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The Audacity
A coming-of-age entrepreneurial story.


Chapter 1: The Rat Race

My alarm clock blared as I groggily opened my eyes, greeted by the view of an old brick ceiling overhead. It was 8:00 AM, Monday, September 11th, 2017. My first day as a college student had officially begun.

Although the grungy dormitory ceilings might not suggest it, I started college at one of the best schools on the planet – Northwestern University. A world-renowned institution with a 6.9 percent acceptance rate. I’d somehow been admitted six months prior as a local boy from Libertyville, IL, who grew up just 30 minutes from campus. A laughably short trip compared to my new neighbours who hailed from all corners of the globe.

Northwestern is an intense place; it is part of why it is so revered. Most colleges operate on two semesters, fall and spring. Northwestern works on four quarters, each a 10-week flat out sprint with no breaks. It’s a perfect breeding ground for competitive and ambitious 20-somethings with a point to prove. Imposter syndrome was so strong for me on Day 1. Socially, I knew I’d (eventually) belong. I was a charismatic kid who always found it easy to make friends. Academically and professionally, however, I felt intimidated from the get-go. 

All I wanted was to feel like I belonged. And early on, that desperate desire was a constant source of adrenaline. I was akin to a duck in water: on the surface, I was a ‘happy freshman’ who earned a 3.93 GPA in his first quarter. Underneath, I was kicking hard just to stay afloat, running across campus in full dress clothes to make my intramural volleyball games after business club interviews. This was the pace I felt I needed to move to survive the pressure cooker and ultimately prove that I belonged at this great institution.

My first day of college. Evanston, IL.

A year in, I thought I’d nailed the recipe for success. I’d earned exceptional grades and spots in top clubs, and thus I was able to chase prestigious summer internships with the best of my peers. My campus life was a full-court press of career fairs, employer meet and greets, resume reviews and countless conversations with elder peers and professors educating me on what the “best path forward” was. Who could want more?

The bitter truth was that I didn’t know what I wanted, and so hustling for a prestigious job was the perfect antidote. It was an ideal distraction from the more profound questions. It helped me mask the fact that I didn’t know what I was doing and, in a strange way, made me feel like I deserved to be at Northwestern. If my motivation ever waned, one look around the library late at night followed by a dose of social media put me straight. It was a daily reminder of everything I didn’t have but should want, and it created the illusion that everybody but me had their shit together.

No matter how hard I tried to ignore my self-talk, one question kept ringing in my ears late at night when I would finally stop moving. How could I ever get ahead if I didn’t even know where I was going?

A day in my freshman life. Evanston, IL.

Chapter 2: Plan B

By October 1st, 2018, I was officially doing too much: the adrenaline rush had worn off. I ran a student organization, played club volleyball, worked daily on landing my next prestigious internship, remained diligent academically, and worked to cobble together a healthy social life. On paper, my life was great. In reality, it was overwhelming. 

My time and energy were misplaced; I had no quicksand left in my timer. Waking up at 6 AM for 10-12 hours of consulting case prep and networking was a dark hole with no light at the end. I spent my days sitting inside sterile white rooms that lacked any sign of life or inspiration. Amidst the flurry of interviews, networking calls, casing preps, and info sessions, I eventually broke down. I couldn’t continue to push past the anxiety that consumed my every thought. I started crying and felt defeated. “Maybe I couldn’t do it all like everyone else,” I said to myself

The night of my breakdown, I made four phone calls. One to my parents, who knew me best. The next to my closest friend, who knew of my anxieties but was on a completely different life path. Third, a peer who was in a similar position to me. And finally, I called a mentor who knew of my desire to fit in and prove myself at school. Each conversation helped me realize that I was battling to stay on a path that I had no interest in. I decided to stop recruiting for a consulting job altogether after a few days of intense reflection. It just simply wasn’t worth seeing things through for a reward that I no longer felt I wanted or deserved to take from someone else.

Gracefully bowing out of consulting recruiting. November, 2018.

The unfortunate reality was that I didn’t know what I wanted. So, I did the next best thing, and followed what those around me told me to do.

What was I walking away from? At the time, it felt like everything. I was convinced my decision would immediately prohibit me from earning a six-figure income at age 22. I said goodbye to the flexibility of jumping into other high-powered careers at will and the ability to have any friend or parent nod in awe when I told them what I did for a living.

I struggled with this decision for a long-time. However, as time passed, I slowly began to appreciate its importance. After my second-guessing faded, I started congratulating myself for besting higher education’s default path. It became a personal point of pride that I’d dropped out of consulting recruitment, despite making final round interviews at multiple top firms. 

It’s time to settle in,” I said to myself. If only.

