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

Release Date: March 18, 2025

In the second installment of the two-part series featuring Monte Wood, author of Generosity Wins and former CEO of Opus Agency, host Vince Chen delves deeper into the concept of generosity, exploring its true essence, misconceptions, societal challenges, and practical ways to cultivate a generosity-centered mindset. This episode provides listeners with profound insights and actionable strategies to integrate generosity into both personal and professional spheres, ultimately fostering greater success, happiness, and fulfillment.

Introduction to Monte Wood and Generosity

Vince Chen opens the episode by reintroducing Monte Wood, highlighting his extensive experience collaborating with industry leaders such as Steve Jobs, John Chambers, and Andy Jassy. The discussion is a continuation from the previous episode, where Monte shared his personal experiences and defined generosity as a habit essential for success.

Vince Chen (00:58):

"Monty has worked directly with legends like Mike Benief 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."

Defining What Generosity Isn't

Vince probes Monte to clarify misconceptions by asking him to define what generosity is not, aiming to help listeners avoid behaviors that undermine genuine generosity.

Vince Chen (05:48):

"Could you share some of those not so generous examples?"

Monte responds by contrasting Steve Jobs' singular focus on changing the world with his often harsh interpersonal demeanor. He emphasizes that true generosity is rooted in intent, not necessarily manifested through outward kindness.

Monte Wood (05:48):

"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... But his generosity, his manner was not."

He further distinguishes between genuine generosity and mere self-interest or myopic leadership, underscoring that understanding true generosity is key to embodying it effectively.

Societal Challenges to Practicing Generosity

The conversation shifts to societal factors that hinder the practice of generosity. Vince asks Monte why generosity has seemingly diminished in today's world.

Vince Chen (08:12):

"In your experience, why do you think we've lost the art of generosity?"

Monte attributes the decline primarily to greed and the influence of powerful entities that foster division and conflict for financial gain. He criticizes media outlets for prioritizing opinion over genuine reporting, which exacerbates societal divides and undermines generous interactions.

Monte Wood (09:12):

"I think that greed is a big part of it. And the reason I say greed is 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."

He remains optimistic, noting the emergence of influential individuals committed to consciousness and generosity, who strive to foster collaboration and mutual respect despite societal challenges.

Monte Wood (09:12):

"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."

Impact of Modern Technology and Media

Vince complements Monte's perspective by examining the role of technology and media in eroding genuine connections and, consequently, generosity.

Vince Chen (11:16):

"Social media has changed how we see and interact with the world. It affects how we conduct ourselves... Real connections are much deeper and more meaningful."

He highlights how superficial online interactions and the idolization of ruthless tech founders contribute to a culture where generosity is undervalued. The emphasis on connectivity over connection leads to a lack of meaningful relationships, making generous actions rarer and harder to sustain.

Optimism About the Future of Generosity

Despite the challenges, Monte remains hopeful about the potential resurgence of generosity in society. Vince acknowledges Monte's optimism and seeks confirmation.

Vince Chen (17:14):

"It seems to me that you are an optimist... Would you say that's accurate?"

Monte affirms his optimism, explaining that his positive outlook is a deliberate gift he shares with others to inspire hope and encourage more generous interactions.

Monte Wood (18:02):

"So the answer is yes... The optimism I share with people is a gift. It's a gift that maybe they walk away from me and are more hopeful and more positive in the next engagement that they have in life."

Cultivating a Generosity Mindset in Daily Life

Vince and Monte discuss practical strategies for integrating generosity into everyday routines. Monte emphasizes consistency and intentional practice as key to developing a generosity habit.

Vince Chen (19:05):

"What advice would you give on cultivating a generosity mindset in daily life?"

Monte shares his personal practice of maintaining a journal to document acts of generosity and appreciation daily, a habit he has sustained for over 600 days. He advocates for starting with a 30-day commitment to cultivate the habit, illustrating how repeated actions can lead to profound behavioral changes.

Monte Wood (19:45):

"I keep a journal, and in that journal I document some form of generosity and some form of appreciation every single day... If you practice it, you will get better at it."

