Bogleheads is a pretty good place to learn about conservative investment strategies based on minimizing risk and taxes.

If you want to take a very brief look, start at: https://www.bogleheads.org/wiki/Lazy_portfolios

My number one piece of advice: invest in the market, never invest in individual stocks.

Find the best index fund you can, and let your money grow with the market.

If you want to get into things like individual stocks, or even angel investing, do it for the fun and the experience, but don't do it for the wealth. "Get rich slowly" is the best advice I've ever been given.

As a business owner the single best benefit you have is contributing to a Solo 401k or SEP-IRA. You can contribute much more into these than an employee can in a typical 401k. It will also help come tax time. I recommend setting one up and maxing it out every year.

As for what to invest in, just go with boring index funds with the lowest expense ratio possible. There is no reason to get cute with investments. Upping your savings rate will do more to build wealth than anything. Let compound interest do the rest.

Finance and wealth building is mostly psychological. Thinking you're smarter than the market is a fools errand because you can't control it. Work on the things you can control like your income and savings rate. Increasing your sweat equity is something you have direct control over as well as how much you spend. Optimizing those will have huge effects on your long term wealth path.

Rule of 12: Start with $12000 and invest in index fund (S&P500 SPY)

every month invest $1000 into that fund (you can always invest rest of the savings in other investments)

S&P long term annual return is 12% (Assuming it remains that)

After 10 years: ~250K After 20 years: ~1M After 30 years: ~3.25M

So if you are in your 30s, when you retire you should have approx 3M from this investment alone (other mutual funds, stocks, real estate, 401K aside)

Now each year you can withdraw 100K for next 30 years (65 - 95)

It's known as "the index card"[1] and it's really the best advice for 99% of people who just want to make the most of their money:

1. max your 401k

2. buy a low cost mutual/index fund (e.g. VFINX)

3. never buy individual stocks/bonds

4. save 20% of your money

5. pay off your credit card balance in full every month

6. maximize tax-advantaged savings accounts (e.g. SEP, IRA)

7. pay attention to fees (i.e. avoid actively-managed mutual funds)

8. only use financial advisors who adhere to a fiduciary standard

9. promote social insurance programs to help people when things go wrong

[1] https://img.washingtonpost.com/blogs/wonkblog/files/2013/09/...

Start with the stock series from jcollinsh (financial blogger)

http://jlcollinsnh.com/stock-series/

This gives a good intro to why index funds are probably your best bet. If you are willing to put in a lot of additional time and research, you may be able to do better picking individual stocks, but probably not.

Four Pillars of Investing by William Bernstein https://www.amazon.com/Four-Pillars-Investing-Building-Portf...

Broadly, I've been doing a 5-fund portfolio with a mix of several index funds in decreasing percentages (total US stock, total international, US bonds, international bonds, REIT). If I had enough money for it to be meaningful, I'd probably invest something on the order of 0.1% in cryptocurrency too.

The rationale is that uncorrelated assets result in average returns (across the set of assets) but decreased risk.

What's unclear to me is the performance of e.g. the S&P 500 once the percentage of investments that are just index funds passes a certain threshold. Presumably if all investors were index fund investors the market would be super stupid, so is there a point before 100% where there will be significantly aberrant behavior? If so, what is that percentage and what is the behavior?

Max out all tax advantaged accounts. Keep your investment costs low, i.e. no mutual funds, or hedge funds, just invest in a diversified bucket of ETFs.*

If you seek financial advisory help, go with a "Fee Only" FA, and be ok spending thousands of dollars for impartial advice. IMO, if you have over about $500k saved, it is probably time to talk to someone.

Make sure you have the right insurance, disability, and life. Disability should cover you in case you can no longer do YOUR job, not just any job. Life should cover your dependents/wife etc.

Avoid timing the market. Evidence has shown that this doesn't work for anyone but the extremely lucky.

*diversification gets hard, and you may need to pay for advice once you reach a certain level of assets (probably around $500k).

Read A Random Walk down Wall Street; Black Swan (by Nikolas Taleb); The Intelligent Investor

These give a good intro on equities.

If you don't already, open an IRA (Roth or traditional). Also, consider reaching out to a certified financial professional for guidance.

It's interesting: when questions like this are asked, you definitely hear the sentiment echoed of "nobody beats the market consistently."

