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Every day I get emails from entrepreneurs that make me think. In this case, it’s from a friend who is on the fundraising trail. He started off the email with “I felt compelled to share this with you as someone who would appreciate it.” I thought it was dynamite and asked him if I could share it since – in its unedited form – it captured so nicely what I expect many entrepreneurs feel. And, just as importantly, it’s something I hope VC’s realize that entrepreneurs – even very experienced ones – feel.
I am fortunate to have successfully raised venture capital from top tier investors before.
I have been a failed and successful CEO and know the difference.
I have earned my CEO stripes by being a successful operator in startups and big organizations.
I can lead, problem solve and think strategically. I am technically adept, I can sell. I work hard.
Yet, as I set out to raise money, I still have a great feeling of unease of the result. I guess I have humility as well.
I’ve noticed, or maybe more accurately, I’ve become aware of the ether that is between a venture investor and entrepreneur. In the ether, all things that can make or break a deal exist: idea, market risk, technical risk, team competence, economy, deal flow, competition, VC mood that day, entrepreneur pitch that day, first impression, gut feel, blog post for or against the idea read that morning, breakfast/no-breakfast, bias for or against, smarts or not-so-smarts of the VC and entrepreneur.
In my pitch experience, VCs I have been convinced hated me and my company after my pitch have invested. VCs I am sure as shit loved me and my company after my pitch blew me off. I have also been right that VCs I thought hated me and my company told me they in fact did; and, those who loved me and my company did in fact invest. It’s been a crap shoot at best.
Assuming there is something of merit in the idea, market, team and company, somewhere in the ether is a term sheet and a kick to the curb. Coalescing just the right combination of elements in the ether at the right time has proven to be more art than science. Anti-portfolios highlight how successful companies didn’t get it coalesced with one investor but did with another.
If I get it right and a financing comes together for my new company, I hope to have learned something that tips the scales of randomness in the scrum.