
Heads I Win, Tails I Win
Why Smart Investors Fail and How to Tilt the Odds in Your Favor
Failed to add items
Add to Cart failed.
Add to Wish List failed.
Remove from wishlist failed.
Adding to library failed
Follow podcast failed
Unfollow podcast failed
$0.99/mo for the first 3 months

Buy for $25.78
No default payment method selected.
We are sorry. We are not allowed to sell this product with the selected payment method
-
Narrated by:
-
Sean Pratt
-
By:
-
Spencer Jakab
About this listen
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 LLCListeners also enjoyed...
-
How to Invest
- By: David M. Rubenstein
- Narrated by: David M. Rubenstein, Ray Dalio, Marc Andreessen, and others
- Length: 17 hrs and 13 mins
- Unabridged
-
Overall
-
Performance
-
Story
What do the most successful investors have in common? David M. Rubenstein, cofounder of one of the world’s largest investment firms, has spent years interviewing the greatest investors in the world to discover the time-tested principles, hard-earned wisdom, and indispensable tools that guide their practice. Rubenstein, who has spent more than three decades in the hypercompetitive world of private equity, now distills everything he’s learned about the art and craft of investing, from venture capital, real estate, private equity, hedge funds, to crypto, endowments, SPACs, ESG, and more.
-
-
Only get the audio book
- By Joe on 09-26-22
-
The Revolution That Wasn't
- GameStop, Reddit, and the Fleecing of Small Investors
- By: Spencer Jakab
- Narrated by: Sean Patrick Hopkins
- Length: 9 hrs and 1 min
- Unabridged
-
Overall
-
Performance
-
Story
During one crazy week in January 2021, a motley crew of retail traders on Reddit’s r/wallstreetbets forum had seemingly done the impossible—they had brought some of the biggest, richest players on Wall Street to their knees. Their weapon was GameStop, a failing retailer whose shares briefly became the most-traded security on the planet and the subject of intense media coverage. The Revolution That Wasn’t is the riveting story of how the meme stock squeeze unfolded, and of the real architects (and winners) of the GameStop rally.
-
-
Not a book but a journalist diary
- By srini katta on 02-16-22
By: Spencer Jakab
-
The Fourth Turning Is Here
- What the Seasons of History Tell Us About How and When This Crisis Will End
- By: Neil Howe
- Narrated by: Neil Howe
- Length: 20 hrs and 29 mins
- Unabridged
-
Overall
-
Performance
-
Story
Twenty-five years ago, Neil Howe and the late William Strauss dazzled the world with a provocative new theory of American history. Looking back at the last 500 years, they’d uncovered a distinct pattern: modern history moves in cycles, each one lasting roughly 80 to 100 years, the length of a long human life, with each cycle composed of four eras—or “turnings”—that always arrive in the same order and each last about 25 years. The last of these eras—the fourth turning—was always the most perilous, a period of civic upheaval and national mobilization.
-
-
A little baffled
- By John Coleman on 07-18-23
By: Neil Howe
-
Heads I Win, Tails You Lose
- A Financial Strategy to Reignite the American Dream
- By: Patrick H. Donohoe
- Narrated by: Patrick Donohoe
- Length: 6 hrs and 22 mins
- Unabridged
-
Overall
-
Performance
-
Story
Discover a new method of managing your money outside of Wall Street using private mutual insurance companies who are redefining themselves as the heroic steward of American savings to prosper a new generation of wealth-building tools and techniques. With this book, you will learn the financial strategies that typical advisors, typical financial planners, and the financial media don't dare give.
-
-
Misleading Information!
- By JLP on 11-10-19
-
Principles for Dealing with the Changing World Order
- Why Nations Succeed or Fail
- By: Ray Dalio
- Narrated by: Jeremy Bobb, Ray Dalio
- Length: 16 hrs and 48 mins
- Unabridged
-
Overall
-
Performance
-
Story
From legendary investor Ray Dalio, author of the number-one New York Times best seller Principles, who has spent half a century studying global economies and markets, Principles for Dealing with the Changing World Order examines history’s most turbulent economic and political periods to reveal why the times ahead will likely be radically different from those we’ve experienced in our lifetimes - and to offer practical advice on how to navigate them well.
-
-
Ray Dalio, Chinas New Minister of Propoganda
- By Dudley on 01-04-22
By: Ray Dalio
-
Becoming Trader Joe
- How I Did Business My Way and Still Beat the Big Guys
- By: Joe Coulombe, Patty Civalleri - contributor
- Narrated by: Mark Smeby
- Length: 7 hrs and 33 mins
- Unabridged
-
Overall
-
Performance
-
Story
Joe Coulombe founded what would become Trader Joe’s in the late 1960s and helped shape it into the beloved, quirky food chain it is today. Realizing early on that he could not compete and win by playing the same game his bigger competitors were playing, he decided to build a store for educated people of somewhat modest means. In this way, Joe laid down a blueprint for other business owners to follow to build their own unique shopping experience that customers love, and a work environment that employees love being a part of.
