Startup Grind
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Startup Grind

33 Boston-Area CEOs & Their Differences

Here’s a secret: every great CEO I know is fucking weird.

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.

What you see in the eyes of Runkeeper CEO, Jason Jacobs

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?

Young Guns, featuring Nick Rellas and Matt Barba

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.

Ralph Folz, CEO of Wordstream

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.

Jeff Glass, the voice behind Crow T. Robot

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.

Ben Carcio, Promoboxx

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.

Boston’s latest startup CEO: GE’s Jeff Immelt?

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

Herbivorous, crepuscular
Cuddly, but muscular

Vishal Sunak, LinkSquares

Chase Garbarino , VentureApp

Kind of like Paul Newman in the Hustler. Does that make Greg Gomer Jackie Gleason?

Chase and Gomer, Always Hustlin’



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