Sharing my favourite 25 learnings from the book, “Winners Dream: A Journey from Corner Store to Corner Office” (2014) by Bill McDermott.
1 | The best part of you is you. Just be you.
My mom, tucking me in and insisting, “Bill, the best part of you is you.”
because my mother repeatedly told me, often in the same breath, that “anything worthwhile in life does not come easy” and that “you have the potential to do anything you set your mind to.”
I take a seat and a deep breath and hear my mom’s voice: “Bill, there’s no ceiling on you. There’s nothing that you cannot do. Just remember, be yourself, that’s the most important part of you. Just be you.”
2 | Simplicity provides clarity, complexity hides clarity.
Simplicity was not about being small, simple-minded, or easy. On the contrary, simplicity was sophistication in disguise. Simplicity prioritized. Simplified ideas invited everyone in and freed people to see the world from a sharper but shared lens. Complexity, on the other hand, could intimidate and confuse. Tangled language and multilayered strategies gave way to a briar patch of indecision. Arguing pros and cons was important, and could be enjoyable, as long as doing so did not overcomplicate the issues. In business, endless discussion could kill a company; healthy debate birthed action. Through my conversations with Hasso, I knew that he, too, was a strong believer in the power of simplicity, particularly when it came to innovation. “If you cannot articulate in a simplistic form your real purpose and intention,” he had said, “you will have difficulties developing something meaningful and efficient.
3 | The more daring the target, the higher people rise.
I needed to get everyone’s mind to a place where the dream seemed so impossible that it was exciting to pursue. I deliberately overshot. For more than a decade now, I’d watched teams rise to the expectations set for them. The more daring the target, the higher people rose. Big numbers got people’s attention and heightened their belief in their ability to achieve something deemed impossible.
4 | Winning is not individual success, it is the team’s triumph.
“The only thing I need you to do tonight is stop that kid Chase,” Dad explained. I was in fifth grade, and this kid Chase was the top scorer in the Catholic Youth Organization (CYO) league, plus a good six inches taller than me—just huge. “If he doesn’t score a single point, we win the game. Better yet, if he scores fewer than ten, we win the game.
But if you try to outscore him, Bill, we will lose. So your mission tonight is to sacrifice your own scoring. Just make sure Chase doesn’t make any baskets.” I didn’t argue. My dad inherited his fierce will to win from his father, pro basketball player and Hall of Famer Bobby McDermott.
5 | Teams, not stars, win games.
Dad taught me that winning required knowing my opponents’ strengths and weaknesses. “It’s not about you,” he said, “it’s about understanding them.” Beating someone like Chase was less about exercising my skills than about shutting down his skills. During that final game, I put my ego on hold and followed my dad’s advice. In the end, Chase and I scored only four points each, and my team took home the trophy.
My father’s second obsession was teamwork. He loved to win, yes, but he also understood that teams, not star players, won games. “Winning is not about how many points one player scores, but about the team winning.” This was my father’s mantra, and why he had us practice passing the ball more than dribbling or shooting. Dad preached selflessness for the good of the group, and that none of us was as talented as all of us.
6 | Be competitive, never give up, always give it your 100%.
“My father’s greatest asset was his competitive spirit,” my dad, a carnation pinned to the lapel of his suit jacket, told a banquet room full of our family members and basketball luminaries. “Fans, players, coaches, teammates, and opponents—especially the opponents—remember him well. He never gave up. He gave it one hundred percent.”
7 | Victory is not the prize, witnessing greatness is.
Behind my father’s words was a powerful sentiment: the true value of any sport was not winning, but the pleasure of watching great players in action. Living their dreams.
He just wanted great players, wherever they came from. His role was to help us play to our strengths—whether you could shoot, rebound, or defend—and get us to work together as a team.
8 | Listen more than you talk. Seek truth, find solutions.
I think I was a lot more curious and mature than most kids my age, listening more than I talked….The unfiltered exposure to my family’s circumstances taught me that hard work did not always pay off. I also understood that anything earned or given could be taken away: a house, a job, a brother. I developed a bias for truth, especially news no one wanted to hear, because the more I knew, the more quickly I could find a solution instead of dwelling on a problem.
