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Winners Dream: A Journey from Corner Store to Corner Office

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In the pantheon of CEOs, few people have the visibility, charisma and hunger of Bill McDermott. His career is a classic story of ambition and drive: from the hard-knock streets of his youth in Long Island, to his first forays in business behind the counter of a deli he bought and then operated at the age of 17, to his extraordinary rise through the Xerox Corporation where he pleaded for his first job, to his emergence as the co-CEO of one of the most celebrated and admired global companies of our age. His stories - at turns hilarious and moving, but always inspiring - offer invaluable lessons in self-direction, management and leadership.

336 pages, Hardcover

First published October 7, 2014

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Bill McDermott

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Displaying 1 - 30 of 98 reviews
Profile Image for Melanie.
920 reviews63 followers
October 9, 2014
I received an uncorrected proof copy of this book in a First Reads contest.

The title of this book annoys me. If it's a personal memoir, shouldn't there be an apostrophe in "Winners," if he's referring to himself as a winner? Or is he trying to say that he's lived a life that is the stuff of dreams of all people who are winners? Or he belongs in the winners circle? I realize it's a little thing, but it's a little thing that stares me in the face every time I look at the cover. Goodreads currently calls this book "The Dream," which, while uninspired, is less confusing than the actual title.

McDermott is clearly a salesman, and this book reads like he tried to cram his resume into 300 pages. It's a lot of "look at how awesome I am" and "look at how I created/salvaged/turned around this business and came up with these innovative ideas." He does make a lot of salient business points (more on those later), especially as he recounts his days as a paperboy and the manager of a deli, and how he gets hired at Xerox.

Then he spends the next 100 pages of the book talking about working at Xerox. He was there 17 years, which is about a third of his life, so he should devote a third of his memoir to it, right? I respectfully disagree, because it really bogged down, especially during the late 90s. Also a lot of the specifics of the company weren't that interesting. The TL;DR is that Bill was the best sales associate, then led the best sales team, then went to PR and turned their team from the worst in the country to the best in one year, then moved to Chicago and helped them, then joined the Business Solutions branch of the company and led them to billions of dollars in sales. Then he left because he was as bored as I was getting reading about it. (Not really, but there were differences in POV between him and the rest of the corporate leadership, and he felt it was time to move on.)

After leaving Xerox, he works for a couple of other companies, helps his wife fight through cancer, then lands a gig at the company he's currently running. And of course it was a mess, and of course he makes it a whole lot better with optimism and audacious goals.

So, the key takeaways from this book:
~Focus on the customer. If your customer isn't happy with your product or service, he will find an alternative, and you won't have a job.
~Find ways to distinguish yourself from your competition. Figure out what you can do that they can't (like delivery service or store credit).
~Goodwill gestures can help seal a deal by making your customer feel like you trust them.
~Keep your word.
~Give your employees audacious goals (though I can't think of "audacious goals" without thinking of this rag). It will motivate them.
~Keep alert to the culture around you. Serve food in a food culture, celebrate things that should be celebrated, provide perks and incentives that boost morale and solicit employee feedback about them.
~Build rapport with all people because it makes them feel valued and makes them want to help you.
~Don't discount yourself, your product, or your services. Have faith in their/your value.
~Identify your own goals and aspirations, and check to see if the work that you do is helping you achieve the ends you desire.

