Chief Change Officer
#372 Building a Life (and Career) on Everyday Generosity — Part Two
Fri, 16 May 2025
What does generosity look like in a divided, distracted world?In Part Two, Monte Wood—former CEO of Opus Agency and author of Generosity Wins—dives deeper into how generosity gets lost in the noise of modern life and what it takes to reclaim it. From quiet reflections on Steve Jobs’ legacy to a chance encounter with Elon Musk in a hotel hot tub, Monte shares how generosity can take many forms—and why practicing it daily is the ultimate leadership move.He also unpacks the forces working against generosity: media polarization, digital disconnection, and our culture of performative success. But with optimism, awareness, and a bit of handwritten gratitude, Monte believes we can rewire how we relate to ourselves—and each other.Key Highlights of Our Interview:What Generosity Isn’t: Learning from the Hard Edges“Steve Jobs wasn’t always kind—but his mission was generous. He wanted everyone to access technology. That matters.”The Hidden Generosity of Power Players“Elon Musk sat in a hot tub and talked German cinema with strangers. That moment of presence? Pure generosity.”Why Greed and Media Noise Make Generosity Harder“Our media doesn’t report anymore—it polarizes. It’s designed to divide us, not connect us. That’s why generosity is revolutionary.”Connectivity ≠ Connection“Texting someone in the same room isn’t connection. Real generosity requires presence—not just Wi-Fi.”A 600-Day Habit That Changed His Life“For nearly two years, Monte has written down one act of generosity and one moment of appreciation. Every. Single. Day.”How to Start Your Own Generosity Practice“It doesn’t have to be dramatic. A smile. A name remembered. A moment of full attention. That’s the starting line.”The ROI of Generosity Isn’t in Metrics—It’s in Meaning“You won’t find it in a spreadsheet. But the return? Real connection. Better leadership. More joy.”Be Generous With Yourself, Too“Monte exercises daily. Not for performance—for self-gift. Being generous starts with how you treat your own body and mind.”Hope Isn’t Naive—It’s a Form of Generosity“Monte calls himself ‘appropriately optimistic.’ His optimism is calibrated—not blind. It’s a gift he gives carefully to others.”Why He Still Believes in a More Generous World“We can’t control the noise—but we can choose how we show up. And small, consistent acts of generosity still move the world.”_____________________Connect with us:Host: Vince Chan | Guests: Monte Wood --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<
Chapter 1: What does generosity mean in today's world?
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. I have a couple of follow-up questions. You shared why generosity is important, your definition, what it means, and some real examples from people you've worked with.
But on the flip side, I'd like to hear about what isn't generosity. In your career, you've worked with a lot of leaders and teams. What are some behaviors or attitudes you've seen so far that you would say are the complete opposite of generosity Maybe things that shrug you as really rude. I think understanding the flip side would be helpful for listeners.
giving them a clearer perspective on what generosity isn't. It might even help them recognize, identify, and avoid those less generous behaviors in their own actions or interactions. Could you share some of those not so generous examples?
I'll give an example that many people have quoted. One of the most successful people in history, actually. I worked directly with Steve Jobs when he was at Next and indirectly at Apple for many years. There are many quotes that circulate on the internet now of his last and final words with his best friends.
Chapter 2: What isn't generosity? Learning from Steve Jobs
And all of them say that he talked about he wished that he had been more generous in his life. He wished he had benefited those around him. Now, I think there's a little bit of a misnomer there because he was not a kind person. I sat in rooms and watched him berate people. other people and do it in a very inconsiderate and unkind way.
But his generosity, his focus of generosity was to change the world and make it a better place. He wanted to empower everybody of all abilities to be able to use technology for themselves. And his compass was generous. His manner was not. And in the end, I think he wished that his manner had been different. So I think that's probably the best example that I can give.
Most of the great leaders that I worked with, John Chambers and Andy Jassy and many others, actually were generous people. They worked harder than those people around them to create success for others. Some of them were very myopic and maybe didn't have the best interpersonal skills, but I don't know that they were I wouldn't say they were not generous.
I think that maybe they just didn't understand generosity, which again is one of my goals is to help people understand what generosity is, how simple, very simple, easy things when done with the right intent can make a tremendous impact in the world.
If you could stand on top of a mountain and shout to the world, telling everyone how essential it is, not just as a concept, but as a life approach that can truly change your life, make you happier, and bring more fulfillment, then why aren't more people embracing it? In your experience, why do you think we've lost the art of generosity? I have my own theory, but I'd love to hear yours.
What's gone wrong in a society that some of us have either forgotten about it or never developed the skill at all?
I think that greed is a big part of it. And the reason I say greed is because there are powerful entities and people who are using divide, who are using conflict and creating conflict amongst parties to line their own pockets with money. When you have a media, all of our media outlets, there's not a single good one out there, right? They're not reporting news anymore. It's all opinion.
And it's all opinion to create divide and conflict. When you have such powerful entities that are trying to do that, it's difficult for the single person standing on a mountaintop to get people to understand. Now, I will say there are some really strong and powerful people that are focused on consciousness and generosity now. And we're beginning to see some of that effect.
