An Agency Exit That Started With Free Work

All right. I'm here with Jordan, the founder of StratDev, who recently got acquired. Jordan, how you doing today?

Doing all right. How about you, Andrew?

Doing good. For those that may not know you, do you want to give a brief introduction of yourself?

Yeah, absolutely. So I am a builder at heart. I love to build things and I think I'm pretty okay at, uh, building from, sorry, zero to one. My bad. We're not going the wrong way, the right way. But with that, multiple time founder, countless failures, but couple successes. I've built, bootstrapped, scaled, and sold 3 businesses by the age of 27 years old, most recently being StratEv. And so with that, excited to chat with you a little bit more about that today.

Yeah, StratEv, that was a big exit. Tell me about the business. What did it do? What problem did it solve? Let's start there.

Yeah, absolutely. To put into simple terms, we turned a dollar into more than $1 for most of our clients, but that was at least the reason why they started working with us. So we were a digital marketing business at heart, uh, we worked with a lot of tech startup companies. So think of like anything coming out of like YC or Silicon Valley, recently funded, uh, companies that essentially promised their investors that they would get a good return on that investment. And, uh, as such, now need to go execute on some growth, uh, for that business. So they would come to us as a company and we would, uh, implement, uh, and manage and execute, uh, performance marketing, uh, campaigns for them. To help them again get, uh, $1 into more than $1. Uh, and so that went pretty well. Uh, I'd built that for 5 years. I started in college at UC Santa Barbara, uh, and grew it all the way to, uh, a relatively, uh, nice size company. By the time that we sold that company, we were ranked as the top 100 performance marketing company in the United States.

Damn, that's incredible. How'd you get into that? Were you a marketer before? Did you teach everything? Yourself? Like, how did you become such a good marketer?

Yeah. Yeah. Uh, YouTube is the short of that. Uh, I went to UC Santa Barbara, as I shared. Uh, I did not, if I'm being honest, learn anything, uh, as an economics major that was directly applicable to marketing, or if I'm being honest, being an entrepreneur as well. And so, um, actually, funny enough, my entrepreneurial journey started, uh, actually one of the first days that I was at UC Santa Barbara. I walked into my economics class, uh, super excited, you know, bushy-tailed. Ready to learn econ, right? And, you know, after 90 minutes of that class, I walked out actually pretty disappointed because it was quite theoretical in nature. It was not applicable or practical by any means. And so instead I went to my dorm room and thought, you know, what's hot, what's popping back in 2017? And back then dropshipping was super popular. And so I went to work and I built a Shopify store. That company was called Axiom Apparel. Put, I don't know, $500, which was the $500 in my bank account, into ads. Performed terribly, had to shut that down. But I, I still had that little bug. So I started something else and that failed, and I started something else and that failed. But after the 4th time, I started, uh, uh, a custom college apparel company called College Clout and grew that as a freshman all the way to my senior year, uh, to a, a, a really healthy, uh, uh, reasonable size. And so with that, I did all of that marketing by myself. I taught myself how to, uh, to write a blog post, how to generate any level of SEO traction, uh, how to, uh, get customers, how to get press, how to build partnerships, how to build an affiliate network, all these things. And so all of those kind of how-tos were actually search queries that I put into YouTube and watch other people in real time, uh, figure these things out and teach at the same time. I learned from those teachings and, uh, yeah, built, built a company, uh, from scratch and again bootstrapped, uh, through that as well. And so Um, all in all, uh, you know, when I ended up selling that company as a senior, I thought to myself, wow, I have this really amazing case study in the palm of my hands being my own company. I want to go do this and help other businesses grow and scale. Uh, and so that was pretty much the inception of StratDev. It started off as a one-person band being me, uh, helping other companies, uh, e-commerce companies specifically grow their businesses as I was able to grow mine.

Amazing. It's, it's incredible how much of entrepreneurship is just creating movement. Like, you started one business and you obviously have to learn how to do all this stuff. You got really good at the marketing, getting customers, getting users, and then you sell that business. That gives you an idea for another business. Um, that's incredible.

Exactly. It's a flywheel of entrepreneurship, right?

