Can you share more about BOSS and what prompted you to make the decision to lead this syndicate? Last year, you joined Accomplice to be the Managing Director of their BOSS Syndicate.
I’ve made over 20 personal angel investments. Can you talk about some of the angel investments that you have made? Since moving on from FlipKey, you have been a very active angel investor. TripAdvisor proved to be a wonderful partner and we collaboratively made a significant impact on the industry, literally inventing the standard for vacation rental reviews and establishing our network as one of the big three (HomeAway, ABNB, FlipKey/Trip).ħ. TripAdvisor calls and says, “We noticed your tagline is ‘TripAdvisor of vacation rentals.’ What happens to that when we enter the market and we are, naturally, the TripAdvisor of vacation rentals?” Then the founder of AvantGo launches a similar play (PickPackGo) with a few million in funding. How did you raise seed money from TripAdvisor? What was the thought process of raising money from a strategic investor versus angel investors or a VC firm? We were one and a half years ahead of Airbnb but couldn’t get the primary home rental concept funded, so we pivoted the platform to the existing marketplace of second homes, AKA vacation rentals.Ħ. I did the math: mortgage bill / nights slept in my own bed = $300/night. I just bought my first place in the North End and received my first mortgage bill. What led you to move on and start FlipKey? That was our big direct-to-consumer play, which proved to be a major catalyst and gave me the confidence to strike out on my own.ĥ. I helped build out our client services team with Stephen, then founded a wireless vertical practice with Ryan Burke (at InVision) and then created with David Cancel (at Drift). Can you share some of the details around your contributions at Compete in terms of helping them scale and grow? Lesson: 80 percent of success is showing up.Ĥ. He explained, “There were other people I could have hired, but I remember you kept showing up at ZEFER.” Stephen later became CMO of Compete (he’s now President) and offered me a 90-day contract. Each meeting fewer and fewer people showed up. We had a team of 10-plus people working on it, but morale was low. We had a huge proposal into the city of Boston. All project work turned into "pitch work". ZEFER was an amazing experience but it was dying. How did you get connected with the team there? After spending a few years in the consulting industry, you ended up joining Compete in the early days. After a year, I pulled the plug and moved to Boston to join ZEFER.ģ. I was a terrible coder, Dallas is the worst, and never being home was soul draining. I worked in Dallas Monday through Friday and then flew back to Minneapolis. I learned HTML, Javascript, and even a little Perl script. I had a feeling the internet was going to be a big deal and forced my way into their first “e-now” training. I joined Accenture, which was called Andersen Consulting back then. What did you do for work right out of college? I played ball for four years, DJed at the college radio station TA’ed intro econ classes, chaired a student board, interned, drank, and pretty much crushed the college experience.Ģ. The high school years, including TJ's 1980 Pontiac 6000 LE nicknamed "The Yak" Interesting note: many consider Harvard the Macalester of the East coast. Macalester, a non-scholarship school, offered to push me through admissions, so off to the northern tundra of the Twin Cities I went.
I made the All State team and for a brief moment I thought I could get an athletic scholarship - but I didn’t because, frankly, I wasn’t good enough. I grew up playing every sport that was offered, but always favored basketball. I have two large families that, when combined, look like the United Nations. Where did you grow up? What prompted you to attend Macalester College and study economics and history? Since its launch, BOSS Syndicates has created Boston's largest and most active seed fund, investing in over 40 companies.ġ. The syndicate includes a network of 50 pre-approved leads (either successful founders or executives) who are scouting out companies and ultimately create a community approach to investing. Last June, he took on a role as Managing Director of BOSS Syndicates, which is an AngelList syndicate started by Accomplice to amplify early stage investing in Boston startups. TJ Mahony is an accomplished entrepreneur and an active angel investor in Boston.