Advice from a successful entrepreneur



"The best entrepreneurs are the ones who have a proclivity to action and to get something out there as quickly as possible."

Interview with Dharmesh Shah
Chief Technology Officer & Co-Founder of HubSpot

Q:

What are the three to five most serious mistakes you see burgeoning entrepreneurs make—time and time again?
A:
There are several:
1) Trying to go it alone instead of finding at least one co-founder. As it turns out, entrepreneurship is a challenging adventure, and it is very, very helpful to have a partner. Not only does it help spread the work and leverage multiple skill-sets; it is nice to have someone to talk to during the inevitable dark times.
2) Not focusing enough on the customer and determining if there is a viable market.
3) Spending too much time and money on non-essentials in the early stage. Every available resource should be spent getting customers and meeting their needs.

Q:

In your "Moneyball" article, you wrote, "Your goal shouldn't be to buy players; your goal should be to buy wins." Would you mind talking a bit more about the do's and don'ts of strategic hiring?
A:
In the early days, it is tempting to make hires that look great on paper. But if those people can't actually do the job, it doesn't matter how good they look on paper. In the early stages of a company, everybody needs to roll up their sleeves and do real work—not “manage” other people that are going to do the work.

Q:

What are three to four key decisions that led to the success of HubSpot?
A:
I think several things contributed to our growth. First, we decided early on that we were going to try and build a long-term company. The intent was never to build something that was designed to be acquired. Second, we stuck to our guns in terms of our vision, [which is] to help organizations transform how they do marketing. Third, we were exceptionally picky about who we brought on to the team—and ensured that we maintained an environment where the best people want to work.

Q:

Tell us about www.onstartups.com. How did this project come about? Any big plans?
A:
When I was in graduate school at MIT, I had to write a thesis. Mine was titled “On Startups: The Patterns and Practices of Contemporary Software Entrepreneurs". As part of collecting outside input for the thesis, I decided to start a blog (this was in November 2005). I took the first two words of the thesis title (On + Startups) and came up with OnStartups.com. The domain was available, so I just started blogging. Through the beauty of inbound marketing, it built up a relatively large following. Today, OnStartups reaches over 400,000 people. In terms of big plans, I'm working on a community for OnStartups

Q:

Raising capital: What are the pros and cons, do's and don'ts that first-time business owners should consider? A little background: We saw your post that advises us to run fast if a VC asks about an exit strategy. What other considerations (such as giving away the farm too early) do entrepreneurs need to think about when trying to raise capital?
A:
First-time entrepreneurs should be careful not to jump into fundraising mode too soon. I see too many entrepreneurs immediate try to raise venture capital and then quickly (or slowly) become frustrated with the process. As it turns out, raising venture capital is exceptionally hard. My advice is try to make as much progress as possible without trying to raise funding; because, by getting traction, the odds of successfully raising capital go up dramatically.

Q:

Say a friend tells you she plans to quit her job and start her own business. She pitches you the idea and asks for constructive criticism. What are the first questions you will ask her to assess the plan? How do you go about vetting the pitch?
A:
Usually, the first thing I want to know is: Who is the customer? Specifically, whose problem is a business solving—and is there evidence that people care enough to have that problem solved? Then, I try to determine how long it will take to get to the first customer. The best entrepreneurs are the ones who have a proclivity to action and to get something out there as quickly as possible. In terms of judging ideas, that's really, really hard to do. Judging people … that's much easier. And, in terms of vetting pitches, I try not to do that. I'm pathologically non-confrontational, so I avoid situations where I have to push back on people.

Q:

What sacrifices did you have to make to reach success, and which ones were unexpected?
A:
The biggest “sacrifice” is time. First-time entrepreneurs have to spend crazy amounts of time working on their business. There’s a reason: There are always more things to do than there is time. You're learning things as you go and often experiencing “near death” experiences relatively regularly. It's a stressful experience.

Q:

What motivates you?
A:
I like to build things that solve problems. Everything else is incidental.

Q:

What didn't we ask that we should have?
A:
If you could keep only one of your blog articles and had to delete all the rest, which one would you keep? Answer: http://SorryButNo.org, an article I refer to every week -- it has made a massive, positive impact on my life.