How to modernize an old technology like outdoor billboard advertising

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Today’s guest saw an old technology and said, “What if I modernize it?”

Instead of forcing people to remember the company name on a billboard, their phone number, write it down, and go buy it. “What if I create a web page where anyone can go and buy like they buy anything else?”

I care about his story. But I’m also thinking in my head, “What else is outdated that we can modernize using some of the things that we already know?” And as you’ll see, he started out very basic the way that you can when you come up with something that you want to modernize.

Matt O’Connor is the founder of AdQuick, a marketplace to buy and sell outdoor advertising.

Matt O'Connor

Matt O'Connor


Matt O’Connor is the founder of AdQuick, a marketplace to buy and sell outdoor advertising.


Full Interview Transcript

Andrew: Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of Mixergy where I interview entrepreneurs about how they build their businesses. And I do it for an audience of ambitious people. Look, when you watch . . . I don’t know if you do. Matt, you tell me if you do. When I watch a baseball game, I, in the back of my head, imagine what would it be like if they just called me and said, “Hey, Andrew, come on down here, we can use you in the outfield.” If I’m watching a musician play even at a local bar here, I imagine what would it be like if I had to get to stand up on stage and play with them.

I don’t play music. I don’t play sports. I don’t do any of that. And still, there’s a part of me that just wants to be a part of it. And the reason is I find that when we watch other people doing things, especially when they break down how they do it, there’s a part of us that vicariously wants to live through them, that wants to experience what they’re doing, that wants to do it too. Just like when my kids play Lego, I can’t help but sometimes grab it and put it together. If I put a soccer ball in front of you, Matt, if I kick it to you, you can’t help but kick in. Am I right?

Matt: Yeah, it’s instinct.

Andrew: Yeah.

Matt: That’s what people do and you kind of absorb from watching others.

Andrew: Yeah. And that’s the thing about listening to people start businesses. My dad growing up would hear people talk about starting businesses. Would hear them talk about and analyze their companies, would sit at a restaurant with somebody with someone else who would say, “I wonder what they make over here. Let’s count how many people in the restaurant. What do they actually charge?” You know, like, and the more you do that, the more he did it, the more he was drawn to entrepreneurship several times. So that’s what these interviews are about, to open you up to other people’s experiences so that you can learn from them.

Now, today’s guest who you’ve heard, Matthew O’Connor, did something that many of us have done. I know I have done through outdoor billboard advertising. I’ve driven past them so many times and in the back of my head thought, “Old technology.” Like I saw your lip do something as I said that. It’s like, “You insulted my thing.”

Matt: No.

Andrew: I dismissed it. I’ll be fully frank and honest with you. I completely dismissed it. I thought, “Old technology. It doesn’t . . . ” I don’t know. “You can’t target people really well. It takes forever.” Or just, “Why would you do that when you could just go buy a Facebook ad, for example?”

Now you’re somebody who was smarter than that. You said, “Hmm, it is a little old technology. What if I modernize it? What if instead of just letting people pick . . . ” And there’s always a phone number if you look carefully or a company name underneath it. Instead of forcing people to remember the company name of the billboard, remember the phone number, write it down and go buy it. Or worse, just see these things as stuff that’s just outdated and not for them. “What if I modernize it? Create a web page where anyone can go and buy like they buy anything else?”

Hell, people test ads on Facebook. They test ads on Google, they test ads on random websites that they’re passionate with, they test out to my podcast, why don’t they just test it an ad outdoor and maybe it’ll work. And so that’s what he did. I should introduce him. His name is Matthew O’Connor. He is the founder of a company called AdQuick. It is the quickest way to advertise outdoor and to measure the ad’s effectiveness. We’re going to find out how he built this company up thanks to two phenomenal sponsors.

By the way, as we’re doing this, I care about his story. But I’m also thinking in my head, “What else is outdated that we can modernize using some of the things that we already know?” And as you’ll see, he started out very basic and the way that you could do when you come up with something that you want to modernize.

All right, so this interview is sponsored by two phenomenal companies that I haven’t talked about much because they’re brand new sponsors to me. The first, if you’re doing anything in your company in a repetitive way, if you’re teaching people how to do something that’s been done before, you need to create a good online process for them to learn and follow. Trainual is a software that I love to enable you to do that. And then second, if you have a second in command, they need the training, they need the peers, they need the people who are going to help them become the right COO or VP operations or general manager, whatever you call them. And the COO Alliance will do that for you. We’ll talk about those later. First, Matt, good to have you on here.

Matt: Hey, excited to chat with you.

Andrew: Matt, what’s your revenue? How much are you doing?

Matt: If I go into that we’re growing 4X this year on top of 4X last year. But specifics, we don’t get into on revenue.

Andrew: Give me a sense of revenue. Last year, did you do over five million?

Matt: Yeah.

Andrew: Okay. All right. I’ve got some data here in front of me. But I also know you’re not going to go into detail on it. And all I’m looking for, just a sense of scope and size. And the company started how long ago?

Matt: So we launched November 2016. So about two and a half years being around.

Andrew: Give me an example of a company that we know and respect that’s using AdQuick to give us a sense of what they’re doing with it and what’s possible?

Matt: Yeah. So one of our favorite customers is Squarespace. So obviously, they are helping people build websites and actually an interesting angle for a lot of people out there. But, yeah, we make it easy for them to find inventory in any market, including abroad now, and they can buy those pieces of inventory and that are relevant to them in as few as a couple of clicks, saving them dozens or hundreds of phone calls and emails. They login, buy it on AdQuick.

Andrew: Why? Why buy a billboard ad instead of an online ad? Or you know what? Actually, there’s a flaw in that question, it doesn’t have to be instead of. In a world with online ads, why would somebody buy a billboard, something that’s been around for, I don’t know, 50? 100 years? I don’t know how long. I’ll look it up?

Matt: Oh, thousands of years.

Andrew: Oh, really? Okay.

Matt: Well, not formal billboards but outdoor advertising in general has been, you know, that’s as old as people with eyeballs in the real world.

Andrew: So then what’s an advantage of doing that?

Matt: Yeah, I think there’s a couple big ones, especially with the modern lens. One is that when people go online, they’re either using ad blockers or they’re super averse to seeing something imposing on their kind of personal experience on browsing the web or using the apps the use. So it’s in the real world. It’s not interrupting or imposing on that in any kind of private space. And then secondly, the pendulum has really swung way further back towards real world experiences. And so the data shows that the recall is highest without their advertising as compared to any other ad channel. So you reach people in an intimate kind of low defensive position. And then the recall and brand affinity is a lot higher because of that.

Andrew: You know what I find happens when I see a billboard? It feels like the brand is more real and has elevated itself beyond of online ads. For some reason, even though I knew Wix forever, I think I had the founder of Wix here, I’ve seen how well they’ve done. It wasn’t until I saw an ad for them that I thought, “Okay, they are a bigger player than I imagined.” I started to see them on the same level of Squarespace, where ordinarily, I see Squarespace is like way beyond on all those platforms.

You were working at Instacart. We talked before we started. That is one of the high flying success stories of Silicon Valley. Why leave after a couple of years instead of riding it out? You’re getting shares in a company that people feel is going to go public, going to get bought out? Why leave?

Matt: Yeah, it was kind of a combination of couple of factors. So I joined in the first, you know, 12 to 20 employees. So ground floor plus and we had an amazing ride. And my team in particular was at the tip of the spear for the company doing the new expansions, special operations, etc., and for a period of time, we needed to refocus back on actually getting our gross margin numbers in a better place before we did much more expansion. So our team was sort of given whatever job was basically convenient, not where we were going to be the most impactful.

