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Heads I Win, Tails You Lose: A Financial Strategy to Reignite the American Dream

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Conventional financial mindsets are failing too many people. We save, invest, and borrow the way Wall Street, banks, and the financial media tell us, but we are left unprepared for market losses, financial hardships, and retirement. The rules of money and financial well-being have changed, and those who follow them are achieving staggering results. 

In Heads I Win, Tails You Lose, CEO and financial strategist Patrick Donohoe shows you how to embrace a new way of thinking, sharing with you financial secrets used by the wealthy to navigate the rapidly changing economy as well as financial options to help you win no matter what and reach the true American Dream: financial freedom. 

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--advice that will empower you to take back your financial future, exit the rat race, and live a life you love.

338 pages, Kindle Edition

Published July 20, 2018

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5 stars
55 (47%)
4 stars
36 (31%)
3 stars
16 (13%)
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Displaying 1 - 18 of 18 reviews
Profile Image for Joost Nixon.
209 reviews11 followers
July 5, 2023
It’s a lengthy sales pitch, using fear and caricatures to make the case. Too bad, because there are interesting bits. But they are bits.
Profile Image for David McClendon, Sr.
Author 1 book23 followers
August 9, 2018
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If we had to sum up the book Heads I Win, Tails You Lose: A Financial Strategy to Reignite the American Dream by Patrick H. Donohoe in just one word, that word would be “Refreshing”.

This book is refreshing because the author isn’t one of those One Trick Pony authors. You know what I mean. If you read a book on real estate investing, the author talks about how great an investment real estate is and how bad every other investment is. Donohoe doesn’t do that.

The author does tell us about how different investments actually fared over the years, and how his plan of using insurance to steady out the cash flow is not an “or” investment, but an “and” investment. In other words, his method is a part of a good investment strategy.

One of the really great things about this book is that readers are given the history of different investments, why they were created and how they are being used today. He gives his readers the history of the insurance industry and how safe it actually is.

By now, we have read multiple books on investing which really turn out to be sales brochures for a particular company and really expected this book to turn out the same way. The author’s company is mentioned a few times but, unlike most other books, he actually tells his readers how they can find this information for themselves, but emphasizes that his company is there to help. He invites us to use free tools on his website.

We give Heads I Win, Tails You Lose: A Financial Strategy to Reignite the American Dream all five stars. We have over 53,000 books here at McClendon Villa waiting to be reviewed. This book makes the extremely short list of books that will become a permanent part of our library. Of course, the Holy Bible is one we would not part with. Other than that, our list has now grown to a total of three books.

These books are: Master Your Cash Flow: The Key To Grow And Retain Wealth by Albert J. Zdenek Jr CPA/PFS, My Years with General Motors by Alfred Sloan, and now Heads I Win, Tails You Lose: A Financial Strategy to Reignite the American Dream by Patrick H. Donohoe.

We think it is refreshing to see an author not promote his idea as the only tool in the toolbox. We think you will, too.


We were sent a complimentary copy of this book. We are under no obligation to write any review, positive or negative.

We are disclosing this in accordance with the Federal Trade Commission's 16 CFR, Part 255.
Profile Image for Mary Ann.
316 reviews34 followers
March 10, 2019
Never having been taught much about finances, I found Patrick Donohoe's book Heads I Win, Tails You Lose not a dry 'how to' book, but an interesting commentary, history, and suggestion of how one can retain and build personal wealth. Much to consider with sound advice.
Profile Image for Joey.
72 reviews
January 18, 2022
SKIP! Do Not Read This Book! DO NOT!

There are maybe - MAYBE - four intelligent sentences in here. If I could give zero stars, I would. I think the rave reviews are planted and if not, those folks are swindled beyond belief.

I kid you not, there are ads in this book for Donohoe’s company. After two showed up right before the 200 page mark, I almost just put it down.

Donohoe assumes all readers are idiots (which he must, I don’t blame him) but he also assumes they know enough about finances to understand the concepts he’s talking about but not intelligent enough to understand that his scenarios are wildly inaccurate, present unrealistic plots and ultimately are twisted into saying “I’m smart, you’re dumb, I’m big, you’re little, I’m right, you’re (a resounding) wrong!” With a title like HIWTYL, I guess I should’ve known better.

Insurance is an interesting tactic and I could see a smidge of how it could work, the problem is that Donohoe focuses on those who are already wealthy. Us lower, lower-middle or just middle class folks aren’t a thought in his head. The parts of the books are as follows: (1) I’m rich and so are my friends, that’s why you should buy my product; (2) everything you’ve been told is a lie and the people that are using those strategies and it’s worked for them - they don’t count; (3) 100 years ago there were a bunch of wealthy families, so you can be wealthy now too; (4) complete and utter nonsense (still I’m going to talk about really rich people though so you’ll buy my stuff).

