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Your Money Guide on the Side

The Only Investment Guide You Will Ever Need | Andrew Tobias

Your Money Guide on the Side

Tyler Gardner

Business, Education, Entrepreneurship, Investing, How To

4.9 • 2.4K Ratings

🗓️ 19 May 2025

⏱️ 38 minutes

🧾️ Download transcript

Summary

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answer the question, Should I Hire a Financial Advisor? What if the only investment guide you ever needed... actually was? This week, I sit down with personal finance legend Andrew Tobias—bestselling author, Harvard Business School grad, long-time political advocate, and the brilliant mind behind The Only Investment Guide You’ll Ever Need. His book was literally the first financial text I ever read, and it remains one of the few I return to over and over again—for its timeless principles, relatable tone, and surprising humor. In this conversation, we cover: The unlikely path from Slavic literature major to bestselling financial writer Why “don’t be boring” might be the best writing advice you’ll ever get The epic laundry list of startup investments that went very sideways (and what he learned from each) The true cost of chasing returns vs. chasing happiness Why retirement isn't a finish line—but a lifestyle with the right people His most embarrassing investing losses—and how they became his favorite teaching tools Andrew doesn’t just teach people how to manage money—he shows us how to think about it, with warmth, wit, and an honesty that’s rare in finance. 🎧 If you’ve ever wondered what makes financial advice stick—or how to build a life rich in meaning as well as money—this episode is for you. 🔗 Subscribe, rate, and share if it resonates. And thank you for joining me on Your Money Guide on the Side.

Transcript

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0:00.0

There are just a few basic, simple things that everybody should know about money.

0:04.8

Once you know that, you don't really need to know a whole lot of stuff.

0:09.1

In fact, if you do know a whole lot of other stuff, you can get kind of sucked into it.

0:14.2

And before you know it, you're speculating in commodities and losing all your money

0:18.4

or you're doing this and doing that.

0:20.2

It's not like chess or gardening or cooking where the more you're doing this and doing that. It's not like

0:20.9

chess or gardening or cooking where the more you read, the better you get. Hello, friends. This is

0:26.7

Tyler Gardner welcoming you to another episode of your Money Guide on the Side, where it is my job

0:32.1

to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds

0:39.4

in money, finance, and investing. So let's get started and get you one step closer to where

0:45.2

you need to be. My guest today is a personal finance legend. Someone whose work has shaped the way

0:51.9

I first started thinking about money and investing.

0:54.9

In fact, one of his books, The Only Investment Guide You'll Ever Need,

0:58.2

was quite literally the only investment guide I ever used for about 20 years.

1:03.2

And to this day, it sits on my bookshelf, and I keep going back to it

1:07.1

for its timeless principles, its wit, and most of all, its compassion.

1:12.0

Andrew Tobias has that rare ability to make money feel human, less intimidating, more accessible,

1:18.8

and somehow even fun.

1:21.8

Andrew's career has been anything but conventional.

1:25.0

He majored in Slavic languages at Harvard, but spent most of his time

1:28.4

running a student business empire and helping publish Let's Go, the student guide to Europe. He went

1:35.0

on to Harvard Business School, wrote for New York Magazine, Time, and Esquire, and eventually

...

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