And so that was kind of a bit of a, you know, the challenge was diminished two years in. I had half my invested and was already on a great pace to be pretty valuable. And I thought to myself, like, “Am I going to sit around and kind of be complacent on the challenge? Or am I going to take this other opportunity that presented itself,” which was starting a new program at Amazon.

Andrew: You know what? Why not say, “I’m going to sit around?” You’re getting paid shares that are valuable. You now know. You never know when you start a company at the size that you started whether it’s going to be the big hit or not. You had one that was a clear hit. Every month, right, they were putting money in an account, you’d look at your online whatever account you guys use and see more shares of this company that everyone is talking about, that’s clearly valuable. Why not say, “I’m just going to go for it. I’ll sit for two years.” What’s two years in a life that’s going to be 100 years?

Matt: I think two years is a lot.

Andrew: You do?

Matt: Yeah, so, I mean, if you thought about it, look, I’ve got half of a lottery ticket already, right? So it’s become a billion dollar company. If I’m sitting here making life decisions waiting for that other half of a lottery ticket, that’s not really how I want to do things. So I was already partially invested and it was already going to be a meaningful amount of money, I mean, if it ever gets liquid. And then I had a unique opportunity that I thought would kind of set me up for a career and a lifetime of anything I wanted to do.

Andrew: Let me say this just to be clear, now that I’m living in San Francisco, I get a sense of where people are coming from. I literally see people who’ve made it because they’ve been part of Pinterest in the early days, etc. We’re talking easily . . . if it goes public, easily another million dollars, right? Easily, from what your shares would have been worth.

Matt: Yeah.

Andrew: Yeah, let’s say a million additional. You’re giving that up because you saw a different path. It was Amazon. What did you think in 2016 that you were going to get out of working at Amazon? What was the thing you were going for?

Matt: It’s really kind of just seeing the other end of the spectrum. So I hadn’t done a failed startup and then joined a pretty wildly successful startup at the early stage. And I hadn’t really seen the other end of the business spectrum. So my curiosity and my kind of lack of challenge at that juncture at Instacart was combined to say, “I’m going to make this move.” I’m not necessarily even saying it was the right move. Maybe I should have been more patient at Instacart and six months from when I left, there would have been this amazing new experimental group that, you know, have been [inaudible 00:10:06]. You know, I saw it and I thought about it and I went for it.

Andrew: What did you learn? Is there one thing that stuck with you?

Matt: At Instacart or with . . . ?

Andrew: With Amazon. So you made that change to go work in Amazon. I’ve interviewed a few people who worked at Amazon, and they clearly learned a lot from being there. What was it? Was it something? And don’t feel obligated to say that you did. You spent less than a year there from what I understand?

Matt: No, I think it is kind of a great boot camp. And the biggest thing that sticks out to me is ways to communicate across hundreds of people who need to be moving in the same direction. So even a small team at Amazon is a few dozen. And then as you grow, you’re working with partner companies. So you’re learning how to run incredibly effective meetings, you’re learning how to hold people accountable because when in large groups, each person needs to know exactly what the others are doing. So honestly, I think they’re one of the . . . and they are well renowned as one of the best run larger companies. And so I learned it was a crash course in seven months of how to run a large scale business. And I wouldn’t have gotten that experience at Instacart where, you know, a large team at Instacart is probably 40 or 50 people. So I’ve done that . . .

Andrew: I’m looking at a list that I wrote as you were talking. How to run good meetings, which is really a skill that I’d like to learn that’s more valuable than most people realize. Accountability for team members. And then communication. Do you have an example one of those that you’re using today at AdQuick as a direct result of working for Amazon?

Matt: Yeah. I think the number one thing is date-driven mentality, where even in a one on one, it’s helpful. It’s like, “Hey, Matt, can you call that customer?” Most businesses and a lot of times people are just like, “Yes.” And, you know, it’s an ongoing battle endeavor, but it needs to be, “Yes. And I’ll do it by Wednesday.” So Wednesday, you and I know clearly, I did that. And you can expect that by Wednesday, as opposed to getting to Thursday and being like, “Yeah, you said you’d call them,” and I said, “Oh, I thought you meant just sometime this week.” I’ll call them and now it’s Friday. So that’s a micro example. But then you can extrapolate that out. And when you’re dealing with dozens of people, it becomes a lot more vital, and everybody knows when their deliverables are due.

Andrew: I’m writing that down by. You know what? It’s those little habits that make a company more efficient. Like, for example, an inefficient companies, even if I as an outsider work with them, if they’ll tell me “Let’s talk at 5:00,” they don’t take that extra step to save Pacific or Eastern Time or whatever it is, which naturally leads to confusion. And the little step of saying we’re habituated to add the time zone, for example, goes a long way to say we’re habituated to say, “Yes. And here’s the date that I’ll do it by,” goes a long way. How about for meetings since that’s something that I’d like to get better at myself?

Matt: Amazon meetings are amazing.

Andrew: What are they like?

Matt: Yeah. So, first of all, in any non-casual meeting, of course, there’s chit chat and, “Hey, let me grab you for 10 minutes.” But when there’s any meeting of call it four or more people, there needs to be an agenda. We also use that as AdQuick as much as we can. And then the beginning of the meeting is spent getting everybody on the same page. Amazon is famous for their memo-driven meetings where it can go from a one to a six-pager, a six-pager is a big deal. But everybody starts the meeting silently reading whatever meeting context has been written up. And it’s required at the meeting color to prepare that so that everybody doesn’t spend 30 minutes just even understanding what the hell they’re meeting about. You come in and 10 minutes of meeting, everybody is working with the same exact information and you can then have a super productive and the time spent is super productive.

Andrew: I like that they have them read it on the call. Most people, most businesses would think, “That’s inefficient. Read it before the call instead of wasting time.” Why do they do it on the call in the meeting?

Matt: That would require too much work from the people that are into meetings. So they give the very beginning of the meeting in order to get that context.

Andrew: I like that a lot because I don’t want to do homework before the call. If I’m here, we’re all doing it anyway. Let’s just spend five minutes reading this thing together. And you do that now today at AdQuick?

Matt: No, we haven’t gotten so much into the memos. I think we’re small enough and our meetings are small enough where it’s a little too much overhead but it’s definitely something where I want to kind of enact that at some point when we’re thinking about bigger decisions is the pre-req for bigger decisions and meetings around those is a memo of some kind of, again, do the same thing we did at Amazon.

Andrew: So where I presented this at the beginning of the interview is . . . and driving through city seeing billboards and I should recognize it as an opportunity to modernize it. That’s not the direction you came at it from. You actually came at it from a better direction. You saw a problem that existed when you were working at Instacart that you said, “I could correct.” And that’s where AdQuick came up. What was the problem and how do you see it?

Matt: Yeah, so as I mentioned, when I joined Instacart, a lot of what I did was expansion. So we were rattling off cities and try to grow geographically incredibly quick.

Andrew: You know what? I’m sorry, I should actually explain what Instacart is to anyone who doesn’t know. If you want to order groceries from local stores that happen not to have delivery people like here, it’s Mollie Stone’s in the Castro district, they don’t have their own online delivery thing. You go to Instacart, it’ll send your food over. I assume everyone knows it. But, okay. All right. So you were saying you saw a problem there. How did you experience it?

Matt: Yeah. So, you know, when we were setting up the new markets, we had a lot of different kind of ownership areas, hire local team, hire local shoppers, integrate with the grocery stores and then marketing, tell people who were there, right? So obviously, we’re using digital channels on the move to get to our advertising. It was a multiple week, dozens of phone calls. From relatively small buy, I remember in Indianapolis, you know, very little idea of whether you’re getting all available options, whether you’re getting a good price. And then when it actually comes to executing, it’s all bogged down in email attachments. So our ad actually went up late for the Indianapolis launch. I knew that there was a super . . . why can’t we just buy this online? Why can’t we buy it in a matter of 24 or 48 hours?