Which appears to be true, at least for the stats I've seen on money managers.

But for the smaller investor, where liquidity is less of an issue (we're not dumping tens of millions at a time), could there be an advantage there?

Or someone privy to industry information - e.g. I knew that New Relic was really popular, because I consult with startups, long before they went public. No surprise on their stock growth.

Just thinking out loud here... I'll probably just stick with our Vanguard Target Date Fund. :)

Read anything by William Bernstein or Jack Bogle.

You can start here with Bernstein: https://www.amazon.com/Investors-Manifesto-Prosperity-Armage...

Or here with Bogle: https://www.amazon.com/Little-Book-Common-Sense-Investing/dp...

I will sum up what we know in general about investing: Keep fees low and diversify.

That is the best you can do without specialized knowledge or effort (and, depending on how strong a view you have of the efficient market hypothesis, even then this might be the best you can do).

In this case you should put the bulk of your money in a robo-advisor like wealthfront or betterment. (I am not related to them in any way).

If you do have insight into something -- maybe you are keyed into local real estate development or you feel you know your industry -- you could get a higher return. Take some small percent of your wealth (say 5%-20%) and put it into this thing you may be good at.

This is my favorite overview: https://research.wealthfront.com/whitepapers/investment-meth...

I highly recommend "I Will Teach You to be Rich" by Ramit Sethi, which I thought was a great way to get the fundamentals in place. I've bought copies for several of my friends who had no idea what to do with their money.

If you really have tons of money and don't know what to do with it and also have your own business, I'd talk to a CPA about maximizing your tax benefits (if you haven't already) and also to a financial advisor for the rest. CPAs are one of those ROI multiplier type things, where you give them a little money and they save you a whole lot, especially if your tax situation is complicated.

If you're interested in investing in the stock market (specifically picking individual stocks), I recommend the following books:

1. https://www.amazon.com/Little-Book-Still-Beats-Market/dp/047...

2. https://www.amazon.com/Acquirers-Multiple-Billionaire-Contra...

We recently published our 3 courses on Udemy covering this very topic. ( https://www.udemy.com/courses/search/?q=vestu )

The courses walk you through investment principles, investment assets, and portfolio implementation. Simple overview... Get the market return, get it for lowest cost possible, enhance returns by investing where the market historically outperforms, rebalance annually.

Investing in the market is good advice for most people. But many people are not such a great financial position as you.

If you run a business the best investment you can make is in you own business. By all means, max out your 401k contribution. But if there is money left over to invest, conciser investing in your own business.

Here is a podcast I listened to just the other day about this: http://www.tropicalmba.com/monies/

It really depends on how much effort and risk you want to take. Much of the advice you will receive on HN comes from Bogle and his Vanguard index funds. That is the lowest effort and risk you can take.

But, if you want to invest some more time and take additional risk (and maybe better returns) try reading some books. Peter Lynch's - One Up on Wall Street and Benjamin Graham's - The intelligent Investor are two good ones to start with. These will give you a solid platform on stock selection.

Shameless plug, but we have a podcast around commercial real estate investing, a very popular investment type for passive income generation. We really have a big education focus:

https://www.realcrowd.com/blog/2018/01/podcast-best-of-seaso...

Is your business also your job? Then that’s sort of one source of income. Depending on how much money you have you might want to diversify.

I've liked bogleheads forum. The usual advice would be to maxmimize 401(k), ROTH IRA and invest in index funds.

One resource, to get your feet wet, is to get a Paper Trade Account. Take a look at interactive brokers. Read some books, get ideas, and test them out in a Paper Trade Account. Then when you are ready, and comfortable, move into "Real Life" trading.

Depending on how much time you want to spend, I suggest a subscription to Real Vision. If you just want to invest in an index fund, then it's probably overkill, but they have high-quality, interesting content that is definitely worth the $15/month.

Mr. Money Mustache. Ignore the cult bits, read it anyway.

The millionaire next door.

This question keeps coming up by the way.

If you have a business, probably makes sense to hire an advisor, especially with the latest tax changes, because the business is an important vehicle for investment.

