April 11, 2016
[Investor Q&A] TJ Mahony of Accomplice / BOSS Syndicate - Impact Investing In Boston

TJ Mahony is an accomplished entrepreneur and an active angel investor in Boston. 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. 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. Since its launch, BOSS Syndicates has created Boston's largest and most active seed fund, investing in over 40 companies.

1.  Tell us about your background. Where did you grow up? What prompted you to attend Macalester College and study economics and history?

I’m from Boulder, Colorado. I have two large families that, when combined, look like the United Nations. I grew up playing every sport that was offered, but always favored basketball. 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. Macalester, a non-scholarship school, offered to push me through admissions, so off to the northern tundra of the Twin Cities I went. Interesting note: many consider Harvard the Macalester of the East coast.  

TJ Mahony High School
The high school years, including TJ's 1980 Pontiac 6000 LE nicknamed "The Yak"

I loved Mac. I played ball for four years, DJed at the college radio station (@DJTJ), TA’ed intro econ classes, chaired a student board, interned, drank, and pretty much crushed the college experience.

2.  What did you do for work right out of college?

I joined Accenture, which was called Andersen Consulting back then. I had a feeling the internet was going to be a big deal and forced my way into their first “e-now” training. I learned HTML, Javascript, and even a little Perl script. My first project was in Dallas, Texas. I worked in Dallas Monday through Friday and then flew back to Minneapolis. It sucked. I was a terrible coder, Dallas is the worst, and never being home was soul draining. After a year, I pulled the plug and moved to Boston to join ZEFER.

3.  After spending a few years in the consulting industry, you ended up joining Compete in the early days. How did you get connected with the team there?

ZEFER was an amazing experience but it was dying. All project work turned into "pitch work". We had a huge proposal into the city of Boston. We had a team of 10-plus people working on it, but morale was low. Each meeting fewer and fewer people showed up. But I kept at it. The deal’s lead was Stephen DiMarco. Stephen later became CMO of Compete (he’s now President) and offered me a 90-day contract. He explained, “There were other people I could have hired, but I remember you kept showing up at ZEFER.”

Lesson:  80 percent of success is showing up.

4.  Can you share some of the details around your contributions at Compete in terms of helping them scale and grow?

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). 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.  

5.  What led you to move on and start FlipKey?  

I was traveling quite a bit promoting I just bought my first place in the North End and received my first mortgage bill. I did the math: mortgage bill / nights slept in my own bed = $300/night. Damn! I should just live in a hotel…. or turn my place into a hotel. 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.

6.  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?

HomeAway raises $500M. Then Airbnb shows up. Then the founder of AvantGo launches a similar play (PickPackGo) with a few million in funding. 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?”

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).

7.  Since moving on from FlipKey, you have been a very active angel investor. Can you talk about some of the angel investments that you have made?

I’ve made over 20 personal angel investments. You can see my action here:

8.  Last year, you joined Accomplice to be the Managing Director of their BOSS Syndicate. Can you share more about BOSS and what prompted you to make the decision to lead this syndicate?

I joined Accomplice to lead BOSS because I felt it could fundamentally lift the tide of impact entrepreneurship in Boston.   

Let me expand. Per your last question, I’ve made 20-plus personal investments, the vast majority being HQed in Boston. Why?

  1. I believe in the company and expect to make a return.

  2. I believe I was gifted the superpower of luck, timing, and a pinch of smarts to actually build and sell a company. I’m bound by cosmic law to extend and empower worthy entrepreneurs at a similar shot.

BOSS amplifies this ethos across Boston in a manner no individual nor single venture firm could on their own.  

This is a solid Medium post that further explains and expands.

9.  What are the top traits you look for in terms of investing in a company and/or founder?

Company: I tend to like interesting ideas in boring markets (air filters, greeting cards, muni bonds, window replacements, etc)

Great founders: There is an authenticity to their mission and commitment to succeed. It’s tough to define, but you know it when you see it.

10.  Are there specific areas of technology, industries, or trends which are a focus for BOSS?

BOSS focuses on amazing people - not specific verticals or categories. This federated approach produces a spectrum of coverage:  IoT, mircroservices, paper, beacons, marketing automation, QSRs, wearables, consumer health, influencer marketing, bicycles, fintech, art… you get the point.

11.  How many companies has BOSS invested in since last June?  

In total, we have backed 40 companies since January 2014. Since June, we’ve backed 16. Easiest way to keep up with us is to follow us on AngelList. You can also find additional info at

12.  What are some of the companies that our readers might recognize?

You can check out the portfolio here:  BOSS Portfolio

13.  Which companies outside of the BOSS portfolio in the Boston area do you find interesting?

I really like the guys at HourlyNerd and Placester. I also wish I got into Sweetgreens, despite never having eaten there. The lines are always too long.

14.  Who do you admire or who has been the greatest mentor for you?

Ferris Bueller. That guy was a force of nature.

15.  Outside of being an investor, what are your personal interests or activities?

I used to be an interesting guy, but then I had kids.

TJ Mahony and kids
TJ with his children

16.  What type of music do you like?  

90’s hiphop is where I flourish. If there was a national Jeopardy competition on Rap Music in the 90’s, I’d give myself 3:1 odds of winning.

17.  Are you involved in any charitable organizations?  

I am… I wish I was more involved.  

Currently: ICW (Inner City Weightlifting), BUILD, TUGG, and I’m very involved in initiatives at Macalester.


TJ and his wife, Jess, rafting in Colorado


Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.