Going Big! with Kevin Gentry
Episode: One Year of Going Big!: The Best of Going Big
Date: September 22, 2025
Episode Overview
This special one-year anniversary episode of "Going Big! with Kevin Gentry" celebrates the milestones and impact of the podcast's journey so far. Kevin revisits the most memorable insights and moments from the past year, assembling them into three core themes:
1. Risk-taking and Entrepreneurship
2. The Power of Mentorship
3. Bold Leadership
Through curated guest highlights, listener lessons, and Kevin’s own reflections, this episode distills practical wisdom from prominent entrepreneurs, political leaders, nonprofit trailblazers, and innovators who have embraced big visions, overcome obstacles, and inspired change.
Major Themes and Key Insights
1. Risk-taking and Entrepreneurship
Key Takeaway: Courage, resilience, and a constructive attitude towards failure are foundational to going big in entrepreneurship.
Notable Segments and Quotes:
-
Kevin Gentry introduces the theme (02:22):
"What did today for your benefit was to see if there were some insights and lessons from the first year that could be compiled and clipped in a way that could even help us focus more narrowly into some key insights ... The first one ... is in the area of risk taking and entrepreneurship."
-
Newt Gingrich on relentless research and risk (04:20):
"You've got to learn everything. You've got to be a total pervert in your area and, and know every single thing in that specific niche."
"You have to be willing to go big, and you have to be willing to put everything out there and try as hard as you can."
(04:30 - 04:48) -
On seeking guidance:
"After you've done all the research... Bring your questions and be prepared. You will be shocked how many successful entrepreneurs in that field are willing to talk to you ... there will be people and they will sit with you ... and it will really go a long way and make you feel ... that you've got that wind at your back to help you."
(05:01 - 05:20, Newt Gingrich) -
On resilience:
"You can't give up because all you're gonna do is be told no a thousand times..."
(05:31, Newt Gingrich) -
Jeff Rosenthal (Summit Series), on imposter syndrome & risk (06:55):
"Our reaction to imposter syndrome was to mess with people. Instead of being like, oh man, I don't know if I can be in this room... Our emotion when we would feel that was to just literally mess with those people ... At a minimum, this is going to be their favorite interaction of the week... If you knew you couldn't fail. We didn't think about failure at all. We didn't have anything. Why would we care?"
(06:55 - 08:27, Jeff Rosenthal) -
On productive attitudes toward failure:
"There's a way to perceive failure that's more productive, which is just, it's all a learning opportunity. It's all on the path to getting where you want to go. If you are doing something new, you're definitely wrong. The question is just how far are you from the right answer?"
(09:15, Jeff Rosenthal)
Memorable Story:
-
Todd’s Personal Journey (19:03 – 30:43):
From high school dropout and parent at age 20 to a Harvard doctorate and acclaimed scholar, Todd’s story illustrates that "fit" and finding the right environment unlocks human potential:"Up until that point, I had tried to do things the exact same way as every best practices ... and it didn't work. And so I started making decisions based on what little I knew about myself ... And it was small things at first ... That would start to create a change in me." (20:22+)
"There are really two things ... that have really informed everything that I've done since professionally ... fit really matters ... The second thing is the unbelievable importance of relationships and, you know, like Marilyn Diamond." (30:45)
2. The Power of Mentorship
Key Takeaway: Mentors are vital at all stages—both finding mentors and being one to others can catalyze personal and professional growth.
Notable Segments and Quotes:
-
Doug DeVos’s father’s wisdom (36:00):
"You're never too young to be a mentor and you're never too old to have a mentor."
(36:00, Doug DeVos quoting his father) -
On the flexibility of mentorship:
"A mentor is someone that you intentionally choose to actively learn from. I have people that I consider to be my mentors who have never even met me ... Not every mentor relationship needs to be a lifelong commitment. As we change, we need new people to learn from..."
(37:23 - 38:28, Doug DeVos) -
On reciprocal mentoring:
"There are always plenty of people that can learn from you. And one of the best ways to learn is to teach. So I think putting yourself in the role of mentoring others is as important as ... being mentored by others."
(38:32, Doug DeVos) -
On unlikely mentors:
"I was a smart aleck in junior high school ... and he said stay after school ... He took me to a concert in Cleveland at the Severance hall. And at the intermission, he said, you should go to college. That's when I decided to go to college. Wow."
(48:46 - 49:52, Newt Gingrich story) -
Todd on Marilyn Diamond (33:45):
"When we think about what it means to believe in someone, you often think that it requires such a heavy lift ... But we can all be the Marilyn Diamonds in other people's stories. You think about it, her effort changed my life. And it was so inconsequential to her that she didn't even remember doing it. That's the asymmetry about what it means to believe in people." (33:45, Todd)
Memorable Moments/Advice:
-
John Pope’s legacy (40:30):
"Very important. Of course, I'm very fortunate that my biggest mentor was my father, John Pope ... But my dad always encouraged me to do what I wanted to do ..."
(40:30, Doug DeVos) -
On paying mentorship forward:
"Not only can you give back, but can you pay back or pay forward by helping mentor young people?... So you never know how young you are when you find a mentor."
(41:47, Doug DeVos) -
Rush Limbaugh as a mentor (42:32):
"He (Rush Limbaugh) was a real mentor. I could email him, text him day and night and get a response on how do I do this, what should I do? ... His job was to entertain. And if I could keep people company... then I could persuade, then I could promote, then I could change the country."
(42:32, Eric recounting Rush Limbaugh)
3. Bold Leadership
Key Takeaway: Going big as a leader requires vision, humility, listening, and inspiring collective pursuit.
