The most interesting part of this story to me is that Jason Fried is on the board of Groupon.
It does seem to clash with what 37signals discusses all the time regarding VC funding. I know that their main point is to fight the default mindset of going first to investors to fund you discovering what to really build, but nevertheless, a huge funding round whose main objective is to have some insiders cash out doesn't fit Jason Fried's perceived philosophy. (granted, DHH might be the more vocal of the two about it)
In my opinion, this is a perfect example of what's currently very broken with the VC/funding model. Groupon is wildly successful, wildly profitable, and yet it's investor can't get paid anything without the whole company having to do this weird funding rigamarole.
In the old days they would have just gone public and everybody would be happy. But with the latest regulations nobody wants to do that anymore. And they don't want to sell their company, for good reason. So they're stuck.
What there really needs to be is some accepted, pre-defined method for investors to profit from a successful company's cash receipts. That would simplify this whole process, but I don't know how feasible that is.
It's not keeping companies from going public as much as being a big enough pain and expense to make methods like Groupon's more desirable.
1. Going public now requires months and months more of extra accounting due dilligence, audits, etc. that will cost millions upon millions of dollars.
2. Now that you're a public company most of the executives and especially the CFO are severely, criminally liable for any accounting fraud that happens in the organization regardless of whether they knew anything about it.
SOX was a reaction (over-reaction) to the Enron and Worldcom disasters where accounting fraud took down huge public companies, destroyed thousands of jobs, and cost billions of dollars. And the executives just claimed they didn't know anything when they obviously did.
So now theres extra audits, execs are liable regardless, and nobody wants to go public anymore.
Plus nobody wants to IPO in this economy anyway.
You gotta have some solution where investors have something of some actual value at some point or you're going to see investment go away once they all decide there's no upside.
Compare to a sale of stock, which is only taxed at 24.3%, and you can start to see some of the advantages.
Another advantage includes being able to capitalize on a multiple of your revenue/profit, instead of on a 1X every year, as well as continuing to put the company's revenue towards growth instead of cashing it all out.
I understand the voting/bankruptcy rights of stock, but for most retail investors, it seems to me that holding shares of Apple is really just a large Ponzi-scheme (this has probably been debated on here ad nauseum).
And that's just the incentive for the little guy who's an outside investor. Imagine now you're a big guy with a lot of financial clout, and inside connections, especially as far inside as being on the board or one of the executives. You not only are incented to cause distortions to the stock price, regardless of merit, but you also have greater power over the "upstream" numbers (how to define profit, when to book profits/costs, etc.) and over the media presence and general public's perception of the company. Greater potential upside plus greater power to manipulate, is a recipe for bad things.
Taxes/fees/whatever are taken out when money changes hands. Whether it moves from one individual to another, or between an individual and a company, or between two companies, etc. It doesn't matter. It's just "single" taxation. But there might be a series of them with N hops.
Consider this: consumer A pays out money to buy some good from company B. Out of that money, some is siphoned off in the form of sales taxes. The company gets the balance of that. Company pays some portion of their earnings in taxes. Company also pays some portion of their revenue to their employees. Out of the money paid by the company to their employee, some is taken out as tax. Employee gets the money. Out of that money, he uses some of it to buy some product. Out of that total purchase price he pays, some is taken out in sales taxes. And so on, and so on. Repeat with other sorts of transactions and money flows. Thus, there is no "double taxation" just taxation. If you argue there is double taxation, then, in reality, there is also triple taxation and quadruple taxation and infinity taxation.
Double taxation is code for "I just don't like that particular tax and want it reduced or eliminated". It is not a factually valid criticism in and of itself, by my reasoning.
interestingly, the total federal rate paid on dividends = 1-(.65*.85) = 44.75%. I wonder how this compares to the total individual income tax rate (including soc sec/medicare/etc) and at what points in the individual income tax schedule is one rate more favorable than the other.