, it's part of life. And so you move on. Totally. What's your view on megafunds? Have they been really hard to compete with? Yeah. Yeah. I think more money you have, the sloppier you're going to be on valuations and rigor. And I also think like in some of these mega funds, you know, buyer beware. You know, you take what feels like maybe, you know, what feels to me like a very large round now, you know, 15, 20 million dollars.
1:05:50You're taking it from one of these mega funds. but it doesn't mean you're going to get the attention because it's such a small amount of their capital, right? And so as soon as your idea isn't working that hard, they're just going to focus on other things. And that's not the way we work. So, you know, we want to be here for all the iterations of it because once you finally get to the kind of promised land, that's what's rewarding you understand all of that it it's just it's messy it's murky all the m words it's all that and then when you get there you're like yeah like on a day like today with modern animal i mean you know that was that's not a straight line by any stretch of the imagination you know but it is a very successful straight line at the end yeah i mean i know you're also in slack with stewart you know just seeing how how he's been a couple times too and the monster that obviously it's amazing he did that twice where he pivoted and there's a good example like you know like you know he's working on both times he's working on gaming companies and one he ends up being a internal messaging system and the other ends up being a photo annotated photo app you know So these are really different ideas that evolved out of these other projects he was working on.
1:07:25And I'll bet you, you know, you might've had some overlap. His investors might've had some overlap with other companies. That happens. Totally. Totally. What's one book that's inspired you personally and one book that's inspired you professionally? Oh my goodness. I don't think we can go with one. I mean, it's a stupid personal. Love it. Love it. So, In Praise of Shadows is absolutely probably my favorite book of all time. It's a very easy 100-page-ish, kind of-ish read. Perfect for me. I have trouble reading, so it's just amazing. But it's about design. It's about, you know, kind of early 20th century Japan.
1:08:15hand and it's just incredible, incredible book. And Tony Fidel, you know, who invented the iPod and the iPhone and Nest and a few other things, he had recommended it to me years ago and I'm so thankful that he did. I've read that book. I'll bet you I've read that book 50 times. um and then uh shackleton's journey to me is the most mind-bending um story of leadership ever ever written you know yeah i don't know if you know that story yeah i'm actually currently reading it uh are you really okay like i'm like halfway through yeah i would just hear it's a little bit of spoiler alert but you can handle it um we all kind of know that they all yes yes yes every single person survives which is unbelievable Every single person, 100 % survived.
1:09:08The most gnarly expedition that you could ever imagine. But within, I can't remember, you'll get to the end of this book. I think it's within three years, over 50 % of them, once they're back in England and wherever they go to, they die. Over 50%. Alcoholism, drug abuse, scurvy, all kinds of different things, right? But it's just, it's like the human capacity to persevere with a set of really incremental goals, like really modest incremental goals, and just day by day to get through it, get through it a little bit, just get through it, just get closer, get closer, get closer. you know you know once they get there then they fall apart you know when they get home and that part is sad but the to me the the leadership that it took is crazy uh and it's just an amazing story as you know for sure i hearing about how he's done i mean just what I find amazing was just how he man manages people.
1:10:21Um, you know, in terms of he should have this person, for example, be by his side because he thinks that this person would disrupt the rest of the group because he's like kind of negative, you know, just, just all these managing all these different personalities on top of obviously getting people out to, to, uh, to survive the whole thing. It's, it's really incredible. I'm going to Antarctica in November and I cannot Wait, so I probably will reread this book. Oh, my gosh. Report back. Oh, my gosh. I'll send you some photos. But on the professional, the innovator's dilemma, I think, if you're in this business, is still the best lens on disruption, how disruption actually happens and why it happens.
1:11:02I think that's an amazing book. And then one that I'll just throw an extra one in here just for fun is Andrew Sorkin, who I have tremendous respect for, wrote a book called 1929. I just read that. Yeah, yeah. And I think that's just so fascinating to me. And I think the parallels with, I'm not saying that there's going to be a depression by, you know, so I want to put big asterisks on that. But I do think there are a lot of interesting parallels here, right, with what we're experiencing. And it's, you know, it's about at that point in time, the, you know, the residential investor, you know, could get very easy, you know, interest free, not interest free, but, you know, low interest, you know, loans and get leverage.
1:11:51Right. And so, you know, it allowed a whole generation of retail investors to kind of come in that weren't accredited investors. And so that's why we have a lot of the rules that we have today. But, but the most fascinating thing about that, Mike, was when you understand the things that kind of pulled us out of the depression, one of the key things was at the end of, I think the secretary of commerce or whatever, had this thesis that he wrote up that we should move from a six day work week to a five day work week. and you're like oh that doesn't make sense yeah but why that works is that he the thesis was that it would create a whole cottage industry but a large cottage industry around hospitality and travel and all that and it worked it literally worked because when you went to a five-day work week and then on friday night you could leave and still go to church on sunday but when you were working, you know, Saturday afternoon and you've got only Sunday off, you're going to church.
