Episode 7: 2am Entrepreneur: Joe’s Story
Host: Joe Zappa
Length: 32 minutes
Published: August 24, 2026
Joe shares his entrepreneurial journey in the hopes that other entrepreneurs might do the same for a new series on this podcast. Listen to find out how annoying Joe was as a second grader. And reach out at joe@sharppenmedia.com.
Listen: Spotify | Apple Podcasts | YouTube
Full Transcript
Joe Welcome to the AdTech Marketing Podcast, the only podcast exclusively devoted to adtech marketing. I'm going to do something very different today. I want to tell you guys a bit about my entrepreneurial story because this is the podcast I essentially want to hear from other entrepreneurs and other business people.
And I don't hear it often. I think that really getting into someone's story as an entrepreneur is about understanding sort of how they grew up, why they became the way they became, probably some sort of inciting incident or disconnect they experienced as kids that drove them to want to achieve something big and sort of take on risk and take on the responsibility of running a team and, you know, providing for people.
And it's a big endeavor. And like entrepreneurs are like the people who wake up at 2 a.m. and they're like, "Shit, like I need to do better. Like I need to do better for my clients. I need to do better in terms of generating new clients.
I need to like better support my team. I need to raise them to a higher standard." You know, we worry about how much money is in the bank. Like this is, you know, this is the real stuff. Entrepreneurs are not paper pushers.
They're not like just clocking in for the 9-to-5. They are the people who sort of bear the weight of trying to achieve something and bringing people together to meet a higher standard. So I've often thought I would really want to hear a podcast that's like the 2 a.m. Entrepreneur Podcast. That's like a title I could imagine for it.
But I don't know, I don't think it's quite out there. There are great podcasts out there, like there's Acquired, which is the story of companies where they'll touch on this kind of thing.
There are autobiographies, and there's like David Senra, who's like created an amazing business by talking about the autobiographies and biographies of great entrepreneurs. But I think it's really rare that you get to sort of sit an entrepreneur down, or he or she sits themselves down, and you get to hear about how they got the way they are and why they started their business.
So I'm putting this out into the world because this is the pod I kind of would like to hear. And so I hope, you know, for the 17 people who are going to listen to this, I hope some of you will hear this and say, "Oh, I would do that.
I would be willing to go on a podcast like that." And maybe you'll come on and we'll get to have this conversation. I'll get to interview you about your experience. Because I assure you, if this resonates with you, there are a lot of other people who have gone through something similar who would maybe want to hear your version.
So when I think about starting out as an entrepreneur, the origins of my starting a company, I think about how competitive I was as a kid, and how intense I was, and how ambitious I was. So when I was seven—this is one of my earliest memories of feeling that way—
We played this game in my second-grade class in public school in Long Island called Math Around the World. And so it was a multiplication times table game. And you would stand up, and you would be next to another student.
And the teacher would say, you know, "Seven times six." And whoever said 42 first would move to the next desk. And you would move around all the desks that were arranged in sort of a circle. Eventually, if you kept saying the number first correctly, you would advance desks and you would make your way around the classroom or around the world.
And I just remember feeling like so deadly serious about this game. You know, like I was like, "I have to win. I have to push myself to learn this better than anyone else. I need the answers to be instantaneous."
And it felt existential to me. And I remember specifically one time the teacher, you know, I was standing sort of next to this other student and I was sort of standing at an angle in this like little fighter stance.
And you have to picture me being seven doing this. And I remember she like kind of pointed it out, and it was like embarrassing. And I think that's sort of an origin story because I think like people who are super intense, you know, about work or achievement, they're constantly going against the grain.
They're constantly struggling against like a world and a society that's like, "Chill out." And I think like for me, it's like from—since the time I was seven, I'm like, "No, I'm not going to chill out.
You don't understand how much this matters to me and how much I want to be better and achieve my potential." And then, you know, later down the road, help the people around me do the same so that we can all pursue this collective goal.
But I don't know why exactly I felt that way. I just remember that I did, you know, and my parents weren't like—like, I didn't have a tiger mom. My parents weren't—they weren't like walking around being like, "You need to achieve greatness," or like some shit like that.
