This Week in Startups - Bored Ape Madness with The Infatuation’s Andrew Steinthal + Breaking into VC with Nicole DeTommaso | E1275

Episode Date: September 1, 2021

The Bored Ape Yacht Club NFTs have been going crazy in the secondary market, Jason brings on collector and co-founder of media site "The Infatuation" Andrew Steinthal (2:04) to chat about why he bought in, why he's not selling, and the overall mechanics of the community. Then, TWIST producer Rachel interviews the Nicole DeTommaso of Harlem VC (33:25) about how she broke into venture capital with a pitch deck!!!

Hey, everybody, hey everybody. We got an amazing show for you today. We talk about the Bored Ape Yacht Club. This is an NFT collection where you buy into it for a couple of Ethereum. And then you get special features and club benefits while we talk to Andrew Steinfall, who is a co-founder of a restaurant review site in New York called The Infatuation, which also purchased the Gap in 2018, by the way. And he got in early on this craze, bought one of these NFTs for $9,000. Now he's sitting on a couple $100,000 in NFTs of monkeys, of these board apes. And he explains to us the craze. And it's actually kind of fascinating. It's somewhere between collecting and speculating and gambling and Soho House, hard to explain. But we get into it. And I think it's a really important

subject that we all have to get educated on because this company is producing hundreds of millions of dollars in revenue already in the first year of its existence from nothing, no investors. So, And then in the second half of the show, our reporter Rachel interviews Nicole de Tomaso. And Nicole is somebody who broke into venture capital recently working at Harlem VC. And she explained on Twitter how she did it with a pitch deck. So I sent Rachel out to interview her. It's a great interview. You're going to love it, especially if you're thinking, hey, how do I break into venture capital?

So stick with us. This week in Startups is brought to you by Squarespace. Turn your idea into a new website. go to Squarespace.com slash twist for a free trial. When you're ready to launch, use offer code Twist to save 10% of your first purchase of a website or domain. Our crowd helps you invest early in pre-IPO companies alongside professional VCs. If you're interested in investing, you can join our crowd for free at OUR-C-O-WD.com slash

twist. And Belay. Get back to doing what only you can do, growing your organisation. and leave the rest of Belay. Text, twist to 55123 for a free ebook to learn how. Okay, everybody, in our first story, the Bored Ape Yacht Club has gone supernova over the last couple of months, and they are going to do a sale with Sotheby's

that could bring in tens of millions of dollars. If you don't know about the Bored Ape Yacht Club, is an NFT project where people can buy an NFT of an illustration of an ape that has seven different features,

the eyes, the hat, the mouth, earrings, background, all that kind of stuff. And they're kind of like beanie babies or other collectibles. They were created by something called the Yuga Labs.

And they have been one of the top five collections by volume traded on the NFT Exchange OpenC, which we had on the program. And I thought we'd have somebody on who has been part of the club for a while. And if you're part of the club, you basically may get your Twitter avatar, it seems. With us today, Andrew Steinthal. Did I get it right? Andrew. You nailed it. Okay. So you're the co-founder

of Restaurant Review site, the infatuation. Correct. And you purchased Zagat in 2018. Congratulations on that. Oh, thank you. Who owned that? Was that from Google, you boy? it or somebody had it in between Google? No, we acquired that directly from Google. So you joined and bought one of these NFTs. When did you buy your NFT for the Board Ape Yacht Club? I got in probably about two and a half months ago. So it was like, I sort of, how I looked at it was I missed the like friends and family round,

barely missed the seed round and then kind of got in as the Series A was just, kicking off. And so you became aware of it, I assume, because everybody on Twitter was changing their avatars into this? Yeah, I mean, similar. What happened was, was that I got obsessed with NBA Top Shot. Like, I was onboarded into Top Shot in January, saw the light of what NFTs could do from a tech standpoint and from the access standpoint and just got really, really into it.

I think TopShot sort of was the enabler to a whole world of other things. And so a lot of folks from the Topshot world jumped on Board Apes as soon as that launched. And I had watched it. I hadn't minted another NFT yet outside of the Top Shot stuff at that time when Board Apes launched. But I was definitely paying attention to it and was flirting with getting involved. And then ultimately when it was like, all right, this is this thing. for real, jumped on board.

How much did you pay for yours six weeks ago or 10 weeks ago whenever you got it? I paid 4.3 ETH for mine, which at that time, ETH was hovering around a little over two. So it was close to, it was like $8,000, $9,000. And my wife was like, what are you doing? You're insane. So you spent $9,000 U.S. dollars on essentially. what people would say is a GIF, just basically an image. But in fact, it's an NFT, which means it has some additional capabilities,

including that you can trade it and that it's on the blockchain. True. Yes, I did. And what I found interesting was, you know, I think that the Beanie Baby comparison and the GIF comparison are all like, yes, you can make those comparisons. But I think when you start looking at it more as, tokenize membership. When you own something, you get, you know, different kinds of access and different types of perks. And when you start thinking about it outside of the JPEG is just the,

you know, your membership kind of ID. So let's explain to people what that is. If you go to the website boardApeyat club.com, they explain that they made 10,000 of these board apes, that they initially cost 0.08 Ethereum to buy, which was a couple of hundred bucks. They then got sold out. They all moved to the secondary market, and one of the, I guess,

the major secondary market for NFTs now is OpenC. And they said, the first thing you're going to be able to do with your membership is, and they said basically here, your board ape doubles as your Yacht Club membership card and grants you access to the members-only benefits, the first of which is access to the bathroom,

a collective graffiti board. So you're going to be able to, as a grown man with a job and a wife, take your $9,000 NFT and go into a website and write graffiti on a website. Am I correct in summarizing the first benefit you will get from your NFT? I guess so. True. I have never once been in the bathroom writing with graffiti there. Got it.