Yeah, no kidding. Well, tell me, how'd you get the first customers? Did you run like your own playbook? Did you fire up you know, some paid ad campaigns and target, you know, your ideal ICP? What did that look like?

Yeah.

Yeah.

Good question. So I broke the cardinal rule of business actually for this, being— I had this awesome case study in the palm of my hands, or so I thought. And so I went out to, you know, our first prospects. Probably, if I'm being honest with you, like door-to-door, uh, you know, in Santa Barbara, going business to business, seeing if anyone want to work with, uh, work with us. And so it was very difficult. Um, you know, I was, uh, 18 years old back at— or sorry, no, I was 20 years old back at that time, but I probably looked like I was 18, right? You can see, uh, for your viewers out here, I have a little bit of stubble. That's the most beard I can grow. Back then, I, I was clean-shaven. I looked very much like a little kid. And so they would hear this seemingly little kid come to them saying, hey, I can, you know, trust me with your money and I can turn it into more money for you. Look, I did this with my company, right? And they saw just like their son, right? Saying something to their parent, right? Where it's like, you know, it's cute, but it doesn't really hold that much weight. And so it was very difficult again to get clients because I was more or less written off. And so what I did instead is again, worked for free. And so I said, you know what, screw it. Uh, I need more case studies. I need more testimonials. And so what I did is I went to business owners and instead of saying, hey, pay me to go work for you, hey, I'll work for you for free as long as you do two things. One, write me a video testimonial, and two, we're allowed to use all your work as a case study. Um, and so with that, we worked with three different businesses. Uh, one of them was actually another entrepreneur at UC Santa Barbara, uh, named Christian. Uh, Christian, uh, I I believe we built a website for them and then we ran some advertisements for them. And Christian's father ended up being a, uh, pretty prominent, uh, CEO of a branding company, uh, based in the neighboring town. And so he saw the work that I was doing, uh, hit me up and he is like, hey, uh, you do actually some pretty good work. Uh, I would like to bring you on as a partner for this, uh, deal I'm trying to close. We need, uh, paid ads. Segment, we're a branding company, we can handle the website stuff, but we essentially need to bring traffic to that website. We don't have the capabilities in-house. Do you want to have a conversation about what that looks like? And so that individual's name is Randy. Randy gave me that first opportunity, ended up closing a pretty nice-sized deal as a first customer through that. So kind of, again, snowballed into something that turned into the start. And so You know, with that first customer, I was able to, you know, get our first employees and so on and so forth.

Nice. It's again, like just creating that momentum where you can't get customers initially because you got to build some credibility. So you go out and work for them for free and create the case studies. I think that's such a good strategy. Um, what made you decide to ultimately sell the business? Because you had a ton of happy paying customers, you had a repeatable engine for getting new customers. What ultimately made you decide to sell?

Yeah, yeah. It's a fantastic question. Ultimately, I was excited about building something else. And so, you know, that's something else now being materialized a couple, you know, months after acquisition was something that I had really wanted to get into for quite some time. I'd also looked at myself, you know, just genuinely, honestly, and introspectively in terms of what my own capabilities were in terms of running and growing the business. So, uh, in the 5 years of us, or me, uh, running the business, uh, I was able to grow the business, uh, about 118% year over year. So almost doubling that. And so, uh, doubling becomes much harder, you know, every consequent doubling, right? It's easy to do doubling in the first year, you know, that much harder the second, so on and so forth. And so, um, just looking at myself saying, hey, can I continue to for example, double this business, or does maybe someone else that, you know, has a little bit more experience, has, you know, the expertise to, you know, grow something into, you know, 8, 9, 10 figures, so on and so forth, be the better fit for running and also owning this business? And so it was a little bit of the blend of the two. And hey, I think it's the right time to hand this off to the next heir of StratDev. And then secondarily, you know, while I go do that, let me go start something else. Let me go build. As I share with you right in the beginning of this podcast, I love to build. I love that 0 to 1. That's what gets me really excited, charged up and amped up in the beginning of every single day. And so here I am building from 0 to 1 again.