Notable Segments and Quotes:
-
Doug DeVos on believing in people (54:05):
"You always have to look at the individual and say, somewhere in there is incredible potential, and I don't know what it's going to be to unlock it."
(54:05, Doug DeVos) -
On the team as the source of excellence (57:22):
"Hospitality is a team sport ... Any leader who isn't spending a majority of their time thinking about how to train and educate and even more importantly, inspire the people on their team isn't a leader. They're just a manager."
(57:22, Will Guidera) -
On collective pursuits:
"All of the pursuits, Kevin, they're all collective pursuits. Full stop ... we can collectively pursue those things. People crave a sense of ownership."
(59:23 - 59:55, Will Guidera) -
On the power of inspiration (60:02):
"TED Talks are so famous and popular because very few people have anyone in their lives who actually has answered the call to inspire them. If people work for you, you have a responsibility to inspire them."
(60:02, Will Guidera) -
Newt Gingrich on effectiveness and management (61:15):
"I tell everybody who's interested in leadership that they should buy in paperback Drucker's The Effective Executive. 167 pages. ... It's the most powerful single book I've ever read about being effective."
(61:15, Newt Gingrich) -
John Yates on discernment and humility in transition (69:42):
"The call to come to Falls Church had always been strong. The reason I never left to take any other job was God always said, you stay where you are. I'm not finished with you yet. I've still got work for you to do..."
(69:42, Rev. John Yates) -
On giving back (79:34):
"My father believed in giving back to the community ... to future generations so they would have the same opportunity and succeed that he had."
(79:34, Doug DeVos) -
On the importance of listening (80:56):
"When you want to go big, you have to really listen to ... who you serve ... If you understand who you serve, then you can leap far with them. You can't go big alone, I don't think."
(80:56, Catherine Rowe) -
Advice for aspiring leaders (76:07):
"Someone said to me, you can't drive a parked car. It's got to be rolling if you're going to steer it somewhere. So you've got to start ... move in that direction and see how it goes ... Try to discern where you have passion and pursue it in any way that you can."
(76:07, Rev. John Yates)
Memorable Quotes & Moments (with Timestamps)
-
"Make big plans. Little plans have no ability to stir men's souls."
(02:22, Kevin Gentry quoting Daniel Burnham) -
"You can't be an owner of the Dodgers, you little immigrant kid. ... You just keep going and going and going and going and doing things the right way and meeting people and developing a reputation and be honorable. And then it's like things just happen."
(06:02, Newt Gingrich) -
"If you knew you couldn't fail, what would you do?"
(06:55, Kevin Gentry, quoting Will Guidera's father) -
"We didn't think about failure at all. We didn't have anything. Why would we care?"
(07:32, Jeff Rosenthal) -
"If you want this, don't take no for an answer."
(26:43, Marilyn Diamond via Todd) -
"Her effort changed my life. And it was so inconsequential to her that she didn't even remember doing it. That's the asymmetry about what it means to believe in people."
(33:45, Todd) -
"You're never too young to be a mentor, and you're never too old to have a mentor."
(36:00, Doug DeVos's father) -
"You can't go big alone. I don't think. You can't scale something alone."
(80:56, Catherine Rowe) -
"Don't go it alone."
(78:46, Rev. John Yates)
Important Timestamps
- 02:22 — Kevin Gentry’s anniversary intro and the Daniel Burnham quote.
- 04:20 – 06:18 — Newt Gingrich on entrepreneurship and risk.
- 06:55 – 09:42 — Jeff Rosenthal and imposter syndrome; productive view of failure.
- 19:03 – 30:45 — Todd’s narrative: high school flunk-out to Harvard doctorate, and the power of mentors (Marilyn Diamond).
- 33:45 — The “Marilyn Diamond effect” on believing in people.
- 36:00 – 38:32 — Doug DeVos on mentorship at every age.
- 40:30 – 41:44 — Doug DeVos and John Pope on the multigenerational effect of mentorship.
- 42:32 – 46:02 — Insights on mentorship from Rush Limbaugh.
- 48:35 – 49:52 — Newt Gingrich’s life-changing teacher and college aspirations.
- 54:05 – 59:18 — Doug DeVos and Will Guidera on believing in people and team leadership.
- 61:15 – 62:49 — Newt Gingrich recommends The Effective Executive and discusses management philosophy.
- 69:42 – 78:47 — Reverend John Yates on leadership transition, mentoring younger leaders, and community building.
- 80:56 – 82:40 — Catherine Rowe on listening as the heart of leadership.
Episode Tone and Style
The episode is upbeat, humble, and inspiring—with Kevin Gentry offering gratitude, genuine curiosity, and a mission-driven perspective throughout. Guest voices range from humorous and self-deprecating to deeply reflective and purpose-filled. The atmosphere evokes a community of learners and doers energized by stories of growth, resilience, and going big.
Summary and Takeaways
- Risk is fundamental: Failure is an inevitable, even essential, step on the entrepreneurial path. Courage and persistence trump credentials.
- Mentoring is everywhere: Anyone can be your mentor (even unawares); anyone can be a mentor to others, regardless of age, status, or proximity.
- Bold leadership is collaborative: Inspiring and unlocking the potential within teams—and not just oneself—is the hallmark of great leadership.
- Listen and serve: The best leaders are active listeners who seek to understand and serve their communities.
- Pay it forward: True impact is found not just in self-fulfillment but in elevating and empowering others along the way.
Final Thought:
"The only things that stand in the way of really making a contribution are those barriers that we self-impose. Let's keep on Going Big."
(Kevin Gentry, 82:50)