Chief Change Officer
#241 Monte Wood on Generosity: The Most Underrated Career Cheat Code — Part One
Tue, 18 Mar 2025
Monte Wood, former CEO of Opus Agency and author of Generosity Wins, knows that generosity isn’t just about being nice—it’s a game-changer in business and life. From working with icons like Steve Jobs and Mark Benioff to lessons from his mom, Monte has seen firsthand how small acts of giving create big returns. In this episode, he breaks down why generosity is the real secret to happiness and career success—and why it’s more powerful than you think.Key Highlights of Our Interview:True Generosity in Leadership: More Than Just Charity“Being generous isn’t just about grand acts of philanthropy. It’s about caring for the individual. Whether it’s helping employees grow beyond their roles or driving an old Toyota to work, leaders like Andy Grove and Mark Benioff show that humility and connection are what truly drive success.”Why Generosity is the Key to Confidence, Courage, and Success“Generosity isn’t just about giving—it’s a strategic move toward success. Helping others builds faster, more meaningful relationships, while also boosting your own confidence and courage. Harvard’s 50-year study shows that close connections are the top predictor of happiness, and generosity is the engine that powers those relationships.”Tracking the Untrackable: The True ROI of Generosity“Generosity doesn’t fit into the typical business models of ROI—no one’s handing you a direct return. Yet, the rewards are undeniable. Life has a way of paying you back tenfold, proving that being generous might be the most strategic investment you can make, even if it can’t be measured in dollars.”Generosity Isn’t Always Grand – Sometimes It’s Just a Smile“Even the smallest act of generosity can be life-changing. A smile, a kind word, or even cleaning up a public restroom can shift someone’s day. In a world full of loneliness and depression, simple acts of generosity may be the most powerful way to create joy and connection.”_____________________Connect with us:Host: Vince Chan | Guests: Monte Wood______________________--Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs,Transformation Gurus & Bold Hearts.10 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.130,000+ subscribers are outgrowing. Act Today. --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Monte Wood and why is generosity important to him?
Monty has worked directly with legends like Mark Benioff of Salesforce, Andy Gross of Intel, Steve Jobs, John Chambers of Cisco, and Andy Jassy of Amazon. From these leaders, his own mentors, and his mother, Monty has learned what generosity truly means, why it matters, and how to apply it to life and career to become more successful, happier, and healthier. Curious to find out more?
We made a two-part series for you. In today's episode, We'll dive into Monty's personal experiences, his definition of generosity, and why he believes so strongly in practicing generosity as a habit. Tomorrow, we'll explore what isn't generous, why practicing generosity can be difficult in today's world, and how to nurture a generosity-centered mindset.
If you are still skeptical about how generosity can lead to success, join us for this conversation. We'd love for you to be part of the discussion. Let's get started.
In my very early days, probably at the age of 16, I had a young mentor. And that mentor actually gave me a formula about being successful. And part of it was just believing that I could be successful. And then part of it was living a good life, being a generous person. And I believed him. So at a very early age, I had very high aspirations.
Chapter 2: What are Monte Wood's early influences on generosity?
I grew up in a small town called Milton-Freewater in Oregon. only about 3,500 people in the town. And yet I believed at that point, I would someday run a company that was over a hundred million in revenue with hundreds of employees. And I believed it right from the very beginning. To augment that, interestingly enough, my mom He's one of the most generous people that you will ever meet.
The combination of my kinkle, my mentor, and my mom as my mentor in generosity led me to this simple formula that I would become successful by making other people successful. It's pretty simple, but I will tell you why. is magic and it worked. I had tremendous success and my goal is really to pass it on and help others do the same because not only was it very good formula, it was a lot of fun.
Yes, I agree with you. In fact, when it comes to leadership, I always describe myself in two ways. First is about walking the walk and talking the talk. Second, I believe in servant leadership. I've been lucky in my corporate career to have worked for bosses who embraced this kind of leadership. They helped me grow, become a better leader, and they made me shine.
But in my mind, I don't necessarily call this generosity. I still think of it as an exchange of value. As a subordinate, I help achieve business goals, and in return, they support me, hire me, and take pride in recognizing my talents. When I perform well, it makes them look good too. It's not just kindness, it's mutually beneficial and drives business results.
So I guess what I'm saying is, I see it as a leadership style, but not necessarily generosity. Now, I'd love to hear your thoughts. What does generosity mean in the context of leadership, especially in the lessons you've learned from your mentor?
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Chapter 3: How is generosity defined in leadership according to Monte?
It's a great question because there is a lot of exchange, as Adam Grant talks about in leadership, where I do something for you and I expect you to do something for me. But great leaders, great servant leaders, care about the person, not just the work being done. They care about the person's family. They care about the person's life. They help them grow, in many cases,
I helped employees grow out of our company because the best path for them was to go do something else. They outgrew the jobs they were in and the potential they had within the company. And I took great pride when they left and did something else. I'll give you a simple example. I have a very good friend who owns many franchise stores, Taco Bell franchise stores. He cares about his employees.
He actually hired somebody to come in and train his employees how to change their tires, how to balance their checkbooks. It has nothing to do with how to make a taco or how to service their customer. It's about caring for the person. And when you care for somebody, you create a connection. And that connection is really important in everyday life, but even more so in business.
I'll give you a much grander example. Mark Benioff of Salesforce, the founder, CEO of Salesforce, started the company with the idea of giving a certain percentage of profit to charities. He supported many different organizations. But I will tell you, The most generous thing I ever saw was he could walk through a crowd of his employees and he always remembered their names. He showed them respect.
