[Bonus] Jack Greco (ACV Auctions) — building a multi-billion-dollar company in Buffalo, NY

Jeffrey Stern [00:01:32]:

Let's discover what people are building in the Greater Cleveland community. We are telling the stories of Northeast Ohio's entrepreneurs, builders, and those supporting them. Welcome to the Lay of the Land podcast where we are exploring what people are building in Cleveland and throughout Northeast Ohio. I am your host, Jeffrey Stern. And today, contradicting my prior sentence in its entirety, we are going to do something a little bit different and hear from an entrepreneur outside of our approximate Region who I believe warrants this deviation from our norm and from whom there is a lot to learn. Today, I had the true pleasure of speaking with Jack Greco, The cofounder and former CFO and COO of ACV Auctions, a Buffalo based wholesale online marketplace for cars, Which went public in 2021 and is currently valued at approximately $3,000,000,000. Now an active angel And venture investor through his fund Far Out Ventures. Jack runs a weekly newsletter called Buffalo Bridge, which tells the stories of Buffalo startup community And has made nearly 200 investments in other founders and startups.

Jeffrey Stern [00:02:45]:

I'll just say this was an awesome conversation that I think will resonate broadly. Outside of the Cleveland Buffalo parallels, Jack is unfettered and candid on his reflections building ACV Auctions, his passion for investing and for founders and the work he is excited about next. So please enjoy my conversation with Jack Greco after a brief message from our sponsor. Lay of the Land is brought to you by Impact Architects and by 90. As we share the stories of Entrepreneurs building incredible organizations in Cleveland and throughout Northeast Ohio, Impact Architects has helped hundreds of those leaders, many of whom we have heard from as guests On this very podcast, realize their own visions and build these great organizations. I believe in Impact Architects and the people behind it so much that I have Actually, join them personally in their mission to help leaders gain focus, align together, and thrive by doing what they love. If you 2 are trying to build great, Impact Architects is offering to sit down with you for a free consultation or provide a free trial through 90, the software platform that helps teams build great companies. If you are interested in learning more about partnering with Impact Architects or by leveraging 90 to power your own business, please go to I a dot lay of the land dot f m.

Jeffrey Stern [00:04:00]:

The link will also be in our show notes. So I I do have to to confess. I I have a a kind of business crush, I'll I'll call it, on on ACV Auctions. And I I thought a lot about, you know, what You guys were able to achieve as as a business because I found a lot of inspirational parallels in your story. So if you'll indulge some fanboyism for for a moment. Totally, man. I I thought it's like pretty easy to loud ACV on just growth alone. Like when you think about how long it took some of the most prominent companies of the last decade to hit a $100,000,000 run rate of revenue.

Jeffrey Stern [00:04:42]:

You know, Shopify, Twilio, HubSpot. You're talking, you know, 5, 6, 7 years, and ACV gets to a 100,000,000, I think at about like 3 years.

Jack Greco (ACV Auctions & Far Out Ventures) [00:04:51]:

Yeah. Well, I mean, look, it's all about slopes and plateaus. Right? And it's made your slopes be up and your plateaus be shorter. Like ACV did start in a plateau in the beginning. I mean, don't get me wrong. Right? Like, we we incorporated the company and had been working on tech for a while, but like when we launched, like we had revenue day 1. And also remember we're a marketplace, right? So, you know, with any marketplace, you know, and I do mostly, I really enjoy investing in marketplaces. It's not mostly what I do.

Jack Greco (ACV Auctions & Far Out Ventures) [00:05:22]:

It's not the only thing I do. It's what I'm known for and I enjoy it and I understand it. But, you know, I always tell people like, you know, it's always tough comparing marketplace businesses to the SaaS business because like, is it obviously GMV doesn't equate to SaaS revenue. But like net revenue is also a little bit like a kick in the pants. Like, you know, like, Hey, why are we like, you know, sure. There's a bunch of things associated with this, you know, but, like, why are we taking such a dip? Because, like, ACV was only clipping, like, 3%, you know, like, a net take rate. But I'll tell you when we started growing from, like, when we took money from Bessemer, which is when things really started shooting, Oh, it was pretty quick. It really was.

Jack Greco (ACV Auctions & Far Out Ventures) [00:06:05]:

And look, I mean, it was, it was a massive market. It was a pretty simple product. I mean, we weren't doing anything, you know, revolutionary. Right. We were like, Hey, are you sick of not having, like not having to go somewhere to buy cars and not having all the information upfront, like, all right, we fixed those 2 problems. And honestly, it was it was the information upfront. Like we went out and inspected the cars and told everybody what they were. So instead of a 100 people looking at 1 car making their own assessment, we sent 1 person out they did probably 10 times the work and showed it to all 100 people.

Jack Greco (ACV Auctions & Far Out Ventures) [00:06:43]:

Actually, because it was so easy, maybe 200 or 300 or 500 would look at it. So, like Right. You know, it was simple. So Well,

Jeffrey Stern [00:06:50]:

and that's the the other front where I I really admire ACV and what you guys did at a deeper level, because in my own entrepreneurial journey, there's been kind of 2 fronts That that I think are related here. And one has been building trust in classically underserved markets that are ripe for disruption as a consequence of their, you know, fragmented, opaque, inefficient, antiquated, I could the list of adjectives goes on, but like often paper based old school infrastructure and like somewhat misaligned stakeholders, And they suffer deeply from this lack of trust. And for me, those worlds have been healthcare and government. But the other piece of it being that, you know, this was a company built in Buffalo, you know, not in a city of startup gravity, like San Francisco, New York City. And I think akin to Cleveland in a lot of those ways. And so those, I think we're both quite inspirational for, for Fermi as an

Jack Greco (ACV Auctions & Far Out Ventures) [00:07:49]:

observer. But so think of it like this, right? ACV had to be born in a place like Buffalo. Now I I've been part of the founding of a couple other things. One was a marketplace called the lumber exchange, which think of a lot of the same aspects of ACV, but for hardwood lumber. And I was an early I was the 1st investor and really involved in a company up in Toronto called Octo, which was auctioning off capital equipment. Think of, like, metal shredding machines and robotic arms and, like, stuff that you would use to manufacture. And, like, what's common across all these things. Right? Like, the things are big.

Jack Greco (ACV Auctions & Far Out Ventures) [00:08:31]:

The things take up space. A car, a crate of lumber manufacturing line. Like, that's not stuff you find that's not resident and ambient in places like San Francisco and New York. Like, it's just not. It's just not there. You know? It's funny, like, even today, if you look at ACV's, you know, manifest destiny, their covering of the continental United States, there's, like, noticeable naval holes around, especially Manhattan. Right? Because guess what? No one buys a car in Manhattan. And if you do, it's some kind of super transformer robot car that's never gonna be on ACV anyways.

Jack Greco (ACV Auctions & Far Out Ventures) [00:09:05]:

Right? Right. So, like, it had to come from here. And I actually think one of the reasons, like, cool things about, you know, the I don't have 4 sports teams in my city cities, which is what I like think of a math, right? You're a 3, we're a 2 is, you know, there is enough space to be able to get early adoption. And you're also able to like activate a market and kind of go under the radar a little bit. So like structurally, like, yeah, we're, we're working with cars. So we happen to all start this in Buffalo, which was a beautiful test market. Right? 1,200,000 people in the Greater Buffalo area. Reasonable income, you know, kind of traditional classic Americans were like life hasn't changed a ton.

Jack Greco (ACV Auctions & Far Out Ventures) [00:09:50]:

So, you kind of know what you're dealing with. And we're working with really big products, right? I mean, like, you know, had we done this in a place like New York, where like all of a sudden we have issues with like transporting this because we're moving it through, you know, bridges and tunnels and across straight lines and stuff. Or in a place where we just couldn't get to people. Like I think these are the advantages of doing something in what I call unapologetically and proudly tier 2 ecosystems. Right? Like, I'm proud to be I'm proud that Buffalo is a tier 2 ecosystem. I don't want it to be New York. I don't want it to be San Francisco. I'm not interested in being Boston or Miami or Dallas.

Jack Greco (ACV Auctions & Far Out Ventures) [00:10:27]:

Like, I don't wanna be any of those. You know, I'm happy it's a place where you're you know, people describe Buffalo as 1 big living room. And, like, you're always a couple degrees of separation in a place that's we're known as the City of Good Neighbors. Right? Like, 1 1 or 2 degrees of separation from being able to get something up and started. I it's one of the reasons like, I don't just like invest and work and live in Buffalo. ACV is public. I could live on anywhere on the planet earth and possibly some, you know, low orbiting satellites and asteroids too. Right.