Do not waste your time or money. I got this second hand (thank god!) and I usually keep all the finance books I read (some have great references for later). This one, I’m not keeping but I’m also considering burning it so no one else has to deal with it. Recycling even seems like a mercy.

Instead of reading this nonsense read The Barefoot Investor: The Only Money Guide You’ll Ever Need by Scott Pape.
Profile Image for John Blackman.
94 reviews16 followers
August 25, 2020
This is a book about using life insurance as a tool for building wealth. It's a giant lead magnet for the author's advisory services, but that being said it is an excellent source of information on how to manage your money in a way that helps you sleep at night knowing you have a rock solid plan. So in no way should that diminish the value of this book.

I agree with most of the tenants in this book and feel that is is overall good advice for your average investor looking to build wealth and have a retirement that isn't dependent upon social security. Life insurance can be a critical part of your plan. Turns out only 9% of people carry such a policy. It is a great tool for investing in real estate too.

Patrick makes the book more fun to read than your policy documents, so it won't put you to sleep by page 2. If you are into personal finance and want to become a master of your money this book is a good one to download to your brain. There are some great tools in here that you can apply to your strategy.
Profile Image for Mark Manderson.
614 reviews38 followers
June 22, 2024
Been learning about whole life insurance with Paid up options as I’m brand new to this world and have only heard negative info about them.

This book really helped explain many of the misinformation I’ve heard.

Here are my top takeaways:

Controlling your financial life is TRUE FREEDOM

THE PERPETUAL WEALTH STRATEGY:
The PUA is added to the whole life policy to create the dynamic of a single premium policy since TAMRA was passed in 88.
7 year pay test was developed to make sure you can pay 7 years into the death policy so don’t abuse as a tax shelter
ECONOMIC VALUE ADDED (EVA): Ise WMA like a bank for loans while making interest
SPLIT DOLLAR ARRANGEMENT (pg 273): Fund a policy on a key employee by lessening the tax burden
Profile Image for Christopher.
320 reviews13 followers
November 20, 2021
Great book for those beginning the journey to financial freedom. Written in clear and simple prose, Donohoe lays out an unconventional case to build personal wealth. It is a simple framework: take control of your finances, establish passive income, and discover a profession that gives you purpose.

There are plenty of details but I found the concepts behind the framework compelling. For example, you must have a growth mindset to generate wealth. Its not about wining or losing but about learning when you fail. Winning, Donohoe explains, is mindset + experience + tools.

For those with an interest in taking ownership of your finances instead of outsourcing, this is a good starter read.
2 reviews2 followers
January 29, 2019
This book will help expand your financial knowledge by exposing you to strategies you may not be familiar with. I encourage anyone interested in growing and protecting their wealth to read this book.
Profile Image for Skip.
19 reviews3 followers
December 14, 2019
great alternative to “modern wealth building”

Proposes an interesting alternative to “modern wealth building” strategies. A bit of delayed gratification today can pay big dividends in the future.
Profile Image for Marden Morales.
1 review
May 12, 2020
Reread Material

This is the life insurance book I've been looking for. It articulates the benefits of IBC when designed correctly so well. It's definitely one I'm going to go back and reread and reference back on.
Profile Image for Antonio Vargas.
52 reviews1 follower
July 18, 2019
WOW! What a great book. Patrick Donohoe has the formula to reignite the NEW American Dream.
Profile Image for Sándor Lau.
Author 2 books4 followers
June 21, 2021
I tried so hard to understand infinite banking for three other books and didn't know. After this, I understand. Simple explanation!
Profile Image for Joshua Barton.
19 reviews
July 9, 2021
New approach

Many ways to skin a cat. His approach to wealth management has me reconsidering most of my previous understanding. I will at least change how I hold my liquid assets.
Profile Image for Mohamed Abdelwahed.
54 reviews
August 13, 2023
A friend of mine gave me this book, he said I would get something out of it and I did. I really enjoyed Patrick’s writing style and the flow of the book. It is also neat that he offers additional credible sources to further expand the reader’s knowledge on topics covered as you go along. Very informative read that will make you reconsider your finances to improve its health in my opinion.
Profile Image for Douglas Larson.
479 reviews22 followers
January 8, 2022
Did not finish. Not interested in the author's long winded background about how he explored the financial realm.
Profile Image for Cory Wallace.
524 reviews3 followers
April 1, 2025
This is great book which lays the foundation for building a solid financial system. Anyone who wants to improve their financial situation should read this.
Displaying 1 - 18 of 18 reviews

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