The 5 Biggest Lessons I Learned Leaving a Corporate Job for a 2 Person Start-Up

Gregory Matarazzo Jr.
8 min readSep 8, 2020

The disruption of the COVID-19 pandemic has been painful for many. My heart goes out to the healthcare workers on the front lines and all essential employees. For me personally, as someone already working remotely since 2017, social distancing has created unforeseen down time. With that — I’ve been reflecting on the last few years of my life, and how I ended up where I am today, and decided to sum up some of my learnings. I hope this invokes a voice in you to tell your own story. It can be both therapeutic and comforting in a stressful and unpredictable time like this.

It’s truly been a whirlwind few years, and both the tech industry and personal changes I’ve seen are incredible. Looking back on it now, it was a time of huge growth — some of it challenging, some of it uncomfortable, but all of it valuable. If you’re on the brink of major changes in your own life, I hope you find something useful in my story.

And please, let me know if there’s some other way I can help. If you’re looking for work, perhaps I can review your resume or reach out within my network to find opportunities. I’d be happy to. It’s a difficult time, and we all need to look out for one another.

So… how did I get here?

A fateful text message

It was the summer of 2017 and I was working in Manhattan for a tech company that employed over 300,000 workers across the world. It was both challenging and rewarding — the high-point of my career at that point. Landing that job had taken years of hard work, a roundtrip commute of 5 hours each day, and some very lucky breaks.

Big media and large tech companies were all I had known in my nearly decade-long work history. Each step had led me to a company whose overarching ideals and vision I both admired and shared. This is all to say I had no plans to leave. I felt enormous gratitude for my job, and saw myself there for the far future.

Then I got a text message from a longtime friend: “Hey, we’re building something pretty special. You interested in joining?”

It’s the sort of pitch I might have ignored if it hadn’t come from such a trusted source. I’d seen this particular friend thinking big and executing over the years. I trusted his vision. Soon we were chatting on the phone, and in spite of myself, I found my interest was piqued. The “something special” was a new take on digital marketing — a special consultancy-agency hybrid that offered clients the best of both worlds. All results, no fluff.

Coffee near Penn Station

My friend’s business partner / co founder and I arranged a quick, impromptu meeting. Within a few days, he and I were talking shop in Midtown Manhattan — and I was getting more excited by the minute.

It turned out they had founded the company just a few months before, and growth was coming quicker than expected. My friend and his partner needed help. Fast. I know the cafe around us must have been bustling, but I was rapt, laser-focused on this conversation.

The vision for the company was well expressed. The current client base was impressive and promising. We discussed the work that needed to be done and I shared how I could contribute. After talking for an hour we parted. I had very little doubt that the business would succeed. But what would it mean for me to become part of this wild new venture?

The decision

In any big life decision, there are endless considerations. What are the opportunities? What are the risks? What are the unknowns?

But ultimately, when I weighed up all the pros and cons, this decision ended up feeling surprisingly simple. With only myself to support, I was in the position to take a risk. And most importantly, I believed in the people, the mission, and myself.

And finally, I figured, if I ended up being another techy millennial with a failed startup under my belt, at least I’d be in good company.

Jumping on a moving train

Joining the new company was a learning experience nothing could have prepared me for. In classic startup style, we had a tiny office — so small that the backs of our chairs touched. We had to shimmy past each other to get out of the room. And the view from our window? A blank brick wall.

I’d be lying if I said that wasn’t challenging at points. There were certainly moments, staring out the window at that brick wall, where I wondered whether I’d made a smart decision. But fortunately I never had long to dwell on that, because we were hustling all the time. This was the other ‘classic startup’ aspect of my experience — and it was 100% invigorating.

With three people, there’s no downtime. We were constantly in motion — building off each other’s ideas, handing off responsibilities, innovating new approaches. For someone used to the rigidly defined roles of a 300,000 person corporation, this was totally new to me. Everyone did everything. I interviewed candidates, pitched clients, built and presented presentations to packed boardrooms, fixed tech issues, etc. I learned the business end to end.