Makes a ton of sense. I talk to so many entrepreneurs where like a lot of the value that they create is always in the 0 to 1 phase. It's what they love to do. They get the business off the ground, they find the initial customers, they get it to millions in revenue. And that's an ideal time to sell because you've created a lot of value there. And if you're able to sell a business, find a great buyer to take over what you built, and then start a new company and create that value again, I think it's super smart.

Totally. And so like, uh, you know, even playing off of that, one of my mentors had shared with me really early on, it's like, you know, there's one person that's going to take you from, you know, zero to, you know, $10 million, and the next one that's going to take you from 10 to 100. A different person is going to take you from,, you know, a hundred, so on and so forth. Right. But the hundred to a billion guy would do terrible going from zero to 10 million. Yeah.

Right.

And then, you know, so, you know, vice versa as well. And so, you know, with that said, it's just, again, different phases of the business, different, uh, you know, maturity, uh, uh, levels of the business require different operators, different owners in that business as well. And so to me, it's, you know, not a necessarily a good or bad thing. It's just kind of that natural path of progression. And so, again, I just saw my, end site coming too. So yeah, makes sense.

Different skill sets. Totally different skill sets and almost like personality types to execute a 0 to 1 phase and a 1 to 10 and 10 to 100, et cetera, et cetera. Tell me about the acquisition process. What were your expectations and how did it go?

Yeah, absolutely. So I It was in São Paulo, Brazil when I had decided, you know, this is what I want to do. I want to go and sell that business. And so, you know, as I'd shared with you before, this is my third exit. I had self-brokered the other two acquisitions and run that process, that sales process from A to Z. Not because I didn't want to work with a broker. If I'm being honest, I didn't know that I could bring in a broker. And so it was a little bit of, you know, rough learning by doing. But, um, you know, I, I had had that prior experience. Um, March of 2025, decided that I wanted to go sell the business and started prepping at that point in time. So let's get all of our books in line. Let's, you know, make sure that the team is solidified. Let's, you know, extend those customer contracts. Uh, make sure it looks really sexy, attractive, and appealing to, uh, you know, a prospective buyer. And so, uh, we got that ready over probably 2, 2 and a half months. I think we, uh, launched, uh, on a plethora of different sites, including acquire.com, uh, shout out acquire.com. Uh, I think in June of 2025, and I personally had the high hopes of, uh, getting to a point of acquisition around like September, October time. Uh, I think as a lot of really fast-growing and ultimately just attractive businesses see, you're going to get, or attempted to get courted a lot, especially in the early times. At least how I see it is before you sign an LOI, and for the listeners not knowing what an LOI is, a letter of intent, which essentially is when you sign exclusivity with a buyer. It's like being a hot girl at a bar, right? Everyone wants to go talk to you. Everyone wants to go, you know, say like, hey, your business is great, we're really interested in this, and start asking questions, right? Because, uh, as a seller, the, the ball is in your court, right? There's a lot of different buyers that are, uh, you know, trying to, to court you to sign that exclusivity for them to dive deeper into the business, um, and also not have to worry about other buyers, right? All these other buyers, when they're talking to you pre-LOI, know that there's other buyers and that they might have to go outbid this other buyer, right, to be that best offer for you to sign their LOI. And so Uh, we ran a really tight ship. Uh, we ran a really great sales process. Uh, as a result, I think we spoke to, um, 215 total buyers on and off.

Wow.

Um, we got 11 LOIs, uh, from a mix of, um, from a mix of, uh, uh, you know, private investment vehicle companies, from a mix of other, uh, bigger marketing firms, uh, PE companies that wanted to do roll-ups, uh, PE companies that wanted us to be the kind of you know, mitochondria of that cell and roll other companies into us. Um, the whole, whole nine yards and whole plethora, right? The whole shebang. And so, um, that was a very fun time. We got all of those LOIs in by the beginning of August. Uh, we signed into, uh, you know, the right one, and it was absolutely the right buyer from that point all the way onwards. Um, because of the size of the deal, there were, uh, you know, bank, uh, loans involved in that as well. And so, uh, you know, through those bank loans and institutional kind of investment vehicles, that was the thing that slowed us down. And so what turned into a hopeful September, August closure extended from October to November to December, all the way to January where we ended up closing January 30th. And I can tell you all the stories, Andrew, of the ways that we had to go navigate all of the hardships of that, but Uh, you know, it was definitely a difficult sale, not due to the buyer buying anything. The buyer was the reason why the deal ended up going through is because, uh, you know, that the, the buying entity as well as myself had such a strong relationship. And even through the other turmoil and hardships of just what happens once you sign an LOI and all those different things that could go wrong or things that, you know, you get blindsided with, you know, we were able to work together as a team to be able to overcome those. And so, a couple of dark times turning into more positive ones just due to that amazing relationship with that buyer. So if there's a lesson to be learned there, having a great buyer and choosing that truly right buyer is deeply important to make sure that you do transact at the end and you have a successful closure to that acquisition.