Jack Greco (ACV Auctions & Far Out Ventures) [00:11:00]:

But I choose to live here because, you know, and I choose, I would even say I choose to invest here because it's more on the investment side. I live here because I have family here. I like to invest in these ecosystems because I think they create the best platforms for early launch, early detection, you know, fail quick or invest quick type stuff. And I think we were able to really hit product market fit. Like the reason ACV grew so fast as we raised 400 and something million bucks. I mean, like, I don't care how small the engine is. When you dump gasoline in it, the car goes faster as long as the engine doesn't blow up. And I would say that we kind of were able to do that, not completely under the radar, but we were able to do that effectively and pretty efficiently.

Jack Greco (ACV Auctions & Far Out Ventures) [00:11:43]:

And we just happened to do it here. I mean, we were it's not like we thought, Oh, this is where we're going to go in the country to do this. We all had family ties to Buffalo, and that's why we did it here.

Jeffrey Stern [00:11:54]:

Right. And just even hearing you talk about it there, there is this, I think, undeniable kindred shared ethos That that Cleveland embodies as well. And I imagine a lot of these Midwestern cities, even though Buffalo is in New York, it's it's really the Midwest.

Jack Greco (ACV Auctions & Far Out Ventures) [00:12:09]:

Not look. I mean, like, there's like, let me put it this way. Buffalo, I don't think has swayed a state vote

Jeffrey Stern [00:12:16]:

in about the last 80 years.

Jack Greco (ACV Auctions & Far Out Ventures) [00:12:18]:

Okay? And we're technically the 2nd biggest region in the state. Right? There's like New York and Long Island, and then you could literally chip that off. And then upstate New York looks a lot more like Wisconsin than it does downstate. Right? You know? We're Ohio. It's the same. I mean, you guys are interesting because you have Cleveland, Columbus, Cincinnati. I don't even know any other probably 12 other cities with the name start with C. You're very, you know, a lot of alliteration there.

Jack Greco (ACV Auctions & Far Out Ventures) [00:12:49]:

Some marketing guy probably one that settled it, you know. And so there is like, you do have some breakup there, right? Like, you know, I was born just outside Rochester. I was born between Rochester and Syracuse. I live in Buffalo. Albany'sthank God they got the capital or they want to be a city, you know, no, no diss on anybody from Albany. But, you know, it's like we have these, like, norm like, cities all kinda look like each other. And then we have New York, which is just totally different. So it is a little different than you, but we are, I mean, we feel that, like, in addition to, like, we don't get any respect because we're a small city, we also don't get any respect because we're literally in the state with the most powerful city in the United States.

Jack Greco (ACV Auctions & Far Out Ventures) [00:13:29]:

Right? Like, it's just we're constantly, like, the nephew that you see in the family photo, but, like, you forget was there. Like, oh, Buffalo was there too. Right? Like, whatever. There's that a for you some opportunity is probably a good way to put it.

Jeffrey Stern [00:13:43]:

Yeah. Did did you always know, you know, growing up in in Rochester and upstate New York Around Buffalo that you wanted to build

Jack Greco (ACV Auctions & Far Out Ventures) [00:13:51]:

stuff? Yeah. I mean, so my father was an antique dealer, which I knew I wanted to run a business because I saw what he did, and he liked to take things apart. He was an antique dealer, right? Like when they were he would buy and I would go with him. Right? Because typical son, you know, oldest son of a entrepreneur, like, 2 thirds of the time I spent with my dad, he was working. And so you pick up the trade. Probably like my son is with me now. If we were doing this call a couple hours later, you'd see him drawing and probably chirping and stuff in the background too because I bring him to stuff. But my father found a way to make money putting things, you know, things that were being taken out of some place, putting him in something else, some other place where somebody valued it.

Jack Greco (ACV Auctions & Far Out Ventures) [00:14:37]:

So in some ways, there was, like, a disassembly aspect of what he did. And like any oldest son with Catholic guilt, you want to make sure you right the wrongs of your ancestors. I'm like, well, maybe I should maybe I'm meant to, like, put things back together. Right? So reassembly, construction, building, you know, when everybody wanted to be something as a kid, I wanna be an architect. And when I realized they weren't putting up, you know, castles anymore, I kinda lost interest in that. But I always like building. I did. But I the thing is I like people and you can even see it.

Jack Greco (ACV Auctions & Far Out Ventures) [00:15:09]:

Like I invest in companies that don't shy away from being labor intensive. Now labor intensive, albeit as long as they can still show proper unit economics and, you know, contribution margin. Right? I'm an economist and a financier first, but I like people. And the cool thing, like when you're an adult, like you don't have, you know, kindergarten class to show up and be with bunch of people and do stuff all day. And I was like, well, the cool thing about businesses are that they're assemblies of people, all learning, all growing, albeit they have more of a common interest than you did when you were in school. And I think I just like the social aspect to it, which obviously during COVID made things super weird because all of a sudden, I was, like, left to my own means and almost demise just being cooped up at my house by myself. But I knew I always wanted to be around people and like help, you know, I just liked helping people with what they were doing. And that's kind of, you know, a lot of people helped me and my co founders with ACV.

Jack Greco (ACV Auctions & Far Out Ventures) [00:16:09]:

And since then, I'm like, All right. I got a lot of repaying to do. And that's kind of what I've been up to.

Jeffrey Stern [00:16:15]:

Well, I do wanna just ask, you know, point blank, going back to the the concept of building trust, in in a digital Context, you know, especially in a space where I think wholesale used car buyers may even pride themselves to a certain degree on their ability to assess a risk. You have the the classic econ 101 lemon examples and Yep. When sellers don't get the best price that they could. And so you built this this efficient market where all the buyers and sellers can transact in a much broader market, all without physically, you know, dealing with the, the auction space. You know, how is it that you actually do that? How do you build trust in, in that kind of way?

Jack Greco (ACV Auctions & Far Out Ventures) [00:17:00]:

Doctor. All right. So look, I mean, if anybody listening, listening to this closes their eyes and thinks, use car dealer. What's the first thing that comes to your mind? Like, name an animal. It's going to be like a rat or like a cockroach something like a, like a slug or a snake or something. Right? Like, so there's an inherent distrust. I have never bought a car from a used car dealer. Like, I never have.

Jack Greco (ACV Auctions & Far Out Ventures) [00:17:26]:

And I could have told you the day we started ACV. I'm like, You can't trust them. Right? You know, they're squirrelly. Right? They're out to get you. So we said, okay. And look, one of my co founders was a used car dealer, and Joe's a good guy. He'll laugh. I mean, I would say this right in front of him, and like it would be moments after he said, you know, he was, you know, started a car dealership, basically went to 16.

Jack Greco (ACV Auctions & Far Out Ventures) [00:17:50]:

But so the way you do that is you look at it from a different outside perspective. Right? You decouple the situation. Dealers don't trust other dealers. Right? Just to be clear, ACV is a b to b marketplace. So as much as me with my place. So as much as me with my retail mindset, think about this stuff, ACV didn't affect that. So you got to unhinge it, right? You have to break it and you have to say, okay, you guys have been, you know, working together as a, you know, a necessary evil for a while, we're going to step in. And I think that, you know, the management is an in between, you know, party is kind of what you need.

Jack Greco (ACV Auctions & Far Out Ventures) [00:18:30]:

So I can tell you, we used to tell people, you tell people all they got to do is trust us. You just have to trust ACV. You got to trust that, like, if something's wrong, we will make it right. Yes, if you buy a car and it's supposed to be red and it shows up yellow, we'll make sure that at worst comes to worst, the things that get unwound. Right? If that means we, as ACV, get stuck with a yellow car, shame on us. But we're going to put all of our investment in lowering our risk. But we've told you on day 1, we're gonna make this okay. So and we meant that.

Jack Greco (ACV Auctions & Far Out Ventures) [00:19:02]:

Right? I mean, we spent almost no money on digital marketing, but we had a massive marketing budget because our marketing budget was basically making things good for our customers. So, I mean, we were in the business of allowing people. So for for people that want to sell cars, we made it really easy. You don't have to worry about getting paid. You know, we send somebody out there. You don't even need to diagnose or, yeah, dissect or explain the condition on this thing. We'll send somebody out. You just have to know how to call us.

