Behind the Success

Mike Pinkus: Over the last 10 years at ConnectCPA, we've had the privilege of witnessing the incredible journeys of over a thousand businesses. We've been there for the thrilling highs and daunting lows of entrepreneurship. We've celebrated wild successes and monumental exits, and we've also stood by businesses as they've navigated the stormy seas, facing roadblocks and challenges that every entrepreneur encounters in their day-to-day grind. Join us as we dive deep into the stories of these resilient individuals who dared to dream, who persevered, and who were a testament to the power of entrepreneurship. This is their journey, their lessons, and their triumphs. Welcome to GrowthTales. I'm your host, Mike Pinkus, co-founder of ConnectCPA.

Mike Pinkus: Today's guest is Josh Rosen, the president of Hotspex Media, a fast-growing media buying and planning agency in the digital advertising space. Prior to joining Hotspex, Josh also held the role of President at Wave Digital Media. If you're in the media and ad space, you've probably crossed paths with Josh at some point, as he's worked with some of the fastest-growing companies, helping them optimize their ad and media strategies.

In this episode, Josh discusses the importance of working with people you like and respect. Josh also shares some vulnerable stories from early in his career, when cash flow was tight and he and his partners had to go above and beyond to persevere through challenging times. Finally, Josh discusses the importance of being grateful and having a positive attitude, which he attributes to a lot of his business success and ability to push through those challenging times.

I really enjoyed the conversation with Josh, and I hope you enjoyed the episode.

Hey, Josh, thanks so much for joining me today.

Josh Rosen: It's a pleasure. We've known each other for a long time, so I'm really honored to, uh, to be doing this with you.

Mike Pinkus: Me too. And, uh, and I've seen your journey, Josh, over all these years, and you've done some really, really big things. And I've wanted to talk to you about your journey into entrepreneurship in media for a very, very long time. So, um, I'm excited to hear your viewpoint on a lot of the things that we probably haven't discussed yet.

Josh Rosen: I mean, weren't we one of your first customers also when you started ConnectCPA?

Mike Pinkus: Yeah, Wave Digital would be, uh, what year was that? 2014. Fourteen. So that's when we started, yeah. Yeah. Right at the very, very beginning.

Josh Rosen: So a lot of our success is thanks to you and the ConnectCPA team as well.

Mike Pinkus: Oh, I appreciate that, Josh. And you've always been an advocate, and we've always been big fans of everything you guys have done. And, um, and 2014 was a special year. You had joined Wave Digital Media. Why don't— I think the first question I'm gonna ask you, Josh, is how did you even get into media? You've done big things in media and at a bigger and bigger and bigger scale over the years, but, like, what made you want to get into media in the first place?

Josh Rosen: I'm probably the most reluctant entrepreneur founder of a tech company that you'll meet. Um, I didn't have it, you know, up on my vision board growing up as this is what I wanted to do. I wanted to be a fighter pilot or race car driver slash space cowboy. So none of those things materialized. So this felt like the second-best option for me.

I'm not a very good employee. I often would butt heads with senior leadership on my team. I worked hard, you know, I towed the line, but I always had a little bit of a chip on my shoulder and felt that I could do things better—differently. Different approaches, different tacts.

And the opportunity presented itself to me where I had the opportunity to join this upstart programmatic media company. At the time, when programmatic wasn't even a word, it was called RTB—real-time bidding was this method of how advertising was being bought on the internet.

And I came in as the oldest person, and I think I was that old—28 or 29.

Mike Pinkus: I was gonna say, like, you're not old now, so, yeah.

Josh Rosen: Yeah. So I was, yeah, turning 29 in the company. And, you know, to the credit of my current partner, Alexander Shore—or Ali—and some of the other guys that were there, they really gave me the opportunity to dive in and kind of lead them into where I thought we had permission to play in this space as this scrappy startup in the city of Toronto. And it's just been an amazing journey since then, since 2014.

Mike Pinkus: And that start that you had—your expertise, and I could be wrong in saying this—but you led sales, right? Like, you were the one who was thinking about how do you drive revenue? Right.

Josh Rosen: That's it. My whole background was sales. I came from a world where I was making, you know, 20 to 80 cold calls a day.

Mike Pinkus: Wow.

Josh Rosen: I was a prospecting machine. Everywhere I looked, all I saw was opportunities and businesses to call into. And I was never too shy or afraid to email or call somebody.

