A Reverse Resume

Dave Cahill
Mar 21 · 6 min read
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I have always found that a standard resume falls short telling the real story of a person’s “career”. It usually only features the work highlights, omitting the formative personal moments, failures, and challenges that are probably more responsible for making you, you. It recently struck me that a “reverse resume” of sorts could attempt to fill in the blanks between the LinkedIn worthy milestones, surfacing the messy and often non-linear stories that uniquely binds together the carefully curated set of experiences that we choose to put forth in a resume. Wanting to test it out, I figured I would take a shot at my own reverse resume. So here goes…

Let's start with my senior year in college. In the fall ’00 semester, I landed an internship at a large tech company just outside of Boston. I figured if I did well I could set myself up for a job upon graduation. My plan worked and I got offered a full-time role. Unfortunately, my first-day fell smack in the middle of the ’01 internet bubble bursting. When I arrived at the office on day one I was told there was no more position for Dave.

Suddenly armed with a lot of unexpected free time that summer I decided to travel, exploring London & France with my “friend” (as in, we weren’t dating at the time) from college, Sue. One incredible trip and four years later we would get married. It’s funny how that worked out.

Around July of that year, thanks to the persistence of the team I previously interned with, I landed a job at that same company that let me go months earlier. I spent a few great years there helping to build a new product. But eventually, I started to get bored with that role and began to look for other opportunities. Fortunately, I was able to move to another team within the company. Unfortunately, early on in my new job I naively sent an email outside the company that I shouldn’t have and got let go. Idiot.

After a few months of unemployment, through the help of a friend, I was able to find a job at an investment bank…but the role was based in Memphis. Just engaged in February that year, I somehow convinced my wife-to-be that it was a good idea to pack up and move to Tennessee. Taking one for the team to support me, she quit her job and off we went. We got married a year later.

Unfortunately, Tennessee was short-lived. We only lasted 2 years. While there I developed a really bad case of ulcerative colitis. My condition plus Sue being pregnant with our first child meant we were moving back to Boston to be closer to our family (and better doctors). Thankfully I had a great boss who was willing to let me continue in the same role from there. Once in Boston, I got the medical care I desperately needed and we set out to build a house and a family. At the time we approached the home design like it was our forever house. By mid-‘08 we finally moved in.

In the summer of ’08, I was getting the itch for something new at work after four years in the same role. After looking around a bit, I decided to jump from the sell-side to the buy-side of the investment world. If only I could have predicted that Lehman Brothers was going to declare bankruptcy less than a month into my new role. This marked the beginning of the ‘08/’09 financial crisis and the 2nd recession of my professional career. We also welcomed our 2nd daughter in September of that year.

Our fund managed to survive that initial downturn but we had no idea that another one was coming right behind it. In late ’10 the firm got caught up in a broad, and very public, FBI investigation into insider trading. This culminated in a raid of our office in November of ’10. Continuing with the pattern of our other kids being born during either a personal or economic crisis, my wife had just given birth to our third daughter a week prior.

Not surprisingly, the fund didn’t survive, closing in January of ’11. I was again out on the street and looking for work. Needing to find a way to pay the bills, I started consulting with several tech companies. Ten clients and ten months later I had created my own little consulting business, Diligence Technology Advisors. Never had more fun, never worked harder. But I knew consulting wasn’t a sustainable model for me then. So I started to think about which of my clients I might be able to go work full-time for. Eventually, I narrowed the list down to two. Of course, neither of them was located in Boston.

After visits to both California and Colorado, Sue and I decided to make the risky move to pursue an opportunity with an early-stage startup in Colorado. After some incredible ski vacations growing up, Colorado was always on my radar as a place to live but never thought it would actually happen. With our girls' ages 1, 3 and 5, we reasoned that this was a good time to at least try out another location before we started to really put down some roots. We put our “forever” house on the market and started packing.

April 23, 2012, we moved into our new home just outside of Boulder. The move turned out to be an absolute home run. A perfect fit for our family and lifestyle. The job worked out too. Fast forward to December of ’15, about 4.5 years after the move, and the startup I worked at got acquired. Being a part of building that team, that culture, and that company was an incredibly rewarding experience.

While a lot of employees stayed on-board post-acquisition, I needed a change of scenery. With the help of our previous investors, I was able to find a new early-stage opportunity. The idea of jumping back into the deep end of the pool in a new market intrigued the hell out of me. In August of ’16, I took the job. The only problem…it was based in Berkeley, California.

Going in, the thinking was that we would move to California. However, after a few house tours, we quickly came to our senses. We made the decision that I would commute instead. This meant weekly Tuesday to Thursday trips into Oakland Airport. While not without a high tax on our family, the equation was simple for us. The upside of our Colorado setup outweighed the downside of commuting.

Just two years into this new startup, including a comprehensive and painful education in how to bring a complex product to an emerging market, we managed to get acquired by one of the largest technology companies in the world. Eighteen months later and I am still here.

Over the course of the last four years, due to the commuting setup, I have spent way too much time in planes and hotels. Over this period I have learned to better manage the stress of traveling and being away from the family, by using free time to do things besides work. This includes reading, writing, listening to podcasts, exercising, or exploring the local vibe of wherever I may be. Earlier in my career, I definitely wouldn’t have the confidence to make this kind of tradeoff.

This finally gets us back to March 2020. Enter COVID-19 everywhere, and then right behind it, the 3rd recession of my career. Adding it up so far and you get 3 recessions, 3 moves, 3 different industries, 3 times being laid off or fired, 3 daughters, and 1 amazing wife without whom none of this would be possible. The lessons I have learned and the perspective I have developed throughout are invaluable. Unfortunately, they are also mostly invisible from a standard resume. Hopefully, my reverse resume changes that a bit. As you can see, from start to now it was certainly not a straight line but then again, what fun would that have been? :)

Dave Cahill

Written by

Work in AI GTM @Microsoft, former COO @BonsaiAI, VP Corp Dev & Prod Mktg @SolidFire. Live in CO but roots in Boston.

Not a straight line

Legendary Boston Globe sports writer Bob Ryan had a frequent column he would write called Emptying Out the Desk Drawer. This is sort of like my version of that across a range of topics that make their way through my head. Taken together they definitely won’t form a straight line.

Dave Cahill

Written by

Work in AI GTM @Microsoft, former COO @BonsaiAI, VP Corp Dev & Prod Mktg @SolidFire. Live in CO but roots in Boston.

Not a straight line

Legendary Boston Globe sports writer Bob Ryan had a frequent column he would write called Emptying Out the Desk Drawer. This is sort of like my version of that across a range of topics that make their way through my head. Taken together they definitely won’t form a straight line.

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