Jack Greco (ACV Auctions & Far Out Ventures) [00:19:32]:

That's it. And then eventually, how you just let us in. And then they would trust those people. And on the buyer side, you just need to know that what we're saying is what you're buying. And for some reason, you don't get that, we'll take care of it. So we've unhinged it. It's not a relationship between buyer and seller anymore. And when we had seen I mean, we as a kid, I snuck into plenty of auctions.

Jack Greco (ACV Auctions & Far Out Ventures) [00:19:52]:

And then as an adult with ACV, I snuck into plenty of auctions. You could see the distrust. So I mean, you know, to anybody out there trying to think about what they wanna do, just find a place where 2 people really don't trust each other. And then force your way in by being an intermediary without calling yourself right? Like an auction inherently supplies a buyer buying something from a seller. So you're under the guise that, you know, Jeff, you go to an auction, and you're going to buy, you know, you're going to buy something from 1 of the sellers out there. But when the auctioneer steps in between, what you understand one degree off, one derivative off is that you really have a relationship with us. So if that's the case and we never screw up, then you're going to trust us. And it takes time to earn that.

Jack Greco (ACV Auctions & Far Out Ventures) [00:20:36]:

But the lifetime value on it's big enough. You know, I mean, if the average dealership is doing 35 or 40 used cars a month, you know, wholesaling cars a month. And, you know, the average dealerships buying, you know, used car dealerships it's buying 8, 10, 12, 15, 20. Now this is on average, right? You have your CarMax's and your Carvanos, but like the business is built at little people. You know, there's a lot of lifetime value there at, you know, whatever ACVs, what whatever their average revenue per unit is right now, $400. You know, you multiply $400 times 40 per month times 12 months, there's a lot of LTV there. We can make a lot of things good and still make money. So I think that's kind of the approach that we took on

Jeffrey Stern [00:21:18]:

it. Right. And then in in parallel, to to use your, you know, words of of labor intensiveness, there's this, like, classic Startup Paul Grahamism of doing things that don't scale. But I I think there's, like, literally something to that, how, you know, When you think about the go to market and and what you guys actually proved out in Buffalo in like a regional local sense that you were able to then, you know, Pour fuel into the into the engine and and take it to scale with with Bessemer and and subsequent rounds of investment. Like, what what was that early doing things that don't scale labor intensive, building of the inspector network to to actually, like, build the the moat, if you will, for for ECV.

Jack Greco (ACV Auctions & Far Out Ventures) [00:21:56]:

Well, I'll tell you what, 3 co founders in the company that held the titles of, at some point, CEO, CSO, excuse me, CEO, chief sales officer, chief financial officer, COO, and CTO all took customer service calls. I mean, like, we like if you want to talk about within the scale, the inspector part of it, if it didn't scale, I don't know what ACV is doing because we're doing the exact same thing we did when we when we hired our 1st inspector, Joe is probably still mad that, you know, we got in a fight and I told him he's got to go out and like, be the 1st inspector the 1st day he was. Think he did it for one day, you know, and he probably will laugh about it if he hears this. But, you know, I would actually make the argument ACV is a business built on things that you typically would not think scaled, but we're a publicly traded company worth a couple $1,000,000,000. So, I mean, maybe

Jeffrey Stern [00:22:48]:

they Scaled.

Jack Greco (ACV Auctions & Far Out Ventures) [00:22:49]:

Right. I mean, like, there's no way to get somebody to drive from 1 dealership to another one faster. Like I didn't like, we we didn't invest in a black like a wormhole or black hole company that, like, jumps you around. And honestly, if anything, the inspections take longer. And yeah. There's some automation inside process. I think in the beginning, it's a lot of talking. I almost think that there's we probably.

Jack Greco (ACV Auctions & Far Out Ventures) [00:23:12]:

And again, I haven't been at ACV for a handful of years now. But I can tell you when we left, the company was scaling and ramping and growing well. And we were treating every customer, every user when they came on the platform, whether they were new or whether they were coming back and they had been off a little bit. Like, it was brand new for them. And we probably don't do scalable things with every single customer. So as opposed to the company, you know, this isn't like the Airbnb guys taking photos until people got good at it. It'd be like if Airbnb came in and said, alright. Your first 10 your first 10 listings, we're going to come and take the photos and, like, hand walk people in.

Jack Greco (ACV Auctions & Far Out Ventures) [00:23:53]:

I mean, I actually think it's not scalable in the beginning every single time. And then the question is, how quickly can you get the training wheels off on these? But I mean, the truth is ACV is not incredibly different. The by and large core of I'm looking at it as an outsider now. Okay. Doesn't look any different than it did when I left or the day we started it. I mean, it's still primarily 20 minute auctions where we do the best job possible telling you what the car is and you bid on it and you slap a button and you pray to God you win.

Jeffrey Stern [00:24:24]:

Knowing that that premise has remained somewhat uniform since inception through today. How do you think about the, the biggest challenges of of each life cycle of the business. Right? Because obviously the company is at a very different place where it was when when you guys started it, on on every front imaginable. But as you went through the, you know, the startup scale up derisking Exercise of, you know, figuring out product market fit, working through the sales motion, building the right team, addressing competitive concerns. Like What were the existential fears at each stage? And how did you guys navigate

Jack Greco (ACV Auctions & Far Out Ventures) [00:25:00]:

them? The first fear was we were never going to get the product built. Like it was originallyI got to ask Dan what the original promise was, but it was like, I want to say it was Labor Day or Halloween of 2014. And then it kept getting bumped and bumped and bumped. I mean, we didn't we launched our 1st car June 1, 2015. K? So it was like, alright. Are we gonna be able to get this together? Is it gonna work? Right? There was technical risk. At the same time, we're like, are people gonna come to this? Because we didn't do any, like, I I will say we talked a lot about this, but June 1st was still a cold start. I mean, you know, we had not turn the engine over before.

Jack Greco (ACV Auctions & Far Out Ventures) [00:25:39]:

So it'd be like the 1st time you're running a car, you just taking off on a road trip. Right? Like, that's kind of the way we function. So, I mean, that was terrifying in the beginning. Right. And then I remember we had 4 straight months of growth. We sold like 53 cars, a 100 and something cars, a 150 something cars, and a 197 cars. And we're like, this thing cooks. Right? And in 4 months, we were selling 200 cars a month.

Jack Greco (ACV Auctions & Far Out Ventures) [00:26:07]:

I mean, that was just that was great. I mean, I I look at a lot of companies in the automotive space. It takes them a year or 2 to get to it, and we've already broken ice on it. And this was all in Buffalo. This is a little Buffalo. Right? And then all of a sudden the sales flattened out and we realized there were seasonality of this stuff. And we were like, Oh my God, are they going to come back? And then we were burning cash faster than we needed to because we didn't really like, we knew we had an account for working capital, but, like, we were trying to be so kind to our customers. We were like, alright, pay us when you can on this.

Jack Greco (ACV Auctions & Far Out Ventures) [00:26:40]:

Right? Like, you don't get the title, but if it takes because we we weren't integrated with financing and floorplan systems yeah. And then, you know, I'm like, like, there was a couple, the first 3 times we raised money, we were like, we're almost out of money. Right. What I would call our pre seed, our seed in our, a round and a round really when Bessemer came in, we almost were out of money. Then those fears dissipated. And then, you know, we brought in George as CEO between the C and the A and, you know, our fears turned to, I mean, all of a sudden, I'll say like, you know, I think we had different ideas for where the business should go. You know, do you go deep or do you go wide? Do we like how fast do we open stuff up, you know, are we able to talent or raise correctly, excuse me, hire correctly? But the thing did have a snowball effect. And, I mean, it was rolling.

Jack Greco (ACV Auctions & Far Out Ventures) [00:27:31]:

I can't remember months outside of maybe a couple of Decembers where we weren't growing every single month. And December is a notoriously slow month in wholesale because everybody, you know, people will take their losses in December, but they won't take their gains because they for tax reasons. And now all of a sudden things pick back up in January. So, you know, there were a lot of stops and starts in terms of our fears. Right. You know, like, all of a sudden we'd be worried about, oh my god, can we find talent? And then it was like, oh, real. Are we too heavy? You know? And none of us had done that before. Like, George had founded a company that grew, Synacor that ultimately went public, but he wasn't at the helm when that happened.

