Transcript: How to Build a Scalable Venture Community | Jennifer Jeronimo CEO of Gaingels Inc
Full transcript: How to Build a Scalable Venture Community | Jennifer Jeronimo CEO of Gaingels Inc.
2025-03-29
Host: My guest today is Jennifer Jeronimo.
Jennifer is the CEO of J Angel, which is a venture farm that invests in early stage companies, have done 70 plus deals with Greencraft, 30 plus with Saquyer, invested in 70 plus unicorns, including companies like Brex, Carter, Masterclass, Remote.
They're a unique venture farm which started as a large investment community with active investors of more than three 3,500.
And our conversation will cover investing in startups, business model of the firm, nuances of new startup investors and what is it like to invest with with them and more.
If this is your first time listening to startup project, don't forget to subscribe to us wherever you listen to the podcast. It helps us reach more interesting audience. Jennifer, welcome to Startup Project. Jennifer: Hi, how are you?
Thank you for having me. Host: Where are you joining us today from? Jennifer: I'm joining you from home in Brooklyn. Uh we do have a an office in New York City in the Flat Iron District, but I figured it'd be good to do this one from home.
Host: Uh am I pronouncing it right, J Angel or Ga Angel? Okay. Um So, I think let's right get let's get into it, right? Uh what is Ja Angel? How does it work? What do you do at Ja Angel? Jennifer: Great.
So, Ga Angels is one of the largest venture capital syndicates. We also have funds as well.
Um so we've deployed about um a little over $900 million into about 2,500 startups through our community of members as you mentioned, now it's over 4,000 accredited investors.
And so, um, our mission is to show the world that equity of access and representation leads to positive returns. And as you would mentioned, how we do that is we invest at scale, which is obviously the 900 million across 2,500 companies with the best.
So we never lead a deal. We co-invest alongside other venture firms and some very large ones as you'd mentioned, we've done over 35 deals with Saya. We've done over 75 with Greycroft through a community that measurably impacts diversity.
And so we have a largely diverse membership and we are providing them with access at an accessible point to deals they wouldn't necessarily have access to.
And so, although our sweet spot is, you know, seed to series B, we are industry and stage agnostic, and so we do also do later later stage companies as well, but that's just a little bit about us.
Host: I think we had Sajid from Mayo VC on the podcast.
He's also a prolific syndicate-based investor, as one of the largest syndicates on Angelist, but he's sort of like a more of a one man show and he's also I think collaborates with a lot of other syndicate groups and you know, co-invest with funds, similar to yours.
But I think you're also seen your syndicate on Angelist and did you sort of grow up as a syndicate on Angelist and sort of went out of Angelist. That's how and now you became bigger than what a typical Angel syndicate would be.
What was that sort of evolution looked like? Jennifer: I think we've always done both, right? Um, I think it initially, right? I think it was it was more on the the Angelist side, probably before I was a glimmer in J Angel's eyes.
But, you know, how they originally started really was an investment club, investing in LGBT investors, investing into LGBTQ founders.
And then in 2019, they realized that we were talking in our own echo chamber and we really in order to make an impact, we had to sort of one, open it up to all diversity and to also work with portfolio companies that may not be diverse, but helping them get there.
So it was always important, you know, back to your question, to do things both on our own paper as well as like on.
Host: of for, you know, in investing groups in general, strength is on the LP side, you know, you have you have to have large community. On the other side, you have to have lot of good deal so.
Uh for you, what are the different sources of deal flow uh, you know, for the you making investments? Jennifer: resources. Yeah. So, um, it's really our our community, right? And it's our community of investors, VC partners, portfolio companies.
So I'll talk about each of them. So we have over 4,000 accredited um investor members and sometimes they will come to us and say, you know, this is my my company and we'd love to see Ga Angels on that cap table.
You know, a big points of sourcing really is the relationships that my partner has partners have built both with portfolio companies and VC partners.