So that was the first piece. Then once we would get the campaign live, we’d actually anecdotally hear amazing things, customers saying, “Oh, yeah, I saw your billboard,” or the local grocery store owner who are our partners and say, “Oh, that’s so cool. Like we love the fact that you’re promoting it.” So we knew people were seeing it, remembering it, and was making its way back to us. Then we’d go to our next expansion meeting and with data-driven organization and we’d say, “Okay, how did Google work? Give us the data? How did Facebook work?” Great. We have all the data there. We get to outdoor advertising and our instinct was, “Hey, it worked. We heard about it.” And then it’s like, “Wait, how can we actually double or triple down on that channel, that ad channel when we have no actual data?” So that’s kind of the linchpin of AdQuick is that not only do we make it super easy to buy, we help brands actually quantify the ROI on this sort of nebulous, real world advertising.

Andrew: And so the way it worked before was what? Would you have to do it I said, which is see the logo of who the owner or the whoever managed that billboard is? That’s how it worked?

Matt: That’s how it still works to great . . .

Andrew: There was no clearinghouse offline [inaudible 00:17:31] even?

Matt: No. So that’s what we’re building is a digital way to buy any outdoor advertising.

Andrew: So before you, if I wanted to buy . . . I don’t think Turner still exists as an outdoor billboard. But if I saw Turner billboard, I forget the names of the companies. I see them all the time. And they’re memorable. But they’re not memorable, but they’re familiar.

Matt: See and you’d wouldn’t know who to call.

Andrew: I wouldn’t. Well, what I would do is I would have to drive past one of them and then look and then assume that if I call that one, they would introduce me to the other question companies too in the other locations. But that’s not how it worked?

Matt: Oh, no, no. So when you work at a, you know, media company A, some of the big ones are Lamar, Clear Channel, Outfront, but there’s 1,000, 1,100 plus media owners in the U.S. alone. And if you talk to one of them, they’re certainly not going to tell you, “Hey, you should [inaudible 00:18:15] editor for it. It’s either better location or better price than ours.” And that’s what AdQuick allows you to do is compare across media owner. And, yeah, I mean, the CEO of one of the largest, publicly-traded media A companies not so long ago said at some point, “When you work with us, you’re probably going to have to use a fax machine.” So it’s still pretty outdated in a lot of ways and we’re trying to help make that a better experience for customers.

Andrew: What about this? I’m doing a search for buy billboard ads. Like that’s how I would start if I wanted to. It’s kind of interesting that Taboola comes up as the first ad on Google. But I do see other companies, like I don’t know what this is or this Like are these companies that I could use to buy billboards everywhere?

Matt: Yeah, so each of them kind of has their own niche. Blip is digital only. I’m not sure about BillBoardsIn to be honest, but there’s a lot of kind of faux technology companies in the space. I think once you get past the first layer, and the customers see that, “Hey, this is basically a broker,” then you’d come to AdQuick and you can see the technology. It feels like an Airbnb or Expedia like experience. So we kind of let the product speak for itself. But there’s a lot of ways to do this, but generally, they’re not super friendly.

Andrew: Oh, I see what you mean. They’re asking me what city I’m in and then whether I want to buy the billboard or rent it. And then I think what the ones that I’m on are doing is linking me to the company that does it. Like they’re paid to introduce me to that company. Maybe it’s a lead. I don’t know how it works. Okay. So you saw that and you said . . . actually, before you saw that, how did you notice that this was a problem worth solving? How did you even pay attention to it instead of just writing it off and saying, “That’s just the way it works. I’ll stick with this other thing”? Why didn’t you ignore the problem?

Matt: Well, interestingly, I gave kind of the last catalyst start the company. But the prior catalyst is when I was working on a startup during business school. I actually tried to buy out through advertising in 2011 or ’12 and just realized how . . . I knew exactly the location I wanted to buy. I wasn’t in the market so I couldn’t see who owned it. And I was like, “Why can’t I find this easily?” Similar experience at that time, it was going to be a couple $100 spend. And I thought, “Oh, I’m a small fish, they don’t give a shit about me.” So that’s why it’s hard to find. Then it was kind of implanted in my head and I would follow it just in the background and talk to some people who own billboard companies and said, “You know, why doesn’t this exist?” And over that seven-year or so timeframe, I learned a lot and then coming off the Instacart experience, I realized, “Hey, we just took an offline industry essentially online. Why can’t we do this with another $40 billion of [revenue 00:21:13]?”

Andrew: Got it. By the way, that is the way to tell an origin story to not go into, “Well, there were all these different experiences in the past. They’re all kind of connected in this market.” Just tell me the one story and I understand that it encapsulates all the other experiences that come through. I like the way you explained it. And then always be open as an entrepreneur to say, “Here are the other experiences that help shaped this.” It’s not just epiphany but the . . . the moment that I’m using to express it that sounds like an epiphany is actually representative of much more experience.

All right, let me take a moment to talk about my first sponsor, then we’re going to go right back into this. My first sponsor is a company called Trainual. Let me ask you this, when you onboard people at your company, what do you do to make sure that they know what they’re doing?

Matt: Man, it’s an ongoing process and evolution. And especially because things change at a startup so quickly. Once you create an onboarding flow or document it changes very quickly, so it’s outdated very quickly. So, yeah, we try to keep up with that as best we can. But frankly, we probably don’t do the best job of it.

Andrew: I’ll tell you what we do. So imagine a situation like this. Somebody must have worked with you to book this interview with me. You’re going to come up with a set of steps initially for booking an interview with Matt, that should be put into the training manual for when that person is ready to be elevated to another role. Now you Matthew at the end of this interview might say, “Hey, you know what? It helps that I do have a mic. It actually helps that we are in a different room.” You’re going to learn a couple of things that are going to be really useful for you. It’s helpful if at the end of that process, you can go back to that list and say, “Here’s how we need to improve it, right? That’s one of the things that I love about the right manual, the right training thing, the right step, that the last step should always be, “Now record all the things that we could do differently.”

Like, right now you have a mic that we sent you. We bought it, we mailed it to you. You might say, “You know what? Andrew never thought to give me earphones, but I do think earphones would be better because then it keep my audio from Andrew from bleeding into the microphone, which should just be me. Let’s add that to the list. And from now on, we have a mic.” And that’s what a good training manual will do.

For us internally at our company, one of the things that we realized was . . . like you, we have a company culture that we believe everybody needs to understand. And I used to think they’d understand it. They just get it.

What I decided was we put it into our Trainual, into our manual. And so when somebody gets onboarded, there’s a set of checklist of what they need to do. One of them is go into QuickBooks and give us your financial for . . . not us. Give QuickBooks your financial information so we can pay you.” The other one is, “Fill out your tax paperwork so that we can make sure to not get you or us in trouble.” And I added into it, “Understand the principles that we operate by. Here are the six things. Just read it.” And what I wanted was some way to see that somebody that actually gone through and read it. And that’s what Trainual is about. Trainual will make sure that checklist is in.

And then Matthew, if you decide, “After this, I actually have to add a seventh thing, seven cultural points, seventh principle,” you can add it in and everyone Matthew who went through that onboarding process will get an alert saying, “Hey, actually Matthew just changed step number two. We all have to go back and read it.” If you want to do that. And so they could see when their stuff when their data is outdated because you’ve improved it, you’ve added a seven step. All right. That is what Trainual is about. It’s great piece of software. If you or anyone who’s watching wants to see the documents that we use, the process that we use to onboard people, the process I use to run my interviews right, you should go to Do you think it’s clear how to spell Trainual? Do you want to guess? I’m going to put you on the spot. How would you spell Trainual?