9 | Know your customers, your competitors, yourself.
I was David amid Goliaths. What, I thought, did I have that the Goliaths did not? What could my little deli give people that 7-Eleven and Finast could not? I thought back to how I delivered those newspapers, and I asked myself a simple but critical question: Who are my customers? What did they want other than cheap milk and choices, which my competitors offered? Where could my store add unique value?
Similar to basketball, winning at business was not going to be about me, it was going to be about them. Everything I did had to strengthen my customers’ ties with the deli so that they kept coming back and spending money. If my interests were aligned with their desires, we’d both win. To do things differently, I had to see things differently. Once I knew my customers, what they wanted, and what I was good at, I focused on it relentlessly.
10 | Be interested than to be interesting.
From day one, I knew that sales was about people, not just products. A lot of other salespeople either didn’t realize that, or they didn’t care. I would walk into an office and try to figure out people’s moods, their needs, their desires. Did I have my own agenda? Absolutely. But I had an interest in others’ agendas, too. I wanted to know what mattered to someone standing in front of me; once I connected with people on a more personal level, anything became possible. Over and over, in cold call after cold call, I tried to sense what mattered to people—and do something about it.
11 | Sell value, not products.
Many of my work habits had not changed much over the years. I was as hungry and as hardworking as ever. I still stressed the importance of selling value versus products, I still liked to be in the field, and I monitored SAP’s sales pipelines daily, although now I did so from my iPad.
12 | To get what you want, give others what they want.
To get what I want, I have to give others what they want: performance. Unless I consistently meet and exceed goals and deliver on promises, no one owes me a thing. Passion is important, I know. Passion propels me forward during tough sales days and gives me the courage to take risks. Passion drove me to Stamford. But even if I want something more, I will never get what I want unless I have results to show for all my effort.
13 | Underselling your product and you undersell yourself.
“Undersell your product, and you undersell yourself,” I chant. “Discounting is the easy way out. The loser’s escape hatch.” I do not believe salespeople should lean on the crutch of discounts. Doing so chips away at the trust between a rep and a customer, as well as a salesperson’s top line.
But if salespeople quoted the high price first and then reduced it, the reduction cut revenue for Xerox as well as the salesperson’s commission. Instead of discounting, I believed in selling products for what they were worth. That meant full price.
14 | Always be highly customer-centric.
Customer-centricity tied everything together. As I told Info-World magazine in spring 2003, “Everyone in this company, from executives down to the product line managers and their staff, are spending as much time with customers as they can. We are a totally customer-focused organization.” Who, exactly, are our customers? Who is our base? What do these customers want?
15 | Right by customers, right by business.
The customer was our most important responsibility. If the customer had a problem, we had to fix it—no matter what. Everything revolved around the customer’s needs. Drop anything internal for the external customer. If it’s right for the customer, just do it.
16 | Customers decide your future, not you.
“In the long run, our customers are going to determine whether we have a job or whether we do not. Their attitude toward us is going to be the factor determining our success.” - Xerox founder Joe Wilson
17 | Your success mirrors your customers’ success.
Let’s talk about success. We are successful when our customers are successful. That is it! We have to make our customers successful in the marketplaces as they compete. We must focus all of our energy and our passion on our customers. (1) Accountability. Don’t pass the buck. (2) Professionalism. Professionals are well prepared. They are always on their game. (3) Teamwork. Everything in life that really matters happens because a team of people decides it should. (4) Passion. Passion is that differentiator between mediocrity, goodness, and greatness. Passion is when you will do whatever it takes to step up to the bar and deliver.
18 | Deals are sealed with people, not paper. Trust is the glue.
All of my deals were first sealed with people, not paper. Trust was the glue. Most of the leaders whose companies SAP wanted to acquire were not ready to sell. As I spoke with them, I listened and moved with each company’s rhythms. And like a courteous dancer, I was careful not to step on any toes with SAP’s own intentions. I could be persuasive and persistent, but I also wanted leaders of any company we bought to come to their own decisions.
19 | Rituals create consistency amid chaos.
