At Vanguard, can I transfer shares from regular investment account to a Roth IRA?
No, IRA contributions can only be made in the form of cash (rollovers and conversions are different). You'd have to sell the investments in your taxable account, incurring capital gains or losses, then transfer the proceeds to your IRA in cash. Note that the amount you can transfer is subject to the limits on how much one can contribute to the IRA each year. You could look into Vanguard Target Retirement funds, which have a lower $1,000 minimum investment, or Vanguard ETFs. Since you are paying taxes on the distributions from your mutual funds anyway, instead of reinvesting the distributions back into the mutual funds, you could receive them as cash, then contribute them to your Roth IRA once you are able to open one.
When you pick a company for your IRA, they should have information about rolling over funds from another IRA or a 401K. They will be able to walk you through the process. There shouldn't be a fee for doing this. They want your money to be invested in their funds. Once your money is in their hands they are able to generate their profits.  You will want to do a direct transfer. Some employers will work with the investment companies and send the funds directly to the IRA. Others will insist on sending a check to you. The company that will have your IRA should give you exact specifications for the check so that you won't have to cash it. The check will be payable to you or the IRA account. The IRA company will have all the details. Decide if you will be converting non-Roth to Roth, before doing the rollover. "Your contributions must come from ""compensation"". Quoting IRS Publication 590 on IRAs, ""Generally, compensation is what you earn from working."" So it is unlikely that your stock sale proceeds, if they're your sole source of income, can be used to fund your IRA. If you do have W-2 income, or self employment income, you can use the proceeds of a stock sale to fund an IRA. The IRS doesn't care where the exact dollars that go into the IRA come from, only that you earned (from working) at least as much as you contributed." Why shouldn't I just keep my money in the savings account and earn the same amount (both accounts have the same APY in this case)? I will assume that you are transferring money from your savings account into a Traditional IRA and deducting the contribution from your income.  While you may think that the money that is being transferred is yours already -- it is sitting in your savings account, for Pete's sake! -- you are deducting that amount in getting to your taxable income, and so you are effectively contributing it from current income and not paying taxes on the amount contributed. So, consider the same amount of money sitting in your savings account versus the same amount of money sitting in your Traditional IRA account. While you will earn the same amount of interest in both accounts, you will have  to pay taxes each year on the interest earned in the savings account. You might  choose, as most people do, to not take money out of the savings account to pay theses taxes but just pay them from ready cash/checking account/current income etc., or these taxes might just reduce the refund that you will getting from the IRS and your State income tax authority, but in either case, you have paid taxes on the interest earned in your non-IRA savings account, and of course, long ago, you also paid taxes on the original amount in the non-IRA savings account.  So, if you take any money out of the non-IRA savings account, you don't pay any taxes on the amount withdrawn except possibly for the interest earned from January 1 till the date of withdrawal (which you are paying from ready cash). On the other hand, consider the Traditional IRA. The original deposit was not taxed in the sense that you got a deduction (reduced tax or increased refund) when you made the contribution. The annual interest earned was not taxed each year either.  So when you make a qualified withdrawal (after age 59.5 or by meeting one of the other exceptions allowing withdrawal before age 59.5), you are taking money on which you have not paid any taxes at all, and the IRS wants its cut.  The money withdrawn is taxable income to you. Furthermore, the money withdrawn is not eligible for any kind of favorable treatment such as having it count as qualified dividends or as long-term capital gains even if your IRA was invested in stocks and the money in the account is all qualified dividends or long-term capital gains.  If you make an unqualified withdrawal, you owe a penalty (technically named an excise tax) in addition to income tax on the amount withdrawn. If you are investing in a Roth IRA, you will not be getting a deduction when you make the contribution, and qualified withdrawals are  completely tax-free, and so the answer is completely different from the above. What you want is a position transfer, likely by ACATS.   This is a transfer from one IRA to another without having to liquidate positions to do so.  In effect, the brokerage firm is just transferring records from your existing IRA to your new IRA.  