Matt: T-R-A-I-N-U-A-L. Trainual.

Andrew: Like training manual, combine into one, Trainual. I like company names that combined into one then you get it on the name. AdQuick. Mixergy kind of connected it. Yeah. So you’ll get to see that. You’ll get to see the software that’s being used by EO the entrepreneur organization, by Design Pickle, the company that’s really fantastic at getting designs. The Boring Company uses it. Think about that. What’s his name? Elon Musk’s company signed up for it and Mixergy. Got to Matt, you mentioned this company a couple of times that didn’t do so well. Which one was it?

Matt: There’s a company I started called Footprint Free.

Andrew: I was trying to figure out. What was that?

Matt: Yeah. So basically, I saw a lot of businesses struggling to either use recyclable straws or biodegradable utensils in their restaurant. Really, they’re just trying to say, “Hey, we care and we care about the environment.” And what Footprint Free was was a turnkey way for businesses to become carbon neutral. So basically, we would assess their carbon footprint. They would plant the equivalent amount of trees it would require to absorb that. And then they would be able to get more of an official brand that eventually people would recognize if we got to enough scale, which we didn’t. And then eventually, that people would start to kind of reciprocally spend money with those companies because they say, “Hey, I’ve got three choices of pizza joints, one of them is footprint free. I’m going to reward that business for being socially responsible.” A lot of it was predicated on critical mass, which it became clear that we weren’t going to be able to get to. But, you know, it’s kind of interesting 7, 8 years later to see all the different things that companies are still doing and where that’s evolving to.

Andrew: I get that. When I was looking it up I saw Footprint Free, Bike to the Beach in your LinkedIn profile. And I started to find, I guess, are you a cyclist? I think I found some of the bike races that you were a part of. I saw the numbers on that.

Matt: I have become one. Yeah.

Andrew: You are now. I heard you were competitive even as a kid. How competitive were you?

Matt: That’s probably one of my strongest characteristics is that if anybody wants to challenge me or play a game or, you know, a competition of any type, I’m in.

Andrew: Even as a kid?

Matt: What’s that?

Andrew: Even as a kid this was who you are.

Matt: Oh, especially as a kid.

Andrew: Give me an example of how that played itself out as a kid?

Matt: Oh, man. Well, I played sports pretty much ubiquitously. And then basically, when I was a younger kid and a little bit had a bit of a temper, the way to get me to do anything was just to challenge me or time me. I bet you can’t clean up your room in five minutes. I wouldn’t have done it without that premise. But once I got that, I was like, “Okay, I’m going to clean in three minutes. Let’s go.” So, yeah, a variety of ways.

Andrew: And so did you do the Fools Day criterium race? Is that you that I’m looking at?

Matt: I don’t think so.

Andrew: Tour of St. Louis, presented by Urban Chestnut? No, that’s not you, huh?

Matt: No. They sound good, though.

Andrew: It must be a different Matthew O’Connor.

Matt: Oh, yeah, it’s a relatively common name. The bike ride that I became a part of was called Bike to the Beach Show. It’s 100-mile ride benefiting Autism Speaks. So challenging ride, raise some money for autism. Autism Speaks in particular, and then we get to meet a bunch of great people. And it’s a pretty fulfilling challenge.

Andrew: I do find that just cycling for hours like that is really good for my mind. Noah Kagan put together this Sumo bike ride, which is 50 miles. I feel like it’s in a beautiful spot. I do feel he needs to go to 100. There’s something about hitting that 100-mile where you’re broken a little bit and you’re fully disconnected. And that’s when you really find the pleasure of the experience.

Matt: Yeah, you got to do . . .

Andrew: Doesn’t it help you to be so competitive now? Like does it help with AdQuick that you’re a competitive person?

Matt: Yeah, it definitely does. I think when kind of we have setbacks or we have a competitor, or somebody who’s claiming something. I think it really gets me kind of worked up. And I’m like, “Hell, no, we’re better than them. And if we aren’t now, we’re going to be better than them and here’s how.”

Andrew: Can you give an example of something like that? Even if you don’t mention the company name or this . . . well, I guess you could be specific about the setback, couldn’t you?

Matt: I mean, just the top of mine example is even at Instacart, every market we would go into there’s a dozen different kind of like grocery delivery players. And we would come in and say, “No, we’re way better. Here’s why.” And if we’re not better, and you know, at the beginning, we were not as good as we were at the end and it continues to improve. But we had a kind of competitive mindset of, “We’re going to take this industry over,” and not just for taking over but because it helps customers and people loved it and people wanted more of it. So that’s kind of a top of mind example.

Andrew: The first version of your site we talked about before we got started. I actually found the source code of it. So I see the software you use. Can you talk about what that software was? What’s the first version look like?

Matt: Yeah, so the kind of off-the-shelf software I used to basically just get customer feedback initially was called Sharetribe. It’s basically a white label way for somebody to start a marketplace of almost any kind. That’s kind of what their niche is. And so when I was still at Amazon, I was like, “Man, I want to start this company,” but it felt a little crazy. And this was a quick way for me to actually get more customer feedback and actually just test the concept of, “Hey, marketer A or B, here’s what the platform looks like, what do you think?” And I knew it sucked. But it was just getting that early feedback that even though I thought it sucked, a lot of customers are like, “Oh, yeah, this is cool. I can buy an outdoor advertisement in a couple clicks.”

So it was just enough validation that I could get off the ground really quickly, kind of de-risk some of the customer-facing aspects and not keep things in a vacuum, which I think a lot of people tend to do a little too much is like stay in stealth or not really get customer feedback early was way to get out there, even while I still had a another job.

Andrew: What was the problem with Sharetribe? I never heard of it before. But now that I see it, I like it a lot. Yeah, what was missing from it?

Matt: Flexibility. Like there’s so much nuance to getting into the best way to buy outdoor advertising, which is what I think we’ve built and are continuing to build. Things like varying dates, screen types, format types, workflow management around execution. So there’s so much that actually goes into executing an outdoor advertising campaign that it just isn’t supported by Sharetribe. If you want to sell like hats, you know, Sharetribe is great.

Andrew: Or even rent hats or rent surfboards from what I could see on their site. They’re built for it. But what I imagine they aren’t built for and tell me if I’m understanding right, I couldn’t use them to . . . you weren’t able to say, “Allow customers to search by number of people who would see the billboard or their demographics.” And then, of course, as I think you were saying, you wouldn’t allow us to be able to upload our ad copy and get that whole workflow going to get it published on a billboard.

Matt: Exactly. And I don’t think there are many large scale businesses that are running on Sharetribe. But again, it’s a great way to get to MVP. And if you want to rent surfboards in San Diego, you know, I think it’s a great way to create a digital presence for what might be an offline company.

Andrew: Now I see a lot of entrepreneurs that I’ve interviewed, just start with something off-the-shelf, and then eventually build something to their liking. Like the key example that I can think of now is Ryan Hoover from Product Hunt. He just used this piece of software that he found online, and that was his first version. But now they’re coding up like beasts over there, everything, just as beautiful. You told our producer, Brian Benson, who asked you, “Well, how did you get your first customer?” You said, “Basically, I was harassing anyone who was looking for outdoor advertising.” Is that the first part of the marketplace you went after or someone who had billboards to sell?

