7 Best Books About Business Failure That Teach You the Value of Success (With Goodreads reviews)

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Should you read books about business failure? Oh, absolutely yes! If you want to be realistic about business success, then books about business failure must adorn your bookshelf! But before I reveal my top picks, here are some fascinating facts about “failure in business!”

Reid Hoffman, the co-founder of employment-oriented service LinkedIn, and an active investor in top global companies such as Airbnb and PayPal, tasted failure initially. He developed a social networking and online dating site called the SocialNet. and yes, it eventually failed.

Evan Williams created Odeo, a Podcasting platform, before co-founding the popular micro blogging and social networking service, Twitter. Shortly after Evan formed Odeo, Apple launched the iTunes store’s podcast section, which led to the closure of Odeo.

Kathryn Minshew lost the entire savings that she had invested in PYP Media because of a disagreement between the co-founders of the company. Later in 2011, Katherine and members of her former team founded The Muse, one of today’s leading online career platforms.

From bankruptcy to imprisonment and termination of employment, some of the biggest names in global business have faced serious setbacks.  But they had one thing in common – the “never say die attitude”. They learned how to turn their business failures into great success stories.

Why Do Aspiring Entrepreneurs & Bloggers Need to Read Books About Business Failure?

A 2003 study, in the Academy of Management Review, revealed that aspiring entrepreneurs can learn from business failures only if they understand the consequences of decisions, assessments, inactions, or actions that caused past failures. This learning is only beneficial only if they realize how to apply this knowledge to successfully run their next enterprise. And it can only happen when aspiring entrepreneurs read books about business failures that teach the value of success.

Here I am going to share a list of 7 books that offer great scope to analyze and review failures to leverage favorable outcomes in business.

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What Are The 7 Best Books About Business Failure That Teach You the Value of Success?

Failing to Succeed: The Story of India’s First E-Commerce Company- by K. Vaitheeswaran

At a time when almost no one in India engaged in online transactions, K. Vaiteswaran, in 1999, co-founded Indiaplaza, i.e., India’s first e-commerce portal. Years later, when the e-commerce sector in India boomed, Indiaplaza was shut down despite being a pioneer in this field.

Vaiteswaran’s book, “Failing to Succeed”, goes deep down into the darker side of launching a start-up business, and the innumerable pitfalls that Indian entrepreneurs have to overcome. The book is full of derisive observations, fascinating anecdotes, and some stunning customer insights. And of course, you wouldn’t like to miss those behind-the-scenes happenings in the start-up ecosystem! “Failing to Succeed” unravels the problems that technology start-ups in India face.

buy failing to succeed

This is one of the must-read books about business failure for industry professionals, investors, business school graduates, aspiring entrepreneurs, and anyone interested in India’s fast-growing start-up environment.

A compelling narrative, “Failure to succeed” is all about the search for ways to progress and achieve success, despite repeated setbacks.

Goodreads Review:

Jul 21, 2017 Surabhi Sharma rated it ***** it was amazing

Shelves: 5-star, from-authors-publishers
Failing to Succeed is not a guide book to succeed, it gives an insight into the entrepreneurship and startup. IndiaPlaza/Fabmart came into existence in 1999 as an online retailer when there was hardly any competition in online retail to give them a fight.

K. Vaitheeswaran tells the tale of the rise and fall of IndiaPlaza, India’s first e-commerce company lasted for 14 years. He discloses that an inexplicable set of events that destroyed what could have been a profitable business. He stumbled not only once but many times and trials and tribulations gave him a hard time dealing with business failures and pitfalls. An entrepreneur he was always remained hopeful and stayed till last.

If you are planning to launch a new venture or dream to become an entrepreneur or working in a start-up or a non-fiction or biography reader or a reader looking for a good book or a student. This book is for you.

Fail More: Embrace, Learn and Adapt to Failure As a Way to Success – by Bill Wooditch

“Fail More” is a one-of-a-kind book that suggests its readers learn from their mistakes. According to author Bill Wooditch, learning from mistakes is the only way to ensure that the same mistake is not repeated.

A guide for entrepreneurs and business professionals, the book offers knowledge, and the necessary tools to craft success by embracing every failure, be it large or small.

Fail more one of the must read books about business failure

“Fail More” inspires budding entrepreneurs and offers them strategic actions to convert failures into rewarding gains. Wooditch’s book unveils both inevitable and likely setbacks and also gives readers practical approaches to quick self-judgment.

Freedom to Fail: Lessons from my Quest for Startup Success – by Shabnam Aggarwal

Shabnam Aggarwal, brought up in an Indian immigrant family, moved to India to start her own business. She quit her cushy, high-paying job at Merrill Lynch to chase her passion of bringing a change in the world.