You know, my mom didn't work for my first seven or eight years. And then she was, you know, she was raising my sisters and me. And then she went to go work as a paralegal for my cousin who owned a small law firm.
My, you know, dad was an accountant, and he had grown up working class and had sort of made it to the middle class or even the upper middle class. And I would grow up watching him. He would be gone before I woke up.
And he would often get home when it was like 8 or 9 p.m. So I definitely grew up watching him and being like, "Oh, he like achieved something great relative to what his dad, you know, my grandpa did."
And I want to do the same. I want to achieve something, you know, greater than—greater than what he did. And I think, you know, again, my parents, they never pushed me on that. They never like told me I had to do that.
But I do think from a young age, I kind of got the sense like, "This is what it's about," you know, like, "This is what life is about." And I think I grew up with that sort of existential concern that some kids have where like they're freaking weirdos, like they're like six years old and they're like, "What's the purpose of life?"
But like I was one of those kids, just like weirdly introspective. And so I think that pursuit of something greater, the pursuit of achievement and excellence at school, that gave me like a sense of a place in the world and purpose.
I was like, "Okay, I understand, you know, what I'm supposed to do and who I want to be." And so, you know, that continued through elementary school. I can think of examples from like every year from second grade on in elementary school where it was like I had some sort of interaction with the rest of the class or with teachers where people were just like, "Jesus Christ, chill out, bro."
But again, I possessed absolutely zero chill, which as you would imagine, really endeared me to my classmates. You know, I remember in fourth grade, we were at the times tables again, and we would have this thing where it would be like—I don't know how long they gave us.
It was like 60 seconds or a few minutes or whatever, but they would give us like a sheet where we had 100 times table questions. So again, I was like, "Okay, gotta win at this." And there would be like grade-wide, you know, like 100 kids in the grade.
And there would be these competitions where it was like, how many could you do? And I would like get through all of them. And then I would be like, "Bring me a second sheet." And then I would like keep going and I would win.
And I would be, you know, just extremely exhilarated by that. And this was like the thing I liked most, you know, in the world was like competing at this and getting better and having like a measurable goal I could attain.
So, you know, I also remember like the early downsides of that. Like I remember being in fifth grade and for whatever reason, like—what like the teacher or like I just wasn't as good that year or something, like I wasn't doing quite as well.
Like I was a huge effing nerd, right? But it was like—so I would get like one A-plus and like four A's instead of all A-pluses on my report card. And I remember like when, you know, I got into sixth grade and I would get like perfect grades again, I would be like—I remember feeling like I like, "I'm back, like I have my identity again," you know? Like I felt like anything less than perfection, like the highest possible standard,
I had like lost who I was, and I had like lost my place in the world. So I was just like a crazy like nerd kid. That was just like the standard that I wanted to hold myself to, which I know some people are probably like, "That's like mentally ill."
But, you know, I was obsessive and I still am. And like the happiest moments of my life have been those where I've had something I'm obsessive about. And I've had other people around me who get that and who are obsessive, too.
And, you know, we're just—we're going for the greatest thing that we can achieve with it all being relative. Time went on. I had times when I was like in ninth grade. I was like, "This is my rebellious year."
You know, "I'm sick of trying to achieve like this and being the perfect student," or whatever. And I would like not do homework and mouth off to my teachers. And I got like in-school suspension for a few days once because I was like butting heads with this one teacher.
And when I was in 10th grade, it was like the first week of school, and I was on the bus, and there were just kids being like, you know, Neanderthals around me, as kids will want to do. And I was like, "I don't want to be in this environment forever."
I was like, "I know I have greater potential. I don't know what that last year was about where I was like acting out, but I'm going to get on the right track now and like, I'm going to apply myself and like, we're going to get back to it and see what we can achieve."
And the next three years, 10th through 12th grade, I just like hustled like a mother effer, like, you know, doing all the usual like class stuff. But I don't know, if you weren't a huge freaking nerd as a kid, like you might just not know what like nerds are like, right?