You will need to watch out to make sure your new IRA account can hold your positions for this to work.  For example, some brokerages allow you to hold fractional shares but others don't.  (The fractional share amounts would be sold automatically prior to transfer.)  Another example might be different fund families could be allowed between different brokerages. The general process is open your new IRA account, initiate the ACATS xfer from your new account, your old IRA account brokerage sends the positions over, and after a week or so your new IRA brokerage notifies you that everything is transferred. I've switched IRAs a couple times via this mechanism and never been charged a fee, but I've always stuck with the larger brokerages like Fidelity, TD Ameritrade, and Interactive Brokers. This is really an extended comment on the last paragraph of @BenMiller's answer. When (the manager of) a mutual fund sells securities that the fund holds for a profit, or receives dividends (stock dividends, bond interest, etc.), the fund has the option of paying taxes on that money (at corporate rates) and distributing the rest to shareholders in the fund, or passing on the entire amount (categorized as dividends, qualified dividends, net short-term capital gains, and net long-term capital gains) to the shareholders who then pay taxes on the money that they receive at their own respective tax rates. (If the net gains are negative, i.e. losses, they are not passed on to the shareholders. See the last paragraph below).  A shareholder doesn't have to reinvest the distribution amount into the mutual fund: the option of receiving the money as cash always exists, as does the option of investing the distribution into a different mutual fund in the same family, e.g. invest the distributions from Vanguard's S&P 500 Index Fund into Vanguard's Total Bond Index Fund (and/or vice versa). This last can be done without needing a brokerage account, but doing it across fund families will require the money to transit through a brokerage account or a personal account. Such cross-transfers can be helpful in reducing the amounts of money being transferred in re-balancing asset allocations as is recommended be done once or twice a year. Those investing in load funds instead of no-load funds should keep in mind that several load funds waive the load for re-investment of distributions but some funds don't: the sales charge for the reinvestment is pure profit for the fund if the fund was purchased directly or passed on to the brokerage if the fund was purchased through a brokerage account. As Ben points out, a shareholder in a mutual fund must pay taxes (in the appropriate categories) on the distributions  from the fund even though no actual cash has been received because the entire distribution has been reinvested. It is worth keeping in mind that when the mutual fund declares a distribution (say $1.22 a share), the Net Asset Value per share drops by the same amount (assuming no change in the prices of the securities that the fund holds) and the new shares issued are at this lower price. That is, there is no change in the value of the investment: if you had $10,000 in the fund the day before the distribution was declared, you still have $10,000 after the distribution is declared but you own more shares in the fund than you had previously. (In actuality, the new shares appear in your account a couple of days later, not immediately when the distribution is declared).  In short, a distribution  from a mutual fund that is re-invested leads to no change in your net assets, but does increase your tax liability. Ditto for a distribution that is taken as cash or re-invested elsewhere. As a final remark, net capital losses inside a mutual fund are not distributed to shareholders but are retained within the fund to be written off against future capital gains. See also this previous answer  or this one. "From the way you frame the question it sounds like you more or less know the answer already. Yes - you can make a non-deductable contribution to a traditional IRA and convert it to a Roth IRA. Here is Wikipedia's explanation: Regardless of income but subject to contribution limits, contributions can be made to a Traditional IRA and then converted to a Roth IRA.[10] This allows for ""backdoor"" contributions where individuals are able to avoid the income limitations of the Roth IRA. There is no limit to the frequency with which conversions can occur, so this process can be repeated indefinitely. One major caveat to the entire ""backdoor"" Roth IRA contribution process, however, is that it only works for people who do not have any pre-tax contributed money in IRA accounts at the time of the ""backdoor"" conversion to Roth; conversions made when other IRA money exists are subject to pro-rata calculations and may lead to tax liabilities on the part of the converter. [9] Do note the caveat in the second paragraph. This article explains it more thoroughly: The IRS does not allow converters to specify which dollars are being converted as they can with shares of stock being sold; for the purposes of determining taxes