Ascent Podcast Ep. 4 – Charlie O’Donnell, Founder @ Brooklyn Bridge Ventures

Brooklyn Boy Represents

The Ascent podcast host/MC and author of “Humor That Works” (a book that looks into ways that increases team productivity in the workplace), Andrew Tarvin sits down to interview Charlie O’Donnell. Charlie is a born-and-bred New Yorker with 15+ years of experience working in the venture capital sector. He is the sole partner and founder at Brooklyn Bridge Ventures.

With origins in a Wall Street mail room, Charlie worked his way up the ladder. After a job in the mail room, he obtained a high school internship in General Motors. This would later become his first job in the private equity and venture capital group. These early experiences in the venture capital industry made him what he is today, someone featured more than five times in Business Insider’s 100 Most Influential People in NY.

Betting on the First Timers

Charlie built Brooklyn Bridge Ventures by quite literally going after the people other venture capitalists wouldn’t normally go for. In this interview he talks about how his early work shaped him and how his experiences defined his mentality and approach to what he does. Brooklyn Bridge Ventures is known for investing mostly into first time founders, or companies that are in what’s known as the “pre-seed” stage. In a world where most venture capitalist firms usually go for startups with seasoned founders, he has made a good living doing exactly the opposite.

Now if you think that he’s not a savvy investor for choosing to invest in companies in the startup or “pre-seed” stage, let me ask you this: Have you ever heard of a social media platform called Twitter? If you have, just know that he’s been credited as an influence to early Twitter investors. Charlie is known for identifying important companies and knowing who to bet on early. You’ll get insider access to important insight and learn what drives his decisions.

Being able to identify potential in companies in such early stages takes strength. That’s probably the type of strength that’s also led him to do four Ironman marathons, four marathons, and fund a kayaking program in Brooklyn Bridge Park. Charlie is an all around amazing person, you don’t want to miss this episode!

Time Stamps:

00:01= Intro/ Welcome
03:01= Rapid Fire Questions
10:27= First way to make money/ Early hustle
12:37= First job experience
17:57= Venture Capitalist focused on helping startups
23:32= Starting Brooklyn Bridge Venture/ Motivation for setting up his own thing in New York
29:05= Importance of being accessible/Being on the radar
33:35= Experiences with the companies he’s worked with/ Anecdotes/ Impact of working with startups/ Importance of a thoughtful process and having everyone on the same page
37:20= Process of choosing investments/What to look for when making a decision on who to invest in/ When and why to say no or yes
42:20= Finding the right fit/ reasonability of the plan
45:03= Educating people and sharing the message
47:48= Morning routine
49:45= Engaging and encouraging through social media with your significant other
52:21= Work/life balance/ Communication is key
55:25= Where and how to get in touch with Charlie
58:23= Outro

Andrew Tarvin [00:00:00] Hello, everyone, and welcome to Today, Friday, December 18th, as we are getting started and we are here for the Ascent Live podcast, a live video conversation where we get to know the human behind some of the top leaders in tech. My name is Andrew Tarvin and I will be your host and emcee for today. And I’m particularly excited because Roomi talking to Charlie O’Donnell, who is the founder and general partner at Brooklyn Bridge Ventures. But before we get into that, just a couple of quick announcements for those of you joining us today in Remo. This is the remote platform as we’re going through. If you have questions, you are welcome to share those in the Q&A functionality over to the right. And we’ll see those as we go through the interview if you are listening in the traditional sense of a normal podcast. Well, there is no Q&A over to the right, but you can always shoot us an email or a message. And, of course, don’t forget to like and subscriber rate and subscribe to the podcast on your favorite listening app. But I’m excited for today’s conversation with Charlie, who is the sole partner and founder at Brooklyn Bridge Ventures, because one fascinating work that the group does, a Brooklyn Bridge Ventures has, has made over 70 investments since it was founded, making it one of the most active funds investing in precedent’s ground in the city. That’s New York City. And prior to Brooklyn Bridge ventures, Charlie was a principal at First Round Capital and he was the first analyst hired at Union Square Ventures. So this is clearly someone who knows his stuff. He’s been named to business insiders, one hundred most influential people in New York Tech, many, many times one of 12 people to be named that way five or more times. But not only that, as a human, he competes in triathlons, he bikes to work, and he founded the Brooklyn Bridge Park Boat House, which is a free kayaking program on the East River, which is pretty sweet as well. So I’m really excited for our conversation today. So please join me in welcoming to your screens or to your ears or to your eyes. Charlie O’Donnell.

Charlie O’Donnell [00:02:13] Hey there. Thanks for having me.

Andrew Tarvin [00:02:14] Absolutely. How are you doing today, Charlie? Feeling good?

Charlie O’Donnell [00:02:18] Pretty good. Even though the biking to work has decreased a little bit in the last year. But I still make time to go around in circles in the park.

Andrew Tarvin [00:02:27] OK. I was going to ask about that. Do you walk outside, ride around in circles a little bit, come back a little bit. That’s pretty much it. Yeah, I like it. Right. Actually, I’ve read some research that there’s value in creating a commute kind of like that, even if you don’t physically, just as a way to kind of physically separate work and life. And in some regard and we’ll chat a little bit about kind of how you’re adapting to the current environment coming up. But before we do, we like to get to know the human behind the person. So we’ve got to we’re going to start with a quick rapid fire round where you can basically just answer with one word or two word responses. Are you ready to try the Rapid Fire? Yes, sure. Go ahead. Let’s see. So starting first, are you a morning person or a night owl?

Charlie O’Donnell [00:03:09] Night ish.

Andrew Tarvin [00:03:12] Ish, OK? I like the like the had to think about it, but I like the the intent behind that Apple or Android?

