Deep Dive with Charlie O'Donnell

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This is a podcast episode titled, Deep Dive with Charlie O'Donnell. The summary for this episode is: <p>Today’s guest is Charlie O'Donnell, founder of Brooklyn Bridge Ventures. He and Matt are diving deep into the journey between entrepreneurship and venture capital. Charlie’s career has given him insight into a myriad of perspectives that influence his work with founders now, from his focus on team dynamics to his direct but empathetic approach to difficult conversations.</p><p>Later in the episode, Charlie and Matt talk through the current state of the market, the types of deals that are seeing success, and what’s next for Brooklyn Bridge Ventures. </p>
The evolution of Charlie's career
03:44 MIN
Making the decision to be an entrepreneur in the VC world
02:27 MIN
Taking learnings from being an LP to a GP
03:15 MIN
Apply past experience to being a startup fouder
01:45 MIN
Being direct
05:18 MIN
What 2023 looks like for investors
02:28 MIN
"You can't cut your way to success."
00:39 MIN
Brooklyn Bridge Ventures and what's next
06:43 MIN
Building a community in NYC
00:49 MIN
Lightning Round Questions
01:58 MIN

Intro: Welcome to The Daily Bolster. Each day, we welcome transformational executives to share their real world experiences and practical advice about scaling yourself, your team, and your business.

Matt Blumberg: Hi. Welcome to The Daily Bolster. I'm Matt Blumberg. I'm the co- founder and CEO of Bolster. With me today, going in deep with Charlie O'Donnell. Charlie has been an active member of the New York startup community for about 20 years. He currently runs Brooklyn Bridge Ventures and he has a reputation for being one of the most accessible, and I would say kind of best- known, early- stage investors in New York. I have had the pleasure of knowing Charlie for 18 of those years, something like that, so Charlie, thank you for joining the Daily Bolster.

Charlie O'Donnell: Excited to be here. Thanks for having me.

Matt Blumberg: Yeah. Why don't we start with you giving everyone a super quick career trajectory for you, because I'm not sure everyone knows about the first few steps, and I always think it's really interesting to see how someone's career evolves, especially in your business.

Charlie O'Donnell: Yeah. I'm one of the few folks that actually has come from the big institutional money that backs a lot of these venture capital firms. I started life at the General Motors pension fund, investing in mostly limited partnership investments in venture capital and private equity funds. Then Union Square Ventures pitched us. We decided that the fund was too small for the bite sizes that we normally do, although that was my opinion at the time. I pounded the table as hard as I could and didn't get us in. So I reached out to Fred. I said, " What does a junior analyst do?" He said, " You want to come and find out?" And that resulted in a little short of two year stint at Union Square Ventures as their first analyst. I jumped over to the startup side. I did a really brief stint as a product manager before trying to start my own company in 2007, around the time that you were not only an angel investor but my landlord. You were gracious enough to let us hang out in a roving set of empty desks from conference room to cubby to closet, wherever you could stick us, and we were deeply, deeply appreciative for that.

Matt Blumberg: But it's because we loved your name, right? We were Return Path and you were Path 101, so that kind of said a lot about it.

Charlie O'Donnell: Yeah, we had to be there.

Matt Blumberg: All right. So you went from LP further downstream to VC, further downstream to founder, and then what?

Charlie O'Donnell: Realized that being a founder is really hard. And I think there are a lot of VCs that were younger, non- partner folks that come up with a lot of ideas and see a lot of ideas and think like, " Oh, I could do that," or, " I should start this." And to be honest, I probably wasn't that great at it. Learned a ton and wound up back on the VC side, right around the time that Foursquare raised their initial round of capital. I sort of helped put that together. It was sort of a post- financial crash resurgence of New York, and people realized that you needed to be on the ground here in the ecosystem. I had been building a lot of community stuff. And so I was the helped open up First Round Capital's New York office in 2009, spent a couple of years there. Great team, great place to realize that if you didn't want to work on a team that you probably shouldn't be on your own, because it was a really great crew of folks, and I realized I just didn't want to have to ask anybody to backstop my decisions or to convince anybody else to write a check. I sort of wanted to live and die by my own sword, and so I took the solo GP route. I've raised a small fund. I've been doing that now for a little over 10 years, and we're sort of on the tail end of fund three here, and Brooklyn Bridge Ventures is now invested in about a hundred companies.

