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We Love Boston Entrepreneurs: Dharmesh Shah


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This is the first in a series of interviews with some amazing entrepreneurs in the Boston area. These folks have been selected because they are not just building a business but giving back to the entrepreneurial community in some way. They might be sharing their hard-won experiences on a blog, funding startups themselves, or mentoring other startups in the Boston area.



Richard: One of the things I have admired about you is the ability to create a personal brand and a business brand in parallel. Is that a deliberate decision or did it happen by accident? And is it something you recommend other entrepreneurs and business people should consider doing?

Dharmesh: Yes.  I think entrepreneurs should start building their personal brand even before they start thinking about building a company.  The reason is simple — the personal brand can be used to help grow the company.  In my example, I had created a relatively popular Startup blog (  This was viewed by thousands of people, many of whom then became readers of my business blog, tried out the product and became customers.

Another reason to invest in a personal brand is that the startup might change, you might part ways, it’ll be nice to have an identity outside of the company you started.

Richard: You are clearly very active in the local entrepreneur scene in terms of attendance and speaking. As an entrepreneur I find it is often hardest to quantify the value of attending/participating at an event. As a “data obsessed” person how do you evaluate and justify the involvement?

Dharmesh: Since I’m a nervous speaker, I try to limit the number of speaking invites I accept.  It’s less about ROI, and more about MMI (Minimize My Introvertedness).  Basically, I look at some simple things:  Is the topic in one of my areas of interest (startups/funding/marketing/technology).  How large is the audience?  Will I be speaking at a main session or in a break-out session.  Or worse, be on a panel (I can’t stand panels).  The filters are simple:  My goal is to try and help as many people as possible with the limited energy that I have.  If I can get in a front of 1,000 people for an hour and teach them inbound marketing — that’s good.  If I’m in a breakout with 50 people, and one of 4 people on a panel, it’s just unlikely I’m going to be able to move the dial much.

Richard: You’ve put together an amazing team at Hubspot but it’s also grown very quickly. Even though there is a high unemployment rate it’s is really hard to find the super-star employees that seem to be part of your team. How do you first find such talented people and then manage to retain them?

Dharmesh: Finding is the harder part — retaining is generally easier.  For finding we use all the common methods (recruit from the network, use recruiters sparingly, etc.).  The key here is to ensure that the people that have already been hired know that they’re supposed to try and hire people even better than they are.  When you have a strong team, it tends to work towards making the team stronger.  Everybody wins.  Retention is easier:  Create an environment that people can do their best work, let them make a difference, teach them things they need to know — and most importantly, surround them with the smartest, most passionate people they’ve ever met.  If you do just that last piece, you can get away with a whole lot of other mistakes.

Richard: As an angel investor you get to see a lot of cutting-edge business ideas. Do you have any insights into what new trends might be interesting for entrepreneurs to be thinking about right now?

Dharmesh:  I don’t see that many cutting-edge ideas.  I have a particular type of startup that I like to invest in (web software, consumer or small business).  Something simple that I can hopefully understand — and use.

Richard: There has been a trend in venture baked companies to replace the founding team with a “hired gun”. I personally don’t like that approach and prefer to see investors backing the founders through all the stages of growth. What’s your perspective?

Dharmesh: My perspective is simple:  Experienced, savvy founders that are trying to build the company in the best way possible are not violently opposed to new folks being brought in.  The danger is that the common patter of “parachuting in” a CEO from the VCs network just doesn’t work out.  Key employees leave.  Trust erodes.  It becomes harder to hire.  The magic is lost.  My leaning is to keep founders through the ups and downs (and there will be ups and downs) and help wherever possible. But, that’s just me.

Read the full line-up and entrepreneurial interviews here: We Love Boston Entrepreneurs

Author Richard Banfield

As CEO, Richard leads Fresh Tilled Soil’s strategic vision. He’s a mentor at TechStars and BluePrintHealth, an advisor and lecturer at the Boston Startup School, and serves on the executive committees of TEDxBoston, the AdClub’s Edge Conference, and Boston Regional Entrepreneurship Week.

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