Most people think venture capital is about spotting rockets early. It’s not.
It’s about deciding which fires are worth sitting next to while everyone else complains they’re not warm enough yet.
That’s the quiet throughline of this conversation with Adam Besvinick, founder and managing partner of Looking Glass Capital. If you didn’t listen to the episode, here’s the short version, this is a masterclass in patience as a competitive advantage.
The cold email that started everything
Adam didn’t grow up inside the venture bubble. He cold-emailed his way in. Hundreds of messages. Twitter replies back when Twitter was still a small town instead of a shouting stadium.
One of those cold emails landed with Chris Sacca.
That turned into a remote apprenticeship at Lowercase, working nights and weekends while in business school, learning how early conviction actually forms. Not spreadsheets first, people first. Not speed, judgment.
The lesson stuck.
Cold outreach still works, Adam has backed multiple companies that way, but only when it signals clarity, effort, and respect for the other side’s time. Spray-and-pray is noise. Thoughtful curiosity cuts through.
Pre-seed is not finance, it’s psychology
At the earliest stages, there is no data. There is no certainty. There is barely a product half the time.
What there is, is a human being deciding whether they are willing to suffer longer than most people would.
Adam describes pre-seed investing as pseudo-psychology, evaluating resilience, self-awareness, and how founders behave when the plan breaks. Because it will break.
This is why he believes lived experience matters. Why a 25-year-old running a venture fund is often underprepared, not because they lack intelligence, but because they haven’t seen enough hard conversations yet. Cap table conflicts. Co-founder breakdowns. The slow grind of markets that take years, not weeks.
You can’t vibe-code your way through those moments.
The traction trap
One of Adam’s most honest admissions is that he used to overweight early traction. Many investors do.
Revenue early feels like gravity. It pulls attention. It quiets doubt.
But over time, he saw how often early traction was a false positive. A marketing spike. A novelty curve. A short-term behavior masquerading as product-market fit.
Now he treats traction as one signal, not the signal.
A company growing slowly in a market with long sales cycles, regulatory friction, or real-world complexity may be far more durable than something scaling fast on vibes alone.
Or as Adam put it in the episode, some startups are giving others “company dysmorphia,” unrealistic expectations shaped by outliers that distort what normal progress actually looks like.
Patience is not passive
This is the part many people miss.
Patience doesn’t mean hands-off. It means staying engaged when things are boring, uncomfortable, or unfashionable.
Adam backs founders in healthcare, climate, education, and economic infrastructure, spaces where nothing happens fast and everything matters. These founders don’t quit at the first down-round scare. They cut salaries. Extend runway. Keep shipping.
The unspoken contract is simple. Try as hard as you can. If it fails honestly, no one is angry.
That dynamic, Adam argues, is what makes venture work when it works.
Why Series A is broken for many companies
One of the sharper insights in the conversation is about the widening gap at Series A.
Many modern Series A funds need to write massive checks to justify ownership targets. But more startups today don’t need that much capital, especially with AI-driven efficiency.
The result is a mismatch. Companies that are healthy, growing, and capital-efficient struggle to raise because they don’t fit the check size math, not because the business is weak.
This is where early investors with conviction matter most, helping founders choose the right path instead of chasing the biggest round available.
AI flattens teams, not judgment
Yes, AI is changing everything. Teams are smaller. Output per employee is higher.
But Adam is clear about what it won’t replace. Taste. Context. Pattern recognition built through years of repetition. The ability to help a founder through a deeply human moment.
If anything, AI raises the bar for judgment. When execution becomes cheaper, decision quality matters more.
The quiet signal of fund three
A subtle but important takeaway for emerging managers, getting to fund three is itself information.
Not because it guarantees success, but because survival requires discipline. Doing what you said you would do. Not chasing shiny objects. Not rewriting your strategy every market cycle.
In Adam’s words, the bar for consistency in venture is shockingly low.
The bigger pattern
Zooming out, this episode isn’t really about venture capital.
It’s about incentives.
We live in a system that rewards speed signals over endurance, optics over substance, and short-term narratives over long arcs. Adam’s approach quietly rejects that.
He’s not trying to see everything. He’s trying to see clearly.
And in a market addicted to immediacy, that might be the most contrarian strategy left.
If you’re a founder, the takeaway is reassuring and demanding at the same time. You don’t need to look like an outlier in month six. You do need to be resilient enough to still be here in year six.
If you’re an investor, the question is simpler and harder.
Are you optimizing for excitement, or for truth?
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Chapters:
00:01 Welcome and Adam’s Background
03:00 Cold Emails and Breaking into Venture
07:30 Apprenticing with Chris Sacca at Lowercase
11:50 Early Operator Experience at Gumroad and Startups
14:50 MBA Decisions and Career Tradeoffs
19:30 Transition from Operator to VC
23:00 Venture as Psychology
28:30 Patience vs Speed in Venture Capital
33:00 The Myth of Fast Growth
36:00 AI and the Flattening of Teams
41:00 Why Series A Is Broken for Many Startups
46:00 Concentration vs Spray and Pray Investing
51:00 Founder Resilience and Hard Moments
56:30 Building Looking Glass Capital
01:01:30 The Future of Pre-Seed and Closing Thoughts
Transcript
Brian Bell (00:01:05):
Hey, everyone. Welcome back to the Ignite podcast. Today, we’re thrilled to have Adam Bespinik on the mic. He’s the founder and managing partner of Looking Glass Capital, a pre-seed firm known for being the first yes for mission-driven founders. He’s invested across the earliest stages of company building, worked with iconic seed firms and later stage funds, and has supported founders solving challenges across health, climate, and economic drivers. Thanks for coming on, Adam.
Adam Besvinick (00:01:27):
Thanks for having me, Brian.
Brian Bell (00:01:27):
So we were giggling before about this trauma question, but I’d love to know what your origin story is and what do you think the trauma that is driving you and shaping you?
Adam Besvinick (00:01:36):
I think maybe ultimate sort of first world problem is I don’t fortunately have too much trauma that’s driving me to build a venture fund. Origin story-wise, I’ve kind of been surrounded by small business entrepreneurs and founders since I was growing up. My grandmother ran a small business. My father ran a small consultancy. Now, these aren’t startups in the sense of the types of companies that you and I fund, but I’ve kind of been surrounded by entrepreneurs from the time that I was quite young. And so seeing that type of drive and the dedication that it takes to start a company was something that I saw firsthand from a relatively young age. And so I don’t necessarily think that’s the reason why I became a venture capitalist per se, but I do think it is a really important part of my upbringing in terms of wanting to be surrounded by these types of inspiring individuals who want to build something from scratch and sort of control their own destiny to a degree as far as sort of like origin story and adventure it doesn’t feel all that dissimilar from a lot of sort of peers who tried to network their way into this ecosystem when it’s sort of you know very relationship driven and relationship centric and you’re you know It’s an overused term, but you’re trying to like hustle your way into conversations and meetings and coffee chats. And I was fortunate enough years ago at this point, which feels dating myself that 14 years ago, I was still like, I was out of college, well out of college, but I sent cold emails to literally hundreds of VCs and was active on, you know, very active on Twitter when Twitter was a different place, trying to get in front of investors to figure out the best way to network my way into this business. industry. And unfortunately, a lot of people got coffee with me and got on phone calls with me and took the time to share their advice and experiences. And one of those people was Chris Saka, who started Lowercase Capital and has since gone on to start Lower Carbon and has probably the best seed track record of all time, the best seed fund of all time. And I ended up working remotely for Chris when I was in business school from 2011 to 2013. And that was a role that I got with Chris. And really, I started with Chris that came off of a cold cold email to him. And so that was sort of my foray into venture and was working 10 to 15 hours a week remotely for Chris for two years while I was in business school and just trying to soak up as much as I possibly could from the way that he worked with founders, the way he thought about making investments, the way that he thought reputation as a, you know, really was like one of the first truly solo GPs when he started the fund. Nobody called it that, you know, in 2010, 2011. And so that was, I’d say that’s my like venture origin story or more proximate origin story, which is sort of the way that I was able to sort of network my way into this, into this industry and sort of parlay that relationship with, with Chris and what I learned from him to eventually start my own firm.
