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April 28, 2013

VF Profiles: Karen Rubin - A Passion to Build in Boston

Four months into her entrepreneurial residence at Matrix Partners in Boston, Karen Rubin can still remember the projects she worked on as a child in her parents’ craft room.

“My parents dedicated an entire room in our house as a staging ground for their children’s creative projects,” Rubin remembered. “I often felt like the family’s black sheep because I didn’t have much artistic talent, but I have always enjoyed photography, and I made a lot of pot-holders as a kid.”

Rubin’s favorite activity back then was making videos, and there is substantial evidence to prove it.  Nowadays you might recognize her from one of her 225 episodes as a co-host for HubSpot TV (now The Marketing Update), but a lifetime of creative drive has added more than just a webseries to Rubin’s body of work.  Since graduating from Trinity College with a degree in Computer Science she has become entirely at home in the Boston tech scene, where she says a culture of getting things done has allowed her to create and thrive.

“I love the process of building in tech because it’s exciting to see an idea take physical form,” Rubin explained.  “I’ve found the best way to build is by working in environments where there are many more things to do than there are people to do them, and Boston is rich with those opportunities.”

In reality, Rubin isn’t as far removed from her artistic family as her childhood stories might suggest.  Her father studied physics in college and has since become a professional artist specializing in kinetic motion devices.  Her mother studied sculpture and runs the family business that sells her husband’s art.

“My parents took an incredible leap in their transition to the art world, but if they were born in a different time they probably would have both gone into startups.  My mom would have been an outstanding product manager, and my dad especially loves to create things, so I can easily see him becoming a programmer in today’s world.”

Like her father, Rubin’s first job was in a large corporation, and it didn’t fit.  For a summer she interned at Unisys, but her liberal arts education at Trinity had whetted her appetite for creativity and teamwork across a variety of disciplines.  She had been a competitive runner all four years, and in addition to her major had delved deeply into Trinity’s German curriculum.  Working at an IT giant quickly became an obvious cultural mismatch.

“[At Unisys] I was working alone all day with no opportunity to be part of a team,” Rubin remembered. “It was always the same, and always lonely.  I think that generalists like me become less successful as companies grow and develop more rigid corporate structure.”

Rubin began distancing herself from that structure a year out of college after a brief stint at Credit Suisse.  She spent three years at a web development company called Promotions in New York City focusing on product management for big publishing companies. Shortly after TheStreet.com acquired her company in 2007, she started reading OnStartups, the blog of HubSpot CEO Dharmesh Shah, and became convinced she had to move to Boston.

“By the time I moved to Boston in 2008 I already felt cued-in to the startup scene thanks to Dharmesh’s blog” Rubin laughed.  “I was stalking him at networking events for six months when I noticed that HubSpot’s name was coming up in almost every conversation around town.”

Rubin said her mentor at TheStreet.com got her an interview six months later though a mutual connection with two of HubSpot’s investors at the time, General Catalyst and Matrix.  What unfolded was a prolific run that took Rubin first through the company’s customer success team and then to the top of its product team.  As a product manager she helped launch the first version of numerous tools for HubSpots’ Inbound Marketing Software platform including Page Grader, Social Media Tracker, Email Marketing, List Creation and Lead Nurturing.

Coming on with only 30 coworkers, Rubin took full advantage of being at an early-stage startup.  She moved quickly, transitioning from product to marketing in 2011 and carving her own niche as an architect for new marketing tools.  She remained a generalist, synthesizing work across disciplines and sharing what she learned on her weekly video podcast.  And she never stopped learning.

“At HubSpot we had a saying: ‘products will never be ready, only readier.’  Eventually I got burnt out on building new tools all the time, but it was always invigorating to churn through new ideas and invaluable to learn how to let go of one project while moving on to the next.”

Four months after her departure from HubSpot, Rubin isn’t looking to dive into another startup just yet.  While nurturing a genuine fascination with venture capital, she sees her residence at Matrix Partners as a fantastic opportunity to survey the possibilities for what to build next.

“I tend to jump fast,” Rubin said, “and learning about venture capital is forcing me to take more time in my decision of where I’ll go from here.  Being at Matrix also allows me to advise people on a huge variety of ideas almost every day.  I’ve probably met between 60 and 70 new companies in my first four months alone.”

Rubin already has some favorites in the parade, including Quantopian, Privy, and Sold.  It’s clear that her brief respite from the trenches of Boston startups will only be as long as her search for the next challenge, the next project, and the next great team to help make her visions a reality.

Ben Mirin is a
professional videographer, journalist and contributor to VentureFizz.  You can follow Ben on Twitter (@benmirin) by clicking here.

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