What you have depends on your situation. If your employer doesn't match funds the 401 is probably a waste. If it does, you likely want the match. Most people select Roths over traditionals because the money paid in can be taken out without penalty.
Roth EARNINGS are subject to taxes and early withdrawal penalties. Assuming the investment options are ones you would like to be in otherwise, your 401k will probably have access to lower fee structures than the normal retail funds. Many times though with smaller companies, the funds aren't very good and the fee savings either aren't there or aren't worth it. Many 401k plans don't offer Roth, but the adoption rate seems to be growing.
Maybe I should start that in 2018 and not contribute past the match.
For arguments sake, if I have $100 (post match amount) each paycheck that I can buy some Vanguard fund in my 401K, or some equity in an IRA - does that make enough of a difference?
I would for two main reasons: 1) accessibility and 2) more investment options (and commonly better options).
Contribute enough to get the match.
Contribute to a Roth IRA.
If/when you reach the limit (or don't get the benefit), defer more to the 401k.
Granted all of this is in a bubble. There are a gazillion other things to do with your money...
Can I have more than one of each kind (standard and Roth)? Should I?
Where do I get them? I have a 401(k) through work, but I don't think that individual tinkering is allowed, even if I wanted to.
Should I get an IRA, continually fund it and the 401(k) and let them be, but then also buy choice stocks individually outside of those investments, just to experiment without disturbing the main game?
How do I choose which stocks, bonds, etc., to buy, without having to take up investment research to the point of writing it off as an expense? Is that even allowed?
How do I begin to wrap my head around taxes on all of this? Is reporting to the IRS automatic with these accounts, or is it all on the investor to keep himself out of the sausage maker?
How soon can some of these investments start kicking back more than it takes to buy in further? At what point do I stop reinvesting the returns into more stock and take the profit? Are there generic formulas for this? Does it even work like that?
I seem to recall Jack saying once that if you didn't have $30,000 to invest then it was better to save up that 30k than to begin investing at a lesser amount.
Yes you can have more than one account and more than one tax structure. Most people (even more on boards like this) think that taxes will go up, either as your income bracket goes up with age or as the gov't wets the bed. So younger people tend to use Roth more.
Some 401k plans have a brokerage window where you can invest in most equities, bonds, and mutual funds. Most only have between 10-20 funds to choose from.
You can open an IRA at pretty much any financial institution. From you bank or credit union (typically in CD's) to the huge banks and mutual fund companies. For an IRA, I'd recommend an online broker.
http://scottrade.com/ - I use this one.
https://www.tdameritrade.com/home.page https://client.schwab.com/Login/SignOn/CustomerCenterLogin.aspx?ErrorCode=ErrorEmptyLoginIdPwdhttps://us.etrade.com/what-we-offer/our-accounts/?sr_id=BR&mp_id=41378076217&ch_id=pInvesting isn't a get rich quick scheme. If you don't understand what you're buying, you're probably better off letting 'experts' do it. Meaning choosing a mutual fund. Or like David mentioned, rip off the experts knowledge by seeing what they hold in the top 10 holdings. The top 10 holdings in a mutual fund are public information (you can find them on Yahoo Finance). It's best to put the time in to learn a bit before tossing your money on the table.
A few years ago the IRS made some type of change that required brokers to report the tax basis, gains/losses, etc. So taxes are much easier. I will say that, if you have a taxable event (sale, divs...) you won't be able to use the free software though. You'll need to upgraded TurboTax (or whatever).
How long it takes is the Magic 8 ball question. Depends on your goals, cost of living, etc. Some people use the dividends earlier than retirement to supplement their income.
A good rule of thumb for dividend income (assume a 7% yield) is about $1,000/month for every $250,000 balance. So if you want a $4k/month you need a $1 million balance.
Personally, I would start with less than $30k. And did. I didn't hear the episode you're talking about, but I would assume it has to do with diversifying your risk. $5k in 6 different industries/types of investments. But at that point you're getting into modern portfolio theory with the goal of reducing risk with the same reward.