In this post Dea WilsonLifograph founder, is doing an interview with Mitchell Kertzman, Managing Director at Hummer Winblad Venture Partners.

Mitchell was Chairman and CEO of Liberate Technologies, PowerSoft and CEO of Sybase.

Mitchell served as President of the Massachusetts Software Council and was Chairman of the American Electronics Association.

He is founder of the Massachusetts Institute for a New Commonwealth and served on the New York State Commission on Industrial Competitiveness.

Mitchell was awarded an honorary doctorate of humane letters from the University of Massachusetts, Lowell. He currently sits on the Boards of Five9, Flite, HubPages, NuoDB, and Palamida.


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What are 3 things people don’t know about you?

I’m a college dropout
I was a radio DJ in the 60s
I used to be a singer-songwriter (folk rock)

What companies did you pass on and later regretted it?


What does it take to get a meeting with you?

I am very open to communication. My email is listed on our website. Just send me a summary of what you do and your financial needs. I try to answer to every email I get. Just don’t send the email to everyone at the firm. And try to make it personal. Show me you did your homework.

What is an immediate turnoff in a pitch? Why?

An entrepreneur who distrusts VC starts on the wrong foot with me. If you want to be partners with us, there needs to be some level of trust coming into the relationship.

I also don’t like people with an attitude – they tend to always lose other people, whether they are team members, partners, customers, investors, etc.

I know that many VCs like to see potential acquirers in your deck. I don’t. It is good to have an exit strategy, but you need to first build a business. Your goal should be to solve a market need, not to think about a quick way out.

What would you consider the biggest mistake you’ve ever made?

I’ve spent a lot of time being a CEO, so I tend to focus heavily on P&L. One of the companies I’ve invested in had a great P&L but because I did not pay much attention to the balance sheet I did not see the trouble before it happened. As an entrepreneur you need to pay attention to all the metrics that matter, not only the ones that seem obvious to you.
Another mistake I’ve made through the years was hanging on to people for too long. If you see that someone is not a fit anymore, you owe it to the rest of your employees to cut the cord.

What would you consider to be your most significant accomplishment?

I am most proud of my family. Professional achievements pale in comparison to family.

Who is the most exciting person you’ve ever met?

I’ve met many interesting people but one of the most interesting was Barack Obama. Others that come to my mind are George HW Bush, Bill Clinton, Tom Friedman, and others.

What was your smartest career move?

After losing my job as a DJ I landed a job at an education software company as an audio visual technician. I had no exposure to computers until then. I asked my boss if I could try programming. That was the beginning of my career in tech.

Where do you like to go on vacation?

My family has a small ranch in Montana. That’s where we spend most of our vacations.

What is your investment philosophy?

We only invest in enterprise startups, looking for Series A financing. We do 3-6 investments per year.

I love startups that disrupt legacy markets. Some of the questions you should answer before pitching me are:

Are you solving hard problems?
Is it a software product?
Is your product a high priority for your customers?
Are your customers willing to pay for your solution?


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