Charlie O’Donnell [00:03:19] Apple.

Andrew Tarvin [00:03:20] OK, introvert or extrovert?

Charlie O’Donnell [00:03:22] Extrovert.

Andrew Tarvin [00:03:22] When you were a kid, what did you want to grow up to become?

Charlie O’Donnell [00:03:29] You know, I think the first thing I ever said was lawyer, but that was probably because of like TV lawyers and trial and all of that sort of stuff growing up in New York. Wall Street looms large, so something to do with the stock market. But I don’t think I had a really good idea what that meant until sort of late high school.

Andrew Tarvin [00:03:53] OK, it’s a lawyer, maybe stock market art and obviously influenced by our perceptions of that. A lot of times, media of like a lawyer, like being a lawyer, trial lawyer like looks amazing. It’s 12 Angry Men type as a focus as opposed to. Well, actually, there’s a lot of research that you’re doing a lot of time in email and meetings and things like current favorite hobby.

Charlie O’Donnell [00:04:18] Ice hockey. Actually, I’m an ice hockey goalie.

Andrew Tarvin [00:04:22] OK? Very nice. And are you currently is ice hockey? I mean, you’re all wearing a kind of mask anyway, I guess. Is that something that you can play during the pandemic?

Charlie O’Donnell [00:04:31] Yeah. So luckily enough, there’s an outdoor rink not too far from my house. And so I I’m not playing indoors this year, but outdoor season just started and yeah, I’m pretty well messed up.

Andrew Tarvin [00:04:46] OK. And is it. I’ve never I played soccer growing up and was always terrified to play as goalie because I’m like I don’t want people intentionally like shooting things at me. Is it painful to get hit by a puck?

Charlie O’Donnell [00:04:59] No, it’s not your the amount of padding is is almost comical. And I think one of the reasons I like playing goalie is, as I’ve learned in my professional career, like I’m a solo general partner. I’m I kind of like doing my own thing. Right. Everybody else is sort of out there skating around teamwork, all of this sort of stuff. And I’m in my little crease by myself. I’m very content there. I hope the guys in front of me do their job, but if not, I can sort of handle the situation on my own. So I’m an individual contributor.

Andrew Tarvin [00:05:34] OK, I like that I’ve ever thought about that. The metaphor of hockey and being a goal in that way. But it actually makes a lot of sense. What is a TV series you’re currently watching or recently finished, if any?

Charlie O’Donnell [00:05:48] Yeah, we’re hurrying to finish watching the West Wing because Netflix is actually taking it off as of like Christmas. So we we only have a few days left to go. But we over the past sort of a couple of years, I’ve taken some comfort in watching presidential things on TV to imagine what actual professionals might look like. And so it’s been nice to sort of pretend that Martin Sheen was actually the president for a little while. But that’s and it’s a really, really terrific series and really, really great acting.

Andrew Tarvin [00:06:28] Oh. It’s incredibly well done. And yeah, you can you can you can you imagine a better president than President Bartlet? I mean, maybe day from the movie President Movie Day.

Charlie O’Donnell [00:06:38] Yeah, for sure. For sure.

Andrew Tarvin [00:06:39] And very cool. And who is a famous person who you admire?

Charlie O’Donnell [00:06:45] The famous person that I admire. I’m not a big celebrity person, to be honest. Yeah, I’m going to I’ll probably take a pass on that I think I need more of my admiration comes in just sort of some of the people I know I am friends with a a a marathoner competes in a with a with a wheelchair and, you know, just have a number of people in my life that I just think are super admirable, but they’re not particularly famous. So, yeah.

Andrew Tarvin [00:07:31] And they absolutely don’t need to be. I love that as a as a context. Right. There’s probably certain traits about that person or those people that you do admire. And last question, you can certainly answer this in a longer than one word answer, but as a kind of I get to know you. What’s the story of your name? Right. Are you named after someone? Does it name that it means something? Is it just kind of random? They have a story behind that. Charlie O’Donnell.

Charlie O’Donnell [00:07:56] Yeah, actually, my dad’s name and my grandfather’s name, which my middle initial is E! And so people sort of find me on Twitter and various other social things that CEO and I see, and they always think it has something to do with with business, but that’s actually just my initials. The funny thing, though, is that I’m not a junior. We both have and I’m the third son, so I’m sort of like there’s a big age gap between us, too. So it was sort of like my dad had conceded the fact that he wasn’t going to get a kid named after him and then like 16 years later, finally, finally got one. So I’m the third Charles, but none of us are first or second or third And not first or second.

Andrew Tarvin [00:08:46] Yeah. OK, I was I was wondering about that. Yeah. Because your social media is in NYC for a lot of things and it’s like, oh yeah. This is really I mean it kind of makes sense for someone that’s in the DC world a little bit maybe to have that. So I just thought it was a brand thing. But I love that it’s the initials there as well. And I’m curious, how do you like being like is it confusing with family to be are you all. Charlie, do some of them go by Charles or Chuck or things like that? How does how does that work in terms of the the family naming structure?

Charlie O’Donnell [00:09:16] Definitely no. Chuck and I was sort of ambivalent as to whether it was like Charles or Charlie until my first job out of school, I worked for a Charles who was very strictly Charles. And so that meant that I was Charlie. And it just sort of rolls off the tongue a little better between first and last name. So although my my mom and dad will just shorten it to Charlie sometimes when I was a little kid, sometimes it was Charl Charl, which I’m not so sure why that’s easier or.

Andrew Tarvin [00:09:55] More syllables?

Charlie O’Donnell [00:09:57] Yeah, that’s not something I would necessarily recommend that founders refer to me in a pinch. Yeah, Charlie’s fine.