Now, the upside to this, having to explain to your wife that you spent 9,000. on a JPEG is that these are worth, am I correct, 50 Ethereum now? And Ethereum is worth $3,000 or $4,000 as we're recording this on September 1st, 2021? Accurate. Yeah. I mean, there's peaks and valleys. Things go up and down. But this has settled into a really solid range between 40 and 60 right now as a floor.

So it's worth over $150,000. So you're sitting there with an ape worth 150,000 that you paid 9,000 for. There is no, while there is a limit of supply with this, there is no telling when this could become a beanie baby and be completely worthless or there could be other things that people move on to. So what is your thinking currently sitting on, you know, a six-figure gain on your very savvy purchase? My thinking is that the world of Web 3 blockchain and NFT coming together is transformative and Bay Area. Sorry, Bay, this is, I'm on your show, so I'm thinking Bay Area. Right. Board

8th Yacht Club is one of the initial communities that has been built out around this monumental movement and change. And, you know, if things keep going in this direction, it's going to be extremely valuable moving forward. And honestly, it's something that's been really, really fun to be a part of. I think that, yes, it's an image. Yes, it's a JPEG, it's an NFT, all of that. But it's really been about the community and have been about being a part of this explosive growth of a whole new way of crowdfunding startups.

And at Yuga Labs, who you mentioned, who is the parent company of Board Apes, have been doing just an unbelievable job of adding value to their token holders. You know, one of the things that happened this weekend, right? You know, you mentioned there's only 10,000. Yes. That's my understanding. Yes. There are 10,000 original board apes.

But, you know, the price has gotten so crazy. And you wind up having WakaFlaka Flame and Steph Curry all joining the community. And the price is continued. Curry bought one for a reported 180,000. Right. And so you're, you know, things keep going up and up. And it makes that barrier of entry more difficult. But if this thing really needs to scale, it's going to need to be more inclusive in some capacity.

Right. So what they did this past weekend, which set the set OpenC and the world of discord and Twitter on fire was they air dropped. And this is a big part of what this world of NFTs and adding. value is about is they air dropped for free to each token holder of an original board ape, what they called a serum, which is a basically chemistry class where you got dropped one of three different options. One was a M1, which there were 8,000 of or something. And one was an M2 that there were about 2,000 of.

And then one that there was a mega that there were eight of. And you randomly got one of the mutine series. You randomly got one, right? And the night that I received my serum, I was lucky. I got one of the M2s, I could have flipped that for 30 that night, right? Like a $100,000 air drop for free coming to my wallet. What do you do with the serum? You gave it to your monkey and it evolved it or it made more monkeys?

Yes, you give it to your monkey if you want to burn it and use it and you create a whole new type of mutant monkey. And your original monkey's gone? Nope, your original monkey stays. Nothing happens to your original monkey. So you get a second mutant monkey that you can own or sell? Correct. And this is not the first time they've done this. They've also given dog like these things that were called doggos, which are companions

for your apes. So those were air drops for free that are added value in free money essentially if you want to flip it. From websites and online stores to marketing tools and analytics, Squarespace is the all-in-one platform to build a beautiful online presence and run your business. With Squarespace, you know you can blog and publish comments. You can promote your business. You can announce upcoming events or special projects.

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air drops, free items and collectibles. So this would be as if you bought a pack of baseball cards or a comic book if, you know, I think we're both in the Gen X range. And then Marvel Comics said to you two months after buying your comic book, by the way, we're sending you a special edition of Spider-Man called Venom and you get it for free. And we're going to send you a psychic. And we're going to send you this, you know, Teen Titans comic book. And you just get free collectibles on top of it just because you were early to the comic book collecting club.

Exactly. And I think it's also about, you know, they've been doing some really cool collaborations for merch and, you know, things like that. They just did one with the hundreds that if you own an ape, you get access to. I've honestly, like, I mean, I'm a person who I'm a collector. I like, I like stuff. I'm sort of a hoarder-ish. But I also, like, I haven't bought more merch from a specific thing than I have for

board apes in the last, like, I mean, the last four months, I've probably acquired four hoodies, two hats, three t-shirts. I mean, that hasn't happened since I was in high school and buying Blink 182 stuff, you know? So they're creating a brand of collectibles, and is this based on a specific artist's work because it is a unique art style? Is this like a specific art style that they are doing here that's appealing to people? Well, I think that I think the art is cool in general, and people reacted well to it. I think you see a lot of these PFP profile pictures. type projects happen. Some of the art is really interesting. Some of the art is whatever. I think the apes were sort of first. Obviously, it all just follows in the in the footsteps of Cryptopunks.

