Maximize Your Out-of-Home Advertising

Hosted By Matt Watson

Full Scale

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Sam Mallikarjunan

Today's Guest: Sam Mallikarjunan

CEO and Co-founder -

Boston, MA

Ep. #1004 - Out-of-Home Advertising

In today’s episode of Startup Hustle, let’s talk about out-of-home advertising. Matt Watson shares the mic with Sam Mallikarjunan, CEO and co-founder of Our guest’s company is included in the Boston top startups list compiled by Startup Hustle. Learn how a new tool for advertisers can help you become more efficient and sell more out-of-home ad spots.

Covered In This Episode

Tools and technology can be your best friends in selling more. That is why every business owner should know about emerging tech that makes advertising easier. This is especially true if you’re delving into out-of-home advertising strategies.

So Matt and Sam are here to help you with that. They talk about how can help with your out-of-home advertising campaigns. Moreover, they also dive into the best advice for entrepreneurs regarding advertising.

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What are you waiting for? Discover vital advertising notes in this Startup Hustle episode now.

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  • Sam Mallikarjunan’s background as a founder (01:54)
  • What is capable of? (05:11)
  • Examples of out-of-home advertising media (06:05)
  • Random fact: Missouri had more billboards per mile of highway than other states (08:39)
  • Advertising costs of billboards versus digital marketing (12:20)
  • How to track impressions for billboards (14:28)
  • How the AI in works (15:49)
  • The startup journey (18:09)
  • Educating the market (19:57)
  • Why is direct mail a dying medium? (21:53)
  • Being efficient in reaching your target market (23:59)
  • Building the tool for advertising companies (25:49)
  • How giving away FREE tools creates a network effect (27:56)
  • Fear in the out-of-home advertising industry (29:50)
  • Automating work in terms of availability and scheduling (32:01)
  • Creating change in any industry (32:59)
  • Advertising on TV (33:59)
  • Targeting ads and privacy (35:51)
  • The future of (36:50)
  • Advice for entrepreneurs (40:27)

Key Quotes

AI, in the real world, is much more complicated. Is there a tree in front of it? If it’s raining, your Facebook ads don’t stop working. But your billboard campaign might be impacted.

– Sam Mallikarjunan

When you’re first to market like that, it’s not something that people buy. So it’s like you have to create the market, which is its own challenge.

– Matt Watson

But the lesson I have learned so far this year is that let’s first focus on executing in the $40 billion global out-of-home market. And then we can tackle the 80-billion-dollar sports market, events, market, direct mail, and everything else like that. You don’t do everything at once.

– Sam Mallikarjunan

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Matt Watson 00:01
And we’re back for another episode of the Startup Hustle. This is your host today, Matt Watson. Today, we’re gonna be talking about, well, marketing but not digital marketing. Are we talking about marketing in the real world? With Sam’s company, Sam Mallikarjunan with We’re very excited for them to be one of the top startups in Boston. We have a whole series about the top startups in Boston. If you check the show notes, there’s a link to all of them if you want to check out all the companies. And before we get started, I do want to remind everybody that today’s episode of Startup Hustle is sponsored by Equip-Bid Auctions. Your Midwest online auction marketplace to buy and sell stuff. Equip-Bid provides dedicated support to affiliates in Kansas, Missouri, Nebraska, and Iowa. Join the team and sell everything from heavy machinery to home goods, vehicles, and boats to restaurant and kitchen equipment and tractors to patio furniture. Go to for details. Or just click the link in the show notes. Well, Sam, welcome to the show, man.

Sam Mallikarjunan 01:11
Thanks for having me. I’m looking forward to it.

Matt Watson 01:13
Congrats on being one of the top startups. From looking at your background on LinkedIn, it looks like you’ve worked at a few startups before.

Sam Mallikarjunan 01:23
Yeah, I’ve spent most of my career in startups, which is, you know, questionable decision-making. But it is happy to hear you all doing an episode on Boston. I think Boston is a dramatically underrated startup city. And happy to see, you know, Boston startups getting recognition.

Matt Watson 01:41
Absolutely. Well, I guess to get started, once you tell us a little bit about your background, your startup background. Your entrepreneurial journey.

