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Angel Investing (1): Dealflow – Are You Sitting at The Right Poker Table?

Both Sides of the Table

I believe the rise in angel investing is here to stay and the professionalization of this class (aka “super angels&# or “micro VC&# ) is a good thing for the VC industry and for entrepreneurs. But I fear that for most angel investors who invest over the long haul angel investing will not be a profitable endeavor.

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The Changing Venture Landscape

Both Sides of the Table

On the one hand, you’re over paying for every investment and valuations aren’t rational. In 2001 companies IPO’d very quickly if they were working, by 2011 IPOs had slowed down to the point that in 2013 Aileen Lee of Cowboy Ventures astutely called billion-dollar outcomes “unicorns.” That used to be called A-round investing.

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What Makes an Entrepreneur (4/11) – Resiliency

Both Sides of the Table

This is part of my new series on what makes an entrepreneur successful. I originally posted it on VentureHacks , one of my favorite websites for entrepreneurs. That next round of investment is proving difficult. Resilience is one of the tell tale signs of an entrepreneur. It’s a gritty existence.

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How to Manage a Startup Through Troubling Times

Entrepreneurs' Organization

Like the downturns in 2008 and 2001, this has been a very trying time for entrepreneurs running startups. Many entrepreneurs are reliant on outside funding, whether angel investors, venture capitalists or strategic investors , to keep the venture going. Remember that you are not alone. Join a CEO peer group.

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Bad Notes on Venture Capital

Both Sides of the Table

At an accelerator … Me: Raising convertible notes as a seed round is one of the biggest disservices our industry has done to entrepreneurs since 2001-2003 when there were “full ratchets” and “multiple liquidation preferences” – the most hostile terms anybody found in term sheets 10 years ago.

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Want to Know How VC’s Calculate Valuation Differently from Founders?

Both Sides of the Table

Due to competitive markets we ended up with a pretty good term sheet until we needed to raise money in April 2001 and then we got completely screwed. And for some strange reason entrepreneurs didn’t share this information. I’ve started from day one trying to build total transparency into my process with entrepreneurs.

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What I *Would Have* Said at TechCrunch Disrupt

Both Sides of the Table

The VC industry has different segments in it that have different fund sizes, different investment amounts and different risk / return expectations. These days that’s not the case and it’s a great outcome for entrepreneurs and for innovation. If you invest it in startups you’re a VC professional money manager.