100%. How did you keep everything on track when things were going that long, or how did you maintain your sanity? With that long of a delay with the bank financing?

Those are two very different questions. In terms of keeping things on track, I think the same personality traits of me being a half-decent entrepreneur, right? It's tenacity. It's being bold with statements. It's, you know, hey, you know, get your shit together kind of things when stuff might not be together. And then, you know, in terms of sanity from being be totally honest, friends and family. There are times where I had reached out to mentors saying, you know, I don't know what to do. I'm losing nights of sleep over this. I'm freaking out. You know, there were times that, you know, as a man, I shed some tears, you know, over it as well. It is tough. And especially when you think that everything is going so perfectly, even, you know, in our situation where I felt like the, you know, crown prince getting 11 different offers. Oh man, this is going to be easy. A cakewalk, right?

Nope.

Something will come and bite you in the butt. But again, to get to a successful closure, you have to have that tenacity to turn around and, you know, fix that problem and move forward, right? Because there are again going to be problems that you need to fix. So yeah, having people around me to help walk me through this, tell me it's okay, help me see the light at the end of the tunnel. And even before that, right, just figure out how to stay composed through the entire process, especially when things got very difficult.

100%. It's so important to have just people you trust and admire in your corner through times like that. Yeah, that's amazing. And the deal's not over until the money hits your bank. There's so much truth in that statement. And you didn't do this, but I think one of the worst things you can do as an entrepreneur is celebrate when you sign an LOI or get super excited before the money, you know, clears your bank account because things can just happen. They're unexpected.

Yeah. You know, this is an Acquire.com podcast exclusive here. I haven't told anybody this outside of the people who ended up attending, but in September, when I thought we were, you know, days away from closing, I actually ended up renting this massive villa in Bali because I was in Bali at that time, inviting all my friends. I'm not even kidding you. There's probably like 300 people at this party., and all celebrating the fact that we were about to close. A couple days later, I received a couple of, you know, new pieces of information. Oh, we have to go push it 30 days for this reason or that reason, you know, so on and so forth. And so, um, yes, uh, I, I looking in retrospect, uh, probably should not have done that. It's really funny because, um, you know, all my friends that I invited when I actually posted that I had sold the company were like, Dude, I thought you sold this like 6 months ago. So it was, it was a little bit interesting to have to go explain that. Well, you know, so did I.

So yeah, you got it over the finish line. That's, that's all that matters. I have a similar story where we had a false start where we had closing date. It wasn't nearly as lengthy as yours, but flew like a lot of team members in. We were going to have this like Friday afternoon party. Didn't close. Everyone had to fly back. And then when we finally did close, like, no one was there to celebrate with me because everybody— we were like a half remote team. But again, it's just part of the process.

It's how it goes.

I'm curious about the buyer, though. What about them made you decide to sell the business to them? You mentioned that this buyer was exceptional. What made you get that vibe early enough to make the right pick? Because you're right, like, there's a lot of buyers where when these timelines happen, they could get skittish or no longer interested in the deal. But when you find a great buyer and they see the value in what you've built, they'll stick around through these delays understanding like, this is a good business, I want to see it through.

Most definitely. Most definitely. So again, I know I'm speaking from a point of privilege because most sellers don't have 11 LOIs sat on their desk and the flexibility and options that I had. And so You know, in my, uh, uh, reality, I, I did, right? And so I was able to be very selective and very picky and go back to a lot of these buyers saying, hey, these are my terms. If you don't accept, I'm off to the next, right?

Mm-hmm.

