What I Learned From a Family Investing Competition

If only I had understood how important it is to start investing early. My parents came from modest backgrounds and so, when raising their kids, didn’t have much money to invest, let alone investing knowledge to share. By the time I had learned and earned enough to start investing, I wanted to make sure the next generation of my family didn’t make my mistake and miss out on those important early investment years.

But how could a bunch of nieces and nephews of different ages and cultures spread out around the world get inspired to learn about investing? You can’t count on schools. True, some schools have investing clubs or require personal finance classes. But most don’t. Only 17 states require any kind of personal finance education, according to Next Gen Personal Finance, a nonprofit dedicated to improving personal finance knowledge. And even in the best school programs, investing typically takes up only about two weeks of a standard 18-week-semester personal finance course, several personal finance teachers told me. 

Most kids don’t learn much about investing at home, either. A T. Rowe Price survey last year found that 57% of parents were reluctant to discuss money issues with their kids. And here’s the big worry: The same study found that 40% of ’tweens and teens get financial information from social media. 

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A Google search for ideas brings up investing clubs. Maybe other families can get kids to do stock-research homework enthusiastically and regularly, join Zoom calls with their eccentric old aunt, and politely agree on a group investment. Good for those families. For my family, individual competition, not cooperation, seemed a better fit. 

So, in December of 2014, I launched an informal family investing contest. I couldn’t find many good how-to resources, so I just winged it. I opened a dedicated account at an online brokerage with $400. I offered the three oldest members of the next generation — at that time ages 11 to 13 — a holiday present of $100 each in any stock they wanted. I set aside $100 for myself so they could have the fun of besting me. I hounded each of them until they chose an investment. 

From that reluctant start, it has turned out to be so much fun that cousins, uncles and other family members have joined. I now send out regular e-mail updates to the players, naming the winners and losers for both the most recent quarter and since they joined the contest, slipping in little lessons along with the results. There are now 10 members in the group, ranging in age from 12 to 79, spread across four different states and Scandinavia. 

The contest has paid off in all kinds of ways. The original four of us have turned our initial $400 into $720 so far. Admittedly, that is less than we would have made in a broad index fund over the past 9 1/2 years. But we and all the other players who’ve joined over the years have gotten a great, cheap education in investing and built better, um, bonds as a family. 

My nephew Elias, 21, who has dominated the contest because of the strength of his investments in the computer game companies he enjoys (Activision and Sony), says he and his high school and Army buddies sometimes play simulated day-trading games, tracking real stocks, on their smartphones. But, he says, “our contest is more fun because it is real.” And he says it has gotten him so interested in business and economics that he plans to major in those fields when he enters college this fall.

He has more than doubled his money and found a life passion. That’s a great return on a $100 investment! 

If you want a fun, low-cost way to get youngsters excited about investing, and a family activity that can help connect the generations, here are some lessons I’ve learned along the way.

Start on the cheap.

It shouldn’t cost much to start or to run. You can open an account at most online brokerages for free, and some will even help you seed the account with opening bonuses. 

I opened a taxable brokerage account for simplicity’s sake, and I am on the hook for any taxes due. But our holdings are so small, and we do so little trading (because I emphasize buying and holding), that the annual tax bill is low. This winter I received a Form 1099 for $42 in dividends, for example, which added about $9 to my federal tax bill. Larger accounts might necessitate a consultation with a tax expert and perhaps a different setup. 

I confess that I haven’t yet thought through an exit strategy beyond designating a family member as the beneficiary on the account. For now, the assets are officially mine alone, so there’s a level of trust involved. I’m not worried about future cash-outs — I’m not sure we’ll ever reach a level that would trigger gift taxes, for instance. 

The $100-per-person holiday gifts that I used to seed the accounts were admittedly a bit more valuable back in 2014. But even in these inflationary times, $100 is still enough to pique the interest of youngsters. Says 17-year-old cousin Katie: “A hundred dollars is enough. More money might be too scary. Plus, it makes it easy to see who’s ahead.” Besides, she adds, “the whole point is about the bragging rights.” Katie’s three-year-old investment in the iShares Biotechnology fund at first gave her plenty of bragging rights. But lately she has dropped near the bottom of our rankings. 

There is a downside to putting too much money at stake, says Joel Aslanian, a Seattle-based real estate developer whose father-in-law started an investing contest with much higher stakes for his children many years ago. Aslanian watched as the competition sometimes created hard feelings. So when his kids came along, Aslanian wanted to lower the stakes. “I do think it is important for engagement that it involve real money, not a make-believe portfolio,” he says. “I really struggled with the amount of money to start. I didn’t want this to be about wealth transfer. But I wanted it to be enough money to mean something when it went up and down.” He settled on adding a high-three-figure sum every December. “The amount of money involved is really secondary to finding a way to get the kids involved,” he says.