Matt Blumberg: Wow, the portfolio is a hundred. That's tremendous.

Charlie O'Donnell: Yeah. Yeah. I do about nine or 10 deals a year.

Matt Blumberg: Okay. Yeah. It adds up over time. And when you're doing early stage, they tend to stay around for a long time, too.

Charlie O'Donnell: Yeah, for sure. Not as many as I would like, but yeah, definitely.

Matt Blumberg: So I'm curious, as you think about your journey, when you left First Round, what was your decision about, hey, do I start my own firm? Do I stay here at First Round and hang out and push to be partner or do I go join another big firm? Do I call Fred back and try to create a new level at USV that's between associate and partner? You must have had a bunch of those thoughts. How did you land on being an entrepreneur in the VC landscape, which is tough?

Charlie O'Donnell: Yeah. I think the thing that people don't realize about venture is that opportunities are kind of few and far between, and different firms are set up to be shaped in different ways. And so when I joined First Round Capital, there was already four partners at the firm. There were three existing principal level people, all of whom were vying for what might have been one or two partnership positions, so it was a pretty crowded house. In fact, some of the folks when I joined were fairly vexed that I joined the sort of competition, but I wasn't necessarily there to compete. I was there to help them set up that New York office and get some feet on the ground and help introduce them to the community, so I was actually only supposed to stick around there for a year, and worked my way to an extended stay. But at some point, it was obvious that there was just sort of no room at the end, and it wasn't clear that it was a great fit. I had more of an entrepreneurial, wanted to be the person with my name on the door, that kind of thing, and wanted to be able to speak for the firm. And so, I did actually have some conversations with some other firms. And look, if my fundraising wasn't successful or I couldn't do it on my own, I would've been happy to be a cog in somebody else's machine, because I really did want to work with early- stage funds, but I figured I owed myself a shot at that point. I wasn't ready to concede and to be partner number two at somebody else's name capital.

Matt Blumberg: Right. Yeah. Well, congratulations, now 10- plus years in the past on getting something up and running, because that is not easy. When I think about the arc of your career, it is so interesting to me that I don't know that I have ever met someone that's been an LP, a GP, and a CEO. I'm sure I could come up with someone, but it's not a ton, or at least an institutional LP, and then-

Charlie O'Donnell: Right. The LP side is the rare one, actually.

Matt Blumberg: That's the rare one. Yeah, so I'd love to ask you a couple questions about the learnings and applying learnings, so let's actually go back to GM. What's something that you learned as an institutional LP that you applied to being a GP?

Charlie O'Donnell: It's definitely a portfolio approach. That is kind of the way that I look at everything. I was a GM, actually for eight years, because it was not only the four years full- time right after college, but I was an intern. I was a high school intern. My high school had this sort of special program that in senior year, once we'd applied to our colleges, they kind of kicked us out, so I was there for a long time. I mean, that day that I cleaned out my office, I had a lot of junk to bring home. And they are a really research, thoughtful, model- driven shop that has to live with the assets. It's not like an investment banking firm where you broker the deal and then somebody else deals with it for a while. So they have a really, really long- term view, and we were analyzing venture funds and really trying to figure out, well, what was it that drove your return? And are you taking more risks than other people? And what's your hit rate? And what kind of valuations? And trying to a apply this really data- driven approach. And so I do that now, and it's something I recommend to any new fund investor. I always tell them like, " You have to build the fantasy cashflow model." And that is what every LP analyst builds when they first start out is, how many deals am I doing? What's the valuation? What's the mortality rate? What's my expectation of ending value? And how does that cash play out? Right? It's very easy to say, " Well, I'm going to hit this many doubles, triples, home runs, and it takes nine years to build a company." Well, do that math and see what the IRR is, and it's probably not as high as you think it is, and one of these levers has to give. And so I'm always taking a portfolio approach, not just to the asset allocation, but to the decision making. I mean, I'll go back to this one instance of, it's the Instagram bet when Thrive Capital/ Josh Kushner, I forget how institutional he was at the time, did the$ 500 million valuation bet on Instagram the three days before it sold and got a lot of street cred for that. My first reaction is, if somebody was raising a fund and said, " 30 times I'm going to invest in$ 500 million companies with no revenue and only one logical acquirer," what do you think that fund distribution would play out as, right? Would that probably be a good fund strategy to do not just fund one, but fund two, fund three over time? Probably not. That's just-