Matt: It was definitely the potential buyer. So I was pretty confident in the pain point just given the couple experiences that I mentioned being on the buying side, but I wanted to validate that with, you know, non-biased parties. And I’d say, you know, the mentality at the beginning of AdQuick was stolen directly from Instacart where beginning of Instacart, we had no grocery store partnerships, you know, we and they took the in store inventory. They went item by item, 20,000 items in the grocery store, scanned each of them, added the prices manually and created a digital storefront without the stores opt-in. They were then able to get that in front of customers who’s like, “Yeah, if I can do five taps on an app and click deliver, this is awesome.” So that was directly stolen from them is that when you get the side who’s actually spending the money, it’s a lot easier to double back and earn trust with the supply side. So that was the exact approach we took.

Andrew: Got it. And so you went and got customers. How did you find somebody? Who did you find? What was the path to the first person, the first business?

Matt: The course went right back to the friends I still had an Instacart who I said, “Hey, look, you’re launching in San Diego. Like just do one billboard. I’ll even sponsor and subsidize part of it. I just want you to go through the experience and hear about it.” You know, basically just told everybody, “Hey, I’m starting this company. Do you know, anybody that has any perspective on advertising, specifically outdoor advertising, I want to talk to them,” and just kind of scrapped and hustled my way to those conversations in the first couple of customers.

Andrew: Did you actually have to pay Instacart to buy the ads? Were you willing to subsidize it?

Matt: Subsidize. I didn’t pay them directly. I made it cheaper for them.

Andrew: To try it with you?

Matt: Yeah.

Andrew: Was this your own money or at that point did you raise money?

Matt: At that point it was my own money.

Andrew: It was, wow. And I got this note here from Brian that I don’t fully understand. You said you weren’t really . . . well, he wrote down, “They were not really worried about making money.” Who is that? Is it you not worried about it? Or is it clients?

Matt: No, I think that’s AdQuick at the very beginning was not worried about making, you know, margin or money. And so we just put things at the exact place that the media owner was charging and weren’t worried about making money. We were worried about proving the product, getting more customers. And so in our first and ultimately one of our, actually, our first and largest backers was Initialized Capital. So when we went to meet with them, the concept, the early team, some of the traction, and I asked Garry Tan. I said, “Garry, on the way out, on a scale of 1 to 10, what do you think of the company and the pitch?”

And he said, “If what you say is true, out of 8, 8 out of 10.” And I said, “Oh, okay. Well, what would make it a 10?” And he said, “A business model.” And I said, “Okay.” So the next week after that, we just added a transaction fee. And so immediately, we had a business model. And I wasn’t really worried about that from the beginning because I knew that when you’re the choke point of the transaction, which AdQuick does, it’s pretty easy to monetize service fees, promoted listings. And so I actually wasn’t too worried about that. And quickly, we enabled that once we had a good reason to, which was to get investment.

Andrew: How did you get Garry Tan? How did you get his interest?

Matt: So initially, basically, the Instacart network, they were actually investors in Instacart. So when they had a few ex-Instacart folks starting a new company, I think they were immediately interested. And then we had a bunch of favors from our old Instacart colleagues to say, “Hey, we vouch for these guys. We don’t know what the hell they’re doing, necessarily but we vouch for these guys and you should take a meeting.”

Andrew: He’s a neighbor of mine here in San Francisco. And I’ve been wanting to have him on for a long time because there’s so many entrepreneurs who I’ve interviewed who either within the interview outside of it have said that he was helpful in shaping the business itself. What’s an example of how he helped you beyond money?

Matt: Oh, man. I mean, at a very high level, being incredibly empathetic. He’s been a founder. And so even throughout the pitch, he listened. A lot of VCs tend to hear one tidbit about your company and they’re jumping into recommendations. And I’m like, “You don’t even know what we’re doing yet.” So he’s super empathetic. And then as far as anything we’ve needed around feedback or kind of check-ins throughout our process and in growing the company, he’s been incredibly open for any resources or feedback we need, taking meetings, introducing us to customers, really just a general resource across the board.

Andrew: He introduced you to customers too?

Matt: Yeah.

Andrew: Okay. Yeah, Initialized is it’s I think it’s better known for Alexis Ohanian, Garry’s partner. Alexis, the founder of Reddit. And for Garry his startup was . . . Posthaven was the one that he created afterwards. What’s the one before Postfull. It was basically Tumblr but . . . not before Tumblr but during Tumblr. And there was some issue with him and his co-founder that I’m dying to talk about. And, anyway, really fascinating.

Matt: Yeah. And Alexis is actually AdQuick board member. So we work with him all the time. But Initialized as a partnership is generally incredibly helpful and available.

Andrew: Yeah, Alexis now is known for being . . . who he’s married to more even then Reddit.

Matt: Yeah, it’s a nice pop culture reference now. Of course, everybody in the tech world already knew him from Reddit. But then more broadly for people not in the space, that’s definitely a high association.

Andrew: Yeah. For me, I don’t follow anything. Serena Williams, that’s who his wife is.

Matt: Oh, yeah.

Andrew: Yeah. And anything outside of tech or in business. I don’t know. She started like a big tech company. I might have known her but the rest of the world doesn’t know him as the Reddit guy. They know her. What else did you do to get the other side of the mark . . . ? Well, you know, let’s hold on that question. I’m curious about what you did to get the other side. Now that you had the clients, what did you do to get the old school suppliers that people had billboards on? But let me talk about my second sponsor. It is the COO Alliance. Do you have a second in command? What’s the title called your company?

Matt: Not necessarily second in command. Yeah.

Andrew: You don’t. Okay.

Matt: Yeah.

Andrew: It’s you mostly doing things right now?

Matt: Oh, no. I mean, I think it’s mostly the team. We’ve got . . .

Andrew: I mean, mostly like leading the team, leading the execution of the ideas. It’s still you doing that?

Matt: Sure. But I think the team does the lion’s share of the actual work.

Andrew: I get it. One of the things that I had was that everything was still coming back from the team back to me, back to me, back to me, and it was too much. And I talked to the founder and COO Alliance, Cameron Herold. And I said, “How do . . . ” I did an interview with him. “I do I even find somebody who does this?” And he did this interview with me where he helped me figure out how to find somebody who does this, how to make sure that they’re the right person, how to work with them. And I remember in the interview, I specifically said to him, “And like I have this idea. I just want to get freaking mics out to everybody on the team.”

And he said, “Well, this person is going to do it for you. Every interviewee will have a mic.” Actually the way he said it was, “And we’re probably going to get it to 75% of the guest’s hands and you’ll have to be okay with that.” And I thought that was so helpful for him to help me realize that if we get to 75, that’s a win beyond where we are right now. We could get maybe to 100 at some point. But, dude, just don’t freak out. Don’t make that person’s job hard. But basically, I had a vision, I needed people to execute it. I needed somebody to lead those people. And that’s where he helped me find them. What he does, though, having been the COO of a few of a couple of companies, including most notably 800-GOT-JUNK.

He took them from small time to big time. He’s known as the person who works with COOs, with the VP of operations, with second in commands and gives them the peer support of other COOs to talk to, the mentorship from him and others who are way advanced, the guidance, this collaboration, that’s what he’s known for. And when you eventually get someone who is a COO, when the person is listening to me gets that person, or if they have them right now, I urge you to go to and have them just see if it’s a good fit for them. Hit that prequalified button and see if they are qualified. You do need to have $8 million in revenue or beyond. You do need to hit a few minimum requirements.

But if you are, you could get to work with his network and get that support to become the best COO you can be. And again, if you’re listening to me and you’re a founder or CEO like Matt is, you could get your COO, your chief operating officer to be the best that she can be. And if you work with them, they will absolutely guarantee a 10X return on investment or your money back. If they’re not getting you to that level, they just don’t want your money and they will get you there because they’ve done it for so many other people. Again, go to You’ll be tagged as somebody who’s with this whole environment. And so they’ll understand that you’re somebody who probably is a good fit for them. But they’ll still make you go through some of the qualifications.