Don't overstep.

Because I am the sole owner of the account, anyone who wants to make a change has to tell me. It’s tempting for us supposedly wiser heads to try to steer the newbies. But the point of this exercise is for youngsters to learn from their own actions in this low-stakes game so they can avoid expensive mistakes with real money later.

My nephew Hunter, 21, loved eating at Cracker Barrel Old Country Store when he was younger (he especially liked the dumplings), so he chose that stock to start the contest. For the next several years, it kept him near the top of the rankings, rising in price and paying a good dividend that was reinvested, compounding his gains. Then COVID hit, and he wanted to sell. It had been such a great performer that I talked him out of it, figuring the stock would bounce back when the pandemic eased. Big mistake. The stock has languished since then. 

To make up for not listening to him, I gave him another stock. He chose Ford Motor in December 2020, which spiked up for about a year. He then sold to pocket a profit of 126%. Humbled, I agreed to sell his Cracker Barrel shares recently so he could invest in a stock he thought would benefit from the artificial intelligence boom: chip maker Nvidia. He still loves Cracker Barrel dumplings, but “it was time to move on, Aunt Kim,” he says.

This experience taught me it’s important to trust the young folks’ judgement. What did Hunter take away? “I feel the best strategy for me is to find a good company to buy low and then get out” when he’s made a decent profit. As the professionals say, “Pigs get fed and hogs get slaughtered.” That is a great life lesson Hunter learned early and with comparatively little pain. So far, his Nvidia stock has done great. 

Be patient — and persistent.

Each kid is different, and will be ready to hear about investing at a different age. The Jump$tart Coalition for Personal Financial Literacy offers investing lessons that start in fourth grade. 

My ’tween and early-teen nieces and nephews rolled their eyes when I made the seed money for the contest their holiday present of 2014. They’d much rather have received a toy or cash to spend as they wished. But my plan was to wear them down. I bugged them until they named a stock. And then I started e-mailing regular updates to them — which they almost never acknowledged — and cc’d their parents and grandparents in hopes that it would inspire conversations at home. Eventually, those e-mails did get some parents, cousins and uncles on board. As more family members joined and talked about the contest, the kids got more excited, too. We benefited from a different kind of compounding “interest.” Their interest in investing grew because of the reinforcement of the quarterly updates and the family conversations among a growing number of their family members. 

Serve as a counterpoint.

Young people are probably going to pick stocks of companies they are familiar with, or those getting a lot of buzz from influencers they follow on social media. So it’s important for the oldsters to use their picks to serve as counterpoints. Uncle Jim, 79, the patriarch of the family, was eager to join the contest because “it is just a wonderfully sneaky way of introducing kids to the realities of investing” and the ups and downs of the market. 

To emphasize his view that stocks currently are overpriced, Jim chose to put his money in cash — a money market account currently paying a little more than 4%. Lately, that’s put him smack dab in the middle of the rankings. He hits “reply all” to every update and makes his case to his grandkids and the other participants that he thinks stock prices are likely to fall because they have risen much faster than corporate earnings. And he reminds the kids that they can switch to safer investments if they choose. 

Keep up the conversation.

Talking with teens can be challenging, but this contest has given us common ground for great conversations. When we gather in person or talk on the phone, I make fun of myself for my terrible stock picks. (I thought Delta Airlines stock would boom as soon as the pandemic eased. Wrong.)

Suzanne Hirsch, a recently retired high school personal finance teacher in Hudson, Ohio, recommends a technique known as the “exit ticket.” Teachers often ask students for summaries of one or two lessons at the end of a class. I just ask friendly questions about lessons learned. 

For example, Elias had done so well with the computer games stocks he was familiar with that his father gave him a little family money to invest. I asked how that was going. Elias said that instead of investing in a company he knew, he had plowed it into a stock he had seen touted on TikTok.

“How’s that doing?”

There was a pause while he checked. Sheepishly: “It’s down 48%.”

“Hmm. What’s the lesson here?”

“I didn’t follow it closely because that takes a lot of time. That’s why funds are nice. They hit every part of the market. I’m thinking I’ll just move to index funds. My mother showed me that if you put the same amount in every month, you hit all the ups and down, but eventually the funds go up.” 

I hung up and did a little private victory dance. If he sticks with that plan, he’ll have won the most important financial contest of all. 

Note: This item first appeared in Kiplinger's Personal Finance Magazine, a monthly, trustworthy source of advice and guidance. Subscribe to help you make more money and keep more of the money you make here.

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