Heads I Win, Tails I Win

Why Smart Investors Fail and How to Tilt the Odds in Your Favor

By: Spencer Jakab

Narrated by: Sean Pratt

Investing is one of the few areas in life where even very smart people let hope triumph over experience.

According to Wall Street Journal investing columnist Spencer Jakab, most of us have no idea how much money we're leaving on the table - or that the average saver doesn't come anywhere close to earning the "average" returns touted in those glossy brochures. We're handicapped not only by psychological biases and a fear of missing out but by an industry with multimillion-dollar marketing budgets and an eye on its own bottom line, not yours.

Unless you're very handy, you probably don't know how to fix your own car or give a family member a decent haircut. But most Americans are expected to be part-time fund managers. With a steady, livable pension check becoming a rarity, we've been entrusted with our own finances and, for the most part, failed miserably.

Since leaving his job as a top-rated stock analyst to become an investing columnist, Jakab has watched his readers and listeners - and his family, friends, and colleagues - make the same mistakes again and again. He set out to evaluate the typical advice people get, from the clearly risky to the seemingly safe, to figure out where it all goes wrong and how they could do much better. Blending entertaining stories with some surprising research, Jakab explains:

• How a typical saver could have a retirement nest egg twice as large by being cheap and lazy
• Why investors who put their savings with a high-performing mutual fund manager end up worse off than if they'd picked one who has struggled
• The best way to cash in on your hunch that a recession is looming
• How people who check their brokerage accounts frequently end up falling behind the market
• Who isn't nearly as good at investing as the media would have you think

He also explains why you should never trust a World Cup-predicting octopus, why you shouldn't invest in companies with an X or a Z in their names, and what to do if a time traveler offers you economic news from the future.

Whatever your level of expertise, Heads I Win, Tails I Win can help you vastly improve your odds of investment success.

©2016 Spencer Jakab (P)2016 Gildan Media LLC

Critic reviews

"As Pogo used to say, 'We have met the enemy and he is us.' In this delightfully written book, full of wonderful anecdotes, Spencer Jakab shows us how to win the investment game by avoiding the stupid choices that even 'smart' investors make." (Burton G. Malkiel, author of A Random Walk Down Wall Street)

Got my head screwed on straight

In these turbulent markets, Jakab’s book couldn’t have come at a better time. He channels a lot of the time-tested wisdom we have read from the likes of Graham and Bogle into a distilled and easy-to-consume format, bringing in his years of experience as an analyst and financial journalist. Overall a wonderful perspective to learn from with no BS flags going up. Do yourself a favor and buy a copy, before you do something stupid!

A Good, Honest, Reality Check!

What did you love best about Heads I Win, Tails I Win?

I really appreciated Spencer's point of view about investing. We all think that we are above the odds or above average; and its time that we had a good hard look at our true odds at "winning" the market. Average returns sound bad but when everyone else is lagging the S&P 500, suddenly it brings some much needed perspective on the subject. This book's style of simple and straight forward advice reminded me of a Canadian classic; The Wealth Barber, and i really appreciated that aspect. Simple ideas that anyone can use.

What was one of the most memorable moments of Heads I Win, Tails I Win?

The Important things to know:-Interfering with your investments in an attempt to achieve better performance = BAD.-Avoiding actively managed funds because only hindsight is 20/20 = GOODThe subject of Baron Rothschild in the first half of the book was a really great example of why its important to have proper diversification to withstand hard times in the market and not always "swing for the fences". Best of all, in the last few chapters, Spencer lays out how this doesn't have to be as complicated as some make it out to be.

What does Sean Pratt bring to the story that you wouldn’t experience if you just read the book?

I loved having the narrator for this book, because I felt like it allowed the occasional sarcasm and humor infused into the book to be more effective. Like having a casual chat with a mate.

If you were to make a film of this book, what would the tag line be?

Sit back and relax, you were only making it worse.

Any additional comments?

There were moments of "Inside Baseball" and stories of his time in a firm that I wish we could hear more about. I always appreciate hearing people's experiences behind the scenes, perhaps this could be the start of a more detailed memoir in the years to come. With his connections I'm sure it would be great.

Best book ever for "average" and investors

Everything you ever needed to hear about your own greed and/or fear related to investing. Just a great, extremely level headed look at the market and your place in it.

Great perspective

Nice potrayal of the financial world from a former insider. Easy to follow even for a 30 yr old with an 8th grade financial literacy level.

Interesting Information

If you could sum up Heads I Win, Tails I Win in three words, what would they be?

Valuable Information Interesting

What did you like best about this story?

Most of the information in this book is for the advanced beginning investor with a few added twists that would add to the knowledge of any investor.

Any additional comments?

Interesting listen. I am always interested in learning more about how the financial world works.