Sam Mallikarjunan 01:50
I actually grew up in Florida, near Kennedy Space Center. So moonshot was not a metaphor when I was growing up. But then, I moved to Boston and actually worked for a couple of HubSpot. Not having a college degree or any experience, I didn’t have high hopes for it. So I built a website called And ran ads targeting people who worked there to register for the free webinar and why you should hire me. Now, this was before Account-Based Marketing was like a jargon term. But it was basically what I was doing. It was a blast. I mean, when I joined, we were small, and nobody knew about us. Now, you know, obviously, they’ve been very, very successful. They’re an anchor company in Boston. I got to run our expansion into Latin America on the marketing team. Then I was the head of growth at HubSpot labs and taught at Harvard University for a while, which was a lot of fun and gave me a lot of respect for teachers. They are really being good at something and are able to teach it. Yeah. Oh, yeah. And then, yeah, after that went to a company called Flock. So we decided to fight Google, Microsoft, Facebook, and Slack at the same time. That ended about as well as you can think. Yeah. And then started this company by accident, which I know sounds weird, but it was originally a hackathon. HubSpot alumni help business owners make money in different ways. During the COVID lockdowns, we’re like, what if there was a Google Display Network for the real world? So we built the prototype, and we handed out the giant check. Like, you actually can buy those, by the way, you can buy giant checks and, like, hand them out.

Matt Watson 03:26
I’ve always wanted one. I’ve always wanted one of those giant checks. Can I get those on Amazon?

Sam Mallikarjunan 03:31
You can probably get them on Amazon. I actually think I just Googled print giant or something like that. I assumed there would be a website that did that. And then, yeah, my now co-founder was working at Simon Property Group. And out-of-home or offline advertising is not really anything I’d ever done. I bought billboards twice as a marketer, and once was just to piss off a competitor. And so I knew I didn’t really understand the space. And as we dug into it, it turns out it’s insane. It’s the only traditional ad medium still growing. It’s run on spreadsheets and post-it notes. We actually do a reverse stealth mode. We called all the people who would normally be competitors and told them we were planning to do so yeah. We went from a hackathon to help, you know, my barber in Boston, Larry, if you’re listening, make money off of only being able to fill half his chairs to saying what the world needs are an integrated marketplace for media that’s not on the internet.

Matt Watson 04:31
So we’re talking about, your company, today. And if I understand this correctly, are you guys primarily helping people advertise on digital billboards? I mean, we don’t. We don’t see a lot of digital billboards, at least where I live. There are some there are not. There’s not a lot that you guys are focused on, specifically those or are there other types of mediums that you’re doing display ads on?

Sam Mallikarjunan 04:54
We do. Everything digital is about 3% of the inventory. And easy, but arguably less interesting. Okay, we’ve had people wrap cars, we’ve had, you know, led trucks. We’ve had people hold projectors and stand outside of conferences. Like there’s a lot more than just okay. It was not just digital billboards. Yeah, digital, not just digital, not even just billboards out of home is, it’s fun. It’s most fun doing marketing since social media.

Matt Watson 05:25
Well, and so you mentioned a few different types. And you know, even if you go to, like, Las Vegas and stand on the strip, you see, like, cars drive by with signs on them and stuff like that, right? Like, there are a lot of different kinds of this type of advertising. But you’re saying before, as a potential business that wants to advertise on those mediums, it was hard to know how to advertise and how to find opportunities. And your goal is to be that marketplace to kind of get it, you know, get the advertisers together with the people who won’t, the majority of it. Yeah.

Sam Mallikarjunan 06:03
So that was something else that was surprising to me because, again, like coming from a primary internet marketing background. Nerds, like may have spent 20 years optimizing the internet and ruined it for everybody. It’s quite hard to break into marketing, just using digital channels now. And it’s not. Like Clear Channel out front. Lamar owns all the inventory, the names, you probably know, right? The majority of the inventory is owned by, like, you know, the family near where I live. Her name’s Debra, she’s lovely with her, and her family is on 15 billboards. So the first thing we did was just like, create a directory so you can find who owns what and where, as shockingly, didn’t already exist. That didn’t exist. No, it didn’t. It was what we actually had to do, like freedom of information requests with state permit websites and things like that, to try and just assemble a database, the most comprehensive, the only comprehensive database of just who owns what and where much fewer data and analytics and stuff.

Matt Watson 06:59
So, how did they do this before? If I’m McDonald’s in Boston, and I want to do 20 billboards across Boston? Did they just call Lamar and just deal with them? And if Lamar didn’t have it, that was just kind of the end of the process?

Sam Mallikarjunan 07:14
Yeah, exactly. I mean, if you’re a big enough company will work with an agency. But even those agencies are still going to work with a small number of companies, right? Like Florida, where I live. Now, because it’s cold in Boston, we’ve got like 16,000 billboards owned by 100 Different companies, like you’re not going to call 14 Different companies to put together your campaign, which is part of the software automation that we have to build like how do we build that integrated ecosystem? So that, like, peanut butter and jelly, some things are better one, so sold together. And the beloved missing out like McDonald’s just wouldn’t have known that you know, certain inventory exist is an option.

Matt Watson 07:59
See, I thought I heard this one day, and I think it’d be an interesting random fact. I was told once that Missouri had more billboards per mile of highway than any other state. Just curious about any idea, the random fact of where the most billboards are in the country.