Like, you know, I took nine periods of classes, and like I had no lunch. You know, I would like eat my lunch in like Chinese class or whatever, which is like the, you know, 15-year-old version of having like back-to-back meetings for like eight hours.
Right. And then after that, I would like go do my extracurriculars, which I was like, you know, president of three or four clubs and like captain of the tennis team and all that shit. And I wasn't captain of the tennis team, by the way, because I was athletic.
Don't think that for a second. Tennis was like the sport that the nerds played. And I wasn't even the best one on the tennis team, but you know, they made me captain because I was like super responsible.
So I hustled through high school, and, you know, the carrot at the end of K through 12 is going to a fancy school. And that was my goal for most of my childhood. My parents went to local private schools in Long Island.
I didn't know anyone who had gone to an Ivy League school. I didn't know any adults who had done that. But, you know, when I was like 14, 15, I remember my mom was driving me to a tennis practice and we were talking about college and she was like, "You're going to have a shot at that, of going to an Ivy League school."
And I just thought that would be, you know, the most like incredible thing that I could accomplish and that could happen to me. And when I was, you know, 17, I applied to Brown and I got in. I remember it was December 12th, 2012.
And it was truly the happiest moment of my life to that point. I opened the email, and my mom and my younger sister were standing behind me. And, you know, we all just like fell in a like puddle when I got the news because it was like 12 years of work that culminated in that moment.
And I knew, you know, in that moment, I was like, "I just got like a ticket, right? Like, I got a ticket to achieve my dreams." And it's funny because like nowadays, like now that I went through that system of like—I went to Brown for undergrad and I did a PhD after at Cornell.
I'm like, I think, you know, elite education is like messed up in all of these ways. It is like a conformity machine. You're allowed to believe some things and not others. I think there are a lot of shortcomings to it, but it is also an incredible driver of class mobility for the few people who are lucky enough to get there who—or work hard enough—who are not already from, you know, the upper crust of society.
And like, let me be clear, I understand, like, I started on third base, right? Like, I was, you know, my parents did pretty well. We grew up a very middle-class, like suburban, typical upbringing. But still, for my family, which, you know, we were an immigrant family, came over from Italy, you know, a century ago.
For my grandparents, you know, none of the four of them finished college or went to college. Then my parents went to the local college and sort of achieved this like middle-class dream. And then for me to be able to go to—to, you know, have that goal my entire childhood and then go to a fancy school, it was like, "All right, I did what I was supposed to do when I was watching my dad, you know, get up at 5 a.m.and then get home at 9 p.m." Or I, you know, I did what I was supposed to do as a kid. And now I was just getting the chance to start an adult life and start a career pursuing something greater than what I had grown up around.
You know, went to college, went to grad school. You know, I did a PhD in literature, which to most of the people who listen to this pod is probably like some random weird thing. I basically like—there were a couple of things there.
One is my whole life I'd been doing school, right? So that's what I knew how to do. And when I looked at like the business world when I was in college, I was just like, "I don't know anything about that."
Like it was totally foreign to me. If I had a kid and they were going to college, I would be like, "Yeah, you could do the PhD thing or you could do business. And here's what business involves, right?
There's management consulting, there's finance, there's marketing, there's all these different things, tech." And I would sort of help them understand what the options are. But I didn't really have that.
And I just didn't seek it out because I wasn't inclined that way when I was in college. So between my aptitudes being sort of intellectual and in the humanities as a college student, and then also the other reason I ended up pursuing the PhD was I was like, "I just had these burning questions about some like fundamental truths about the universe."
You know, there was that like sort of like nerd part of my personality that wanted to know like, "What is the purpose of all this? What is the truth?" All these sorts of things, these sort of age-old philosophical questions.
And then also I had arrived at the end of college and it was the first time in my life, in my senior year of college, where I started to doubt the achievement-oriented track I had been on since, you know, Math Around the World when I was seven.
I had, you know, gotten perfect grades in college. I was like—I had like an honors thesis. I was Phi Beta Kappa. I was the managing editor of the college paper. I did all that shit. Like I kept doing the sort of like cookie-cutter achievement-oriented nerd thing.
