Image of Phil Beauregard at New Hampshire's Jackson Falls (courtesy via Instagram)
Image of Phil Beauregard at New Hampshire's Jackson Falls (courtesy via Instagram)

HBO’s new show Silicon Valley, which parodies the sometimes ridiculous happenings in Northern California’s robust tech ecosystem, has a cast of main characters that typify the common archetypes of those involved in the world of startups.

There’s Erlich Bachman, the hard-partying former founder who runs a home for entrepreneurs to live and work in exchange for company equity. Bachman is pretty much an amalgamation of individuals like Sean Parker and accelerators like 500 Startups and Techstars.

Richard Hendriks, the main character who unknowingly built the world’s greatest compression algorithm into his music sharing product Pied Piper, has all the quirkiness and aloofness of the Mark Zuckerbergs of the world. Almost every character is based on a mashup of the zany, ego-driven, bright, and sometimes disconnected-with-reality figures that fill the offices and coffee shops of not only San Francisco, but any major tech hub, Boston included.

What there isn’t is a Phil Beauregard type in HBO’s startup hit. Beauregard, the cofounder and chief executive of Objective Logistics and also the soon to be released Rekindle app, defies the conventions of what a tech startup founder looks and acts like.

Not your average CEO

Beauregard seems very at home in the dark corner of a Downtown Crossing bar, vodka on the rocks in hand, where we sat down to talk about running a startup, mentoring young entrepreneurs, and championing locally important causes.

More than anything, he is a local, carrying about him the same grit and saltiness that Herman Melville captured in his descriptions of Beauregard’s hometown of New Bedford in the opening pages of Moby Dick. When I asked him what is was like growing up in New Bedford, Beauregard said, “I grew up getting in fist fights, pissing my parents off, and working in the restaurant business,” which seems to be standard story for anyone who grew up on the South Shore and along the Massachusetts/Rhode Island border.

One experience that really stood out for Beauregard was the shock of moving from a private school with a class of 30 people to New Bedford High School with its more than 4,000 students. He said the second day he was there, he got beat up just because he bumped into someone who didn’t like the way he looked (Beauregard added that the assailant in currently incarcerated for murder).

Growing up, Beauregard knew two things: He was good at math and wanted to make money. Eventually, he found his way to The University of Pennsylvania’s prestigious Wharton School.

After stints in investment banking, working for Americorps, a short-lived career in the mall-based fashion world (“cough-cough”-Abercrombie), and almost every other industry under the sun, Beauregard fell back on the restaurant/service sector. Restaurants seemed like the perfect fit once Beauregard came up with an idea to disrupt an industry with smart data tracking and some gamification.

So Objective Logistics was born.

Disrupting the restaurant service industry

“We looked at restaurant employees as one of the largest sales forces in the world,” Beauregard explained. “[The industry] has so many different archetypes of people with so many different motivations, from a kid tying to make extra cash to a single mother.”

With Objective Logistics, Beauregard wanted to create a meritocracy in the workplace where everyone can excel so that the customer can have the best experience, as he explained it.

Beauregard worked out of coffee shops and his parents’ basement while building the company. A mutual friend connected him with his cofounder and chief technology officer, Matt Grace, who grew up in Dartmouth, Mass., and also happens to be a recent “Most Eligible Bachelor” in Boston. Beauregard was both impressed and blown away by Grace. “He was running optimization algorithms for Best Buy and Geek Squad at the time, and also just happened to be one of the youngest product directors ever at Oracle.”

Phil Beauregard, left, with cofounder Matt Grace

Phil Beauregard, left, with cofounder Matt Grace

Besides the intellectual bond, Grace and Beauregard had a lot more in common as Southern Mass. guys who didn’t quite fit the mold. As Beauregard said, “Matt was big pain for everyone growing up.”

Objective Logistics got a break when Scott Kirsner wrote an article about the company that ended up getting syndicated to a restaurant industry website/journal. After the piece, the startup was inundated with restaurants wanting to try its employee optimization product.