What if college, at its best, was a place to learn what I didn’t want to do just as much as it was a path to finding what I did?

Out in San Francisco chasing technology dreams. December 2018.

Chapter 3: The Relapse

Consulting was not my dream path. However, it had filled the void of what my future could hold. My added free time was perpetuated with constant self-questioning: “Who are you? What do you want to become? Why?” These questions felt scarier than they did when I started at Northwestern. My peers were solidifying their futures, and I was lost, no longer a wide-eyed freshman who could enjoy exploring different avenues. 

As one door closed, another opened, and I found myself walking right into the world of ‘Big Tech,’ leading a trip to San Francisco, CA, alongside 20 other ambitious Northwestern undergraduates in December of 2018. Every student on that trip hoped to work on the next big thing and felt like this time out West would bring us closer to the answer. For five days, we visited Google, Lyft, Dropbox, Facebook and YCombinator. It was an unusual way to escape my new reality and enjoy a new distraction that could justify my inability to answer the questions of who I was and the life I wanted to live.

And I must admit, at first, life in the mecca of innovation looked pretty sweet. At least way better than consulting. Sure, people worked long hours, but the benefits were insane – unlimited paid-time-off, ping pong in the office, nap pods, and a ludicrous amount of snacks and La Croix? Work sounded like play out here, and I was all about it. However, it didn’t take much scratching beneath the surface to find myself staring familiar traps in the face. Yes, Big  Tech would make me money and preserve my ‘optionality.’ But what was the catch? I soon learned through conversations with people on the inside that the grass wasn’t always so green. Ping pong tables and unlimited PTO didn’t mean much when there wasn’t enough time to utilize them, and working in The Bay guaranteed long commutes and a prohibitively expensive lifestyle. 

I spent time reflecting and talking to others before fully committing to this path. After listening to hours of insiders’ experiences, I gracefully bowed out before I dug myself in too deep. I learned so much from my conversations and consulting struggles that I didn’t need to second guess myself for weeks before feeling okay. This second trip on the ‘it looks too good to be true’ professional merry-go-round got me thinking: what if college, at its best, was a place to learn what I didn’t want to do just as much as it was a path to finding what I did?

The most fulfilled and effective people I know — world-famous creatives, billionaires, thought leaders, and more — look at their life’s journey as perhaps 25 per cent finding themselves and 75 per cent creating themselves.


— Tim Ferriss

Chapter 4: Shooting Your Shot (Plan C)

I had a new perspective on my career as a Northwestern student, and I was finally both ready and able to enjoy some downtime. I focused it all on everything I had previously neglected—namely, time with my friends and family.

My new life involved staying up late, making friends, cooking, playing video games, and reading as many great books as I could get my hands on. I read one such book called Tribe of Mentors, written by the lifestyle guru, Tim Ferris. It wasn’t a novel, a memoir or a biography, but rather a dictionary-like reference guide of answers to ten life questions from the author’s greatest idols – a blueprint for anyone else asking similar questions while discerning their future path. Late one night, I started reading the introduction and was immediately hit square in the face by a quote. It read, “The most fulfilled and effective people I know – world-famous creatives, billionaires, thought leaders, and more – look at their life’s journey as perhaps 25 percent finding themselves and 75 percent creating themselves.” 

I’d never thought about the idea of creating oneself before. I took the line to heart.

If building a media company was the reason I got into Northwestern, why wouldn’t it also be the reason I thrived while I was here?

Feeling inspired, I began reminiscing on an old high school dream of working with social media influencers. I grew up watching content creators daily and had always thought of them as role models and communities that transcended physical locations. I spent two years living in Portugal as a kid, and the best way I stayed connected to my friends back home was through video games and the content creators that helped make them famous. Without those influencers, I would have lost contact and connection to people I loved.

I’d also had extensive experience with the social media platforms these same creators live on. I spent all four years in high school working at a digital sports publication called TheLeagueNews (TLN). I went from unpaid intern to co-owner after my first year and led the website’s growth from 0 to 5,000,000 total views. My job was to focus on scale, and I turned social media into our growth engine. I found myself wondering: If building a media company was the reason I got into Northwestern, why wouldn’t it also be the reason I thrived while I was here? 

As these thoughts swirled around my head, I decided to whip up a cold email to my favorite creator at the time, @Jesser. Jesse was 19 years old and had a following of 3 million across all social platforms. As a basketball and gaming influencer, I loved his content ever since I first stumbled on his NBA2K videos back in 2014. I clicked send and hoped for the best. I assumed I’d never hear back.

My first cold email to Jesse.