Sam Mallikarjunan 08:17
I could look that up in the database, but I have not looked up that particular stat. I’ve got a lot of fun stats, like the billboard that you can use to reach Elon Musk or the billboard people drive past to go to a liquor store and then go to work. But I don’t have where there are the most billboards per mile. That’s new.

Matt Watson 08:33
I think it’s Missouri. And I think it’s partly because Missouri has more, more highway miles than any other state for whatever reason. There are just a shit ton of highways in Missouri because we’re in the middle of nowhere. So there are just a lot of highways here.

Sam Mallikarjunan 08:47
But there’s a lot of I don’t know why everybody’s in such a hurry to get somewhere.

Matt Watson 08:52
I love driving through there driving through. So. So I think I think that it’s interesting that there’s never been a good inventory model for the billboards. And I guess if you own a billboard, is it just like a random place along the side of the street, and they decide to put up a billboard, and then they gotta go through the hassle of trying to get somebody who wants to advertise on it, and they end up contracting out through somebody like Lamar? Is that what they usually do? Or how does that work?

Sam Mallikarjunan 09:22
No, most sales have been local. It’s actually pretty akin to, you know, Airbnb, almost, right? Like there was a lot of inventory that was just not accessible. If you know, you could build a hotel but without Expedia or Google travel and stuff like that. People had to drive past it or be local to know it was there.

Matt Watson 09:43
So those billboard owners aren’t monetizing that asset very well. Right. So by listing their asset on your platform, all of a sudden, they’ve got a distribution channel that they really liked before.

Sam Mallikarjunan 09:57
Yeah, so about half of the out-of-home inventory goes unsold, and at any given point in time and the inventory that is sold probably sells for about half of what it should, on a CPM basis. The marketers listening to this would be like shocked at how cheap it is compared to display or CTV or some of the things they’re used to thinking of.

Matt Watson 10:15
So what is so what does it cost to rent a billboard for a month? Usually?

Sam Mallikarjunan 10:20
The answer to that is. Obviously, it depends. There are some places where it’s, you know, 250 to 300, or $400, to get a billboard for a month, maybe some of those ones in Missouri you’re talking about? Or if you want to be in Times Square, that’s, you know, we can do that. That was really expensive. We try to encourage people not to do that. It’s more about the audience, right? Like, what audience do you want to reach? And then what’s the most cost-effective way to reach them? Usually, the answer is not San Francisco, Los Angeles, and New York, where nobody wants to run, but you know, people live elsewhere. I dropped you again. I can’t hear you. This is a day for technical gremlins. I lost you there.

Matt Watson 11:30
Sorry. Yeah. So let’s just keep going. I’ll ask the same question. And we’ll edit it together. Okay. Sounds good. So, you mentioned that advertising on billboards is cheaper than then people would think, you know, compared to digital marketing. So what does it cost? You know, kind of type to advertise for a month on a billboard? I’m sure.

Sam Mallikarjunan 11:55
It’s totally different if it’s Time Square versus rural Missouri somewhere, but yeah, it totally depends. Again, it’s a lot like planning a vacation, you know, how big do you want it to be? Where do you want it to be? New York, San Francisco. Great. There are lots of people there. Turns out people do live in other places. I spent a fair bit of my time convincing people not to try and run their first ever out-of-home campaign and America’s most expensive and America’s distracting city. But I mean, as you mentioned, you know, some of those billboards in Missouri might cost 250 to 300 or $400 a month, all the way up to, you know, I think the NASDAQ sign or something like that’s probably like 20 grand for, for 30 minutes. So, it depends. It depends.

Matt Watson 12:37
Yeah, imagine any idea what it costs for a giant screen, and like Times Square, I can look it up. It’s usually, depending on when you’re trying to do it and things like that.

Sam Mallikarjunan 12:42
You can, it’ll be in the 20 to $30,000 range, just to like, be on there and take a selfie with it out of home is cool. By the way, it’s the only ad medium where like, it’s also content. You know, like T mobile’s commercials or have their own billboards, nobody does commercials with their Facebook ads in them. But to do an effective campaign that’s not just for flash in New York City would be a lot more expensive than to do it, for example, in Dallas, Miami, or Chicago, so you can definitely do it. I’m not saying don’t do out on advertising in New York City if that’s where the audience is right for you. But don’t just do it there because you’re used to seeing it there.

Matt Watson 13:29
So, do you guys, as part of this database that you’ve built and know the inventory of all this? How do you guys measure, like you’re talking about like CPM, then how do you track like the number of potential eyeballs that would see this? This particular billboard? Like, how do you get a sense for that? How do you measure that?