on conversions the IRS considers a person’s non-Roth IRA money to be a single, co-mingled sum. Hence, if a person has any funds in any non-Roth IRA accounts, it is impossible to contribute to a Traditional IRA and then “convert that account” to a Roth IRA as suggested by various pundits and the Wikipedia piece referenced above – conversions must be performed on a pro-rata basis of all IRA money, not on specific dollars or accounts. Say you have $20k of pre-tax assets in a traditional IRA, and make a non-deductable contribution of $5k. The account is now 80% pre-tax assets and 20% post-tax assets, so if you move $5k into a Roth IRA, $4k of it would be taxed in the conversion. The traditional IRA would be left with $16k of pre-tax assets and $4k of post-tax assets." Unless I'm misunderstanding something, you don't need to move your assets into a new type of account to accomplish your goal of letting your money grow in a low cost vanguard index fund. Simply reallocate your assets within the Inherited IRA. If the brokerage you're in doesn't meet your needs (high transaction fees, no access to the Vanguard funds you're interested in) you can always move to a low cost brokerage. The new brokerage can help you transfer your assets so that the Inherited IRA remains intact. You will not have a tax burden if you do this reallocation and you'll be able to feel good about your diversification with a low cost index fund. You will, however, have to pay taxes on your RMD. Since you're young I can't imagine that your RMD will be greater than the $5k you can invest in a Roth IRA. If it is, you can open a personal account and keep letting the the money grow. You can't actually transfer shares directly unless they were obtained as part of an employee share scheme - see the answers to questions 19 and 20 on this page: http://www.hmrc.gov.uk/isa/faqs.htm#19 Q. Can I put shares from my employee share scheme into my ISA? A. You can transfer any shares you get from into a stocks and shares component of an ISA without having to pay   Capital Gains Tax - provided your ISA manager agrees to take them. The   value of the shares at the date of transfer counts towards the annual   limit. This means you can transfer up to £11,520 worth of shares in the tax   year 2013-14 (assuming that you make no other subscriptions to ISAs,   in those years). You must transfer the shares within 90 days from the day they cease to   be subject to the Plan, or (for approved SAYE share option schemes) 90   days of the exercise of option date. Your employer should be able to   tell you more. Q. Can I put windfall or inherited shares in my ISA? A. No. You can only transfer shares you own into an ISA if they have   come from an employee share scheme. Otherwise, the ISA manager must   purchase shares on the open market. The situation is the same if you have shares that you have inherited.   You are not able to transfer them into an ISA. Immediately move your Roth IRA out of Edward Jones and into a discount broker like Scottrade, Ameritrade, Fidelity, Vanguard, Schwab, or E-Trade.  Edward Jones will be charging you a large fraction of your money (probably at least 1% explicitly and maybe another 1% in hidden-ish fees like the 12b-1).  Don't give away several percent of your savings every year when you can have an account for free.  Places like Edward Jones are appropriate only for people who are unwilling to learn about personal finance and happy to pay dearly as a result.  Move your money by contacting the new broker, then requesting that they get your money out of Edward Jones.  They will be happy to do so the right way.  Don't try and get the money out yourself. Continue to contribute to your Roth as long as your tax bracket is low.  Saving on taxes is a critically important part of being financially wise.  You can spend your contributions (not gains) out of your Roth for any reason without penalty if you want/need to.  When your tax bracket is higher, look at traditional IRA's instead to minimize your current tax burden.  For more accessible ways of saving, open a regular (non-tax-advantaged) brokerage account. Invest in diversified and low-cost funds.  Look at the expense ratios and minimize your portfolio's total expense.  Higher fee funds generally do not earn the money they take from you. Avoid all funds that have a nonzero 12b-1 fee. Generally speaking your best bet is buying index funds from Fidelity, Vanguard, Schwab, or their close competitors.  Or buying cheap ETF's.   Any discount brokerage will allow you to do this in both your Roth and regular accounts.  Remember, the reason you buy funds is to get instant diversification, not because you are willing to gamble that your mutual funds will outperform the market.  Head to the bogleheads forum for more specific advice about 3 fund portfolios and similar suggested investment strategies like the lazy portfolios.  The folks in the forums there like to give specific advice that's not appropriate here. If you use a non-tax-advantaged account for investing, buy and sell in a tax-smart way.  At the end of the year, sell your poor performing stocks or funds and use the loss as a tax write-off.  