Class of shares specifically for retirement accounts with contribution limits
"The fair price of a stock is the present value of its future payments.  That means the stock you have described would have a ""fair"" value that is quite high and you wouldn't be able to put much of it in your 401(k) or IRA. The IRS requires that ""fair value"" be used for calculating the value of IRA and 401(k) assets. Of course, if the stock is not publicly traded, then there's not an obvious price for it.  I'm sure in the past people have said they spent a small amount of money for assets that are actually worth much more in order to get around IRS limits.  This is illegal. The IRS can and sometimes will prosecute people for this. In order to address abuses of the system by inclusion of hard to value assets in retirement accounts, the IRS has additional reporting requirements for these assets (nonpublic stock, partnerships, real estate, unusual options, etc.) and those reporting requirements became more stringent in 2015.  In other words, they are trying to clamp down on it. There are also likely problems with prohibitions against ""self-dealing"" involved here, depending on the specifics of the situation you are describing."
The first question is essentially asking for specific investment advice which is off-topic per the FAQ, but I'll take a stab at #2 and #3 (2) If my 401k doesn't change before I leave my job (not planned in the   near future), I should roll it over into my Roth IRA after I leave due   to these high expense ratios, correct? My advice is that you should roll over a 401K into an IRA the first chance you get (usually when you leave the job). 401K plans are NOTORIOUS for high expense ratios and why leave your money in a plan where you have a limited choice of investments anyway versus a self-directed IRA where you can invest in anything you want? (3) Should I still max contribute with these horrible expense ratios? If they are providing a match, yes. Even with the expense ratios it is hard to beat the immediate return of an employer match.  If they aren't matching, the answer is still probably yes for a few reasons: You already are maxing out your ability to contribute to sheltered accounts, so assuming you still want to sock away that money for retirement, the tax benefits are still valuable and probably offset the expense ratios. Although you seem to be an exception, it is hard for most people to be disciplined enough to put money in a retirement account after they have it in their hands (versus auto-deduction from paychecks). "I am not 100% sure, but I think the answer is this:  You can't max out both.  You could theoretically max out the SIMPLE IRA ($11,500) and then contribute $4,000 to your 401k, but your total can't exceed the 401k limit of $16,500.  This also means you could max out your 401k at $16,500, but you couldn't contribute anything to the SIMPLE IRA.  Note that no matter what, you can't contribute more than $11,500 to your SIMPLE IRA. (Note that this is all independent from your Traditional or Roth IRA, which are subject to their own limits, and not affected by your participation in employer-sponsored plans.) As I understand it, a 401k and a SIMPLE IRA both fall under the umbrella of ""employer-sponsored plans"".  Just like you can't max out two 401k's at two different employers, you can't do it with the 401k and the SIMPLE IRA.  The only weird thing is the contribution limit differences between SIMPLE IRA and 401k, but I don't think the IRS could/would penalize you for working two jobs (enforcing the lower SIMPLE IRA limit for all employer-sponsored retirement accounts). You should probably run the numbers, factoring in the employer match, and figure out which account-contribution scenario makes the most financial sense for you.  However, I'm not sure how the employer match helps you when you're talking about a small business that you own/run.  You may also want to look at how the employer match of the SIMPLE IRA affects the taxes your business pays. Disclaimer #1:  I couldn't find a definitive answer on your specific scenario at irs.gov.  I pieced the above info from a few different ""SIMPLE IRA info"" sites.  That's why I'm not 100% sure.  It seems intuitively correct to me, though.  Does your small business have an accountant?  Maybe you should talk to him/her. Disclaimer #2:  The $ amounts listed above are based on the IRS 2010 limits." You are in the perfect window for making an IRA contribution. The IRS allows you to make IRA contributions for last year until tax day. So you know that for 2014 you didn't have access to a 401K at work. You want to avoid making a deductible IRA contribution for this year (2015) until you are sure that you wont have a 401K at work this year. Take your time and decide if the detectible IRA or the Roth works best for your situation. Having a IRA now will be good becasue you have many years for it to grow. Keep in mind that it is not unusual to have multiple retirement accounts: Current 401K; rolled over into a IRA;  Roth IRA... Each has different rules, limits, and benefits. There is no reason to pick one way of investing for retirement becasue you never know if the next employer will have the type of plan you like. I am assuming that your spouse, if you are married, doesn't have access to a 401K; otherwise you would have to consider the applicable limits. Congrats! That's a solid accomplishment for someone who is not even in college yet. I graduated college 3 years ago and I wish I was able to save more in college than I did. The rule of thumb with saving: the earlier the better.  