This isn't a bad book, but after reading a much tighter (and less personal) book on business and leadership a week or so ago, this one just felt long-winded.
Profile Image for Misha Raina.
2 reviews2 followers
January 31, 2021
I met Bill during the time I worked at SAP. It was my fifth day and we had an all hands meeting where I posed him a question. In addition to answering my question, he invited me to the stage, congratulated me on my new job and hugged me. He is the kind of leader every employee dreams of. A beautiful, inspiring and extremely well written book with wonderful insights on life, leadership and strategy.
1 review
September 28, 2018
The narrator of this book is very irritating and practically the definition of a humble brag. He surely has self-serving bias where he attributes all success to his own hard work and any mistakes or failures to external factors. His story is very generic and not worth the time. Some chapters are written incoherently without any connections between short stories.
Profile Image for Bill Kenney.
15 reviews21 followers
December 5, 2018
I saw Bill speak this year at Marketo Summit. He owned the stage and his presence was so calm but impactful. Something I strive to be one day. I had to buy and read the book. His work ethic and background resonate with my mindset so I enjoyed the story 👌
Profile Image for Kirtikumar.
2 reviews5 followers
January 3, 2019
As I was reading through the book, I was living the story that Bill has to share with us. The narrative is compelling and you will get hooked onto it. The journey from a paperboy to leading the world's largest business software provider, is fascinating. A must read for established and budding leaders. I feel the book would have done justice to the story if it was released in parts rather than in one single book.
Thanks for inspiring Bill !
Profile Image for Jess.
27 reviews4 followers
June 13, 2020
📰 The book in 20 words or less:
Bill's memoir of the journey from difficult beginnings to CEO through hard work and dedication.

💯 My rating:
8.5 / 10

😍 Things I liked:
I really enjoyed the first half of the book - I would have read an entire book just about teenage Bill running the deli. The ending (last 20% or so) was really inspirational and I flew through it.

My favourite anecdotes were the story of the slobbery dog playing fetch, and the Christmas party in Puerto Rico. Bill's love for his mother shone through every time he talked about her - heartwarming.

Bill places a really strong emphasis on family-like culture, and having experienced "big business" corporate culture myself, I completely agree with him.

😒 Things I didn't like:
In terms of business mentors and heroes, there weren't too many women mentioned - though this is almost certainly a reflection on work culture and evolving gender roles during the 80s-90s and not a reflection on Bill himself.

I did find the middle section a little dry in places (specifically between being senior at Xerox and before joining SAP). It seemed a little less personal than the rest of the book and hence more difficult to read.

Some of the grammar choices were a little odd to me, especially the tense changes at the beginning of some chapters which I wasn't a huge fan of, though that's just personal preference. There were also a couple of typos here and there in my edition of the eBook.
Profile Image for Arun Pc.
39 reviews
April 1, 2019
This book is partly motivational and partly about how to climb the corporate ladder. It is an excellent "road map" for any salesperson or account manager. It has excellent examples of how Bill got his bosses, colleagues, and customers to trust him. Bill exemplifies a model sales leader. Once a salesman, always a salesman. He shows how customer centricity and optimism are the most important traits in a sales career. There are many examples of how got his dream positions at various companies. These are the good parts.

There are a few parts in the book that I didn't quite enjoy. Its all about Bill and more Bill, more than I expected. Few things seemed to be overly dramatized and many things seemed all overly rosy. The day to day challenges and setbacks of an enterprise business are briefly mentioned while the grand extravaganza and pageantry are overemphasized. This is not necessarily a bad thing as this book is meant to motivate you to follow the winner's dream.

my 2 cents.
77 reviews7 followers
April 7, 2019
It is not demanding to read. Works perfectly in audiobook format. A really interesting journey of the leader. Especially the first chapters were interesting. I would give 3* for later chapters.

I particularly liked the author's approach to cynics:
I will tolerate the skeptics, but not the cynics. Being a cynic took no courage, and cynics certainly weren’t dreamers. Worse, they were toxic, diluting the optimism that made people believe they could make the impossible possible.

8 reviews1 follower
April 11, 2020
Buku ini sangat bagus, menceritakan bagaimana perjuangannya dari 0
Profile Image for Justin Tapp.
704 reviews89 followers
December 2, 2014
Winners Dream: A Journey from Corner Store to Corner Office
I received an advanced copy of this book from Simon & Schuster via Goodreads for the purpose of reviewing. Opinions are my own.

If you've read Peter Thiel's Zero to One this year, then you'll note that McDermott is a Peter Thiel character-- one in which hard work and determination determine the outcome rather than luck. It's a story of someone who worked hard for success and got everything he ever wanted and more. McDermott writes "my humble hope is that my book furthered the pursuit of your own winner's dream."

