How would one follow the “smart money” when people use that term?
"Smart money (Merriam-Webster, Wiktionary) is simply a term that refers to the money that successful investors invest.  It can also refer to the successful investors themselves.  When someone tells you to ""follow the smart money,"" they are generally telling you to invest in the same things that successful investors invest in.  For example, you might decide to invest in the same things that Warren Buffett invests in.   However, there are a couple of problems with blindly following someone else's investments without knowing what you are doing. First, you are not in the same situation that the expert is in.  Warren Buffett has a lot of money in a lot of places.  He can afford to take some chances that you might not be able to take.  So if you choose only one of his investments to copy, and it ends up being a loser, he is fine, but you are not. Second, when Warren Buffett makes large investments, he affects the price of stocks.  For example, Warren Buffett's company recently purchased $1 Billion worth of Apple stock.  As soon as this purchase was announced, the price of Apple stock went up 4% from people purchasing the stock trying to follow Warren Buffett.   That having been said, it is a good idea to watch successful investors and learn from what they do.  If they see a stock as something worth investing in, find out what it is that they see in that company." To supplement Ben's answer: Following 'smart money' utilizes information available in a transparent marketplace to track the holdings of professionals.  One way may be to learn as much as possible about fund directors and monitor the firms holdings closely via prospectus. I believe certain exchanges provide transaction data by brokers, so it may be possible for a well-informed individual to monitor changes in a firms' holdings in between prospectus updates.  An example of a play on 'smart money':  S&P500 companies are reviewed for weighting and the list changes when companies are dropped or added. As you know there are ETFs and funds that reflect the holdings of the SP500.  Changes to the list trigger  'binary events' where funds open or close a position. Some people try to anticipate the movements of the SP500 before 'smart money' adjusts their positions. I have heard some people define smart money as people who get paid whether their decisions are right or wrong, which in my opinion, best captures the term. This Udemy course may be of interest: https://www.udemy.com/tools-for-trading-investing/
I think you have already outlined for yourself most of the pros and cons of each method of giving. It sounds to me like you have some desire to control how the money is spent, or at least reserve the right not to give it to a child who will waste it (according to your definition).  If you set up an UTMA/UGMA account, or just give the money directly each year as a birthday gift, you are surrendering control of the money. It's a gift and is no longer yours to direct.  If you set up a 529, you at least restrict the money to a particular, useful purpose. Moreover, if you retain ownership of the 529, you can take the money back, albeit with a tax penalty to yourself.  If you do hold a 529 in your name, but for a child's benefit, there are a couple of things to consider with respect to future financial aid (this is from recent experience--my in-laws have 529s for our children, both of whom are currently in college). A 529 not owned by the student or the student's parent is not reported as an asset (of the child or the parent) on the Free Application for Federal Student Aid (FAFSA). However, once such a 529 is used to pay college expenses, the amount of those payments does get reported on the following year's FAFSA, and counts as untaxed income for the purposes of figuring the Expected Family Contribution (EFC). Untaxed income is assessed towards the EFC at 50%. In contrast, parental assets are assessed at around 7%, if I recall correctly, and student assets at around 35%. Student-owned 529s are assessed at the rate of parental assets, which is an advantage. If the amount you will set aside is less than the cost of one year of college, you can avoid the disadvantage of the untaxed income assessment by just using the entire 529 for the final year of school, since there will be no FAFSA for the following year. It occurs to me that there is one other way you can give to them that you did not mention, and may make you more comfortable in terms of encouraging some positive behavior. Namely, save the money in a self-owned account, then, when they are old enough to get a job that provides a W-2 showing declared, earned income, you can use the savings to fund a Traditional or Roth IRA for them, up to the limit allowed each year, until the money you set aside is exhausted. The Roth is a better long-term savings vehicle, but the Traditional would carry bigger penalties for early withdrawal and would therefore be less tempting to draw on. While there are lots of really plausible explanations for why the market moves a certain way on a certain day, no one really knows for sure.  In order to do that, you would need to understand the 'minds' of all the market players.  These days many of these players are secret proprietary algorithms.  I'm not quibbling with the specifics of these explanations (I have no better) just pointing out that these are just really hypotheses and if the market starts following different patterns, they will be tossed into the dust bin of 'old thinking'. I think the best thing you can explain to your son is that the stock market is basically a gigantic highly complex poker game.  The daily gyrations of the market are about individuals trying to predict where the herd is going to go next and then after that and then after that etc. If you want to help him understand the market, I suggest two things.  The first is to find or create a simple market game and play it with him.  The other would be to teach him about how bonds are priced and why prices move the way they do.  I know this might sound weird and most people think bonds are esoteric but there are bonds have a much simpler pricing model based on fundamental financial logic.  It's much easier then to get your head around the moves of the bond markets because the part of the price based on beliefs is much more limited (i.e. will the company be able pay & where are rates going.)  Once you have that understanding, you can start thinking about the different ways stocks can be valued (there are many) and what the market movements mean about how people are valuing different companies. With regard to this specific situation, here's a different take on it from the 'priced in' explanation which isn't really different but might make more sense to your son: Pretend for a second that at some point these stocks did move seasonally.  In the late fall and winter when sales went up, the stock price increased in kind.  So some smart people see this happening every year and realize that if they bought these stocks in the summer, they would get them cheap and then sell them off when they go up.  More and more people are doing this and making easy money.  So many people are doing it that the stock starts to rise in the Summer now.  