Brian Bell (00:04:27):
Yeah. So you’re, you’re at a grad school and how did you come up with Chris’s name? Like, it’s just like, did you read a case study and you’re like, Oh, that’s what I want to be like, or you just kind of knew of him or,
Adam Besvinick (00:04:37):
um, well I was, I joined Twitter as a user in March of 2009, which, you know, now feels, you know, quite early for joining Twitter.
Brian Bell (00:04:47):
My first tweet is like around the same time and it’s like, why is nobody here?
Adam Besvinick (00:04:51):
I mean, the feed on Twitter in 2009 was literally every tweet in the world because there was so little content that they couldn’t just rely on you, on people you followed to populate your feed. And so, I ended up following a bunch of VCs and tech people that way. And I really sort of, I remember tweeting back and forth with people with VCs who, you know, I had 120 followers or something and investors were actively engaging on the platform and using it. And obviously in a very different way than Twitter gets used today by, by investors. And I ended up emailing Chris February of 2010. So I hadn’t even gone back. I knew I was going back to school or sorry, February, 2011. I knew I was going back to school that following fall summer. So I wasn’t even in school yet. And I was basically reaching out to investors to say, I’m going back to business school. I want to end up in venture two plus years from now. How should I optimize my two years of business school if I want to end up in your seat when I graduate? And everyone had a different answer. Most people said, don’t go to business school. They said, take that money and go start a company or basically do anything else. Some people had... basically everyone thought that their path was the right path and you know, you know, that there’s really no one path to getting into, into venture sort of stumbled upon Chris through following him on Twitter and seeing how he, you know, and he was obviously, you know, Twitter’s biggest fan outside of outside of, you know, Evan, biz and Jack. And so he just sort of like fell in love with how he talked about the products and how he used the platform. And I sent him a note and said, you know, basically the same thing that i was telling other people i want to get into this field after i graduate and he was kind enough to respond to a handful of questions i had and i then said like hey if you need if you ever need any help sort of someone help you part-time or as an associate or whatever like i’d love to i’m raising my hand right now and he ended up reaching back out to me um about a month and a half after i started school and said hey i have a portfolio company that could use some help you know you’re top of mind for me because you know We’ve been interacting on Twitter and email and whatnot. It’s a portfolio company needs some support. And if you wanna work on this project with me, I think you could be useful to them. And it turned out to be Twitter. And so I ended up working on this project with Chris and he said, we’ll just treat this as unpaid. I’m not gonna interview you. I’ve read your tweets. I’ve read like the blog posts you’ve wrote. And if you screw this up, then I should have done more diligence. And if it goes well, then we can talk about something more formal. I ended up working on this project with them for a few months. And it went well enough that he was like, I’m happy with the work you did. Twitter’s happy with the work you did. Here’s a lowercase email address. You can go to demo days on behalf of lowercase. I’m raising a new fund, but do some research that sort of underpins my investment thesis. Send me deals and companies that you think are interesting. I went to South by Southwest, representing lowercase. I went to Techstars demo days. I went to 500 Startups demo days. I got sort of unparalleled access. to, you know, at the time stuff that I’d never would have been able to go to as a regular business school student. But now all of a sudden I’m like, you know, unpaid associate intern for Chris. And so I, you know, got to interact with tons of people and meet tons of founders and stuff that I never would have had, you know, the ability to do, to do if I hadn’t gotten that opportunity.
Brian Bell (00:07:59):
So cold emailing works, it turns out.
Adam Besvinick (00:08:01):
I’ve gotten LPs through cold emailing. I send cold emails every day. I funded probably a dozen companies off of cold emailing.
Brian Bell (00:08:08):
No, I mean, and as VCs, we both get cold emails left and right, you know, probably 40 or 50 a day for me. I mean, now WhatsApp is becoming a thing where people are reaching out on WhatsApp and then you have Bordy, right? Yeah. You know, Andrew with the CEO on the pod and like 40s now like reaching out to me. It was like three or four people fundraising every day. It’s just a deluge, you know?
Adam Besvinick (00:08:27):
Yes. But I’ve funded probably 10 companies that have been cold inbound since I started Looking Glass. So it’s a very useful channel when it’s done well.
Brian Bell (00:08:36):
So what happened next? So you graduate and then you go on to Gumroad at some point.
Adam Besvinick (00:08:40):
Yeah. So Gumroad was a lowercase portfolio company and the summer between my first and second year of business school, I kind of sat down with Chris and I was like, what should I, he’s like, don’t work for me, you know, work for me this summer. Don’t do venture full time for the summer. Go, go to a company. And so he was like, you could go to Twitter, you could go to Uber, you could go to all these different, he’s like, he’s like, I have this, you know, sort of super early company. The founder is 19. I felt like he was like, I was 25. It’s not like I was like old, but that 19 felt like super young to a 25 year old. He’s like, you’re not gonna get any training. You’re not gonna get any oversight really, but you’re gonna learn a ton. and you’re going to work hard and you’re this is as close to being you know without founding the company yourself like you’re working from his apartment you’re just going to learn you know as much as you possibly can from um from style and so i said great he introduced me to style i remember meeting him at south by southwest um in austin in 20 it was a spring 2012 before you know that summer break in between my first and second year of school I was like, great, I’m going to go work at Gumroad for the summer. So I ended up, you know, working with him and Ryan Delk, who has since gone on to, Ryan was a summer intern at Gumroad the summer that I was there, who has since gone, he went to Omni and has since started Primer in the ed tech space. And I ended up just Brian and I were doing business development. We were trying to figure out how do we get major artists and major creators onto the platform and trying to drive, you know, sort of like notable users to monetize content on Gumroad that weren’t like long tail creators. So we spent time going to, you know, spending time with film companies and, you know, record labels to get well-known celebrities and artists and performers to distribute content directly to fans on that platform. And we were pretty good at getting, you know, some notable people to use it. And then I went back to school, kind of worked a little bit part-time remotely for Gumroad, you know, ended up going, doing more stuff for Chris, the second year of school. And then when I graduated, I moved to San Francisco and I joined a company called Oneilo. which was an early player in sort of the social commerce space um that was backed by first round and floodgate and forerunner ventures i think it was part of forerunner fund one and i joined them as like the 20th hire trying to monetize this platform that had millions of users but really hadn’t generated any revenue at this point and they raised like the winter of 2013 they raised an 11 million dollar series a which in 2013 was like an enormous
Brian Bell (00:11:09):
Yeah, that’d be like a seed.
Adam Besvinick (00:11:11):
Yeah, exactly. They raised like an $11 million Series A at over $100 million valuation, which in 2013 was like, you know, unfathomable. It was like the hottest company in Silicon Valley. They’re doing a lot of the same stuff I was doing at Gumroad, but just in a different sort of market context. So I was trying to figure out how to get brands and retailers to use the platform to post their own content, drive traffic, get the Oneilo, if you remember, like the pin it button. and like the Twitter, like tweet button that would be under images on sites. We got like the Winilo button, like, you know, getting, you know, getting a line of code embedded onto a retailer’s site is a lot harder than most people might think. And so we got like the Winilo button installed so that people could easily sort of save from, you know, say from Nordstrom.com to back to Winilo. We did all sorts of store integrations with Nordstrom and other retailers, and it was a ton of fun. But really for me, it was like an excuse to be on the ground in the Bay Area full time and continue to, I kind of describe it as like a third year of business school, except got paid instead of paid for it. So I was going to all of the standard sort of like coffee shop haunts to meet with VCs before work and trying to continue to build relationships with other firms and founders and operators. And while I was there, I ended up meeting Tim Kamada, who was the founder and managing partner of a small fund called Deep Fork. And that was sort of my path to go from sort of the startup to side working at on the bd side of things at when elo to moving over to venture full time this was the summer of 2014 so basically a year after i started at when elo moved over to to the investing side at that point yeah so you probably get young
Brian Bell (00:12:52):
20-somethings reaching out to you all the time and asking you about getting an MBA. Should I get an MBA or should I start a startup or should I go to VC? I get these questions a lot because you have an MBA and I’ve done startups in VC. I get these questions all the time. I’ve actually had a lot of interns that come through Team Ignite and even get into an MBA program and decide not to do it. How do you help young people think through whether or not to get an MBA in 2025, 2026?