And I think for for the OOGs of blockchain and crypto and NFTs, Cryptopunks was it. But a lot of us who got in this year, we didn't have a chance to get involved in that from the beginning. So this is sort of our beginning. And I think that like, there's a lot of. There's so much momentum and so much heat in this space right now that like that collective force of people coming together has really, really, really helped transform this company, you know, with the board apes into into the stratosphere. And I can't stress enough how good a job that Yugo Labs has done with this responsibility of all the money they've been making and then staying true to the people who have believed

in them. So it's been really interesting. How are they making money? Did they just own a lot of the 10,000? and they just are now selling them in lots? Is that what the Sotheby thing is, or is that somebody reselling it? And they just let all 10,000 go. I'm not, so they let all 10,000 go from the initial mint.

So they sold out of the mint initially, which brings in, you know, a significant amount of money. I mean, and then I have to look at the- Well, it's like $250 per at the time. So a thousand would be $250,000. So they made $2.5 million. But this lot that's being sold at Sotheby's is going to be worth for, you know, 10 or $20 million. So they're making all of you.

rich, but it doesn't seem like they got rich. Yeah, but they get, they get a cut of every single resell. That's the beauty, that's the beauty of all these NFTs and smart contracts. It incentivizes everybody to play together and make money together. So when you're cut into every transaction, what, do you know what they get of every transaction? Five percent, ten percent? Yeah, it's either, I'm not a hundred percent sure, but it's, it's one of five percent or ten

percent. Um, it's, so that's brilliant. In other words, if they get everybody whipped into a frenzy about collecting these and participation in it, the more people who participate, it would be as if the Beanie babies or Marvel Comics got included in the resale. You and I are fans of the Knicks. At some point, the NICs said, we're going to start our own resale channel or the NBA did because they said, listen, all these ticket masters and everybody has their own ticket resale, we don't get any of the aftermarket. And then they got a piece of it where if you were a season ticket holder, you could

resell your tickets through the NICs and the NICs would get a cut of it. And now that's all memorialized in smart contracts. Correct, which is what should happen. You would think the original and the artist would. So I've heard that people are doing fractional ownership of this. So have you thought about taking your NFT and then selling 10% of it, giving your wife back the $9,000 you spent on initially and then giving her another $10,000 and taking her on vacation?

Well, I've already, I mean, the NFT trade has been wild. So we've already made up that money, no problem. in the last couple months. Oh, did you sell your serum and your second monkey? I haven't sold my serum or my second monkey, but... Did you use your serum? I'm holding it right now. So you're holding a serum. So you didn't get a second monkey yet. You just have your serum and the potentiality of a second monkey. I bought, I bought an M1 serum so that I could make a new monkey from my current monkey. So I have a mutant monkey and my current monkey and my M2 serum, all sitting on ice, not looking for them to go anywhere anytime soon. But you find some of the blue.

liquidity elsewhere in NFTs that you don't care as much about. You buy those, sell those at higher, so you keep stacking your ETH to play the game. So, which is all that this whole thing is, it's just, there's a lot of game theory in, in all. Yeah, what was the game theory here now, which is, I would guess, this is like there's a poker game you play that was called guts, which is like, who can hold onto their chip the longest? It was like a crazy game I played once in New York where if you had it, you would decide to put a chip in your hand, everybody will put their hands out, you put your hand behind your back, decide if you're going to put a chip and play your cards.

If you have the chip in your hand, you have guts and you have to match the pot. If you don't have the chip in your hands, you're folding. And I got into this one time and I happened to have a good hand and I won like $6,000 because we had to match the pot like three times. It starts out with everybody's got $100 in the pot. It gets quickly insane. But this is that is that this is like the prisoner's dilemma whoever gets off first and gets the money.

But then if you were to sell and take your couple of hundred grand and put a down payment on an apartment or a second home where I don't know what station you're out in life, you seem pretty successful. But then you would feel really stupid if it goes to a million. Yeah. I mean, look, it's all it's all about. I mean, look, a lot of the holders from crypto punks are kicking themselves for getting rid of their punks. Right. I mean, if history repeats itself, right? And this is one of the most important projects that, you know, is on chain with NFTs.

Then, you know, I'm in the camp of hold and see where it goes. I mean, look, this weekend alone, we're talking about money, right? Faroque, who's a guy that's been an unbelievable spokesperson for NFTs and has built a brand on Clubhouse and Twitter, he sent tweet out on Saturday night that board apes for the, mutant drop in one hour sold 92 million U.S. dollars worth of mutants. 92 million U.S. dollars worth of mutants. Wow. So anytime they can basically gift their early members with $100 million or more,

because that was only what that's not a gift. So that was, so they did the serums. Those were free. But in addition, they also dropped a whole new version of apes. They dropped 10,000 mutant apes. which had a lower price point. What did those new names go for? I think it was like 2.5 or 3 each as the minting cost.

So they got that money. So they got 10,000 per? Exactly. They get all that money and then they also get a chunk of all that secondary action that just goes nuclear as well. Oh my Lord. So they just printed $100 million. Correct.