My personal portfolio for retirement is comprised of four areas: Roth IRA contributions, 401k contributions, HSA contributions, Stock Market One of the greatest things about the college I attended was its co-op program. I had 3 internships - each were full time positions for 6 months. I strongly recommend, if its available, finding an internship for whatever major you are looking into. It will not only convince you that the career path you chose is what you want to do, but there are added benefits specifically in regards to retirement and savings. In all three of my co-ops I was able to apply 8% of my paycheck to my company's 401k plan. They also had matching available. As a result, my 401k had a pretty substantial savings amount by the time I graduated college. To circle back to your question, I would recommend investing the money into a Roth IRA or the stock market. I personally have yet to invest a significant amount of money in the stock market. Instead, I have been maxing out my retirement for the last three years. That means I'm adding 18k to my 401k, 5.5k to my Roth, and adding ~3k to my HSA (there are limits to each of these and you can find them online). Compounded interest is amazing (I'm just going to leave this here... https://www.moneyunder30.com/power-of-compound-interest). Thanks for your reply. I’m not familiar with the term “Held-For-Trading Security”. My securities are generally held as collateral against my shorts. To clarify, I am just trying to track the “money in” and “money out” entries in my account for the shorts I write. The transaction is relatively straight forward, except there is a ton of information attached! In simple terms, for the ticker CSR and short contract CSRUQ8, the relevant entries look something like this: There are no entries for expiries. I need to ensure that funds are available for future margin calls and assignments. The sale side using covered calls is as involved. Is investing in a Roth retirement account only better if you will be in a higher    tax bracket in retirement? If you are pushing up against the contribution limits, a Roth account may allow you to save more money in tax-advantaged accounts. In your example, you are putting $100 pre-tax in a traditional account vs $85 post-tax in a Roth account. But if there are limits, and the limits are the same for traditional or Roth accounts (as they currently are for US 401(k) accounts), you can effectively put more into a Roth account, where the limit applies to the post-tax amount, than a traditional account, where the limit applies to the pre-tax amount. If so, is there any case in which a traditional retirement account is better than a Roth account? It is smart to have some money in a traditional account, because the first amount of money you earn or withdraw each year (up to the standard deduction) is taxed at 0%, which is probably less than your current rate. And the next bit of money is taxed at only 10%, which may also be less than your current marginal rate. Of course, things may change by the time you retire, but it is probably safe to assume that we will still have some kind of progressive (income bracketed) tax structure. "IANAL, but no, this is not sound legal advice. There are a few things that stick out to me as fishy. First off: you are calculating the 3% safe-harbor on the 2017 compensation limit of $270k, but limiting yourself to $53k in total contributions which is the 2016 limit. It's hard to tell what tax year you're working in here. If you're planning for 2017, fine, but if you're wrapping up 2016 then you need to use 2016 limits. Secondly (and this is something I think your counsel should know already): you don't take Employer contributions out of gross wages (box 1) on the W-2. They aren't even reported there in the first place! With your base scenario the 2 employees' W-2s would look like this: Employee A's W-2 Gross Wages (box 1) = 280,000 - 14,966.67 = 265,033.33 Employee B's W-2 Gross Wages (box 1) = 280,000 - 0 = 280,000 Elective deferrals are the only thing that should come out of wages. Not the SH 3% or Match. Thirdly: Retirement Plan expenses really aren't an ""above the line"" expense. They are not included in cost of goods sold. Even if you establish a ""pool"" for that expense, it's still not a direct cost attributable to the production of whatever your company sells. Also: Employee B should not have to contribute to the retirement account of Employee A! The only situation I can see where Employee A and B would be required to fund the match equally, were if Employee A & B are both 50% owners and the company has no funds of its own with which to fund the match. The company has obligated itself to fund the match, and if the company doesn't have any money then the money still has to come from somewhere (ie. the owners pony up more funds for the match they promised their employees, it just happens that the employees are also the owners). Even in this situation though, I still stand behind my first 3 points." There are ETFs listed on the Brazilian stock market. Specifically there is one for S&P500 - SPXI11, which might fulfill your requirements, though as one commenter has observed, it doesn't answer your original question.