Adam Besvinick (00:13:17):
I think it’s a really challenging question that is very specific to the person who is asking it, right? Like if you went to an awesome school and you work in tech, there’s kind of not a lot of reason to go back to business school because you should probably have enough of a network instead of relationships and on paper track record to move into another area within business kind of broadly. Yeah. If you’ve never worked in business at all, right? Say you, you know, you’re a mechanical engineer and then you went and you worked in, you know, automotive industry you know as an engineer for three years or four years and you’re like you know what like i want to get into management i want to you know sort of transition out of this like this field then yes i think like leverage it going to a great school and using that those two years to one learn some stuff that you just don’t know and to build a set of relationships and network and use that as a transition and pivot period i think is super valuable but You know, if I think about myself, I had done two years of investment banking as an analyst and I went right back to business school after two years. I probably in 2025 could have taken those two years and gone and worked at, you know, taking my analyst experience and gone and worked in big tech. or a late stage private company for a couple years in some sort of bd corp dev role and like gradually moved over to venture right like if that was the you know sort of the destination and so i think i have a stronger opinion on what you should do after school directly like i think a lot of people are like oh consulting and banking is a waste and it’s gonna be replaced by ai but like going and working in banking or consulting for a couple years as like an analyst is like amazing training, you’re given way more responsibility than you probably should have as a 23-year-old, you learn how to have attention to detail, you learn how to take on, you learn how to work really hard, all things that you can’t just pick up organically. And so I have more of like an ardent level of support for that path right out of school than endorsing going to business school, depending on like what you did, you know? I ask you this, do you think you’d be in venture if you didn’t go to business school? I say maybe. I mean, I think like being as a student, you’re harmless. So people will respond to cold emails way more when you’re a student than when you’re a professional. And actually, I used my personal Gmail address. I didn’t use my business school address to reach out to people. But obviously, I mentioned I’m a student in school. You can see on LinkedIn, if you click through a link, he’s a student. He’s innocuous. He’s not trying to take my job. There’s just a level of help that you get as a student that you don’t get if you have a real job and you’re trying to catch up with people or get coffee or pick their brain about something. And so I think way more people responded to my cold outreach because you’re this dumb student who doesn’t know anything, then you’re in the working world. I think, could I have made the transition to venture as like, oh, go work as an associate at some firm after two years of banking, some sort of growth stage type role, and then gradually move my way to early stage? Yeah, probably. But I don’t necessarily know that the path would have been as, it may have been a little bit more circuitous if I hadn’t gone back to school.
Brian Bell (00:16:33):
So you became an operator at a couple companies and then you went into venture. Tell us about that transition and what led to, you know, ultimately Looking Glass.
Adam Besvinick (00:16:42):
Yeah, I hesitate to say I was really an operator. I mean, I had like a summer job at Gumroad where I worked a ton and learned a ton, but like, and then You know, I had a cup of coffee basically at Juanilo. But I mean, all along I really wanted to do venture. I always wanted to invest. And so when I met Tim at Deep Fork and he was looking to bring somebody on more junior who, and I didn’t really like living in San Francisco at all. So he was an SF and told him I wanted to, you know, If he wanted to hire me, I really wanted to be in New York and he was looking for someone to be on the ground in New York, then that just like worked out perfectly. And so I moved to New York that summer and then I ended up spending a week every month in San Francisco for the next nearly three years. That was sort of the condition that I had with with tim and the firm which was like i will come here monday through friday one week every month to meet with companies that are here source deals build relationships here obviously spend time with you as the managing partner in gp in person but like i want to i want to live in new york city so timing was really fortuitous like a lot of roles in venture like it just kind of like falls in your lap to a degree like just kind of like happens.
Brian Bell (00:17:49):
And so you’re, you’re, you’re one of the lucky ones to actually land a role. You know, I spent months trying to find a role myself and I had to just create my own firm.
Adam Besvinick (00:17:57):
Yeah. I mean, look, it’s just, it’s a flaw in venture in my opinion. If funds portfolio companies were managed from people perspective, the way that funds are, then like every founder would be fired, right? Like most, like most funds are really bad at people management and training and hiring and retain and sourcing talent. And as we can see over the last few years, they’re also really bad at figuring out ways to retain
Brian Bell (00:18:17):
Chain talent. This rise, I think, of AI is making us all more efficient. We see it in our portfolio companies. And I think it’s making us as VCs more efficient as well. And so I think the AUM per partner is going to go up in the industry, just like the ARR per employees going up in the tech industry, because you’re just much more efficient with AI now.
Adam Besvinick (00:18:37):
Yeah, I do think that there will be fewer and fewer junior roles, but I sort of struggle with this idea in a bunch of fields, whether it’s law or consulting or banking or venture, which is, okay, so if these junior roles are being dramatically sort of cut back because I can use AI to do the job of an analyst, like where do the VPs and managing directors come from if they don’t come from people who grew up in the industry to learn how to do the job?
Brian Bell (00:19:04):
I think it’s a great flattening of organizations, right? Because if you look back at kind of the Mad Men days of the 50s, 60s, right? You had basically a spreadsheet laid out on the floor and people are just kind of doing everything by paperwork. And it just required a huge bureaucracy and hierarchy to kind of get work done. And I think technology is like flattened organizations over time. And I feel like AI is going to be the ultimate flattener where like maybe the company of the future only has like just a C-level team, you know, 10 C-level execs that run every function and it’s just agents and AI underneath it. That might be an extreme, but what I think will happen is you’ll actually get more companies. So there’ll be more VC firms, more companies, more startups. And I think we’re seeing that. So my thesis is there’s a great flattening that happens, but there’s just less hierarchy.
Adam Besvinick (00:19:54):
I agree to that to an extent. But I think in venture, there are just so many things that you can only pick up from doing this job and having tons and tons of reps. that goes well beyond like the analysis like the analysis or like the amount of people stuff that goes on right like especially at the precede level like what we do like we’re really evaluating people you’re evaluating people and helping them navigate really like people-centric challenges in their business and who to hire and how to let somebody go and got to remove a founder because they’re not pulling their weight you kind of knew that all along but now it’s coming up right like it’s part of you know why i really think like this job is really like kind of like pseudo psychologist in a lot of ways it’s also why i like struggle with like you know like i would be way worse at this job as a man as like a founder of a firm with i were 26 versus 38 right i just think that there are so many life things that i nav help founders navigate and think through that i would be like woefully unprepared to talk about discuss be helpful with if i hadn’t had those experiences myself in my own life and in own work experiences, et cetera. And if you’re sort of extremely hands-off with the company, then you probably don’t have to think about this at all. But like if you run a concentrated portfolio and part of your, you know, sort of approach is to like be immersed in, you know, and helpful to these companies, then like I would, I don’t think I would be able to do the job the way that I do 10 years ago, 12 years ago compared to the way.
Brian Bell (00:21:18):
That’s why I usually, when I talk to people in their early to mid twenties, I tell them to go get a job basically, or start a startup because there’s just so much life to live to build up all the context. You know, what makes, I think about what like, and I’d love to hear this for you, but like what makes me an interesting GP, I think is because of all my lived experience, I’m in my mid forties now. I’ve had multiple careers across Wall Street and marketing and product and a variety of things. Failed small businessmen, failed at lots of things, probably had 100 jobs in my life. So it kind of makes me like this really awesome generalist because I’ve done a little bit of everything, like every little functional area of a company. But you can’t get that context without taking all your lumps professionally.
Adam Besvinick (00:21:59):
I completely agree with that. I also think that there’s just a lot, there are a lot of like interpersonal dynamics that emerge in this industry that you don’t know how to navigate if you’ve never seen it like as an apprentice in a fund or in other business contexts, like the dynamics on a cap table that can get messy and how to help a founder navigate those. Right. like the hard conversations that need to happen between investors in a in a business or between a founder and an investor and if you have never done this before you know you’re a founding gp of a fund and you’re 25 years old right like i just think that you aren’t sufficiently prepared to navigate these challenges and i
Brian Bell (00:22:36):
also don’t necessarily unless you started at 17 and exited one or two companies by 25 then maybe you are quite
Adam Besvinick (00:22:44):
But I also think like other funds respect firms or think about firms differently when they’ve seen who that GP is and how they’ve acted in a variety of contexts and are a known quantity. And I’ve just seen this play out again and again across companies I invested in at Deep Fork in Anchorage before starting Looking Glass and now over the last five plus years of running my own firm and over 50 investments. like, you know, and co-investing with the same firms multiple times, you start to see patterns emerge. And these are things that like only come through reps. No AI can help. No AI is going to know how did this firm operate behind closed doors when they needed to write a bridge check? Do they do it? Yes or no. And why do they do it this time and not that time? Right. And these are the types of things that I, why, you know, thankfully I don’t think this job is going to be replaced by Bordy anytime soon, despite his
Brian Bell (00:23:37):
No offense, Andrew. We’re rooting for you, buddy. Despite the oversubscription to the fund. Love that. So looking back, I mean, you know, you’ve been around this for 15 plus years. What are some of those lessons that you’ve learned that, you know, you’d like to impart upon the next generation of emerging managers?