So, you know, two of our founders, Paul Grossinger and Lorenzo Tione, right? have a tremendous network both in the startup community as well in the venture community.
And so they've they've built that network to a point where they can ascertain and get access to great deal flow, as well as sort of some of those bigger deal partners like the Sequoias and Grey Crofts. And then of course, we're well known, right?
So in Q2 of just last year, we were number one in the world, number two based off of what pitchbook says, right? in deal flow, right? So we're fairly well known.
The portfolio companies who want to at least prioritize diverse check writers reach out often as well. And so it's it's a little bit of a hodgepodge of all.
Host: There's sometimes this friction, you know, when you're participating a seed or seed say to get allocation. Uh how do you make sure that you're getting allocation in right deals?
Because I've faced this as an Angel investor when investing in pre-seed and then by the time you get to the seed, Angel investors don't get that much allocation. sort of do pro rata even though you might have pro rata rights.
And I've seen similar thing happened with, you know, when you have syndicates which have done pre-seed and now they want to seed.
Um, like do you face that challenge with some of the deals that you want to invest in or uh, because of your size and you know, track record, it's not as much of an issue for you? Jennifer: I I think it's more of the the ladder, right?
Our size and track record. Most times portfolio companies will come back out to us and tell us about a new raise or when they send us updates, they'll tell us about a new raise and we'll come back out and start having those discussions.
I mean, for a portfolio of 2,500 companies, I'm sure it's happened to us, you know, at times where maybe we didn't get that access, but we're also a pretty well-oiled machine.
So my organization is reaching out and trying to keep their ear to the floor on follow on rounds and things of that nature. We look at all of the updates we receive to see if there's additional fundraising.
And so I think, and you know, we're not competitors where we cooperate, right? We co-invest alongside.
So I don't, you know, funds don't really see us as a competitor, they see us as adding value to helping portfolio companies as I mentioned earlier, who want to um ensure that they're giving a piece of their allocation to diverse check writers.
So we don't typically see that issue, but again, I'm sure, you know, with a portfolio as big as ours, it's happened, you know, from time to time. Host: You mentioned well oiled machine, right?
Um, I think you're sort of like one of the few syndicates because most syndicates are on by individuals and like not a group of people although like not sort of involving that man and you're probably at the top of there where you have sort of brought a structure to it.
Talk to me about what is the structure like? How many people are working actively full-time and who's doing what? Jennifer: Yeah. So just like any other I mean you know, we're 40% 40-ish person organization, structured like most companies.
I think one of the reasons why they why the founders brought me in was because, you know, I had deep corporate experience, right? And I ran lots of different business units and and companies. I mean not companies, but a departments large and small.
Um so it's, you know, we have a compliance program, an HR area, a finance team, an ops team, a community team, very similar to what you would see in a larger organization.
Um and then we manage it the same way, you know, through metrics, through priorities, through outcomes, right? Um, and so through having the right controls in place.
And where we feel like we have weaknesses or maybe soft spots, we may bring in or not maybe not the full expertise, we'll bring in like an outside vendor.
So like for example, we use I have somebody that runs my compliance program at Ga Angels, but we also have an external outsourcing compliance organization that we also use that we liaise with.
And that helps me extend extend the breath and reach of of my team in a lot of ways.
Host: So, in terms of like when a deal comes to you, what is the process of like, you know, you're looking at it and evaluating it to sort of getting it through the finish line? Jennifer: Yeah. So we look at it just as any typical VC would.
You know, we look at a bunch of things, right? One of the first and most important is just the deal lead, right? Because that is our sweet spot. We don't lead, we co-invest alongside.
So the stronger the lead, that that gives us more confidence, right? But as any VC, you know, and it depends on the stage as to how deep your due diligence is.
Obviously earlier stage companies, you know, you don't have a lot to go on other than the team and the problem that they're solving and your your conviction on whether in that whether or not that's something people would be interested in.