Mike Pinkus: That's incredible. And so you had the background in sales, and we're talking right now the early days—so, Wave Digital Media. You had two co-founders, and you guys scaled quite quickly. Were there any major challenges? That was your first take at entrepreneurship, right? And what would you say were some of the challenges? Like, it's very different from what you do now in terms of scale, but you guys were a small, scrappy team, yet you started to sign some big deals. What were those early days like at Wave Digital?

Josh Rosen: It was a rollercoaster. I mean, thankfully we've had the opportunity to have the benefit or perspective in being able to look back at them and take some really important lessons from it. And I think the number one lesson is: gracious in victory and humble in defeat. You want to really temper the ups and downs that come with starting a company, that come with those scrappy early days.

I don't care what industry you're in and at what scale it is—whether you're a hundred thousand dollars in revenue in your first year or a hundred million dollars—I feel like the lessons are always the same. We worked hard, we argued, we fought, but we always came together. And it was always from a place of trying to be better, of learning, of growing.

Josh Rosen: And it was really a journey of self-discovery for all of us that were involved. We really learned a lot about who we were as people, where our expertise lived. And, you know, I give a huge amount of credit to Ali. He jumped in and took over our trading practice with literally no experience whatsoever in campaign management for digital campaigns.

Him and the other co-founder had the foresight and the humility to say to one of our advisors at the time, "We think that Josh has earned his way in here and should have a greater equity play and should probably be the president of this company given his functions and what he's doing and how he's leading us here."

And I think that speaks volumes to their character traits. And that's why I said that journey of self-discovery was something very unique and that you don't really get in any other environment outside of co-founding and running your own startup. Right.

Mike Pinkus: And Josh, you mentioned you were very young yourself, but you said you were the maturity coming in—of being the eldest of the co-founders. But I think, like, knowing you personally as well, you've always been mature beyond your years. Meaning, like, ages aside, you probably brought a level of leadership, I think, that—as you had mentioned—that your co-founders noticed in you.

Once you guys started to pick up scale and you started to grow and start to have success, how did Hotspex come around? How did you end up where you are right now? And I'd like to hear that from your point of view.

Josh Rosen: So it's funny you call it leadership. Some call it arrogance. I guess it depends on which side you're on. And I think that that attitude that I have, that I'm trying to mature and work with, comes from this idea that—why not us, right? Like, somebody is gonna do this. Why can't it be us?

And you know, maybe that's an ignorance, maybe that's an overconfidence thing, I don't know. But it led us to conversations with people like Shane Skillen, the CEO of Hotspex, who I ironically interviewed with coming out of my college program to get an internship.

Mike Pinkus: Wow.

Josh Rosen: And he said no—that I wouldn't be happy here in the market research environment. And that started to put me on a path into the advertising agency world that I grew up in and honed my skills.

So you never know who you're gonna meet. And I brazenly added him as a friend on Facebook after that fateful meeting, and we kept in touch with each other over the years. I was always a big admirer of the work that he was doing and what the company was doing, and who they worked with and the technology that they developed.

And we were very serendipitous in that we had a mutual board advisor many years later who said, "Hey, there's an opportunity for Wave to partner with Hotspex on some digital media stuff that they're trying to do. You need to come meet with the CEO one day."

Josh Rosen: And I did. And we immediately were like, we know each other, we've spoken a few times—this is a crazy situation. And Shane had basically sold through a capability to a very large advertiser that he didn't have the solution for.

And I took on the project that he had sold through without having the solution for it, okay? And went back to Ali and was like, "Listen, we got a great opportunity—these guys at Hotspex—to work on this amazing project. You gotta figure out what to do here, 'cause I have no idea what to do, but we gotta seize the moment."

And Ali and Jonah Kate, who joined us at this point—who's now one of our VPs, one of our longest employees, and oversees a lot of our product development now—they rolled up their sleeves.

Josh Rosen: We put our heads together, and we came up with this idea that ended up winning gold in the YouTube Storytelling category at the CMAs that fall. And we were just like, "We are onto something here."

And again, that confidence, arrogance, whatever you wanna call it, I went up to Shane and I said, "Listen, there's something really special and unique that we could do as a unified organization here. We're stronger together. I think we should—I think we should get married."

And he was like, "I agree." And five months later—I think the fall of 2018—Wave was absorbed by Hotspex, and we became Hotspex Media.

Mike Pinkus: Wow. And how did they determine your title, whatever you came in as—President? Like, I guess you were President at Wave, and it just seemed like a fitting title as part of this transaction that was taking place, or this marriage between Wave Digital and Hotspex? Is that how it happened?