But things didn’t work out as expected. In her book, “Freedom to Fail”, Shabnam narrates her story of recruiting a team of hardworking millennials, raising the initial round of venture capital, and expanding her business to many cities. However, her success turned out to be a short-lived one as everything ended with a bitter failure.

read freedom to fail

The book “Freedom to Fail” delivered powerful lessons to cope with fear and insecurity. It is one of the most engaging books about business failure that tells readers why it is important to fail to succeed in the long run.

Shabnam’s personal experience in “Freedom to Fail” gives aspiring entrepreneurs an insight into how to deal with setbacks, helping them master the art of converting business failures into mega success.

Goodreads review

Jul 12, 2019 Rashid rated it ****: really liked it
If you are depressed from your Current failure (start-up, business, job) – this one is for you

It’s not a business book nor a fictional novel, instead of a mix of both, I loved the way Shabnam put her entire story – she got an amazing style of expressing things. Going through the book was more like I was in her shows and living the moment, there were instances which made me laugh (there were two instances when someone asked her what she to wear) the way she expressed it …I was laughing (One Beat…..Two beats).

Hope to see more books from her. We just get to know more about her continuous struggle, trying to figure out what needs to be done to sustain – ultimately meeting her failure in the end (by closing her only start-up). The book also talks about seed capital, fundraising, pitch deck, product-market fit, go-to-market plan, business plan, where to find investors, bridge round, EBITDA, Business model calculation – but no were in-depth details about the concept.


The Successful Mistake: How 163 of The World’s Greatest Entrepreneurs Transform Failure Into Success – by Matthew Turner

In “The Successful Mistake”, author Matthew Turner has surveyed 163 global business leaders to suggest realistic ways that can help readers quickly and strongly come back from a failure. The book reveals the approaches of some top business personalities whom Turner interviewed personally.

The book features inspiring stories about the world’s celebrated entrepreneurs and business thought leaders. One of them is Rachel Elnaugh, the founder of the UK’s leading gift company, Red Letter Days. Another inspiring personality whom Turner interviewed is the leading visionary and pioneer in online marketing, Mitch Joel. The book also features Chris Brogan, the New York Times bestselling author.

All of them have transformed their greatest mistakes into legacies that still thrive.

the successful mistake one of the good books to read about business failure

One of the most insightful books about business failure, “The Successful Mistake”, reveals a “Seven-Stage Process” for bouncing back from mistakes and failures. 

Matthew Turner’s book aims to help aspiring entrepreneurs identify and rectify mistakes in the early stages.

Goodreads review:

Mar 01, 2017 Shana Rhinhart rated it ***** it was amazing

It is not often that I read a book where I learn something valuable on every page. Matthew explains in down to earth terms the rise and fall path of mistakes and what type of mind set you need to turn them into fantastic learning experiences that make you a better person. He interviewed over 163 Entrepreneurs who had risen in their fields and made some colossal errors and how they overcame the fall out to rise even higher. They describe in detail what it took mentally and emotionally to overcome and transform their inner landscape via understanding their failures.

I thought this would be a quick read but I was wrong. I took me almost two weeks to read it. It took so long because I needed to digest what I was reading and then self reflect. Matthew does not suggest I do this, I took it upon myself and I am grateful I did it.

The benefits are amazing. I now look at employment, employers and what to look for as a company expands in totally different ways. I don’t want to give you any more spoilers than that. I was so impressed that I joined his facebook group and talk with him weekly! I am seriously impressed and have made a life long friend in the process!



how to fail at almost anything

How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life – by Scott Adams

Before you read the best books about success, you must check out the story of Scott Adams who failed in a lot more things than anybody else! And then Adams achieved extraordinary success from a regular office worker to one of the world’s best-known comic strips creator!

Adams, in his book “How to Fail at Almost Everything and Still Win Big”, shares details about converting failures into lasting success, and his road to fame, including his big investments, his inventions, and corporate career.

“How to Fail at Almost Everything and Still Win Big” includes helpful and unique ideas to recover from failures and use mistakes as a stepping stone for victory.

Goodreads review:

Jan 14, 2015 Stefan Kanev rated it ***** it was amazing
This book is awesome!

Some context first: when I got this book, I had no idea what it was about. I just saw a book from Scott Adams, author of one of my favorite comics (Dilbert) and thought “It might be very interesting to read a book by this guy”. It remained on my shelf for a few months and eventually I was bored and started reading it. And I really, really liked it.