Sam Mallikarjunan 13:48
Yeah, I don’t know how nerdy the audience is and also how old the audience is. But if you remember Google’s original PageRank algorithm, where they try to rank websites based on inbound links, we do the same thing with something we call place rank. Where if you want to reach people who work at hospitals in Pittsburgh, which was a real campaign we did, which billboards do people who work at hospitals in Pittsburgh tend to drive past if you want her to who work at HubSpot, if you’re a b2b ABM marketer, don’t buy an add on I 95 Because nobody who lives in Boston is actually taking that road to get to work. They take McGrath Highway. So it’s a combination of, you know, data that are usually used by commercial real estate planning and governments to understand like groups of people and how they move about a city. That same data just applied to, you know, if you want to reach people who drink urban and our C suite executives at tech startups, you know, as all that data exists, and then just how can you be present in their journey is what the play strike algorithm tells you how do you decide where to run to be part of a literal buyers journey? Not a metaphorical one.

Matt Watson 14:59
So it is that part Because of the AI that you guys have built or an algorithm, or what would you call that? That definitely sounds like that’s got to be a secret sauce that you guys have invented.

Sam Mallikarjunan 15:09
That is the AI in And also, for the startups listening, don’t launch a startup; if you can’t find, just make up a nonsense word. Otherwise, you have to say dot, whatever the TLD is, every time or if you will go to Yeah, so that’s, that’s the AI that we have, right? We ingest data from all of these different sources. And, you know, Facebook makes it look so easy. But their AI to help you get on the right screen at the right time is pretty complicated. AI, in the real world, is much, much more complicated. Is there a tree in front of it? If it’s raining, your Facebook ads don’t stop working. Your billboard campaign might be impacted. Or again, the joke I made earlier, reaching people at the right time when there is one liquor store in Boston, there’s 3% of people who go there, and then go to work. I’m super excited to find out who they are. But in general, so that advertisers like, okay, don’t like retry, plan your campaign around reaching people when they’re on the way to work. So it’s, it’s a really, my co-founder, Greg, doesn’t think that should be allowed as a sentence.

Matt Watson 16:14
It’s a really fun math problem. Actually, it is very cool to be able to play with the data and look for weird, you know, weird things, anecdotes, that anecdotes that come out of that. So that would be fun to do. I imagine.

Sam Mallikarjunan 16:25
That’s the Elon Musk of what I always talk about because I grew up near Kennedy Space Center. So there’s kind of only one road in and unless you work for the Air Force, and he doesn’t. And so, like you’re not going to get him on Facebook ads, but there is a billboard, you could drive fast that he has to drive fast to go in there.

Matt Watson 16:42
And I’m like, that’s just SpaceX. Yeah, as some SpaceX employees would see, they’d have to see.

Sam Mallikarjunan 16:48
Yeah, or NASA or Boeing or whatever. Right now, I think the last time I looked, there was a local home medical equipment company on it. It’s like electric wheelchairs, very on-brand for my home state of Florida. But there’s probably somebody who wants to advertise to like NASA and Boeing and SpaceX or tech. I just want to buy it and say hi, Ilan, or something, please.

Matt Watson 17:08
I feel like, yeah, I was gonna say, I feel like there’s a great joke there for $8 on a blue checkmark somewhere.

Sam Mallikarjunan 17:15
That’s good. That’s good. We should do that.

Matt Watson 17:19
Now pay me my $8 blue checkmark.

Sam Mallikarjunan 17:24
I’ll donate 8.8 dollars worth of trees every time he drives faster.

Matt Watson 17:29
And there you go. So tell me a little more about where you guys are in your, in your, your journey. As a startup? I mean, have you guys really been in the growth phase? Are you still kind of early stages of figuring all this out? Or the kind where are you guys at in your journey?

Sam Mallikarjunan 17:44
So we were seed stage. We’ve raised just shy of $10 million, mostly from Boston VCs, who got it. We got a really great VC community in Boston now. The team is just over 50 people so it’s grown quite quickly. The interesting challenge for us is when you’re going into an industry where there’s not that much competition like online, there’s a 10,000 market. Startups, right? There are like 60, offline mahr tech startups on the landscape. And we thought we were going to come into this and start fighting Facebook with machine learning. We can and we will, and we do. But you can’t sell cars in the country without roads, right? Even if it’s a self-driving AI car. So that’s where we realized we had to actually take a step back and like, build a directory of who owns what and where build a tool that allows you to, like get availability and pricing easily. You know, so that’s been the big learning for us was, our backgrounds are primarily on the internet, we’re used to integrated ecosystems with 100 other companies doing basically the same thing you do for any startup you’re doing. To come into an industry where there are not a lot of techs, not a lot of startups, but it’s still growing anyways. Right? And then to, you know, I’ve basically got Tesla engineers laying asphalt right now, trying to do basic things like building a database of billboards sizes and dimensions so that you can print more easily and more quickly.