Jack Greco (ACV Auctions & Far Out Ventures) [00:28:12]:

And he'd always been more in the sales side than anything else. Dan, Joe, and I collectively had the equivalent of small business experience. You know, I've been in venture. I was the one with the most venture experienced, but, like, it was primarily in biotech material science. Right? Like these were companies that took 4 rounds of funding before they had a dollar in revenue. You know, Dan ran an incubator, and Joe ran a used car center. So, I mean, I think we were just all very hungry and driven, and we did a great job with our 1st 20 hires. And those 20 hires, when they started hiring, did a good job with theirs, you know, and honestly, showing up at work with good people being like, this is hard as hell.

Jack Greco (ACV Auctions & Far Out Ventures) [00:28:48]:

I will tell you, there are people of our 1st 20, 30 employees that should be multimillionaires. Like, we should have gave them way more equity just based on the amount of value that they added that we didn't. But you know, like initially was us figuring out how we were doing it. We brought in a very involved board. You know, I think that's, easy to see. You see how quickly we were raising rounds, the amount of continual board participation. You know, it's all public now. And then I can tell you for me, like, before I left, I was getting to the point where I was like, All right, this is diverging from what I want to do.

Jack Greco (ACV Auctions & Far Out Ventures) [00:29:25]:

And also, the work life balance sucked. I mean, I was head of strategy, finance, and operations, and we were a Series C company, and that was stupid. It was stupid on me for pretending I was Hercules. And it was stupid because by the time I did ask for help, the company didn't know how to recruit top end talent. Like we got we got really I mean, George was an early investor. We got lucky there, and we got really lucky with our chief sales officer. But, like, that was it. You know, it was, you know, George Waterman, me, Dan Joe.

Jack Greco (ACV Auctions & Far Out Ventures) [00:29:55]:

You know, so I step back, and I was terrified when I step back. I step back being like, I don't know if they're going to actually bring in better talent, and maybe it's because I exist because I was, you know, I think it's fair to say such a keystone in so many operations, right? I did not do a good job of making myself redundant. And then I just parachuted out and I think they did a good job. It took a while. They brought in a good strategy guy. Then they brought in a good operations guy. Then finally, as they were getting ready to go public, they brought in a good the guy then finally, as they were getting ready to go public, they brought in a good finance guy at the top. I mean, there was a ton of really good VP and director level down participants, Vince, but, you know, you need a you need a chief for every tribe.

Jack Greco (ACV Auctions & Far Out Ventures) [00:30:33]:

But it went well. Like, it ended up being the right thing to happen. But that's you know, so so you have this, like, you get this agita both about, like, the company, then about your employees, then finally at the end, about yourself. And it makes it hard. Cause you're dealing with all that at once and life marches on, right? I had a, I had a my, my, my son was born 2 months after we sold our 1st car, which means he was in the womb before we sold the car, which means for 7 months, there was a baby and there was no revenue. So you can imagine what the hell that was like in the beginning. Just kind of crazy.

Jeffrey Stern [00:31:08]:

Yeah. Well, so when you think about stepping away at this point in retrospect, you know, you can, I think, say by most measures of entrepreneurship and success, You've achieved them and we can unpack that, but you know, you can go live on your proverbial low orbiting asteroid, but obviously that isn't the end of your journey And interests and pursuits and, and like, you know, journey to be had in life? So I'd really love to understand how in your Exodus, Afforded the time to really think deeply and reflect about what it is that you wanted to do next. You know, thinking about these higher level concepts of your, your opus and your, your life's work, how do you figure out what it is you actually want to spend your time on going forward, Given this incredible experience that you had.

Jack Greco (ACV Auctions & Far Out Ventures) [00:31:55]:

Doctor. So, in the beginning, and I'm a man of analogy. In the beginning, I thought of myself riding a bicycle. I had to be moving or I was going to fall down. And so I just moved, right? Like I was just moving and shaking, right. I got out of ACV within, I think I took 3 weeks and a company asked me to help them. And I have a little bit of experience in agriculture in the dairy space. And it was a deep tech product, machine learning enabled sensor in the dairy space.

Jack Greco (ACV Auctions & Far Out Ventures) [00:32:28]:

I was helping him in like 3 weeks. I was just like, you know, I basically had the month of August off my son's birthday's in August. My mom's birthday's in August. And by September, I was like, all right, I'm doing this. I did. And that was the reason I say riding the bicycle, like when you ride a bicycle, you got to ride like you ride a bicycle, but you can look around at stuff that's going on, right? And that's kind of what I was doing. I had to be moving in order to focus. Just like anybody with, you know, ADHD.

Jack Greco (ACV Auctions & Far Out Ventures) [00:32:55]:

Like, I might have to fiddle with something while I'm talking to you to actually focus on talking to you. So I have to be doing something in a business to actually be thinking what I want to do. So I got really fortunate. There was, like, a Skunk Works product project that ran through the state where Techstars is trying to do ecosystem development. So I kinda helped the dairy company for 6 months. I did the eco development for about a year and a half. And it really I'm so happy for that impunity. I mean, I hated working for a big organization.

Jack Greco (ACV Auctions & Far Out Ventures) [00:33:24]:

I've gotten fired from every single thing I've ever done, including ACV. That happened early on, and I was brought back. It was more a, I'm having a, I'm having a conniption fit. And, I need, like, to actually take my paternity leave is what it ended up being. Because I took 2 days, which is not smart. Right? And I ended up taking 4 weeks, 5 weeks. But I didn't like the big company part of it, but I really like the opportunity to be like, alright. I have a bubble and that bubble has pushed out me from doing 50,000 other things.

Jack Greco (ACV Auctions & Far Out Ventures) [00:33:54]:

And inside that bubble, I'm actually allowed to just think about the community, the startup ecosystem startup community in upstate New York. That's when I really said, alright, I like helping people. I like I wanna have an impact. I like startups. I've been doing a ton of angel investing, right? Like I basically angel invested to figure out what I liked, had done over a 100 angel deals, direct deals. I was an LP. And at this point, I think I'm an LP in, like, 65 funds or something like that. But I was like, you know, I was like, alright, I'm gonna move some money around.

Jack Greco (ACV Auctions & Far Out Ventures) [00:34:25]:

I got too much of it. Right? I took care of everybody in my family. Took care of everybody. I was like, everybody's happy. If I give them more, they'll be stupid. I didn't want anything from me. I was like, I'm I'm in my late thirties. I don't, I just don't want anything right now because I don't wanna slow down.

Jack Greco (ACV Auctions & Far Out Ventures) [00:34:38]:

I don't wanna stop riding the bike. You know, my dad always says the same. When people retire, they die real quick because like, they stop, they stop doing stuff. And he's like, that's why I hope I don't ever retire. And I feel the same way. Like, I don't wanna tire. Right? Like, I don't I don't golf. I'm a horrible golfer.

Jack Greco (ACV Auctions & Far Out Ventures) [00:34:54]:

I'm horrible at most sports. I was decent in lacrosse and decent in skiing, and I'm okay at a couple other things. And I'm now playing on 2 reconstructed Achilles after I blown a ball. So some of those sports kinda go away. But it really it took me about it took me a couple years. And I still really don't know. I just know what I want to do right now. I know I'm engaged.

Jack Greco (ACV Auctions & Far Out Ventures) [00:35:16]:

Get married next year. I want to focus on that. That my family I always hate when people staggering things, and they say this comes first and this comes second. They're all important. That is the most important thing to me. And then what's comes right after that is having a positive impact in the areas I want to. So I knew I didn't want my epitaph to read, Jack Greco, cofounder of the way used car guys bought cars better. Like, I didn't give a shit about that, you know, but that's what the tabloid say.

Jack Greco (ACV Auctions & Far Out Ventures) [00:35:44]:

They don't say ACV is a, a marketplace for people and relationships, which is what it really is. It's in whatever we're we're shucking, which is cars. So like my whole thesis and everything is I was like, you know, I want to invest in founders that are making a positive impact and where this is their this is what sets them up. Right? Like, I always tell founders. Founders get done with a fundraise, and I go, Are you exhausted? And they're like, Yeah. I'm like, great. That wasn't even the beginning. And I think of ACV as the same way for me.

Jack Greco (ACV Auctions & Far Out Ventures) [00:36:14]:

It was my way I got the funding I needed to run the startup, which is my life. And now I just can't F it up. Right. Because it was a really hard slog. I mean, you know, it was from 2014 till the end of 2018, there was a lot of days, a lot of months. That's a long fundraising cycle. If you told me it took 4 plus years to raise, you know, you're round for your startup. I'd be like, dude, gotta really rethink your startup.

