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

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

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

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

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

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

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?

1. Don’t complain about it, change it

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

3. Expect discomfort

4. Your gut is your best friend

5. Ask for support & you’ll get it

I currently live in Missoula, Montana and focus on Brand Growth and Digital Strategy.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store