They proved yes. Like, I mean, it's. What is happening in the world? The approximate number that for Oaks said was $163 million in that one day because of the secondary action that were already happening on OpenC across Newton's and apes too. So 10,000 people came in and paid $10,000 each for to be part of this club. Some people, I guess cynically would say multi-level marketing type endeavor, I guess. collectibles would be at, what are you in your heart of part look at this as? Like, a gam, as gambling or collecting or something new? All around the world, tech companies are

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Our crowd. So, join the fastest growing venture capital investment community at our crowd.com slash twist. Once again, our crowd.com slash twist to join for free. You're a sneakerhead, right? I am. Yeah. But sneakers never got crazy like this, right? You don't have an example of your sneakers going. Well, so what's interesting is that, you know, as a person who's been in the sneakers for many, many years. My now most cherished sneaker is not a Nike somehow, even though I'm a Nike fanboy and collector, is an artifact sneaker collaboration with a guy named Jeff Staples, who is an amazing New York streetwear designer that it was his first NFT.

And it was a digital sneaker that you could then forge now into a physical. But that digital sneaker that I paid 500 bucks for four months ago, where I was like, I'm feeling this, like, there's something going on here that just tells me this is right. That thing, right this second is worth almost $30,000. Oh, my Lord. It's just insane. So, I mean, obviously, you know, there's certainly a bubble happening right now,

but it's not necessarily a bubble that's going to burst. You know, people are coming into this space in droves. It's really interesting. It's really fun, I think, more than anything. I think it's about community membership. And like, when you think about Yuga Labs as a startup, it's a whole different way. Like, they're never going to have to raise money institutionally or traditionally. They're the whole, their community is funding them.

So it's just different and interesting. It's crazy in that way. When you think about it, you could, and I just had one of these projects on that was doing music. And they raised hundreds of millions of dollars, put it into a project somewhere in southern Central America. nobody knows who's in charge of the project. They all are undisclosed. I mean, I wonder what the tax treatment of this is going to wind up being. When you sell it, it's a capital gains because it's art, I guess.

It gets treated like that. I wonder what the board apes company, Yugo Labs, I guess, yeah, it's not a security because you're not buying equity in the company. You're buying a piece of art. It's really interesting. But the art enables you to do something. Yep. basically your access pass.

Imagine if Soho House had built out like a whole different structure of integrations and events and free things from their partners and stuff like that. It's sort of like that's how I as a, you know, start thinking about it,

not that it's Soho House, but it's sort of just like this club that you can get into and be a part of. And, you know, I think the community element of this can't be, where does it manifest? Where does it manifest in stuff in clubhouse rooms, on Twitter?

Is there like a Slack or something like that where people are hanging out? It's all Discord and Twitter. So the Discord is where each one of these projects has their own Discord. And these things, there's also a bunch of private discords that are for smaller groups that people like-minded who meet on Twitter. But it's really like Twitter is driving a lot of the conversation here. And Discord is where it gets one layer deeper. And there's some really, really heady and interesting things.

going on. Just like any, just like any, you know, thing where everybody and their mother gets involved, there's going to be a lot of bad crap. But there's also some stuff that's really, really, really, really great and interesting. Where's just going? Tell me, what are people talking about? What do they think the future of it is? Because when you have something that captures the imagination like this has, it's going to be a lot of, um, people are going to have a lot of ideas. And you mentioned there could be some downside. So unpack that for me. Upside and downside. I think, look, the downside is that a lot of people lose a lot of money because there are a lot of people who are quote unquote investors now and entrepreneurs putting their money in things, but they don't know how to properly, you know, figure out whether that's a good investment or not. They're just kind of going by what other people say and following these, like there's so much of what they call the pump and dumps where people, you know, just really like all get together to try and drive up the price.

and then it falls to nowhere because there's nothing structurally keeping it up because there's there's you know yeah coordinated insiders who got it early pumping something up and then they're secretly liquidated so that's like there's going to be a lot of people who lose a lot of money that way but if you're strategic and smart like and you find the real entrepreneurs in the space the same way folks like you have found you know other types of businesses in the past as web one to evolved and changed the world right like i think that That's where it's at. And so those people are really pushing the boundaries of how company structures are owned.

And I think that that just incentivizes a whole different form of collaboration between creator and community that we haven't seen before. And I didn't start thinking about. That's something I think is interesting. I look at it and I think, wow, this to me is like this new form of patronage for artists. So I do think that this one is off the rails and probably giving one artist $100 million or hundreds of millions of dollars is probably unnecessary.

But if this was a collection of artists and you thought, gee, people were making great art in the world because I actually, this is one that I find the artwork appealing. Like I would actually put one of these apes on my wall as a piece of art because I think it's kind of funky and cool and it's kind of just pleasing to me aesthetically. But artists had no way to get money

or to build an audience. They were disintermediated through galleries and there were these gatekeepers now, it would be super interesting if somebody could create their own auction house like Christie's that recruited artists and did all this for them or with them. I wonder if anybody's done that startup before. Maybe you and I should quit and do this. It would be an interesting idea, right? Yeah. I mean, look, that's pretty much, there's a lot of that's been going on, not on that level, right? I think Christie's and Sotheby's have smartly gotten involved pretty early to sort of legitimize a lot of what's going on.

