Startup Toolbox

Business and Legal Notes, Mostly

Why Deferred Salaries Don’t Work for Startup Founders

Jay Parkhill September 4th, 2008

One of the toughest conversations I have with many startup founders is about salaries.  Founders may come from larger companies that pay them an annual salary and the idea of getting *no* cash for a significant period of time is really hard to wrap one’s mind around.  The argument goes something like this:

“I make $X currently, I know I am worth that much and I really need to get the cash.  I can defer collecting it for a little while, but I need to catch up at some point.”

My humble suggestion is always the same- don’t think about it that way.  You are building equity in a new business.  The equity is your return.  You are unlikely to see your “deferred” salary repaid in that way, so make sure you have enough stock in the business to give the upside you need and work toward making that worth something.

There are really two alternatives to this, neither of which is feasible: accruing a hypothetical salary to be repaid when some large bundle of cash hits the company’s accounts through financing or sales efforts, and taking stock in lieu of cash.

The Extra Cash Theory

The repayment on filling the coffers approach is based on the false premise that at some point there will be “extra cash” available.  This never happens.  Investors put money into a business in order to build structures that will take the business down the road.  Seeing their cash go straight through a company’s bank account is anathema- except when a founder has actually put in cash without getting stock for it.

The revenue argument is probably even worse.  Revenue is hard to come by and most businesses don’t see enough of it to justify paying back salaries on top of current ones and other business expenses.  The idea of generating enough revenue to cover accrued/deferred salaries is a fantasy in almost all cases.

Stock for Salaries

The stock-for-salary proposal is actually much worse than the extra cash idea.  What many founders don’t realize is that the IRS treats stock in that case exactly the same as cash and taxes it at the same rate.  If a founder accrues $100k in salary and collects it in stock she still has $100k in income to report.

The problem is that she has $100k worth of illiquid stock, a tax bill of $35k or so and no cash to pay the taxes.  This is not a happy situation for anyone.

No Deferral, No Salary, Just Stock

The way out of the dilemma is to give up on the idea of taking much cash out of the business in the early going.  Buy your founder stock (for cash!) at a very low price when you start the business.  That is what you get instead of a salary, so be mindful of unnecessary dilution (no “advisory” options to friends and relatives) and work on making that stock as valuable as you possibly can.  You may not see much cash for a couple of years or more, but if you are lucky the stock will more than compensate for the sacrifices made in the early days.

Slow Steps Into the Digital Age at the IRS

Jay Parkhill February 20th, 2008

For those who have never filed form 1099 before, one copy (red) goes to the IRS and another (black) goes to the independent contractor who provided services to a business. Apparently the reason for this is that the IRS’s computers scan the filings, and they can only read forms printed with red ink.

One can’t download the fileable form, because the shade of red must be very specific and a normal color printer can’t be trusted to get it right. One must have the forms mailed out or buy them from an office supply store.

About.com tells me that the Social Security Administration updated its systems to accept black copies of form W-2, but the IRS has changed its systems twice without adding this magical ability.

The IRS does allow 1099s to be filed electronically. This is a great step forward- it fairly leapfrogs the whole download/print/mail correct-color routine.

*However*, while thousands of businesses everywhere have figured out how to create online forms viewable and editable in any web browser, AND have worked out a way to let consumers create accounts online in minutes (if not seconds), the IRS is not quite there.

So in order to conveniently file my 1099s online, I must first mail in a form to the IRS, receive a Transmitter Control Code back by mail, and then download and install the IRS’s special form-creation software.

Identity theft and fraud are certainly big concerns so I can understand the need to verify identity before setting up accounts. Putting documents in the mail is not a remedy here though (the IRS should ask Network Solutions about Stephen Michael Cohen and Sex.com on this point).

The IRS has a huge job managing millions of accounts. They are certainly correct to be careful, and kudos to them for getting on the e-filing program. My wish, though, is that after Microsoft takes over Yahoo and drives away key employees, that the IRS will see an opportunity to pick up some Internet expertise. Yahoo has great e-commerce software. Get some of the engineers behind it working on IRS e-file programs for all kinds of filing.