Still, the SAP's CEO benefited from the luck of having parents who were always supportive and encouraging optimists. His mother always tells him "you can be whatever you want," and he believes it. His father is a coach and McDermott learns coaching and teamwork lessons from him. It's a very stable home, albeit not a wealthy one. McDermott does not delve into much of the difficulties or any conflicts with siblings. No personal sins, regrets, heartbreaks, etc. show up in the book. As such, it's quite shallow personally. The deepest he gets emotionally is enduring his wife's breast cancer and the death of his mother (fairly recently). He alludes to some sort of faith, but it seems opaque and not essential to his person.

But at least it's a book on leadership and management by a leader who has both led and followed. It's a solid look at corporate culture and how the right leader with the right message and personal integrity can galvanize support and motivate people to perform for a cause greater than themselves. My issue is that the cause is pretty much the corporation's sales and the individual's personal achievements. What good is it a man to gain the whole world and yet forfeit his soul? (Jesus).

Here's a look at the timeline:
McDermott was born into a lower middle class family, his father a welder. They moved from various apartments into a small home in Amityville, a home which often flooded. McDermott is a serial entrepreneur starting as a paper boy then as an ambitious stock boy for a grocer. He's willing to take on risk, he took out a loan to purchase a deli and leads it to greatness. There is very little mention of the overall economy during his formative years and I suspect he dodged a few economic bullets; his risks seemingly all paid off handsomely.

After attending a local college, he essentially talks his way into an entry-level sales job at Xerox (about the time David Kearns comes on as CEO with a new focus on quality), then leads Xerox in sales for the next two years. He is tasked with leading Team F at Xerox, expanding sales in a new territory and taking that region to #1.
McDermott travels on his salespeople's calls, coming up with innovative ways to motivate but not breed competition. He constantly focuses on how it's a team game. Once one employee has hit his sales target and earned his vacation/bonus, McDermott assigns that employee to work with another until everyone hits their targets.

McDermott then gets asked to look at the Puerto Rico/Virgin Islands branch, which is 64th in the world for Xerox and in bad need of a turnaround. He moves his family there, aggressively learns Spanish, while creating a new culture in the office. He takes the region to #1 in sales growth, again being the "winner," as he sees it. Xerox moves him to Chicago to turn that region around, which appears to be one of the more difficult tasks in the book. As he works his way up the corporate ladder, he begins to chafe under the traditional Xerox mentalities that he feels is holding the company back. He is constantly reinventing Xerox's marketing in his own regions/departments, pushing the envelope of their business model.

I looked up Xerox's stock price during this period:

- relative peak of 11.63 on 10/3/80.
- bottoms at 4.56 in 8/6/1982. (Kearns takes over as CEO in 1982, just before McDermott is hired.)
In 1983- Xerox buys Crum & Forster, starts Xerox Financial Services in 1984. McDermott later cites this as a bad move for Xerox.
- climbs to 14.11 8/21/87
- Stock tanks again to 4.85 10/26/90
- Rockets through the 90's to 62 on 1/29/1999, around the time McDermott finally left.


After McDermott jumps ship at Xerox, he ends up at Gartner and another company before landing at SAP America. He is recruited to turn the business around in 2002, and establishes his own vision for the company in 2003.
- SAP stock price bottomed at 10.28 on 10/4/02.
- Was 42.30 on Jan 2, 2004. This represents McDermott's value added. Under his leadership, the company broke a years-long streak of not hitting its quarterly revenue target.

At SAP, conflict arose among managers who couldn't live up to McDermott's new expectations, or just didn't like the job. People who didn't buy in left. 85% of his leadership team moved on. So, McDermott simply taps his own network to replace them, demonstrating the importance of building relationships and not burning bridges.

