On the Virtue of Career Transitions (Part 2 of 2)

Becoming an Angel Investor and Venture Capitalist

In my previous blog, I summarized the non-linear career path that allowed me to explore various job functions, sectors, and organizations that piqued my interests over the first decade and a half of my postgraduate working life. Entering the next phase after my somewhat circuitous journey has allowed me to “settle in” to what I see as a more stable and focused period of my career. Having remarried and started a family, I have in tandem begun anew as a professional venture capital investor. In this, I feel as though I have found my calling. I am often asked by students and young professionals how to break into VC. I definitely don’t believe there is a one-size-fits-all answer, but I can certainly share my experience and observations.

After a number of years living abroad in Europe (primarily in Amsterdam, but most recently in Barcelona), I relocated back to the US and my hometown of Boston in 2016. I stepped away from the company I had co-founded, TravelPerk, after helping get the company launched, putting the founding team together, going through our initial pivot, and raising our first round of external funding. As much as I believed in TravelPerk, I had a mom back home who was in the early stages of Alzheimer’s and I was an only child who was coming off of a divorce a couple years prior. It therefore didn’t make much sense for me at a personal level to remain in Europe. I had two very capable co-founders whom I knew would keep the company’s heart beating strong.

As I came back stateside, in addition to helping my dad to care for my mom, I took a breather to consider what would be next for me professionally. I had several possibilities in my head for what I thought would be a good fit for me. I knew I wasn’t ready to start a new business as I didn’t have a burning vision that I was anxious to execute. However, I did consider several paths: a) buying and operating an existing business, b) working as an executive search consultant (i.e. headhunter), and c) getting into VC, which had been in my head for many years. I thought the latter might be the most difficult to achieve as I was not on a traditional linear path into venture capital and most of my VC connections were in Europe at the time.

After about six months of personal deliberation and consultation with both confidantes and professional career coaches (primarily through my alma mater, HBS), I landed on my strategy. I would simultaneously seek to own an existing “Main Street” brick and mortar business that would generate income, while I also would dip my toes into angel investing. Both of these pursuits go back to my college studies as an entrepreneurship major at Babson College.

I recall thinking of “angel investors” as mythological high net worth individuals who had the ability and means to make risky bets into the most cutting edge technology companies on the planet. By the early 2000s, I saw more cases of folks like Andy Bechtolsheim, who put $100,000 down on the founders of Google and turned that investment into billions while barely having to lift a finger… I thought if I ever had the ability to become an angel investor, I would do it!

The “better hedge your bets” side of my brain, however, told me that steady passive or semi-passive income was also the way to go. I knew that it was possible to buy small lifestyle (or “Main Street”) businesses for something on the order of just three times annual earnings. That seemed like a pretty reasonable risk-return profile to me. Just keep things going as they are and you can have yourself a nice, steady flow of income on the side. I was privileged at Babson to have also taken an elective course on franchising that was taught by the co-founder of Jiffy Lube, Dr. Stephen Spinelli, who more than 25 years later, is now the president of the college. With his brilliant command of classroom discussions, I was inspired to consider franchising as a risk mitigated pathway into small business ownership. This was the point in my career where I had the first real chance to explore this.

I ultimately acquired what would be the first of three existing Elements Massage franchise locations in Massachusetts. I took a semi-passive approach to this in the first couple of years, which later became almost fully passive after I hired a General Manager to oversee nearly all aspects of these businesses. This experience has had its ups and downs and I chronicle some of my reflections and advice for others who may be contemplating buying a small business or owning a franchise.

While I was acquiring and diving into my Elements businesses, I started to make my first angel investments. These were initially bets on entrepreneurs whom I knew personally or had been introduced to by friends. Some were in travel technology (e.g., Groupize), which is where I had cut my teeth, while others were in sectors such as construction technology (HaulHub), where I had less familiarity but believed in the founder. I also joined a local angel group and invested through a European investor syndicate as I was exploring and discovering.

In looking how best to build a portfolio strategy, I came across Yard Ventures, then a relatively new VC fund for individual accredited investors that was marketing itself to the Harvard alumni community. What I found most interesting was that this would be an opportunity to invest not just at the angel or “friends and family” stage, but it would allow me to gain access to a stage-diversified venture portfolio. Further, I would not have to rely just on my own industry knowledge or contacts to gain access to quality venture dealflow.

My investment in “Yard Ventures Fund 2” paid early dividends with a couple of unusually quick positive exits. I became more interested in the model and started developing a closer relationship with the team. This led to my joining Yard’s investment committee and later in 2019, I was offered the opportunity to come and work full-time on the fund. I guess one could say, “the rest is history…” I have remained with Alumni Ventures for going on six years, where I have transitioned from the Yard team to now leading the AV Seed Fund.

I wrote at the beginning of Part 1 of this blog that I feel like I’ve had “career ADD,” where I’ve been searching for new challenges and opportunities. Venture capital, however, presents just that each and every day. I am not only continuously learning something new about emerging technologies, but I get to interact with dynamic entrepreneurs and talented investors who help to sharpen my own thinking and skills. No two days are the same and I look forward to going to work each day and seeing what can be accomplished. There is also rapid gratification from our team making investments at the pace we do of roughly one deal per week, as well as fulfillment from knowing that many of these investments will pay dividends not just financially but for society as well.

In taking a non-linear approach to entering the VC profession, I have been able to leverage my experiences and connections from across my career. People who were my colleagues in my first job at Lycos are now also in VC and are entrepreneurs themselves. Folks I crossed paths with at McKinsey, Booking, and elsewhere during my career have also reappeared in my professional circle in a variety of surprising and beneficial ways. Truly serendipity.

There is something to be said for choosing to go wide, but also deep within limited confines. We sometimes call this being “T” shaped… you can be a generalist, while also having some areas of focus and special interest. For some, the linear path of growing vertically within a specific company, industry, or function makes perfect sense. However, there are non-linear paths that can work out very well too. I feel grateful and satisfied with where I am and for the trajectory that’s gotten me here. I hope others who also feel like they are still figuring it all out will take inspiration in knowing that they do not have to follow a “traditional” playbook to achieve satisfaction and that there need not be one straight path to achieving one’s highest professional aspirations.