People now see that if they want to get in before everyone else, they need to buy earlier in the Spring.  Now the prices start rising in the Spring.  People start buying in the beginning of the year... You can see where this is going, right?  Essentially, a strategy to take advantage of well known seasonal patterns is unstable.  You can't profit off of the seasonal changes unless everyone else in the market is too stupid to see that you are simply anticipating their moves and react accordingly. "Plenty!  Following are just a few: For things like RESP and RRSP which have an ""end"" date; as you or your children age, you should be migrating to less speculative investments and more secure ones.  When children are young, for example, you might be in a ""growth"" type fund.  Later on, you would likely want to switch that to an ""income"" fund, which is also more conservative and less likely to lose principal. Are you getting the best benefit from your credit cards?  Is there another card with benefits that you would get more ""back"" from using?  Is that fee-based Air miles card worth it?  Is cash-back better for you? If you have regular investment withdrawals, can you increase them?  Do you like the plan they are going in to?  Similarly look over any other long-term debt repayment.  Student loans, car loans, mortgage.  What is coming up this year, what is ""ending"".  If, for example, car payment will end, how will you earmark that money, so it just does not disappear into general funds. While you could go over things like these more often, once a year should be plenty often to keep tabs and not obsess. Good Luck!" What are the risks pertaining to timing on long term index   investments? The risks are countless for any investment strategy.  If you invest in US stocks, and prices revert to the long term cyclically adjusted average, you will lose a lot of money.  If you invest in cash, inflation may outpace interest rates and you will lose money.  If you invest in gold, the price might go down and you will lose money.  It's best to study history and make a reasonable decision (i.e. invest in stocks). Here are long term returns by asset class, computed by Jeremy Siegel:  $1 invested in equities in 1801 equals $15.22 today if was not invested and $8.8 million if it was invested in stocks.  This is the 'magic of compound interest' and cash / bonds have not been nearly as magical as stocks historically. 2) How large are these risks? The following chart shows the largest drawdowns (decreases in the value of an asset) since 1970 (source):  Asset prices decrease in value frequently.  Financial assets are volatile, but historically, they have increased over time, enabling investors to earn compounded returns (exponential growth of money is how to get rich).  I personally view drawdowns as an excellent time to buy - it's like going on a shopping spree when everything in the store is discounted. 3) In case I feel not prepared to take these risks, how can I avoid   them? The optimal asset allocation depends on the ability to take risk and your tolerance for risk.  You are young and have a long investment horizon, so if stocks go down, you will have plenty of time to wait for them to go back up (if you're smart, you'll buy more stocks when they go down because they're cheap), so your ability to bear risk is high.  From your description, it seems like you have a low risk tolerance (despite a high ability to be exposed to risk).  Here's the return of various asset classes and how the average investor has fared over the last 20 years (source):  Get educated (read Common Sense on Mutual Funds, A Random Walk Down Wall Street, etc.) and don't be average! Closing words: Investing in a globally diversified portfolio with a dollar cost averaging strategy is the best strategy for most investors.  For investors that are unable to stay rational when markets are volatile (i.e. the investor uncontrollably sells their stocks when stocks decrease 20%), a more conservative asset allocation is recommended.  Due to the nature of compounded interest, a conservative portfolio is likely to have a much lower future value. "There are places that call themselves quant funds that are like what you describe, but most are not. ""Quant fund"" can just about mean anything from ""we use computer screens when we read 10-Ks"" to ""our PhDs write signal processing programs without even knowing what the input data represents, and we run those programs with no manual intervention.""" "Suppose you have $100 today and suppose that hamburgers cost $5. If you are holding $100, you could buy 20 hamburgers at $5 each. Now suppose you take that $100 and stuff it under your mattress for 24 years. When you pull out your money, you still have $100, but it turns out hamburgers now cost $10.   The increase from $5 to $10 is inflation.   Your savings of $100 was ""eroded"" by half even though before and after you had $100 and now you can only buy 10 hamburgers instead of 20 hamburgers. Suppose inflation is 3%.   That means that if you earn 3% return on your investments, you'll stay even with inflation (If you can buy 20 hamburgers today, then at any point you can still buy 20 hamburgers).   If you want your money to grow in a real, tangible way you'll want to seek returns that beat the rate of inflation." Recessions are prolonged by less spending and wages being 'sticky' downward. My currency, the 'wallark', allows a company to pay its workers in it's own scrip instead of dollars which they can use to purchase its goods, thus reducing it's labor costs and allowing prices to fall faster. While scrip in the past purposely devalued to discourage hoarding, the wallark hold's it's purchasing power. The difference is, a worker can only use it to purchase their company's good *on the date the wallark was earned or before*.  In other words, each good is labeled with a date it was put on display for sale, if  a worker earns scrip on that same day, they can trade the scrip for that good, or any good that was on the shelves on that day it was earned *or before that date*. Any good that comes onto market after the date that particular wallark was earned cannot be purchased with that wallark(which is dated), and must be purchased either with dollars or with wallark that was earned on that good's date or after. This incentivizes spending without creating inflation, and allows costs to fall which helps businesses during rough economic times.  Please feel free to read it, and comment on my site! Any feedback is welcome! That's the point though.  They are allowing themselves to be *led*, in the first place, to the decision to do something with their capital that they don't understand.  While I don't condone how these Wall St. people behave with peoples money (hence why I don't put any of my money into it), I also cant sympathize with the people who lose money to Wall St. because they were too lazy to be informed about what was going on with their money and to act in their own best interest.  I am guessing (pure speculation) that a lot of the problem with the financial industry could've been avoided if people were proactive about their money and only made investments that they were personally knowledgeable about.