Matt Watson 19:17
Well, you know, it’s always good to be first to market, but in some sense, it’s not necessarily great to be first to market or create a new market because people also don’t necessarily buy it or don’t know to buy it, or they don’t know the market exists, right? It’s, I mean, luckily Lucky for you, billboards aren’t a new thing, so people are familiar with them. But if people aren’t used to advertising with them, or they’re not used to being able to do this, it’s like you have to go re-educate the market like that’s the problem is you have to educate the market that you exist, because people aren’t used to buying you whatever the thing is right necessarily you guys but when you’re first to market like that, nobody it’s not something that people buy so it’s like you have to create the market which is its own challenge.

Sam Mallikarjunan 19:57
Yeah, for everybody who aspires to be a category creator, I assure you, it’s not nearly as much fun as it sounds. No. It’s almost harder, actually because people know we were doing inbound marketing at HubSpot, which is where I was back in the day. Like I had to explain to CEOs what a search engine was before I could sell them SEO software. Right. Twitter was something your nephew. Yeah, not like serious businesses. The challenge is that homeless people actually already think they know what it means. They think they know where it fits in the acquisition strategy, and the marketing strategy. One, it can be anywhere in the funnel. You can drive website traffic and app downloads anything else as well as brand awareness. And it never occurred to me to wrap an ice cream truck in branding and park it in the parking lot of the company I’m trying to sell to, right like I’ve, I’ve actually kind of mad I didn’t know about out of home earlier in my career, because going after Salesforce users at the Dreamforce conference is a lot easier. Where you could just drive a fleet wrap a fleet of cars and drive it around the event than when you’re trying to compete and all digital channels.

Matt Watson 21:05
Do you guys do anything that’s related to like direct mail kind of stuff like campaigns that way to know?

Sam Mallikarjunan 21:13
Our product manager David literally asked me this question on our one 190 minutes ago. Why don’t we expand because there’s also like sports inventory events, there’s so much overlap in that direct print and some of those other things, those are kind of dying mediums, I think what I like about out-of-home is it’s the only traditional medium still growing. So. But the other kind of thing that I’ve learned this year, is only trying to do one really hard thing at a time. We tried to add in sports and events, because a lot of the same advertisers, you know that MGM uses our platform, and they also do sports advertising. They should be able to do it all in one place and not have to make two phone calls. And they have the same problems, right? Major League Baseball, you know, is using like a hack-together solution, you know, for their ad sales reps. And you got to call all the different stadiums if you want to buy it’s a significant challenge. But I think my answer to that is I have an aspiration, to make it so that whatever marketers want to buy, whatever is appropriate to reach their audience in whatever context on whatever screen, they can do it on That’s the joke. But I think the lesson I have learned so far this year is, let’s first, you know, focus on executing in, the $40 billion global out-of-home market. And then we can tackle the $80 billion dollar sports market, the events, market, direct mail, everything else like that. So well, you don’t do everything at once.

Matt Watson 22:48
Yeah, yeah, absolutely. Well, you bring up a good point about stadiums and forget like NFL and MLB stadiums for a second. But there are 1000s of other stadiums from like my kids my kids play soccer every Saturday, right? And they have billboards and little ads and stuff around the soccer fields and stuff. Right? Like, potentially, though, that’s the kind of inventory that’d be great in there. And you’re like, how do I reach families with young children like boom, this would be the perfect place to advertise. Right. So that makes a lot of sense to me.

Sam Mallikarjunan 23:19
Yeah, I mean, going back to the NASA metaphor, again, just because that’s where I am right now. There’s the local high school here. They’ve got those, but it’s the barber shop and the dry cleaner. It’s not United Launch Alliance trying to reach NASA decision-makers right now. They’re there for their kid’s game. There’s cooler stuff, too. There’s a company called League side that actually lets you sponsor youth sports teams.

Matt Watson 23:44
Yep, there you go.

Sam Mallikarjunan 23:46
Were like, and I think that’s, that’s super cool. That’s one of the reasons I’m excited about doing this is like, the kind of the premise was like, how would it change the world if the most powerful marketing medium on earth wasn’t Google or Facebook, but it was like physical places, it was local spaces or small businesses, like my local high school should be making 1000s of dollars a month more in additional ad revenue than they are? And that’s like, something you can feel good about, right?

Matt Watson 24:11
Yeah. Every high-level stadium. Yeah, every high school football stadium and gym there is gonna have ads on it. Yep. Well as a reminder, today’s episode of Startup Hustle is brought to you by Equip-Bid auctions, an online marketplace dedicated to growing small auction businesses. They’re solving problems and providing a fun re-commerce or liquidation shopping experience to valued bidders. Go check out their incredible offerings and sign up at So one of the things you talked about going early on in the space is like, the data that you needed, wasn’t there, and one of your challenges was figuring out how to integrate all this together. So I’m gonna guess you had to go to companies like Lamar and these guys and try To integrate with them. And, you know, first calling them up and saying, Hey, give me all of your data, probably didn’t go very well that.