And as you as the company gets a little bit later stage, you start looking at things and again, any VC will tell you, they're going to look at the team and the experience of the team, the grit of the team, how well they know that team.
Are they exited founders, serial entrepreneurs, or have they been in that space at bigger companies where they can bring in that that level of expertise.
We look at, you know, the traction of the company, if this is a follow on round, where were they and where are they now? How are they against the projections they've made?
Are they are they growing at the levels that they said they would when we first invested? Or if this is the first time we're investing, you know, what is the traction? What is their growth month over month, year over year, things of that nature.
We obviously look at the problem, you know, is this a problem that we think needs to be solved in this world? And, you know, what industry is it in? We are a syndicate, is this an industry that excites my members, you know?
Is this something that they really like and and will I know will like.
There are plenty of times that we as as, you know, partners and deal sources, you know, um, love a deal and we think it's great and we're a little surprised that maybe, you know, our membership does isn't as excited as we thought they would be.
So we look at the industry, is that an industry that my membership likes? And so those are just some a few of the things that that we look at to assess a deal. We'll also share it with our partners, right?
Because, you know, if you if you've got other venture partners who are really excited about the deal, that makes us feel a lot more comfortable like that we're not being too myopic about it and and, you know, that we're we're getting outside opinions.
We may even talk to to our members. You know, if I'm looking at a cybersecurity company, um, I will I have a few members that I reach out to that I go, you know, I love this. I but how big of a problem really is this?
This is what they're telling me, but is there things I should be thinking about? So there there's a a host of things that we look at in order to make the assessment.
And then it's really syndicating it to our members and seeing it if it's something that they're interested in. Host: So, uh, I think one of your strengths as an investment community is the community, right?
Uh, I think like if I think about because at this point I'm close to doing 100 episodes. I think at least I've talked to 40 to 50 investors on the podcast and offline.
So I think I've sort of seen all the models possible to become a new investor and one of the really successful models is if you are able to create a unique network of a unique, I would say professional network.
And a great example of that is obviously you guys have created a unique network focusing on diversity and there's another sort of fund which did the same which is like they've created a community of product managers.
So there's this VC from called Mighty Capital which we have featured a couple of episodes back.
Um it's also run by another female uh female managing partner and and an author. and she created this amazing nonprofit product management community and they discovered products from the community and invested in them.
And that's why they were their hit rate when you see versus the rest of the venture is much higher. Their ability to pick unicorns is, you know, way beyond than an average fund.
So, I think you also have that advantage and I've seen a couple of other examples where sort of community becomes the core strength and and I recently had David Blomberg, which uh an episode that will come out soon. and they have this unique CXO community. and that was the reason why they invested in this company called Nutanix, which is now a $16 billion dollar company in public markets, but their core thesis of whether or not this product will be bought by CXO CIOs is because they tested it out within their community.
So what you're talking about, you know, your own community makes sense to me in terms of like differentiation, identifying trends, you know, picking great products. and also probably the community itself also creates new fund managers in a way.
I'm sure some of the members from your community went on to create their own funds. I'm guessing and you can tell me if I'm wrong. Have any of the community members went on to create their own funds, syndicates and networks?
Jennifer: Well what I'd say and and I was just on a panel a few weeks ago, or maybe it's a couple months now, but where it was a a women's panel, right? And someone said, how can I break into venture?
It's it's sort of, you know, it's really where my interests lie. And one of the other panelists who I know, you know, at an arms length, I I've met her a couple of times had actually said, you know, track record is everything, right?
And well, to get into venture, it's a couple of things, right? It's a network. You know plenty of people have gotten in through their network. You also have, you know, when I hear people's stories of getting into venture, they're so unique.
It's there's not this like cookie cutter way that, you know, I who come from banking, you know, where there's like this traditional like structure of this is how you get in.
And so when we were on the panel, um, that was the question is how do I break in?
