I hosted a $750m private dinner for startup CEO’s in NYC

Brandon Bryan. He's Harlem Capital's managing partner. >> I don't know if we pointed out that fund won $40 million, but now your firm is managing what? 174 million in assets. your boy. What's up, man? >> How are you? >> How are we? >> Good. >> Thank you. >> Yeah, good to see you. How are you? >> So, what are we doing tonight? >> Tonight, we're on our way to one of our dinner series that Harlem Capital host. It's a series called the Winners Circle where we get a group of really elite founders together all in one room. We do it Jeffersonian style, so it's one conversation and we really focus on off the record type of topics. So, talking about most likely AI tonight, talking about fundraising, talking about hiring folks, all types of different things I assume that we'll be discussing tonight. And actually, from the last video, the individual who raised at a $2 billion valuation, and I lost out on that deal, he'll be here tonight. So, maybe we'll be able to chat with him and chat and and talk a little bit about his latest fund raise. And then we're hosting this with one of our founders actually. So Dion Nicholas who founded a company called Forethought. He has raised over 100 million for that and he's going to be hosting and being the person who's kind of leading conversations tonight. So it should be super fun. >> How important are more informal meetings like dinners compared to more formal meetings in the office? I think formal meetings in the office seem very corporate, but when you do meetings outside of the office, whether it be like there's some people I only do meetings in their 7 a.m. workouts, this person, the easiest way to talk to this person is at a 7 a.m. workout. Some folks like to go to concerts, some folks like to go to basketball games, some folks like to do other things. Some people like to do ax throwing, running, hiking. We just meet people where they are. We build relationship where they are. Some of the things we also do is like if a founder really loves to do something, we'll do something with them and then have them invite all of their friends. So, for example, Dion, who we're hosting with tonight, really loves karaoke. So, we already have a big plan to host a karaoke night with him and all of his friends. And you got to remember like a players always hang around other A players. And so if we're able to like build that genuine uh community, network, connection, and trust through, you know, friend of friends, like that could be really valuable for us in the future, >> right? What's like the craziest business meeting you've had, you think? Like craziest like location? >> Craziest location. >> The craziest opportunity for us when like a LP invested in our company was someone reached out to us on LinkedIn, did an interview with us. This was like pre fundraising, even our first fund. And then that person knew a billionaire, connected us with that billionaire. We pitched a billionaire, they invest, and then that billionaire was connected to one of the top private equity shops. And that led to that private equity shop investing. And then because that private equity shop invested, a competitor in that space anchored our fund. >> Wow. So literally because of this individual wanted to reach out to us on LinkedIn, those multiple degrees of separation started to compress. And I think that's the whole point of hosting the dinners. That's the point of going to the 7 a.m. workouts with founders or anyone else. You never know who that person might know, who they may connect you to, or lastly, what they're seeing behind your back. Like what kind of trust have you built with them so that they can describe you in the right way to make it a no-brainer for whoever they're connected to to want to meet you, to want to be in a room with you, to think highly of you. Yeah. >> A city where dreams are made of a city of life. All right. So, we are here at the dinner at Scarpetta. Jared and Gabby on my team. They are running through the logistics because you don't put one of these dinners together with just wishes and ideas. You got to strategically place people in the right places. You got to make sure that the people who are sponsoring the dinner feel like they are getting their ROI. And then we also have Elliot who has kind of shot photography and video for us for like the last five years. He's actually like shot Jared's Jared and of my business partners like wedding photos for them. Yeah. So he's part of the family. >> What do you think about when you put people together? When you think about putting people together at these, if you have sponsors who have ROI, like let's say you had a bank, you want to put the bank next to a new founder who like potentially hasn't started a company yet, that could be a good customer. So, you want to connect like minds that you think will instantly hit it off and have a good time with each other. The name of the game is to find any similarities [music] or symmetry. You start to connect those because typically if there's one dot to connect there's like many dots to connect. >> Yeah. >> So far great. >> It's been >> you doing all right? >> I'm Dude, he signed. >> Oh [ __ ] >> Signed. Yeah. >> Let's go. Between me texting you >> literally in the last like 2 hours. >> All right. So Dion, who's who we're hosting a dinner with tonight, he is trying to hire a hot shot engineer. I happen to know that engineer. So I've been texting back and forth with the engineer. And so I see Dion come in and I asked him, "Are we joining the team on text and then Dion says, "Hey, he is now at the company. Big win. Big win when you get hot