Taking flight

When Matt McEachern, CTO and Cofounder, was a kid he dreamt of the skies and becoming an Air Force pilot. “I thought planes were cool, and I liked the idea of the military. I figured being ejected from an aircraft would be better than ground combat because at least I would have my parachute. And I thought it would be more fun to fly,” Matt says. Perhaps the influence came from his family, with his grandfather and great grandfathers having served high-ranking military roles. Or perhaps it was growing up in sunny Rancho Peñasquitos, San Diego, California, which has a huge military presence and an Air Force base. 

In elementary school, Matt took his first steps into the entrepreneurial world. When he was young, Matt knew he wanted to start a business, even if he didn’t know exactly what that meant. An avid video gamer, Matt began to capitalize on Runescape, making real money in exchange for the virtual currency in the game. Matt also started a coral farm in high school. With $1,000, he purchased a saltwater tank and began purchasing and growing exotic coral. Ultimately, Matt broke even on this business venture, but fostered some cool clownfish in the process!

The youngest of three boys, Matt often looked to his older brothers for inspiration. “My second oldest brother switched from soccer to cross country in high school and fell in love with it. He would always tell me stories about how there’s nothing better than race day and leaving it all out there. I followed a similar path and switched from soccer to cross country in high school and it turns out everything he said about it was true,” said Matt. ”What he didn’t tell me was how much fun it was to go on long runs in the mud-covered trails, on the opportune days that it actually rained in San Diego.”

Growing up with two older brothers wasn’t all fun and games, however, even when playing games. “My brothers and I were really into collecting baseball and Pokemon cards. But they would always negotiate me out of my best cards with lopsided trades.” His brothers scamming him out of his best cards taught Matt a really valuable lesson - stick to your guns; you get in life what you negotiate! 

Crossing the finish line 

Math was Matt’s favorite subject in high school. So much so that by junior year he had run out of courses to take and attended the local community college his senior year.

“It was kind of nerve-wracking to be a senior in high school attending college courses. But the material was enthralling.”

It was also during his senior year that Matt was introduced to programming. “I knew that I loved coding when I realized that I was consistently staying up until 4am - without food, without caffeine - building and solving things.”

Although he mostly applied to colleges in California, Matt applied to MIT almost as an afterthought because someone had recommended it to him. 

The biggest uncertainty around attending MIT was the location and the “scariest aspect” was that he didn’t know anyone else going to Boston.  Fortunately, Matt was recruited to join the Cross Country and Track teams for MIT, which meant an immediate circle of peers with shared interests.  As was the case in high school, his distance running teammates were some of his closest friends and still are today.  “I’ve always been at the intersection of the athletes, and the nerds. So going to MIT with the opportunity to run felt right.”

Matt ultimately visited MIT twice before making the decision and taking a leap of faith by enrolling in MIT. This decision proved to be life changing. 

Meeting of the minds

Before freshman year officially began at MIT, Matt rushed a fraternity. In a cinematic-like montage, Matt met Karan Kashyap at the fraternity’s networking event. Matt remembers learning about Karan from that initial conversation. Karan started a nonprofit in high school and was in the process of starting a catering business, so they immediately bonded over their shared entrepreneurial spirit.

By sophomore year of college, Matt and Karan started talking about starting a software company together. Since they both studied computer science and Karan had a connection who offered them $25k to get things up and running, it seemed like the next inevitable step. Hysterically, they didn’t have an idea, nor did they desire to drop out of school.  But nonetheless, the seed was planted.  

They decided their business would be an “Application development and consulting” company.  And in January of 2016, mid-way through their junior year, they signed their first customer. 

“When we signed our first customer, it was a one month gig and we worked 60 hours a week. We were making $65 per hour, which blew our minds. It was so validating, exhausting, and really fun.” 

By the end of February, the excitement came crashing down when they realized they hadn’t been paid yet. After a lot of back and forth in chasing down the client, and the rollercoaster of emotions that came with that,  they finally got paid for their first consulting gig. They celebrated with a $10 bottle of prosecco. *Cue end of cinematic montage. 

Lab work

Karan was on a fast track at MIT and graduated in 3 years, going straight into a one year masters degree. During Matt’s senior year, and Karan’s masters’ year, they signed 5 contracts, including a few bot contracts. Two of these customers were publicly traded companies, and one of them totaled several hundred thousand dollars.

“Those early days of Posh with Karan can be characterized by reckless optimism. We didn’t think about how we were going to get everything done and we didn’t worry about figuring that out. We weren’t nervous and there was no sense of risk taking. Maybe we weren’t aware enough or maybe it was just our youthful energy. Either way, we simply let opportunity guide us and we went for it.”

Maybe it was fate, or maybe serendipity, but this same school year they ended up working in the SLS Lab led by one of the early gurus of speech recognition and human interaction. In working in this lab together, and signing those few bot contracts, the stars were aligned to fine-tune Posh as a Conversational AI company.

“We always knew that consulting was not something we wanted long term. Instead, we wanted to apply our knowledge as a product-focused company that would have outsized impact. Taking after what we learned from our consulting and school work, Conversational AI felt right. And customer service, specifically, felt like an obvious segment to tackle.”

And so the seed was planted for the Posh that exists today. That Posh unofficially started in August 2018 (and officially incorporated in 2019), with over $1 million in consulting revenue to jumpstart things.  

“As we were catching wind of the credit union market, we still had our options open for other verticals.  But after our trip to San Diego in 2018, things were pretty clear.” Matt and Karan flew to San Diego for the Jack Henry Conference. Without purchasing tickets, they gate crashed.  “We hadn’t even bought tickets but we thought,’ screw it.’ We visited all the booths and attended all the events until we eventually got kicked out.  But we did manage to obtain VIP passes for the big party on the last day of the conference”

And so, Posh was born.

Peak pose 

“Posh has inevitably shaped me and the person I am today. It’s taught me to lean into being uncomfortable, but I largely attribute that to Karan. He is fearless, he will put himself out there into situations that are challenging or scary and come out the other side with wins. Karan is a role model in that sense.” 

With time, Matt has learned the importance of boundaries and self care. You can often find Matt attending yoga at the end of the day. “There are always so many things to think and worry about. Turning off the mental switch is much easier said than done. But it’s a crucial skill in order to benefit from the rejuvenation that comes from downtime or a good nights’ sleep. I can’t afford a day where my mind is foggy, so it’s especially important to do everything for my well-being - eating well, sleeping, exercise, meditation, and yoga.”

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