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

Back in 1999 when I first raised venture capital I had zero knowledge of what a fair term sheet looked like or how to value my company. 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. It was accept the terms or go into bankruptcy so we took the money. Those were the dog days of entrepreneurship.

But the truth is that I didn’t really understand just how screwed I was until years later when I finally understood every term in a term sheet and more importantly I understood how each term could actually be used to screw me. Things like “participating preferred stock” in legalese unsurprisingly never actually call out, “hey, this is the participating preferred language.” We got a 3x participating liquidation preference with interest (not participating with a 3x cap, but 3x participating. Ugh. I explain the difference later in the post or you can click through on this link above for an explanation).

Back then VentureHacks didn’t exist. Brad Feld hadn’t written his seminal “term sheet series” and The Funded hadn’t yet been created. And for some strange reason entrepreneurs didn’t share this information. Other founders, “as a privately held company we don’t disclose our valuation.” Me, “dude, I’m not a journalist. I just want to figure out what a fair valuation is.” I figured all the VC’s talked so we should. Duh.

I don’t feel that as a VC sneaking in nefarious terms into a term sheet that the entrepreneur doesn’t understand is a good way to build a long-term relationship nor to build a long-term reputation but this does happen and more frequently than we all would like. I’ve started from day one trying to build total transparency into my process with entrepreneurs.

This starts with understanding how VCs and entrepreneurs often see valuation differently. And no prizes for guessing which side of the table really understands the right answer. I’m not sure I really even need to write this at length because Nivi absolutely nailed the topic in his article “The Option Pool Shuffle.”