shot engineers to sign with your portfolio companies because one engineer can like change the business." So even though we didn't even start the dinner yet. Very good news. >> Yeah. But it was like an 8-year sales cycle. >> My god. Hold on. Claire is one of our first investments ever. >> She also has this Ohio State connection which I love. And she just closed the biggest deal in her company's history. >> And she just told me it was a 8year sales cycle. >> And you were saying that you met this guy 8 years ago. >> When I was 20 years old. >> When you're 20 years old and you told him you're going to be the head of business development or something. >> B2B period care. >> B2B period care. Women hygiene. Yeah. >> And eight years later, you sent him 42 updates. >> Yeah. >> Over eight years. >> Over eight years. >> And then in 2024, he said, "Do you want to talk about owning our women hygiene products?" >> And it took you 12 months to close uh >> multi- [ __ ] figures. >> Nine figures. >> Nine figure dealing%. Yo, >> crazy. >> Congrats. Congrats. That's a big deal. >> That's a big deal. >> Nine figures. I can count that high. That's high. >> Big fishing. [music] Take a group of y'all to catch me. I draw quicker when it start getting sketchy. A bunch of them think they hard just edgy. I put >> probably going to be more marketing like. But anyway, the question I'm posing with that pream like speed and people getting back to us. And so if we're looking at a founder looking for a hire, you email their last boss, they get back within a day or a couple hours. Probably a good signal. They're slow, not as good of a signal. So, >> I want to add a point to this. This I think references have become so much more important during the AI era specifically [laughter] specifically because like people can say anything and like make up anything. And so, we have like probably doubled or tripled down on our references. And I have actually I I agree with JT with with Jared, but I I like asked three questions now. Like I so I made my references like super simple. Number one, is this person exceptional? Number two, would you work for them? Number three, are you investing your personal capital? >> The answer to those three things, I don't really need to ask more. [laughter] >> The the more might be like, I want a little bit more of the the matrix. If you say you said it was a matrix, >> mosaic, I want more of the mosaic of an individual. But those three things should really tell me, especially if they were a previous investor in your company, they used to work at your company, or they were your boss before, like those three questions should really help me understand like what type of founder you are. >> Kind of just like, oh, these are all the things I'm good at. These are all things I'm not good at. Let me not be. >> The dinner went extremely well. We had 20 plus founders come together for an off thereord conversation. We also got a few people who are going to be on our podcast in studio. And the interesting thing about this is like the more events that you host, the more contact you can have, the more opportunity for people to be inserted into all the things you do, all the programming that you do. >> What was your biggest takeaway from tonight? >> My biggest takeaway from tonight is that relationships matter the most. We had an opportunity to invite a few of our network, but Dion, who we partnered with, invited a lot of his peer network. And many of those people came just because of him. And so realizing the gravitational pull of the second or third degrees of separation in your network is really important. And then following up on those people, inviting them out to things, including them in your programming. During this dinner, we cold call people. So, we make sure that every single person at the dinner speaks and we make sure we have a list of questions just in case we run out of things to ask. We have a list of questions to ask every single person. And I think when you do that and you have a genuine focus on making people feel included, they turn around and and want to do things to like support you and to be helpful with you. And so, tonight I think was just like another one of those times where I realized like like building community is exciting. In a sport like venture capital where community is really important, like you can actually start to find big opportunities of success when you build community the right way, when you're intentional about it. >> I think I think I think I'm almost, man, I'm I'm pumped. What do you think about it? Did you think it was good? >> Yeah. Right.

In this episode, you'll see a venture capitalist in NYC host a dinner with tech startup CEO's who have raised more than $750m for their companies. They have off the record conversations about the struggles of being an entrepreneur. Finally, you’ll see him share why building relationships is the most important part of business Stay tuned for next episodes where you'll see more entrepreneurial vlogs on investing in tech companies in search for my first billion dollar company 📖 Chapters 0:00 Intro 0:22 Heading to the Winners Circle Founder Dinner 1:32 Why Informal Meetings Build Stronger Relationships 2:44 The Craziest VC Connection That Led to an Investment 4:11 Behind the Scenes of Hosting a Founder Dinner 6:15 An 8-Year Sales Cycle That Became a 9-Figure Deal 7:43 The 3 Reference Questions Every VC Should Ask 8:24 Outro WHO AM I: I’m Brandon Bryant. I am a co-founder and partner at Harlem Capital, an early-stage venture capital fund. My number mission is to invest in founders building the next generational companies. Follow along on the journey!