But, you know, places like super rare, Nifty Gateway have been curating artists and being a platform to build community around to like pick, handpick and say, hey, these people are great. We think you should know about them. And a lot of people's careers have taken off thanks to, you know, their success they've had on those types of platforms. And one example, just of like some really interesting project that is going on. is a guy named Micah Johnson, who he's a former professional baseball player turned artist who was on the Chicago White Sox. He has a character called Aku.

And he is basically making a movie about Aku. He talks about how it was like, his niece came up to him and was like, can astronauts be black? And the whole concept of what he's doing is building a film and a persona around this character, Aku. and he really believes that like this could be... Oh, wow. So it's been optioned for a film and TV. The black hash or not Aku becomes first NFU. Oh, my God, that's brilliant. So what he's doing is releasing a series of 10 NFTs that are videos, right?

But it's basically your way of supporting his project, right? And so he is funding via community for his movie that he can then go and offer out. This is the new Kickstarter. It just clicked for me. It's genius. Like there's just, there are some really interesting things. So, Jake, Kyle, you should get a ape. You should buy one right now while we're on the show.

You should come in and come and hop and be a part of this thing. And what? I should spend $150,000 on a monkey. What, you got it? Come on. Let's go. No. Give me the next one.

Give me the next one I can buy into. I want to be on the ground floor of the next one. Okay. Just, you got, listen, you're now a friend of the show, Andrew, and you're a foodie, right? And a Nick fan. Well, I would never, I would never, I would never, qualify myself using the F word because we're like, come on, I'm an enthusiast, you know. Okay.

But like, yes, and I'm a huge Knicks fan. All right. So I'm a huge diehard Nick fan for a long time. I actually came out for the playoff games, which was unbelievable. It was like the first. Those were, those were some of the best moments. Truly, like that first game. Have you?

Were you at the car? It was incredible, right? Like to be vaccinated and have no mask and screaming. I'm, in Trey Young is killing me. But we made such great moves. I mean, how excited are you for 33 days from now when we see Knicks playing basketball? basketball. Forney and Kemba and our original crew locked in. I just can't believe and very excited about the fact that we can sit here and be excited about Nick's basketball. It's going to be so,

it's going to be the greatest. I mean, I'm putting us that 44 wins, 44, 45 wins. I think would be 50 or 16. I think we got a shot of getting to the second round. And you got to think Dame and other people are looking at this progressing on, hmm, that's a pretty good squad. playing in New York it's electric All right listen Great to meet you Thanks for educating us

And let's hang soon Maybe when the season starts We'll get a meal And then go catch a nick game Sounds good man All right I'm DM you got the next one You think is gonna be hot

And then I'll buy into it I'll get like 10 FTs or something We can do a little side thing I can give you a whole bunch of things That are interesting Slide into my DMs I got you I'm following you now We're gonna get you on an ape

Get me on the next thing Get me on the next thing Or somebody wants to get me in on the ape thing At a good price let me know All right, talk to soon. Cheers. What would you do with an extra 15 hours every week for a lot of leaders? There's a moment where you realize that you are in your own way. Delegating to someone could be intimidating, especially if you don't know how to do it, right?

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growing your business, and leave the rest of Belay. Just to say, text TWIST to 551-2-3 for your free copy of Rise Up and Lead Well today. Just text Twist to 551-2-3 for your free copy of Rise Up and Lead Well. Okay, and now here is Rachel's interview with Nicole from Harlem VC and how she broke in. Well, thank you so much for coming on today, Nicole. This was really exciting for me. So let me get this straight. You're a senior associate at Harlem Capital and you focus on

deal sourcing, due diligence, and platform development. Is that correct? Yes, that is correct. Yeah, so can you break down for the audience what Harlem VC is and maybe your guys' mission? Sure, sure, and thanks for reaching out and having me on the show. I'm super excited to do this today. So Harlem Capital is a diversity-focused early stage fund. We invest in women and people of color.

And we just started investing out of our fund two of $134 million after wrapping up our fund one of $40 million earlier this year. And so we invest at the siege stage across all sectors. We write checks of about $750K to $2 million for 10% plus ownership. And as a firm, our overall mission is to change the face of entrepreneurship by investing in 1,000 diverse founders over 20. years. And our current count is 40 of that thousand. So we're just getting started. But we are looking for people to join our journey. That's awesome. Well, you got to start somewhere. And it's great that you guys are really being the change. That's incredible, too, that you guys are investing in those groups. I wasn't super aware of the lack of diversity in venture capital until I read the moment of

Lyft by Melinda Gates. And I actually tweeted about it because I was so shocked before coming to this team at launch, I actually did a venture capital fellowship. And all the partners were men. And we did have one person of color as our partner, but we didn't really invest in a ton of women. And there was only one person that I really stuck out to me as being a female founder that I really connected to. And when I read this statistic, it just totally brought into perspective how important it is to have people like you and the whole Harlem team. And the statistic was only 2% of VC partners are women and only 2% of VC money is going to women founded ventures. And it does note that women of color are severely represented amongst even that percentage.

