Insider's Buy and Selling; Why They REALLY Buy or Sell


For almost a decade, we worked in the "Private Corporate Client" area of an international brokerage firm. "Private Corporate Client" is just another way of saying "Insider" as a majority of our clients were insiders selling their restricted shares and companies themselves doing buybacks/repurhcases. Because of that experience, we know why insiders REALLY SELL or BUY their company's shares. The actual reasons will probably surprise you.


We're not talking about illegal insider trading; that is, when someone with insider (non-public) information trades a stock based on that information. We're talking about when an officer, director, or other executive buys or sell shares.


We were the guys that would help these executives jump through the hoops they needed to so that they would be allowed to sell shares on the open market. There are quite a few hoops at that, but the most common are spelled out in SEC Rule 144 and Rule 144(k). Actual paper stock certificates are used when "restricted" shares are given to an insider and they actually are stamped "Restricted" in red on the certificate. We even had a CFO of a $Billion technology company pull up to our office, with his new speedboat being hauled behind his new SUV, to hand us a restricted stock certificate he wanted to sell that was worth several $Million. Yeah, those kind of "insiders".

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Rule 144 & Rule 144(k)


When you acquire restricted (unregistered) securities or hold control securities, you must file for an exemption from the SEC's registration requirements to sell restricted shares - or if they are registered, you must file a public notification of the sale. Rule 144 allows public resale of restricted and control securities if a number of conditions are met. This overview tells you what you need to know about selling your restricted or control securities. It also describes how to have a restrictive legend removed.


Some of the restrictions on the sales include how long that person has held those shares, the number of shares that can be sold in a specific period of time and even how those shares can be sold by the broker.


Restricted and Control Securities


Restricted securities are securities acquired in unregistered, private sales from the issuer or from an affiliate of the issuer. Investors typically receive restricted securities through private placement offerings, Regulation D offerings, employee stock benefit plans, as compensation for professional services, or in exchange for providing "seed money" or start-up capital. Rule 144(a)(3) identifies what sales produce restricted securities.


Control securities can be restricted or unrestricted but are always those held by an affiliate of the issuer. An affiliate is a person, such as a Director, the CEO & CFO, or large shareholder in a relationship of control with the issuer. Control means the power to direct the management and policies of the company in question, whether through the ownership of voting securities, by contract, or otherwise. Most often, that means the top executives.


If you are given restricted securities because you are an insider or were a seed investor, you almost always will receive a certificate stamped with a "restricted" legend. The legend is just a stamp that indicates that the securities may not be resold in the marketplace unless they are registered with the SEC or are exempted from the registration requirements.


There are plenty of technical terms and other pieces of information regarding these types of sales, but that's not important. As long as you understand the general restrictions, that's all you need to know more than 90% of investors do.


Should I Sell When The CEO Does?


In a few words... probably not.


There are many, many reasons why an insider like a CEO or a CFO will sell some of his or her shares. Maybe he is looking to purchase a new vacation home (or payoff his new boat like our CFO friend). Or, his son or daughter is heading off to college and he needs some cash for tuition and other expenses. Or, most commonly (in our experience), the stock has made a nice run and the executive is basically looking to diversify.


We've seen in many times where a CEO was there at the beginning. Maybe he had plenty of money before, but he's spent years, if not decades making the business into what it is today. During growth years, before the company became as big as it is now, that CEO may have been paid only pittance in actual cash compared to other CEOs in the same industry for those years. Instead of big paychecks, he was given restricted shares of stock as additional compensation. Doing that saved the company quite a bit of cash and gave that CEO a huge incentive to grow that company and increase the stock price. On paper, he might have $20 million in stock, but only a couple hundred thousand in actual cash or other investments from all of those years of work. If any of us were in that situation, the wise thing would be to sell at least a portion of those shares to diversify, buy an annuity, insurance, whatever. Let's say that CEO does not sell anything, and does not plan to until well after he retires, only when he needs it. Now, he's left and still has his $20 million in stock only. The next CEO is a crook and is caught with accounting irregularities. The stock plummets and bankruptcy is coming. The shares are now worthless. He should have sold some, no?


When an insider like a CEO sells shares (whether restricted or not), his broker needs to file a Form 144 with the SEC. The information on that form is what is made public and we all see online through financial websites like Yahoo that list insider sales. Rule 144 limits the number of shares that an insider can sell in a rolling 90 day period. The limit on the number of shares is tied to the average volume of the stock or the number of shares outstanding and varies from company to company and can even vary widely from one 90-day period to the next.


A wise broker will make ONE filing that mentions all of the shares that the CEO plans to sell in the next 90 days or less. That way, services like Yahoo Finance show just that one filing.


Many brokers have no experience with Rule 144 and make a filing each and every day that shares are sold listing just the amount sold. That's fine as far as disclosure laws go - but now Yahoo Finance might show 25 sales over 25 days where the CEO is selling around 10,000 shares each day for each of those 25 days.


Wouldn't it be less alarming as an investor if you saw that the CEO had just one filing for 250,000 and that was it? Psychologically, seeing 10,000 share sales over and over and over makes investors more likely to think the CEO is just cashing out and thinks the stock will drop.


So when you see smaller sales over and over and over by an executive, take a look at the history of his or her sales. It may be nothing more than a stupid broker filing each day instead of filing just once for the entire sell order.


If you see a CEO selling and those sales significantly drop the number of shares he holds, that makes even us nervous. That's a warning sign. We are also concerned when the insider uses an idiot for a broker who files for each and every sale. That insider is either not knowledgeable enough to use someone who knows how to minimize the impact of shareholders seeing all of those filings, or doesn't care enough to worry about the appearance of all of those sales. Shouldn't a CEO be better than that? We think so.