-
-
Many mispronunciations
- By Maria Francesca on 06-26-21
By: Joe Coulombe, and others
-
How to Invest
- By: David M. Rubenstein
- Narrated by: David M. Rubenstein, Ray Dalio, Marc Andreessen, and others
- Length: 17 hrs and 13 mins
- Unabridged
-
Overall
-
Performance
-
Story
What do the most successful investors have in common? David M. Rubenstein, cofounder of one of the world’s largest investment firms, has spent years interviewing the greatest investors in the world to discover the time-tested principles, hard-earned wisdom, and indispensable tools that guide their practice. Rubenstein, who has spent more than three decades in the hypercompetitive world of private equity, now distills everything he’s learned about the art and craft of investing, from venture capital, real estate, private equity, hedge funds, to crypto, endowments, SPACs, ESG, and more.
-
-
Only get the audio book
- By Joe on 09-26-22
-
The Revolution That Wasn't
- GameStop, Reddit, and the Fleecing of Small Investors
- By: Spencer Jakab
- Narrated by: Sean Patrick Hopkins
- Length: 9 hrs and 1 min
- Unabridged
-
Overall
-
Performance
-
Story
During one crazy week in January 2021, a motley crew of retail traders on Reddit’s r/wallstreetbets forum had seemingly done the impossible—they had brought some of the biggest, richest players on Wall Street to their knees. Their weapon was GameStop, a failing retailer whose shares briefly became the most-traded security on the planet and the subject of intense media coverage. The Revolution That Wasn’t is the riveting story of how the meme stock squeeze unfolded, and of the real architects (and winners) of the GameStop rally.
-
-
Not a book but a journalist diary
- By srini katta on 02-16-22
By: Spencer Jakab
-
The Fourth Turning Is Here
- What the Seasons of History Tell Us About How and When This Crisis Will End
- By: Neil Howe
- Narrated by: Neil Howe
- Length: 20 hrs and 29 mins
- Unabridged
-
Overall
-
Performance
-
Story
Twenty-five years ago, Neil Howe and the late William Strauss dazzled the world with a provocative new theory of American history. Looking back at the last 500 years, they’d uncovered a distinct pattern: modern history moves in cycles, each one lasting roughly 80 to 100 years, the length of a long human life, with each cycle composed of four eras—or “turnings”—that always arrive in the same order and each last about 25 years. The last of these eras—the fourth turning—was always the most perilous, a period of civic upheaval and national mobilization.
-
-
A little baffled
- By John Coleman on 07-18-23
By: Neil Howe
-
Heads I Win, Tails You Lose
- A Financial Strategy to Reignite the American Dream
- By: Patrick H. Donohoe
- Narrated by: Patrick Donohoe
- Length: 6 hrs and 22 mins
- Unabridged
-
Overall
-
Performance
-
Story
Discover a new method of managing your money outside of Wall Street using private mutual insurance companies who are redefining themselves as the heroic steward of American savings to prosper a new generation of wealth-building tools and techniques. With this book, you will learn the financial strategies that typical advisors, typical financial planners, and the financial media don't dare give.
-
-
Misleading Information!
- By JLP on 11-10-19
-
Principles for Dealing with the Changing World Order
- Why Nations Succeed or Fail
- By: Ray Dalio
- Narrated by: Jeremy Bobb, Ray Dalio
- Length: 16 hrs and 48 mins
- Unabridged
-
Overall
-
Performance
-
Story
From legendary investor Ray Dalio, author of the number-one New York Times best seller Principles, who has spent half a century studying global economies and markets, Principles for Dealing with the Changing World Order examines history’s most turbulent economic and political periods to reveal why the times ahead will likely be radically different from those we’ve experienced in our lifetimes - and to offer practical advice on how to navigate them well.
-
-
Ray Dalio, Chinas New Minister of Propoganda
- By Dudley on 01-04-22
By: Ray Dalio
-
Becoming Trader Joe
- How I Did Business My Way and Still Beat the Big Guys
- By: Joe Coulombe, Patty Civalleri - contributor
- Narrated by: Mark Smeby
- Length: 7 hrs and 33 mins
- Unabridged
-
Overall
-
Performance
-
Story
Joe Coulombe founded what would become Trader Joe’s in the late 1960s and helped shape it into the beloved, quirky food chain it is today. Realizing early on that he could not compete and win by playing the same game his bigger competitors were playing, he decided to build a store for educated people of somewhat modest means. In this way, Joe laid down a blueprint for other business owners to follow to build their own unique shopping experience that customers love, and a work environment that employees love being a part of.