Andrew Tarvin [00:10:05] Yeah. So if you’re listening to this and thinking later that you want to pitch, make sure you’re really paying attention to the name. Don’t just like casually like kind of hear that off of glance me like I’m totally going to call Charl-charl like. And so as we started to transition into kind of some of the work that you do, we have a lot of entrepreneurs and and people who listen. I’m curious, what was the first way that you made money? Was it out of school and into a kind of more traditional job? Was it something earlier on? Do you remember that that first way you got your first either paycheck or stipend or your money or whatever it was?

Charlie O’Donnell [00:10:42] The first deposit I ever made, the bank account was in the second grade and it was one hundred and eleven dollars of communion money. And so that was like I just remember we used to get like the physical bank book, like you’d go in and type in the book, like this is your statement and all that sort of stuff. For whatever reason, that one hundred eleven dollars like really kind of sticks in my mind. I did get sort of a small allowance as a kid, but my first job, my older brother actually helped get me a job in a mailroom on Wall Street for a brokerage firm that he was like a sort of a senior VP at. And so three days a week over the summer, probably between sophomore and junior year, I worked in the small room and just stamping stuff in delivering stuff. But it was cool because I got to hop on the subway down to Wall Street to work with all these sort of professional people. And it you know, it beat what all of my other teenage friends were doing, just working in like retail or food and all that sort of stuff, which were like way, way more work, way harder for less pay. And so I feel like I really, really lucked out in my my first job.

Andrew Tarvin [00:12:23] And a lot of times tough hours in that regard. And so in the mailroom, did you learn things that then kind of altered or changed what you wanted to do from seeing that we’re like our Wall Street was great? Or like, did you see me? Like, actually, I want to go in a different direction. Does that influence kind of what you did later anyway in any way?

Charlie O’Donnell [00:12:43] No, I won’t say that it did, but I did my second job after that. I got an internship. My high school actually had this phenomenal program. I went to to Regis High School, which is a private high school in Uptown and here in New York. And they had this internship program where they basically kicked you out in your third semester of senior year because you’d already, like, applied to your colleges and stuff like that. And so the community service project or something like that. But I wound up working sort of four days a week full time. And then the fifth day was like an internship seminar day at the General Motors pension fund, which was located on fifty ninth and fifth in the General Motors building, otherwise known as the building behind the Apple store or the park. And it was amazing. I mean, it was, you know, so this is like nineteen ninety seven. And one of the first things they asked me was whether or not I learned how to use Excel and I had had a computer in the house for about ten years. My dad came home with a computer when it was like eight. And so I was like familiar with spreadsheets and was doing most of my school homework assignments on the computer and stuff like that. And my other sort of internship buddy, this other kid that I went to school with, like he didn’t have a computer in the house at the time, which is like crazy right now. And so he got all the, like, photocopying and filing. And I got these like really interesting modeling spreadsheets, like whatever somebody was sort of willing to teach me how to do that. They didn’t want to do any more. And the General Motors pension funds are pretty sophisticated. Asset manager. I mean, they’re managing like over two hundred billion dollars in assets across a whole bunch of different assets. And it it really gave me sort of a bird’s eye view of what is a trading room look like. What what do people who pick stocks do private equity and real estate and stuff. So I actually wound up staying eight years. I, I interned as an intern that entire time.

Andrew Tarvin [00:14:56] I imagine.

Charlie O’Donnell [00:14:57] No more years as an intern. And then they hired me full time in the Private Equity and Venture Capital Group. So like the two sort of amazing things, is it like one, I actually retired from GM when I left, technically because I had four years of full time service and then they added up all my internship days. So technically, I vested into the General Motors pension fund, which is no longer a thing. You just get it for a week. But when I left, they said, well, what would you like to do with your retirement money? And here I am like twenty five. And I was like, well, you have a choice. You can either get eleven dollars a month for the rest of your life and sixty two dollars a month starting at age sixty five. Five or seven thousand dollars now. Twenty five years. I was like, thanks, I think I’ll take the seven thousand dollars. It’s just like just totally unexpected check. And that’s what they had to from an actuarial standpoint, like pay you out to to to buy you out of the pension fund. So, yeah, it was was a great it was a fantastic internship. I bounced around to a bunch of different groups and it gave me a really fantastic sense of like all of the different areas of finance. And what I really learned was that like. I am not one for a really fast paced environment, and I I really I liked the people who worked in the trading room, but I didn’t like making split second decisions. I liked sort of long term thinking and being able to be very academic about things, manage stuff on a portfolio level. And it really affected me, too, because I’m I’m more of a portfolio thinker than I am a deal person, which I think is a little different than a lot of people. Inventure venture like I like to think about. If I made the similar profile risk that 30 times, how would my early stage portfolio look versus like, is this the one and is this founder the one, which is, I think, more the narrative in early stage.

Andrew Tarvin [00:17:09] Yeah, which one, I think it’s refreshing to hear a little bit, because I think for whatever reason, maybe because of media or maybe because of survivorship bias or whatever, a lot of times, like it’s like, no, you got to be the one that wants to be in the fast paced environment is like almost shoot from the hip type thing or whatever. So in some ways it is refreshing to hear that of like, no, there’s still a role and a way that you can play the skill set if that’s what you prefer. That’s a longer term picture and bigger picture kind of thinking. I do want to get to kind of this idea around D.C., but I’m curious before jumping into that, why why that direction in terms of DC as opposed to because I know you have some experience as a founder. You’ve had some experience in big companies like a place like GM and and things like that. What was it about being someone who’s who’s helping these startups do things as opposed to being that CEO yourself, etc.? I mean, in some ways you are. As for Brooklyn Bridge ventures, but versus kind of taking a product or service and building it out, what was it about DC that drew you in?

