Moving From Corporate to Start-Up

Michael Spalding
9 min readJan 17, 2021

Several months ago (pre-pandemic for reference), a new contact asked to meet for coffee to discuss how and why I transitioned from a large corporation to a startup. Until that point, I had not taken the time to reflect on this significant change in my career. After that meeting, I realized that my transition was not typical and could help others at a similar crossroads in their careers.

Before I begin, I want to be clear that I would not change what has happened throughout my career. I am grateful for the experiences I had and fully acknowledge that I would not be where I am had it not been for them.

Instead of looking negatively on parts of our past, why not look at it differently? Our past experiences, both good & bad, is what made us who we are today. — Nishan Panwa

I started with AirTouch Cellular in 1998 when I was 23 years old. I was an entry-level employee and thrilled to be working for a large company with good pay, great benefits, and on the cutting edge of technology at the time. The work was fun and thankless. I quickly advanced through various roles and became a people leader about two years after I started. I gained responsibility, compensation, and experience along the way.

Photo by Hunters Race on Unsplash

After about ten years, I seemed to hit a plateau. I had progressed to a mid-level managerial position and enjoyed my work. However, this is where I began to see the heavily political nature of a large company. Peers were not friends; they were competition. Collaboration was preached, but one-upmanship was the norm. Sure there were times where teamwork trumped individual recognition, but that was rare. I continued to put my all into my work, sought out feedback and guidance for success and advancement while keeping my positive outlook for the future.

The company was going through changes, as one does, and these contributed to my growing dissatisfaction. The culture was shifting away from what had drawn me to the company. In July 2018, Suzanne and I made the decision that I would resign and return to school full time. I gave my notice and felt freer than I had in years. My favorite question from my soon to be ex-colleagues was “where are you going?” The response of returning to school or taking a breather did not usually satisfy them. Most did not comprehend my desire for something different or my willingness to give up a great salary with no job lined up. People usually left the company abruptly “to pursue other interests” (aka fired) or for a “better job” at another large company.

I was confident in my decision. Suzanne was extremely supportive in every possible way. I had enrolled at Georgia State University before I gave notice and was set to begin classes full time about a month after my last day of work. I had begun writing the next chapter in my career under my terms.

Attending class daily was exciting and I dove in headfirst. I was a 44-year-old full-time student surrounded by people who were my kids’ age — I could have easily been mistaken for an instructor. While I was not learning anything that would directly benefit me professionally, it fulfilled me. I took a full class load my first semester and picked up a part-time job teaching English to Chinese children online (that’s a story for another time). I was also fulfilling my role as a stay-at-home husband and father by keeping the house together and making dinner almost every night. I stepped up my volunteer work with our favorite organizations. I registered for classes in the spring keeping a full class load and targeting graduation in December 2019.

Anyone who stops learning is old — whether this happens at twenty or at eighty. Anyone who keeps on learning not only remains young but becomes constantly more valuable — regardless of physical capacity. — Henry Ford

My days were full of things to do and I was sleeping well at night. I was more content than I had been in years. My days were full, however, my mind was restless for more challenging activities. I began looking for jobs.

Having not looked for a job in almost 20 years, I felt like I was fumbling through an endless pursuit of promising opportunities. I had some interviews and received multiple “thanks, but no thanks” emails. Then I stumbled onto an opportunity with a start-up that I had not heard of — Bellhops. I applied and received a call for a phone interview soon after. After successive phone interviews, I was invited into the office for a presentation and face-to-face conversation. About ten days later I received a text and phone call with an offer. After multiple conversations and a visit to company HQ in Chattanooga, I accepted and began a few weeks later.

Photo by Headway on Unsplash

My first week was amazing. I was in an environment where everyone is all-in for the company's purpose. I felt it in meetings with my boss and peers. I also heard it on the phone calls with customers from the frontline employees. I was blown away by how hard everyone was working to get stuff done. The energy was infectious and it confirmed I made the right choice.

Through this transition, I was not cognizant of the amount of change I was going through. Each obstacle seemed to be its own thing and not related to the larger change I was undergoing. In reality, they are all very much related and intertwined. Looking back on it, there were several key lessons that I feel are worth sharing.