In February, 2010 he is named co-CEO and successfully co-manages the company with his counterpart friend. This is post-financial crisis and the company needs another turnaround. Like most tech companies, SAP lost most of their share price, as companies became scared to invest in new fields. McDermott is determined to embrace the Cloud and makes strategic mergers with other companies. "Trust is the glue" with the CEOS of acquired companies.

McDermott finally became sole CEO in May, '14. Recent press releases state that SAP is cutting about 3 percent of its 67,000 workers, or about 2,000 jobs as McDermott repositions it to develop more cloud-computing software. The company plans to hire enough new people to offset the cuts.
The key takeaways can be found as the subheadings within the chapters, which together reads like a compilation of every leadership text ever produced.

I have copied and pasted this list from someone else's review (with my additional comments in parentheses):
~Focus on the customer. If your customer isn't happy with your product or service, he will find an alternative, and you won't have a job.
~Find ways to distinguish yourself from your competition. Figure out what you can do that they can't.
~Goodwill gestures can help seal a deal by making your customer feel like you trust them. (This may mean bending the rules of corporate policies)
~Keep your word. (Trust is the glue that binds organizations and partnerships together).
~Give your employees audacious goals, it will motivate them.
~Keep alert to the culture around you. Serve food in a food culture, celebrate things that should be celebrated, provide perks and incentives that boost morale and solicit employee feedback about them.
~Build rapport with all people because it makes them feel valued and makes them want to help you. (ask "How can I help?" of both clients and co-workers).
~Don't discount yourself, your product, or your services. Have faith in their/your value.
~Identify your own goals and aspirations (and don't settle for a path that takes you away from these).

The importance of inter-departmental communication is also highlighted. You can't have sales people out promising something that your engineers and customer service can't deliver. McDermott found the red tape in order processing and human resources at Xerox maddening for this reason. Bureacracies are hard to manage.

I learned quite a bit about Xerox and a little about SAP. McDermott gave good examples of how he learned from other leaders, but generally he had no problems working for the bosses he had because they saw his aggressive energy and "let me do my thing."

I recommend this book as an example of leadership and good management practices. I would give it to individual students to show them what is possible. I would not assign it for a class or use it as a case study. In all, I give it three stars out of five.
Profile Image for Heidi Angell.
Author 12 books211 followers
August 9, 2021
I struggled at first, as I expected this book to be less memoir-like and more of a guide to success like The Oz Principle. IDK why, perhaps the "A global CEO's life lessons in sales, motivation, and leadership" just felt like the book would be more focused on how to achieve success and not so much on the stories that shaped this man's life in particular. That's what happens when you grab a book at random from a book trade.

While this is a classic tale of rags to riches and starts with a lot of stories from his childhood that shaped who he is today, there were a lot of great nuggets of wisdom throughout that one can use to guide one's own journey of success.  Each chapter starts with a quote from a famous person that sets the tone for the chapter. I appreciated a lot of his childhood experiences and can relate to the struggles.  The messages of optimism he experienced with his mom are fantastic. His shared experiences with his first jobs are relatable to an older generation. The drive to improve is a message that really resonated with me.

I am curious how much of the greatness of this book is because a certain generation can relate to it and anyone in sales/ marketing for more than 10 years would be able to relate. I cannot help but wonder if a younger generation could glean much from it and what they would get. Definitely encouraging Little Man to read this next and see what he gets from it as he is in his senior year of high school and at a different level.

My favorite message in the book is that you have to enjoy the journey to success and keep adapting and adjusting your goals as you go through life. That really struck a chord as I am going through my own priority shifts.
Profile Image for Gedi௨.
162 reviews56 followers
Read
February 17, 2021
PROs
+ American dream story of the self-made CEO from the deli to SAP
+ one of the most articulate CEOs: "Storytelling is one of my favorite ways to simplify the world."
+ emphatic journey to the great leadership
+ book dedicated to the reader: "Thank you for sharing in my journey. My intent was to connect with you on an emotional level through authentic stories. My humble hope is that my book furthered the pursuit of your own winner’s dream."