Matt Blumberg: No one's going to put their money in that.

Charlie O'Donnell: No, no, no. Right? So that's how I think about these decisions. It's like, could I make this bet 30 times and have it play out as a good portfolio? And that's kind of where my thinking is.

Matt Blumberg: That's great. You'd have to name your firm Lucky Capital. All right, so now let's move downstream again, so now you work at Union Square Ventures, then you decide you're going to start a company. You're an operating founder, CEO of Path 101. What's the lesson you brought with you from the experience as kind of an analyst associated with VC into being a startup founder?

Charlie O'Donnell: Man, not enough, to be honest. I think not having been at a startup company... I took a one- year product management role at one of their portfolio companies, but it was sort of an already existing company, and so I didn't get to see the beginnings of that firm, and I didn't really appreciate how hard that was. I had never seen a company attempt to find product market fit, and I think those are the kinds of things I wished I had. So, I don't think I was actually particularly well- prepared for that time.

Charlie O'Donnell: Plus we weren't... I mean, we did early on do an investment in Delicious when it was Josh Schachter and a folding chair. But other than that, for the most part, we were investing in existing companies, mostly when I was there, founders that had done this before. And so, it wasn't really a great training ground. It was a great training ground... I'd like to just be an investor. I mean, Brad and Fred are two of the most thoughtful people that I've ever worked with before, but in terms of starting a company, yeah, I kind of walked into it pretty green, I think.

Matt Blumberg: Yeah, so now let's bounce the other way. Now you are an entrepreneur. You have the business building experience. It didn't work, or there were things about it that worked, but overall, it didn't end up lasting too, too long. What did you take from that experience, not just into your time at First Round, but really into your time at Brooklyn Bridge? How did the experience of being a software entrepreneur, an internet entrepreneur, shape the way you invest, the work with the founders in your portfolio?

Charlie O'Donnell: Yeah, for sure. There was a lot I learned about team dynamics. The one thing I think I was probably best with at Path 101 was hiring. I mean, I wound up hiring as my co- founder, Alex Lines, who's now a GP at Notation, absolutely terrific CTO for me. And Hillary Mason, who is now a founder, an angel investor, and one of the top data scientists in New York, and had been doing AI content generation years before it became the next hottest thing. And so I was particularly good at picking out great people to work with. But I also realized that it's not just about making individual hires, it's building a team and setting a team dynamic, and making sure that people felt like they were bought in, that there was a good feedback mechanism. So, I spend a lot of time with founders thinking about early hires, dealing with founder conflicts, and that difference between just reminding founders like, " Hey, you own X percentage of this company. This employee that you just hired doesn't. You guys are not as aligned as you might think you are. And at the end of the day, it's your vision and you need to communicate that." And so there's a lot of that early team dynamic that I sort of bring in from that early time period.

Matt Blumberg: You're probably indexed pretty long on founder empathy too. I mean, it's a tough journey. VCs that have never sat in the seat can be great at being investors and advisors, but there's got to be something different about having sat in the seat.