Age is just a number. I have no official knowledge or data, but I think it’s safe to say I am the oldest employee at my current company. At first, this really disturbed me. Not only did I have more years of work experience than years of life of some of my employees, but I was visibly older. While I believe this age difference earned some respect, it also made me feel extremely different from those around me. Over a couple of months, I was able to accept this difference as an asset. I had already walked many of the same paths we were going down as a team. My knowledge and experience were clearly strengths and differentiators in a positive way. Yes, I was clearly the old man in the office, but I leaned into it. I have no issue acknowledging that I’m lost in some cultural references or that my kids are older than some of our team members. One peer even referred to me as FROG (favorite really old guy). In the end, my age is what I make it — an asset or a liability.

Peers are partners, not adversaries. I had come from a company that had 750 times more employees than my current one. My peers were more likely to be the competition for the next job (and sometimes my current job) than allies working towards a common goal. It wasn’t seen as bad, it was just a fact of life in that environment. Since this was my reality for 20 years, it makes sense that mindset carried with me into my new job. I remember the exact moment when I shifted from that view to one of true partnership with my peers.

I was having a casual conversation with a peer in the office kitchen about a month after I had joined the company. I was still the new guy and forging relationships with everyone. He had made a comment that I interpreted as him trying to make me look like I had made a mistake resulting in poor team performance. That conversation stayed with me throughout the day. At home later that night, it was still gnawing at me. But there was a revelation that smacked me that evening. He was and still is, one of the nicest people you will ever meet. This guy, my peer, who was significantly younger and less experienced than me, was not out to get me. His comment was simply feedback and meant to help me and my team improve. It was not shots fired or him trying to drive the bus over me. We were all running towards the same goal and he wanted to make sure we got there together. At that moment I realized that I need to immediately change my view of those around me.

Since then I had viewed every relationship at work through this lens and it has changed everything. The guy from the kitchen has become a trusted colleague and we partner on projects frequently. We have a common purpose that we were all working towards — we’re all in this together.

Mistakes are the ultimate learning opportunities. This lesson took a little longer to breakthrough for me. People always say that failures and mistakes are to be learned from, but that’s not how they are always perceived in a corporate environment. They can easily become stains on your name or worse, ammunition for others to push you out of a job or organization. In a start-up environment, we make mistakes daily, if not hourly. The speed of the work is so fast that decisions and actions come quickly. And while we strive to ensure we make the best choice, sometimes we miss. The good news is that’s ok — we can correct it and continue forward. However, taking a moment to understand the why and how of the mistake are critical in that learning.

One of the most powerful acts I have found is taking accountability for the action and charting the next steps out of the issue I created. It shows ownership and commitment. And it’s just the right thing to do. I have made many, many mistakes in my time at a start-up, and here’s how it usually goes: an issue arises then my leaders ask what’s going on and what I’m going to do about it. I try to respond as quickly as possible that I’ve got it and will get back to them by X day/time (usually that same day). After I investigate and I find that a decision by my team or a gap in a process we did not anticipate lead to the situation, we’re in full learning mode. I clearly take ownership for what occurred and outline the best way to make it right for the customer. I then strive to understand how we let it occur — was it a poor decision or a poor process? Once I know where the gap is, I can create actions to remedy those to prevent the same or a similar issue from occurring again. I then close the communication loop with my leaders informing them of what I’ve found, our actions for the customer, and how I prevent a recurrence.

I know most people are thinking “That’s the way it should be” and you’re right. It is how it should be and it is how it works for me now. In my past experience, this was not the case. Instead of taking ownership, making it right, and moving forward, it was usually about deflecting blame because this one incident could impede your next promotion or result in you receiving a write-up. While I learned a lot in that former environment, I have learned much, much more in my current situation. The bottom line: taking ownership and action because of a mistake or oversight as a leader shows your integrity and provides you an invaluable lesson of what to do (or not do) in the future. Don’t squander these opportunities that mistakes present to you.

I said at the beginning of this article, and sincerely mean it: I am extremely grateful for my experiences and am fully aware that they are what have led me to where I am today. I am in no way am trying to say that all large corporations are bad and that all start-ups are the best thing ever. I feel compelled to share my experience in transitioning between them because I am sure that others will walk a similar path. We owe it to those around us to be a guide.

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