Adam Besvinick (00:23:54):
I think that there’s been a lack of sort of like patience and it’s not just emerging, you know, it’s not just emerging managers. It’s like a lot of. A lot of LPs are really. LPs and VPs and other people. It’s more of a reflection of what’s, how things have changed since I started doing this job, really like full-time in summer of 14. Just like, this is supposed to be like some of the most patient capital. For whatever reason, it feels like there’s been a disconnect.
Brian Bell (00:24:18):
It’s funny you mentioned this. I was at a family office event, you know, kind of networking my way through the crowd and Everybody’s dressed up. It’s in Miami. And I’m in jeans and I did wear a polo. So for me in California, that’s pretty dressed up. And I’m talking to people. I’m the VC from California. And they’re like, oh yeah, but yeah, early stage? Nah, that’s like 15 years. I was like, yeah, but the asset class has the highest returns long term. You just look at any study. Yeah, but we’d like liquidity in like five to seven years. I was like, okay. And there’s this short termism, I think, happening.
Adam Besvinick (00:24:51):
Yeah, well, I think it’s both like liquidity short termism, but also like markup traction progress short termism in a way where like there’s a sort of misalignment that if something doesn’t get big quickly, like it can never get very big. And that’s just been proven again and again and again to not.
Brian Bell (00:25:08):
Sometimes you wallow for four years like Notion did. I think Airtable did that.
Adam Besvinick (00:25:12):
Yeah, like there’s this, you know, and so, you know, you, I think Figma, I think Figma didn’t grow for like. Figma took quite a while. Monday.com took quite a while. Stories again and again of like these companies struggling to find product market fit and they’re really needing to like tinker with what they’re working on before it catching on. Then you have obviously over the last, you know, 12 to 18 months that, you know, we all have seen the chart where like at a certain point, the line is just going to go vertical. Someone’s going to be at a hundred million dollars in ARR in a week. Kind of the lovable, you know. Well, the lovables and cursors, et cetera, I think that these companies are, they’re basically giving other companies the company equivalent of like body dysmorphia. Like some of these things are just not realistic right it’s like looking at you know a kardashian and thinking that that’s like what a human body is supposed to look like startups are meant to grow at an unnatural rate and you raise venture capital to grow at a rate that is not what a normal company is supposed to do but i think we’ve kind of lost sight of like what a really great company can look like yeah the triple triple double double double
Brian Bell (00:26:16):
has become like the 10x 10x 5x 5x 5x
Adam Besvinick (00:26:20):
Right. And I just think that if you’re an early stage investor, you knew what you signed up for. Right. Like ignoring the LP conversation, but like the sort of the GP fixation with like, oh, well, it’s not growing fast enough for me. They only grew how much this year? They only grew 5x 2 million to 10 million. Well, that’s not that’s not fast enough for me. And I think that it’s doing a disservice to, frankly, a lot of founders who are building stuff that’s really valuable and is going to be really valuable. But there’s sort of the number of funds that are willing to look at some of these companies is dwindling. And then the funds that do now feel like they’re being adversely selected because, well, why did I get a look at this? If it was so great, wouldn’t name your tier one, name your top five, top 10 fund, wouldn’t they have done this deal? And so it’s a challenge that I think about a lot with companies in the portfolio and how they think about positioning and who the right investor is for them and how do they tell that narrative and how do they help people understand the customers that we’re selling into can’t just like put down a credit card and start paying for this thing, right? Like take six months for them to start paying, but they’ll pay us a million dollars, but it’s going to take us a while to. And they’ll never rip it out.
Brian Bell (00:27:26):
Yeah. Yeah, this is the art versus science of being a VC, right? Because you have to kind of look at the painting and really appreciate all the brushstrokes or all the threads of the tapestry of the startup.
Adam Besvinick (00:27:40):
Yeah, I mean, that’s a great analogy. I think that the challenge that I foresee for some companies is, to me, there’s like a misalignment at like Series A right now.
Brian Bell (00:27:51):
Yeah, there’s a weird gap right now between C and A.
Adam Besvinick (00:27:53):
Yeah, I just feel like the universe of funds that do Series A deals is largely populated by multistage firms. And they need to write a check of 12 to 15 million or more. Yeah, 15 to 20% ownership. To do an A. And there’s a lot, there are going to be a lot of companies that don’t need to raise that much or don’t want to raise that much Series A. And who writes that Series A check? There are fewer and fewer firms well positioned to invest in an old school. It’s not even an old school Series A. It’s like a, you know, it’s a 2018 Series A.
Brian Bell (00:28:27):
Yeah.
Brian Bell (00:28:28):
And meanwhile, if you have companies growing very capital efficiently, I don’t know what you’ve seen in your portfolio. I’ve certainly seen it over the last five years. I haven’t been in the industry as long as you have, but you have historical context on capital efficiency in the pre-seed seat in A. At least in the last five years with AI, I’ve definitely seen maybe a doubling of capital efficiency. I don’t know what your back of the envelope calculation is over time.
Adam Besvinick (00:28:53):
Yeah, I mean, I don’t know if I have a definitive multiple on how much more efficient some companies have gotten, but I do think there’s, at a minimum, it’s a headcount reduction, which is translating to some degree of capital efficiency. The number of people that you need to hire to ship X amount of product is just significantly lower now than it was even in 2021, let alone 2021.
Brian Bell (00:29:18):
I just met a founder yesterday, second startup. They raised way too much money in the first one, like 20 million. And like, we’re not going to do that this time. We’re going to do very small rounds with, you know, well-defined, you know, three or four X per dollar spent kind of capital efficiency. And they already bootstrapped it to almost a million of ARR without raising money. Just two guys. I see this all the time, right? Like, if you can’t get to some six-figure ARR bootstrapping, you know, I’m probably not interested. Unless it’s like a deep tech and it’s like long enterprise sales cycles and you’re like a crack team, perfect for it, right? So there’s nice exceptions, you know?
Adam Besvinick (00:29:55):
Yeah, there are exceptions. I think... I think there’s basically no exception for having shipped something these days. The idea of investing in anything pre-product is like, I’ll do it, but only for an exceptional team. But in reality, there’s no excuse. Anyone can vibe code something that feels like a bit of a prototype to give me a sense for what this thing is going to look and feel like, even if it’s not your actual product. Before, it used to be like, all right, if you can’t show me wireframes, what really like even like drawn now obviously the bar is significantly higher with all the tools that we that we talked about and so there’s there’s almost not even almost there’s zero excuse for not having something that an investor can play around with and you can put in front of customers to get feedback on and it just shows a level of commitment to the idea and what you’re building that for me as an investor like my the bar for me is like if i say no you should still be working on this idea I think way too many founders think that if a bunch of investors pass, then it’s not, that it’s like invalidated. And conversely, if a bunch of investors say yes, that it validates what they’re working on. When in reality, they’re completely, they’re largely disconnected from one another.
Brian Bell (00:31:07):
And some of the best things kind of look weird and non-consensus as well. So a lot of investors might pass on a really good idea because it just looks too strange.
Adam Besvinick (00:31:16):
Yeah. I mean, that’s, if everyone wants to do a pre-seed super early stage deal at a low valuation, then there must be, well, one, it won’t be a low valuation. It’ll get bid up. But if everyone thinks something is a sure thing at pre-seed sort of prototype, few grand a month revenue stage, it’s probably not gonna work.
Brian Bell (00:31:34):
So tell us about the moment where you knew that you needed to launch your own firm.
