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This reminds me of a quote I heard during the dot.com bubble. "If I can't expect 1000% return I'm not investing in a company". It's such a high level of expectation that you just know a correction is coming.


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> "Anything but going all the way to zero" seems like the current tone.

You don't invest in a company without expectations of ROI


If you don't demand at least 100x returns why would you invest in something with a 99% chance of total failure?

Is your argument that investors should willingly do things with a negative expected value?


People say this a lot but it's worth questioning, because the "unrealistic expectations" also make the portfolio math work, and if the math doesn't work, not liking the expectations doesn't turn a broken investment into a viable one. You can do a really superficial analysis in 5 minutes of Google Sheets to work this out for yourself, and at least crystallize your implicit expectations about the number of companies in your portfolio you expect to be profitable in N years as opposed to dead and gone.

> return money to investors

Do the investors care? If they're not making 100x return on an investment, will they truly care about 0.5x return? My feeling is that most would just say "OK, you have a good team, you have money in the bank, pivot and go wild".


Basically, people are expected to be more discerning about what they'll yeet money at. Remember, wealth tends overtime to trickle up, so good or bad investment, the people at the top'll probably make it back eventually anyway.

The big diff is now founders need to measure up to "can you make it back at least X% in Y% time?) Where X% is now non zero.


The counterargument is that nobody knows how much value they will have--and sometimes people are too optimistic. See "Investor Storytime" here: http://idlewords.com/talks/internet_with_a_human_face.htm

Investors are like companies, 60%-80%(Dubious estimation) are not that great, but every so often there is a good one.

That's how "vision" investors are supposed to work. You expect 99% of your investments to fail and 1% to give you 1000X returns.

That said, I agree that WeWork isn't exactly "vision".


Once past a certain size and far enough in the hole, being marginally profitable isn't going to help. It's go big or go home that counts. Investors aren't interested in a +-3% annual return, they want 1000% or nothing.

No one should ever invest in a company without knowing an accurate projection. People who do this are just playing the lottery.

It's hard to understand why if you're able to consistently do 100% yoy you'd even bother or waste any time selling investments products.

Interesting. One way you just made me think of this is considering what a 'great' investment return is. Let's say it's 20%.

If you're getting 20% already, you might as well expand your base looking for more 1000x returns, and not cry too much about bad placements; this investing business has a significant opportunity cost risk which means you probably want to err on the side of putting some money in. If you're over 'great' returns, you can afford to do that, and should.

On the flip side, if you're under 'great' you probably want to figure out how to prune your choices away a bit first.


Everyone believes in their company, even the people who work at companies that turn out to be duds.

If 90% of your wealth exists only in the theoretical value of your pre-IPO stock, that's not a good balanced portfolio.


If there's a 10% chance that your business is forever upended, and if you don't react you'll be left in the dust is the right decision "90% chance we'll be good, no need to change plans" or "Hey we're making too much money to take any risks here, lets adapt to the 10% chance, and if the 90% comes to pass we'll just go back to the way it was"? I think it's pretty clear that tech CEOs made the right choice from investors perspective. I don't see how you can come to the conclusion that they failed to predict market conditions when you don't know what odds they came up with.

How do you know it's because of mistakes? Since when are markets totally predictable?

More than once inferior products and services get investor money and good ones fail to receive any funding.


"This is the future, and we are building the platform that will make it happen."

Yeah, keep telling yourself that. I know investors like to see confidence, but if you seriously believe your own hype, you'll be unprepared for failure. Chances are, you'll fail. Nothing to do with talent or how good your product is. Just luck. Learn humility. It will keep you from letting your guard down, and getting trampled on. And it will come in handy in case you fail.


This is 110% true: "Their way of doing things may get huge returns consistently...until it doesn't."

And most people will never fully understand that until it happens to them. Then you have this eye opening moment, and you understand.


I just don't see how that invalidates the anecdote. Because if you're investing "$100 million in a $1 billion company" you're probably aren't expecting a 20x return, not to mention a greater one. So that would suggest that there is something else going on, which is the greater point of the NYT article.

Now you bringing up a keyword: expectation.

I am starting to get sick of every argument that tries to defend these rediculous investment decisions these days. Currently everyone doing that is citing network effects, potential growth, the next big thing.. And for sure, if someone wants to invest his or her money, I will not judge that decision or the person itself.

But looking at the situation as a whole, so many decisions are made based on highly flawed expectations. A nice designed marketing page and multiple years without revenue? Here take some $m because <insert overestimation in here>.

Consider Airbnb.. I use it myself, but I am by no means locked in as a customer. Maybe it will crumble due to new/old regulation. Maybe too many weird people will start offering their spare-rooms, and it won't feel cool and hip anymore. Maybe hotel-chains react by offering better prices... There are so many maybes in that company alone.. simply believing in the network effect should not be the basis of a meaningful valuation.

I am highly sceptical about the current behavior of this part of the investment market. My concern lies not in the companies or the investors themself. They probably did hedge their risks. I just feel that the next bursting bubble will stretch far beyond the whatsapps and airbnbs out there.

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