CONs
- does not have extension or sequel with Bills reflection what he is doing currently at ServiceNow

QUOTE(s) on LEADERSHIP
“You must be proud of whatever organization you choose to work for,“then pour yourself into it completely, and do not let anyone else but you shape your future.”

"Leaders came in many forms, but I had long believed that they shared two undeniable traits. First, they brought others to places no one had ever been. Second, leaders had followers. Basic, but without a vision and without support, there was no leadership, only words."

“People don’t quit companies, they quit managers,”

A leader’s role, however, is not just to dream but to architect dreams into reality.

Profile Image for Zeyuan Wang.
27 reviews
May 22, 2020
This man will prove to you that everything is possible if you dare to dream big and put everything into it.

Coming from a humbling background, Bill has earned himself a privileged life through his substance, confidence and aspirations.

Since young, he understood the importance of satisfying his customers. He has seen firsthand, the power of customer-focused strategy in the success of his small grocery store. His substance has been accumulated through constant trial-and-error, experience and a desire for greatness.

Trust is something he held dearly. Because of the trust of his bosses, he gained the opportunity to prove himself. Because of the believe in trust, he is willing to delegate key tasks to his employees and believe that they will produce the best results.

Dream and you shall receive. The next winner is you.
Profile Image for Shaydy.
117 reviews39 followers
January 14, 2023
Easily digestible wisdom about life goals, passion, mutual success and psychological approaches to business. Admirable strategies and willingness to push the envelope. However, I doubt that even as a child the author had perfect internal confidence and external charisma, and he never fails due to something within his control, so the story seems almost too good to be true. Also, it is packaged as a lesson in hard work, as if anyone who follows his advice will similarly achieve their goals, but even employees he directly mentors cannot reach his level of social skills, quick thinking and balanced boldness. The author seems to seamlessly transition between roles due to useful traits and knows what to do without being taught, which detracts from the book’s efforts at relating to the reader.
9 reviews1 follower
December 28, 2017
Ein wundervolles Buch! Sehr motivierend und inspirierend! Ich hatte die Ehre Bill McDermott persönlich kennenzulernen und kann bestätigen, dass er seine Überzeugungen wirklich so lebt. Er strahlt Bodenständigkeit aus - bei einer großen Präsentation nahm er sich die Zeit sogar dem Fotografen die Hand zu drücken und sich bei ihm für seine Arbeit zu bedanken - obwohl er von seinen Sicherheitsleuten mehrmals auf sein straffes Programm hingewiesen wurde. Das hat mir sehr imponiert und dazu beigetragen, dass ich sein Buch als glaubwürdige Erfolgsanleitung gelesen habe.
Profile Image for Anan Lowell.
20 reviews5 followers
May 22, 2019
Very good biography, a very touching story from someone who start from zero, step to step to become CEO at at the largest business software company in the world. I think it is very rare, a sales person to become a CEO of a big software company. I learn a lot from this book, about sales, about motivations.

When he was asked in his first sales job interview at Xerox after college, “Bill, what’s your dream?”
His answer “Sir, one day I would hope to become the CEO.” He doesn't become XEROX CEO but become SAP CEO.
70 reviews5 followers
August 2, 2019
Cheesy title, great book. This is an autobiographical account of how Bill rose from a working class neighborhood on the south shore of Long Island to CEO of SAP. A great read for anyone who works in a sales organization, however, anyone who deals with other human beings for a living can takeaway something from his story. One of my favorite lines in the book is when he talks about the performance tracking process in place at SAP when he first arrived... He referred to it as "Burger King" spreadsheet where everyone got to track it "your way" I bet no one reading this can relate...
Profile Image for Lisa Wei.
105 reviews
February 6, 2018
Having heard Bill speak before and being blown away by his charisma and confidence, I was interested in reading his personal story. The book shows he's gone through so much in his life starting from childhood, and I appreciate his resilience when it would have been easier to adopt a victim mentality. Picked up some good lessons on leadership, teamwork, sales, and being customer-centric. I especially liked the quotes at the beginning of each chapter.
Profile Image for Derick Le.
37 reviews1 follower
January 15, 2019
Incredible story shared by Bill McDermott. My favorite are all the impactful quotes of each chapter and how relevant they are to his story. Following his journey in life was amazing. From the starting point of his career and business venture with the Deli to the final corner office as CEO of SAP, you can see and feel his determination, hard work and perseverance through tough times. The most important lesson through out is Bill's commitment to excellence and servitude.
383 reviews12 followers
October 27, 2025
Bill's first professional job was selling Xerox machines.