Adam Besvinick (00:31:39):
I think I was sort of, well, when I joined Anchorage, which was the hedge fund that I was at after Deep Fork and before starting Looking Glass, I went there because I wanted to round out my skillset as an investor. I had done seed for a few years. In 2025 terms, it was really pre-seed. It was a $30 million fund, 250 to 500K checks. million to $3 million round. So it was a lot, it was very similar to Looking Glass now. And I just repeatedly felt like, you know, I had friends telling me like, oh, well, what you’re, what you’re doing isn’t really investing, right? True investing is writing a larger track, having to lead the round, having to price the deal, et cetera. And while I didn’t necessarily agree with that and don’t necessarily agree with it now, I do think that they’re obviously leading a series A is wildly different than even leading a pre-seed round. And so I wanted to get that experience. And there was an opportunity at Anchorage to do that. And they had been making some growth stage opportunities and they were looking for someone to do earlier stage deals. And so I joined them for about two and a half years, made half a dozen investments, mostly series A’s. I mean, I put more capital to work in a single investment at Anchorage than I put in to 14 investments at Deep Fork. I was doing five to $15 million checks at Anchorage. And I think I did like 5.3 million combined, 5.4 million combined in 14 investments at Deep Fork. So it was a tremendously different experience. You had to lead rounds. You had to source differently. You had to price those deals and taking board seats. And I was surrounded by really sophisticated, thoughtful public markets investors who really put me through my paces in terms of memo writing and underwriting the deal and how do you convince large investment committee to do something. But it also got to a point where I was like, all right, I know I don’t want to do this stage of investing forever. I missed the first money in, two people and an idea. Let’s brainstorm and tinker and think about different go-to-market strategies and hey, you don’t have product market fit. Let’s come up with some different ideas to test and iterate on. And I also candidly felt like if, and I feel this way even more so now, if you’re not at one of a limited number of Series A firms, you shouldn’t do Series A investing. We made some great investments and we’ve had a couple of very significant exits from those investments that I made. But in my opinion, Series A is pure play quintessential venture investing. And it’s done best by a relatively finite set of firms.
Brian Bell (00:34:06):
Yeah, multi-stage mega firms that have a billion or more AUMs.
Adam Besvinick (00:34:11):
If those firms don’t do it, it’s highly unlikely that what you’re doing is something that escaped their gravity. Occasionally it is, but it’s probably not. And so I wanted to take the sort of institutional discipline that I saw firsthand at Anchorage, but apply that to small fund, early stage, pre-seed sort of strategy. And I just felt like... You know, in late 2019 when I was doing this and started January 2020 when I started fundraising, like that felt novel to me. And then... you know, let’s ignore the few months where I thought everyone thought the world was ending. But then, you know, suddenly you had this sort of like Cambrian explosion of funds that launched at the end of 20 and 21. And it really hasn’t slowed, but there was definitely like a massive influx in late 20, early 21. And it felt like my strategy was like even more stark contrast to what the behavior that I saw from lots of you know, fund ones, emerging managers during that time. And so I just felt like there was an opportunity to fuse sort of like institutional discipline and portfolio construction and fund math and underwriting, but do it at the earliest stages where I felt like those things were largely like disconnected. And I felt like the positioning of the firm was one that could serve both in my strategy, could serve my two customer bases, like equally well for different reasons.
Adam Besvinick (00:35:36):
So like, LPs who generally, not all, but many of them want you to be more concentrated. Many of them want you to own more of these companies. Many of them want you to lead and invest with independent conviction and sort of the tropes of... you know, a venture.
Brian Bell (00:35:52):
How much of that is just traditional thinking?
Adam Besvinick (00:35:54):
I think there’s a lot of merit to it. And I’ll, I’ll, I’ll, I’ll double back on it. And then the other side, the other customer base is your founders, right? And founders don’t care about my, my business model, but they do want someone who invests with independent conviction. They do want someone who is willing to lead. They do want someone who writes a, a check that really matters, right? Like disproportionate amount of my, you know, fund size. All of these things that demonstrate that I 100% believe in them. This is not a call option. Can it go to zero and still work? My funds will work? Of course. I don’t have five companies in the portfolio, but it’s concentrated enough that it demonstrates really serious alignment with them. And so I felt like this strategy and this model served my two customer bases equally well, but for sort of like different reasons, right? And so I felt like that approach was more novel at the precede sort of earliest, you know, sort of micro VC fund size perspective. And felt like there was a market for that, both with founders and with potential LPs.
Adam Besvinick (00:37:02):
And so that was sort of the elevator pitch, so to speak, when I went to market raising for fund one. And it’s early still, it’s working.
Brian Bell (00:37:10):
Coming out of the J-curve now on fund one?
Adam Besvinick (00:37:12):
Out of the J-curve on fund one, out of the J-curve on fund two, well out and sort of raising fund three now. So feel like there’s enough momentum and enough changes between fund one and fund two where fund two is ramping more significantly than fund one. So like things like, you know, the less sort of the lessons learned from, you know, investing during the chaos of Zerp, you know, still quite disciplined, but still not as, you know, still more expensive deals than for fund two, but like lessons learned during that period have translated well to fund, to fund two, and hopefully lessons to take from deploying funds to, to Trent to transition to fund three.
Adam Besvinick (00:37:52):
But yeah, to your question on sort of like concentration versus larger portfolios, I think it kind of needs to align with your sourcing strategy. It needs to align with the type of investor that you are. I am not the type of investor that feels like I can see every hot, buzzy deal because to me, that’s what you need. You need to feel confident that you’re seeing everything that could potentially be a $25 billion plus company if you’re only going to be investing a smaller company. amount of capital, or you’re going to be investing at slightly higher valuations or six of one, half a dozen of the other. That was why I think personally, I don’t think I would be a very good series A investor, even if I were at Sequoia. Like I think to me, the being a great series A investor means you need to see things that are shades of gray between interesting and compelling and everything looks interesting basically. but like what is truly compelling. And if you’re investing at a 75 or a hundred million dollar valuation at the series A and that company becomes a billion dollar company, which is really hard to do, right? And exits for a billion dollars. Like it’s not that great of an outcome. In fact, it’s like quasi like failure of an outcome for that multi-billion dollar fund that wrote that $15 million check, right? you’re shooting for $5 billion, $10 billion, $25 billion plus outcomes.
Adam Besvinick (00:39:06):
And so it’s part of why I wanted to go back to this earliest stage is because I think I’m really good at figuring out, can this be anything at all versus, versus nothing i don’t think i’m very good at can this be a 10 billion dollar company instead of a billion dollar company and there’s some people that are extremely good at that and you know we can name them pretty easily you started your career as one of them yeah chris is arguably one of the best well i think he was even better at like could this be anything right like that’s like the first money in thing
Adam Besvinick (00:39:33):
Right. Like, and I think if you own a lot less of a company or you write smaller checks or whatever, one of the two, then you need to be really good at knowing whether this could thinking you’re seeing something that could become a generational outcome, because that’s what you kind of need to have to make that fun math work. Whereas for me, like, I think I’m much better at saying like, do I think this could be worth several hundred million dollars to a billion dollars at some point and a billion dollar out. And like my fun math is such that a billion dollar outcome returns my fund.
Brian Bell (00:40:02):
Yeah, I’ve had this discussion with LPs on the pod before. And we debate this because I’m a high volume small check investor, right? And the way I looked at it was with a Monte Carlo analysis and various probabilistic reasoning. I’ve written a lot of articles on it, you know, because I put my CFA brain on, my finance degree brain on. And I was like, okay, like how do I efficiently allocate in this pre-seed asset class? And if you look at the math of it, and AngelList has a really good study on this. If you invested in every deal on AngelList, you’d be in the top 20% to 25% of all VCs. And you’d have a 25% IRR, I think it was, in the study. Yeah, there’s always this push and pull between the concentration...
Brian Bell (00:40:41):
and diversified. Spray and pray or spray and select is what I call it. It kind of fits with our thesis at Team Ignite. We’re trying to build this network that kind of helps each other. YC does 600 deals a year. They have the social network there with over 5,000 startups that all help each other and sell to each other and sell with each other and partner. Kind of what we’re trying to build at Team Ignite. It just kind of fits my personality too, I think.