Charlie O'Donnell: Yeah, for sure. And it's funny, because I think if any of the portfolio company founders that I've backed are listening... I don't know. Some of them I think would say a strong" Yes" on the empathy thing, some of them probably not, because I also just realized how hard it is and where the bar is. And I'm also just really direct. One of the biggest lessons I learned is that very few people are willing to have very direct conversations with you. I remember this one time I sat down with Steve Messer, who was one of the most direct... I mean Steve will say anything, at any-

Matt Blumberg: One of the most direct ever.

Charlie O'Donnell: Right, and I was raising money and I was sort of pitching him/ getting advice and it was a difficult time period. And he said a few things that was like, " Oh, why don't you do this, this and this? And why don't you cut this," or whatever. And he cut right to the core of probably what I should have been doing, and it just seemed really dramatic and abrasive. I walked away from that conversation thinking, " Wow, this guy's kind of a jerk." And over time, Steve and I have become friends and we spend a lot of time cycling, we sort of become cycling buddies, and then I realized, no, he was just absolutely right, and probably gave me some of the most useful advice, but it was just incredibly difficult to hear. And I think, look, I've now been in this asset class for 20 years and I think I'm still probably not half as good as I need to be at delivering some of that really difficult advice, and it's something that I continue to work on, but-

Matt Blumberg: Delivering bad news doesn't come naturally to just about anybody.

Charlie O'Donnell: Right.

Matt Blumberg: Whether it's advice or saying" No" when someone pitches you, it's just hard.

Charlie O'Donnell: Yeah, for sure. For sure. And I think the nos when somebody is pitching you, those are easier. Those are much easier, because you could say, " Hey, I could be wrong, but I'm not going to get there on this. Here's why." When you have to deliver bad advice to somebody that you've bet on where you're basically like, " I liked this idea and thought it was good, but your team has not executed, and so here we are." Right? So, " This was good. You didn't get there," is a much harder conversation than, " I don't think this is good, but I could be wrong."

Matt Blumberg: Right. Yeah, yeah, that's a fair point. I'm guessing people who listen to this know who Fred and Brad are at USV and know who Josh is at First Round and Chris and whoever else. What was it like working with each of them, not at the beginning of their journeys, but pretty early on in the most recent stage of their journeys? You know, people think USV is now seven or eight partners. Its brand is very different than it was in 2004 or '05 when it was Fred, Brad, and you and a couple of other people.

Charlie O'Donnell: Yeah. I think the things that I... First of all, they're all just super different people. Josh is very much a builder of things and really likes to get in, sort of understand how things work. I think Fred is very close to that, not as a sort of builder/ entrepreneur. He is not the firm- building type and almost famously is one of the few really successful VCs who has not been on the entrepreneurial side. But he's certainly curious about things on that level and how that interplay works and is a very detailed guy. And Brad is a really kind of academic big picture thinker.

Matt Blumberg: Brad is inaudible for sure. Yeah.

Charlie O'Donnell: And it's actually interesting because Brad and Fred, I never got to experience USV as the sort of full four partner, five partner, whatever they are now. I was working, and as the analyst associate or whatever I was, it was Brad and Fred, and they complimented each other really, really well. I don't think Brad gets enough credit for the origin of the thesis of that firm, because you don't have Union Square Ventures without the interplay between the two of them. I'm not so sure that... I think Josh built a team of the best players that he could find that match a strategy that he came up with. And it's funny, I've never really thought about this. I'm sort of thinking on the fly. I'm not so sure, and Josh might feel differently, how much they are compliments to Josh. Although I will say when Josh first started out, he was fairly young and he co- founded the firm with Howard Morgan, who had a ton of experience. And so, Howard is the guy that brought the internet to Philly, basically, and so I think Howard was very much a mentor to Josh in the tech world sort of early on. But I think over time, Josh had a good idea of what he wanted First Round to be, and found the best team to execute on that, but weren't necessarily picking out people who were like, " I know I'm not good at this, therefore I'm going to go and find somebody else."

Matt Blumberg: Sure.

Charlie O'Donnell: A couple things about-

Matt Blumberg: Lots of different models, lots of different successful models.

Charlie O'Donnell: Well, that's exactly what I was going to say is that I think you have to have strategies that sort of match who you have. And that's why both of those firms have been successful with very different approaches.