Next, Beauregard said that Atlas Venture’s Dustin Dolginow found Objective Logistics through AngelList, and they got their first funding with Atlas and Jeff Fagnan leading the investment. Beauregard said that Fagnan asked him who else they wanted to work with for the investment, and Google Ventures immediately came to mind. “We knew we wanted to work with Rich Miner,” he explained, “we were tremendously intellectually compatible.”

Mentoring and helping Boston in so many ways

Being the founder of an up-and-coming local startup has allowed Beauregard, whose mother did work in social welfare in New Bedford, to “pay it forward,” a phrase he probably would dislike being associated with.

At first, Beauregard got involved in mentoring other entrepreneurs at accelerators like Techstars. Although he still does a lot of mentoring, he sees an overflow of bad quality mentoring going on these days with the huge quantity of accelerators in Boston. “There are a lot of sycophants that may have had a successful company years ago or may be an associate at an accounting firm who call themselves mentors these days,” he said. “Half of what I do is unwind the bad advice of some of the awful mentors in town.”

Eventually, Beauregard started investing small amounts of money in some of the startups that he really liked. “I wanted to get more involved in the community and I thought investing was good way to do that,” he said. The companies that he is a disclosed investor in include StarStreet, Buyside F/X, Take the Interview, and The Tap Lab.

Beauregard is also involved in Technology Underwriting Greater Good and is a defender of the inexperienced entrepreneur. He was one of the main catalysts in forming the Unpitch event last year, to give startups a chance to meet with quality investors, as a response to what he described at the time as the “startup snake oil” of organizations like Young Startup Ventures.

Last year,  in the aftermath of the marathon bombings, Beauregard was one of the key figures along with Terrible Labs’ Jeremy Weiskotten who rallied the tech community together to raise money for the victims.

At first, Beauregard turned to Twitter to ask the community how best they could help out, even trying to start a blood drive.

“There were hundreds of people responding on Twitter and email, that we decided to start a fund, mobilizing all the support to make something positive out of the tragedy,” Beauregard said.

With the help of David Brown from TUGG and Jeff Fagnan from Atlas Venture, they set up a fundraising page that reached its initial goal of $10,000 in eight minutes. In the end, the effort raised about $350,000, which was split between the One Fund and specific charities helping those closest to the tragedy.

“It shows you the power of social media and the power of the Boston network to come together and rally behind a cause,” Beauregard said.

What’s Next

With the expected July launch of Beauregard’s latest venture, a reconnection app called Rekindle that has been described as a cross between dating app Tinder and anonymity app Secret, the Objective Logistics founder is adding more to his already full plate.

Rekindle is already generating a ton of buzz and has a list of impressive backers, including Google Ventures once again. Beauregard said there’s already interest from some major Silicon Valley investors looking to get involved in the project’s next round of funding. The main gist of the new app is to use an anonymous network to bring together friends and lovers who may regret a missed opportunity in the past.

Objective Logistics is continuing to grow as well. Word on the street is that the company is close to announcing some important restaurant industry partnerships. Additionally, the company has added Atlas Venture’s Chris Lynch to its board of directors and former Boloco chief executive John Pepper as an advisor.

With all the activity, Beauregard seems to be able to keep some level of sanity and stay true to his nature. “I think that authenticity is very important,” he said. “If you are not going to be yourself, you are not going to be respected. So many people act a part in this startup world.”

“All the world’s a stage,” he concluded quoting the start of Shakespeare’s famous lines from As You Like It.

As our conversation shifted from art history and the depth and richness of Cormac McCarthy’s writing, Beauregard got a message from a local startup founder whom he had mentored. As he read the text, his face lit up with unabashed joy. The founder was passing on some great news, and Beauregard, although not sharing with me who the message was from, was obviously excited for his fellow entrepreneur.

He quickly turned to the bartender, and announced, “Another round please.”

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