Charlie O’Donnell [00:18:16] Yeah, sure. I can’t take credit for picking private markets. That is just happens to be the thing when like when I graduated and I was going around GM and all the different asset classes just to see who had an opening that happened to have the opening, it is like I can’t say there’s any more thought that went into it in terms of different asset classes. So that basically put me in the group that did both venture capital investments, which was obviously mostly tech and biotech buyouts. So larger companies taking private sort of barbarians at the gate type stuff. That actually gave me, I think, a really good insight into what mature businesses and lots of different markets act like. So, for example. Team that did the leveraged buyout of AMF, the Boeing Company, and so, like I know more about the economics of Boeing than most. So I would just we would always be in sort of random markets like that, like companies that made like you never really think about that. But like there’s a company that like makes ice. And, you know, it was part of like some leveraged buyout somewhere. So that give me a good perspective on the market overall in the private markets, choosing between LBOs and Matt’s dad and distressed Inventure, I think was a combination of two things. One, a little bit timing, right. So I went to college in the late 90s. And so if you were at all interested in investing or technically inclined, you know, like I had a little brokerage account when I was in college, you know, took what that compounded communion money basically, and threw it into AOL and Yahoo! And all the sort of stuff. Right. Which at first made me think I was very smart. And then I realized I wasn’t very smart. Same thing that everybody else felt like during that period of time. And so I was like inclined to be interested in tech and tech investing. And I think the personalities of the managers really resonated with me. I mean, to people that really stuck out where Brad Feld and Roger McNamee, GM had been invested in Brad’s fund for for a long time. And so I probably first met Brad in like two thousand and three, which is probably right around the same time it first encountered Roger. And they’ve just been tech investors forever. And they just were really cool people. They were just super enthusiastic. I mean, Roger would show up with like eight devices, like clipped to his belt like some kind of like Batman utility belt of like the latest phone or Palm Pilot or whatever people were kind of using at the time. And they were enthusiastic and fascinated by cutting edge technology. And it was it was kind of infectious, to be honest, compared to the bad guys would come in and be like, here’s a company we never in an industry we don’t really care about. Here’s this like frozen vegetable company. And we think if we bought it at this valuation, levered it up with being able to, like, take money out of it, and those guys were just, like, really enthusiastic about making money. And, you know, no disrespect, but I just wasn’t that wasn’t my calling. Now, in hindsight. A lot of those were very interesting people and very nice people, some of them not as nice, I wish I would have stayed in touch with some of those guys a little more because it would have made great limited partners from my phone. So I didn’t really network them. I didn’t want to do they were doing. But some of them own professional sports franchises now. So they they would have been good networking partners.

Andrew Tarvin [00:22:23] So and but I think from that, I think two things that stand out to me kind of listening to that is is one, yes. Sometimes it’s just kind of circumstance in terms of what major you end up picking or what job you get at school is the one that happens to be where the opening was or whatever, but also just how how valuable finding cool people or people that you resonate with can have an impact on your career because you’re like, well, these are interesting people. I want to learn from them. And I don’t think that’s I don’t think it’s like a bad thing. I think it’s a thing for people to keep in mind. And as you go through as you get older, you can start to be more intentional about like based on these past experience. Now, I can say this is what I really want to do, but especially for the people who are listening, who are still in school or recently graduated. Sometimes a starting point isn’t like, oh, knowing what that 50 year future looks like, but instead being like, what are the opportunities right now in front of me that are exciting? And then knowing that those may evolve into something else completely and the future of kind of what you’re sharing there. And so, as you say, you go through some of these experiences and then what was the desire for starting a VC firm or the Brooklyn Bridge venture specifically in Brooklyn?

Charlie O’Donnell [00:23:41] Yes, so I got to work for two really fantastic firms, so I was the first analyst at Union Square and I was the first principal hire in full time in New York for first round capital and two really phenomenal organizations. And the really difficult thing about venture is that the goal is to become a partner somewhere, both for economic reasons and for autonomy reasons, to be able to lead deals. Partner positions don’t grow on trees at at Union Square Ventures. I joined when I was like sort of twenty five. The two partners had vastly many more years of experience than I did. And so like a partner was not the logical next step for me to be there. And then the first round capital, they had four partners. It was like one hundred. Thirty million dollar fund. It wasn’t like an NEA where they’re managing three billion dollars and they have twenty four partners and it’s continuously growing and it’s more like an asset manager. And so there’s just no room at the end. And so you you get what experience you have, but you just have to find the opening and the fit. And a lot of those folks like Brad and Fred and like Josh and Howard. The answer is in creating your own firm. Now, today, that is seems like everybody has their own firm today when the market is totally exploded. But it is a little less of a thing at the time when I started a bridge, I think, for me. You know, I was sort of the same me in Brooklyn Bridge ventures that I was at first round, I mean, maybe possibly a little earlier stage when I could sort of take less risk, not have to get three votes to do a deal and on my own sword. But, you know, I had this. Way of going about the market of being like out and about and being somebody that, like people knew and tried to be accessible, and so all of that kind of went into what I wanted the firm to be in terms of the branding and the location. I grew up in Brooklyn. I’ve lived my entire life within the five boroughs of New York City, including for college. It just struck me as a natural, you know, brand affiliation for me and the Brooklyn Bridge between spending so much time in Brooklyn Bridge Park and kayaked under that bridge so many times. I’ve biked over it. I’ve driven over it. I’ve run over it. And so that part was really a natural relocation thing for me, was like convenience because I lived in Brooklyn and that like, if you’re going to start your own firm, why add on extra convenience to make a commute? But really, if you look at where the entrepreneurial population in New York City lives, just by population number, there are more founders who live in Brooklyn than live in Manhattan. And that’s not put in place like Brooklyn is a creative place and all this other stuff. But like Brooklyn is almost twice the size population wise as right. So if nothing else, there are as more people living in Brooklyn and in fact, like when Brooklyn and Manhattan, which was sort of New York City proper before they merged, was first sort of competing neck and neck as different cities. Everybody thought the Brooklyn was going to be the larger city because the idea of building up was like not a thing at the time. And so it just made more sense, like, oh, Brooklyn is bigger by landmass. So clearly it will be the larger city. And actually it turned out right like there are more people live in Brooklyn than live in Manhattan. So that’s sort of where it kind of came from. But it’s like there’s a lot of companies over here.

