Brandeis International Business School

021: The Workplace Transition

A serial entrepreneur’s perspective on what it takes to make a difficult transition

Today’s guest, Paul English, is the co-founder of five software companies – Lola.com, kayak.com, GetHuman, Boston Light, and Intermute – and the founder of three nonprofits – summits.org, kingboston.org and winterwalkboston.org.

From the Dorm Room

Today’s story starts a little bit before college, when Paul was in high school. He switched schools almost every year because he found it difficult to pay attention didn’t do very well in classes, although he always tested very well.

So Paul didn’t do very well as a student, and he wasn’t sure if he even wanted to go to college. He actually only applied to one school, Boston College, aso he went to UMass Boston to study music and computers. He was also already a self-taught programmer before graduating high school, so he ended up working full-time throughout most of his undergrad career.

Both in school and at work, he was just trying to expand the breadth of his engineering background.

To the Boardroom

After college, Paul worked at Interleaf for six years, and he was very successful there. He got progressive promotions and moved up the ladder until the business was sold. He was then recruited to an internet startup called NetCentric, which was a VC-backed startup in Cambridge.

He was hired to run engineering at what was a relatively small 10-person company, and then they started growing. Paul and the founder had some disagreements on how to manage teams, so he left – although, today, Paul and the company’s founder joke about whether he was fired or he quit.

“And I remember leaving then and feeling like a failure; that I was very successful at Interleaf, there for six years with progressive promotion and all that, and then, ultimately, failed in this startup.”

Paul didn’t know if he should pursue management or programming, so he took some time off and ended up developing a website. He spent a year with no income working on that website, which led to the creation of his first real company, Boston Light, which he ended up selling to Intuit. But it really started from building his own game site as a way for him to get back into hands-on engineering.

And that’s something he suggests anyone who is or will soon be entering the workforce: you need to take the time to master a craft.

When you leave college, you’re taking five classes at once, and they may all be on different topics. But when you work within an organization, you typically only work at one thing. So you have to ditch the master of all trades mindset and become a craftsman.

The Entrepreneurial Edge

Every week, we highlight one piece of advice for aspiring, struggling and successful-but-want-to-be-even-more-successful entrepreneurs:

A lot of people think of being an entrepreneur as a solo thing – and solopreneurs do exist – but very few ideas or companies are built solo. And one of the things that helped Paul in both his programming career and his entrepreneurial endeavors is learning to navigate group dynamics and work with diverse groups of people.

Growing up as one of seven children in a small house made Paul very focused on who's around him, who's doing well today, and who's not – and that caused him to think quite a bit about teams, at a young age. "What's working well on a team? What's not working well? And then... one of the coolest things about UMass Boston is that it’s a really diverse student body: a lot international [students], a lot of people of different ages, different races. And I learned about how to build teams where people come from very different backgrounds. And that has been really useful to me."

Adding onto that, Paul also wishes he’d learned to effectively manage people that might be struggling earlier in his career. He says, "I wish I had been more of a mentor and coach than a critic. So, I would encourage people, early in their careers, if you're really strong at your crafts, don't just become a critic to people that you perceive as not as strong, but become a coach."

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