Matt: Do you want me to spell COO?

Andrew: You know what? You probably should only because I’m glad you repeated it because I wonder . . . I didn’t take elocution lessons. I’m just talking. I refuse to take elocution lessons. I’ll take lessons on like how to get people to open up? How to have interesting more personal conversations? But I am still like a New Yorker. Drive fast through the conversation and rip through words like they’re nothing. It’s not good. How do you get the suppliers?

Matt: Yeah. So I think the first thing was we focused on the demand side and making that experience really easy. Then as we got to a certain level of scale, we just went and met with the media owners and said, “Hey, first of all, why don’t you have software that you can send us to your customers with?” Okay, we learn that they’re using Excel, PDFs, local drives. So we said, “Okay, well, that’s a predicate to be able to create, send something quickly, it’s having it all online with software.” So we started to understand their use cases and then started to spec out that part of the product, so that we could build an MVP. And then we were lucky and kind of worked pretty hard to get one of the largest media owners in the country to switch over to start using our . . .

Andrew: Which one?

Matt: It’s called Regency Outdoors. So they’re . . .

Andrew: I’ve seen them.

Matt: They’re the Ritz Carlton of billboards, high profile, Sunset Strip, LAX billboards, and they were having a lot of issues with their internal technology. And so we basically just listened again to the customers on that side. And we do consider them customers, and said, “Hey, we can build you the system that will allow you to easily work with our system and also your direct customers.” And so they were kind of one of our biggest first wins on the media owner side.

Andrew: You know what? So that helps me really understand it because you’re right, they can’t list their properties on your platform if they’re keeping track of their inventory on software that’s not compatible. Great. Were they actually using spreadsheets?

Matt: We’ve seen pen and paper packets where we go into the media where they say, “How do you keep track of what’s available when?” And the person literally picks up pieces of paper and is like, “I’ve got it all right here.” And, you know, relatively old companies, they have no ability to build tech on their own. So that’s the exact same thing we saw at Instacart too is like grocery stores, we would work with them. And we’d say, “Hey, just upload what’s on your shelves and we’ll be done.” We learned they don’t know it’s on their shelves. So we had to build software for them to be able to work with the Instacart system so that our customers knew what was available on the shelves. Same analogy here in outdoor advertising. Without that software for the media side, it’s oftentimes incredibly difficult to even show customers what’s available. So we’re bridging that gap.

Andrew: Wow, that’s so helpful to know. It’s almost like OpenTable. They couldn’t allow you to book online until they gave the restaurants inventory management, which is that . . . That’s it.

Matt: You nailed it.

Andrew: And you were thinking along those lines too?

Matt: That’s the exact approach we’re taking. We don’t charge anything to use this part of the software. It helps their businesses. It helps AdQuick work more closely with them and ultimately helps AdQuick customers. So analogy a lot.

Andrew: That’s another thing that I’m learning from marketplace is number one, if you’ve got a two-sided marketplace, start by getting the people that have the money first and then the people who have the stuff to sell will be more likely to come. And the second is have a single player mode. Some reason for them to use your software without having to have the other side be available. And you guys have that and it’s free. Got it. Peloton was one of the early customers. How did you get Peloton on?

Matt: So initially it was we got in touch with them just honestly via an email. And they said, “Oh, good timing. We’re looking for a buy in Seattle.” And so they actually didn’t end up buying that campaign. But what they did was they saw the user experience and how easy it would have been if they bought. So then they started and they were doing retail store openings across the country. They’re looking in Silicon Valley and they’re based in New York City. So how do you find out what inventory is available there? Without AdQuick, it’s a challenge. With AdQuick, it’s super easy. So they started with small retail buys and then they scaled up to really significant spend as we scaled with them and their team. And now they’re about to IPO. So they were our first large scale customer. They trusted us. And I think we gave them a great customer experience. And they helped us learn a lot about what is the large scale customer needs. So they were an amazing win for us really early on.

Andrew: What did you do to go after customers? What was your process?

Matt: Oh, it was beg, borrow, steal. So pretty much experiment across the board. So find companies that we thought would be a good fit. Try to find warm intros, set up outbound email machines, set up relevant keyword targeting for five billboards.

Andrew: By good fit, you mean, were you looking to see who’s buying ads?

Matt: It was a combination of that and who should be buying ads? A lot of companies that should be using outdoor advertising extensively don’t do it at all because they don’t know where to start. They feel like they’re not going to get the right pricing or locations. And so there’s this sort of fear of the channel because it’s pretty opaque. So that’s who we also targeted and said, “Hey, you’re spending $50 million on TV. Well, you should be spending some of that in outdoor advertising.” And then we share the data about recall and showed them how easy it was to book on AdQuick. So you know, we’re still in an ever ongoing segmentation process. Who are going to be the best customers for us now and in the future. And early on, it’s really about trying a bunch of things and seeing what works.

Andrew: What did you look for that helped you identify who the right customers were to? And who were the right ones for you to spend time pursuing?

Matt: Really, it came down to learning the hard way in a lot of ways. So we still joke about a Michael Jackson Latino cover concert that we spent, like, two weeks trying to convert and they spent like $600, which is fine, you know, we don’t want to turn anybody’s money plus, you know, the input output there, the ROI on that effort is not there. So we started to say, “Okay, who are companies that should be doing outdoor advertising, relatively large budgets that are going to move the needle for our company?” And so we started moving up into more of an enterprise, later stage digital native company as our initial wheelhouse. And now that we have a much bigger team, we’re able to help with self-service the small customers as well as large fortune 500 companies.

Andrew: Yeah, you know, one of the things that we were thinking of doing was . . . so we’re getting into branding here for advertising on Mixergy. A lot of sponsors are just doing it to be connected. Billboard people in San Francisco would be a good fit. Well, let’s just send somebody out to go look at all the people who bought billboards in San Francisco, make a list of them, and then we can reach out to them because they’re clearly looking for a tech audience, and they’re doing branding. That became a little too involved. We didn’t need to do that. We found other ways. Did you do stuff like that? Did you send somebody out to go see who’s advertising on different billboards, so you can go contact them?

Matt: We did it ourselves. I mean, in the early days, we literally drove around LA and just took pictures of all the . . . I’ve been doing that in New York City this whole time. It was like I see an advert like, boom, they’re doing outdoor advertising. I wonder how they like their experience, if they’re going to be scaling it. So it’s a unique channel, in that, the ads are literally out there for everybody to see so you find out who’s doing it, and then AdQuick is particularly valuable when they’re looking to scale outside a lot of times what their home market is. So if you’re a New York City based company, you know, “Hey, I really want to be at the Union Square subway stop, because I know that’s right where my target demographic lives.” Well, what does that equivalent look like in Miami, Dallas, Chicago, LA, and San Francisco?

Andrew: So what’s your outbound sales process for recruiting them?

Matt: So we have a combination of outbound email, sales, team prospecting, and then customized campaign building that show them where are opportunities in the outdoor advertising world that they can extend their existing campaign. So using look alike campaigns based on what we know that on advertising, show them, “Hey, you’re targeting, you know, just use the same example, let’s say, the Marina.” Okay, so look, Murray Hill looks just like the Marina in Manhattan. So that’s where you should be spending, “Oh, and by the way, here’s the inventory is two clicks away, why not just do it through AdQuick?