Brian Bell (00:41:03):
I can see you as a GP. You want to dive deep. You want to help the founders make more concentrated bets. And that’s just your personality.
Adam Besvinick (00:41:10):
Yeah, I think that it’s a sourcing model. I think it would be wrong if I was like, I’m just going to write 100 checks, 100, 100K checks, and just be hands-off, check-in maybe quarterly. It’s the founder product, founder market fit. question that like you and I think about when we meet any company, right? Like, or similarly, like, you know, it’s the founder that’s been in sales their whole life and they’re like, you know what, but I’m going to do product-led growth for this company that I’m starting. It’s like, well, no, you should probably play to your strength on go-to-market, which is, you know how to sell really well. And the product-based founder should be doing PLG, not trying to do enterprise sales, right? Like, and so there is an alignment of skills and personality and background and what keeps you engaged that I think also helps inform fund portfolio construction model that I think gets overlooked.
Brian Bell (00:42:00):
It’s interesting. I think the holy grail of VC is probably like a 10x fund. That would put you in the top single digit percentage of all VC funds. And if you hit the average or the asset class, call it a 20 to 25% IRR, you’re going to have roughly an 8 to 10x gross fund. But a lot of VCs don’t hit that because they’re not good at picking or adding value or whatever, whatever the reason is. And so statistically, we just set ourselves up for success by investing a lot of deals. But time will tell. I’ve never met a fund manager with over 100 in their fund that had less than a 10x fund. And this is like dozens of people I’ve talked to at this point over the years. They’re like, oh, yeah. Like Ron Conway’s strategy, right? 300. I think he had like 300 in his SV Angel 1 or whatever. And I think it was a 12 or 13x fund. Yeah.
Brian Bell (00:42:48):
So it’s really interesting. But yeah, it’s not for everybody. It’s really hard, actually. I have to do a lot of AI and automation and connecting people. It’s very hard. Not easy. It’s just different.
Adam Besvinick (00:42:58):
Yeah. No, it’s a different sourcing strategy. It’s a different way to help post-investment. The entire job looks probably very different, actually.
Brian Bell (00:43:08):
Yeah, no, it is.
Adam Besvinick (00:43:09):
It’s a lot of orchestrating.
Adam Besvinick (00:43:11):
Yeah, a lot more different than people would expect.
Brian Bell (00:43:13):
Yeah.
Brian Bell (00:43:15):
I asked the LP this question. I’d love to get your take, which is, you know, if you had a fund, you’re looking at two funds, right? And one fund had, you know, 30 investments and one really knocked it out of the park, right? Returned the fund, you know, three or four X over and ended up with like a 5X fund gross or something like that, right? And it had a bunch of singles and a bunch of zeros. And then you had another fund that made 30 investments. But virtually all of them are about 5x returns. So a bunch of doubles, call it. Which fund are you happier with?
Adam Besvinick (00:43:48):
I had this conversation with an LP, myself actually, because I think that there’s this view that if your attrition rate isn’t, if you’re not getting a bunch of zeros or less than one Xs, then you’re not taking on enough risk. I think it’s totally reasonable if you’re investing at seed in A, I think at pre-seed, it’s hard for me to say that a low attrition rate means I’m not taking on enough risk because it’s all risky. It’s all risky.
Brian Bell (00:44:21):
Yeah.
Adam Besvinick (00:44:22):
All risky.
Brian Bell (00:44:22):
These are all two people with an idea and maybe...
Brian Bell (00:44:27):
I had a VC tell me this the other day. He’s like, well, if you’re not getting... Because I’ve had very little shutdowns in my career. And probably because I kind of invest like you. I look at founder market fit, traction momentum, something unique. And there’s a moat here, a distribution advantage. They know how to sell or do PLG, whatever it is, right? And out of almost 300 investments I’ve made, I’ve only had in five years, five or six years, like maybe seven or eight shutdowns. So it’s very, very low attrition rate. Now there’s probably another 30 or 40 in there that are the walking dead and they are going to shut down. But still, that’s pretty low. I think when you look at a fund model, you’re anticipating 50 to 60%.
Adam Besvinick (00:45:04):
Yeah, I’ve had three or four out of the 53 companies so far.
Brian Bell (00:45:09):
Yeah, that’s very low as well.
Adam Besvinick (00:45:11):
And so now, yeah, there’s probably two to three, like on my ratio, there’s probably two to three, like kind of they’re like, you know, at some point they will. But like, I also think it’s a testament to the types of founders that you mentioned, you underwrite, you do all this diligence, but also like there’s a natural level of resilience, in my opinion, from certain founders, like the unwritten agreement I had dinner with the founder in the portfolio last, actually on election night last year. I was in San Francisco. If you ever want to make sure you get upgraded, fly on election day because no one’s traveling.
Brian Bell (00:45:41):
Nobody’s traveling.
Adam Besvinick (00:45:42):
No one’s traveling. And so I flew to San Francisco on election day and I had dinner with the founder of the portfolio and she and I were talking and I said that there’s an unwritten, unspoken agreement between founder and investor that makes this whole ecosystem beautiful and really work well, which is we give you money, basically no strings attached money. And if the company does not work, you basically can walk, as long as you don’t commit any sort of ethical or financial fraud, you can walk away scot-free. As long as you tried your hardest to make this thing work and figured out how to shut it down gracefully and did everything you possibly could to make it a success.
Adam Besvinick (00:46:21):
Cool.
Adam Besvinick (00:46:22):
Hey, there’s no need to apologize. I know what I signed up for. You know what you signed up for. And I think that there is a...
Adam Besvinick (00:46:29):
And those are the types of founders that you hope you back, right? And you don’t know how someone’s going to behave until, like, you know, the rubber meets the road and things get hard and whatever. But, like, there are a number of founders in the portfolio whose companies probably should have already shut down. But they are resilient. They know what they signed up for. They cut their salaries to extend burn. They’ve figured out all sorts of ways to... all voluntarily, right? They’ve figured out all sorts of ways to extend runway, to give themselves another chance at figuring out how to turn over another card and see if this, you know, can they grow fast enough to, you know, to raise another, you know, bit of capital and extend runway. And I think also the types of companies that I’m backing attract resilient entrepreneurs, right? If you’re going into healthcare, if you’re going into climate and energy, if you’re going to education, oftentimes, like these are like very fraught, regulatorily complex companies industries that you’re attracted to building and probably because of some like deep seated personal mission centric reason. And so you’re probably less likely to throw in the towel or give up than maybe some other categories that attract more casual, fly-by-night founders. And so, yeah, I think that there’s just an appreciation for the venture-investor-founder relationship that some founders have. And I think that there are a lot of founders that don’t have an appreciation for it. And fortunately, I haven’t backed any, or maybe one or two in my life. And so I think that to me is also part of this dynamic.
Brian Bell (00:48:05):
Yeah, and part of your thesis too. Maybe you could tell the audience what Looking Glass does and what your thesis is.
Adam Besvinick (00:48:10):
Yeah, so as Brian mentioned at the top of the call, and I just referenced, so I’m investing in three core areas, healthcare, climate and energy, and this third thematic bucket called economic drivers, which for me includes education and tools and platforms for small businesses. And so largely investing in a lot of software and application layer stuff across these categories, pre-seed, loosely defined. So generally these are round sizes between a million and $2 million, first couple of million dollars into a business. Valuations are typically between five and 12 million, five and 12 million posts kind of hovering around like the eight, eight and a half range on fund two. And I like leading or co-leading out of fund two. I have a couple more investments to make, and they’ve typically been about 350 to 400 K checks and out of fund three, I’ll be writing 500 K to $2 million checks. But again, the same, same stage, same categories.
Brian Bell (00:49:03):
um and how many checks uh per fund 30 okay yeah that’s i pulled that out of my head
Adam Besvinick (00:49:08):
yeah yeah fun one was a little smaller fun one was 24 fun two might be 31 because there’s just a little bit you know there was a couple a couple smaller in the 300k range um yeah somewhere around 30 i think it’s the right number for me to to manage and get my sort of balance of ownership versus shots on goal and yeah and it’s So OGP, just me trying to be as helpful and supportive to companies in the portfolio as I can.
Brian Bell (00:49:34):
Yeah. Do you have any assistants or part-time people or anything like that? Just doing everything?