Two follow-ups later, I was stunned to see a reply in my inbox.“Hey Mateo, not sure who you are or what you’re trying to offer, but sounds interesting. Happy to chat, here’s my number.” I was ecstatic! A wave of energy and excitement came over me. And then, nervousness. I had no clue what exactly I wanted to pitch. What I did know, however, is that I was fascinated by the way data was transforming the creator economy. Namely, the way creators made money from their 1,000 truest fans, and I’d leap at any excuse to learn more.

Jesse and I talked for an hour the next night, and I convinced him to let me work pro bono on a social media analytics project. On September 1st, 2018, I showed him my findings. He was so thrilled that I asked if he’d be willing to pay me $1500 for another phase of work. I essentially wanted to be paid like an intern. Was he willing? “Absolutely. Excited to dive in. Send over a contract.”

I continued working extremely hard, and for the first time since TLN, I’d found a professional opportunity that gave me more energy than it took. Three months later, I was out in Los Angeles dapping up Jesse at his mansion to present my final project. I’d told Jesse I was in L.A. for the week when in reality, I was sitting in my dingy dorm room back in Evanston, IL hoping to have an excuse to make the trip. Don’t ask, don’t get. My gamble paid off.

My time with Jesse was surreal. I saw a custom-built basketball court, a pool and a chrome-tinted Audi R8 in my first five minutes at the house. More importantly, I smashed the presentation I’d spent all night perfecting in a run-down Anaheim hotel room. Our scheduled ‘15-minute read-out’ turned into an hours-long conversation around content strategy, optimization, and business growth. They were some of the most productive and enjoyable two hours of my professional life. Before I left, Jesse took me aside and told me he wanted to find a way to continue collaborating going into 2019. He said there was a lot more money on the table and referrals if I could turn this into something bigger. 

As I walked out the door, Jesse asked me what my business name was. I didn’t have one. I sat there for a few seconds, remembering my dad and I jokingly discussing how a play on “AMA”— Reddit Ask-Me-Anythings—would be a great business name centered around influencers.“Authentic Media Ascension,” I told him. “You can call it AMA.”

I left with the biggest grin on my face: there was something here.

Jesse & I at an event he hosted in Chicago, IL. 2016.

Chapter 5: Success ≠ Happiness

AMA became an official LLC on April 4th, 2019. It was time to grow, and my biggest focus was proving to everyone that the idea had merit. I wanted Plan C to feel like Plan A. I loved the lifestyle I was carving out for myself. However, my energy started depleting at the rate of my consulting recruitment days. My early success did not always equate to happiness. 

For me, the original dream was to just get on the phone with Jesse. I was ecstatic those first few hours afterwards, and then my newest dream was to find a way to partner with him. Then it was making $5,000 in revenue. We hit that in January of 2019. $5,000 was impressive. But I told myself that $10,000 would prove that this business is legitimate (5 figures, baby!).  I jokingly told my friends I’d buy the same Versace Robe that Jesse had worn on our first-ever meeting together if we reached it. We hit that two months later, in April of 2019 (I never bought the robe). Was I now content? I wish. The evolution continued. The dream of $10,000 became $50,000 (achieved August 2019), which became $100,000 (achieved January 2020), which became $250,000 (achieved November 2020). You get the gist. 

I was experiencing hedonic adaptation. It’s the tendency of humans “to quickly return to a relatively stable level of happiness despite major recent positive or negative events or life changes.” In short, we satisfy our desire through achievement and then continually spawn new cravings, so we are constantly chasing the same feeling. Odds are we’ve all felt extraordinarily excited to receive or start something, only to not care about it much a few months later. Somehow, my dream company managed to hit every benchmark my peers and I had set, only to leave me staring toward the next big accomplishment. 

I can only describe it as being on a perpetual hamster wheel. My feelings of success, happiness, and self-worth started to plateau with each new milestone, while the expectations and pressure around maintaining AMA’s success grew. Publications wanted to feature AMA; we received invitations to podcasts and were told to apply to various pitch competitions. I was becoming more anxious overall as the business was growing. My success and happiness were in an inverse relationship, and it confused me greatly. Because, if you told me the first day I started AMA that it would become a half-million-dollar business, I would a) have not believed you, and b) when I finally did, done a million excited laps around my house.

I learned the hard way that if you don’t define what you want or what you should do, someone else will do it for you.

My first big contract. December 2019.

The mistake I made with AMA was the same mistake I made when starting Northwestern. I used it to chase feelings of belongingness by allowing others to define my path. Freshman year, I believed a consulting job was my golden ticket to happiness. I spent my sophomore and junior year working on AMA in pursuit of revenue gains at all costs. Regardless of where it came from or the work I needed to do to earn it, I told myself it was worth it. It wasn’t.

