One of the more sordid stories in Silicon Valley history is buried in the book: ‘Founders at Work’
It’s the story of Hotmail and Draper Fisher Jurvetson (DFJ).
Sabeer Bhatia and Jack Smith were the founders raising money for Hotmail.
DFJ invested $300K at roughly a $2M post-money valuation.
The important detail wasn’t the valuation.
It was DFJ’s right of first refusal on the next financing.
Bhatia says he didn’t appreciate what that provision could mean.
Then Hotmail started taking off.
Bhatia went out to raise another round.
Here’s where it gets ugly.
According to Bhatia’s account, investors would call DFJ as part of their diligence.
Bhatia alleged DFJ discouraged them from investing.
His interpretation: kill the competing bids, preserve leverage, and buy more of Hotmail at a lower valuation.
Meanwhile, Hotmail was running out of cash.
Eventually they were down to a couple weeks of runway and approaching a payroll they might not make.
DFJ knew it.
The founders knew it.
And every day that passed shifted negotiating leverage away from the founders.
Hotmail ultimately took the financing.
Never let a single financing counterparty become your only option.
That’s
@travisk’s point and why he ran an auction.
Founders obsess over price (valuation).
They should obsess over terms (governance, control, ROFRs, etc).
The book ‘Venture Deals’ is a classic that entrepreneurs read now and has since set standards.
post script: Microsoft acquired Hotmail for $400 MM.
That was a massive head turning deal back in 1997.
Hotmail was less than two years old, and had zero revenue.
Travis Kalanick reveals Bill Gurley pressured him to take a $6 billion valuation. Two months later, he raised at $17.5 billion.
"Gurley was convinced it was the end of the world and we've got to raise, and just take your first term sheet, just f*cking take it."
"We got to a place where I just wouldn't talk to him. If he reached out to me, I would talk to him, but I just wouldn't try to engage because it was always that. So Emil Michael would handle this part. He would handle a lot of the investor relations."
"Anyways, two months later, we got a round done at a $17.5 billion pre."
"We were already planning IPO stuff. [Benchmark Capital] didn't know it. But they also never expressed the desire to be like, 'Hey, dude, you gotta IPO.' It was never brought up."
"If you think the world's about to end and you've got this thing that's worth a ton of money, you could get to a weird place. Especially when you're a VC, you don't have any control. You're not running anything. So now your entire outcome in life is due to this guy."
"You could get into a place where you're running a war room to destroy him. And that's kind of what happened."
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