So you guys are killing it. That's really awesome. And I'm super happy that we had somebody on the show that is advocating for those things. So before Harlem VC, what was your journey? Yeah. So my story before Harlem Capital. So I was, I'll take you back to the very beginning. So I was born and raised on Long Island. I spent my entire life there until I moved into New York City to attend Columbia University.

And it was there that I really got to know myself and realized what I was interested in and where I wanted my career to go. And it became actually quite apparent that I was not a reading and writing person. Like my brain did not work that way. I was far more of the numbers in math person. And I, you know, I like to use the analogy that give me a one-page paper. And I would be in the library like all night crying. But if you gave me a 10-page problem set, I would be able, I would be like calm, cool, collected.

And so obviously learning that, I realized I should major in something that caters to me. And I ended up majoring an econ math. And with that major being in New York City, I ended up taking the finance path, right? So my junior summer at Columbia, I interned in investment banking and subsequently signed to join full time. And so I joined post-grad. I joined RBC Capital Markets in the TMT group, Tech Media and Telecom. And I spent four years there, actually, in banking, which was quite a long time. And I went analyst to associate there. And I realized, you know, I liked the work. within finance, but I didn't like the culture or the mission. And so that's sort of what led me right into Harlem Capital. That's awesome. So I definitely feel like there are multiple paths into VC. A lot of people that I know were previous founders or like yourself were in that banking situation.

But for you, I know it's a little bit different, the actual job process. And this is actually how we ended up finding you, which was on Twitter. And I'm going to ask Justin or whoever's editing this video to throw out this screenshot because I think it's incredibly interesting. You posted a tweet of two slideshows and the tweet said, breaking into VC is hard. Finding ways to differentiate yourself is hard. When I was looking to break in, I knew Harlem Capital was where I wanted to be, but how did I do it? I created a presentation showing HCP exactly where I could add value on day one, some snippets below. And then you included those two presentation slides. And I thought that was awesome. Can you talk to me? First off, explain why it's really hard to get a job in VC to the audience.

Yeah. So I, you know, I think it's, so for me, I wanted to break into VC, you know, for a couple of reasons, which I can imagine that some people would relate to this as well. And, you know, coming from a banking background, you know, a lot of people put blinders on, as I like to say, and take the traditional finance path without ever sort of stopping to think what they actually wanted to do. So, you know, they would go investment banking to private equity into business school. And when I was in that position, I wanted to be intentional about my career. I did not want to go into a career that, you know, I wasn't passionate about. And in VC, you know, a lot of people love what they do. They're super passionate, right? Founders are building something that they believe in.

And investors want to fund them, right? And so everyone wakes up wanting to do their job. And, you know, I think in a lot of industries, that's not the case. right and you know especially in banking i mean it's not always the case but i doubt you can most bankers truly love what they do um and so you know for me i came across harlem capital on lincoln um and one of my one of my connections one day randomly liked the announcement of their fund one um close and i remember reading the article and becoming completely obsessed with the firm in the mission. It was like in that moment I realized that's what I wanted to do. It, it,

everything seemed to align for me. Being, you know, doing VC at Harlem Capital married like two things that I was super passionate about, which was finance, which can be quite soulless, unfortunately. And making an impact, investing in diverse founders. So it gave me the best of both worlds. And so, you know, for me, like other people, I think they just, just want to be in an industry that is exciting, right? And VC is the, you know, epitome of exciting. You're building the next big companies, right? You're building the next Uber, Lyft, Slack. And so I think that's probably why it makes it hard, right, for a lot of people to break in, is there's more demand than there is jobs. And so that's my guess as to why, you know,

why it's so difficult to break in. So let me get this straight. Did you see the LinkedIn job posting and then just send them these presentation, or was it something like you slid into someone's DMs and sent him to him? We had the Harlem Capital founder on actually, Henri Pierre Jacques on episode 1183, which was super cool to have on, and that was the first time I heard about Harlem Capital. So did you send him your presentation on Twitter or something?

No, so what ended up happening is after I saw the LinkedIn post and became completely obsessed, I realized that I wanted to be there. And they offer a pretty extensive internship program and fellowship program. And so I started doing tons of research on BC, started doing tons of research about Harlem Capital and reached out to previous interns to see their experience. And I applied for the internship. And I fortunately was able to get into the internship their summer 2020 cohort. And so it was there that I spent 10 weeks doing the internship, and then I went into a 10-week

fellowship with them in the fall of 2020. And what ended up happening is, you know, I realized that I was in love with Harlem Capital and the mission. I truly wanted to be there. And I, during, Harlem Capital does a pretty extensive review process as well, feedback process for their interns. And so we have a mid-term feedback and final feedback. And so for my fellowship, I had been there for, you know, whatever it was, 15 weeks. And I was like, I'm going to create a presentation to show them exactly why they should hire me, prove to them that I am the person that should be in this position. And I decided I was going to send it during my midterm feedback. And so I was like, I sent it to Henri because he was my pairing at the time for the internship or the fellowship rather. And I said,

along with the midterm feedback, I would like to discuss this presentation on why you should hire me full time. So that's how that sort of went down. And I'm happy to go into the presentation more and give the listeners a bit more info on that. Yeah, I guess you have also been kind of noting on different ways to kind of break into VC. And I think that Jason would love to hear more about that as well. what struggles have you seen in the industry in terms of applying and gaining these almost entry-level positions into venture capital? You did mention them in two of your other tweets, breaking into VC tip number three and breaking into VC tip number two. But I'd love to hear more on that as well. So I think VC is a network game, right?