As someone in the financial industry, I can throw out a few suggestions. These vary substantially depending on your level of interest, time, and risk-tolerance. I am not a financial advisor, nor should you consider any of this professional investment advice. I know your question is geared toward resource and learning. I will address that, but I'll also include the easier options if you decide to just say screw it and go the simple route. That being said...

You could go the low risk, low-cost, near-zero time method of using index funds. For full disclosure, this is the area of the industry I am involved with. You can either choose the funds yourself or you can get someone to provide you some suggestions. There are advisors out there who specialize in tactical weighting of a defined set of index funds (i.e. the funds you have available in your 401k for example). They vary the weights usually on a quarterly basis on a set of criteria that is proprietary to them. This tactical weighting can outperform the market if they know what they are doing. They will, however, charge the standard advisory fee for this.

You could just hand over the reigns to an advisor after speaking to one your are comfortable with. they'll charge their standard rate and if they are halfway decent they will match your investments to your risk profile/tolerance. Be wary, though, as many may just shovel you into a default set of index funds. If you pay an advisor you need to be sure they actually add some sort of value and that they adhere to fiduciary standards (not "suitability" standards)

if you actually want to focus on individual stocks, please please please at least learn the absolute basics about fundamental ratios and how to look at a balance sheet or cash flow statement. Or actually know the company you are investing in. There are many books out there. The gold standard about value investing is Ben Graham's famous Intelligent Investor.

real estate is a fairly tried and true method. investment properties produce reliable cash flow. there are property management companies out there that will charge usually around 10% of the rent to keep your place rented and handle the landlord duties.

you could also focus on a stock market strategy geared toward passive income. something like a covered call strategy. that is a strategy commonly used in a sideways market or a market not strongly trending in either direction to produce cash flow by owning the stock and issuing/writing a call against it where you collect the premium. A few books I have read that offer some good intro to the basics of options strategies (and a few slightly more advanced methods) are the followings ASINs on Amazon - B014C59R9S, B01EPJC2T8, B0165YDUSS, and B00YBIK9P8. They're short and very straightforward to help understand the basics and also generate some ideas for yourself. They're only like $3 a piece, too.

moving up the ladder of education and effort - you could pay for training courses for a site like WallStreet Mojo. I happen to have purchased all their stuff in a recent sale they had (like 85%+ off), which they have from time to time. They also have some free stuff for you to check out. It looks like they are running a special right now on the premium courses. Not sure how long that is in force. https://www.wallstreetmojo.com/courses/ They have courses targeted for investment banking, CFA, financial modeling, etc. Their courses include videos and downloadable Excel templates/examples to learn with. It's time consuming, but if you are actually interested in how the financial analysts and investment bankers perform valuations then it's a pretty solid tool/resource. Their CFA courses are obviously geared toward the CFA exam, but the knowledge is the same and can be applied in any way you choose. You would be able to skip the compliance and ethics portions and just focus on the rest. this information combines to form a much more in depth valuation toolbox and you could theoretically choose stocks with success using careful analysis, or perhaps create fund-style strategy to spread out the risk of your personal portfolio.

you could also purchase an existing business that is for sale. they are plenty of sites dedicated to these sales. if you find something you like, get an attorney who knows about these transactions. this basically is a sort of turn-key solution that provides relatively predictable cash flow. but it's not quite turn-key as businesses require work and you already own/run one. if you decide to go this route, i would suggest making sure the cash flow has enough wiggle room to hire someone to replace your own involvement, as you likely won't have the time to run it yourself.

Invest in start-ups? https://angel.co/

"Rich Dad, Poor Dad" is pretty much the only "finance" book that's useful to the common person that I know of. Explains the basics.

"The Intelligent Investor" wasn't helpful to me at all, and I could actually understand what he is talking about, having a heavy background in finance.

P.S. a college degree or being a CFA won't help, from personal experience, though every other finance grad claims it will. The moment I started doing fundamental analysis is the moment my portfolio went to shit.

Helpful tl;dr: "index funds".

Always disappointed to see " index funds " repeated ad nauseum in these threads.

I assuming op wants something creative and new advice. Not index fund advice.

You’re gonna want to follow plane-Jane bog-standard investment advice. Remember, youre not a full-time Wall Street central banker and can’t devote all your time to due diligence. Go the buffet route and create a long-term, diversified portfolio of cheap low-fee crypto currencies and don’t touch it until retirement.