Sam Mallikarjunan 25:09
No, it didn’t, because they don’t actually muscle. Companies don’t actually have that data. By the way, side note re-commerce, brilliant, tight, like a one-liner, your sponsor, just as a marketer, I respect that, that term they’ve come up with regards. But to answer your question, you know, again, like being humble coming into an industry, I, a lot of the reason tech startups that have come in and since you have failed is they’ve had a mentality of let’s do things the way we did on the internet. There is a role that a lot of companies call the Chartist. And that’s the person who owns the whiteboard that has the availability and pricing of all the billboards in that particular region. And like, it’s not like there was a database that we could integrate with. So there’s one of the things we did was we built a free, you know, SAS platform for people to manage their inventory availability and pricing, not using spreadsheets and post-it notes, which, you know, most companies are doing. So that’s the whole, you know, you can’t sell cars, the country, that roads thing. That was, again, a very interesting challenge for us is understanding. We were probably a year actually. And it was the woman who was the president of the industry association, who finally told me that Chartis was a job because I was getting frustrated about why we couldn’t get availability and pricing. She’s like, they don’t know, like their own sales reps, gotta go back to the office to do it.

Matt Watson 26:27
So you guys had to build a tool for them that you can basically give to them for free. So that then you can build the marketplace. So you can’t build the marketplace. What’s available, lets you have the data of what’s available, right? Like the huge challenge there.

Sam Mallikarjunan 26:39
Yeah, it’s OpenTable is a great metaphor, right? Like they had reservation management software for restaurants. And then once they had enough people using it, they could create a consumer-facing marketplace, right? Very much the same in our case, except, unlike them, we may not know your availability and pricing, but we know everybody who owns everything everywhere because of the permitting issue, and also scraping data from other sources like Google Maps. But yeah, to actually get the availability and pricing, that’s why we made that free software. So you can stop having to use a whiteboard, and you can use a free tool to run your business better, but it also makes it easier for people to buy from you.

Matt Watson 27:16
So I’m going to show that I’m gonna guess that’s probably a trick you learned from HubSpot. Maybe you created HubSpot giving away free tools. And it’s a great traction channel and a great go-to-market strategy. And actually, at my last company, stack phi, it was a huge part of our go-to-market strategy. We built a free tool. And I’ll be the first to say that, you know, one of the ways that we got that idea was actually from HubSpot, because, you know that one of the things they talked about from inbound marketing strategies was, you know, giving away free tools and lead generation, all that kind of stuff. And it worked really well. Really, really good for my last company was building a free tool to help, you know, get that network effect.

Sam Mallikarjunan 27:59
I did learn that HubSpot. That was my last major initiative before leaving, actually, was we how do we shift to freemium have, you know, these free tools that people can use that have paid upgrades here? If freemium had been a thing in 2006, the founder’s apps, I will tell you, definitely would have started out as freemium. But, you know, that wasn’t really how SAS companies worked back, then. It’s a great way to go, right, because, like, you have a free tool, you get to product market fit, then once people are like using your tool consistently, you start adding on more features, engineering is so much easier now than it was 15 years ago. It’s still hard. But like, you know, you can now have a Trello clone with five lines of code that you can, you know, build these free tools without having to spend a ton of money, and then start stacking on these kinds of premium features to create the monetization flywheel. So yeah, it’s I wish it had existed in the earlier days of HubSpot. But for people who are doing it now, it’s a great way to get initial traction to build on top of the funnel to create value and find out what people are actually going to use. And then that will give you the direction that you want to go in terms of building your premium features and your monetization.

Matt Watson 29:09
Yeah, and it can be a different tool. That’s also just a free tool that’s not necessarily directly, you know, a free version of your core product, right? It can be a separate tool. But so going back to your guys’ business and the integration, Jeff, to do so, you know, you know, one of the challenges you have, you know, trying to integrate with Lamar and all these people, right, as they probably also see you as a competitor, right. So, how do you get past the perception of some of the other industry players seeing you as a competitor, where you’re really trying to aggregate it all together, you’re actually trying to help them, you’re trying to integrate things together? But does that in some way scare them of exposing that, you know,

Sam Mallikarjunan 29:52
so the supply side doesn’t see us as a competitor? There is a fear in the industry that we’re going to replace sales reps. It’s A very common thing that I hear. I keep telling them we’re several Nobel Prizes away from Ai replacing sales reps in one at all, but especially in out-of-home or local knowledge and context matters. It’s almost like, again, the early days of HubSpot, the people who see us more as competitors, or people where business models are based on things that are kind of easy to automate. Like a lot of some of the buying agencies and things like that, you know, they see us as a threat, because it’s their, their business model to, you know, call 40 companies and buy billboards for you. Just like at HubSpot, agencies hated us in the early days, because they’re like, they used to charge for building websites. And we built a self-serve content management system, you’d go build a website on your own. And, you know, we had to educate those agencies on you on finding a new way, like, be creative, be strategic, like using retainers instead of working on project work. And now it’s like 40%, of HubSpot revenue or something like that. It’s the same in our in this industry, where there are people whose we’re going to make your lives better and easier, because you’re not going to have to do stupid manual tasks, copying and pasting between spreadsheets. And that may seem scary in the short term, but long term, it’s gonna let you build a bigger business that you actually enjoy doing more creative things.