And so the skill that you should have is just learning to network. like the single most important thing is networking. And so I think gaining those entry-level positions is difficult because you're not established within the VC industry. And so within VC, you utilize your community for everything, from sourcing a deal to diligence to port go-go help, to hiring and everything in between. And so the bigger your network is,

the easier being in BC will be and getting a job in BC. And unfortunately, in the early days of your career, you just don't have those networks built out. And, you know, my advice to anybody who wants to get into the industry is, you know, start building that network before you land a job in BC. And probably that networking will get you the entry-level job into VC. But you have to be willing to put the time in. And, you know, I like to say, like, remember, you know, the industry is small. And every interaction is a chance to create a new relationship.

And you have to be intentional about it. And so I think that was probably the hardest thing for me as well, breaking in is. you know, I had the skills to do it, but did I have the right people I can contact? Did I know, you know, who I could go to to diligence a deal or where I could source a deal? And so network. Everything is about networking in community and as, you know, an entry level investor, that's difficult. And so you have to build up sort of that community. It's so funny because in college, you learn how to write a great resume, an awesome cover letter, but there's not an entire class on networking. And honestly, every time I've gotten out of college so far has not been on my

resume or on a CV or anything like that. I agree. It's all about networking. You also mentioned operating like a VC in your tip number two tweet that I saw. What does it mean to operate like a VC? Yeah. So this is interesting. And one way that I think people could stand out in interviews and networking is, you know, people are taking the time, people in VC are taking the time to network with you, which is great. But you need to add some sort of value, right? If you operate like you're in VC already by understanding their investment thesis deals that they like, things that they like to see, you can get on the phone with them, not only ask them questions about VC and themselves, but you can also say, also, here's a company I think you should look at. You know, I've been following it for three months.

I love the founder. Let me send you a bit about it and tell you why I have conviction on this deal, right? And so that's what I mean by operating like you were in VC already, right? If you were in an investing position, you would do that, right? That's how a lot of networking calls go, right? You have a conversation, you talk about the market, you know, you talk about what you're up to, what you're interested in. And then you share some deals, right? And you say, oh, by the way, I know you're a thesis.

And here's who's raising. right? So making sure that you are a part of the industry already is a way that you can just differentiate yourself and adding value to that person, they'll remember you, right? It's just, it's not just another networking call. It's, wow, this person shared a deal that I'm going to take a look at. What are the top skills that you have that you think really help add value to Harlem Capital? Yeah, so I think, you know, every VC needs to be curious, right? Every investor needs to be curious. And I'm an incredibly curious person.

And I'm a people person, right? I love chatting to people. And so I think being curious and being able to network, like I said, add value to any VC firm. And I believe that I have those skills. And so I think I'm able to provide, you know, not only those skills, but a different perspective as well to Harlem Capital. And in my presentation, actually, I was saying to them, you know, I showed them where I thought they had gaps in their firm and how my past experience and my lived experience could fill those gaps. And one of them was that I am Latina and I identify as LGBTQ. And so for me, my perspective on things are different than the rest of the firm.

And not only that I can diversify your sourcing funnel, right, using my network, which is unique to me. And so I think, you know, on top of the traditional skills of being, you know, curious and love networking, you know, bringing my lived experience and how I identify to the table provides a different perspective as well. It's great that you put that in your presentation too because I don't necessarily think those things would have come up in a traditional interview. And especially in interviews like venture capital where I've seen a lot of things like case studies or show us examples of your work. I feel like it's kind of difficult to kind of incorporate your personal life within that process. So that was really cool being able to see that. Do you have any other advice for the audience on hard skills that they should know before they want to break into venture capital? And I know that's really difficult because I feel like venture capital is like a giant umbrella of things.

And you already have given us two awesome things. But is there anything specifically like financial modeling or anything like that that you think would be really beneficial? all? Yeah, so I think it depends, right? Because as you say, VC is broad, right? You know one VC firm is the same in that, you know, you have early stage funds, you have industry agnostic firms, sector specific firms, you know, geographic focused firms. And so what I would say is before you can say the skills that you need to jump into the industry, you need to figure out your niche, right? Are you interested in early stage agnostic firms? Because that skill set is, going to be slightly different than if you wanted to invest in, you know, series B biotech companies, right? And so what I would say is the first step is figuring out where your interests lie. And once you figure that out, then you can cater the skills that you learn. I think from a fundamental level, you know, early stage you don't need as much financial modeling. But if you were to go to that

series B, you need that financial modeling. Right. But what I would say from fundamental standpoint is you need to understand venture math. You need to understand, you know, dilution. You need to understand ownership. You need to understand all of those basic things within BC to be able to understand investments, to see what makes sense, what doesn't make sense, what fits into an investment thesis. And if you don't have those basics, it might be more difficult for you within the industry. I completely agree.