It’s part self-help, part autobiography. Adams tells a couple of personal story and outlines his personal view on life. He invites readers to not treat his words as an advice, but as a data point to form their own opinions. He makes some very nice points that resonate with me:

* Systems are more important than goals. Chasing after goals is hard and risky. Instead, it is better to set up a system and follow it.
* The most important metric is personal energy. One should not optimize for getting stuff done, but for feeling energetic as much as possible.
* Diet and fitness are really important. If you have those right, things fall into their places more easily.

Even if you take just 2% of this book, it’s still worth reading it. It makes some very good points. And it’s very enjoyable to read.


WTF?! (Willing to Fail): How Failure Can Be Your Key to Success – by Brian Scudamore

One of the must-read books about business failure, “WTF?! (Willing to Fail)” talks about different emotions, such as joy, excitement, sadness, and disappointment, that entrepreneurs are likely to face.

Author Brian Scudamore, in “WTF?! (Willing to Fail)”, takes you to a thrilling entrepreneurial journey that teaches you how to overcome obstacles and succeed.

willing to fail

The book, covering 30+ years of Scudamore’s experience, is full of engaging stories. These stories intend to give readers practical lessons to be applied in their entrepreneurship endeavors.

WTF?! (Willing to Fail) also encourages readers to adopt strategies to deal with challenging situations. The ultimate lesson that the book offers is how to use failures to turn around business for better.

Goodreads review:

Nov 01, 2018 Lara rated it ***** it was amazing
A great read, front to back. I thoroughly enjoyed hearing about Brian’s experiences on the way to the top. If only we could all be so positive about our “failures”, learning along the way. My Dad used to say there are no problems, only opportunities. Clearly, Brian and my Dad were onto something.
Oct 31, 2018 Tessa rated it ***** it was amazing
Every entrepreneur should read this book, whether you are aspiring to own your own business or have already taken the plunge. It is lighthearted enough to laugh along with but the tricks and tips will last you a lifetime of business ownership. Highly recommend!!

Failing Forward: Turning Mistakes into Stepping Stones for Success – by John C. Maxwell

It is arguably one of the most popular books about business failure to read. Why? Because the book discusses all the common business mistakes that startup entrepreneurs often commit. It reveals the secrets of going beyond failure and utilizing it as a springboard to achieve success.

Elaborating on the main reasons why people fail, John C. Maxwell’s book fluidly highlights the difference in attitude between the average people and achievers, in responding to crises and failures.

“Failing Forward: Turning Mistakes into Stepping Stones for Success” is an eye-opener for entrepreneurs who easily get affected by fear of failure. It clearly states that there are many things to learn from both positive and negative experiences.

Failing forward

The book is like a reference tool for aspiring entrepreneurs, who are looking for inspiration and strategies to transform big failures into bigger achievements. 

Goodreads review:

Aug 08, 2013 Greg Frucci rated it ***** it was amazing  
Shelves: wisdom, leadership
I began reading this book wondering why a mentor of mine suggested that I read it in the first place. I began the first few pages with the attitude of “yeah, yeah, yeah…I know all this stuff already…my Mentor obviously has no clue who I am.” I kept reading, then the note taking began…big-time. Hahaha…oh the humility I thought I possessed.

We have all heard the cliches before. The ones like, “we learn from our mistakes”, etc. Yet, do you have an action plan in place for truly learning and moving forward? I didn’t, but I do now. “Failing Forward” is not a collection of simple-minded cliches that only people in woo-woo land will relate to. “Failing Forward” is a fantastic read, which if you have the courage to admit your own failures in Life…and you have them…then this book will assist you focus on the benefits of failures, moving along a path to ultimate success in your endeavors. Just remember this…you must be willing to accept responsibility for your own actions and take ownership of your failures…meaning, stop blaming others. If you insist on partying it up at the local “Look at what Life has done to me” ale house, then don’t bother reading this book, you are too weak to handle reality. On the other hand, if you wish to hone your skills in the realm of taking a Leadership role in your own path of Life, then buy this book…it is a must read.

I’m giving this book 5 stars because of the actions I am taking along my Life path from reading “Failing Forward”…yeah, it has had a sustained impact. Oh, and I’m giving the Mentor who told me to read the book five stars as well. Good call, Chris.

To Conclude

According to Colin R. Davis, “The road to success and the road to failure are almost exactly the same.” And he is quite correct in his observation! However young entrepreneurs pursuing success often fail to realize this simple truth.

If you are already running own venture or planning to do so, then you should check out the above mentioned books about business failure.  And I am sure you will notice a major shift in mindset. These books will definitely change the way you perceive business failures. Setbacks that previously made you depressed, will now motivate you to learn from your mistakes and act positively!

Would you like to add any new books to the list? Drop me a line and I will definitely consider it.

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