And I got to a point where I was like, "I don't know what this is supposed to bring me." I did everything I thought I was supposed to and that I wanted to achieve up until this point of being like a 21-year-old college senior.
And I wasn't that happy. And I wasn't wise enough yet to understand like where, for me, happiness comes from. And so I was like, "Okay, maybe I just got to go like read a bunch of dense philosophical texts and novels for another like four years and I'll figure that out."
And so I went to do that, but the whole time I was in college, I was kind of working multiple jobs. I was like the editor of the student newspaper, which for people who know how The Brown Daily Herald works, it's like a super intense thing where it's like you're actually running like a small daily newspaper.
So they were like, we put out a print version and online version every day. And there would be like eight to 10 stories. So that was like a full-time job of running that little organization, which is, I guess, now that I think about it, one of the first like significant entrepreneurial efforts I undertook.
So I was doing that. I had started freelancing as a journalist. And that's actually when I started to get into Martech was I was freelancing for a Martech media site called Street Fight. And I was, you know, writing an honors thesis and applying to grad school and taking a course load.
So I kind of had these multiple irons in the fire, and I was always working hard at different things. And when I went to grad school, I continued doing Street Fight, which was a Martech media site founded by David Hirschman and Laura Rich focused on the location intelligence industry and multi-location marketing.
And so that was my entry into Martech, and I kept doing that all through grad school. So I was pursuing my doctorate and writing my doctoral thesis. I was still freelancing as a trade journalist. And then on top of that, David eventually handed me the keys to that publication—like made me the editor.
And he also referred me some other business. So I started building up a little freelance portfolio. You know, one of the things I'm proudest of from like the early days of my entrepreneurial journey when I was a freelancer, you know, sort of in that period many freelancers go through before they evolve from freelancer to like micro-agency owner or entrepreneur, is I had a lot of times where, I think the average—I think it's fair to say the average person would have been like, "I'm good. Like I'm doing enough, you know, I don't need to do any more," or "I got to stop doing this one thing because I am too busy."
I was always a, you know, a glutton for work. Like I, in college, you know, there was a time where I would get up at 6 a.m. every day to do the Street Fight newsletter, but I was also working at the paper and the newspaper would happen after everyone sort of finished classes for the most part.
So production for the newspaper would run from like 5 p.m. to like midnight or sometimes 1 a.m. And then I would like get up at 6 a.m. to do the Street Fight newsletter. And then as I said, I was also like writing the thesis and doing college coursework and whatever.
And I remember I said to David Hirschman, like senior year fall is coming up, "I don't know if I can keep doing this. Like I'm going to have the paper, the nights at the paper, and then I'm going to have to get up in the morning and do this."
And I was kind of like, "Could you like hold it for me?" And he was like, "No, I can't hold it for you." You know, and he was a super nice guy and had given me this great opportunity. I think he was paying me like $1,200 a month at the time, which to a college kid is like a lot of money.
And I was just like, "Okay, you know, if you can't hold it for me, if I've got to keep doing it to do it beyond the semester where I'm going to finish up being the managing editor of the newspaper, then I'm just going to keep going."
So I think like what anyone listening to this with whom this resonates will recognize is like, if you're an entrepreneur, you just had a hundred cases like that where you just said, like—you just said yes, you know, like, we're yes people.
We're overburdened. We can't do anymore. We don't know if we know how to do it. And every time like the next opportunity comes that could build—build our resume or strengthen the business or expand the services, we say, "Hell yes, I want to do it and I'm going to figure it out," you know, and "I'll figure it out whether that means it's something I don't know how to do yet, or I got to find someone who knows how to do it, or I'm going to have to work 18 hours a day for a limited period of time to get through this period, and then I'm going to come out on the other end stronger."
So I'm proud of that, that, you know, I was able to keep doing that through college and grad school. And as grad school was going on, eventually the early beginnings of Sharp Pen started to materialize where I was editing Street Fight, and then I got like a couple other freelance writing gigs.
I got my first content marketing gig helping out a proptech company with their blog, you know, back in the days when SEO was king. And I discovered marketing and I was sort of ending—nearing the end of my PhD.
