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Matt Douglas, Founder and CEO of Punchbowl.com

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7 Pithy Insights About Dharmesh Shah

Before I begin, a disclosure: Dharmesh is an investor in Punchbowl, an advisor, and a business friend. However, even though I know him fairly well, he remains an enigma for many people in the Boston startup community (and beyond). What makes this man tick? How does he churn out such great content, attract fantastic people to join HubSpot, and invest in so many companies as an angel investor?

I first met Dharmesh at an MIT event back in 2006. Looking back, it was quite an amazing night: the founders of Reddit got up and spoke about how they just re-wrote their app in PHP and Dharmesh spoke about the small/medium business market that he felt was underserved. I’ll never forget the first time I heard him present. Without slides or fanfare, he transformed into a professor. The class was mesmerized by his oratory skills, and not a person in the room was in doubt that he was onto something.

Since that day at MIT, Dharmesh has built HubSpot into of the fastest growing companies in Boston and he continues to share his startup knowledge with his “pithy” insights and numbered tips. But what makes him tick?

What is the secret mojo that makes him so interesting? Here are my 7 pithy insights about Dharmesh Shah:

1) He’s an extroverted introvert: If you are a regular reader of Dharmesh’s, you know that he likes to talk about how he is an introvert– especially at industry functions. Well for an introvert, I’m always surprised at how many events he attends and how many people surround him at these events. He has lots of interesting things to say, and people love to hear him speak. Sorry Dharmesh, I’m married to a wonderful introvert– and I can tell you that she can out-introvert you any day.

2) He’s a developer at heart: Almost every time I meet up with Dharmesh, he tells me that he was up late some night that week coding. He loves to create software, and he makes a conscious choice to keep his skills sharp. Much of HubSpot’s success can be traced to a little piece of software he built called Website Grader (now called Marketing Grader).  Dharmesh still beams with pride when he talks about how that software has helped build his company.

3) He’s an amazing public speaker: As I described above, the first time I met Dharmesh was at a Boston startup gathering. He sheepishly stood up in front of the chalkboard, apologized for not having PowerPoint slides, and proceeded to give one of the best pitches I’ve ever seen. He described the problem with precision and grace, and led us all down the path of his thinking. I took furious notes (and I admit to looking back on them many, many times). It was a lesson in public speaking and how to give a pitch. One I’m still trying to emulate.

4) He’s a creature of habit: Dharmesh and I have dinner about once a year, at one of the few places that he frequents. If you ever have dinner with Dharmesh, the hostess will know exactly where to take you because he usually sits at the same table. I imagine that Dharmesh is a creature of habit in most areas of his life, and there’s something steady about him that makes him so likable.

5) He’s gracious and forgiving: I’m usually very good with people’s names, but once in a while I get stuck and repeat the same mistake twice. It happened with Dharmesh. When I first interacted with him years ago, I sent Dharmesh an email and spelled his name “Darmesh.” Mr. Shah corrected me over email. But a week later, I did it again (oh the embarrassment!). I felt very stupid, but Dharmesh put me at ease. “It happens all of the time” he wrote. I’ve never made that mistake again.

6) He’s always thinking long-term: Dharmesh may not know it, but he had an amazing impact on me with a simple conversation that we had early in our relationship. We were talking about web domains, and he mentioned that he casually buys domains as he thinks of ideas. As he told me, that way “I’ll be ready for my next startup.” This rocked my world. Why? I had been spending so much time thinking about domains for Punchbowl.com that I hadn’t considered the possibility of another startup sometime down the road. I had found many good domains, but they didn’t fit the business I was working on today. I raced home that night and bought 30 domains over the next few days. Dharmesh helped me realize that I can be an serial entrepreneur.

7) He’s a Dad first : When I first met Dharmesh, it seemed unlikely that he would ever have children. He said that he and his wife loved their ability to travel and didn’t see a child in their future. And then Sohan came into his life. When I meet with Dharmesh now, the conversation always starts with his family. He lights up when he talks about his child, and you can see that he’s a different person than he was before he was a Dad. His priority is on his family, and he makes decisions everyday so that he maximizes his time with Sohan (I have a young child — this is why we haven’t seen each other as much over the past three years!). If you interact with Dharmesh know that he very much cares about getting to know you first before he learns about your business.

Dharmesh Shah is one of the leaders in the tech community of Boston, but an enigma to many. Hopefully these 7 Pithy Insights might provide a little more background into what makes him tick and why he’s been so successful. What did I miss? Add your own pithy insights in the comments.


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©2019 Matt Douglas