-
-
Many mispronunciations
- By Maria Francesca on 06-26-21
By: Joe Coulombe, and others
-
The Little Book That Still Beats the Market
- By: Joel Greenblatt
- Narrated by: Adam Grupper
- Length: 3 hrs and 51 mins
- Unabridged
-
Overall
-
Performance
-
Story
Now, with a new Introduction and Afterword for 2010, The Little Book that Still Beats the Market updates and expands upon the research findings from the original book. Included are data and analysis covering the recent financial crisis and model performance through the end of 2009. In a straightforward and accessible style, the book explores the basic principles of successful stock market investing and then reveals the author’s time-tested formula....
-
-
Need the PDF files for a complete product
- By Jim Ashby on 01-16-20
By: Joel Greenblatt
-
The Most Important Thing
- Uncommon Sense for The Thoughtful Investor
- By: Howard Marks
- Narrated by: John FitzGibbon
- Length: 7 hrs and 9 mins
- Unabridged
-
Overall
-
Performance
-
Story
Howard Marks, the chairman and cofounder of Oaktree Capital Management, is renowned for his insightful assessments of market opportunity and risk. After four decades spent ascending to the top of the investment management profession, he is today sought out by the world's leading value investors, and his client memos brim with insightful commentary and a time-tested, fundamental philosophy. The Most Important Thing explains the keys to successful investment and the pitfalls that can destroy capital or ruin a career.
-
-
Five Star Book, two Star Audiobook
- By Johnny on 06-08-15
By: Howard Marks
-
Stocks for the Long Run (Fifth Edition)
- The Definitive Guide to Financial Market Returns & Long-Term Investment Strategies
- By: Jeremy J. Siegel
- Narrated by: Scott Pollak
- Length: 13 hrs and 25 mins
- Unabridged
-
Overall
-
Performance
-
Story
The stock-investing classic - updated to help you win in today’s chaotic global economy. Much has changed since the last edition of Stocks for the Long Run. The financial crisis, the deepest bear market since the Great Depression, and the continued growth of the emerging markets are just some of the contingencies directly affecting every portfolio in the world. To help you navigate markets and make the best investment decisions, Jeremy Siegel has updated his best-selling guide to stock market investing.
-
-
Boring!!!!
- By Frankie on 01-20-23
By: Jeremy J. Siegel
-
Just Keep Buying
- Proven Ways to Save Money and Build Your Wealth
- By: Nick Maggiulli
- Narrated by: Kevin Meyer
- Length: 6 hrs and 21 mins
- Unabridged
-
Overall
-
Performance
-
Story
Everyone faces big questions when it comes to money. Unfortunately, many of the answers provided by the financial industry have been based on belief and conjecture, rather than data and evidence - until now. The hugely popular finance blogger Nick Maggiulli crunches the numbers to answer your biggest questions, and to provide you with proven ways to build your wealth right away. By following the strategies revealed here, you can act smarter, and live richer, each and every day. It’s time to take the next step in your wealth-building journey!
-
-
Good Framework
- By Oz on 08-05-23
By: Nick Maggiulli
-
The Power of Regret
- How Looking Backward Moves Us Forward
- By: Daniel H. Pink
- Narrated by: Daniel H. Pink, Gisela Chipe, Edward Hong, and others
- Length: 5 hrs and 29 mins
- Unabridged
-
Overall
-
Performance
-
Story
Everybody has regrets, Daniel H. Pink explains in The Power of Regret. They’re a universal and healthy part of being human. And understanding how regret works can help us make smarter decisions, perform better at work and school, and bring greater meaning to our lives.
-
-
Powerful, immediately relevant
- By LEE on 02-08-22
By: Daniel H. Pink
-
The Simple Path to Wealth
- Your Road Map to Financial Independence and a Rich, Free Life
- By: JL Collins
- Narrated by: JL Collins, Peter Adeney
- Length: 6 hrs and 38 mins
- Unabridged
-
Overall
-
Performance
-
Story
This book grew out of a series of letters to my daughter concerning various things - mostly about money and investing - she was not yet quite ready to hear. Since money is the single most powerful tool we have for navigating this complex world we've created, understanding it is critical.
-
-
Misleading, heavily biased
- By Cody Peralta on 07-19-19
By: JL Collins
-
How to Lead
- Wisdom from the World's Greatest CEOs, Founders, and Game Changers
- By: David M. Rubenstein
- Narrated by: David M. Rubenstein
- Length: 13 hrs and 6 mins
- Unabridged
-
Overall
-
Performance
-
Story
The essential leadership playbook. Learn the principles and guiding philosophies of Bill Gates, Jeff Bezos, Ruth Bader Ginsburg, Warren Buffett, Oprah Winfrey, and many others through illuminating conversations about their remarkable lives and careers. For the past five years, David M. Rubenstein - author of The American Story, visionary cofounder of The Carlyle Group, and host of The David Rubenstein Show - has spoken with the world’s highest performing leaders about who they are and how they became successful.