Josh Rosen: Yeah. Ali and I—we hit this point of relative success at Wave where we were like, "Okay, what's important to us as founders, as people, and where do we wanna take this business, and how do we get there?"

And we kind of concocted this Goldilocks scenario that we didn't think anybody would be able to come up with, that we would ever be able to find. And then this Hotspex opportunity came in, and it really checked all the boxes for us.

Was it perfect? No. But any solution, any situation is never gonna be 100% perfect. But it was—you know, I'll say—nine out of ten for us. And I mean, looking back at it, for me, it's one of the best decisions I've ever made in my entire life.

Mike Pinkus: It's funny looking back—it's hard to know when you make such big decisions. I mean, you guys are running a company, you're on your own, and I'm sure it's fun to some degree as well. It's a small group of people, and now you're moving to a bigger organization, and I believe bigger deals, probably more pressure.

How have things changed in terms of—like, you came from a sales background, you mentioned, with Wave Digital. How has the sales process changed now, moving to Hotspex? Have the deal sizes gotten larger? How do RFPs work? Has the process changed? Has a lot changed? And you’ve probably matured as well, obviously, as an entrepreneur/founder/leader. What does that look like today, now at Hotspex?

Josh Rosen: I think it depends on who you ask if I have matured. My wife and friends would probably say no. Ali would probably say no.

It changes proportionately and relative to everything that you shared, right? The team has grown because the amount of clients have grown, the amount of campaigns that we're working on have grown. Our principles, our values have evolved to be more all-encompassing, to be more in line with the stage of where we are.

I still look at us, and Ali still looks at us the same way. And I think this is where we’ve been able to maintain the success that we’ve had. I mean, when we were Wave Digital, our first four years saw us grow approximately 6,400% over a four-year period. Our three-year trailing growth has been over 1,500% as Hotspex Media.

Josh Rosen: We're putting down growth numbers that are unheard of. And I think it comes from this idea that Ali and I are both in lockstep on: that it could all evaporate tomorrow. We haven’t done anything yet. We are still, in our minds, that scrappy startup down on Davenport that is struggling for relevance.

And we don’t take any of our success for granted at all. I don’t. Every time we make a new hire, I feel that burden. I feel a tremendous amount of responsibility for the lives of the people that work here. And I am so grateful that they are coming along this journey with us, that they take the risk to join this company.

'Cause I'm like, how have you heard of us? I'm always surprised when someone's like, "Hey, I’ve been following you guys for a long time, and I heard good things when I was at this other agency. People were talking about you, your names are coming up through the hallways there." And when I saw this job posting come up, I had to apply.

I'm like, my mind is blown every single time that happens. And I really do not take that for granted, and take that on with a huge amount of responsibility for everybody. And that's what motivates me and drives me to show up every single day and send that email, or pick up the phone, or be away from my family to go to a conference where there's an opportunity to bring on a new client—or really just continue to build the brand that is Hotspex Media.

Mike Pinkus: You've mentioned the Davenport office, and I have really sharp memories of there being an open-concept office—you trying to get on a call and there's noise everywhere. I'm assuming things have changed now, now at—

Josh Rosen: Yeah. Yeah. We've solved the call situation.

My favorite memory—I'm not sure if you’ll remember this—and it involves you and ConnectCPA, was we were very close to—no free ad reads here, right? So—we were very close to a very popular, high-end grocery store in Yorkville. And we would frequent that place for coffees and muffins and croissants in the morning, and lunch in the afternoon.

And one year, we were going through our expenses with you in our office in that big open-concept area. And you’re like, “You guys are spending way too much money.”

Mike Pinkus: [laughs]

Josh Rosen: “This is insane. Who do you guys think you are?” That’s one of my most fond memories of that office and our time there.

Mike Pinkus: You know what—it’s funny because spending the money, it’s almost like self-fulfilling, where you start—you gotta act as if. And I think you guys always had that chip on your shoulder where you would act as if.

And it’s almost like sales, like you said. That growth—it almost happened like you knew it was going to happen. It’s almost like you guys manifested it. Like, yeah, we’re spending, we’re spending, but the revenue always went up to the right.

It’s actually shocking. In the early stages, watching how fast you guys grew—were you, even back then, were you guys expecting it? Did you think it would go and happen the way it did, and grow as fast as it did?

Josh Rosen: No. I often recall a situation where we had rent due for that office on Tuesday.

Mike Pinkus: Mm-hmm.

Josh Rosen: And on Friday, we didn't have enough money in our bank account to cover it.

