The Musings of the Big Red Car

Saints, Sinners, Losers, and Winners

In the venture capital world, there is always a lot of information about the big wins of VC firms, but what of the losers? Or the deals they passed on they came to regret?

One firm recently put out a public announcement of the deals they passed on that turned out to be truly missed opportunities.

Here they are:

AirBnB — back in 2010, the venture partners looking at the deal thought it was a crazy valuation at $40,000,000. The last time AirBnB raised VC money they raised at 500X that original number.

Apple — Venture partner, “Outrageously expensive” at $60,000,000 valuation.

Atlassian — the largest Australian tech IPO is that nation’s history was a “bit rich” at $400,000,000.

ebay — “Stamps? Coins? Comic books? You’ve GOT to be kidding. No-brainer pass.” Haha. Sorry.

Facebook — “Kid, haven’t you heard of Friendster? Move on. It’s over!” partner speaking to Zuck.

FedEx — passed on Federal Express SEVEN times.

Google — no real explanation, just passed

Intel — got hung up on negotiations while a guy named Arthur Rock closed the deal.

Intuit — the company ended up being funded by family and friends after all of Sand Hill Road venture illuminati passed on the deal

Kayak — extensive due diligence uncovered a gaping flaw: US airlines would not pay placement fees on somebody else’s platform, but turns out that hotels will. Priceline bought Kayak for $1,800,000,000.

Okta — in the early days of SaaS nobody seemed able to understand the complex calculus of turning web apps into a business as a Cloud Area Network, so passed. Okta is a leader in that market with a stock market cap value of $14,000,000,000.

PayPal — passed because of the rookie team and regulatory nighmare. Ebay ended up buying PayPal for $1,500,000,000 4 years later.

Snapchat — VC partner arrives at LAX on a delayed flight, runs out of time, and has to blow off one meeting. Blows off Evan Spiegel and Snapchat which ends up as 2017’s largest IPO.

Tesla — liked the car, Model X. Bought one at full price. Passed on the deal. Tesla market cap currently greater than $534,000,000,000.

Zoom — loved the tech, engineer founder (Eric Yuan) but thought the space was frothy, passed. Zoom IPOed at $9,000,000,000. They bought some of the IPO.

The point, Big Red Car?

The point, dear reader, is this: nobody gets anything right all the time and we are as defined by our misses as we are by our hits.

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car.

Free sausage tortilla wrap at Green Mesquite BBQ in Austin By God Texas for the first person to identify the VC firm noted above. Go.