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@BostonTweet Looks Back: “If I never tried, my life would be totally different now.”

By Katherine Isbell Nov. 12, 2017

When Tom O’Keefe opened a Twitter account in 2008, he never imagined it

would lead to him riding in the Hood blimp over the city, being recognized on the street,

or sitting in a Duck Boat with Keytar Bear, a well-known street performer who plays his

keytar while wearing a teddy bear costume.

But somehow, beyond his wildest

expectations, it did.

The Twitter account,

@BostonTweet, now has nearly 275,000

followers and is verified on the social media

platform. BostonTweet also has a website

and is present on most major social media

networks, including Facebook, Instagram,

and Snapchat. Nine years later, the Twitter

account has also helped him to find success in his other business ventures.

O’Keefe, a New York State native who grew up near Poughkeepsie and graduated

from Boston College in 1995 with a degree in economics and politics, worked in finance

at firms like Fidelity and Thomson Financial after college until the early 2000s, when he

had a realization. “I was like, ‘This is not for me.’”

That revelation led to O’Keefe to turn launch various Internet start-ups, but after

the stock market crash of 2008, O’Keefe’s start-ups became “basically worthless

O’Keefe at Caffè Nero in Brookline on Oct. 30, 2017

Image: Katherine Isbell

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overnight,” and he was “desperate for anything,” which, in November 2008, led him to

join Twitter, which was only about two years old at the time.

O’Keefe figured that, perhaps, Twitter could help him to find employment, and

maybe he could promote some local businesses along the way to help them to stay afloat

during the recession. “I started looking for a job, and I couldn’t get a job. No one knew

who the hell I was,” O’Keefe said while sitting in Brookline’s Caffè Nero on a Monday

morning, “Part of it was to promote myself and to get a job hopefully by the time January

starts. By promoting local business, it was directly promoting me. … But by January it

became so popular, and it became my job. I was not expecting that whatsoever.”

BostonTweet still promotes local businesses, but the account also updates its

followers on current events in the area. This means that O’Keefe’s schedule is never the

same week-to-week, and he could be doing any number of things, from meeting a

member of the local government or watching a Red Sox game from the front row at

Fenway Park to volunteering for a local charity or hiding giveaways, which he posts

about on social media to invite his followers to find, around the city. “It’s different, but a

lot of it is meeting people, which is really fun,” O’Keefe said, “There’s never been a

typical week.”

In 2015, O’Keefe co-founded Flutter with Steve Callan, his friend and business

partner of almost 10 years. Flutter is an online company that offers participants the

chance to enter raffles for experiences, like front-row seats at a Celtics game or 100 free

burritos from a local restaurant, when they donate $10 to any one of over 90 local

charities.

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Callan said that they both work on the brand and platform direction, as well as the

marketing for Flutter, and he handles the technology side of the company, while O’Keefe

“handles sourcing, relationships and the connection to his @BostonTweet account.”

The inspiration for Flutter came from the frustration O’Keefe experienced when

he was attending a charity event for Big Brother, Big Sister in February 2015, and he

couldn’t contribute anything to the charity auction because the bids being made were

upwards of $10,000. “I’m like, ‘I could do 10 [dollars],’” he said, “I left the place, I

didn’t donate anything because there wasn’t the opportunity for a smaller person, a small

pocket guy like myself to donate, and I was like ‘I feel like such an a**hole,’ [because] I

didn’t give anything.”

Taking inspiration from other ventures like CrowdRise, which use “huge

celebrities,” O’Keefe and Callan decided to “tweak it to just [be] locally-based and for

local charities and $10.”

“It came about to get millennials involved in charity… to make it easier entry and

make it something exciting for them.” O’Keefe estimates that Flutter now has raised over

$105,000 from over 7,000 participants, however, he and Callan make no money off of it.

Callan credits BostonTweet with helping to set the stage for Flutter’s success.

“More than just audience visibility, I don’t think Flutter could have ever been successful

without the support of @BostonTweet. @BostonTweet has given us reach,” he

explained, “Also, we live in a time where there are so many questionable online digital

services, and we’re asking customers to trust us with their donations to local non-profits.

Tom’s @BostonTweet has developed such strong brand loyalty and trust among

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Bostonians, that association has allowed us to connect with people in a way that I don’t

think would have been possible otherwise.”

Last month, O’Keefe began working with Boloco in an effort to incorporate some

of what Flutter does into the burrito chain. He had been a friend of the business, and

particularly friends with one of the co-founders, John Pepper, since joining Twitter in

2008 and connecting on the social media platform.

In addition to hiding giveaways from the burrito chain around the city, O’Keefe

explained his job with Boloco is “to head up their social impact mission and department.”

Describing the goal of the partnership, he said, “Basically it’s just trying to get them

more involved with the community, more involved with charity… more working with

local companies or start-ups.”

While O’Keefe has partnered with companies, such as Groupon and Fasten,

before as a way to help introduce them to the area, his partnership with Boloco is a new

experience for him. “Working with Boloco was the first time I’ve actually signed on,

somewhat, with a company full-time. … I have worked with a ton of companies over the

years, but the foundation has always been that it’s all about BostonTweet.”

The one downside to what O’Keefe does is, perhaps, what his mother thinks of it.

“My mom thinks I’m unemployed, and she tells people I don’t have a job,” He laughed,

“She doesn’t really know how to get online. ... It’s not a ‘real job,’ it’s not like I’m a

lawyer or a doctor or go to an office or a finance job.”

A life without BostonTweet is not something that O’Keefe has had to imagine. “I

probably would’ve been at one of those jobs [in finance], I guess… who knows? Which

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probably would have made a lot more money for me over the years, but I probably would

have been very sedentary, and I’ve gotten a lot more active since doing BostonTweet.”

If he could do anything differently, O’Keefe would have started Flutter earlier.

“By 2015, people’s attentions were now focused on Instagram or Snapchat, [along with]

Twitter and Facebook… so I think if I started Flutter around 2010, 2011, or 2012, then I

could’ve raised a lot more money for charity from that platform [when people’s attention

was focused mostly on just Twitter and Facebook],” he explained, “Even though I have a

lot more followers now, I think I had much more people paying attention back then.”

However, O’Keefe would not have done anything different in terms of how he

started BostonTweet, saying, “It was really perfect timing.”

He suggests that anyone looking to become an “influencer” online look for a way

to make what they do somehow connected to their community. “Stuff that seems to really

promote communities seems to really resonate with a larger audience… With

BostonTweet if I started off talking about Tom O’Keefe, they could care less about me,

but when it was focused on Boston, it made total sense and certainly did much better.”

O’Keefe’s biggest advice for college students looking to find success in the social

media world is simple, “You just gotta do it and put it out there. Just create something

and see what happens,” he said, “If I never tried, my life would be totally different now.”

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