I Resigned - What's next?


On Friday, September 6th, I worked my last day for Bowdoin College, and perhaps my last day for a traditional employer (always with the caveat that if Barak calls me for a favor, I’m in). What started in 2015 as a burning desire to provide a more abundant lifestyle for my then-unborn daughter, turned into constant research, which turned into an ever-growing side-gig, which turned into me giving two weeks notice two weeks ago.

That feeling of excitement at meeting new people and new possibilities is back. While I had great co-workers, my desk job had become monotonous and frustrating. I am now ready to wrestle a grizzly (a very tame, trained, declawed and de-fanged grizzly)…It would still win. But you know what I mean- I’m pumped about what’s next. What is that you ask?

First let me take us back to 2015. Rommy, my wife, is pregnant with our daughter (hurray!). Soon I will be the only bread-winner for an undetermined amount of time. While my job in development at Bowdoin College paid all the bills, we weren’t saving meaningful amounts of money and any non-profit job would not do much more than pay bills. I wasn’t willing to ‘sell out’ and use my MBA for a bland corporation. While I had already proven adept at investing my paltry savings in the stock market, tripling a very small amount of money is still a small amount and not a reliable source of income. Nor is writing (though I hope to have more time for this now!).

At Carleton College in 2003, I took a life-changing class called Building the Eco House taught by our Director of Facilities, architect Richard Strong. J-Lo also took the class with me. More on him later. I loved the class so much, I became a paid teaching assistant the next two years when it was offered, essentially re-taking it twice. J-Lo and I built Carleton’s first green roof with full funding and support from Richard Strong and I was seriously pondering a career in green roofing. Fast forward to 2015 when I was mowing the lawn, listening to podcasts and I stumbled on the real estate podcast Bigger Pockets and realized that this was one area where a fellow could, through study, hard work and grit, turn nothing into something. The problem is that lots of real estate types are Presidential-level douchbags and landlords vie with used car salesmen for worst reputed profession. I suddenly realized that I could justify becoming a real estate investor and landlord to myself by making a lot of buildings more sustainable.

I had already insulated my house and popped on solar panels (back pat back pat), but that’s just one house. Not exactly saving mother earth. I had decommissioned my own oil furnace and replaced it with heat pumps (back pat) but again, small personal changes won’t change societal problems. But what if I could both start making extra money for my unborn daughter AND decommission other people’s fossil fuel systems…? It was on. I started devouring real estate books and podcasts for 2-3 hours every day. I met local investors, I talked to realtors, and in late 2016, I partnered with family to buy a single family investment property.

That was a massive learning experience and led me to buy a 3-unit property just a 7 minute walk down the street from the office where I worked. This was a delicious little secret. I could walk or bike over to my building to check on it during lunch. With both properties I dove into renovations, hiring contractors and learning how to do (and not do) all kinds of things like remodel a kitchen. Feeling empowered and energized, I reached out further and in 2018, bought three buildings totaling 26 units with family/friend investors providing the capital and me providing the research, acquisition and asset management. By this time I had hired 3rd-party property management because while I could easily manage a few units myself remotely and hold down full time jobs as dad and employee, 30 units was a non-starter.

In early 2019 I organized a larger group investment in a 10-unit mixed use commercial building in downtown Brunswick and also invested in a 6-unit building in Lewiston with my brother. I’m under contract on a building abutting my original 3-unit so the total now of units I co-own is 50. While this may sound impressive, I’m a minority owner of most of these and the passive income is not enough for me to hang up my boxing gloves and retire anytime soon.

Which leads me to the other two activities I’ll be diving into. The buyer’s agent I worked with for the past few years Don Spann had encouraged me to get my broker’s license, which I did in January so I’ll be helping other people invest in, sell and lease commercial real estate throughout Maine. When my best friend Brian Sprague from graduate school was looking for work and my 3rd property management company was under-performing, I knew that the best way forward was to found my own company- so together we’ve created Katahdin Property Management. Right now we’re learning new software and making all the beginner mistakes on my buildings, but soon we’ll put out our shingle and market to other owners.

We recently helped settle several Rwandan families that were housed in overflowing Portland homeless shelters and the Bowdoin student newspaper ran this story on my very last day on the job. My wife Rommy also works at Bowdoin and my two toddlers attend the Bowdoin Children’s Center, hence the photo for this post showing my old staff ID on the left and my new Spouse Gym ID on the right. I am extremely thankful for the opportunity real estate has given me to make people’s lives and neighborhoods better places and I’m excited to see what’s possible.

Posted on August 31, 2019 .