Uh, so with that, the buyer actually, um, did not have the most ideal terms if you're looking at it from a price point perspective. Um, I chose the buyer HSR Capital, uh, for, for 3 reasons. Um, the first one, uh, was based off of just the offer in itself. The offer was very thoughtful, very well thought out. It was definitely on the higher end of the offers that we got from a monetary perspective. And, you know, what I think that I, I would have, you know, made out in terms of total consideration, um, as well as structure. Uh, so there was that, right? And that was a, a playing part to it. I'm not gonna lie by any means. The other part is, you know, with StratDev and any digital marketing agency, at least before the Agentic AI era, you know, it was composed of people. And so I fully and truly honestly believe that the team came first. Culture was the most important thing to me. And I wanted to make sure that that legacy of good culture was gonna be able to transition over, and so I asked all the buyers, you know, very bluntly and honestly, like, what are your plans with this? Like, can you guarantee that everyone has a job 6 months into the future, 12 months in the future? Are you going to enable them? How are you going to enable and empower these people? Are you going to enable and empower these people? Are you going to switch anything up? How, when, why? All those questions. And so, you know, the managing partner at HSR Capital, who is now the president of StrathDev, Was very much a people person, a genuine individual who didn't just tell me the things that I want to hear, but I believed it. And especially going through those hardships, which were some people hardships as well, right? I was able to see him before we ended up actually closing in real time through his actions, reassure me of what I thought was the case before I signed that LOI. So it felt really good to go through those hardships together and see how he handled those. Those obstacles. But, uh, yeah, you know, to make someone to make sure it's someone to be a good leader and make sure that the team was well taken care of and that, you know, culture, uh, came first and I was handing the torch to somebody, uh, or an entity that would take good care of that team. So, uh, that was a very big, uh, box I want to check off. And then the last thing is also, uh, confidence in being able to get the deal done, right? Again, you were the hot girl at the bar. Everyone wants you. Same as, you know, guys going to a hot girl. They'll say anything to, you know, get that girl, right? And so it's kind of like having a little, you know, BS radar where you need to like really understand what they're saying, really have the confidence that when you sign into that deal, that it is going to transact. I had learned actually from my second acquisition that you gotta be just like, you gotta pull all the formalities and be bluntly, you know, transparent with that and say like, hey, you try any funny business, I have another LOI, I'll move over and I'll cancel this immediately. Then secondly, and I asked this verbatim, if, if there's anything that pops up, no, no. What did I say? I'm trying to think of it verbatim. I said something along the lines of, are we on the same page that you will move forward with this transaction? No matter what pops up, less of fraud, right? If you find fraud, I understand why you pull out, but if it's not fraud, are you going to transact? Do you have everything that you need? To be able to like very confidently move forward. Um, once we sign this LOI, if no, and you need more information, let me send it before we sign an LOI. Because again, that's exclusivity. You're locking yourself in. That's the only legally, uh, binding thing in that, that LOI agreement. Um, and so that was very important to me. And so I got that verbal confirmation. Yep. Like I am 100% into StratDev. Uh, we are going to make this happen one way or another. And sure enough, there were things that were like, seemed almost impossible to overcome, without getting into the specifics of that. And we were able to overcome them. But again, it's that tenacity, it's that deep want. I can promise you that, you know, if it wasn't that buyer, there's a very, very high likelihood that when certain things crumbled down, they would not want to rebuild, that they would not want Strathdev that bad, or realize that they didn't want Strathdev that bad. And so, you know, just honestly laying the odds and, and, and, prediction, probability, I guess, of like, are they going to close? And so they were quite high on that prediction.

That's amazing. I mean, I love how you just put so much time and effort into picking the winning buyer because it's super, super important. There's a difference between closing and not closing, and not all the time the highest price is the direction you should go. There's a lot of other qualities that you looked at, like, you know, looking after what's important to you, your legacy, uh, being on the same page post-acquisition. I think you handled all that perfectly.

