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Rule Breaker Investing

August 2025 Mailbag: Sports Bettor Turned Investor

Rule Breaker Investing

The Motley Fool

Business, Investing

4.4 • 959 Ratings

🗓️ 27 August 2025

⏱️ 64 minutes

🧾️ Download transcript

Summary

For summer’s final Mailbag, a listener shares how he dropped sports betting and picked up investing, while another wants to know how to allocate portfolios as a Rule Breaker. David brings back Motley Fool Chief Investment Officer, Andy Cross, to discuss tools for tracking your portfolio against the S&P 500, thinking briefly about dividend allocation, then answering the question, “If you were investing your first $1,000 today, what would your approach be?” Those gems, along with Author in August Sam Horn—like a river—running through it! Sign up for The Motley Fool’s Breakfast News here:www.fool.com/breakfastnews Pre-order David’s upcoming Rule Breaker Investing book here: https://www.amazon.com/gp/product/1804091219/ Host: David GardnerGuest: Andy CrossProducer: Bart Shannon Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0

Well, here we are at the end of August and at the end of our eighth year of authors in August.

0:05.0

What a delight it was to spend time with authors like Arthur Brooks and Sam Horn and friends like Chris Hill.

0:12.2

Thank you for your notes, which I'll share back about our authors in August this month.

0:17.5

And a listener recently dropped sports betting and picked up investing. Same competitive

0:24.4

fire, totally different game. If you were starting fresh with your first $1,000 today,

0:30.8

would you go rule breaker like ETFs or take your first swing at individual stocks.

0:37.5

We'll also pop the hood on how to actually track a portfolio against the S&P 500 dividends

0:42.9

allocations.

0:44.3

And also, how do you allocate portfolios for a rule breaker only on this week's rulebreaker

0:49.8

investing?

0:52.4

It's the rule breaker investing podcast with Motley full co-founder, David Gardner.

1:00.3

Welcome back to Rule Breaker Investing. Happy end of August. Happy near end of summer. We're about to get

1:08.5

started with our monthly mailbag at the end of every month,

1:13.1

the final Wednesday of every month, for dozens of months in a row now. We have done a mailbag.

1:19.3

You get to write in RBI at fool.com is our email address. You can also tweet us at RBI

1:25.7

podcast on TwitterX. We read every piece of mail that comes in. We filter

1:30.4

in the best and craft a mailbag for you. It's maybe my favorite episode to do every month,

1:35.7

because we get to talk together. We get to share. And sure enough, that's exactly what's happening

1:39.9

once again this week. Before we get started, a few bookkeeping notes. First, I'd like to point out

1:45.7

that with my own book, Rule Breaker Investing, coming out in a few weeks, I find myself doing a fair

1:50.4

number of external interviews these days, weeks, and in the months to come. And I'll occasionally

1:56.6

call them out here, because if you're not sick after hearing me speak for, I don't know,

...

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