He's a successful entrepreneur whose Boston-based company has raised over $65 million in venture capital and was the subject of tech writer Dan Lyons' book Disrupted. But what helped shape Dharmesh Shah into an inbound marketing powerhouse?

Check out these incredible facts about the co-founder and CTO of HubSpot:

1.  A pioneer of inbound marketing, Dharmesh Shah met his HubSpot co-founder Brian Halligan when they were grad students at M.I.T.  The two set out to create an online marketing platform, driven by the flagging success of direct mail and other old school marketing tactics.

2.  Shah graduated M.I.T. with an MS in the Management of Technology, which he once described as, "... this weird kind of engineering mixed with like an MBA kind of thing... Essentially, an MBA with some technical geeky stuff thrown in."

3.  His first startup, Pyramid Digital Solutions, launched in 1994 when Shah was 24 years old. After bootstrapping it with less than $10,000, he sold it for millions to SunGard Data Systems, the company he'd worked for when he originally came up with the idea, in 2005. HubSpot is Shah's third company.

4.  Because he didn't like selling, Shah had a genius idea and convinced SunGard Data Systems to actually sell that first software he left their company to startup. Without even realizing what it was at the time, he struck a distribution partnership with a major player in software sales.

5.  Shah founded that first company with a co-founder: his brother, who was only 17 and just out of high school when Pyramid Digital Systems launched.

6.  He landed his brother a job at SunGard alongside him by convincing a manager that hiring a $75/hr consultant was a waste when the job was something his teenaged brother, then a grocery store clerk, could do just as well.

7.  Before co-founding HubSpot in July 2006, Shah had promised his wife he wouldn't start another company and would be an angel investor, instead. He started investing in other companies while at M.I.T. On his decision to start another company after promising not to, he's said, "I could not help myself. It's just a genetic flaw!"

8.  Shah counts Innovator Of The Year, Mass. TLC, 2009; Inc. 500 Award, 2000, 2001 & 2002; Boston Globe, #1 Hi-Tech Innovator, 2011; and Social Media Allstar, MITX, 2009 among his awards.

9.  From year one, HubSpot has had an internal wiki that gives employees access to all kinds of company information including cash balance, board decks, bank balance, sales figures, burn rate and more. Shah believes people do well within his company because of this transparency and other aspects of HubSpot's culture.

10.  He founded and writes for OnStartups.com, which has more than 350,000 members in its online community.

11.  Shah has identified blogging and social media as the two accelerants that helped HubSpot grow as quickly as it did.

12.  He still tries to write code every day and says it "keeps me in touch with reality and makes me a better entrepreneur.  Plus, I enjoy it."

13.  Before the HubSpot market product was even written or launched, Shah and Halligan started the HubSpot blog. They used it to position their software as an inbound marketing solution before it existed in the marketplace.

14.  According to Shah, insecurity is one of the worst fates to befall an entrepreneur. "If you could manage to take insecurity out of a team, amazing things happen. If you could take insecurity out of yourself, amazing things start to happen," he's said.

16.  Shah said he faced his darkest entrepreneurial days in his first business, with the hiring of their first employees and facing down cash flow issues. By 2013, he said, "The thing that I worry about is that sometimes it's a matter of how you define success. For us it's like living up to the potential of the team that's here... That's what really keeps me up."

17.  Shah wrote his thesis on... you guessed it, software startups!

18.  Now an angel investor, Shah has said he tends to be slightly biased towards entrepreneurs who "have a point to prove" or even have a "small" chip on their shoulder.

19.  Shah has publicly stated that he hates enterprise software despite (or maybe because of?) the fact that his first company was an enterprise software brand. He explains why: "It's particularly bad now. Back in the 90s it wasn't so bad. It's  revenue concentration so you have a few number of customers that are writing you really big checks. Which then impacts your product road map. Because OK, if they're writing big enough checks you do what they ask you to do. We can not do that... People don't realize this but the feedback loop and the shortness of it has such a high impact on your overall success and happiness."

20.  In his first several dozen angel investing deals, which coincided with his founding and early growth of HubSpot, Shah was so pressed for time that he never met or even spoke on the phone with half the entrepreneurs he funded.

21.  Shah met a number of entrepreneurs online through his Onstartups blog and, when inspired, would decide to fund their projects. He was an early investor in Backupify, Shareaholic and Buffer, among others.

22.  He counts PHP, Codeigniter, MySQL, Python and Django  among his skills.

23.  One of the first things he does as an "introverted angel" is Shah Google searches an entrepreneur who's caught his attention.

He's said, "I'm going to find everything you've ever said, written or shared, essentially. I think the mark of a great entrepreneur today is that someone is in the game. It's not just a matter of, 'Oh, I woke up this morning and said this was a great idea. I'm going to go build a start-up.' You need to put yourself out there a little bit and give me evidence that you actually care."

Dharmesh Shah showcased his ability to roll with the punches in his company's response to the controversy created by the release of Disrupted.

There's much to be learned from the successes of entrepreneurs like Shah, but even more from the way they handle themselves when the chips are down!

You can (and should) read Undisrupted: HubSpot's Reflections on Disrupted here.

With notes from  This Week in Startups E334 and Mixergy.

Published on: May 16, 2016
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