At my previous job, I’d become used to the phrase “a lot of red tape” meaning it was challenging to get approvals or signatures for certain work streams or projects. But in this new gig, nothing was off limits. We gave ourselves complete freedom to think, do, and implement. Not only was the red tape cut, it was doused in kerosene and set ablaze. On more than one occasion back then, you could find all three of us running through the NYC subway, trying to make a meeting that the business hinged on. Those were crazy, stressful, exhilarating times.

Growth & more growth

The business and team grew quickly over the next 2 years, from 3 to 5 to 10 people. The team became a remote workforce spread across the country, from NYC to Atlanta to San Diego. During this time, I relocated and settled into working remotely from Missoula, Montana. Trading that brick wall view for one of snowy mountain caps and pines — I still feel unspeakably grateful to take in this view each day and be part of such a generous community.

By 2019, our client portfolio was booming with Fortune 100 companies and $1B+ startups, our results were unquestionable and our team was stacked with talent. We quickly became an acquisition target, and by the end of the year, it happened — the business was acquired by a leader in the Digital Growth & Strategy space, Power Digital.

Our team of 10 was absorbed into a company of more than 100, and a new chapter was underway. To everyone’s delight, the teams could not have been more complementary to each other. The team we joined was not only incredibly talented and scrappy, it was driven by an earnest and inspiring mission. This is perfectly highlighted in the company’s philanthropic arm, Empower Digital — a group that organizes initiatives to support our communities. Most recently the initiative brought together businesses and consultants to provide pro bono services (Accounting, HR, Digital Strategy, etc.) to Black-owned businesses.

When I got that first text message three years ago, I could never have imagined I’d end up here. And yet, looking back on it now, it almost feels fateful. And that’s why, today, I find myself trying to boil it all down.

So, what did I learn?

Condensing several years’ worth of life lessons into a few bite-sized pieces isn’t easy. After all, growth is complex and multi-dimensional. With that, here are the five learnings of my big career move that have risen to the top:

1. Don’t complain about it, change it

When you’re in a three-person company, there are no illusions that “someone” will fix broken processes or clean up messy outcomes. There are no contingency plans or committees to delegate to. Either you do it or it doesn’t get done. This is an exhilarating change that’s also a little scary. When you have complete freedom to think up and implement changes, with no red tape to slow you down, the only limit is your good judgment. Living up to that responsibility brings out the best in us.

2. Bite off more than you can [supposedly] chew

For the company, the word “no” just wasn’t in our vocabulary. When clients told us their needs, we agreed knowing we’d figure out how to do it. In fact, I can’t point to one instance in where we failed to deliver. It was the first time I’d seen this gritty “figure it out and get it done” philosophy in action. Sometimes this involved learning a new skill from scratch. Sometimes you went deep in the forums and did original research. Frankly, this can be a hugely taxing work ethos — but it’s ultimately incredibly rewarding for both you and your clients.

3. Expect discomfort

It’s easy to pay lip service to the idea of leaving your comfort zone. But the reality is hard. And yes, it’s worth it. Joining a new team, taking on new responsibilities, and learning new skills has been incredibly challenging. But that’s how we get to fresh perspectives, innovation, and a deeper understanding of our professional industries and ourselves as a whole. Leaving the comfortable structure and rigid confines of any situation allows us to build on parts of ourselves we might otherwise overlook.

4. Your gut is your best friend

Intuition isn’t always right, but it’s always worth listening to. Marketers like to imagine that there’s a process or algorithm for answering complex questions. But the truth is that every situation is unique — and data is meaningless without human wisdom to ground it. And this becomes abundantly clear in small organizations, where you’re solving new problems every hour. In these situations, trusting your gut is essential. Every complex decision must combine basic facts with due diligence and creative thinking.

5. Ask for support & you’ll get it

The people around me were amazingly supportive of my career move. Were there countless unknowns and some serious risks? Absolutely. But no one told me I was making a mistake, or doubted my judgment. The flip side to this is that you shouldn’t make big decisions alone. People supported me because I involved them in my decision, asked for their advice, and listened carefully — whether they were in my trusted circle or more neutral parties giving unbiased opinions.

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Gregory Matarazzo Jr.

When I'm not out hiking mountains near my home in Montana, I am a Certified Meditation Teacher, volunteer with The Special Olympics & a Digital Consultant.