33 Boston-Area CEOs & Their Differences
Here’s a secret: every great CEO I know is fucking weird.
Ok, that may be harsh. Maybe weird isn’t the right word. Maybe it’s quirky. Or unique. Or… different. Different.
Yeah, that’s probably more like it.
Being “different” means that most CEOs act as if they’re living in some alternative reality; a reality where their behavior creates a natural distortion field.
But if harnessed right, this behavior — this distortion field— it’s magnetic. It’s what enables a CEO to harness brilliant minds to follow them into battle, to enrapture venture capitalists into funding their ideas, and to create mountains out of molehills.
With that in mind, here’s my running list of some of Boston’s finest startup CEOs — and what makes each of them just a little bit…different.
Fred Shilmover, InsightSquared
He makes smart look stupid, and is a Julian Edelman fan-boy. And may be a robot.
Brian Halligan, HubSpot
Funny, transparent, self-deprecating and ridiculously effective at the Irish Goodbye, the French Exit and Ghosting.
(plus: boogies down hard to any scarlet->fire)
Katie Rae, The Engine
The Mama Bear of Boston Tech: “can be cuddly and lovable but also has a ferocious side when it’s necessary to protect her cubs.”
Ben Rubin, 10% Happier
I’d definitely drop acid with him.
Seth Priebatsch, LevelUp
At one point Seth publicly noted friends were “caustic” “ephemeral” and “utilitarian”. Clearly a genius, time will tell if he’s he’s Howard Hughes or Albert Einstein.
Niraj Shah, Wayfair
Well-liked by just about everyone; he appears unfazed by just about everything. He’s a regular guy, who may be regular. But I really don’t know about that.
Brent Grinna, EverTrue
He’ll tell tales of baling hay in Iowa, with a soft-spoken “aww shucks” attitude. But it’s a schtick. He. Is. Not. A. Hick. Unless hicks go to Brown and HBS.
Bonus: he’s Gronk-ingly barrel-chested and dashingly good looking.
Jason Jacobs, RunKeeper
His 1000-yard stare will scare the bejeezus out of you. I swear I’ve seen Tweety Bird in his eyes.
David Cancel, Drift
Mysteriously cryptic and yet mind-numbingly straight forward. I’m 98% sure he hypnotized me once over lunch.
Art Papas, BullHorn
Apparently, 80% of Americans fall short of the 3-to-1 positivity ratio. Not Art. He’s constantly pinching himself about how fortunate he is. The guy is a walking double rainbow.
Nick Rellas, Drizly
Lou Diamond Philips (‘Jose’ Chavez y Chavez) in Young Guns. Possibly during the Peyote ritual. No, now you stop it. Just because he runs a booze-company doesn’t mean he’s Charlie Sheen.
Matt Barba, Placester
Young Guns II. Emilio Estevez. Probably wants to be Kiefer Sutherland, but who doesn’t?
Grant Deken, Grapevine
He’s now hella good at “Ganbei!” with Maotai (post nailing an investment from Chinese Billionaire Bruno Wu). Witty and relentless, his moral compass is so strong it’ll pull the change out of your pocket.
Ira Hernowitz, Kindara
A veteran of Hasbro and Stride Rite, he’s new to the startup scene, so is in constant tofu mode. Bald and no BS, he’s sharp as a tack and gives good meetings.
Ralph Folz, Wordstream
Calm, collected and matter-of-factly fierce. Got a problem, he’ll fix it. Just like Mr. Wolf.
Jeff Glass, Starting Five
A conversation with Jeff requires you to yank up your witty banter trunks. Word on the street is he’s been spotted doing audio voiceovers for Crow T. Robot from MST 3000.
Nick Francis, Help Scout
His hair is banging. No really it bangs. It may fuck, I don’t know. Charming and introverted, his talent-recruiting acumen is matched only by his capacity to unemotionally punt under performers and culture clashers.
Phil Beauregard, Stealth
Social is the sword he slices with swagger. I’m guessing it’s the same sword that cut off his man bun.
Janet Comenos, Spotted
She’ll crush you in sales. She’ll crush you in tennis. She’ll crush the piano. (and she’ll probably crush the crush you have on her). If she’s not first, best or winning, she’s not playing.
Rob May, Talla
I’m confident he is confident.
Greg Segall, Alyce
The guy is so intense he makes double-the-caffeine High Voltage Bones coffee seem timid.
Nicole Stata, Boston Seed
The hostess with the mostest, and damn good with a martini. She wields her unmatched generosity with incredible finesse.
Ben Carcio, Promoboxx
Bluffs hard, has serious poker face. Plays chicken like Kevin Bacon in Footloose.
Jason Robins, DraftKings
Spend 30 minutes with Robins and you‘ll swear he’s generated a thousand-row excel file on you, with calculations like TRIM(UPPER(MID(A1,3,2))).
Paul English, Lola
They say there are 114 spiritual power chakras in the human body. English’s bold freneticism — he’s practically dripping electricity — proves there’s a 115th.
TJ Parker, PillPack
So understated it’s disarming. Ok, so he looks a little bit like Ed Sheeran, so how would you feel, if the shape of you…saw the fire…on the castle on the hill?
Ric Calvillo, Nanigans
It’s never a question of where you stand — it’s his way or the highway. An incredibly talented, incredibly direct One Man Army.
Polina Raygorodskaya, Wanderu
Direct, different and indifferent. Apparently Wanderu is Russian for Wanderu.
Jeff Immelt , GE
Word is he likes to get in costume to “meet the people.” Supposedly he’s been sighted wearing Adam Duritz dreadlocks on the corner in front of Lucky’s.
Ariel Diaz, Blissfully
Excuse me, sir, your collar is sticking out of your shirt. What? <awkward pause, subtle stammer> No, really, your collar is sticking out of your shirt. Oh, you were serious. Ok.
Rochelle Nemrow, FamilyID
Funny, disarming and tenacious. I check my wallet every time she passes me in a crowded bar.
Vishal Sunak, LinkSquares
Cuddly, but muscular
Chase Garbarino , VentureApp
Kind of like Paul Newman in the Hustler. Does that make Greg Gomer Jackie Gleason?
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