I'd realized I didn't want to go into, you know, university life full-time, both because the academic job market was horrible and because I had kind of realized it was like this stagnant thing, and that I'm lit up by dynamism and opportunity.
You know, and I kind of got to the point where I was like, even if I reached the pinnacle of being an academic, you know, being a Yale professor of literature or something, I was like, "Eh, they do the same thing every year," you know, and there isn't—I kind of know what that looks like.
And then I had gotten these marketing gigs and I was like, "I don't know where this ends if I go down the sort of like marketing agency, marketing entrepreneur route." You know, I got to the point when I was a grad student where I was like making a hundred grand as a freelancer—a hundred grand a year.
And that was when I was like, "A, I can actually build a career and a life and a, you know, a living for myself doing this. And B, I feel like I'm at the very early stages of this. You know, I've got a few clients and I'm making a hundred grand a year."
Like who knows how much I could achieve? And I thought like maybe, you know, five years from now, I'll like start an actual business. But, you know, I started freelancing for some agencies and I was hustling.
And anytime, again, anytime someone wanted to offer me work, I was like, "Yes, please, ma'am or sir. I want to do this. Give it to me. I'll hop on a call in two hours. I'll turn around the content in a day."
And I knew from the agencies that started giving me work that when they would work with other freelancers, the freelancers would constantly be like, "Oh, I don't have the bandwidth for this," or "I'm busy," or whatever.
Or they would say yes and they would take a really long time. And I was like, "I will always say yes. I will turn it around as fast as I can. I'm going to do it to the best of my ability." And in the beginning of Sharp Pen, like just doing that got me to like 50, 60 grand a month in work because, you know, there were agencies that, let's say they were paying three or four freelancers before to do their content, you know, they would pay just me because I would hustle and I always said yes. And if you have ever tried to look for freelancers, you know that someone who will always say yes, who always has bandwidth, works fast, and does good work is a very, you know, hard combination to combine.
So again, there's that attitude of just like, "I'm going to pursue something where I have a really high ceiling. I'm going to like work my hardest. And I'm always going to say yes when an opportunity presents itself."
And through doing that, you know, I was able to move past the journalism phase of my career to becoming a full-time marketing freelancer. And then when I hit around 50, 60 grand a month in work, you know, I had a lot of work from agencies and a couple of my own clients.
I was like, "I have enough to hire other people." And that's when, you know, it really transformed from, "I'm a writer," to "I'm a freelancer," to "I'm a marketing consultant," to then like, "I am an entrepreneur and I have, you know, a small business, a little agency on my hands."
And now we're five years in and now this shit is changing again. And that's sort of why I thought to do this today is because I'm realizing that now we have roughly 20 clients. I have a full-time team of eight.
Four of those people are like—they have families to support. And like I've realized like in the last few months, I'm like, the bar just like rose again. It's one thing to get an agency to like 10, 12 clients where you're still really a consultant.
Maybe you have a couple helpers or whatever. It is a very different thing to be like, "I'm going to operate an actual business with like a full-time staff and, you know, salaries and benefits and all that—like having real overhead, having real responsibility to people, but also having a responsibility to clients, right?"
Realizing that if you have 10 clients and you're on all of them, there's a different level of vigilance required when you have 20. And it's like you can't physically see all of them. So then what is your responsibility to the team and to your clients, right?
The responsibility becomes you need to become vigilant as a mother effer because you're not going to straight-up see everything. So you've got to, you know, use all the tools at your disposal, which thankfully nowadays we have amazing tools.
You know, you need to get the data from what's going on in those conversations. You need to use AI to monitor it proactively. You need to ferret out issues. You need to show the team constantly how to do the work better, set up systems to execute.
You need to see when those systems are failing or not being upheld properly, proactively identify issues, and get in there with every single team member on every account and help them achieve the best that they can so you can achieve more as an organization.
You know, I just feel very deeply, this is the latest stage of what I've been working on since I was seven, pushing myself to be better, but it's different now because it's not all about me, right? It's not just me pushing myself, you know, becoming an entrepreneur, a real entrepreneur and not just like a freelancer is about taking that same mentality of "I need to be better" and bringing it to the people around you.
