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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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What Angel Investing & Florida Condos Have in Common

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They have marked-up paper gains propped up by an over excited venture capital market that has validated their investments. Logic tells me the following: It is hard to make money angel investing. The best angels will do very well just at the best real estate investors did well in good times and bad.

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Angel Investing: Skill 3 – Relationships with VCs

Both Sides of the Table

In these scenarios angels made great returns precisely because they didn’t need to dip their hands into their pockets a second or third time, their companies didn’t go bankrupt and they didn’t get buried in the cap tables by large VCs who put in “pay to play” provisions in tough times. So where are we now? It’s hard to say.

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Angel Investing 4 – Why You Need Deep Pockets to Win Big

Both Sides of the Table

This is the same with angel investing. Protecting every investment – including bad hands – is a losing strategy in poker & in angel investing. From an investment perspective you need to absorb three scenarios in angel investing that require deep pockets. the diversity problem.

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Angel Investing Skill 2 – Domain Knowledge

Both Sides of the Table

Yet the truth is that I see angels with great deal flow & great instincts whom I believe will only perform well in times that favor angel investors (like 2010) where there are early exits. Tags: Startup Advice Tech Market Analysis VC Industry. I don’t believe these times will last.

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Angel Investing – The Most Underrated Skill: Access to Buyers

Both Sides of the Table

It’s hard for me to imagine that angel investing outcomes judged 10 years from now will have a drastically different profile. The best angels or angel funds will do tremendously well. As I’ve said many times, investing shares many of the same characteristics as gambling.

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Angel Investing: Skill 3 – Relationships with VCs

Both Sides of the Table

If you’re an angel – I suggest that a portion of your time go into cultivating these relationships. Tags: Startup Advice Tech Market Analysis VC Industry. And resist the temptation to extend thy middle finger. As tempting and as deserving as it might be.