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Most companies keep their shareholder list electronically, rather than sending paper stock certificates. A company that goes public will give their shareholder list to a transfer agent. For example, my company used the American Stock Transfer & Trust Company, and I received paperwork in the mail listing my account number with them.To sell the stock, it must be transferred to an account at a brokerage. I provided my account number to ETrade, as well as a scanned copy of my latest statement from AST, and they took care of moving the account. It’s only a little more complicated to tell them to move some but not all of the shares in the transfer agent account.(If you for some reason hold paper certificates, it’s a similar process— you send the certificate in to the brokerage in the mail, along with the appropriate form, and they deposit it into your account. Some brokerages may charge a fee for this.)The IPO underwriters generally require a 180-day lockup period for existing stockholders, so pre-IPO stockholders will not be able to complete a sale until six months after the IPO.

Trusting someone to handle my investments “for” me.My wife’s uncle took thousands of dollars and “invested” it for me. Years later, I was buying Apple stock and asked him to pour all my cash into it.He convinced me that diversification is key and that’s how they do business. I decided to open a meager etrade account and buy some Apple stock in it.16 years later, my account with him went up maybe 190%. The etrade account was in the 11000% range.F that. Imma control my own money.

Call Betterment and ask, because their FAQ doesn’t say. Then instruct Vanguard to initiate a transfer request from Betterment. But wait, there’s more!Betterment | Deposits, Withdrawals, Transfers via the Betterment FAQThe Depository Trust & Clearing Corporation (DTCC) supports the Automated Customer Account Transfer Service (ACATS) between financial institutions that are qualified National Securities Clearing Corporation (NSCC) members and/or Depository Trust Company (DTC) bank participants.In theory, Betterment supports ACATS transfers, at least for transfers in (the FAQ says so), but the company doesn’t specify support for transfers out.But first, what you can transfer out depends on what kind of account you open at Vanguard.If you open a Vanguard “mutual fund” account, you can only buy and sell Vanguard mutual funds in that account. That’s it. You cannot use the mutual fund account to buy, sell, or hold Exchange Traded Funds (ETFs).Types of mutual fund investment accounts via VanguardSo if you open a Vanguard mutual fund account, you cannot transfer the ETFs held in your Betterment account via ACATS to Vanguard. Period.You will have to first instruct Betterment to sell all of your ETF holdings, wait for the proceeds to settle to cash, and then transfer the cash (maybe by a paper check, maybe an ACH transfer to your bank account, you have a few options I suppose) to Vanguard where you can use the cash to buy Vanguard mutual funds. If your Betterment account is taxable (and not a tax-advantaged account like an IRA), any capital gains and losses will be reported on a Form 1099-B by Betterment, which you ultimately will report on your tax return.Ok, since the mutual fund account won’t work for the ETFs you want to transfer, what’s left?To buy, sell, and hold ETFs with Vanguard, you need to open a Vanguard “Brokerage” Account.Since this is a brokerage account, it’s like most brokerage accounts with all of the online trading brokers like eTrade, TD Ameritrade, Charles Schwab, etc. where you can pretty much buy any stock, mutual fund, ETF, and other investments traded on the primary U.S. stock exchanges (e.g. NYSE and NASDAQ). Note that you will pay brokerage commissions for each of your trades in a brokerage account, because that’s just how brokerage accounts work and how brokerage firms make revenue.Know your ETF brokerage account options via VanguardBut wait, there’s more!Betterment employs a proprietary accounting system, allowing customers to benefit from the use of fractional share interests.See What am I getting for Betterment's ... via BettermentSome of the ETFs Betterment uses cost more than $100/share, so unless you had $100 cash in your account, you normally wouldn’t be able to buy one share of that ETF until you used all $100 to buy it. But for accounts with small balances, buying that one single share could potentially throw off your asset allocation.So Betterment uses its own internal proprietary accounting system to “split up” that one ETF share into fractional share interests, and then allocates those fractions across multiple customer accounts using its internal accounting system.(Think of it like a virtual machine on a computer server. The actual server is just one server, i.e. one box of hard drives, memory, and processors. But the server can be split up into many “virtual machines,” each virtual machine effectively running just like a normal computer. Only the virtual machine doesn’t use 100% of the server’s resources, because the server is so powerful, it can support multiple virtual machines all from the same box of hardware. But you can’t just unplug your virtual machine hardware and move it somewhere else, because it’s virtual; it doesn’t operate with its own self-contained hardware. It uses shared hard drive, memory, and processor resources owned by the server. Now back to Betterment)The ETF share never actually gets “split up” in real life. Think of it more like a spreadsheet that Betterment manages. See How do fractional shares at Betterment work? on Quora for more details.So what does this have to do with rolling over your account to Vanguard?Those fractional share interests can’t be rolled over to a brokerage account. I don’t know how things actually work here, but in theory, you should be able to tell Betterment to “sell” (better yet, “redeem”) all of your fractional share interests, and in exchange, you should get a bit of cash in return. One downside here, though, is that your fractional shares are still subject to capital gain/loss reporting (again, assuming you have a taxable account), so you’re going to get a Form 1099-B at the beginning of next year that you need to report on your tax return. You simply can’t avoid it. (You can avoid it by using a tax-advantaged account, i.e. an IRA, which doesn’t trigger the Form 1099-B reporting)Now getting a 1099-B isn’t the end of the world since only your fractional share interests are being redeemed and not 100% of your account. The dollar amounts we’re talking about here are not terribly high (I would guess a range of $50 in losses to $100 in gains seems realistic for most customers), so I don’t see a huge need to try and avoid this. It’s just part of using Betterment for your after-tax investing.¯\_(ツ)_/¯So back to your original question.If you’re attempting to roll over your taxable Betterment account to another brokerage account to avoid triggering capital gains/losses whatsoever, in my opinion, it can’t be done. You’re going to get a 1099-B no matter what. That’s the way Betterment works. By allowing customers to invest their money down to the penny, Betterment uses fractional share interest accounting, so when you want to move your investments out of Betterment, you’re going to be forced to give up those fractional share interests because they only exist within the confines of Betterment’s computers.Finally, for the whole shares of ETFs remaining in your Betterment account, those, in theory, should be able to transfer via ACATS to your destination brokerage account where you can do whatever you want with them.One final note: Your new brokerage account charges you commission each time you buy and sell ETFs, so if you plan on selling some of the ETFs that transfer over from Betterment, you will end up paying commission on each one. Think of that before leaving Betterment, because if you instruct Betterment to sell your ETFs while still at Betterment, Betterment won’t charge you a commission. You’re already paying for ETF trading in your annual 0.15% to 0.35% fee to Betterment. So in some cases, you will save money by moving your Betterment account to cash first instead of paying a bunch of commissions to another broker to sell the ETFs transferred over from Betterment.Thank you for reading this far, and I hope this was helpful for you in walking through all the nuances of something that, at a distance, seems pretty straightforward. If this was useful, please let the Quora community know by giving my answer an Upvote!Note: Quora is great and all for tax, investing, and financial information, but don’t rely on it for your specific needs. Consult with a tax professional and/or registered investment adviser first before you make any financial decisions.