And I'm not going to give you any names, but I'm fortunate to be on the inside of some of that. And I am hoping that those people can create, like you and I talked about earlier, collaboration. respect for each other. I don't have to agree with everything you say. In fact, I never will agree with everything you say, but I can respect your opinion and I can respect you as an individual.
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Chapter 3: How do media and greed affect our perception of generosity?
Looking at it from human nature. Greed is one of our seven deadly sins, as they say. We even got a movie called Seventh. Brad Pitt, wasn't it? While there's a lot that could be said about that, I would rather focus on how our present reality has impacted generosity. First off, Social media has changed how we see and interact with the world.
It affects how we conduct ourselves, often emphasizing superficial connections over genuine connections. Mainstream media adds an outer layer, often with their own agenda. pushing certain narratives that can cloud our judgment, especially around elections or other high-stick events. Independent journalism is wailing, and we're left with these biased perspectives shaping the way we think.
Then there's this trend of idolizing successful tech founders, especially among younger leaders. They see people raising millions, building billion-dollar companies, and assume they need to emulate every behavior to reach that level. But as you pointed out, even Steve Jobs though he had a clear purpose, wasn't known for his kindness in the workplace.
It's as if some tech founders believe they have to be ruthless to be successful, ignoring that generosity and empathy are just as essential to leadership and success. And this brings us to a big misconception with technology. Connectivity does not equal connection. We think that having friends or followers means we are connected, in quotation. But that's not true.
Real connections are much deeper and more meaningful. People text family members in the same house rather than having a face-to-face conversation. In offices too, I hear stories from friends who say, back in the day, we just turned to the person next to us to chat. Now, even when two people are seated beside each other, one would send a message instead of speaking.
All this technology has left us disconnected as human beings. And without real connection, the idea of giving generously without expecting anything in return becomes wearer. This disconnect is a big factor across all cultures and why generosity is harder to come by today.
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Chapter 4: Why does connectivity not equal connection?
Chapter 5: What are simple acts of generosity we can practice daily?
giving them a clearer perspective on what generosity isn't. It might even help them recognize, identify, and avoid those less generous behaviors in their own actions or interactions. Could you share some of those not so generous examples?
I'll give an example that many people have quoted. One of the most successful people in history, actually. I worked directly with Steve Jobs when he was at Next and indirectly at Apple for many years. There are many quotes that circulate on the internet now of his last and final words with his best friends.
And all of them say that he talked about he wished that he had been more generous in his life. He wished he had benefited those around him. Now, I think there's a little bit of a misnomer there because he was not a kind person. I sat in rooms and watched him berate people. other people and do it in a very inconsiderate and unkind way.
But his generosity, his focus of generosity was to change the world and make it a better place. He wanted to empower everybody of all abilities to be able to use technology for themselves. And his compass was generous. His manner was not. And in the end, I think he wished that his manner had been different. So I think that's probably the best example that I can give.
Most of the great leaders that I worked with, John Chambers and Andy Jassy and many others, actually were generous people. They worked harder than those people around them to create success for others. Some of them were very myopic and maybe didn't have the best interpersonal skills, but I don't know that they were I wouldn't say they were not generous.
I think that maybe they just didn't understand generosity, which again is one of my goals is to help people understand what generosity is, how simple, very simple, easy things when done with the right intent can make a tremendous impact in the world.
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Chapter 6: How can generosity influence leadership and success?
Chapter 7: What is the role of optimism in practicing generosity?
Chapter 8: How can we nurture a generosity-centered mindset?
Monty has worked directly with legends like Mike 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. Yesterday, in Part 1, our last episode, we looked into Monty's personal experiences, his definition of generosity, and why he believes so strongly in practicing generosity as a habit. Today, Part 2, we'll explore what isn't generosity. why practicing generosity can be challenging in today's world, and how to nurture 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. I have a couple of follow-up questions. You shared why generosity is important, your definition, what it means, and some real examples from people you've worked with.
But on the flip side, I'd like to hear about what isn't generosity. In your career, you've worked with a lot of leaders and teams. What are some behaviors or attitudes you've seen so far that you would say are the complete opposite of generosity Maybe things that shrug you as really rude. I think understanding the flip side would be helpful for listeners.
giving them a clearer perspective on what generosity isn't. It might even help them recognize, identify, and avoid those less generous behaviors in their own actions or interactions. Could you share some of those not so generous examples?
I'll give an example that many people have quoted. One of the most successful people in history, actually. I worked directly with Steve Jobs when he was at Next and indirectly at Apple for many years. There are many quotes that circulate on the internet now of his last and final words with his best friends.
And all of them say that he talked about he wished that he had been more generous in his life. He wished he had benefited those around him. Now, I think there's a little bit of a misnomer there because he was not a kind person. I sat in rooms and watched him berate people. other people and do it in a very inconsiderate and unkind way.
But his generosity, his focus of generosity was to change the world and make it a better place. He wanted to empower everybody of all abilities to be able to use technology for themselves. And his compass was generous. His manner was not. And in the end, I think he wished that his manner had been different. So I think that's probably the best example that I can give.
Most of the great leaders that I worked with, John Chambers and Andy Jassy and many others, actually were generous people. They worked harder than those people around them to create success for others. Some of them were very myopic and maybe didn't have the best interpersonal skills, but I don't know that they were I wouldn't say they were not generous.
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