And and not me, but one of the other panelists had said, you know, if you don't have a track record and you don't have experience, what you could do is take whatever your budget is, go onto a platform like Angels that has tremendous access, pick your companies and then create your own mini portfolio that can then you can then put to people later when you're talking about breaking into the industry.
And I think that's that's one way and I've heard people doing that. And you know, we also have a lot of like venture partners that are on my platform, right? That just like my deal flow.
And they want to collaborate with us, you know, I'll say probably a couple of times we're collaborative, not competitive.
And so sharing in deal flow so that when I share deal flow with them, they share deal flow with me, that just that just expands my deal flow. So, no, you can definitely use sort of the Ga Angels platform and the the actual the access.
I mean at any given deal I'm running, one to five companies a week, right? And there's plenty to choose from across all industries, stages, etc. Host: Talk to me a little bit more about the venture partners.
Are they like part of the community that's leading the deals or what are they doing exactly? Jennifer: Sometimes they're the leads, sometimes they're co-investors like we are and we introduce deals to one another.
Again, um so that you can, you know, it only helps both sides of it.
Host: So they're part of the deal that's happening on your platform or they are also investing and then they bring the deal into your platform so other people can invest and it's a combination of that. Jennifer: Yes, that's right.
Host: And if like a venture partner brings in a deal, like are they getting carry or from the transaction or how are the venture partners compensated for their due diligence or dealer?
Jennifer: It really depends on the venture partner, what is the level of like, you know, how often is it, you know, we are, you know, we we may share carry.
In some cases we just want to help a portfolio company raise as much money as they can and we may just go here, you know, and I'm not going to go, okay, you know, let's put us a a carry agreement and let's split carry.
Like, no, we're we're here to help the innovation economy. And so it really is on a case-by-case basis and it's dependent on what each of the what the two partners want as an overall outcome.
Host: And one of the uh trends that I've noticed um in syndicates um is, you know, I think sort of in 2022 end of 2022, we sort of saw a correction where it has become really hard to close deals.
And this always I think a little bit cyclical in nature where, um, you know, the appetite for investing in startups suddenly goes through the roof, which I think probably we've seen in 2020, 2021. and then on all of a sudden it fell through the Cliff and it was very hard to close a deal and I've talked to many of my, you know, syndicate lead friends and I've tried to do a couple of deals which were really hard to close even that the company quality is really high. are you seeing the same trend and um a follow up would be like is it picking up back now um compared to like a couple of years?
Like what what is your vantage point looking at? Jennifer: So, I mean, listen, we all felt you know, I think all VCs for the most part felt the bottom come out a little bit on the, you know, this on the second half of 2022.
Ga Angels is lucky in the sense that we've ear we'd already had an established brand. We already had a lot of scale and so it it, you know, we just lowered the amount of deals that we we ended up running.
And did we and I mentioned earlier, there were a couple of deals that we thought were going to be stellar and we, you know, we eat out the close or maybe we had to pass because we just didn't have enough interest.
But, you know, luckily we were sort of in a certain level of maturity in our organization that we could withstand that. where sort of earlier newer VCs might might have struggled a little bit more.
The unfortunate thing about it all is, um, you know, when valuations go down, that's when you really need to when you should be looking at venture, right? People, people get excited about companies and this this is true for the stock market, right?
When the price is low, that's when you should be buying, but that's when people are most scared, right?
And the thing about venture and I don't have to tell you this, but you know, it's a long, you know, you're you're you don't have liquidity. you know, you're you're talking five to 10 years or seven to 10 years really, maybe a little less when you're dealing with later stage, right?
So you're going to ride out that market, you know, hopefully. I mean, I no one can see into the future and and and that. Have I seen an uptick recently?
I want to be cautiously optimistic, but yes, it has been a sort of really as far as member interest on deals, I think people have um a little bit of a renewed interest and we've seen an uptick.
If that's, you know, going to be sustained throughout the course of the year and you know, that would be great. And if it's not, you know, we'll be okay as well. But yeah, and I and I am.