Jack Greco (ACV Auctions & Far Out Ventures) [00:36:42]:

But that's the startup of my life. Right? And now I'm to the point I'm like, alright, what am I doing? I think I'm starting to finally get there. Right? I I run a venture fund right now. You know? So instead of me just being wild bill, the, you know, the angel investors slinging, you know, riverboat gambling guy, which is kind of the persona I had that whole time. Now you gotta be responsible. You gotta be judicious. And I have partners, and it it's it's a different world. And I don't love it.

Jack Greco (ACV Auctions & Far Out Ventures) [00:37:09]:

Like, I don't love rules. But I think it's important to follow them. Like, you know, I want to, when I want to get to a to b, I want to drive as fast as I can, but if everybody does, we'll all die. So I'm okay with some rules, and that's kind of the world I live in right

Jeffrey Stern [00:37:22]:

now. Yeah. Well, it comes back to that that opus idea, the the life's work. I mean, I I think you often hear retirement talked about as normally that explicit marker of the the end of work or employment. And and I don't remember where I heard this, I heard it framed as the day when you actually stop sacrificing today for tomorrow. And so you can just kind of pursue the things you would have pushed off In employment anyway.

Jack Greco (ACV Auctions & Far Out Ventures) [00:37:45]:

Yeah. I I don't have a dictionary in front of me, but I believe the word to retire means to remove or take out of service. Okay, and I'm not ready to stop serving. Right? It's that simple. So, and I love serving, right? Like, you know, founders ask me sometimes, and they've done this as part of Far Out, the fund that I I'm the managing partner of, and, you know, 2 other guys and as well as an angel. And they're like, you're more excited about this than I am. Like, you like, you think that that you're selling me, and I thought I was selling you. And I was like, Well, that's good.

Jack Greco (ACV Auctions & Far Out Ventures) [00:38:27]:

I said, that's a good relationship. Right? Like, you want you and your wife to both want the other person. You want to both feel like the lucky one. And I feel lucky to have an opportunity to support these founders. Right? I do. And I'm not saying I'll never found something again. I totally will. But where I am right now, this gives me an opportunity to be on the other side of the table and do it all the ways that I never had anybody help me and take care of me on.

Jack Greco (ACV Auctions & Far Out Ventures) [00:38:49]:

So it's a little bit of, like, chip on my shoulder, but it's a good chip. And I got strong shoulders, so it's okay.

Jeffrey Stern [00:38:57]:

I like that a lot. Well, I I've I've heard you talk before about how you want to identify and and elevate these ideas coming out of smaller places was was I think the phrase. And so I'm curious how you actually go about operationalizing that and getting people to raise the bar for ambition and even think about what can even be accomplished in the 1st place. I remember, Reading a book recently that, that talked about Barry Diller, who runs, IAC, a multi $1,000,000,000 media and internet And and the essence of the story was that someone in Dillard's World came to him and told him about this opportunity and said that, you know, if we really do it right, we'll have a $100,000,000 in revenue in this kind of timeline. And if we really do it right, we'll have a $100,000,000 in profit. And Diller, you know, looks back at him and is like, why bother? Like, why would we even work on something so small? And so, I thought it was just kind of a funny story, but you know, like, what does it mean to go big in your mind when we think about the scope of

Jack Greco (ACV Auctions & Far Out Ventures) [00:39:55]:

ambition? Well, so here's what I noticed, right? Stealing from, what's his name? Gordon Gekko or whatever. Like, greed is good. I see a ton of it in the world, right? I think that that's great that there's people that want to grow things incredibly huge. ACV is just to be clear as of today, not a company that makes $100,000,000 in profit. It actually does not make any profit still. So we are still continuing to pedal the hopes and dreams of a better tomorrow and a multiple on EBITDA that doesn't exist. Okay. So just to be factual.

Jack Greco (ACV Auctions & Far Out Ventures) [00:40:30]:

But the way I look at it is this is I think it is easy to be a late stage investor. And I want all the investors they can turn off this podcast if there's anyone listening to it. But I think it's easy. I think it becomes a numbers game, and it's not a people's game that point because there's too much diversification of people. I mean, if you think any of these CEOs at any of these big companies, like have that much influence over the overall health and well-being of their people. They have the power. And in very few cases is used appropriately or fiction or at all in order to do anything about that. And so I am not an expert at manipulating a financial statement and creating, you know, categorical growth factors off of following some type of marketing plan and thesis.

Jack Greco (ACV Auctions & Far Out Ventures) [00:41:18]:

I I actually am not operationalized at all. I'm not I'm no more operationalized than a thunderstorm that comes together out of the blue. Right? Somehow, there's natural effects that create that, and then it goes away. And they come up all the time, but I don't think a thunderstorm actually ever thinks it's going to shoot a bolt of lightning down. Right? So I am in the business of people, and I am in the business of taking the bets on people early on in identifying human beings and also in identifying market opportunities. I believe in building. I also know that there is this positive vacuum. Once you get to a particular size, it's probably around the Series A or the Series B mark where the company is going to be what it is, and it's going to get sucked up if it deserves to get sucked up, right? So I really exist is this one who's, all right, like, you know, yes, I understand, like, the markup on jewelry at a jewelry store is like 90%.

Jack Greco (ACV Auctions & Far Out Ventures) [00:42:20]:

And I don't mind being the one digging up gold, making almost no money digging it up because you could put inside of a system that we're seeing this with a fund where you actually can make these wildly profitable, and you can give people the opportunity to do what I think is easier, which is do later stage follow on investing. So the truth is I actually think it's like, I I personally have to have the same level of conviction every single bet that I make. I can't define that as a 9 out of 10 or this high up on the meter. But I have to be willing to if if the opportunity was presented itself, if I was gonna make a clone of myself, the clone of me would go work for and run and support that startup. Like, that is my threshold to make an investment out of our fund or historically a large angel bet, right? So what it turns into, who in the hell knows? I mean, I can tell you ACV, the smartest thing we did was raise a ton of money. It was. Well, I mean, it was higher I will say this. 1, it was higher happy the the right happy people that knew what they were doing.

Jack Greco (ACV Auctions & Far Out Ventures) [00:43:29]:

2, we empowered them. 3, we got really lucky with the size of the market. And 4, we raised a ton of money. And, like, the first 2, I mean, we did intentionally. And the other 2, we knew they were big. But it's not like Dan Joe and I sat around and said, wow, the TAM is huge on this. It was this is a problem. So it's tricky.

Jack Greco (ACV Auctions & Far Out Ventures) [00:43:49]:

Right? Like, I don't necessarily like, don't get me wrong. I will happily take a company that could do a $100100,000,000 in profit. I'll happily take a company that could do a 100,000,000 in revenue. Or even in today, 40 or 50,000,000 in actual net revenue is like a real business. Because you gotta remember, I'm also be getting in on day 1. I'm one of 3 guys that run a pre seed and seed fund. Pre seed to me means I got an idea. I got some early traction.

Jack Greco (ACV Auctions & Far Out Ventures) [00:44:19]:

Maybe I got a little bit of coin coming in from it. Maybe I don't. But I got a plan, and I got a team, and I have a way to talk about executing on it. And then seed's like, alright, we got some money coming in. You know, I do more of our seed deals. So I do like investing in stuff with early traction. But because I want to be able to talk to a customer, I want to be able to see the dynamics the sale. Right? I'm a sales guy to begin with, too.

Jack Greco (ACV Auctions & Far Out Ventures) [00:44:41]:

I mean, my father had me selling furniture way too young of an age, you know, and you just kind of get that built into your in your repertoire. The product I mean, a business has no revenue, has no value. Right? For 98% of them that are not working on a cure for some type of cancer or some type of AI that's gonna take over the world. Right? But the majority of businesses, if there's no revenue, there's no value. So I don't look at it like it needs to be the biggest thing in world I think everybody's looking for the biggest thing in the world. I think the biggest things in the world come out of things that are really good that all of a sudden catch a nice updraft, and they did the right hire, and it was the right timing and a bunch of things humans can't predict, and it shoots up. And so I like to take I like to put as many think of a ping pong ball. I like to throw as many ping pong balls in the air I can.