And actually, when I was first interested in venture capital, I got the book from a mentor, The Secrets of Sand Hill, which is about A16Z. But honestly, the book was pretty dense. Didn't read it all. But at the end of the book, there's a glossary. And I used the glossary, kind of like a dictionary for venture capital. So if anybody's listening to this and is really struggling with the acronyms, for us to me, you have to check that out and investipedia.

They were my absolute best friends. It's great that you brought that up. Do you see a big difference between maybe the Gen Z versus millennial investors that are coming into this space? Because I feel like venture capital as of late has really blown up as we've seen. There's been that incredible amount of investments, especially over the past year. Yeah. You're saying is there a difference between Gen Z and millennial investing? Yes.

Yeah. Yeah. I definitely think there is. One thing that I notice is that Gen Z is using social. media a lot more, right? Twitter has blown up in the VC industry and not only, you know, as a way to get yourself known, but also for business advice, for learning more about industries, for all things VC. And I think Gen Z has really captured that within social media. So I'd say that's one thing that I think is different. You know, social media is a strategy,

not, you know, it's not frowned upon. And I think in finance, a lot of people don't like to be in the limelight like that. But, you know, Gen Z has really thought this is a strategy and this will help me grow as a person. And then I think just in general, Gen Z has had a big effect on industries, right? It's a generation that is involved. And so, you know, you look at all the different social apps that are blowing up and everything Gen Z touches, right, is changed. And they just have a different mindset, right? They just have a different life mindset, investing mindset, what they care about is different. And so I think they're just touching every industry. And so it, you know, it's changing the investment landscape. It's funny because as a Gen Z growing up, my parents were like,

don't post too much of your life on the internet. And now that I've kind of switched into this space, or like have opinions on the internet. Like, how do we know what you're interested in or what you stand for if you don't? And I think that's a huge differentiator between, you can always tell when someone maybe isn't that hip with social media or isn't a Gen. Z slash early millennial with how they interact on Twitter. So I think that's definitely a great, a great piece of advice. And even here at this weekend startups, I've helped the team start a TikTok page. And it's been an interesting experience, but it's so important to branch out on that platform, on any platform, especially in terms of kind of creating a consistent pipeline.

Like, why not make your voice heard to get the most amount of people to hear about you? Definitely. I mean, your network is just. 10 times through social media. Right. And like even, even I'm on this podcast because of social media, right? So it,

you know, it just, your reach is extended far more than you could ever imagine through social media. I mean, at Harlem Capital, we did an analysis of our intern pool. And of the 6,000 applications that we've gotten,

10% are international and we don't even do international deals yet. So like, it just goes to show you the power of social media and the reach that you're getting there. Right. So it's, it's incredible. And I think Gen Z has realized that and has really, you know, held on to it. So to kind of close now and to continue the conversation about making your voice heard, especially around the world, their way of social media. I'd love to conclude with your podcast

that I saw, the More Equity podcast from Harlem Capital. I believe you host it, correct? Yes. Yes. That's awesome. Yeah, with Gabby Kazzo on my team. That's so cool. So what are the goals there for that podcast? It's honestly just to, so Harlem Capital's mission is to change the face of entrepreneurship, but in order to change the face of entrepreneurship, we have to change the, we have to change the face of investing as well, right? We need people to invest in things that they identify with. So we need diverse investors. And so like I said, we have six, we have an extensive intern program. We've gotten over 6,000 applications. And we can't give all of those diverse individuals.

a spot at Harlem Capital, but we want to make sure that they are in the VC ecosystem. And they've historically and systemically have been pushed out. And so what we're trying to do is demystify VC, right? Demy the interview process. Get those diverse people in the doors so that we can not only, you know, change the face of entrepreneurship, but change the face of investing. And I think, you know, Harlem Capital, we're growing, but we're, you know, we need help. We can't change the whole ecosystem.

And a small part in doing that is by getting, you know, the diverse candidates that we get in the doors of other VCs. And so that podcast, the goal was for people who are interviewing and don't know where to start, you know, there's a start. Right. And we, you know, you can look at all the resources we cite, get on Twitter. And so that was that was the goal. That's awesome. How many episodes are you in right now? How many podcast episodes have you done so far?

So I don't typically host the more equity podcast. I've done a season with Gabby and Kelly, which are the, where Kelly has left the firm now, but the two senior associates at the firm, I interviewed them, and then I did the demystifying VC. And hopefully we'll be on some more as we roll out new seasons. That's awesome. I cannot wait to listen to that. And I'm also looking forward to re-listening to Jason's talk with the Harlem Capital founder on episode 11883. I'm just going to repeat that again for everybody because it was super awesome to hear about you guys.

Thank you so much for being on. I think this conversation is going to be really beneficial for anybody else looking to break into venture capital, especially with how things have been changing so quickly with the amount of investments increasing and social media really taking over the space. Thank you so much. Is there anywhere people can find? find you, maybe your Instagram handle or your Twitter handle. Yeah.

So if you, you can find me on Twitter at Nick underscore D. Tomasos, that's NIC for Nick. And on LinkedIn. If you are looking to break into BC, I am happy to be an advocate for you. So please, please reach out. Awesome. Thank you so much for being on Nicole.