Category Archives: Venture Capital

Which type of investor makes the best board member?

A few days ago, WSJ’s startup & VC blog referred to an NVCA study where entrepreneurs complained about the lack of operational experience in some VC board members. I’ve been an entrepreneur as well as a VC. The biggest travesty … Continue reading

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A new spin on pitching and fundraising

Every conference having anything to do with entrepreneurship and venture capital has the obligatory “pitching & fundraising” panel. I’ve been on enough of them to have a sense of how disappointing they can be for the audience. Experienced folks hear … Continue reading

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Startups VCs are dying to invest in

VCs have a big problem. Many entrepreneurs just don’t want to solve big problems anymore. After hearing the fifth socially-responsible-Twitter-client-running-on-fuel-cell-powered-unlocked-iPhones pitch this week, it’s understandable how VCs want to take August off. So, in the interest of helping everyone, I’m … Continue reading

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Comparing term sheets

Jeff Bussgang did a guest post on PEHub on the topic of how entrepreneurs should look at and compare competing term sheets. Jeff correctly points out that the pre-money valuation of the company is not what entrepreneurs should focus on … Continue reading

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The responsibility of an entrepreneur: when to shut down early?

Jason Calacanis has written a lengthy post with a lot of good advice for entrepreneurs who are facing the potential failure of their business. It has good tips for extending the runway and making do with less. It also has … Continue reading

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Founder Dilution

Founders often ask me, “If I own X% after my first investment round, how much will I be diluted through financings until exit?”. There are rules of thumb but there is no good data about what happens to common stock. … Continue reading

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For the MIT 100K Participants: Executive Summaries

I was invited to speak tonight at the MIT 100K Web/IT track mixer but, unfortunately, I’m sick (which wouldn’t have necessarily prevented me from going) and have lost my voice (which would have made going to the event pointless). So, … Continue reading

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The Anti-Patterns of Bootstrapping

The three most common bootstrapping mistakes I’ve observed: Setting the wrong bootstrapping objectives. Prototype? First paying customer? CFBE? I often meet with startups that are bootstrapping to a particular objective with the expectation that it will allow them to achieve … Continue reading

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Startup #5 & Future Forward Tidbits

My blog rank is in the drain. I have been busy creating a new startup company, the fifth I’ve done at Polaris and the second (after Plinky) I’ve co-founded since I shifted roles to spending 100% of my time on … Continue reading

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Attributing Entrepreneurial Success

I’m flying back to Boston after a crazy week of Plinking, TC50ing, CTIAing and thinking about starting a new company in the mobile space. My brain is jacked up and exhausted at the same time. So much to process… Living … Continue reading

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