Jack Greco (ACV Auctions & Far Out Ventures) [00:45:31]:

And if the wind catches it the right way, shit. It's Uber. But I did not think a service on your phone to get black cars to, like, drive you around. Luxury black luxury cars to drive you around was something that would be as big as it was. Right? Like, okay, yeah. Like if somebody looked at like Microsoft in the beginning, okay, it makes more sense. But I think that it's as much luck as it is, you know, it's not luck building a great company. It is luck getting a great company to turn into Amazon, right, as opposed to the 7 people that that don't do that.

Jeffrey Stern [00:46:05]:

So so to that, and also your framing of if later stage is more of a numbers game and the earlier stages where you're spending more of your time thinking right now It's more of a people's game. What traits or characteristics make for the best founders? Right? You know, at this point, you've made hundreds of angel investments, Which is a lot, meaning you've, you've spoken with how many additional founders that you've actually met with, let alone made actual investments in. It's a substantial sample size. Yeah. You had mentioned your own chip on your own silver. Are there characteristics like that of those who have risen Doctor. And been successful, or is it less tangible than that? How much, to your point of luck, is involved?

Jack Greco (ACV Auctions & Far Out Ventures) [00:46:45]:

Doctor. Yeah. Tenacious, organized, trustworthy, humble, hungry, pleasant, maybe the on like like, trustworthy and that you can trust them, but also honest in the sense of the between state, between trustworthiness and humility, which is like honest with reality. Like, those are the traits I would they just come to mind initially that I need to see and feel in order to do anything. Like, I need to know that I can trust you. You know, I know what it's like to have an infinite in my hand. I have one. I had one.

Jack Greco (ACV Auctions & Far Out Ventures) [00:47:23]:

He is much bigger now. You know, I need to know I can trust you holding that. I need to know the way you make decisions. Look, I don't need to know all of them. I don't need to micromanage you. It's like if we're going into a situation, I need to know that I know the way you make decisions, and I'm cool with that. Right? We need to vibe because I'm also gonna put I mean, I I don't support the angel investments that I did before to any real degree now. I had to kinda sunset all of that.

Jack Greco (ACV Auctions & Far Out Ventures) [00:47:49]:

There's a handful of them that I kind of got grandfathered in, but by and large, majority of those are on their own. But for the 1st year or 2, we got to work together. I mean, I talk to the founders, who are all the CEOs of the companies I've led in far out. I talked to every single one of them at least once a week. There's some who might talk to 5, 6, 7. If there's busy stuff, I might talk to him 25 times a week. Right? I need to know, like, you're a good partner. Like, I I the same traits I would look at in a partner, I got to look at in a CEO because that's really what you end up being in the beginning.

Jack Greco (ACV Auctions & Far Out Ventures) [00:48:24]:

And that's on the person. I mean, I wanna understand the market. I wanna understand the vision. I wanna understand you felt it. You know, I tend to invest in founders that have been in the industry they're in for at least 10 years. At least 10 years. Right? I'm investing in some young founders. So, but that doesn't mean you can't be in it.

Jack Greco (ACV Auctions & Far Out Ventures) [00:48:44]:

It means you have to be adjacent to it, right, or close to it. But I like people to have felt the pain and know how to fix it. And my job is just to be able to help you scale your vision, tweak it along the way. But by and large, I don't expect you to really be changing too much. You might have to because of financial things, but I'm not like, oh, they're smart. They'll figure it out. No, you're smart. You should have at least feel like you figured it out already by the time I get involved.

Jack Greco (ACV Auctions & Far Out Ventures) [00:49:10]:

And we might have to figure it out again, but it's great that you have adaptability, and you're, you know, athletically minded that you are limber, stretching. You can, like, move through different aspects of the business really well. But, I mean, honestly, and not that everybody I invest in is my friend, but I come to fall in love with these founders. It's a personality trait I have where I take more pride in. If I work with you, you being successful means more to me than me ever being successful. And I wanna make sure there are people that I will root for indefinitely. And it's not true of everybody, you know. Like, there are founders where I'm like, you're probably gonna make a ton of money, but I gotta give you to somebody else because I can't support you for forever.

Jack Greco (ACV Auctions & Far Out Ventures) [00:49:50]:

There's something in the way you do something or, you know, ethics or morals or something that we just don't vibe. And if I don't jive with you, I don't jive with you.

Jeffrey Stern [00:49:59]:

What's maybe your most memorable pitch or initial meeting with an entrepreneur where you thought, you know, this is something that I cannot wait to invest in? What was the most memorable first impression or an impression? I'm sure there's a ton that you love, but if any come to mind.

Jack Greco (ACV Auctions & Far Out Ventures) [00:50:17]:

Yeah, some of the best first pitches I've seen are some of my quickest flops. You know, I invested in a company out of Albany. My my my partners tease me about it. But it was a young founder, super energetic. I'm not gonna name the company because that it's gonna crap on him, but, you know, I I saw it. I was like, I love it. I didn't know a lot about it. One, so that's the problem.

Jack Greco (ACV Auctions & Far Out Ventures) [00:50:40]:

Loving something you don't know a ton about. And this was an angel bet. So, like, you know, I could do whatever. And I didn't go in super heavy on it, initially. I did not. But I heard the pitch. I believed it. I trusted the guy.

Jack Greco (ACV Auctions & Far Out Ventures) [00:50:52]:

I liked how far ahead he was and the team he put around him, and he was advanced. And I bought in on it. You know, it was a marketplace play, and it just, it just went to crap. I think there were some overlooked aspects of the business. And again, if I had made that bet through our fund, I would have been a lot more involved, but that was in the era of good times when I was like, I'm throwing money everywhere. Like, I'm helping these companies, but there was a lot of mouths to feed. I'll juxtapose that against the deal I'm doing right now at Far Out. The woman is the founder, and I will say her name, Anne, runs a company called Insane.

Jack Greco (ACV Auctions & Far Out Ventures) [00:51:29]:

The first 2 or 3 times I saw it, there was something in it. They just, I kind of passed over it. And Anne stayed on me. She was, I don't know if she liked me or she just knew I had capital and she was doing it with everybody. I don't know. You'll have to interview her someday and ask her why. But then I was in New York, and I was like, Hey, I'm here. You know, I kind of felt a little bad.

Jack Greco (ACV Auctions & Far Out Ventures) [00:51:52]:

I was like, You're a founder in New York, and I haven't given you that much time. And it did come in as a referral, and I sat down with her, and I went from being, like, whatever. I'll sit down with her. I walked away. I'm like, I'm investing in this company. I didn't get it before. She was it was like it was like I was talking to somebody that had, like was using words and language. Like like, they were an adult, and I was kid, and I wasn't getting what they were saying.

Jack Greco (ACV Auctions & Far Out Ventures) [00:52:17]:

You know? She was using word like influencer and connector and stuff like this, and I'm thinking, like, this is a social media product. Right? And it wasn't. I think it's a very I think it's going to be, and I it's one of the investments I'm the most excited about. It's going to be what I think transforms, if not all retail, at least luxury fashion in a B2B way, a B2B marketplace way, you know, kind of bringing in what was the beginning of a trend of using, you know, instead of using the words like connector and influencer, using words like a consultant, like a wardrobe consultant or a personal stylist, you know, to be able to help you make the purchasing and buying decisions you wanna make, but really empowering them with a back end operating system. And so the 1st couple times, it didn't go great. You know? I was just like, alright. Like, I don't really get it. And I showed it to a bunch of VCs, and they said the exact same thing.

Jack Greco (ACV Auctions & Far Out Ventures) [00:53:12]:

And I said, it took me 3 or 4 times. And at this point, I'm like head over heels. I'm so excited to be, you know, we were the 1st commit in the round, and I'm really excited to help, like, pull this round together, which by the time this airs, hopefully it'll close. It'll be, you know, something between a 1,000,000 and a half to $2,000,000 round in a great founder, in a great business, they had all the attributes they just said, but just I didn't get them even the it wasn't even just the first time, but the first 2 or 3 times. And now I'm a believer. Now I believe in the thing that you earned that. That means a lot to me.

Jeffrey Stern [00:53:44]:

What have been the most transferable or Like earned learnings for yourself on the investing side of the, you know, ecosystem in a way that you maybe didn't appreciate As a as a builder. And now, you know, with the kind of, again, operator investor title, if you will. Right? What what what what do you What's interesting about being in that role?