Matt Blumberg: Right. So now we're in early 2023, late winter, early spring. What does the world of early- stage investing look like right now, and what do you think is going to happen to it in the coming year?

Charlie O'Donnell: So look, I think the first check investing world is typically going to look much more like it did in sort of call it 2017,'18,'19 kind of thing. We're not crazy town, but deals are getting done. I mean, I have just participated in... I've said" Yes" to a couple of deals where they won't take a ton of time to fundraise, and there are good stories, and they're good founders. So people are writing checks. The problem is in the later stage, the bigger check firms that may have overhang in their existing portfolio, where they're looking at their portfolio going, " Hey, we've got some holes punched in this thing. We have some valuation challenges, and when's our fund come up for the next fundraise?" And that has made them very skittish about writing checks. They have to figure out who they need to support. And there are some firms going, " Hey, barring a miracle, I don't see how our LPs back us for another fund," which is a real issue. So, whether it's Bridges or As or Bs or whatever, I think that world is going to be fairly slow for the rest of the year. And it's also driven by the fact that some of these folks have an existing portfolio that in any other normalized market would've gotten out into the public market. And I just don't think there's going to be, frankly, any public market in 2023.

Matt Blumberg: Right. There won't be a public market. There'll be fewer exits and the exits will be smaller.

Charlie O'Donnell: Right, right. So you're looking at 2024 for the beginnings of the exit market to sort of start opening up...

Matt Blumberg: Do you think it's going to ... It's interesting, the markets can get pulled from the top or pushed from the bottom, and when the exit market starts to open up again, that makes everybody feel good about opening the purse strings. But the other thing you said that's an interesting dynamic, and we're seeing this with Bolster Ventures too, is the first check is still open for business, right? Because the first check doesn't have to worry about macro. You're backing companies that are in build mode, and you're all in there raising a million bucks or a million and a half bucks or something, or less, and it's usually on price now. So you can see how there'd be pull from the top when exits start opening up. But all these companies that have been getting first check for the last six months, nine months, 12 months, by the time you get to the back half of this year, a bunch of them will have succeeded and will be ready for their first institutional money too, or bigger institutional money.

Charlie O'Donnell: Right, right, for sure. And those companies, or the checks you're writing now, who knows what the 18 to 24- month timeline is going to be? Now that's something that... worry about next year, but the thing I have to remind companies, and I think VCs need to remember this too, is you can't cut your way to success. I mean, at some point you have to invest to grow. And I was on a call the other day where some of the other VCs around the table were sort of saying, " Well, we should have a below low case." And I was like, " If we don't get this low case, no one's funding this company."

Matt Blumberg: Right. What inaudible

Charlie O'Donnell: Yeah, I don't know what the point of cutting even more than we have, because what's going to happen is the market will open up and there will be companies that will have succeeded, despite not being heavily resourced, and those are going to be the first ones out the door. And you can't be a company that has been growing 10 or 20% annually and think, " Someone's going to write me a big Series A check at the end and pat me on the back for just lasting." That's not enough. They need to see that this still has the kind of growth potential that can return a fund.

Matt Blumberg: Yeah, so people inaudible

Charlie O'Donnell: So, inaudible by the way, increasing the chance that this thing's going to be a zero. You sort of had to keep driving as you're going off the cliff.

Matt Blumberg: Yeah, so I think at the later stages people are saying about this year, like, " Oh, flat is the new up," or something like that. I think at the early stages it's not that, it's up is the new up a lot, or something.

Charlie O'Donnell: Right, right, right.

Matt Blumberg: Yeah. Well, that is great advice. You have to keep investing to get somewhere, for sure. All right, so you started Brooklyn Bridge Ventures in what year?

Charlie O'Donnell: 2012. The first money came into the fund in September of 2012.

Matt Blumberg: All right. So you're just over 10 years, and what's next for you?