Matt: You mentioned pricing that that one, Latino, Michael Jackson impersonator concert spent $600. I understand that in the beginning, you thought anyone could come in and buy any amount, even if it’s just a $600 purchase? And then at some point, you said, we’ve got to go up to enterprise? What made you decide to go up to enterprise? And how did things shift when you decided to spend more time on enterprise clients?

Matt: Well, it really came down to a lot of small businesses are essentially window shoppers. So for every hundred requests you get, 5 to 10 of them will actually convert. They’re just curious. So then we looked at, okay, how many of these small campaigns would it take to get us to nine figures in revenue, and just given the example I gave you, if you’re spending two weeks on a small campaign, you will literally almost never get there? So we started to look at, okay, what are the budgets of the right people? And how many of those will take us to get to the goals we had? Then we became pretty quick. Like that sounds quite obvious, but when it’s early stage, and you’re figuring things out, some obvious things aren’t as clear as they appear in retrospect.

Andrew: And so now, if I wanted to spend $600, I think as the example that you had, or $1000, I could still go in and do it.

Matt: Yeah.

Andrew: Now, I could.

Matt: Yeah. So now, we have a much robust platform, much better inventory access, and the user experience is . . . it can be self-service. So that’s part of going back down market is we initially started with trying to be a self-serve platform, we realized that there needed to be a better onboarding and some hand holding for companies spending millions of dollars in out of home. They want to talk to somebody and they wanted . . . you know, again, nobody knows who . . . not nobody, but AdQuick’s awareness is very low, so therefore, the trust is very low. So we needed to meet people in person, talk to them on the phone, and ultimately use technology to book it. Now, we’re getting a lot more trust and we’re able to have people spend a lot of money without a ton of hand holding through the platform.

Matt: Yeah, you know, I tried to go through your platform to see what it looked like and I couldn’t. As soon as I hit anything, I got, and it was a good scheduling system, actually, recognized the software. What I liked was that at the top, even though I use my throwaway email to go through the process, but you still said, “We’d love to work with Mixergy,” at the top of the site. And I thought that little touch, you understood this email address is connected somehow, I don’t know what software you use, but it doesn’t really matter, to figure out I am at Mixergy, and then pop that at the top of the page. And I think you guys use like Calendly or something to have me book a demo with someone on your team.

Matt: We actually just have somebody who types really fast monitor [inaudible 00:53:41] in the backend.

Andrew: Yeah, but . . .

Matt: But yeah, I’d say one point to make there is that we learned the hard way early on. We used to be just completely open, adding media owner rates, and anybody could browse any site. That’s eventually where I think we want to get back to, but the first couple . . . media owners are protective of their rates, they don’t want it publicly available, and they don’t want their competitors just to be able to know exactly what they’re charging, but we do have a verification of validation.

Andrew: Really, wow. Okay.

Matt: For the first time, we talked with the higher ups at some of the publicly traded companies was basically like a, “What the fuck are you doing?” call. “Take our rates and inventory off your publicly available site.” Then we said, “Oh, okay, good. You know, it’s kind of like asking for forgiveness, not permission. Great. Now, we know that’s a sensitive topic, and we’re going to privacy protect that. But ultimately, for any valid buyer, you’re going to be able to get access to any inventory you want.”

Andrew: Wow. Let’s talk about how you raise money, and then you had a co-founder?

Matt: Yeah.

Andrew: What happened with the co-founder? First of all, why’d you even get a co-founder? Why do you need them? And then we’ll talk about what happened when you raise money to one of the co-founders.

Matt: Yeah, I mean, so, I think everybody should have co-founders, to be quite honest. It’s going to help you focus on what you’re best at earlier. I’m not a developer, and we’re obviously a tech company. So I went to one of the guys, Fahim Ferdous, I became close with at Instacart. And he is a super entrepreneurial, and had a lot of the same ideas around the outdoor advertising space.

Andrew: And this is after you had that MVP, you got that person?

Matt: Yes. That’s correct.

Andrew: Yeah. Okay. So you had something in mind and then you said, “Okay, let’s get it.” Okay. So a co-founder who is developer. Who is the co-founder who left?

Matt: So this was a business school colleague of mine who ended up getting engaged and obviously subsequently married and moved to Atlanta, and had worked at McKinsey, and was kind of done with the road trip gig. And we were and all based in Venice Beach. And so for a combination of lifestyle reasons, he decided to move on and take another job in Atlanta, where he could stay put, you know, really kind of settle down with his wife. And so it was a really tough conversation and choice for him, I know. And then, you know, obviously, kind of tough for us. And so, yeah.

Andrew: Is he kicking himself right now for missing out?

Matt: I kind of hope so. Like . . .

Andrew: I think I got my answer in that inhale.

Matt: Yes. You got to stay there on until you’re vested, you’re three months away. You got to get this . . . we’re onto something here and just get here again, get your lottery ticket, and we’re going to keep working hard for you into a huge thing. And, you know, he’s not a hyper money motivated person. And he had to make the choice that was best for him and his family. And so I was pissed at him for a little bit, you know, but, like, we’re still buddies. And yeah, I mean, I hope there’s a little regret, but he’s happy and he had to make the right family decision. So I respect him for that.

Andrew: I’m looking at Ahrefs to get a sense of like what traffic is useful for you? What’s working for you? It’s kind of interesting how much the Medium posts are sending you credibility. And one of the top ones that comes up when I search is how to . . . something about where that is. “How AdQuick uses data to make outdoor advertising more ROI, Return on Investment driven.” What do you do to make sure that there’s actually an ROI? How do you measure Return on Investment from a billboard without slapping on every frickin’ billboard? . . . I don’t know what, right? How do you do it?

Matt: That would be a great campaign, by the way, so we should talk after the podcast . . .

Andrew: Really, I really don’t know.

Matt: The audience can hear that. But anyway, yeah. So it really breaks down to the three things. I think, more broadly, there’s more real world data created than ever before. And in five years, that’s going to be even more so the case. So with smartphones and smart technology, Bluetooth, etc. There’s more ways to . . .

Andrew: So what are you doing now to know that I looked at a billboard while I was on my way to work? And then when I got home, not even where I was heading. But when I got home, I looked at the website, or, frankly, that I maybe didn’t look at it for months. And then I finally went and looked at it. How can you tell these things work?

Matt: Yeah. So there’s three main ways. I think the most 100% attribution is text a short code to a number and get a response that only exists right there. And we’ve actually shown brands that are actually launching tomorrow at performance-based way to buy outdoor advertising. But it’s 100% attribution given the relatively low cost about their advertising, foreseeing real world acquisition be better than a lot of online acquisition, because online has become so expensive. There’s also another . . . so that’s direct attribution. And then there’s another big bucket called halo effect, which means what are people doing after they’re exposed to your outdoor advertisement? Are they going to your website? Are they more likely click your Google or Facebook ad?

Andrew: Right. How can you tell that?

Matt: So we integrate with the brands who have their own Google and Facebook data. And we track lift by specific market versus control group.

Andrew: And your software will do that?

Matt: Yes.

Andrew: Your software connects in with what they have, and then tells them, “Look, you’ve been running the same ads all across the country. But look, in this one region, we can see that more people are responding to the ads.

Matt: Exactly right. So we know that a portion of the outdoor advertisement is down to a lat long, we know who’s exposed, what time period, and we can track the impacts on website traffic, Google AdWords, performance marketing, localized brand awareness. So there’s more and more ways to do this. And then I think the other thing is that even five years ago, smartphone adoption wasn’t nearly as big, it’s about half of where it is today. Anybody can take an action right in the moment now because they have smartphones. So it’s more actionable in the immediate timeframe, rather than 10 years ago, you would basically have to remember the next time you were at a store, “Oh, I saw that brand of soda. And now I’m going to choose that as opposed to that competitor.” People can take actions right in the moment.

