jdh

I am sure you are right, but as a long time resident, I think this is the trees not the forest -- I would estimate these barriers reduce 95-99% of the car traffic through them, even if someone cutting through is indeed a daily occurrence. Most are quite intimidating, many are totally impassable or require significant ground clearance.

Almost by definition, if it were a black swan, you couldn't hit 5/40 no matter how good or lucky you were.

Another point: it would help to know the terms associated with this investment to decide if it was smart.

Author treats stock as if it was a public company, which is understandable. i.e. these investors bought $1.2B of stock at a $17B valuation, and would need to see massive market growth, massive share, and margin stability to make 2x their money.

However, it's reasonable to assume they got preferred stock. So their return profile looks like: if Uber is worth anything more than a couple billion dollars (which they may view as near-certain), they get their money back + interest. Then they hold an option should Uber execute like Amazon, as others have suggested, and dramatically exceed their near-term market potential.

Valuing this is quite tricky: presumably the people who invested $250M less than a year ago thought: I only have to clear ~$400M to get my bait back, now that number is 3-4x higher.

While it is highly likely that the new investors have some sort of preferred return, it's possible (though less likely) that have a participating preferred or some other more complex instrument. Maybe the market price for straight preferred was "only" $12B valuation, and the company said: "How about we 'guarantee' you a 2x return, with a participating preferred instrument, but we want a 50% higher price, so in an upside case we are diluted less?"

This stuff is pretty common in these later rounds, though admittedly more on the "bubble unicorns" than the true unicorns, who have utmost market leverage. But you can see how even just the vanilla preferred stock would really change your personal calculation of whether you want to put your nest egg into Uber at this price.

Maybe not in the next few years. But people who pay with cash because they aren't allowed to be in this country and don't want a bank account (some portion of the unbanked) might enjoy shopping in the digital world by using some "digital cash".

Stock for stock deal. Price is arbitrarily set... All that matters is the percentage. If klout got ten percent, lithium just said they're value is $2B.

Klout did have a cool looking office for sure. Hard to find that in SF today.

" Why? Because that’s their job, to meet with entrepreneurs. It also means that if they schedule it on, say a Friday in SF at 11am, they can: a) avoid driving down to Sand Hill altogether, and b) arrive in Tahoe in time for a few evening runs. Be wary in thinking it’s anything more than that."

Thanks for the gratuitous kick in the nuts.

Did you consider that maybe the fact your meetings with VCs didn't result in good outcomes might be a signal of something else?

Having done both, running a company is definitely more work at the peak, but being a great VC is a ton of work, too.

You've got a lot to learn about VCs if you think we meet with you so we can go night skiing. Or that any VC goes night skiing.

<edit for tone at expense of humor >

Perfectly stated. Employee compensation is a contract freely entered into by the employee. If you think you deserve more, don't take the job.

However, I have sympathy for the fact that founder risk in SV has declined dramatically over the last twenty years, while employee risk has not, but if anything employee stock pools are smaller than they were a decade ago. Yet every founder says "it's impossible to hire good people".

I don't accept the word "misleading" -- I do not believe the page in any way misleads. It does not try to position it as anything other than a subscription, and the language is plain english.

Could they put the subscription details in bold? Could they use a larger font than all the other text? Sure. It's a tradeoff, for sure, and every retailer has to optimize their site to perform. Could they pop up three boxes after you click yes and say, "Are you sure?" "Are you really, really sure?" -- (yes, I know I'm being ridiculous) -- but yes, it is a tradeoff.

But with an NPS score in the 50's, nearing a million subscribers with very low churn rates -- happy users -- as investors we feel the business is healthy and being managed in an upfront way.

But, I can see how one might feel they would like it bolder or more prominent -- reasonable people could disagree on that.

I would submit that, when you come to view the site under the lens of clicking on a discussion about a fraud, and then go to it to decide if it is a fraud, and you (probably) aren't a likely customer and don't think "damn, that's a hot pair of boots for $40", you end up with a different lens.

Medallions required to pick people up on the street. Über is classified as a limo -- pre booked, no curbside pickup. Los dint need medallions.

However, the structure was created for old style limos: I.e. fat cat or prom kid books for hours, days in advance, not competitive with a taxi.

One could reasonably argue booking an uber 1 minute before pickup for a ten minute ride is a lot more like a taxi than a limo.

I agree, but I think there's a bigger problem.

I think first time entrepreneurs are prone to thinking that raising money is a win. Second time entrepreneurs almost never think that, they view it as an obligation.

A lot of young, first time entrepreneurs, if you told them: you can with certainty raise a $5M Series A, but with certainty the business will not work in the end, which you will figure out in 3 years -- they would still raise the money. They have a burning desire to to be a CEO, to build something, and they'll worry about the rest later.

In my view, raising money when you either have no idea if it's a good opportunity, or believe on early data that it's actually not (but you'll figure it out or pivot later), -- this is what I see in "fake it til you make it", "hustler" thinking -- is that when you're successful, you've now signed up to use some of the most productive years of your life chasing an opportunity that is likely not to be any good, when you could have held out for something better.

Happiness research indicates that people are consistently wrong about what's going to make them happy (or sad) -- the shiny new car will lift their spirits every time they get behind the wheel, but within a few weeks, it's just another car. I think this applies to fundraising as well: raising money for an idea you're not 100% convinced on has proven to tempt many founders, but in my experience, they later come to regret it.