Charlie O'Donnell: The companies that I invest in, I stay active about the first two years of the company's life. I mean, I'm happy to hop on a call with companies I invested in eight years ago, but realistically, there's somebody who wrote a bigger check after me who's sort of taking the helm and on the board and all of that sort of stuff. The deals I do now will take me into 2025 for my activity level, and it's sort of an interesting milestone because that puts me 20 years in this asset class. And I've been thinking a lot about what that means and what it has been like to do this job from the ages of kind of 25 to 45, roughly. And I'm a very different person now than I was at 25. I'm now married.

Matt Blumberg: You're a dad.

Charlie O'Donnell: I have a beautiful ... Yeah, I'm a dad of an absolutely beautiful, smart, terrific little girl, and who has been on many board calls. I mean, she started out life 80 days in the NICU and I got three term sheets out while I was in the NICU, which I'm pretty sure is a venture record. I don't know who captures those kinds of things. I think it's probably not realistic for me to do my job the way I've been doing it from the period from 45 to 65, and it's a couple things. Most people at this time period in my life do one of two things in venture. They either go later so they don't have to worry about turning over every rock and seeing if you're two people on a PowerPoint is a thing. They can sort of wait. And it really shrinks the opportunity set. It really makes sourcing take up a lot less time. That's just, to be honest, it's just not fun for me. I like being the first check. I like dealing with entrepreneurs at that stage. Or they build a firm, frankly, and sort of like we were talking about First Round Capital where there's how many analysts or principal level type people and partner support teams and all of this sort of stuff. And you really got to want to be an entrepreneur and a company builder to do that, even if it's still on the smaller scale, and managing teams is just not something that's really interesting or compelling to me. I've never wanted to hand off the deal flow to an analyst. So I've kind of come to the conclusion that this is probably a good time for Brooklyn Bridge Ventures' deal- doing days, the new deals anyway, to come to an end. I will have put three funds to work, a little short of$ 40 million, across a hundred companies, and I've still got a lot of work ahead of me to help shepherd those companies to their Series A and beyond and exits and all that sort of stuff. And that's going to take up the vast majority of my time for the next couple of years. But on the deal- doing side, there's a whole new crop of really hardworking, incredibly intelligent and focused younger folks who have the bandwidth to do this. And there's been a ton of specialization, that you look at the kinds of things I do where, okay, I have a newsletter and I do some events and do some other stuff and I help founders, whatever. Well, yeah, but then you've got folks like Harry Stebbings, who does The Twenty Minute VC, and The Twenty Minute VC is almost a company in and of itself. He's got a team working on it, or somebody who writes a newsletter, knows all the growth hacks and has a hundred thousand followers or whatever. It's like for each aspect of the way that I've done this, to be honest, I could probably find some 27 year old who's doing only that thing and doing it 10X better than when I started. And not only that, is purely focused on AI or enterprise SaaS or what have you, and is doing a super deep dive and is probably the first, the best port of call for the founder in that stage. I mean, it's now incredibly competitive, and I think I probably would get much more enjoyment out of helping to share what I've learned with that generation versus competing against them, to be honest. So I don't know if I'll end up getting into some investor education stuff or community. I mean, I've always really liked running events and passing on that wisdom. In fact, we do this series called New to VC where we take existing partners at VC firms and share the really nitty- gritty of best practices on being a board member and goal- setting and all that sort of stuff. So yeah, I'll probably do some of that, and I'm also just thinking about making the world a better place for my daughter and my family. And so there's a bunch of things that I am sort of noodling around from an impact perspective. I just read A Billion Americans, a really, really great book from Matt Yglesias, and one of the things he was talking about was sort of population growth- centered policy, and how do you make it easier and less expensive to have kids, for one? I mean, that was a big aspect of it. And I think about that a lot. I'm very, very fortunate that we can afford childcare and that we have flexible jobs. We make it far too hard for folks to be able to grow families, and especially in cities, and so that's just an area I'm super curious about, what I can do if given a 20- year time horizon to do it. So that's in my limited amounts of spare time while I still have a full portfolio of companies. That's a little bit where my head is at.