Jack Greco (ACV Auctions & Far Out Ventures) [00:54:11]:

When I so I will tell you this. I did not understand when I was a founder how important it was to align with peers, 1. 2, to understand the venture game because I didn't get it. I did not understand like, I'd even worked for a venture firm for 5 years, but, like, I did not understand the software East Coast venture game. The way valuations were struck, the way these deals were done, there are nuances in there. And I wish I had a mentor. I didn't have any mentors, like, that were that had gone through it. You know? So, you know, I I really downplayed and didn't even think about how important it would have been be more thoughtful in understanding the game I was playing and not just the company I was building.

Jack Greco (ACV Auctions & Far Out Ventures) [00:54:57]:

Because venture is a game. 100% a game. And that's okay. It's a good game. It's an important necessary game, but it's a game. You know, so I wish I understood that more. I mean, as an investor, now, you know, in in counseling with other investors, you I I would say founders have don't really understand why people are betting on them. I don't see it being super clearly communicated.

Jack Greco (ACV Auctions & Far Out Ventures) [00:55:22]:

I don't see people saying, I'm doing this bet because the metrics are off the chart, even though I don't know a damn thing about this industry, which is honestly the reason some people do this. You know? Or I am following a trend and you just happen to be the pitch that got in front of me, and there was something in the color pink you used that made me open it and dig into it. And this is the horse I'm betting on, you know, like, I mean, I don't want to make it seem like venture investing is a casual thing, but we are humans, right? And I thought like, Okay, you got to be the best. You got to be this, this, this, this, this, right? I thought about being an athlete, like maxing out our combine rankings. When I really realized you just somebody catches a glimpse of your game tape, and they might like you. And you don't know what's gonna get these guys to like and women to like you or not like you. You just don't know. And I will say this, the venture game it's tough.

Jack Greco (ACV Auctions & Far Out Ventures) [00:56:16]:

I mean, you don't realize that like the person investing in you runs a two sided marketplace. They have to raise money and then they have to find you. And guess what? As the founder, you are on the weaker side of the two sided marketplace because there are a 1000000000 founders, and there are not a 1000000000 people that are gonna give me money. And it makes it tough. And in the Venture game, a lot of people have made it already. And I tell people, I go, Look, I grew up in 2014, 2015, 2016 in a world in Buffalo where there wasn't a ton of capital. You had to take what you got. What's important to really reevaluate who's on the other side of the table because, like, I'm not some, like, poor stowaway orphan that's just happy for, like, a family to take me.

Jack Greco (ACV Auctions & Far Out Ventures) [00:57:00]:

Like, I get a decision in this as a founder. I wanna know, are you hungry? Are you gonna help me? Are you gonna work? Or are you just gonna be on my cap table? Or are you going to be a detriment? When things get hard, are you going to blame me, or are you going to support me? Right? Like, this is much more like picking your parent than it is like being so grateful that somebody just scoops you up. And it's hard because most companies don't get to pick that. And, again, they don't get the game. They don't know when to start. They don't know how to start. You know? So it makes it tough. I mean, this is I I could talk to you for 3 hours about the things I've learned just in the last, you know, really year and a half being a professional venture capitalist, right, which is what I am now.

Jack Greco (ACV Auctions & Far Out Ventures) [00:57:44]:

Even though if there's video on this call, I don't look very professional right now. My hair looks like it's going in twenty different directions.

Jeffrey Stern [00:57:50]:

Fortunately, no one has to see either of our

Jack Greco (ACV Auctions & Far Out Ventures) [00:57:52]:

faces. No. No. No.

Jeffrey Stern [00:57:55]:

Well, I I could ask you about all that stuff, and what it is meant to take this professionally. I I guess the did it did it not feel was it less of a Like, did you not think about it professionally prior? Like, prior obviously to the fund, but, like, at what point did it make sense for you to to to think about it seriously?

Jack Greco (ACV Auctions & Far Out Ventures) [00:58:16]:

Well, I'll tell you what, when I started to I mean, I invested every single penny that I ever made that I ever made at ACV as of the beginning of January of 2022. All of it. So guess what? When you stick your hand in the jar, and there's a pickle, and there's another pickle, and there's another pickle, and there's no more pickles is when you start going, Oh, shit. I'm out of pickles, right? Like I wasn't even thinking about that. And look. I mean, I I've had a bunch of I think I've got 5 companies that failed 7 or 8 exits and a bunch that are alive just independently, which at this point, I've taken a back seat on. And, obviously, now we have a fund and stuff. But I knew I was gonna be okay.

Jack Greco (ACV Auctions & Far Out Ventures) [00:58:58]:

I mean, I I put as about as much money into funds as I put into direct investing thinking, if worse comes to worse, I'm going to learn. And these guys should at least give me 1 to 2 times my money back in 8 to 10 years. So it was almost like parental supervision on my cash. But when I started getting down on cash, I was like, okay, I've cycled through this. What did I learn? I've learned standardize your check sizes. You use a process. Focus on things you're good at. Don't get into crazy stuff.

Jack Greco (ACV Auctions & Far Out Ventures) [00:59:25]:

Don't bet on, like, these, you know, a great pitch. Don't bet on a great pitch. Don't be afraid to bet on a bad pitch. You know, like all this, like, if, like, if all the grandfatherly spirits out there just sat around me, it'd be the crap I would have learned at a, you know, sitting at a dinette counter with them. Right? It was just like soup but now I had a reference point for each one of them. And I was like, I can remember how hard it was when we did AirXpert. Right? And I'm chairman of the board at AirXpert. Right? Like, that's a that's one of the few things I carried over.

Jack Greco (ACV Auctions & Far Out Ventures) [00:59:59]:

I'm really passionate about it. Seeing that happen to Buffalo company. You know? Or, man, I was so stupid when I didn't put more money in on tackle. Tackle was like the 1st unicorn I bet on at a seed around. And I just didn't have a lot of capital at that time. And instead of being like, No, I'm going to standardize things to have enough left, I didn't get to put as much in. And it's been an awesome return, but it was it's on a smaller multiple. So I think when you start to look and your bank account goes from having millions in it to hundreds of thousands to maybe a points, you know, tens of thousands or ones of thousands, you know.

Jack Greco (ACV Auctions & Far Out Ventures) [01:00:34]:

And I ran I run it down to the edge every time. And then it comes back. It's like a well. You just pray to God and wait that the water comes back. Right? But you start to realize like, okay, I gotta be thoughtful in this. The same way that I'm like, I'm not surprised that now all of a sudden it's hotter out, and we just so happen to have enough technology know, global warming's happening. If this had happened 200 years ago, they're like, why is this so damn hot? I don't know. Maybe it's something we're doing.

Jack Greco (ACV Auctions & Far Out Ventures) [01:00:59]:

And then you ask the question. So it was like, why do I have less money in my account? Oh, I've do been doing a bunch of investing. Okay. Well, let me now think about that. Right? But but I take a very seasonal approach to what I do in the sense that it's episodic. I'm, you know, I'm heavy investor, and then I'm heavy reflector. Heavy heavy investor, heavy reflector. And maybe it'll be a detriment because, you know, my my investments are, like, you know, stepwise, boluses.

Jack Greco (ACV Auctions & Far Out Ventures) [01:01:24]:

It's just like, boom, boom, boom. I'm doing this thing with my finger where it looks like, you know, nothing, and then a big hill, and then nothing. But, you know, I think that's when it became real. And I think it really became real when I got it wasn't even the 1st company a couple companies dying. It was the 1st couple companies really growing. And I was like, crap. Okay. Now I got data.

Jack Greco (ACV Auctions & Far Out Ventures) [01:01:47]:

Right? I mean, like, how many people have a 150 data points of something theoretically stupid they did, you know, that's written down in legal document and be like, why they do that stupid thing? Why they do that stupid thing? Why this stupid thing work? Why that stupid thing not work? You start to learn and you learn about yourself. And I'd say that mixed with a little bit of therapy and spending more time up in the Adirondacks and watching my kid grow up and falling in love and realizing life goes quick and all of a sudden you you're like, shit, I don't want to go fast anymore. They used to call me speedy. Right, I don't think anybody's as fast as me. Right? And I I I offered a challenge to anybody on that. I can build a financial model faster than anybody else you ever met. But, and I think, think fast. I'm not the smartest guy, but I think fast, but you know, I was like, I'm done being fast.