Andrew Tarvin [00:28:06] And I love the I love the balance of those two things. I think in one, we have entrepreneurs that might be at that stage of thinking about naming or thinking about folks or things like that. And I think when you can tell the story a little bit about it, there’s there’s a balance of the convenience. Right, in terms of why. But then also there’s the logic of additional people.

Charlie O’Donnell [00:28:25] But then it is also a story you can connect to it like, yes, this is a bridge that I’ve seen my entire life that you’ve said that that you either kayaked under Bykov or whatever, that this story, I think a lot of times is what can make something even a little bit more meaningful rather than picking guess ABC Ventures or whatever. There’s there’s this connection and and it becomes more authentically you as part of this. And one of the things I know you’ve talked about, you even mentioned it there, is that you want to be more accessible to people. And part of that is especially for all the people in Brooklyn, rather than being in, I’m going to be in this high rise in Manhattan that you got to come in and see me and all that kind of stuff. Why why is being accessible either important to you or a strategy for you is at one or the other. But why is that something that you’ve made the choice to do?

Charlie O’Donnell [00:29:15] Yeah, I think when I think about the sort of next sort of 50 most important companies to be built in New York, my bet and I think if you sort of hard to argue against, is that most of the founders of those companies are just not on people’s radars today. Yes, sure. Some of those people will be the current founders. Right. Like will the founding. Go off and build another company, like, sure, and they won’t have to raise a seed round the next one because they made more than enough money launching their company. And but the reality of most of those companies is that it’s probably an iPhone developer at. Companies that is thinking about the next big thing, right, it’s probably that the head of marketing for some for Shutterstock or whatever and not. Marketing, it might be a junior marketing person who experiences a problem, maybe either personally or professionally, that has an idea that person is not on the board. They probably don’t know the voices of that company. They might not even know the founder on a first name basis. And some of these companies that have become very big. Right. And so where do they go and how do they connect? And the reality is that, you know, maybe they’re not. Mitt Entrepreneurial Network, or they didn’t go to Harvard or what have you, and where do they go to get early feedback, what sort of standing in their way? And I’ve always just felt like. The warm intro, the only contact me if we know somebody in common and all that sort of stuff is just sort of a. It’s an unnecessary filter that, frankly, doesn’t add value. It’s kind of funny, actually, somebody. Cold emailed a founder that I backed to try and convince that founder to introduce them to me. Just just email me my emails on the air. That would be like, why go through what I call email this person to get to you or what it’s like, right. If you successfully gotten coffee with somebody that I know, what makes that a good filter for venture capital? Right. And it’s like the founders that I backed are not VC’s. So like, why do I trust their filter? I mean, they might be good at hiring. They might know their space. And I’m happy to say I’m thrilled when people back to send me introductions. But it’s not a filtering mechanism by any stretch of the imagination. So I would just as soon rather get stuff direct them when I realize, too, is like. Everyone’s network kind of looks like themselves, right? Like, I know more straight, bald white guys with beards than other VXI, and I don’t necessarily want my deal flow to look like that. Right. And if you’re a founder who comes out of the BCU network or something like that, we might not know that many people in common. And so why should that be a barrier to you pitching?

Andrew Tarvin [00:32:52] Yeah, well, and I love that kind of approach. And it expands kind of what you’re looking for and giving some of those opportunities maybe to, like you said, some of the people who aren’t necessarily in those programs that have more of that visibility by default, either because they’re at a big Ivy League school or because they were they already had success at at another place. I love that approach. So then what do you look for? Because you you’ve been a part of some great deals, both with Brooklyn Bridge ventures, early investments in places like the Wing Canary, Hungary, for example, Hill Clubhouse. Imagine going on and on you also people talk about your role that you have played in early investments for places like Twitter and Foursquare and Moate and group me right. So one, I guess, quick question. Is there a brand that just sticks out that you just absolutely love or is that like picking your favorite child? Because the reason why I say that is like Apple Hill is some of the best ice cream on the planet. So I think that’s amazing that you’ve done that. But like, is there anything that sticks out to like, I’ve always really appreciated this brand of the way that people have used it or created it or the people that you work with their.

Charlie O’Donnell [00:33:59] Yeah, so I’m not going to pick my favorite kid because that that will create a lot of friction sort of internally. But I tell you, you know, I. I actually was just sitting down with one of my founders this week, and they went through this branding exercise that they had done internally and what really struck me most medical care switch, and they are in the home care space just helping agencies that help with home health aides to sort of manage their their staff and all that sort of stuff. So you wouldn’t necessarily think of like that in the sort of great brand and the sort of thing or whatever. But they were walking through an exercise that they had done, which was such a thoughtful review of their brand and messaging. And they it was such a process. And I think a lot of times people think of brand as like. Just design, right, like, I mean, our website look good. And what struck me about their process was. They looked out in the market and they said, what voice do we want to have? How do we want to speak to our customers? Right. What is everybody else in the market say about their value proposition proposition? What do we want to say and how is it different? Like, it was just such a methodical process that I think I even went as far as like I asked the founder if I could just record the work that they had done. And I sent it to some of my internal portfolio companies because I really think that brand, the best brands, are a result of a thoughtful process. Now, some time founders develop them with a thoughtful process in their own head, and they don’t realize that they they’ve gone through a process. But I think it’s really important for your team so that everybody can be on the same page and say, OK, like this is how we want to talk to our customers. This is how we want to talk to the market. So it empowers that junior PR person to answer a reporter question, because everybody knows how we talk about ourselves. Everybody knows the relationship we want to have with our customers. And so I appreciate everybody that appreciate anybody that goes through a strong collaborative process to get everybody on the same page about their brand.

