A real angel among angel investors

Angel investor Joe Caruso at the Cambridge Innovation Center.
Angel investor Joe Caruso at the Cambridge Innovation Center.

Getting an audience with Joe Caruso doesn’t require sweet-talking an assistant or networking your way through friends of friends of friends. You simply go to a scheduling website and sign up for a half-hour block of time, and a few days later, you enter a small glass-walled conference room at the Cambridge Innovation Center and sit down across the table.

Caruso is tieless in a blue Oxford, laptop open in front of him. His vibe is Peter Falk-like, more listener than know-it-all. “Tell me about yourself – not your business,” is a typical opener.

When I signed up for a slot earlier this month, though, Caruso spent the first few minutes trying hard to convince me not to write a column about him. His reasoning: Lots of people offer advice and mentorship to entrepreneurs in Boston, and a sizable subset of that group write early checks to fund businesses they feel have a shot at success.

But no one else is as accessible, humble, and willing to help as Caruso, who calls his Westwood company Bantam Group. And it’s hard to find an angel investor in Boston with as diverse of a set of investments. Caruso put money into HubSpot, Constant Contact, and Carbonite, all now publicly traded software companies. He also invested in Coffee Connection, the early chain of cafes that invented the Frappuccino – and which was acquired by Starbucks in 1994; Sutro, which is designing a monitoring and chemical-dispensing system for pools; and Terrafugia, a Woburn company developing a flying car.

“Joe is an investor in people,” says Matt Douglas, chief executive of Punchbowl, a party invitation site based in Framingham. “I still don’t think he really understands Punchbowl, but the product and the specifics of the technology are not that important to him.”

Caruso says, “I pride myself in having a good filter for people. It hurts when I’m wrong. It’s like you’re the expert at selecting wines, and it turns out you paid $1,000 for a bottle of vinegar.”

Caruso meets with all sorts of entrepreneurs at office hours: “Fifteen-year-olds, 65-year olds, some people with brilliant ideas, and some complete whack jobs,” he says. But even when someone is describing the small snafu keeping the perpetual motion machine from working as designed, Caruso says, “I throw a switch and treat them like an absolute equal.”

Caruso has never actually started his own company. He was an early employee of Teradyne in the late 1960s, which was just starting to make test equipment for the microchip industry. He later ran a company that made monitoring systems for stroke and spinal cord patients, Cyborg Corp. It was a bruising experience, with the company’s investors at one point suing each other.

Back then, he says, “I didn’t have the benefit of a good mentor, and I’d like others to have it. It’s sort of my mission.”

He’s omnipresent at startup showcases and business plan competitions. He seems to know about almost every company in an initial fund-raising round; sometimes, he writes the first check that doesn’t come from the founder’s friends or family.

Seth Priebatsch, founder of the Boston mobile payment company LevelUp, says he pitched Caruso one morning before running the Boston Marathon in 2009. “He wrote me a $5,000 check then and there, and I put it in my sock and ran back to Boston with it,” says Priebatsch, who was at the time a Princeton undergrad.

Recently, some of Caruso’s companies have been acquired by Google, VMWare, and Autodesk. One startup, Crashlytics, which helped mobile app developers collect data about crashes, was acquired by Twitter within a year. That turned his $5,000 into more than $200,000, according to Crashlytics founder Wayne Chang. But Caruso’s Bantam Group website doesn’t conceal the companies that croaked, designating them with a skull-and-crossbones icon.

Caruso meets with Jessica Angell, founder of Cabbage Company, at the Cambridge Innovation Center.
Caruso meets with Jessica Angell, founder of Cabbage Company, at the Cambridge Innovation Center.

“Anybody who says they can predict a company is going to be successful is lying,” says Caruso.

Investing in fledgling businesses can feel like rolling dice, but Caruso believes a good investor can be like “a little speck of dust on the die that biases the way it lands. It can be advice, it can be introductions. I make my little contribution, and some other people make theirs, and we bias things in the direction of success.”

In 2000, “I was a first-time entrepreneur, and Constant Contact was my first time raising venture money,” says Gail Goodman, chief executive of the Waltham digital marketing company. “Joe was everything I needed — he helped me tune the [slide] deck and tune the pitch. He was that perfect coach.” Constant Contact today employs more than 1,400 people.

The money may not be a “life-changing” amount, says entrepreneur Ben Sprecher — typically it isn’t more than $25,000 — but Caruso’s name can help in persuading other investors to hop on the train.

“He has a ‘how can I help?’ attitude, as opposed to a ‘how can I make money?’ attitude,” says Sprecher, whose couponing startup, Incentive Targeting, was acquired by Google in 2012.

Caruso says his typical Thursday at the Cambridge Innovation Center starts at 10 a.m. and runs through 6 p.m. He holds similar office hours at his alma mater, Northeastern University, as well as MassChallenge, Techstars, Harvard, and the WeWork shared office space. According to his calendar, he has met with more than 250 entrepreneurs in 2015 so far.

When my half hour with Caruso was up, I noticed a group of people lingering outside the conference room — three entrepreneurs from Spain. It was their turn for 30 minutes with Joe. Maybe it would be just another meeting. But maybe it would be the one that altered the roll of the die.

Scott Kirsner writes the Innovation Economy column every Sunday in the Boston Globe, in which he tracks entrepreneurship, investment, and big company activities around New England.
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