Jack Greco (ACV Auctions & Far Out Ventures) [01:02:36]:

I want to build something durational. So I gotta go slower and I gotta get help and I gotta put a process around this. I gotta stop being stupid. The problem is I won't stop being stupid because venture is kind of stupid thing. Right? You got an idea and also it's worth $5,000,000. That sounds stupid. If I said it to my son, he'd be like, dad, that's stupid. I'd be like, Yeah, it is.

Jack Greco (ACV Auctions & Far Out Ventures) [01:02:57]:

And that's what I do for work. People have ideas, and I tell them it's worth $2,000,000, and $3,000,000, and $4,500,000, and I give them money on that. It was like, holy cow, I should be a professional idea maker, but you know, it's okay. You know, I, I, the world needs it and it has proven lucrative and profitable enough for myself and the people around me that I continue to be lucky and blessed every day to play this game. And I think that's why I run-in a process now through a fund.

Jeffrey Stern [01:03:25]:

In in the intentionality of of of slowness and and reflection, have you, you know, changed your mind about any other kind of long held beliefs that that you've had more

Jack Greco (ACV Auctions & Far Out Ventures) [01:03:37]:

recently? Yeah, some are positive. Like, I mean, I'm a conservationist the way you probably think of Teddy Roosevelt being a conservationist, right? Like, I love trees and I don't mind shooting a bore if it's between them. And I think the world is going to make it. I don't know if mankind is going to make it. I always thought everything would. I also always thought everybody was deep down good, and I haven't lost that belief, but it has been challenged more as I start to reflect back on things and stop being ignorant. I used to love cars, and this had nothing to do with ACV. And I see how like we fall in love with like big price things.

Jack Greco (ACV Auctions & Far Out Ventures) [01:04:22]:

And in some ways, it's materialistic, and you really don't need them. Like, my favorite days are days where I don't get behind the steering wheel. And maybe that's because my cars are all jalapis, but, I'm just saying. And I start to back up, and I realize that all the stuff I wanted to do, like it no longer I will say, and I credit my fiance on this, she has helped me slow down, and she has said, you know, she has helped me understand it's not about how many meetings you have. You're not in a competition. You're not trying to prove anything to anybody. Like you said, like I did enough that if I die, my obituary will be nice and long and full. Right? I don't feel like I've lived half a life.

Jack Greco (ACV Auctions & Far Out Ventures) [01:05:01]:

You know? In Blade Runner, I love the quote, the star that burns twice as bright only burns half as long. Right? And it's like, okay, do I want to burn out? No. So it's now I'm trying to get more reflective. I'm trying to get more proactive. I thought of myself, for the few years I was a horrible baseball player that I played, I was a catcher, which is funny for such an alpha guy to be a catcher, except you realize you get to yell at everybody. And that's the best part of it, but I don't want to be the catcher anymore. Right? I don't want to be reactionary. I want to come in.

Jack Greco (ACV Auctions & Far Out Ventures) [01:05:32]:

I want to throw my pitches. And I want to be thoughtful. And I think, I think when you're proactive, it allows you to be more artful. Not that there's that art in the way you show grace in receiving somebody else's lob of crap, but, you know, I've decided that life is short and you know, yes, it's more important to listen than talk. And yes, it's more important. There's still life's still long enough to be patient, but I'm ready to start calling my shots more. And I always thought that I was, remember saying like, I've always helped other people with their ideas. I wonder if I'll ever do mine.

Jack Greco (ACV Auctions & Far Out Ventures) [01:06:07]:

And in some weird way, that's what this fund is because my idea is not to run a company in the medical space or the material science space. My idea is to fundamentally straighten out this crooked relationship between people that sit on opposite sides of a table in an early stage company. Right? Primarily investors and founders. So that's the line I'm trying to straighten. That's awesome. Takes a lot of hammering,

Jeffrey Stern [01:06:36]:

man. You know, the traditional closing question that that I ask Folks is, for their favorite hidden gem in in Cleveland. But I think You are actually the 1st person on the show not classically associated with Cleveland in the way that that others are building an ecosystem. So I'd love, for 1, you know, Give the the plug for Buffalo and, you know, what what you love about it and and a hidden gem of Buffalo, if you will. And then, you know, we did we did meet here in Cleveland. And so, you know, your your your perceptions of of the city and and your own favorite, you know, takeaways from it.

Jack Greco (ACV Auctions & Far Out Ventures) [01:07:12]:

One of my favorite things, you know, whenever people talk about Buffalo, they talk about food, and they talk about the wings, and they talk about all that. They do. I like to tell people, I think my favorite restaurant in Buffalo doesn't even serve wings. And it's literally across the street from the airport. It's called Charlie the Butcher. And I could eat it literally every single day the rest of my life. You know, in addition to that, I would say this, like I'm not from Buffalo. I think one of the hidden gems here, as opposed to other cities is I have in my travels, never seen a place where people love where they're from so much.

Jack Greco (ACV Auctions & Far Out Ventures) [01:07:53]:

And I'm from Rochester. It's an hour away. And I would say whatever is in the water that makes the people love the hell out of this place. And if you've been to a Bills game, yeah, it's a lot of fun, but it's because it's literally civic pride on the level of like soccer in Europe. And buffalo hasn't been in the same place for, like, 700 years. Like some of these places in, like, you know, Eastern Europe have. Right? For some reason, for a place that's got the crappiest amount of snow and it's only warm enough to go outside without your shoes on for like 4 months, it has found a way to enchant and keep its own, at least in their hearts, if not physically. Cleveland, I don't know as well, but I will tell you a very small hidden gem.

Jack Greco (ACV Auctions & Far Out Ventures) [01:08:39]:

If you go into the Guardian Stadium, there is the Memorial Park. And, actually, one of the first guys that committed to us at ACV, who have us also be my uncle, if he's listening, David Newman, he has a brick there as the number one tribe guy. And it's funny whenever I go to the stadium, which I try and get to once or twice a year, even if I'm not with him, which he drags he lives in the Carolinas now but he comes up and he sees them. He drags this he he drags us to that brick every time. And to see, like, how much he still loves the place, it must be a really special place. Know, it makes you feel the same way that it does about people in Buffalo. So super hidden gem that no one here is going to care about, but, you know, just think all those people that bought bricks really give one one hoot about that place because we're not Florida and we're not Texas and we're not the Caribbean and we're not Europe. And that's okay.

Jeffrey Stern [01:09:34]:

Yes. Yes, it is. Well, no, I think again, back to the, the kindred ethos there, there is this, the civic pride in, in the city that I, I, I think is shared in, in both. So a place to to wrap it up here. Jack, thank you so much for coming on. This was awesome.

Jack Greco (ACV Auctions & Far Out Ventures) [01:09:51]:

Thanks, buddy. I really

Jeffrey Stern [01:09:52]:

appreciate it. If people had anything they wanted to follow-up with you about, what would be the best way for them to do so?

Jack Greco (ACV Auctions & Far Out Ventures) [01:09:59]:

DM me on LinkedIn, and do not make the note you send me look like you're trying to sell me something because I get so many of those, you know, and I actually write, a weekly newsletter about Buffalo called Buffalo Bridge. And if you DM me and you're interested, I'll tell you about it. You can see it on my LinkedIn profile, but that or I'm in the grass lot every home game Mhmm. And you can just look for the guy that probably has a shirt off and is screaming louder than anybody else. And that'll be me. Or I'll be right next to that person because that'll be somebody I envy. It'll be 1 or the other.

Jeffrey Stern [01:10:38]:

Awesome. Well, thank you again, Jack.

Jack Greco (ACV Auctions & Far Out Ventures) [01:10:40]:

Thanks a lot, man. I appreciate it. Go

Jeffrey Stern [01:10:42]:

Bills. That's all for this week. Thank you for listening. We'd love to hear your us on today's show. So if you have any feedback, please send over an email to jeffrey at lay of the land dot f m or find us on Twitter at podlay of the Land or at Sternfa, j e f e. If you or someone you know would make a good guest for our show, please reach out as well and let No. And if you enjoy the podcast, please subscribe and leave a review on iTunes or on your preferred podcast player. Your support goes a long way to help us Spread the word and continue to bring the Cleveland founders and builders we love having on the show.

Jeffrey Stern [01:11:16]:

We'll be back here next week at the same time to map more of The Land. The Lay of the Land podcast was developed in collaboration with The Up Company LLC. At the time of this recording, unless otherwise indicated, we do not own equity or other financial interests in the company which appear on the show. All opinions expressed by podcast participants are solely their own and do not reflect the of any entity which employs us. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Thank you for listening, and we'll talk to you next week.