Andrew Tarvin [00:36:41] Which I think makes a lot of sense. Right. It is more than, like you said, just the logos that you choose or the typeface or the the font colors and things like that from our side. That’s why we encourage encourage brands to have humor style guide in addition to their brands. I like it’s part of it. And what’s the like you’re saying, the voice of it so that everyone is on the same page of what is our sense of humor, what is our style for answering these questions? What is our bigger picture goal? And that certainly comes from spent time at Procter and Gamble where brand management is much bigger than just the brand assets that are created. So, so thoughtfulness seems to be kind of one of those criteria. What else are you looking for? What do you have a rubric that you go through in terms of looking at companies? Is that more of a gut feel? Is it like got a really like the founders? It it’s got to be like super profitable and can expect a turnaround. Like what from your perspective? What what’s the criteria you look at?

Charlie O’Donnell [00:37:36] I really appreciate that you stuck to that question, despite my meandering first part of that answer and you didn’t let me get away with avoiding it. I feel like there’s a journalism background in there somewhere. No, I think the process that I go through is more about elimination than it is selection. The reality is there’s about two thousand deals that show up in my inbox over the course of the year. I think about one hundred and fifty ish first time pitch meetings. I do like real work on about 30 and narrow down to like eight to 10 deals that I actually wound up doing. And so most of what I’m doing is not saying, yes, it’s is actually saying no. And so I think the biggest questions that is most relevant for a founder is like, why do I say no? And then what? I don’t think my portfolio really likes to think of itself as like leftovers, but kind of what they are like, in a sense, what exactly they’ve survived the process and the things that eliminate companies are like I mean, market size is a big one. I mean, if you just if you can’t get big enough, there just aren’t enough customers if you can’t make enough money from those customers. I mean, that’s that’s just sort of an easy one. And there are a lot of really great projects whose terminal value is like. Five to 30 million dollars, right, and then they should be appropriately financed, maybe just with a handful of angels, they should be tuck in acquisitions to some larger things. They just don’t have a very large scope to them. And and those could be fantastic outcomes for founders. I mean, I have I have investors of mine who have bootstrapped and sold to companies one for like eight million dollars and the other were like four thirty. And now they’re investing in venture capital firms. So you can make a lot of money, bootstrapping companies to quote unquote, small exits. You want one hundred percent of them, I think. Founder, market fair or founder problem fit is a is a big one, like are you do you possess the right skill set for this particular problem? I just I just passed on a company yesterday who pitched me. I thought the founder was knowledgeable about the problem, but I thought the problem really required a lot of insight into messaging and marketing and to stand out where the challenge was like standing out and finding your customer. And that DNA just wasn’t on the team like it was someone who was just sort of a category expert, but not a marketer, not a UX or design or brand kind of person. Not somebody is going to the execution was like pretty product. Like, I just there’s no one I can sort of bet on here to meet the challenge of your what you’re doing. The the counter of that is when I was at first round capital, I backed a company called SinglePlatform and it was started by the former VP of sales of similar. And so the local marketing space, the challenge is how do you call up a pizzeria and get them to buy Tack Rite Aid? And that that’s a very different sales process than calling up the CEO of Morgan Stanley to go VITAC. Well, who knows how to do that and run that sales team? But the former ten year VP sells it seamless. They have that same company, Yorkston Yelp and all of that sort of stuff. Right. So I would back him to do that kind of company, whereas I wouldn’t back him to do an educational kids. I mean, you got to sort of match that and then I think.

Andrew Tarvin [00:41:47] Well, so just real quickly on those two things, I think there’s great insight in both of them. So one of our gaps fit, etc.. In even to your point, though, is to say that that doesn’t mean that it’s not a good idea or viable. It just might be one, you’re not the right book for them. And or maybe the traditional VC, right. Might not root might not be the right fit. So I love that in terms of being an entrepreneur and thinking like, OK, is is this type of the type of backing that I actually need based on what I’m doing. So I think great insight there. And then this this fit piece I think is really interesting too, because a lot of times I think the stereotype is like, yeah, you’ve got to really believe in the team and it’s just got to be a really good team. But I haven’t necessarily heard this articulation of, like, it’s got to be a good team for that problem. Right. That like, there’s certain things where it is like, OK, I would take this founder in this scenario because of this, but it could be the exact same founder. But in this scenario, might not because of that that fit. So I love those two distinctions just to kind of clarify that. And so then this third piece you’re starting to speak on.

Charlie O’Donnell [00:42:49] Yeah, the third piece, I think, is just reasonability of the plan. And so just to be able to say this is something that this could be a flexible conversation, sort of in the meeting, somebody might come in and say, in fact, I’m literally just closing on a deal now where the founder originally came in and says, I think I need five hundred K. And the reality is just five hundred didn’t really get them anywhere like it didn’t get them to like a significantly different kind of company and a different sort of level of progress, sort of a B2B company and five hundred K probably like bought them some engineers and bought them some product expansion but didn’t really establish a sort of real sales and marketing effort. And so like now it’s kind of an engineering focus founder. I was pretty certain that they could build this stuff. So we didn’t understand, like, why raise five hundred to build things that I already believe you could build if you had the money. The real question on your team is, can you sell this? And I’m willing to take that risk. But like that risk is still going to exist at the end of your five hundred K, and you’re going to be just sort of in the same spot. You are now being an engineering focused team with some product and not a lot of sales marketing traction. So I push them to to raise a million and a half, which we are just wrapping up now. And by the time they reach the end of this million and a half will be a company that’s doing sort of two hundred came month in revenue. And that’s a definitively different story than where they are now.