I know that's obvious and that would be in any business book, but I'm just saying that is my latest chapter and that's what I'm going through at the moment is I'm working with the team to figure out, "How do I proactively support you and make you better so that we can all deliver a better experience to our clients, which we owe to them?"
You know, I'll close on this note. I recently rewatched all of The Last Dance, the Michael Jordan and '90s Bulls documentary. And there's this famous clip from the end of, I think it's episode seven, where they're asking Jordan about sort of whether he was like a nice guy or a nice teammate or whatever.
And, you know, his teammates are like, "He couldn't have been a nice guy because like his job was to push everyone to do better." And, you know, that's a tough job, right? He had to raise the standard.
And that's like—you got to kind of be up people's asses to do that job, right? Like your job as the CEO is to push everyone to be better and to set up the systems and to own it when the systems aren't there, but then also to make sure people are implementing them and sort of proactively improving the product or the service for the clients.
That's a tough position to be in, in that you have to be relentlessly dissatisfied with the quality of what you're producing. If you as the CEO are not bringing that Math Around the World mentality of like, "We have to be the best, we have to be better, we have to achieve our potential," you know, you're not doing your job and you're not doing the service to your clients that they deserve. So they talk to Jordan about it and Jordan actually breaks down and, you know, cries in the interview because he's like—he says winning has a price, leadership has a price.
And for me, like that price is you're going to work until 11 p.m., midnight. You're going to wake up sometimes at 3 a.m. You're going to wake up then at 7 a.m., whatever your schedule is. And you're going to be thinking about the business.
This is it. Like, this is the thing. But for me, and this is what I would say to my 21-year-old self or my, you know, child self that was like, "What is the point of all this?" Like, this is the most fulfilling thing in the world that someone wired like an entrepreneur can do.
To be doing something hard, to be doing something where you are judged by the clients, where they say, "I demand better from you and your team," you know, "or I'm going to leave." That is the pressure that we as entrepreneurs court, right?
I want that. Give me that. I was listening to this entrepreneur on the My First Million podcast recently and he was like—they were like, "Are you stressed?" or whatever. And he was like, "I'm not stressed enough. I want it all. I want the work. I want the pressure. I want the responsibility." Because to me, that is the juice, right? The action is the juice, and that's the effing action. You know, when I was seven, I started to discover like an outlet for that—that energy and that drive.
And when I was 21, I was like, "I've, you know, given all this to school, to academics. I've given everything I can and I'm not happy with the results." And I think there are a couple of reasons I wasn't happy.
One was because it wasn't as measurable. Like that's what I love about capitalism and business and the market is like, it tells you the freaking truth. It's not like a professor being like, "Good job" or not, which is, you know, wishy-washy.
It's like, "This business is growing or it's not. Our clients are happy or they're not. You know, they're giving us their hard-earned dollars or they're not." And we're going to bust our mother effing asses to earn their dollar and to show them that we are the best place to allocate that capital and that they should trust us.
So getting that feedback from the market, from the customer, getting that truth, getting to measure it and get better, that is incredibly valuable. But the other part is people. You know, there are no great entrepreneurs who are freelancers.
And it's no disrespect to being a freelancer. That's cool. I did it. I think you can have an amazing life doing it. But the pursuit of greatness in business is not about you. It's not about "I'm an amazing writer."
Who gives an F? It's about: can you bring a group of people together and nurture them and challenge them to meet a higher standard that you set and then you continually raise? And if you can do that collectively, then you can maybe achieve greatness as an entrepreneur.
And that is where I'm at now, is trying to—trying to raise that bar, trying to become one-tenth as motivated and inspiring and hardworking as Jordan is in that documentary. And for me, building Sharp Pen these past five years, which will be five years exactly on August 20th, 2026, has been the most fulfilling experience of my life.
So if you're still listening, thank you very much. And if this resonated with you, I'd love to hear from you. And if you're an entrepreneur, I'd love to have this kind of chat with you. The 2 a.m. Entrepreneur Podcast is the new version of the AdTech Marketing Podcast, just for the special times.
Thanks, guys.
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