I'm cautiously optimistic, but I'm not an advisor uh of an investment advisor and that's my own personal opinion and that's just, you know, what I'm seeing just through from the Angel's lens.
Host: That's just this concept of, you know, uh diversification.fication can be looked at in different angles. Uh you're investing in public stocks, you can diversify across or you can just buy S&P which diversify everything.
Then you can diversify even further and say I want to invest in public stocks, real estate and private stocks. That's another way of diversification.
But uh when you're investing in venture, the diversification you have to look at is uh through the lens of time.
You have to also invest diversify your portfolio across time because you might not you you don't want to end up in a year, you're making, you're building the entire 25 company portfolio that you want to build, um in two years where the market is extremely high or extremely low.
So, you want to sort of diversify that in a way that you're not catching all the high valuation companies at all the wrong times. That's right.
So, having a disciplined approach to build diversification, not just across like, um, you know, asset classes, but across time is very important in venture. and that's why you see this whole argument that the funds which have raised think end of 2020 or 2021 which have raised at really high valuations might be sort of like the some of the worst class of funds that have ever raised.
Um and we'll see obviously it will take a couple of years to actually play out because as you said, you know, any signal comes only after like six years.
Um and I think if you're focusing on that asset class like investing in startups as an asset class, I always tell, you know, friends who are looking into it or anyone who asks my advice to always diversify across time because you get excited suddenly and you do a lot of investments and you suddenly are not excited and then you're not doing any investments.
Um and before that, this is step two. The step one is actually when you're getting in, get into it to actually build a portfolio of 20 to 25 companies because otherwise the chances are against you of not working.
And if it doesn't work, you'll never come back to this asset class. So that that's sort of like my view on how you look at early stage investing.
I'm sure like a lot of new first-time investors or people who have not done early stage investing might reach out to you or like J Angel, you know, your community. are there like tips and tricks that you've learned from your experience that are dos and don'ts?
Jennifer: Listen, I don't want to say dos and don'ts, but I think a lot of what you said really resonates, you know, a couple of things that I always say is diversification like to your point and anything is is super important whether it's stocks or or um, you know, the public markets or the private markets.
And when you think about that, that could be industry, that could be stage. You also have to look at when you want liquidity, right? And what is your risk appetite, you know?
If you've got a higher risk appetite and want higher returns, you may tend to be a little bit earlier stage, but again, you still should probably have later stage um companies in your portfolio as well as companies across industries.
And and the really and you said something that I just want to double click on for a second is, you know, um it's it's not only um, you know, time and stage, but like, you know, you want to get into things not when it's, you know, when it's already hot and everything is at its height.
So it's it's also there is a little bit of a sweet spot if if folks can get good at like seeing the trends. There are times where trends are only in the private market because they haven't made it to the public market and getting in early.
So you think about quantum computing 15 years ago, right? there was really no public space. The only place you would see that would be in the sort of the private equity sphere, right?
And so I share a lot of your views as well, diversification across, you know, not only your industries, but also across stages and that will get you sort of the time. Your later stage obviously, you expect it to be sooner than your earlier stage.
But you also have to balance your risk profile. Host: Um so, um, you know, you started as a community, you know, evolved out of Angelist, you have your own platform, you're also thinking about, you know, funds or already have funds.
Uh what is like next five to 10 years for, you know, the company look like? Jennifer: So, I think it's it's definitely continuing to grow our community. I I don't think we want to be a big huge venture capital firm that um that is leading.
Could that change in a couple of years? Uh you know, of course, you know, never say never. I for us, it's really, you know, continuing to deploy the capital across, you know, innovative companies that are solving great problems.
To maintain sort of the, you know, a lot of people think either we only invest in diverse companies, we only have diverse members and that's not, but that's not the case, right? We're all about inclusivity.
So making but but I still want to look at those demographics and making sure because part of why we exist is to help democratize venture.
