Chief Change Officer - #242 Monte Wood on Generosity: The Most Underrated Career Cheat Code — Part Two

Episode Date: March 18, 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:Generosity Beyond Kindness: Lessons from Steve Jobs, John Chambers, and Andy Jassy“Steve Jobs’ goal to democratize technology was generous, even if his approach wasn’t. Leaders like Chambers and Jassy showed that while generosity doesn’t always come with kindness, the drive to uplift others’ success is, in itself, a powerful form of generosity.”The 600-Day Challenge: How Practicing Generosity Daily Transforms You“Documenting a daily act of kindness, whether it’s a smile or genuine listening, became a habit that revealed a thousand ways to be generous—proof that practicing generosity opens new perspectives.”Unexpected Generosity in a Hot Tub: A Chat with Elon Musk“In an unexpected encounter, Musk showed genuine interest and warmth, sharing laughs and stories. It was a small gesture, but a powerful reminder of the impact of unexpected generosity from those at the top.”The Hidden Costs of Greed and Division in Today’s Media“With opinion-driven media stirring division, the challenge lies in overcoming these forces with conscious generosity and mutual respect—proving that true strength is found not in agreement, but in the ability to disagree respectfully.”_____________________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.

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul is a modernist community for change progressives in organizational and human transformation from around the world. How many people do you know who actually walk into a public restroom and leave it cleaner than they found it? I do. And so does the wife of our guest. Like me, she does it because she wants to leave it better for the next person. So who is our guest today?

Is Monty Wood, author of the book called Generosity Wins, and the former CEO of Opus Agency, a creative branding partner for some of the world's most influential brands. like Mike Benioff of Salesforce, Andy Gross of Intel, Steve Jobs, John Chambers of Cisco, and Andy Jesse 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 will 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 trump you as really rude as 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, 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.

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 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 tapas 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 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 gonna 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 and then I can respectfully disagree and we can be fine together. But it is now, it's almost if a lot of media is promoting that if you don't agree then you should hate the person that you disagree with. And that is incredibly dangerous in my opinion. What do you think? Looking at it from human nature, Greed is one of our seven deadly scenes, as they say.

We even got a movie called Seventhth 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 another layer, often with their own agenda, pushing certain narratives that can cloud our judgment, especially around elections or other high-stakes events.

Independent journalism is waiting, 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 he 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 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, 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. Yep. I would agree. And you'd be surprised the people that are generous that you might not expect. Two and a half years ago in a hot tub at a hotel in the island of Lanai, and Elon Musk and Grimes and X

walked up to the hot tub. We sat there and chatted for probably 45 minutes. We weren't anybody in comparison to him. He was considerate and gave us conversation and we laughed and he talked about a German movie that he had watched and was all animated. He could have just turned and walked away, but he didn't. He was considerate and I considered it to be a very generous thing that he did. He left a very positive impression on me, like he really cared about people.

I'm sure when you're that wealthy, there's all kinds of limitations. And I know there were security guards in every direction, all in black that we couldn't see, But he really stopped and cared about the conversation he was having with us. And that gives me hope. It really does give me hope that there are people, powerful people out there that will help us make a difference. It seems to me that you are an optimist.

You are hopeful about the impact of generosity in the world, despite the challenges we've discussed. You genuinely and passionately want to help people become more generous. You share insights, you write, you publish books to get the message out there. Would you say that's accurate? That you believe we can still build a more generous society? One where leaders and individuals alike

can grow to be more generous, happier, and ultimately more successful? So the answer is yes. But I have to be careful, right? If you're optimistic, we'll turn people off. So if I am frequently optimistic with the person that I'm talking with, if I'm understanding their energy, their way, how they communicate, the tone of their voice, their comfort with eye contact, if I'm aware of those things, then the optimism I give them in a way that they can absorb it is a gift.

I go through life thinking the optimism I share with people is a gift. It's a gift that maybe they walk away from me and are male hateful and more positive in the next engagement that they have in life and it turns out amazing for them. For everyday people, not just leaders or influencers, advice would you give on cultivating a generosity mindset in daily life? How can we become more conscious of generosity and move beyond the mindset to make it a habit? So it shows up consistently in our actions and behaviors. Any practical tips for building this habit? Yeah, in order not to be a hypocrite, I'm going to give an example because I think that I have to practice what I preach. I keep a journal, and in that journal I document some form of generosity and some form of appreciation

every single day. And I haven't always done this, but I think I'm very close to 600 days now of doing this. And our recommendation in the book is just to do it for 30 days, to document, to actually be generous every day for 30 days. So I set out to do that. And I liked it so much that I'm now on day 672 or whatever. It's just like anything else in life. If you practice it, you will get better at it.

You'll find a thousand ways that you can be generous. It may be sharing optimism, it may be sharing a smile, it may be just really intently listening to somebody, it may be calling, using somebody's name and remembering their name and making them feel special. There's so many ways to be generous. And the more you do it, the easier it becomes and the more you realize all the different ways. And of course, we list all of those ways in the book. And in the book, there's 12. I talk about famous leaders that I've worked with

and so forth. In the book there are 12 incredibly successful people that we interviewed and asked them how generosity has played into their success and how they've been generous in their lives. It's great to not only practice it yourself, but to understand how other people have done it. Yes, I actually add to that. I think it's really beneficial to use a notebook and pen instead of typing on your phone. Studies show that the act of writing by hand helps with analyzing, filtering, and clarifying thoughts, which can really benefit mental health.

So I assume you're suggesting actual writing, not just typing on a laptop or phone? Yeah, I do both. actual writing, not just typing on a laptop or phone? Yeah, I do both. Sometimes when I'm traveling, it's easier to do on the phone. But the hardest thing in life is doing anything consistently. So I have done it consistently for 600 days, every day.

I have done it consistently for 600 days, every day. And there are a few other things that I do consistently every single day, but I'm not going to go into those now. Because I also, I think you need to be generous with yourself. So there are some things I do exercise-wise every single day for the last 600 days. And that's my way of being generous with myself. Documenting your generosity and what you appreciate in life. When you appreciate more, when you understand, when you become good at appreciation, you become much better at being generous. become good at appreciation, you become much better at being generous. Yes, and about using the phone, I actually go a step further, jogging things down on

my phone, but eventually I transfer it into a physical notebook. I know there's tech now that lets you write digitally, and it saves to a notebook file. But I still enjoy the actual human art of handwriting. Writing really makes a difference. It helps me feel better, connected, which is important for mental wellness, especially in a world that can feel isolating. Even if we're not meeting face-to-face, just connecting and talking is rewarding. For instance, podcasting has had a huge positive impact on my own mental wellness.

It feels good to connect like this, even if it's virtual. So when it comes to practicing generosity, it doesn't have to be complicated. Unlike business, where we calculate ROI and financial budgets, the benefits of generosity just reaching out, connecting, can be immediate and tangible. I think maybe I've created an evangelist of generosity over there. Thank you, thank you. Well, in fact, I'll send you my resume because if you are ever building a generosity empire, I would love to join your journey. Listening to you has brought back memories from my early career.

I worked with senior leaders who were generous in their own way, nurturing and helping me without expecting anything in return. That generosity built meaningful connections beyond work. Even after we all moved on, we stay in touch. Those relationships are rare and precious, and they've made all the difference in my journey. It's been a pleasure chatting with you. I think you have a generous spirit and I appreciate that. If there's anything I can do to help or anything you want to do in the future, you just let

me know. Thank you so much for joining us today. If you like what you heard, don't forget to subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care.