Matt Blumberg: Yeah, and I mean, look, it's definitely going to be big news when you announce this publicly, and we'll put this podcast out around then so you can control the timing. But it's certainly going to be big news for the New York tech scene. I think what people don't necessarily realize is you're going to be Brooklyn Bridge Ventures for the next 10 years, because the companies, you may not be doing new deals, but you're still doing follow- ons, and the companies you invest in this year are going to have a long life and you're going to be there with them. But to me-

Charlie O'Donnell: I'm not getting out of the venture business for quite a long time. I'm getting out of the new checks business.

Matt Blumberg: Right, but even that's going to be pretty big news in New York. There's no question about it.

Charlie O'Donnell: Yeah, and I think one thing that I'm pretty proud of, to be honest, is I do think that some of the early community building work that I put in, I see remnants of it. And you look, we have this fantastic sort of meetup and gathering culture here. There was a time where there were literally two things to go to, the next NY events that I put together, and Scott Heiferman's New York Tech meetup, and that was kind of it. And so, I feel incredibly proud of whatever my little part in helping to build the community here was, and I also feel like-

Matt Blumberg: Not so little, not so little.

Charlie O'Donnell: And I also feel good that, should I stop writing new first- time checks, that there's plenty of other people to pitch, and there's plenty of other really smart folks, even folks who are not in New York. I mean, that's one thing that's really changed a lot is, everyone is willing to do a New York deal, and everyone pretty much has a New York deal and loves coming here. You look at any of the top names in the valley and they're all coming through here, or some of the folks from bigger funds have second apartments here. So, there's no shortage of check writers.

Matt Blumberg: That's for sure. And that was a trend pre- pandemic, but now that 90% of that work can be done on Zoom, it's clearly opened things up.

Charlie O'Donnell: For sure.

Matt Blumberg: All right. So I like to end these with a speed round of one question, but given you and your background, I'm going to do two questions.

Charlie O'Donnell: Okay.

Matt Blumberg: First one is, one piece of advice for a new VC, or someone who's thinking about getting into the early- stage VC business.

Charlie O'Donnell: Optimize or just come up with a reason why someone would want to meet you and spend time with you that doesn't have to be... that is not about the check.

Matt Blumberg: Great. And now the thing I ask everyone who's on here, one piece of advice for founders, for CEOs, about scaling their business, scaling themselves as a leader, scaling their teams, scaling their board, a piece of advice for a founder about scaling.

Charlie O'Donnell: First of all, act like an adult company from day one. Create a plan, create a financial plan. I mean, that's one of the things I learned from you. I'll never forget hearing about how you wrote an HR policy that included a seven- year sabbatical a couple of weeks or months into starting Return Path. And I said to myself at the time when I heard that, I was like, " I'll bet you that there is an increased chance of survival for seven years when founders make seven- year actual plans and policies." And I've seen just too many companies just try and imagine that they're waiting for some time where things are going to get more serious or more organized, and there isn't. You have to do that, and the earlier you start doing it, the easier decisions will be, the easier collaborations will be. So yeah, take it seriously from day one.

Matt Blumberg: All right. That's a great place to end. Charlie, thank you for being on The Daily Bolster. Good to talk to you. Congratulations on your decision and good luck. I'm curious and excited to see what comes next for you.

Charlie O'Donnell: So am I. Thanks for having me.

DESCRIPTION

Today’s guest is Charlie O'Donnell, founder of Brooklyn Bridge Ventures. He and Matt are diving deep into the journey between entrepreneurship and venture capital. Charlie’s career has given him insight into a myriad of perspectives that influence his work with founders now, from his focus on team dynamics to his direct but empathetic approach to difficult conversations.

Later in the episode, Charlie and Matt talk through the current state of the market, the types of deals that are seeing success, and what’s next for Brooklyn Bridge Ventures.

Today's Host

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Matt Blumberg

|Co-Founder & CEO, Bolster

Today's Guests

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Charlie O’Donnell

|Partner, Brooklyn Bridge Ventures