Then rebalance back to a good portfolio.  Or if your tax bracket is very low, sell the winners and lock in the gains at low tax rates.  Try to hold things more than a year so you are taxed at the long-term capital gains rate, rather than the short-term. Only when you have several million dollars, then look at making individual investments, rather than funds.  In a non-tax-advantaged account owning the assets directly will help you write off losses against your taxes.  But either way, it takes several million dollars to make the transactions costs of maintaining a portfolio lower than the fees a cheap mutual/index fund will charge. You can buy stocks in the IRA, similarly to your regular investment account. Generally, when you open an account with a retail provider like TDAmeritrade, all the options available for you on that account are allowable. Keep in mind that you cannot just deposit money to IRA. There's a limit on how much you can deposit a year ($5500 as of 2015, $6500 for those 50 or older), and there's also a limit on top of that - the amount you deposit into an IRA cannot be more than your total earned income (i.e. income from work). In addition, there are limits on how much of your contribution you can deduct (depending on your income and whether you/your spouse have an employer-sponsored retirement plan). From your first link: IRS.gov: IRA One-Rollover-Per-Year-Rule IRA One-Rollover-Per-Year Rule Beginning in 2015, you can make only one rollover from an IRA to   another (or the same) IRA in any 12-month period, regardless of the   number of IRAs you own (Announcement  2014-15 and Announcement   2014-32). The limit will apply by aggregating all of an individual’s   IRAs, including SEP and SIMPLE IRAs as well as traditional and Roth   IRAs, effectively treating them as one IRA for purposes of the limit. They are limiting your ability to roll over money from an IRA to an IRA. You are looking to go from a 401K to an IRA. That is fine. The idea was that some people were taking all money from their IRA, using it for almost 60 days, then putting it back into an IRA. Thus getting a sort of short term loan. They could do this multiple times in a year. The direct trustee-to-trustee transfer are exempt from the once per year rule because the money is never in your possession.  Moving money from a 401K/403b/TSP plan from your former employer to an IRA or Roth IRA is fine, and isn't limited to once per year. You cannot just transfer or rollover from a traditional to a Roth IRA, because they are taxed differently.  You'd have to do a distribution from your traditional (which will be taxed and possibly penalized, depending on your income and age), and a contribution to your Roth (which is limited based on annual contributions to all your IRAs). A conversion is not limited by dollar amount (unless you must take an RMD... required distributions may not be converted).  There is no income limit for 2010 and beyond (previously $100k MAGI), and there are no penalties.  However, all you must pay tax on all untaxed dollars - this means the original contributions as well as the growth. It all depends on the size of your IRA, your investment options, and your expected tax bracket at retirement.  Traditional IRA distributions are considered income for the year, while Roth distributions are not. Edited in response to JoeTaxpayer's comment and OP Tim's additional question. To add to and clarify a little what littleadv has said, and to answer  OP Tim's next question: As far as the IRS is concerned, you have at most one Individual Retirement Account of each type (Traditional, Roth) though the money in each IRA can be invested with as many different custodians (brokerages, banks, etc.) and different investments as you like. Thus, the maximum $5000 ($6000 for older folks) that you can contribute each year can be split up and invested any which way you like, and when in later years you take a Required Minimum Distribution (RMD) from a Traditional IRA, you can get the money by selling just one of the investments, or from several investments; all that the IRS cares is that the total amount that is distributed to you is at least as large as the RMD. An important corollary is that  the balance in your IRA is the   sum total of the value of all the investments that various custodians are holding   for you in IRA accounts. There is no loss in an IRA until every penny has been withdrawn from every investment in your IRA and  distributed to you, thus making your IRA balance zero.  