He let them know that he cared for them as people. We would have an event with 2,000 people and I swear somehow he knew all of their names. I'm sure he studied before he ever got there. But he truly cared about the individual, not just the job they did. And because of that, they worked very hard for him. They created tremendous success.
Andy Grove at Intel is another individual that I worked with, and I loved this man was so humble. You've heard stories probably of the great leadership and he literally reinvented the semiconductor industry and rejuvenated Intel, but he worked out of a cubicle. He drove an old Toyota truck and he didn't consider himself any better than anybody else in the company.
And he treated everybody as important. as the next person, whether they were a vice president or whether they were somebody in the fab making chips. And that is, that's not just doing generous acts. That's being a generous person. And I think they're two different things.
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Chapter 4: What distinguishes real connection from mere connectivity?
As you were sharing, you brought back some memories of mine from my corporate days. 15, 20 years ago, maybe? A lot has changed since then. We had the credit crisis, then the rise of social media with the iPhone and everything that came with it. Then came COVID and now AI. But it's not just about the technology. It's also about mindset shifts and generational gap.
By that, I don't just mean the typical you're older, I'm younger kind of gap. It's more than that. Millennials, Gen Z, for example, they've become more vocal. Some of them may be too vocal. Then we got the even younger generation coming in. On the other hand, you've got Gen X, baby boomers. There's so much going on in the world that it feels like we've become less connected in a lot of ways.
Technology allows us to connect like how you and I are talking right now. We wouldn't have met if this tech wasn't democratized like it is today. I mean, even a phone call like this used to be very expensive. So yes, we are now connected. But I call this connectivity more than true connection. Because real connection takes time, patience, and effort.
For example, I always insist on a pre-call with my podcast guests. I want to get to know them and I want them to know me so that when we record, our conversation is more natural. I dedicated that time 30 or even 45 minutes. because I genuinely care about making a good show. Now in that case, is that generosity?
I'm not expecting anything in return, but at the same time, I know it helps me achieve a certain result. So would you say that is true generosity? Or is it more of a behavior with a specific goal in mind?
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Chapter 5: How does Monte Wood define true generosity?
Let me define generosity. If you go online and search for definitions, they are all over the board. And most of the definitions of generosity focus on giving money, so philanthropy. But generosity is much bigger. So in the book, we actually defined generosity as any act of giving or kindness when done with no expectation of exchange or return from the recipient.
If you are doing this with no expectation of exchange or return from me... or from your audience, then that is a pure generosity. That is where the purest power of generosity comes. My guess is you're not doing your podcast because you wanna be famous or you wanna make a lot of money. My guess is you're actually truly desire to help people and make a difference in the world. And I appreciate that.
And that's a driving force for many successful people, right? There's a scientific study that says that humans are the only species that You are generous with those that they will never associate with or never meet. In other words, they're generous beyond their family, beyond their community, beyond those that they will ever know. That's a human trait.
And that trait is actually credited with the helping of creating societies and even a global community of such.
Of course, you want to make an impact. From that angle, I guess you could say it's a form of generosity because I don't really expect anything in return from the listeners. But I do care about that whatever I say or you say or any guest on the show says has some kind of impact. Even if it's just a minute, a one-minute impact for someone who listens, that would already make me really happy.
Yes, and I agree. So my book probably will not sell 100,000 copies. But I will tell you, Vince, that I've had 25 or 30 people tell me the book changed their lives for the better. I had one person just last week came up and said that she changed jobs because she realized in reading the book that
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Chapter 6: Can generosity be considered selfish if it leads to success?
that the people she worked for were not generous people and that she did not want to be in that situation. And she moved to another job and she said it's the best thing that has happened to her in many years. So that kind of thing is just such a beautiful reward. In fact, it spurs me to ask you a question. Is it selfish? to be authentically generous.
So again, with no expectation of exchange or return from the recipient in order to create your own success.
The first thing that comes to my mind is if I'm being generous and generosity helps me succeed, doesn't that make it selfish? Does generosity leading to success mean there's some hidden self-interest? Is that why you're asking? Yes. If you ask me, selfish usually carries a negative connotation. When we call someone selfish, it's typically not a good thing.
So when you mentioned that genuine generosity helps you become more successful, is that selfish? I would say no. I wouldn't use the word selfish. I would call it self-awareness. If I believe in the principle that generosity wins, it becomes part of my attitude and behavior. I'm following my own path based on principles I truly believe in.
From the outside, people might think I'm focused on what I want, but it's more about knowing who I am and what I stand for. Maybe some could call that selfish, but I would just call it being clear and committed to my values.
Yeah, I think your initial response, no, is a good answer. I actually believe that focusing on generosity, helping others, right, to pave the way for your own success isn't being selfish. It's just being wise. And this is a hard concept for people to understand, right? But truly generous people.
If you read up, if you pick up any book on success, there's a number of things they'll tell you that are going to lead to success. At the top of the list is always relationships. Close in relationships. Harvard just published their study, their 50-year study. And the most important aspect of happiness is for individuals out of their study was relationships, connected, close relationships.
Now the self-help books are going to tell you confidence. Then they're going to say mindset. And then they're going to say trust. And then they're going to say your own emotional well-being. And I believe that being a generous person leads to all of those. So being a generous person leads to success. If you know that, then you have a North Star. You have something that you can focus on every day.
You can attract success versus desperately pursuing it. And I think attracting it by being a generous person is a much more rewarding way of going through life. So let's break that down a little bit. Relationships. Everybody knows that generous people develop relationships faster and more meaningful. Courage. Let's talk about confidence and courage.
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