Andrew Tarvin [00:44:36] Yeah, yeah. I love that. So three great kind of criteria for people to to think about, which I think gives a lot of insight for for people. And and so as we start to to wrap up, one of the things I do want to just quickly talk about is. So you have a great blog. This is going to be big, you’ve got a newsletter that you send out, you’ve spoken at places like South by Southwest and TechCrunch, Disrupt, et cetera. What? See what? See you just like speaking. What’s the like? Is it a business strategy to get out there and vocalize? Because I feel like some people can be like, OK, I’m just going to focus on the work. Why do you spend that additional time to to educate and to share messaging and insight to a broader group that’s not just pay the people that you’ve brought into the fold under the v.C.

Charlie O’Donnell [00:45:25] Yeah, so I’m a generalist investor, right, so I am not going to go sort of neck deep in a particular area and go house to house and sort of figure out like, who are all the people that I need to know and the information security area, who are all people who can refer me to the next big founder in this space? And, you know, for some people that works for them and they get to know all the trends and they sort of know what they’re looking for before it shows up at their door. And that’s how they find stuff as a generalist investor. And at the stage that I’m doing right. The companies that I’m investing in, they’re not on Krunch base. They’re not on pitch book. They’re not findable. Right. There’s somebody who’s going to watch this, who hasn’t quit their job yet, who just has a little side project going. There’s 20 users on it. That is a completely unfindable company. So I need my story to find that and to be findable so that when they go poking around the market, they’re like, hey, who does like kind of ridiculously early stuff in New York and is willing to take a lead position and put down a term sheet that we don’t have to throw too many rocks before you run into me, know? And then there’s a conversion thing, right? You listen to the podcast and you think like, well, maybe I could work with that guy or maybe maybe I want to pitch him or whatever. And so it sort of helps the conversion, I think, as well. So you kind of know what you’re getting when you show up at a meeting with me.

Andrew Tarvin [00:47:02] Which I think is fantastic. I think within within sales there is also kind of that idea of people oftentimes buy from the first person to provide them value. So the fact that you are giving and you’re giving insight, if people resonate with the way that you share that message, then they’re like, oh, well, maybe I want to learn a little bit more. I like the way that this person approaches this idea here. Hey, I have the clear criteria of some of the things that they’re looking at, and so I might have a good conversation with them. So and at the same time, you get to do that while also serving a bunch of people. So, you know, as we as I mentioned, as we start to wrap up, one of the questions that we like to ask each of our guests is about their morning routine, because some people are super and have a very clear thing that they do every single day. Some people just kind of wake up, some curious in 60 seconds or less. What’s your morning routine look like?

Charlie O’Donnell [00:47:51] My morning routine lately has started out with hanging upside down for a couple of minutes. It’s just I just got these little clips that attached to a pull up bar and I’m in my forties now and my back isn’t what it used to be. So that that has been a game changer. I do try an exercise in the morning. Either I’ll ride my bike or I do this workout called Convery, which is invented by a somebody who’s formerly incarcerated. So it’s a workout that essentially do in a small space, doesn’t require any weights or anything like that. I try to eat three square meals a day and a person I don’t know how these sort of intermittent fasting people go hours and hours. I would become very irritable if I didn’t eat on a regular basis. And then my wife and I have sort of started taking to, you know, at least during the pandemic when we’re not going anywhere early morning walks, just kind of out there and start today and talking. And I think that’s important to like when you’re in a couple, when you’re living with somebody, it’s very easy to let the work sort of take up your whole day and not check in with each other. And I think that’s that’s really important, too. Yeah.

Andrew Tarvin [00:49:09] And you are certainly the first person that we’ve chatted with that started their day by hanging upside down. I love that. And it’s funny that you also bring up so you bring up your wife, because one of the segments that we also have on this show, sometimes we talk about is explain someone who you are following on social media. So I took a look at some of your social media and both on Twitter and Instagram, you give shout outs to what you say is your better. Half of all of your wife is also a singer who has a fantastic newsletter. And I’m curious, first of all, do you all follow each other on social media? Do you have to make sure that you like and comment on each other’s posts? Because you see you’re sitting right next to this incredible person as well. But do you actually engage through social media as well? Because I’m having I’m wondering that same question for me, my wife.

Charlie O’Donnell [00:50:01] Yeah, so we don’t sit next to each other all day. She’s in the other room, I’m in the bedroom, so we kind of have this like two office set up. One of us has Twitter notifications set up on the other one’s tweets. And so it is it is not her like I see where she tweets all the time and I make sure that I engage. She goes back to stuff not is not to not much into it, but I do try and engage. Actually, a lot of this sort of social media stuff is relatively new for her. She spent years as a creative director, mostly in fashion, and was trying to broaden her purview. And so being someone who’s been blogging for 17 years and newsletter for ten and all of that sort of stuff, I was sort of poking on that a little bit, getting her to put herself out there because she’s incredibly creative and super thoughtful. And the first response was that I don’t like to write, I’m not a good writer and all of the sort of stuff, but it none of this stuff is natural. I mean, it really is a function of practice and just like doing it. And so and now she’s just like I founders are pitching me and I notice they’re following her, not me, and all sorts of inbound opportunities from her newsletter and really, really developing a whole sort of persona on her own. And so and her newsletter is really good. And I read it and I think she’s I think she’s realized, too, is like it helps with thinking. Right. Writing is thinking. When she first started, she’s like, what am I going to write about? And now that she’s writing on a regular basis, she’s already two newsletter’s ahead in terms of generating new ideas. So I think it’s it’s not just work. It’s sort of it’s more like mind exercise to kind of have these conversations and put this stuff out there.