Throughout my career, as I observed successful people, I recognized that they shared a respect for the fundamentals of play, each practicing behaviors that were the foundation for their recurring successes. The actual behaviors were different for everyone. But like any ritual, they provided consistency, especially during chaos. These “repeatable methodologies,” as I called them, focused people. Improvisation was required, but instead of reacting emotionally, people acted wisely. Process trumped panic.
20 | Life’s value: heart, will, and honor, not wealth.
My dream was not about being rich, but about high achievement. It was about significance. For a young professional who grew up with very little money, the stuff money could buy was an easy way to measure progress. Ultimately, however, I knew that my life’s value would never be measured by things acquired, but by heart, by will, and by honor. That’s why I had my limits as to how far I was willing to go for a win.
21 | Better, bored, or broke, choose better.
The sentiment President Clinton expressed at the end of one of the board’s meetings. He said there were three things that we, as Americans, can choose to do with our lives: we can be better, we can be bored, or we can be broke. Welfare to Work, he stressed, was all about getting better. Better. What an uncluttered, modest word.
It gripped me. More and more, I was seeing my work not as a series of accomplishments but as a parade of moments led by a desire for my teams, my districts, my divisions—as well as myself—to be better. As much as I loved celebrating success, the joy of a goal achieved was usually short-lived. I was never done.
22 | Winning is the process, not the destination,
As a young salesman and executive at Xerox, winning was about being “the best,” which meant selling more than anyone else. All worthy goals, but in and of themselves, high scores and high sales did not encompass what it meant to win. Experience, exposure, and maturity—as well as a Greek poem—were revealing a truth that I’d probably always known: winning was not about a specific end but about how an end was met, moment after moment. Winning was the process, not the destination. A journey of striving to be better—to be kinder, more compassionate, hungrier, more humble, more audacious, more inspiring, more rigorous—that was what turned me on, what inspired me. The quest was the best.
Every quarter, I was reminded, and I reminded others, that winning was a process, not a destination. Victory, a state of mind. SAP always had to be looking for new ideas, adapting, winning, and, the next day, looking again.
23 | Leaders have to architect dreams into reality.
A leader’s role, however, is not just to dream but to architect dreams into reality. After all the envisioning and motivational talk, leaders have to plant their feet on the ground and get to work, executing with precision. If dreaming requires optimism, audacity, and empathy, bringing dreams to life is a more concrete endeavor, demanding hard work, discipline, teamwork, communication, and courage.
24 | Commit completely. Own your future.
“You must be proud of whatever organization you choose to work for,” I offer, “then pour yourself into it completely, and do not let anyone else but you shape your future.” She makes fantastic eye contact, and I return her resolute gaze. “I can tell from your determination that you will be what you aspire to be. I have no doubt.”
25 | Your dream is your superpower. Stay authentic.
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. Why? Because your winner’s dream is the essence of who you are. It is your power; it is your strength. Your winner’s dream represents your hunger, your inner magic, your capacity for empathy and for execution.
The purity of your winner’s dream is what emboldens you to triumph over thunderbolts and be a crusader on behalf of yourself and those around you. So imagine it, be ever loyal to it, and be forever inspired by it. Ultimately, your winner’s dream is your journey as you strive to be true to yourself and create a life of authenticity.
PS: We read this book as part of the research for our recent investment memo on ServiceNow (NYSE: NOW) to further deepen our understanding of Bill McDermott’s psyche, to understand his childhood, what drives him from the within, and why he has been able to repeat the successful sales from his newspaper delivery days, to the delicatessen, to Xerox, to SAP, and now to ServiceNow, and most importantly, if he can keep repeating it. We highly enjoyed and recommend this book.
The information contained in this article is for general informational purposes only. While every effort has been made to ensure the accuracy and reliability of the content, errors or omissions may occur. The author and publisher do not assume any responsibility or liability for any errors, inaccuracies, or omissions in the content, nor for any actions taken based on the information provided. Readers are encouraged to verify any information before relying on it and to seek professional advice as needed.
17 Sept 2025 | Eugene Ng | Vision Capital Fund | eugene.ng@visioncapitalfund.co
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