I learned the hard way that if you don’t define what you want or what you should do, someone else will do it for you. I was so caught up in achieving the next “milestone” that I didn’t pay enough attention to what work people were asking me to do and who I would be able to do it with. I was sitting on Zoom with clients who were paying us less money and yet most uninterested in the work we were doing. And if I’m really honest, I accepted it in part because I knew the experience would still look good on a resume, should I ever decide to dip back into the corporate world.

My true joy came from the team I was building internally and the opportunities to engage communities, not just grow them. I still remember the first cold email I received from a Northwestern freshman asking me to join AMA. Jesse and I had officially switched places. I also found a business partner at school with as much knowledge and energy as I had. We wanted to grow this thing to the moon. And thus, I began to reshape AMA’s vision and team around where my energy came from instead of others with no skin in the game. We weren’t just an analytics agency. I didn’t want to just work with creators and run backend data analyses. We were a creator growth studio—an organization dedicated to helping creators engage their growing communities while staying true to themselves.

Company life was no longer about hitting the next revenue target but instead finding the right influencer to partner with. And I discovered that prioritizing the latter was a more efficient way to achieve the former. For example, I’d maintained a relationship with a creator for a year simply because I loved talking to him. One day, it unexpectedly turned into a $50,000 contract. This wasn’t just a one-off-case example, either. Building genuine relationships with creators led to the creation of numerous opportunities. Ultimately, it was the tool I used to start defining my own goals with the same excitement, passion, and curiosity I had at the very start.

The early AMA Team. Chicago, IL.

Chapter 6: Pandemic Life

Learning how to prioritize my excitement and curiosity while growing the business put AMA in a perfect position to thrive when COVID-19 hit. As other parts of my life began to change completely overnight, the same chaos didn’t exist with AMA. We’d always worked remotely, and the pandemic made collaborating with creators even more accessible given the immediate influx in social media viewership. From April 2020 to March 2021, we made $250,000 in revenue. Our team grew from three people to seven, and we all made the most of our time in quarantine. 

We put our heads down, and the business thrived. A year later, in March of 2021, I was ready to come up for air. The vaccination rollout was going well in the United States. I was on the verge of graduating and getting ready to embark on a dream six-week trip around the United States with my girlfriend. The only thing I had to take care of before I left was a conversation with my co-founder. He was deciding whether he would join AMA full-time after graduation, and I was pretty confident he was in. After all, we’d just had a record year. Everything was going in the right direction. Until suddenly, it wasn’t. Three days before I was set to leave, I got a phone call from Jesse. Recent external problems had tanked his revenue, and he needed to cut costs. As much as it hurt, we were going to be a part of those cuts. Shit. Not even 8 hours later, my partner was told he could no longer defer his job offer (at a consulting firm, of course). Between that, the Jesse news, and other external factors, he decided not to join AMA full-time post-graduation.

This was extremely challenging to process. And the timing was just horrible. I’d planned on doing zero thinking about work or school on my trip. Life had other plans, and I was thrust into a mental cloud of doubt about my future. Was it worth continuing to venture down the entrepreneurial path? Would I be able to continue the success of the company without my partner? I knew I’d miss my co-founder sorely, and there was no replacing AMA’s Day 1 client. 

Our trajectory shifted radically overnight.

Chapter 7: New Mountains

Today is May 26th. It’s my 22nd birthday. I submitted my last ever college assignment almost two months ago, and I’m three weeks out from graduating from Northwestern. When I started college, I was an insecure kid desperate to not feel like an imposter. I spent my time in a perpetual rat race where accomplishment solely begot accomplishing more. I’d climb to the top of one popular mountain, only then to glance at the next horizon with an even higher summit. 

Today, I’m still insecure. But my insecurity doesn’t stem from what’s on my resume or how much money I’m making at age 22. I’m not scared about climbing the mountain with the tallest summit. Instead, I’m focused on whether the mountain I’m ascending is the right one while constantly questioning whether I have the right tools in my sack for the journey. I no longer use imposter-induced adrenaline rushes to fuel my work. Instead, I simply pursue the things I genuinely enjoy: quality time with friends and family, travel, and building digital communities.

A close friend once told me: “Run fully to something that fulfills an absence as opposed to running away from something causing distress.” Four years later, I think I finally understand what it means. Running something successfully has taught me that an experience won’t be perfect forever. Hence why I no longer run from the unknown. Instead, I try to live in the uncertain and find a way to thrive in it. After all, there are almost always some fantastic rewards on the other side. 

Even without my co-founder or Day 1 client by my side, I’ll be working full-time on AMA post-graduation. I feel confident in my love of the space, the vision for the business, and our team’s incredible chemistry. The corporate world will always be there. An opportunity like this likely won’t.

Mateo is an entrepreneur. Follow the next chapter of his journey here.

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