So as we grow, continuing to ensure that we, you know, we have diverse members, that we're helping add value, educating diverse members so that they can not only get a like not only feel comfortable in making an investment, but making smarter investment choices, not just throwing deals at them, but actually providing them with education and resources and things of that nature.
So I think really our long-term vision is to be the most recognizable firm to show that equity of access and representation can lead to outsized returns. Being able to prove that point, right?
Host: We are almost at the end of our conversation and I ask all my guests uh a couple of quick questions at the end. So, the first question is, what are you consuming right now? It can be books, audio, video, anything for work or pleasure?
Jennifer: Yeah, so pod I love the diary of a CEO. I'm not that big into podcast. I'm more of a reader, but the book that I just I literally just finished yesterday that like I'm obsessed with a little bit is the New Earth by Eart Toll.
And so I I should preface this by saying I try to work on myself as a whole person because I believe that when you work on yourself as a whole person, you are better at everything you you're a better I'm a better CEO, I'm a better mother, I'm a better wife, I'm a better friend, right?
And so, you know, Eart Toll's New Earth really talks about there's really no good or bad. it just is, right? And really just not you know, not worrying, worrying is doesn't serve anyone, right?
You take your problem, you look at it and you go, what are the things I need to do and you get laser focused on just how do I solve it? You don't spend too much time thinking about the the past.
You don't I mean you do enough to go, this is these are the my lessons learns, but you don't, you know, spiral and and you're not so concerned about the future, but you're living in the present and doing everything you want to get you to your ultimate goals.
So that's Great great advice. that's my latest. Host: What who are your mentors who helped you in your career? Jennifer: So, I have a lot, right? You know, mentors I think has been, you know, how I've built my career.
And so, you know, I started my career really on the public side in banking. And so I've had, you know, when I first started out, right? I often times was the only woman in the room.
And so I had lots of male ally managers and senior managers like, you know, John Callaham, my Nerva, Brian Goldman.
These are folks known in the spaces that they're in, but they're also really great advocates for women and and for just strong talent regardless of, you know, their gender, ethnicity, etc.
I also when Bear Sterns got taken over by JP Morgan, JP Morgan does a really great job of women executives.
And so there was a lot of women in at JP Morgan that wrapped their arms around me and said, you know what, we're going to support you and we're going to help you get to the next level of your career and that's like Mary Amrett and Caroline Cain and Neimav Elvolu are just a couple of names.
And then when I got into venture, the one thing that I will say that was probably one of the most pleasantly surprising things that I faced was you hear a lot about venture it being a network, it's who you know, but I have to say the women in venture have been so supportive that when I got in and then some women found out that Angels had hired a woman CEO, they reached out and were like, how can we help you?
How can we support you? I think of, you know, Marissa Hoton and Megan McKenna and Amber Kaplan and some very senior uh women in venture who without even knowing me, like reached out and said, welcome to the community. How can we help you succeed?
Host: What do you know about investing that you wish you knew when you got started? Jennifer: It's a really good question. I think it's I think a little bit of diversification.
I also think and I I kind of learned this right away working, you know, at Angel and and looking at, you know, and looking at venture, but, you know, venture is a numbers game, right? You even look at some of the best funds, right?
You know, 20% of their investments may hit big and may have, you know, tremendous multiples. You know, another 20% may be either a little up, a little down or flat and then you kind of expect the rest to die, right?
And those are some of the best funds. And so I think it's important to not put all your eggs in one basket and to take your budget, divide it by however many investments. Uh I like the 12 to 18 investments over like a two-year period.
And so that is something that I'm glad I learned early on in venture investing.
Um, because I've seen a lot of people go all in on one company and and then lose it because that company goes under and and again, I think it's, you know, the power law and ventures is is a bit of a numbers game.
Host: I think that's a good note to end the conversation at. Um thanks Jennifer, thanks for coming on the show, sharing all about your community and investing and startups. Yeah, thanks again. Jennifer: Thank you for having me. I really appreciate it.
Have a great one.