Andrew Tarvin [00:52:05] And I totally agree with that of like writing, especially as a as an engineer and as an introvert who like, you know, I think of emotions is data. Right. Which I think is in some ways good. But like by writing, it helps me to actually fully process some of these these thoughts. I love that. And so I’m curious from this perspective, because I think some some entrepreneur or some founder, some people listening may find themselves in a situation of how do the two of you balance both being and then these types of endeavors as kind of entrepreneurs yourselves are building and both being creative, especially in a pandemic working from home. You have it sounds like you’re in different rooms, but how do you balance that versus like, oh, the traditional kind of model of maybe someone’s going into work and has those set hours versus the more banal person where they might be working at. Who knows what our.

Charlie O’Donnell [00:52:52] Yeah, so I think communication’s really important, I think schedule management just even more so than just for professional reasons, for personal reasons, it is a huge thing. I mean, we you know, I got married at thirty nine and so I was both of us were sort of relatively independent people and used to managing our own schedules. And one of the things we realized is that like I’m a planner, particularly around, like I do a lot of races and triathlons and stuff like that. And so, you know, as I think about my triathlon schedule, I’m signing up six, nine months in advance and being like, oh, OK. Like, I know that next year I will be doing this race, this place. Right. She likes to kind of stroll into an open weekend and sort of figure out what’s around, what’s available and all that sort of stuff, when you put those two schedules together, what winds up happening is most of the writing on the calendar. And so we sort of we’re defaulting into having to do what I had planned because I was a planner and a kind of balance that we’re necessarily looking for. So, you know, I think we sort of meet each other in the middle right where she’s agreed to plan some things out ahead of time. If I sort of find something for us to do and I agreed to plan not to plan, basically sort of leave these blank spots in the schedule, we be like, we’re going to do something on Saturday and we’ll figure out what which is not very natural for me to do. And I think on a day to day basis, we’ve encountered the same thing. Like we tried to make it a point of coming together for for lunch. Part of that is because I do the cooking. So if we didn’t come together for lunch, she wouldn’t eat. So she needs me for that. At least I’m good for something. But meals are meals are important times for us to sort of come together. So we’re trying to stay on that that kind of schedule.

Andrew Tarvin [00:55:00] Now that that’s very helpful and very selfishly, just help give me some good insight between me and my wife, because she is also very much a planner, also a runner. Maybe there’s something about people doing marathons and things where they know that, hey, if I commit to this in six months, it actually also means that I’m running now every weekend or whatever, prepping to it or something. So a lot of great insight there with what my wife calls calendar science time, but the science of putting our calendars together. But, Charlie, thank you so much for joining us today. I love this balance of perspective, not only talking about from the VC perspective, but also the the life stuff and the managing of relationships, which I really appreciate. If people are interested, if they heard this in May, maybe I am that iPhone developer at this company, but I’ve got this idea or whatever. I’ve started to build it out and they want it to reach out or get in touch. What’s the best way for them to do that or to follow you, order to read the blog, etc.? What’s the what’s the best way to connect?

Charlie O’Donnell [00:55:56] Yeah, sure. So I’m I’m basically funding New York City area company. So that’s important. I believe location is important. I have this little calendar request tool on the Brooklyn Bridge DOT DC site. There’s also a link to it on my blog. This is going to be big. You go around and sort of findable across a number of of platforms. But I would say follow me on Twitter, sign up for the newsletter, but more so than just for me to build up followers, just to see who you’re getting when you wind up doing it. Some of the things I say may resonate, some may not. So I think it’s it’s helpful to understand, like, why you want to pitch me and that you actually do. And and. Yeah. And don’t hesitate to sort of reach out to early. I don’t I don’t take every meeting, I don’t take most meetings, but I do try and get back to people. And so sometimes a little too late in doing that. You can imagine my inbox given what I do for a living, but I’ll always try and respond with some kind of feedback. And a lot of times it’s I think people feel like they’re they’re helpful directional questions. We also do a ton of events at Brooklyn Bridge. We went on our website to one of the events, for example, is this event called Not a Pitch, which by the time January comes around, we’ll have a whole full slate of them. And I don’t even care if you came up with the idea that day would sort of jump into a big public group. The share like here’s a minute about what I’m doing and I give you like a minute back. And sometimes just it’s good early directional feedback like, hey, three people tried to do that two years ago when they all failed. You should just go check with these guys to see why they did. And maybe you never saw those companies because they never hit the light of day. But every week in New York already saw them. And if you’re pitching, that’s a disadvantage. Right? So that’s kind of like I’m trying to give early.

Andrew Tarvin [00:58:09] Yeah, well. And Action ball, so I love that. Also follow them in those places because he drops knowledge bombs just like he did throughout this entire podcast on social media.

Andrew Tarvin [00:58:18] You can find him at CEO NY and of course, through Google. So, Charlie, thank you so much for joining us today. As a reminder, there’s been another episode of the podcast brought to you by the conference, which you can learn more about at a dot com and as well as myself and humor that works, which you can find out more about at. It works, dotcom, we’ve got more great interviews and conversation with some great humans in the tech scene coming up, so be sure to subscribe and rate on your favorite podcast apps. And with all that being said, you all been great, I’m Andrew Tarvin and until next time.

Charlie O’Donnell [00:58:58] Thanks.

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