Yeah, yeah. Well, thank you very much, Andrew. I, I appreciate that. But also, I, I don't think I would have, uh, handled that well at all if it was my first go-around with, uh, with this acquisition. Again, I had two other acquisitions prior that I had taken all these learning lessons from to be able to then apply to this third one. And I promise you that, you know, the first acquisition, I was screwed in every single way possible, uh, from that, that you can really imagine. And so, uh, again, you know, it's, it's, it's lived experiences to turn you into better in the next, next go-round.

Love it. If you were talking to another entrepreneur and they were looking to sell their business, what's like two pieces of advice you think you'd give them?

I think intention matters a lot. Uh, are you looking to exit because, uh, you are absolutely burnt out? Dead and dying? If so, you gotta find a little bit more fire. It feels like the end when you say, let me go exit, let me go acquire. It is the beginning of that end. And it requires you to actually be burning a lot hotter than probably the rest of your experiences. Maybe there's little spikes throughout that entrepreneurial journey of building that business, but I promise that last acquisition, you're going to have to turn on those burners. You cannot get complacent. You cannot get lazy by any means. So that's one. Another one is making sure that you have the right advisor or the right counsel to make sure that you don't find yourself in problems. You know, it's really easy to, you know, go the wrong direction or make a mistake, right? Throughout that entire process. Again, I have made a ton of mistakes. I even probably made some mistakes, you know, in this Shrative acquisition, but because I had that experience, I was able to avoid that. If I were to have made the same mistakes as I did on, for example, the first acquisition, I would've came out probably, you know, millions of dollars with a lesser outcome than I did with this one. And so, you know, the difference of just knowing what to do or having the right counsel or not is literally in some cases, you know, 7+ figures of a difference of, you know, what the outcome is for you as a founder. And so don't be afraid to ask, don't be afraid to have a good counsel, a good team, and one that, is aligned with you and wants the best for you.

100%. I mean, there's just so much that goes into getting a deal done. Having the right people in your corner can be everything.

Yeah, totally.

So what's next for you? You've successfully acquired. What's the next chapter look like?

A lot of Mai Tais on the south of Spain beach. That is what is for me. No, I'm kidding. Maybe half kidding. But Uh, I am, uh, one, truly and honestly taking it a little bit easy. Uh, I started my first company when I was 18 years old, freshly into college. I had built company one and then I built company two right before I sold company one, then three right before I sold company two. And so it's just been a consistent effort where I have really not had any time to just relax and breathe. You know, I'm 27 now, almost a decade of just hard work. And so now I want to just enjoy the fruits of my labor just a little bit. Uh, you know, and so, uh, we closed January 30th. It's currently, uh, June 23rd when we're recording this, this podcast here. It's been ish about 4 months or so, 5 months if my, uh, math serves me correctly. I, I've been traveling a lot. I've been enjoying life. I, I, I've, you know, worked on myself, my health, my relationships, uh, uh, with family, friends, girlfriends, uh, as well. And so that's been really, uh, rewarding in a lot of different ways, you know, The world is not just business, it's not just making money. Um, and so just again, being like a more well-rounded individual, uh, than just business. Um, the other side of things is, uh, you know, continue to be an entrepreneur. A builder is going to build. And so I started a venture studio called NextUp Ventures that is a really boring business that invests in cooler businesses as well as spins up new businesses. And so we have kind of two legs of that investment arm as well as, uh, kind of like an incubator that we're building businesses again ourselves internally inside. So that's really good. We have two businesses that we're spinning up currently right now, and then also made, you know, a small handful of investments over the past couple months too, deploying some of that acquisition money. Yeah, yeah, yeah.

Right on. Well, Jordan, I'm sure you're going to keep crushing it. I thoroughly enjoyed hearing your story and just learning about your journey. For people that may want to learn more about you or follow you online, where can they find you?

Yeah, totally. Go to jordancalderon.me, www.jordancalderon.me. That is my personal website. Probably should refresh it by the time that you are listening to this. It will be refreshed. You have my word. That has all my social media, that has all the cool news articles about me, that has Also my personal email as well as a place to grab some time with me if you want to chat about anything. I'm an open book. I love to talk to other entrepreneurs and help them in any way possible, give back where I can. So yeah, that's where you can find me.

Right on. Well, Jordan, congrats again on the acquisition and thanks again for coming on the podcast.

Thank you so much. Really appreciate it, Andrew. Cheers.