As long as you have a positive balance, there is no loss: everything has to come out. After the last distribution from your Roth IRA (the one that empties your entire Roth IRA, no matter where it is invested and reduces your Roth IRA balance (see definition  above) to zero), total up all the amounts that you have received as  distributions from your Roth IRA. If this is less  than the total amount of money you contributed to your Roth IRA  (this includes rollovers from a Traditional IRA or Roth 401k  etc., but not the earnings within the Roth IRA that you re-invested inside the Roth IRA), you have a loss that can be deducted on Schedule A as a Miscellaneous Deduction subject to the 2% AGI limit. This 2% is not a cap (in the sense that no more than 2% of your AGI can be deducted in this category)  but rather a threshold: you can only deduct whatever part of your total Miscellaneous Deductions exceeds  2% of your AGI. Not many people have Miscellaneous Deductions whose total exceeds 2% of their AGI, and so they end up not being able to deduct anything in this category. If you ever made nondeductible contributions to your  Traditional IRA because you were ineligible to make a  deductible contribution (income too high, pension plan  coverage at work etc), then the sum of all these contributions is your basis in your  Traditional IRA. Note that your deductible contributions, if any, are not part of the basis.  The above rules apply to  your basis in your Traditional IRA as well.  After the last distribution from your Traditional IRA (the one that empties  all your Traditional IRA accounts and reduces your Traditional IRA balance to zero), total up all the distributions that you received (don't forget to include the nontaxable part of each distribution that represents a return of the basis). If the sum total is less than your basis, you have a loss that can be deducted on Schedule A as a Miscellaneous  Deduction subject to the 2% AGI threshold. You can only deposit cash into an IRA and take a distribution in cash from an IRA. Now, as JoeTaxpayer points out, if your IRA owns stock, you can take a distribution by having the  shares transferred from your IRA account in your brokerage to your personal account in the brokerage.  However, the amount of the distribution, as reported by the brokerage to the IRS, is the value of the shares transferred as of the time of the transfer, (more generally  the fair market value of the property that is transferred out of the IRA) and this is the amount you report on your income  tax return. Any capital gain or loss on those shares remains inside the IRA because your basis (in your personal account) in the  shares that came out of the IRA is the amount of the distribution.  If you sell these shares at a later date, you will have a (taxable) gain or loss depending on whether you sold the shares for more or less than your basis. In effect, the share transfer transaction is as if you sold the shares in the IRA, took the proceeds as a cash distribution and immediately bought the same shares in your personal account, but you saved the transaction fees for the sale and the purchase and avoided paying the  difference between the buying and selling price of the shares as well as any changes in these in the microseconds that would have elapsed between the execution of the sell-shares-in-Tim's-IRA-account, distribute-cash-to-Tim, and buy-shares-in-Tim's-personal account transactions.  Of course, your broker will likely charge a fee for transferring ownership of the shares from your IRA to you.  But the important point is that any capital gain or loss within the IRA cannot be used to offset a gain or loss in your taxable accounts.  What happens inside the IRA stays inside the IRA. 3 Yes, a big yes, it cannot go into the account it came from. Then both accounts >can't be touched for a year. 3) Actually it looks like you can reinvest it in the same IRA account. Based on IRS publication 590 http://www.irs.gov/publications/p590/ch01.html You can withdraw, tax free, all or part of the assets from one traditional IRA if you reinvest them within 60 days in the same or another traditional IRA. Because this is a rollover, you cannot deduct the amount that you reinvest in an IRA. Recommend using quickbooks for account management. If you use the manufacturing and wholesale you can track POs from vendors, estimates, bill payment quotes and invoicing (there's an editor to customize your set up)Also, most accountants are very familiar with this platform so come tax time they'll be able to give you a hand no problem. For accepting payments I highly suggest asking for checks. If you do accept credit cards keep in mind most  payment processors charge a percent (1.5-3%) depending on transaction amounts and quantities of transactions. So you'll want to mark up your products by at least that amount.   Another area is sales tax. Since you are not the end user you should be able to avoid sales tax on the items you will be selling to customers. You then charge the customer this sales tax. Not sure about NJ but in Texas we are 8.25%. I then pay the state of Texas the taxes collected quarterly.   Edit: also make sure you have separate finances for the LLC. Separate checking, separate credit card, separate everything! If you end up using an account that is tied to you personally then you run into the risk of losing the protective nature of an LLC from a legal standpoint.   Edit2: by separate I mean using your IRS issued EIN number to open accounts with the LLC name. When you sign anything on behalf of the company make sure to add the name of the company next to it to show the company is making the signature not you. For instance   u/sexlessnights Company name, LLC