Adam Besvinick (00:49:39):
Everything.
Brian Bell (00:49:40):
You should probably get yourself at EA at this point. You know, at least an MBA level EA overseas or something. Athena Go or something like that.
Adam Besvinick (00:49:46):
I think that, you know, in the fullness of time, I think the model for me is a chief of staff who’s like part ops, part associate, part research, part diligence, part portfolio manager, all that. It’s a mix of basically the role that I, like a full-time version of the role that I had with Chris,
Brian Bell (00:50:03):
basically.
Brian Bell (00:50:03):
Yeah.
Brian Bell (00:50:04):
That’s basically what I have. I have an EA that’s been with me for like four years. I found her on Upwork. She’s great. And she just kind of, I just throw stuff at her and she just gets it done. So like, great. She’s halftime with me for four hours a day. She’s great. Can’t say enough about my EA. Shout out to Katharina. How has fundraising shifted for you from like fund one, two, and to three? You know, fund one, of course, is all just people we know, rich people we know, writing us checks. Fund two, you start kind of breaking into some family offices. What’s fund three looking like? What have you learned about fundraising, asking for a friend?
Adam Besvinick (00:50:32):
I think fund... Well, don’t start your fundraising in the throes of a global pandemic. Fund one. That’s good advice.
Brian Bell (00:50:40):
Or the throes of, like I did my first close of my traditional fund in late 2022.
Adam Besvinick (00:50:46):
Yes. So I was fundraising for funds to late 22 through 23.
Brian Bell (00:50:54):
Same.
Adam Besvinick (00:50:54):
In the 24.
Adam Besvinick (00:50:56):
Yeah. So that was two and a half years.
Brian Bell (00:50:57):
It was a two and a half year fundraise for a $5 million fund.
Adam Besvinick (00:51:00):
That was worse. That was worse than COVID fund three.
Brian Bell (00:51:04):
I’m raising now another, like basically a $5 million fund, but I’m not even paying attention to the fundraise and I’m still kind of just raising money.
Adam Besvinick (00:51:11):
I think that the two things that I learned that I’ve done much better this time than I did on the prior one, one is I spent time in between fundraisers actually talking to LPs. Now I send out a letter every eight weeks to my own LPs and to friends and followers of Looking Glass. And I do that without fail every other month. So, and out of 900 people on that friends and followers list, most are potential LPs and the open rate’s like 60%. So like people are looking at my updates, but there’s something very different than sending an email update versus like getting on a 30 minute zoom call or telling them you’re in town and getting coffee and whatnot. I’d run a much better job of maintaining relationships and sort of building dialogue in between the fundraising for fund two and fund three. And I think that’s been a huge advantage with this fund three process.
Adam Besvinick (00:52:01):
I think that This is true, and it’s true for reasons. These things take time, and they are largely multi-year relationships prior to someone making a commitment to a fund. Obviously, there are exceptions, and those exceptions are probably family offices and individuals, not fund-to-funds or institutional, quasi-institutional allocators. I talked to somebody about Fund 3 and he’s like, oh yeah, we’ve been talking for five years and you did exactly what you said you were going to do. You could have been part of Fund 1.
Brian Bell (00:52:31):
Fund 1 is doing really well, by the way.
Adam Besvinick (00:52:34):
But yeah, I think that there’s a lot of people that raise and then their strategy shifts. They start overpaying for stuff. They chase shiny objects. And I think... The bar for just doing what you say you’re going to do as a venture investor, both on behalf of LPs and on behalf of founders is like shockingly low. And so when you just show up every day and do the work and obviously results need to speak for themselves, but like doing it in the process that you outlined you were going to do, that stands out a lot to people.
Adam Besvinick (00:53:05):
And so I also think like just getting to a certain point in firm building indicates a level of success and a level of like sustainability and determination. It’s the same way that like if a company is out raising a $20 million series A or a series B, like they have to have been doing a bunch of things right to even get to that point and even have the confidence to try and raise that much capital. Right. The same way that like if you’re out raising fund three and it’s, you know, oh, you’re This was how much fun one was. This is how much fun two was. This is how much fun... Oh, okay. Things must be going pretty well. No one just gives... This isn’t a charity. No one’s just giving you money so you can employ yourself. And so I think getting to fun three, the same way if you get to fun four, the level of attrition for people that make it to a fun three or make it to a fun four is so high that if you get to that point, there’s signal-embedded in the fact that you’ve even gotten to that level.
Adam Besvinick (00:53:59):
And so way more people respond to your updates, are willing to take meetings. And it’s like, oh yeah, you’re raising a $30 million fund three. Okay. Like you must have something going for you. I don’t necessarily need to take this through a warm intro. Whereas when you’re raising an $8 million fund one or $5 million fund one, people are like, how did you get my email address?
Brian Bell (00:54:17):
Yeah.
Brian Bell (00:54:18):
Who are you?
Brian Bell (00:54:19):
Unsubscribe, please.
Adam Besvinick (00:54:21):
Yeah.
Brian Bell (00:54:21):
Please stop.
Adam Besvinick (00:54:22):
I get a lot of those. Please stop. Oh, that’s funny.
Brian Bell (00:54:24):
Well, what are you excited about looking forward? Next five years or so?
Adam Besvinick (00:54:27):
I think from a firm perspective, to me, the most fun and most enjoyment I get out of doing this job is just seeing... you know, seeing companies grow, going to offices and seeing like them filled with people. Cause that’s like one of the things that you think you take for granted in this is like, wow, you’re actually like part of job creation. Like you largely only interact with founders and CEOs in this, in this role. You don’t oftentimes get to meet the people that those companies hire. And so like, like two weeks ago, I went to an office warming for a company that’s like like they just opened a new office and they have 30 employees right like and meeting people that just started working there you know two months ago because they raised a series a and they’re ramping up and hiring like to me that’s like one of the most rewarding parts of of doing this job and like i’m excited to see how these businesses like actually grow from a sustainable perspective not just raise follow-on capital and get markups that’s nice too but it’s an outgrowth of like actually like building enduring companies from a tech and sort of invest in perspective, to me, I’m most excited to see some of the, kind of want to see like the shakeout of this wave of the last two years. Not because I think stuff is overvalued, which I do think it is, but more to see like what actually sticks around as core products and core businesses that end up shaping the way that technology gets built over the next five to 10 years versus which things were kind of shiny objects, flashes in the pan that
Brian Bell (00:55:55):
What are the work spaces versus the AWS?
Adam Besvinick (00:55:59):
Yeah, exactly. And what do new types of companies actually get built in the long run because of the stuff that stuck around? I had a very interesting line of demarcation between Fund 1 and Fund 2, which was the launch of ChatGPT, which basically bifurcated the end of Fund 1 and the deployment of Fund 2. And so if you look at the profile of fund one companies versus fund two companies, it’s markedly different just because that’s what founders were attracted to building and drawn to building. And so I think, you know, since over the last three plus years of deploying fund two, things again have made, obviously shifted wildly again. And so I’m excited to see how that plays out in fund three. I think even more so, it’ll have even more market sort of effect on the makeup of fund four, three and a half, four years from now.
Brian Bell (00:56:43):
Fascinating. Well, let’s wrap up with a quick wrap up of rapid fire. Which founder taught you the most about resilience?
Adam Besvinick (00:56:50):
Well, I’m not going to call out either of these founders by name, but I’ve had two founders who, one whose spouse was diagnosed with cancer and he’s healthy and recovered fine, but was diagnosed with cancer in the middle of building her company. And another whose daughter was diagnosed with cancer and she’s on the road to recovery, but still like an not 100% there. And both of those founders have been, to me, it’s a reminder that life is happening around these companies. As much as you as an investor are just thinking about, I’m underwriting this person as in their experience and their skillset and all these things that we’ve talked about on this call, there’s all sorts of other stuff going on. And life doesn’t just stop because you’re trying to build a billion dollar business. And so those two founders just sort of like And by the way, both companies are doing extremely well, like insanely well, despite all of the really hard emotional mental tolls that both of these entrepreneurs had to contend with and are contending with. And so to me, like there’s all sorts of other definitions of resilience, but to me, like those two women stand out in terms of their level of determination, like above and beyond any, any founder that I’ve, that I’ve worked with.