Matt Watson 31:21
I would imagine that it for sure is going to automate a lot of things. And I inlay, you said I could see it affecting, you know, salespeople, especially those charting people are stuff that have to manually do a whole bunch of tracking of all that stuff, right? If you can kind of help the industry automate the availability of stuff and the scheduling of it. I mean, for sure, that eliminates some work that some people are doing manually today.

Sam Mallikarjunan 31:46
So it’ll make them much better like I will remain nameless, but a large national agency, there’s their CEO is telling me that they sometimes deliver what they know are subpar plans to brands, because they spend so much time doing things like getting lumbars spreadsheet back and then combining it with clear channels and then combining it with you know, everybody else’s into a spreadsheet. They don’t have enough time to do the planning, the strategy, and the analytics. So yes, it will replace some of the work people do. But I think it’ll do it in such a way that when they look back, people aren’t gonna be on it. Nobody misses their job as a switchboard operator.

Matt Watson 32:19
No. Well, this is the thing that happens across all types of jobs and all types of industries, right? It’s like people don’t pump gas anymore. Either. We pump our own gas like there. But that’s not really the greatest job in the world, either. Right? There are a lot of jobs like that, that have slowly faded away.

Sam Mallikarjunan 32:36
Yeah. And you get to do more fun stuff. Right? Like, yeah, it’s kind of the story of human history for the last couple of 100 years we went from doing boring manual repetitive tasks to being able to do things that actually use these big brains. We have an alternate reason, apparently. And it’s, it’s more satisfying and fulfilling. So yeah, it’s something I feel good about. But I also do understand why it’s scary. Because I, before the WYSIWYG CMS came out, I used to do that, like I would charge people money to make websites back in the early 2000s. And to have that go away, and like what you think is your business model, your competitive advantage is now gone. Because they invented WordPress or whatever. It’s this scary, it’s hard to change.

Matt Watson 33:19
So do you guys do anything to help with TV ads that seem like a logical component to this too?

Sam Mallikarjunan 33:27
I’m super interested in connected TV. And even like retargeting on social media and like this kind of integrated experience. Have you seen a billboard? Do you see a local TV commercial, you’ve maybe then seen it on Facebook, it actually feels less creepy to consumers, because it makes you feel more credible. Like, people see things in the real world, and they think it’s real. The problem with TV is it’s still generally bought like linear TV, you still have to buy an area, and you got to buy all of New York City to get to know one neighborhood. It’s a very similar challenge to how out of the home has been previously where, you know, buying the right billboard in the right place, or having the right taxi ad show up only in front of the business you’re trying to sell to is a new concept. So CTV has blown up for a reason. I think the biggest challenge is consumer adoption of CTV linear TV. I am not as bullish on it because it’s still relatively expensive, and it’s much harder to target. And even as I’ve expanded my mind as a performance marker in recovering performance marketer who’s now thinking about things other than click testing on AdWords, I still can’t bring myself to just buy TV commercials that are spray and pray for an entire geographic area and then hoping I catch the right people.

Matt Watson 34:47
Well, as a consumer, I hope for the day that we get more targeted TV ads, right? I mean, we all know we’re gonna watch TV ads. I’d rather watch a TV ad Tell me about some new thing that Tommy Bahama has and I can go buy some new thing or coupons or whatever than watch TV ads about Viagra or some dumb shit I don’t care about. Right. So I don’t mind the targeting advertising, if it’s more targeted to me, that’s been an interesting part of the privacy conversation is it’s not that people don’t like targeted ads they actually do.

Sam Mallikarjunan 35:11
In fact, when you do it well enough, it just feels like part of the content experience as part of what inbound marketing was back in the day. I think those were ads, they were just blog articles that would teach you something and you download an ebook or whatever right? Is it that people don’t just like that what they dislike is targeting that they feel well, in reality, is based on people abusing information about them that they have no control over? You would love to see that more targeted ad. You wouldn’t love to see an ad that is creepily right on point exactly something you’re super interested in. And you know that that means that somebody somewhere has a bunch of information about you that you did not give them permission to have.