Mike Pinkus: Right.

Josh Rosen: And we had pre-submitted the checks to our landlord. And we had no overdraft protection. There was nothing we could do outside of us putting in our own money to do it. And we didn't have that kind of money to spare—especially doing so without knowing when we were going to be able to get reimbursed for it.

And I remember going home that weekend and just being at one of the lowest points professionally I’ve ever been at. And obviously, that permeates through to you personally as well. You start to question your own self-worth and your own ability to do things. And I feel like this story is very important because you don’t hear a lot of founders talk about those lean early days. You only hear about the up and to the right—you don’t hear about the down and to the left.

Josh Rosen: And on Monday morning, we showed up to the office, because that was the only thing that we had to do—show up. Pick up the phone, send the email, and see if there’s somebody that would, you know, maybe prepay for something. I was preparing my speech to speak to the landlord and see if they could rip up that check or delay cashing it or something.

And I walk up to the office and see a little envelope hanging out of the mailbox outside the front door. I open it up, and there’s a check from our biggest client that would’ve covered, I think, two or three months’ rent at that point.

Mike Pinkus: How does it happen that way? It's—

Josh Rosen: You just—you just, you know, if you don’t believe, then you believe now. And I just remember having this feeling inside of me that was like, I never want to be at this point again. We can never be that close to the brink again.

And I think that if I had to look at a— you know, the TSN Turning Point of the company— I think that weekend, that was it.

Mike Pinkus: You are also a young father. I mean, you started early. And obviously, yeah, if you ask anybody, having a kid definitely changes everything.

And so in those days—like, I don’t remember the exact year that your eldest daughter was born—but it happened somewhere in the... I don’t know how old you were when all this kind of went down with your eldest, where you first had your first kid. But it matures you. And you were with co-founders that were a lot younger than you, where now it’s not only for you anymore. Like, you're starting to build a family as you're going through this.

Was that where part of the emotion came from, where you’re like, “I’m building a family now. This isn’t just for me—it’s for my entire family. I’ve got to figure this thing out”?

Josh Rosen: Yeah. Like I said, I spent a lot of time in a sales organization making a lot of money for a company and getting paid not a lot of money for my efforts. And when the opportunity to join the Wave team in its infancy was brought to my attention, I remember having the conversation with my very pregnant wife—who was expecting our second child—and being like, “We’ve always envisioned a life for ourselves that we want to have. This is how we’re gonna get to it.”

And it's a now-or-never situation because, you know, once those kids are older, it becomes increasingly more difficult. The stakes are higher now. It's risky, but it's relatively less risky. And she was like, “You gotta do it. You’ll kick yourself every day if you don’t do it now.”

Josh Rosen: So, with her blessing, I really went in and accepted the offer. And again, to Ali and the other guys involved—to their credit—I, you know, opened up my bank statement one day and was like, “Okay, this is what I got. We need to—if we can cover this, then we’re good. And we can focus on it. And I can be as 100% committed to this business as I need to be, knowing that my family is taken care of.”

And now, I feel like the grandfather of the group because my kids are the oldest out of anybody who’s having kids.

Mike Pinkus: That’s where I brought it up.

Josh Rosen: People are buying their first houses, right? So there's a huge amount of life experience that's come between us—of watching the team evolve and grow and do that.

And yeah, you'd be lying to yourself if, as this thing continues to scale and go in the directions it’s going, you’re not always looking at it from the perspective of, “Look at the amazing legacy that we’re building for our families.”

I don’t think any of us have any illusions of this being a family business that one day our children are going to inherit and take over. You never know. You never know.

Mike Pinkus: Those are rare these days. But yeah, it's—

Josh Rosen: Rare. But I think at the end of the day—speaking for myself—I want to do things that my kids are exceptionally proud of, and that when they talk about their father, they talk about me with a tremendous amount of pride, and can point to something that I built.

Josh Rosen: Yeah, I think it goes back to what we said before—everything is just bigger, right? You look at an F1 race team as an example: just because you won last year doesn’t mean you’re going to win next year.

So it’s wind tunnel testing, it’s part production, it’s driver training—it’s a whole bunch of different but similar tactics to get to the same goal. And you’re kind of always moving the goalpost as you go.

And I think that’s inherently what makes us successful—because we’ve had this taste of success, and I really kind of don’t like using that term. Because that insinuates to me that we’re done, that we’ve accomplished something definitive. And to say that we’re successful is to say that we’re finished.