Brian Bell (00:58:05):
What’s a belief about pre-seed investing you’ve reversed in the last five or 10 years?
Adam Besvinick (00:58:09):
I think probably early traction doesn’t matter. I used to overweight early traction, I think, a lot as a bias that I had. And now I don’t write it off entirely, but I’m way more sort of self-aware of that as an implicit bias that I have when evaluating a company is if they have early traction, I think more highly of them. And I just needed to learn through prior mistakes or seeing how companies sort of progressed post that initial pop, that some things are a false positive or some things just aren’t sustainable or enduring. And so it’s one of the things I think about as a solo GP who doesn’t have checks and balances on my decision making is I need to be hyper aware of how I think about underwriting investments and any biases that I have and making sure that I strip those away. And this is one that I’ve kind of learned to sort of more easily notice and reconcile since i started doing the job
Brian Bell (00:59:08):
yeah i’m the same i think i used to overweight traction as well and now it’s a little bit of the kaleidoscope of everything what’s the most helpful question a founder has ever
Adam Besvinick (00:59:14):
asked you that’s a great question i don’t know if it’s necessarily the most helpful but as a question that i don’t think enough founders ask you know somebody was just like i think you need to put founders on the spot or put investors on the spot more it’s a tenuous balance as a founder to to do that but like really digging in on why did you take this meeting? Why are you excited about what we’re building? Versus just going through the motions. All right, this is what Looking Glass is. Great, you do your pitch. Let me ask some questions. It takes a certain level of charisma and confidence for a founder to start a meeting and a conversation like that. And some investors might completely take it the wrong way and be very pissed off. Those are probably investors you don’t want to work with. So this might be a good way of weeding. weeding them out. But when a founder asked me that, and it’s happened, it doesn’t happen frequently, but it’s happened a bunch, enough that I remember the time, like, not so much that I remember specific times,
Brian Bell (01:00:09):
but there are- It always catches you off guard. I do get that question, you know,
Adam Besvinick (01:00:11):
every, probably once a month or a couple of times a month, I’m like,
Brian Bell (01:00:12):
probably once a month or a couple of times a month,
Adam Besvinick (01:00:14):
oh.
Adam Besvinick (01:00:15):
Yeah, I’d say it’s once a month, a couple of times a month that I get that. And I’m like, okay, like, this is going to be an engaging conversation. I’m going to be on, like, this isn’t just a founder who’s like in lean back mode, it also sets the tone for probably how their process is going. If they feel like they can sort of start the conversation with me answering questions about the company or the space. And so I always think that’s a dynamic that I appreciate. It feels like I’m being cold called in a business school class.
Brian Bell (01:00:49):
It’s a good sales technique too.
Brian Bell (01:00:52):
What are your pain points right now?
Brian Bell (01:00:54):
Why did you take this meeting?
Brian Bell (01:00:56):
I love that. Is it a negative signal when both the founders are on the call?
Adam Besvinick (01:01:01):
I don’t think it’s a negative signal if both founders are on the call. To me, it does potentially lead to a vulnerability, though, because I’ve definitely had times where the CEO just completely deferred into answering or was talked over. And to me, that’s a red flag. And so just know that some people are going to be extremely turned off by that.
Brian Bell (01:01:22):
I think the CTO should just be building and the CEO should be fundraising.
Adam Besvinick (01:01:25):
Well, on a first call, it’s one thing, right? Like just CEO, but like a lot of times, like I want to talk to the rest of the founders, right? Like on a second conversation, third conversation. And so if you have two non-technical founders that are clearly like really driving things, like I just backed a company, two non-technical founders, both showed up to the call. I know they’ve taken a lot of their pitches together. They are very complimentary to one another. It’s a core part of the story and narrative so i don’t have a problem with that non-ceos reaching out to schedule meetings to for reaching out to investors that to me never works yeah what are you having your associate do this yes yes or coo co-founder you know what like just all sorts of you know nonsense and that that i i don’t take those
Brian Bell (01:02:12):
meetings i don’t take especially in precede maybe an a that’d be fine but deck demo or conversation on the first call
Adam Besvinick (01:02:19):
All of the above. To me, it’s whatever is going to help you do your job the best. I do not like when a founder says, so how do you like these meetings to go?
Brian Bell (01:02:27):
I don’t like that either.
Adam Besvinick (01:02:28):
Just own the discussion. You need to own the room, even if the room is you staring at your laptop. Get what you need out of me as the investor to know have context, which I’m happy to do, and I always keep it super brief because the story is way more interesting coming from the founder than from me. But if you want to walk through a deck, walk through a deck. If you just want to do a conversation, do a conversation. If getting to a demo quickly helps position the business and the product better, do that. But do not defer to the investor. Like you’re the storyteller. You know what your strengths are as a fundraiser and someone pitching. So just do that.
Brian Bell (01:03:05):
What’s a contrarian view you hold about building a venture firm in today’s environment?
Adam Besvinick (01:03:09):
That everyone should do it. Like there are too many funds. Like why does everyone need to have a fund? Why does everyone need to spin out? Why can’t people just work for somebody else for a while and then learn and then maybe go and start a fund? Right. Like too many people in their early to mid twenties who think that they should be doing venture and just raising funds off of access. That’s, that’s my country. Sadly, that feels contrarian and maybe it’s going to get me canceled or something, but yeah, way too many.
Brian Bell (01:03:35):
You’ll get an ex flame storm.
Adam Besvinick (01:03:37):
Yeah, way too many young early to mid-20s something starting funds who have never had jobs, who have never worked at another venture fund before.
Brian Bell (01:03:47):
What’s a book, essay, podcast, or talk that influenced how you think about founders?
Adam Besvinick (01:03:52):
I don’t know that I have one in particular that has really struck me. I kind of don’t like reading about my job. The only podcasts I listen to are when people I’m friends with are on them or I happen to be on. Reasonable. I don’t listen to All In. I don’t listen to TBPN. I listen to Bill Simmons. I listen to stuff that takes me out of my day-to-day work zone. I read stuff that’s just pure fiction, maybe some historical fiction, non-tech related stuff.
Brian Bell (01:04:24):
You’ve crossed over to the mature VC that is just like... Because we work so hard. I know we get a bad rap, but we actually do work really hard. And so I just... It’s actually really awesome where I live. I live east of Sacramento on Lake Folsom. And nobody cares about VC out here. Nobody knows what I do. They’re like, what is that? Like Shark Tank. And so it’s great. As soon as I leave my little home office, nobody cares. I’m not in the San Francisco or New York City hubbub of like, how much did you raise? I’m just... Chilling by a lake with deer in my front yard.
Adam Besvinick (01:04:56):
Yeah. I, uh, I don’t know. I like watching my Philadelphia Eagles and my Duke basketball team. And I kind of, whatever, I plug in for way too many hours per day and week. And I’m, you know, tethered to my, you know, tethered to this, you know, digital leash. And when I don’t have to take pitches or fundraise or support portfolio companies, I want to take a breather and disconnect. I mean, I think honestly, like I learned a lot of that from like Chris, right? Like he moved out of San Francisco to, trucky and disconnect he’s like look i’m gonna be a better investor removing myself from that’s like an hour for me that’s not that far the chaos of of san francisco and the valley and think more clearly and i think yeah like i i don’t know i i kind of if i were 25 or 26 doing this when i started like i would i went to every event you know there was the performative nature of being busy and hustling and all that stuff. And I’ve got three kids and, you know, I, I would, I’d much rather do sitting in that excess time, running around with my kids on their bikes, then trying to consume one extra incremental, you know, 20 VC pod.
Brian Bell (01:06:04):
No offense, Harry.
Brian Bell (01:06:06):
Oh, you’ve been on 20 VC. That’s awesome. Yeah. Like Harry, he’s such a workaholic. He works so hard. But he’s like in his late 20s, right? He’s like 28 or something now.
Brian Bell (01:06:13):
Yeah, he’s late 20s. He doesn’t have kids. Yeah, grinding.
Adam Besvinick (01:06:17):
Some of the stuff is a young person’s game.
Brian Bell (01:06:20):
Yes. This has been an awesome conversation. I learned a ton and really enjoyed it. Thanks for coming on.
Brian Bell (01:06:25):
Yeah, thanks for having me.
Adam Besvinick (01:06:26):
This is great.