1:12:57Like there was no travel, there was no hotel industry. I mean, you know, to note. And so I'm kind of wondering, you know, every time I, the reason why I like that book, why I think it's instructive for us, I know there's a lot of panic about job loss. And by the way, I have that same job. I used to have that same panic. And I think that's real. And I think there is going to be like a bad moment for us. But I also believe in humanity's ability to problem solve and to kind of figure out unsuspecting ways to get through things shackle the journey and i think you know this idea around travel and so i don't know what will happen in the age of uh ai but i'm optimistic that it'll it will work itself out yeah that's fair i yeah i yeah that was such a great such a great book i actually got it for for christmas and I couldn't put, I just couldn't put it down.
1:13:51I just kept reading it. And I'm actually not, I actually don't really read a lot. My wife is, is really like the reader in the family. She reads like 160 books a year. I read, I read like, gosh, I don't even, I don't read that many books a year, but I just, I couldn't put it down. And then we'd also listen to like audio book and stuff like that in the car and just, just loved it. Loved it. It's amazing. I mean, I lugged that book, I got it at Christmas too. And I lugged that book to New Zealand. I mean, that's a, that thing is, you know, that's a, that's a hefty, hefty book to lug around, but I did, I finished it.
1:14:25You know, that's amazing. That's amazing. That's awesome. That's awesome. Uh, Tony, this has been so much fun. Thank you so much for your time. I really appreciate it. Likewise. I, uh, I, I know my answers are never that crisp, but hopefully, uh, the narrative So it helps everybody to kind of frame their own perspective from this. Great. Thank you so much.
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Most venture capitalists have never actually built companies.
Tony Conrad did both.
In this episode, Mike sits down with Tony Conrad, Partner at True Ventures and one of the earliest investors behind companies like Blue Bottle Coffee, Sweetgreen, Madison Reed, Modern Animal, WordPress and more. Before venture capital, Tony spent a decade at Danone before leaving corporate life to build startups during the earliest days of Silicon Valley’s internet boom.
Tony shares what it was really like living through the dot-com crash, why he believes AI is creating another major market correction and the lessons founders keep ignoring when it comes to fundraising, valuations, and building sustainable companies.
The conversation goes deep into founder psychology, venture incentives, why most investors get founders wrong and how Tony evaluates companies before there’s even product-market fit.
He also breaks down:
- Why he instantly invested in Blue Bottle
- The danger of overheated seed valuations
- Why most founders choose the wrong investors
- The real role of storytelling in fundraising
- What separates iconic founders from everyone else
- Why “fast money” creates long-term pressure
- How AI is reshaping both enterprise and consumer investing
- Why he still believes consumer is massively underrated
You’ll learn:
✅ Why Tony left Danone for Silicon Valley startups
✅ What the dot-com crash taught him about AI today
✅ The founder traits most investors overlook
✅ Why inflated valuations hurt founders later
✅ How True Ventures thinks about ownership and returns
✅ Why Blue Bottle was an obvious bet for him
✅ The difference between scalable venture bets vs angel investing
✅ Why founder-investor alignment matters more than valuation
✅ How to know if you have the right investors around the table
✅ Why consumer investing always comes back
👉 If you’re a founder, operator, or investor trying to understand how great companies are actually built across multiple cycles, this episode is packed with hard-earned lessons.
Timestamps
00:00 Intro
01:00 Leaving Danone for Silicon Valley
04:00 Why tech felt more exciting than CPG
05:30 The early days of startup investing
08:00 Moving to San Francisco during the internet boom
10:00 Lessons from the dot-com crash
13:00 Is AI in a bubble right now?
15:00 How Tony joined True Ventures
17:00 Building startups while investing simultaneously
20:00 The burnout of being both founder and VC
22:00 Why Tony loves four-wall retail businesses
23:00 The Blue Bottle investment story
27:00 How True Ventures makes investment decisions
29:00 Why being a generalist investor matters
32:00 Angel investing vs venture investing
34:00 What “venture-scale” really means
35:00 The one mistake Tony hates making
36:00 How to identify the right founders
39:00 Why founders shouldn’t rush fundraising
41:00 The danger of inflated valuations
45:00 What founders should look for in investors
47:00 When founders should step aside as CEO
50:00 Balancing founder support with LP responsibility
51:00 Lessons from building About.me
55:00 Why digital identity still matters
56:00 Why consumer investing is underrated
58:00 AI infrastructure vs AI applications
01:00:00 Consumer AI opportunities Tony is excited about
01:02:00 Investing in competing companies
01:05:00 The problem with mega funds
01:07:00 Lessons from Slack & Stewart Butterfield
01:08:00 Favorite books & leadership lessons
01:11:00 AI, job displacement & optimism for the future
01:14:00 Final thoughts
📬 Subscribe for more founder stories & scaling insights:
👉 https://www.theconsumervc.com/
Follow Mike Gelb:
Twitter / IG / TikTok → @mikegelb / @consumervc
