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Rule Breaker Investing

January 2026 Mailbag: Values, Kids, Games & Inspiration

Rule Breaker Investing

The Motley Fool

Business, Investing

4.4959 Ratings

🗓️ 28 January 2026

⏱️ 37 minutes

🧾️ Download transcript

Summary

This week’s Rule Breaker Investing Mailbag brings together beautiful questions and stories to start the new year. We wrestle with a values-alignment dilemma around owning Robinhood, explore what it looks like to turn investing into a real, score-kept game for kids (including outperforming Dad), consider a mischievous strategy for the Market Cap Game Show, and close with an inspiring note from a retired basketball coach whose patient, optimistic approach built lasting financial freedom. Along the way, we’re reminded that investing isn’t just about returns—it’s about judgment, temperament, family, and choosing to be a “for” person over time. Sign up for The Motley Fool’s Breakfast News here: ⁠www.fool.com/breakfastnews⁠ Order David’s Rule Breaker Investing book here: ⁠https://www.amazon.com/gp/product/1804091219/⁠ Companies mentioned: HOOD, MELI, NFLX, TTD Host: David GardnerProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

One of the great things about the rule breaker investing mailbag is that it reminds me again and again that investing is never just about numbers.

0:09.7

Sometimes it's about values, how you feel owning a business whose tools can be used well or misused badly.

0:18.8

Sometimes it's about family, teaching kids how to think about money,

0:23.0

about winning and losing, about what average actually means, and sometimes it's about games we play,

0:29.6

rules we bend, whether always clicking disagree, for example, would be a smart strategy

0:35.7

in the market cap game show.

0:44.2

And sometimes, these are my favorite times, it's about a life well-lived, patiently, optimistically,

0:48.8

capital F foolishly, one raise saved at a time.

0:55.6

This week's mailbag takes us to all of those places, different notes, different voices, same question underneath it all. How do we invest in a way that reflects who we want to be? Only on

1:03.3

this week's Rule Breaker Investing. It's the Rule Breaker Investing podcast with Motley Full

1:10.5

co-founder, David Gardner.

1:15.2

Welcome back to Rule Breaker Investing.

1:17.7

Here we are at the end of the first month of 2026.

1:21.0

And as I usually like to do for our mailbags, I'd like to look back briefly at the weeks that were for this podcast.

1:27.1

We had three essays from

1:28.9

yesterday, volume eight, followed by healing leaders, and then calculating risk foolishly. And because I

1:36.5

go back over the month that was, because I like to remind, especially people who may have missed

1:40.6

one of these, why you might enjoy listening to them. Let's briefly survey

1:44.8

where we've been this month. We started with essays from yesterday, Volume 8, kicking off

1:49.8

the year by revealing what I called an investor's secret weapon, and that would be history.

1:55.5

We went all the way back to 2006, 2010, 2012, and 2014, revisiting opening essays written in the middle of, yeah,

2:06.2

forgotten sell-offs, dispiriting markets, moments that felt like the worst possible time

...

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