Vince adds to Monte's advice by suggesting the use of handwritten journals over digital logging to enhance mental well-being and foster deeper connections.

Vince Chen (21:39):

"Studies show that the act of writing by hand helps with analyzing, filtering and clarifying thoughts, which can really benefit mental health."

Monte agrees, noting the importance of being generous with oneself and maintaining personal well-being to effectively practice generosity towards others.

Monte Wood (22:17):

"Documenting your generosity and what you appreciate in life... you become much better at being generous."

Personal Anecdotes Highlighting Generosity

Monte shares a memorable encounter with Elon Musk and Grimes, demonstrating how unexpected acts of generosity can leave lasting positive impressions. This story underscores that generosity often transcends financial means and is deeply rooted in genuine human connection.

Monte Wood (15:43):

"Elon Musk and Grimes and X... He really stopped and cared about the conversation he was having with us... That gives me hope."

Concluding Insights and Call to Action

As the episode draws to a close, Vince reflects on the enduring impact of generosity in his own career, emphasizing the value of meaningful, supportive relationships. Monte reciprocates the sentiment, expressing his appreciation for Vince's generous spirit.

Vince Chen (25:57):

"Those relationships are rare and precious and they've made all the difference in my journey."

Vince encourages listeners to adopt the practices discussed, highlighting the transformative power of generosity in building connections and achieving personal and professional success.

Vince Chen (26:18):

"If you like what you heard, don't forget, subscribe to our show. Leave us top rated reviews, check out our website and follow me on social media."

Key Takeaways

1. Understanding Generosity: True generosity is rooted in intent and purpose, not merely in outward kindness or financial giving. It's about empowering others and fostering positive change.

2. Identifying Non-Generosity: Behaviors such as selfishness, division, and conflict are antithetical to generosity. Recognizing these can help individuals avoid unintentional negative actions.

3. Societal Barriers: Greed, divisive media, and the superficiality of modern digital interactions hinder the practice of genuine generosity.

4. Cultivating Generosity: Consistent practices such as journaling acts of generosity and appreciation can help embed generosity into daily life. Handwriting, in particular, can enhance the depth of this practice.

5. Optimistic Outlook: Despite societal challenges, there are influential figures and emerging movements focused on generosity and conscious collaboration, offering hope for a more generous future.

6. Practical Application: Generosity can be integrated into various aspects of life, from simple acts like sharing a smile to more intentional actions like mentoring others, leading to immediate and tangible benefits.

Notable Quotes

• Vince Chen (00:58):
  "Monty has worked directly with legends like Mike Benief of Salesforce, Andy Gross of Intel, Steve Jobs, John Chambers of Cisco, and Andy Jassy of Amazon."

• Monte Wood (05:48):
  "His generosity, his focus of generosity was to change the world and make it a better place."

• Monte Wood (09:12):
  "I think that greed is a big part of it... media outlets... creating conflict amongst parties to line their own pockets with money."

• Vince Chen (11:16):
  "Real connections are much deeper and more meaningful."

• Monte Wood (18:02):
  "The optimism I share with people is a gift. It's a gift that maybe they walk away from me and are more hopeful and more positive in the next engagement that they have in life."

• Monte Wood (19:45):
  "If you practice it, you will get better at it."

• Monte Wood (15:43):
  "That gives me hope that there are people, powerful people out there that will help us make a difference."

Conclusion

Episode #242 of Chief Change Officer offers a compelling exploration of generosity, distinguishing it from mere kindness and highlighting its transformative power in both personal and professional realms. Monte Wood's insights, combined with Vince Chen's thoughtful inquiries, provide listeners with a nuanced understanding of how to cultivate and embody generosity amidst contemporary societal challenges. By adopting the practical strategies discussed, individuals can foster meaningful connections, enhance their well-being, and achieve greater success and fulfillment.

For those inspired to embrace generosity as a foundational aspect of their lives, subscribing to the Chief Change Officer podcast on LinkedIn, Apple, Spotify, and YouTube is a step towards continued personal and professional transformation.