And I think we’re just getting started. I think the industry, the market—it’s changing. You look at where AI has come from in the last three years. The products that we’re building, to your point, the type of advertiser that we’re exposed to now is giving us more and more opportunities to really flex some dynamic muscles that we didn’t have five years ago.

And it’s a really unique opportunity, and that’s what keeps me jazzed to come in every day and keep working at this. No two days are the same. There are new solutions, new opportunities that are far beyond where we started 10 years ago.

Mike Pinkus: I have one final question for you, Josh, because I want to be respectful of your time.

Josh Rosen: Sure, sure.

Mike Pinkus: And this final question is something I ask most people, which is: If you could look back at your younger self in those early Wave Digital days—or if you were to give advice to, let’s say, a new entrepreneur who’s just starting out, or they’re in their first few years going through those things that you mentioned, like rent coming due, and it’s not all rosy and co-founders can get into battles, and there are so many levels of adversity—what are some tips or shortcuts that you could give as guidance to people that are going through that right now?

Josh Rosen: That's a good question. I think starting a business—if you are going to have a partner—treat your business partner the same way that you would treat the process of finding your significant other, your partner in life. You end up spending more time with them anyway than you do your actual partner.

And you really want somebody that’s going to lift you up when you are down, that’s going to really, you know, fill the gaps that you have, that is going to challenge you and push you every single day. That’s how you're going to, you know—steel sharpens steel.

Josh Rosen: I think that’s something that is often overlooked. I think there’s a lot of people that go into business with their best friends or their cousin or even their spouse, thinking that, like, “Oh, it’ll just be fun.” It can be, but what about when it’s not, right?

And, you know, we don’t have the answers to everything. How do you find those answers? How do you—

I have strengths, Ali has strengths, and I think we really complement each other really well and offset each other and mitigate the weaknesses within each other so that we do present this very well-rounded leadership team to the company.

And that’s where we’ve ultimately been able to be successful—because we have this very strong relationship that’s based on mutual respect, and the dynamic elements that we both bring to the equation as far as handling the adversity and the challenges.

Josh Rosen: One of the mantras that we have with our now partner, Shane, that I say to him all the time is: “Best job I’ve ever had.” No matter what we’re doing. And the most recent example of that is—we had a really great meeting in New York, and there was some really bad traffic, and we were scrambling. We were literally sprinting through LaGuardia to get onto the plane.

We got onto our flight, we sat down and looked at each other, fist bumped, and we’re like, “Best job I ever had.” And we repeated it back to each other.

And, you know, we’re so lucky, we’re so grateful that we get to touch and shape so many people’s lives. That we get to have the autonomy and the ability to really shape our own destiny.

Try and focus on—and look at things through—the lens of positivity. Don’t get bogged down by the challenges or the adversity. Be open-minded. Learn from your mistakes. Challenge yourself. And remind yourself on the regular who you are, and that you belong.

And keep going. Just keep doing what you're doing.

Mike Pinkus: That's great advice. That's really great advice. And I love the way you speak, obviously, about your co-founder. You speak of him like he is your partner—you know what I mean?

And yeah, when you’re with someone for that long, I guess it becomes that tight bond of like—you’ve gone through so much together. And I would say, Josh, you’ve always been a relationship guy.

I have a ton of respect for the things you do. And I've always said to people: you are a connector. And so it's by no... like, you can see it’s not luck that you’ve gotten to where you’ve gotten to. You connect people to other people. And I think that is contagious, and people see that.

And I know personally, like at ConnectCPA, I felt it—in the sense that you always connect people, you’re always the one who’s active on LinkedIn and relationships.

And so, at least for me—because I know you personally—it’s not surprising that you’ve spent a lot of time talking about Ali in this conversation. And it does show your character. That it does take a team to get where you need to go.

And you’ve done it really, really well. And I have a lot of admiration for how you’ve done this, Josh, up until now.

Josh Rosen: I appreciate that. Thank you so much, Mike. Thank you.

Mike Pinkus: And thanks for taking the time. I appreciate it.

Josh Rosen: Anytime. Can't wait for, uh, round two of this.

Mike Pinkus: Yeah, we should do that. All right. Thanks, Josh.

Josh Rosen: Thanks, Mike. It is a pleasure. We've known each other for a long time, so I'm really honored to, uh, to be doing this with you. I mean, were we one of your first customers also when you started ConnectCPA—'14?

Mike Pinkus: Yeah.

Josh Rosen: So a lot of our success is thanks to you and the ConnectCPA team as well.