Matt Watson 35:58
Yeah, absolutely. Well, so where do you know, as we start to wrap up this episode, where you see the future for things going at

Sam Mallikarjunan 36:10
I mean, the future for us is relatively clear, right? We’ve got the, to an extent it’s like I get to do all of the things we did back in the day, but I have role models. I got it helps. While we were inventing these things, freemium was a new thing that was invented, etcetera. offline media is kind of like the internet and the late 90s, or the early 2000s. But unlike Clay Christensen and Scott Brinker and the great thought leaders of platform strategy, I don’t have to invent disruptive innovation, I can just implement things that I know work elsewhere, like auctions, right? As we know, they drive up prices over time and maximize, you know, monetization doesn’t exist the in the offline media space, and things just go unsold. So that’s, that’s the good side of this, the bad side is, I’ve actually only time I’ve ever wished I had more competitors. If anybody wants to launch an out-of-home startup, please do. So it reduces the number of things we have to build, I will literally help you hit me up on Twitter or LinkedIn. And there’s plenty of money in it. But that’s, that’s the thing that we have to do is like, stay really focused. And, you know, do one total addressable market at a time, right, like not, not tackle events, not tackle brand marketers or people who are outside of kind of our core persona, it’s so easy to get distracted by really, really good ideas. So that’s we’re going to focus on that, especially performance marketers. They’re the ones who are dying. Right? Every thought truck drivers are gonna lose their jobs. Ai, turns out Facebook ads managers lost at first, because this point, do great foot Facebook ads, just tie into the Facebook ads API and let their AI figure out what, when, and where to show your ads. And there are people like me, and they’re fun, they care about data, they want to do something new, they’ve been stuck on the internet. And we literally bought the domain save Like how can we make marketing enjoyable professionally again?

Matt Watson 38:10
Well, I love what you guys are doing. And some of our competitors, my old company, used to do billboards around Silicon Valley and stuff for their products, even though it wasn’t b2c, it was a b2b product that, you know, 99% of people that drove by would know what it even was. But for that 1%, it was a way to reach them. It’s like, it’s like your point about Elon Musk. Like, if you want this niche audience you can still even do it with Billboard, so it’s cool.

Sam Mallikarjunan 38:36
I really want to get a LED truck, which is an option in the marketplace, and it has sound and just has the sales rep’s face on it, and park it in front of the business you’re trying to sell to and just be like, my name is Jim. I’m gonna call you next Tuesday at 3 pm. If that doesn’t work, here’s a short URL to my calendar to book a different time. At the very least, you’ll get the awareness, if not an actual inbound conversion. So it’s, again, this is fun. This is the most fun I’ve had during the marketing in a long time because it’s not just running your 9000 av test on Google AdWords.

Matt Watson 39:09
Well, once again, this episode of Startup Hustle was sponsored by our friends over at Equip-Bid Auctions. Join, sell and earn it’s that easy with equipment auctions, become an affiliate, and start to grow your independent business by visiting Even easier, head to Startup Hustle dot XYZ and check out our partner’s page. You’ll see equipped bids founder Andy has everything set up for you to go make some money to build your business within a business. Well, Sam, I really appreciate having you on the show today. As we run out of the show, do you have any kind of final advice for other entrepreneurs that are listening?

Sam Mallikarjunan 39:47
Humility, words of wisdom, humility going especially when going into new markets, right like the I think the attitude of we’re from the internet and we’re here to help or if you’re going into FinTech or prop tech or Some of these markets like we’re used to everything being interoperable on the internet, we’re used to, you know, a very different mentality. So like, really listen to your customers don’t think about just what you want to use and what you wish existed. And then also like don’t be afraid to competitors. If you people may not realize that Salesforce and HubSpot are competitors, they still integrate with each other. Because at the end of the day, whether you use the HubSpot CRM or Salesforce, you’re still more likely to be a successful user of the marketing tools if you’re using a CRM. And I think that was one of the big takeaways that I took from, you know, from that role at HubSpot, I’m trying to impress on the market here is if your only strategy is to, you know, not cooperate with your competitors, instead of focusing on creating customer value, you’re gonna lose eventually just question the time.

Matt Watson 40:51
All right. Well, that’s great advice. Again, this was Sam from And thank you so much for being on the show today. And congrats again for being one of the top startups from Boston. For those who are listening. You can check the show notes for links to all the other startups and maybe we should get a billboard just for you that says, you know, a top startup in Boston.

Sam Mallikarjunan 41:14
We might actually yeah, what’s your publish the episode we’ll get something, put it up on a digital billboard in Boston.

Matt Watson 41:20
And you get you can take a selfie with it. Absolutely. Well. Alright, thank you so much for being on the show.

Sam Mallikarjunan 41:28
Thanks for having me. And thanks again for the honor. All right.