-
-
A leadership book devoid of leadership.
- By JD on 09-10-20
-
Austrian School for Investors: Austrian Investing between Inflation and Deflation
- By: Rahim Taghizadegan, Ronald Stöferle, Mark Valek, and others
- Narrated by: Marcus Freeman
- Length: 10 hrs and 14 mins
- Unabridged
-
Overall
-
Performance
-
Story
Insanity seems to rule the financial markets and many investors are driven by delusion and anxiety. Could everything you thought you knew about investing be wrong? The Austrian School’s approach provides the needed respite for investors caught in inflationary treadmills. Conventional investment experts often overlook economic developments, which may become a hazard for mainstream investors. Instead, the Austrian School of Economics has proved itself as an independent approach beyond the interests of politicians and bankers.
-
-
Well worth the listen!
- By Shepard on 08-06-22
By: Rahim Taghizadegan, and others
-
Retire Before Mom and Dad
- The Simple Numbers Behind a Lifetime of Financial Freedom
- By: Rob Berger
- Narrated by: Rob Berger
- Length: 6 hrs and 43 mins
- Unabridged
-
Overall
-
Performance
-
Story
It’s time to claim your financial freedom. All you need is a road map to follow, and you can create a life most people only dream about. A life free from financial stress. A life full of what matters most to you. In Retire Before Mom and Dad, you’ll learn how to unlock the superpower inside of you that is capable of transforming almost any income into lasting financial freedom.
-
-
Excellent personal finance book!
- By Chicago on 09-15-19
By: Rob Berger
-
The Motley Fool Investment Guide
- By: David Gardner, Tom Gardner
- Narrated by: David Gardner
- Length: 2 hrs and 55 mins
- Abridged
-
Overall
-
Performance
-
Story
Completely revised and updated with clear and witty explanations, The Motley Fool Investment Guide deciphers all the new information - from evaluating individual stocks to creating a diverse investment portfolio. Also: The Motley Fool You Have More Than You Think.
-
-
Every first time investor should listen to this !
- By MRinaldi on 02-16-20
By: David Gardner, and others
-
The Warren Buffett Way
- 3rd Edition
- By: Robert Hagstrom
- Narrated by: Stephen Hoye
- Length: 10 hrs and 31 mins
- Unabridged
-
Overall
-
Performance
-
Story
Warren Buffett remains one of the most sought-after and watched figures in business today. He has become a billionaire and investment sage by buying chunks of companies and holding onto them, managing them as businesses, and eventually reaping huge profits for himself and investors in Berkshire Hathaway. The first two editions of The Warren Buffett Way gave investors their first in-depth look at the innovative investment and business strategies behind the spectacular success of living legend Warren E. Buffett.
-
-
Suggest getting the print copy.
- By Kevin Martin on 10-25-15
By: Robert Hagstrom
-
Market Wizards
- Interviews with Top Traders
- By: Jack D. Schwager, Bruce Kovner, Richard Dennis, and others
- Narrated by: Dj Holte
- Length: 14 hrs and 41 mins
- Unabridged
-
Overall
-
Performance
-
Story
What separates the world's top traders from the vast majority of unsuccessful investors? In this iconic financial classic, Jack Schwager sets out to answer this question in his interviews with superstar money-makers including Bruce Kovner, Richard Dennis, Paul Tudor Jones, Michel Steinhardt, Ed Seykota, Marty Schwartz, Tom Baldwin, and more in this audiobook.
-
-
THIS IS NOW A NEW NARRATION
- By jack schwager on 11-18-18
By: Jack D. Schwager, and others
Critic reviews
What listeners say about Heads I Win, Tails I Win
Average customer ratingsReviews - Please select the tabs below to change the source of reviews.
-
Overall
-
Performance
-
Story
- Rob Barry
- 12-20-18
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!
Something went wrong. Please try again in a few minutes.
You voted on this review!
You reported this review!
1 person found this helpful
-
Overall
-
Performance
-
Story
- Matt M.
- 10-18-16
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.
Something went wrong. Please try again in a few minutes.
You voted on this review!
You reported this review!
1 person found this helpful
-
Overall
-
Performance
-
Story
- S. K. Lane
- 04-03-22
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.
Something went wrong. Please try again in a few minutes.
You voted on this review!
You reported this review!
-
Overall
-
Story
- David
- 08-18-16
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.
Something went wrong. Please try again in a few minutes.
You voted on this review!
You reported this review!
1 person found this helpful
-
Overall
-
Performance
-
Story
- P H F
- 08-01-16
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.
Something went wrong. Please try again in a few minutes.
You voted on this review!
You reported this review!
1 person found this helpful