Andrew: And you were tracking that too by what? Putting the pixel on their site or looking at their analytics?

Matt: Usually with their analytics. So their website traffic, which we do have a pixel that lets us get more granular words. We know the particular zip codes and can do retroactive KPI settings. So we show increase click-through-rate, increase conversion rate, and therefore lower cost-per-click. So all these like golden metrics are actually improved without their advertising. And normally, that kind of disappears into the ether, unless you’re a hyper sophisticated outdoor advertising expert. There aren’t many because it’s such a small channel. So we’re making that data feedback loop turnkey, just by using AdQuick and you can set it up in a few clicks.

Andrew: No wonder you needed to have a tech co-founder or somebody who could build this out for you. Who’s the guy who does that? Is it Connor?

Matt: Connor is in sales, Fahim is our CTO and co-founder. And then we’ve added a few other actually, ex-Instacart engineers to join the team later on and then kind of have built out our engineering team based around those leaders.

Andrew: How was that for you to go into Instacart and take so many other people. Does that cause an issue for you with them?

Matt: Well, some had already left and done a quick stint on the other side. And, yeah, it’s not the best thing to do. We’ve only done it twice. So it’s not going to cripple them. They’ll be just fine.

Andrew: Yeah, they’re doing really well. Yeah, I’m seeing all these different content sites that are sending you guys traffic. So there’s TechCrunch, there’s Business Insider, there’s Fortune. I’m sensing what you’re doing is going after some media as a way of getting new customers and having people understand what you guys are about. Am I right?

Matt: Absolutely. And we’ve been scaling that . . . you know, we spent the first 18, 24 months kind of in a not stealth but not a publicly promotional approach. And now that are we know, our technology is best in class. Now we want everybody to know about it. So we’re starting to do a lot more vocal public facing ways to get exposure.

Andrew: And even just getting included on lists. Like, look at the freaking Ahrefs, it just keep sucking me in, “57 startups that will boom in 2019 according to VCs.” That’s a Business Insider article. It just includes you.

Matt: There’s a flow chip. Always start a company with the letter A because that list, it was ranked by priority. But obviously, if you look, it’s alphabetical. But we’ll take the first one there.

Andrew: And you do get into a bunch of different lists like that, which one of the things that I remember learning from a PR person was if you can get your company into those lists and just always be mentioned along with it, there’s more value sometimes and trying to work and get articles written specifically about your company. So if I decided like I remember talking to interviewing the founder of DuckDuckGo.

One of the big hits that he had in his traffic was is competing with Google. Nobody paid attention to him. He bought an ad that said something like, “We won’t track you unlike the other search engine.” And just by buying that cheapo ad, you got a bunch of publicity because, you know, no tech company, especially not a bootstrap operation like his got a billboard. Can we go into your platform right now and buy like $1,000 ad that just makes a statement as a way of getting PR?

Matt: Yeah. And I think one of the good examples tying a few threads here together is Alexis actually bought Serena a series of four billboards on the way to Palm Springs when she was coming back from her maternity and having given birth in sequential order. GMOAT greatest mother of all time. Given where it was located it was relatively low price. I wouldn’t suggest every boyfriend or husband go do that. But, yeah.

Andrew: What did that cost? What are we looking at?

Matt: I’d just say, a few $1,000.

Andrew: A few $1,000 under $10,000. That’s fantastic. Look at this, that’s a blog post on The Verge. “Alexis Ohanian welcomes Serena Williams back to tennis with four billboards.” Boom.

Matt: Yeah, SB Nation, yeah, it’s pretty . . . it went viral. It was on . . . . pretty crazy. Yeah, there’s a lot of companies who use outdoor advertising very strategically for the broader message. And one kind of interesting data point is that over a quarter of the U.S. population has shared an outdoor advertisement on their own social media. So that’s another thing we capture and quantify those ripple effects that are . . .

Andrew: How can you capture that?

Matt: Combination of image scraping and hashtags. So most people also don’t use the proper hashtags because they just want to share whatever the visual is but when is. But it booked on AdQuick, we know what the input image is and can recognize it in different angles, different lights.

Andrew: And you can even scrape it in Instagram?

Matt: Yeah.

Andrew: Because he posted it on Instagram. He used hashtag of “Greatest Mother of All Time,” GMOAT. He didn’t do anything to give you guys credit for it but you were saying your software would have scraped that if he hadn’t told you and you would have known that that’s what worked?

Matt: Yeah, if booked on AdQuick. Part of the flow is actually uploading the design creative you’re going to use. So we have that input and can recognize any similar image on social media.

Andrew: So weird too now he’s Alexis Ohanian senior. I always think of seniors being like these old dudes, not the founder of Reddit who’s goofing around with billboards. Wow. Wee. All right, we’ve learned a lot here today. Number one, we learned that all this old media stuff that we might roll our eyes on is actually something that is a little more valuable that we should be paying attention to. Number two, there is still old media that we can modernize. Number three, start with whatever is available out there. In your case you used Sharetribe to white label your marketplace.

And number four, whatever number I’m on next, whenever that software is going to have to be super customized to a level you wouldn’t have anticipated. I would not have anticipated that you went into these. These are big boys with big businesses that are old school, and they still are using paper and pen to keep track of their inventory. I wouldn’t have anticipated and so you have to go back and recreate the basics for them, which is inventory management.

All right, I want to thank you for doing this interview. Anyone who wants to go check out your website and maybe buy an ad saying, “Thank you Matthew O’Connor for doing an interview on Mixergy.” Let’s be honest, it’s not going to be it. But whatever the ad is, go check out I like how there’s room to grow. There doesn’t say Billboard Quick, it just says AdQuick. I can see you guys getting into all. You’re thinking that right from the start, weren’t you?

Matt: Yeah, we don’t want to be too pigeonholed. So, yeah.

Andrew: And like right now you’re going after outdoor advertising. I can imagine in the future who knows what you’ll be on. But the company has the software now to allow like let’s suppose sleeves on coffee cups took off as a thing. You guys, right? You can measure success on that, measure an ROI. Having the software to let us buy it. That’s the hard part. I’m a little too excited about your business. Freaking Garry Tan, super smart guy.

All right, so that’s that. I should also thank the two sponsors have made this interview happen, especially since they’re brand new, and they’re probably sitting around trying to figure out, “Is this ad actually working with Andrew or not?” They do have highly trackable ads. So if you guys would do me a favor and go to and look to see if that is the right software for you to train your people. Or and see if that’s the right fit for your second in command. You would be doing me a solid and frankly you do yourself a solid.

And finally I did mention Gabriel Weinberg of DuckDuckGo. I’m super proud that he did a course with us. He got a lot of traction using techniques using like billboard, which, again, people don’t think about. And one of the things that he taught me was Andrew, look at these things that you don’t think about. Oh, he had this whole process for how to do things like that to look at billboards, look at in person, look at booths at conferences. How do you go through all these things you wouldn’t considered as ways of getting traction, as ways of getting customers, put it in organized way and then go and target the ones that makes sense for you.

It’s called “Traction” and he wrote a book on it. I highly recommend the book. And if you want to see the course that he did with us, go to, and you will get the course where he taught us and we produced the heck . . . I’m actually going to say the word heck to try to be a nice guy. And I want to say how. We produced the heck out of that course to make it look really good and give you everything you need. I’m super proud of what we’re doing at Mixergy Premium. All right, Matt, it’s been great talking to you. You’re an easy guy to talk to.

Matt: I had a blast. Thanks for having me.

Andrew: Thanks a lot. Thanks. Bye, everyone.

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