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samclearman

85 karma · joined March 19, 2009

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samclearman··on Stripe faces $3.5B tax bill as employees' shares expire
Not sure what you mean by "should" here, but the IRS definitely considers it to be a gain that you have to pay taxes on, regardless of whether you can sell the shares.
samclearman··on Stripe faces $3.5B tax bill as employees' shares expire
RSU's are taxed on vesting, so it would be worse than options if anything.

Best are options with early exercise, but they're still not perfect (you have a possibly significant upfront cost to exercise them).

Really they should just change the AMT rules.

samclearman··on Stripe faces $3.5B tax bill as employees' shares expire
Yes, it's common. They'll say that it's because they don't want unapproved investors on their cap table, which I guess is reasonable, but obviously the main reason is "because they can".
samclearman··on Stripe faces $3.5B tax bill as employees' shares expire
Because the system is crazy, but it only affects early employees of successful startups so there's no political will to fix it.
samclearman··on Stripe faces $3.5B tax bill as employees' shares expire
In this case, the way it works is:

1. You exercise your options, for a paper gain of millions of dollars

2. However, you can't actually sell the shares (there are likely contractual restrictions on selling them, and even if not, there's not a liquid market)

3. So you have to pay millions of dollars of taxes even though your cash flow is zero.

And before you say "but they're ISOs", there's no such thing as ISO's under AMT so it doesn't help at all.

samclearman··on I won’t buy ebooks anymore
https://medium.com/@samclearman/stop-paying-for-e-books-and-...
samclearman··on Old Paris Is No More
The article is about the 18th and 19th centuries.
samclearman··on Scale (YC S16) Raises $100M from Accel and Founders Fund at $1B Valuation
I work at Scale - I've met a bunch of people that work on our platform, and seeing the impact that it's had on their lives is actually a huge source of inspiration to me. There's a writeup highlighting some of their stories at https://scale.com/blog/positive-externalities - based on my personal experience, I can say that it's not bullshit.
samclearman··on Sonder Raises $135M to Turn Airbnb Apartments into Hotels
Most Americans have spare bedrooms for when guests visit. You could have your guests stay at a hotel but typically that will be really far from your home which sucks for everybody. Having Sonder or Airbnb style short term rentals distributed throughout cities could allow people to live in smaller apartments, eliminating bedrooms that sit unused most nights creating more space for everybody.

To be clear I'm not talking about the model of renting out your spare bedroom on Airbnb because nobody actually wants to do that. I'm talking about full time airbnb studios / 1BR's obviating the need for guest bedrooms.

samclearman··on Disney acquires own streaming facilities, will pull Netflix content
Pricing is per household, so a family of four spends the same as an single individual.
samclearman··on Disney acquires own streaming facilities, will pull Netflix content
Maybe you never used to spend more than $10/month on video, but most Americans have been spending an order of magnitude more than that.
samclearman··on Disney acquires own streaming facilities, will pull Netflix content
A la carte TV pricing was always a stupid idea. What people really wanted was cheaper pricing, which is of course not going to happen.
samclearman··on Soti – A $1B firm built in a basement
Top students getting offers in California are getting 150k USD minimum (including equity and bonus).
samclearman··on Snap falls to IPO price
The other, probably more important, innovation was that you have to take the picture at the same time as you send it - no loading from the camera roll.
samclearman··on How Craigslist Makes Money
Well spotted.
samclearman··on Cracking the Mystery of Labor's Falling Share of GDP
Yup and the solution is simple, a land value tax as close to 100% as is practical.
samclearman··on Focus by Firefox, a Content Blocker for iOS
Probably because Firefox is a well known brand and Mozilla isn't.
samclearman··on Uber Raises Funding at $62.5B Valuation
Presumably the deal terms include a liquidation preference and thus the implied valuation is essentially horseshit.
samclearman··on A Decade-Old Gag Order, Lifted
This stuff is much worse than NSA data collection. Gag orders are evil, and secret courts are even worse. I really wish people would stop worrying about government surveillance - who cares what people know about you? - and start worrying about this instead.
samclearman··on Oakland releases months’ worth of license plate reader data
No. All the data that they use is self-reported (when you sign up for health insurance, they ask you if you smoke, etc).
samclearman··on China Has a $1.2 Trillion Ponzi Finance Problem
This article is utterly useless without comparisons to the equivalent numbers in other major economies.
samclearman··on Man tells devastating story of his dad's death at an Airbnb
This kind of thing is an advantage of Airbnb. Our litigious society has resulted in overly sanitized public spaces - no hotel would have a rope swing on a tree because of safety/liability concerns. We need to realize that it is not worth ruining everything to marginally improve safety.
samclearman··on Mr. Buffett on the Stock Market (1999)
Actually a bigger problem is that his advice is just straight up hard to follow. If correctly valuing public companies were easy, the market would be a lot less volatile.
samclearman··on Mr. Buffett on the Stock Market (1999)
... Since then interest rates went to zero and corporate profit as percent of GDP went to 10. I guess that's why he doesn't like to try to predict the market :)
samclearman··on Yield of 0% a First at 3-Month Treasury-Bill Sale
Given that a US default would likely cause the collapse of the US financial system and possibly the entire world's financial system, it makes perfect sense to trust the US government's credit over that of any bank.
samclearman··on Lens Blur in the new Google Camera app
According to the article, and my own experience with google's version, it's good enough for simple portraits. Since most photos, and close to 100% of photos anybody actually cares about, are portraits that makes it a pretty useful feature.
samclearman··on Reddit’s empire is founded on a flawed algorithm
If he has some justification for the formula to be as it is, why hasn't he shared it with us?
samclearman··on Reddit’s empire is founded on a flawed algorithm
How does it make any sense to multiple the date by the sign of the score? It's true that it only matters when the score is negative, and so it doesn't really affect much in practice, but the code is clearly a typo.
samclearman··on Blink: A rendering engine for the Chromium project
No way to disable tabs (in particular the default "open in new tab" behavior) in Chrome.
samclearman··on No More Internet
"We have the capabilities of sifting through bleeding edge information that shapes our lives on a daily basis with the internet."

What exactly are you talking about here? Of the top of my head I can't thank of anything on the internet that isn't a total waste of time, with two exceptions: - looking up specific information (programming docs, the first 10 minutes on wikipedia, etc) - browsing the arXiv

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