New Boston angel investors: A crowd of them watched pitches at Wistia HQ for a NextGen Angels event earlier this month (photo courtesy Chris Keller).

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There was a time when to be an angel investor in Boston meant you made your money on Route 128 in the 90s and poured it out in medium-sized checks chased with advice. There are many from that era who are still active. I’m calling them the first generation of Boston angels, and while some don’t fit my sweeping generalization, they represent a cohort of their own.

Then, in about 2009, times changed. Paul Graham slammed the door on Cambridge, Techstars arrived and a new generation of angel investors started to emerge. Unlike many of the first generation, these people weren’t retired; they were running their own startups–probably a second or third company after one or two successful exits–and making angel investments on the side.

Dharmesh Shah

HubSpot’s Dharmesh Shah was among the first, and probably the most prolific, at that time. He’s made about 64 investments, by his own count. “When I got into angel investing, it wasn’t to make a ‘return,'” he told me in an email. “I was still a graduate student at MIT at the time, and angel investing seemed like a way to connect to the Boston startup ecosystem and meet some smart entrepreneurs.”

Jennifer Lum started writing checks in 2010. She said events pushing for more angel investment helped her get started–specifically, Angel Boot Camp organized by Jon Pierce in Boston and Open Angel Forum, organized by Jason Calacanis here and in Los Angeles. “I remember leaving the events feeling motivated to start making small investments,” she told me.

Now, it’s a new generation of angels having a similar experience. I started thinking about it last week after hearing Streetwise co-founder Chase Garbarino talk about his experience raising funds for Ventureapp. Their list of investors includes a handful of this new generation.

Jennifer Lum

The new angels have heavier wind at their backs than Lum et al. did in 2010. There are AngelList syndicates. I count FlipKey founder TJ Mahony among this latest generation and he’s working on the BOSS syndicate on behalf of Accomplice. In one month, he told me he’s worked on about six deals there. So that’s heating up.

Second is the increase in seed-stage funding from institutions. With a seed-focused fund in a deal, it’s easier for a startup to spend time with $5K investors who are good advisors.

For the new generation of Boston angel investors, $5,000 to $25,000 is about what they’re putting into deals, said Chris Keller, a HubSpot Labs veteran who’s been leading the launch of NextGen Angels in Boston.

“Time is the number one factor,” in the rise of a new generation of angels, Keller told me in an email. “Startups have been hot since 2007, successes have happened.”

Chris Keller

Is the syndicate killing the angel groups of old? No, wrote Keller from his position running a local angel group. “Syndicates are definitely a smart way to scale, but are frequently impersonal aside from the person leading the investment,” he wrote. “Many times this will be OK, but it will always leave room for angel groups in which the entrepreneur wants to meet people in person and or have more of a connection with their investors.”

Keller, of course, runs an angel group. But he may be right. Hub Angels, one of Boston’s oldest groups, is nearing a close on a new fund. As if you didn’t already know that from reading the BostInno Beat.

“There’s some growth and there’s a lot of turnover,” Jean Hammond told me over the phone. She ran Golden Seeds and has co-invested with some of Boston’s other longest-running angel groups.

With that, here’s my stab at a list of the three generations of angel investors active in Boston today. I’m sure I’m missing some and miscategorized others. Let me know in the comments or get at me on Twitter.

First generation Boston angels
Joe Caruso
John Landry
Jean Hammond
Jill Preotle
Ed Roberts
Peter Aldrich
Bill Warner
Andy Payne
Cheng Wu
Bill Sahlman
Shikhar Ghosh

2nd generation Boston angels
Dharmesh Shah
Brian Shin
Jennifer Lum
Nicole Stata
Eric Paley
David Chang
Ty Danco
Lars Albright
Maia Heymann
Dave Balter
David Cancel
Roy Rodenstein
Reed Sturtevant
Katie Rae
Walt Doyle
Mike Baker
Jere Doyle
Sarah Fay
Hugh Crean
Semyon Dukach
Andy Palmer
Shereen Shermak

New generation Boston angels
Sarah Hodges (
Fred Shilmover (InsightSquared)
Brent Grinna (EverTrue)
Phil Beauregard (Objective Logistics)
Jordan Fliegel (CoachUp)
Jeremy Levine (StarStreet)
Chase Garbarino (Streetwise Media)
TJ Mahony (FlipKey)
Chris Jacobs (Honest Discounts)
Wayne Chang (Crashlytics)
Paul English (Kayak)
Diane Hessan (Communispace)
Jason Robins (DraftKings)
Mike Salguero (CustomMade)
Patrick Petitti (HourlyNerd)
Dan Preston (AisleBuyer)
TJ Parker (Pillpack)
Tony Longo (co.everywhere)
Elias Torres (Performable)
Chris Savage (Wistia)
Josh Schanker (Bookbub)
Jeremy Hitchcock (Dyn)
Kyle York (Dyn)
Matthew Ryan Grace (Objective Logistics)
Andrew Paradise (Skillz)
Julia Austin (VMware)
Nick Ducoff (Boundless)
Jay Batson (Acquia)
Corey Thomas (Rapid7)