SAP stands for System Analysis & Program development.

SAP became known for its integrated suite of applications for manufacturing, finance and HR. Better control resources which gave rise to the name of Enterprise Resource Planning (ERP) to describe the combination of the 3.

Passion is the differentiator between mediocrity, goodness and greatness.

This entire review has been hidden because of spoilers.
Profile Image for Rahul Sengupta.
5 reviews2 followers
April 5, 2018
Heard an interview of Bill McDermott some time back, was immediately captivated by his ability as an orator and salesman. In the interview, he mentioned his autobiography. This book was what I expected - a leisurely read. It’s about winning despite circumstance, human desires, putting the customer first, and the journey of a salesman to the corner office.
Profile Image for Jack.
21 reviews
September 15, 2018
As an employee of SAP I decided to read this book and the audio file as I wanted to hear Bill tell his story in in own words. On the flight home from our SuccessConnect conference I finished the whole thing...1/2 read, 1/2 audio. I feel incredibly fortunate to work for a company lead man like Bill. He’s authentic. He communicates in a way we all can resonate with - stories.
Profile Image for Julie Candelon.
20 reviews1 follower
February 9, 2019
I saw Bill at Marketo Summit in 2018 and was impressed by his story and executive presence. He seemed confident yet humble, was a great speaker able to win the crowd and shared stories full of wisdom I was dying to absorb. His book is very much aligned with that keynote and gave me food for thought. A good read.
1 review
Read
June 24, 2020
It was a good book. I felt like the last section was rushed through and had less impact than the earlier sections of the book but the overall message was good. McDermott is my CEO and I was happy to see that the values he outlines in this book are consistent with what we see in his actions at work.
107 reviews47 followers
November 16, 2020
Winners Dream is a great business autobiography. There’s value here for you whether you are just starting out or in a senior corporate position. There’s wisdom about making career choices. And there are many nuggets about how to be successful that you can use in business and other parts of your life.

See my full review at:

https://www.threestarleadership.com/b...
Profile Image for Rafael Carlet.
6 reviews
November 7, 2022
Inspiring and easy to read, quick and attached to real-life easy-to-digest facts. My only drawback is that sometimes the narrator seems to brag about his achievements, and it is rare when a situation of failure is described. When this happens, the reason is assigned to an external factor. Overall is a great read to get a grasp on the extraordinary professional Bill is.
Profile Image for Sai Sourabh Patro Rajapatruni.
5 reviews
July 15, 2018
Insightful journey with bill over his childhood to C.E.O. Inspirational read about his childhood hardships to his unwavering dream to be C.E.O . Hardwork, persistence and vision were the key traits to learn from kind BILL.
Profile Image for Felix Wu.
3 reviews3 followers
February 17, 2019
An absolutely astonishing display of leadership and innovation. Bill McDermott embodies the dream of succeeding with pure passion and ambition, proving your doubters wrong and the ability to think outside the box when all odds are stacked against you.
Profile Image for Kass.
134 reviews2 followers
January 27, 2020
Listened to this on Audible, as it is narrated by Bill himself. Really adds to his story to hear his voice. While this book does feel a little sales schmoozy, it also felt pretty authentic to who Bill his. Proud to have him as a leader that I respect.
Profile Image for Lokesh.
9 reviews
March 1, 2020
A highly recommended book for those who want to create impact in their lives and the people around them and in this world. Winners Dream is one of the best books on Leadership and motivation and Bill McDermott is the true leader of consequences. Thank You Bill for your amazing stories.
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