Going Big! with Kevin Gentry

Episode: Going Big with Gay Gaines: The Woman Behind the GOP Revolution and the Revival of Mount Vernon
Date: January 5, 2026
Host: Kevin Gentry
Guest: Gay Heart Gaines

Episode Overview

In this inspiring episode, Kevin Gentry sits down with Gay Heart Gaines—trailblazer, philanthropist, and influential leader in American civic life. Gaines shares her journey from a global childhood to the helm of pivotal organizations, including the National Review Institute, GOPAC (with Newt Gingrich), and the Mount Vernon Ladies’ Association, which she led through a transformative $100 million revival. The conversation spans mentorship, leadership, historic preservation, political strategy, and what it means to “go big” for a cause you believe in.

Key Discussion Points & Insights

Gay Gaines’ Early Life and Global Perspective

• Background: Born in Toronto, she experienced a nomadic childhood, living in Australia and Paris due to her father’s career with Colgate-Palmolive.
  • “We went to Hawaii, to Fiji, to New Zealand, and landed six in the morning going under the bridge in Sydney harbor. And I was 10 years old.” (03:37–04:23)
• Influence: Exposure to diverse cultures gave her a broad worldview, later informing her leadership and patriotism.

Roots of Patriotism and the Power of Teachers

• Pivotal Moment: Gaines credits her American History teacher at Kent Place School, Ms. Sampson, for igniting her love of America and of George Washington:
  • “She would talk about the redcoats were in Manhattan and they were about to come on the island...just the way she painted the pictures. You were always pulling for George. That teacher changed my life.” (06:03–06:51)
• Mentorship: Both Gay and Kevin reflect on the outsized impact great teachers and mentors can have on a young person’s trajectory.
  • “Teachers have that opportunity, if they're great teachers, and take it. So it's a wonderful profession.” (07:18)

The Power of Role Models: Buckley, Thatcher, Gingrich, Limbaugh

• Attraction to Success: Gaines has always been fascinated by what makes exceptional people tick, citing her meeting with violinist Yehudi Menuhin as a ten-year-old.
• William F. Buckley and National Review Institute:
  • Organized a transformative gathering that led to the founding of the Institute, with Bill Buckley as chairman. (09:17–09:51)
  • Buckley’s brilliance, humor, and willingness to expand the reach beyond a small readership were key, as was Gay's initiative.
• Margaret Thatcher:
  • Developed a close friendship with the Iron Lady, learning the importance of self-confidence and deep conviction in politics.
    • “She never let the fact she was a woman stop her...” (12:41)
    • "She had such self confidence and she believed in what she believed. She wasn't just mouthing the words. That's key, Kevin." (13:07)
• Newt Gingrich and GOPAC:
  • Recruited by Gingrich to help train Republican candidates at every level, focusing on coherent messaging and strategic unity:
    • “The key is, I think that they're all talking off the same page. So Newt taught them what to say, basically.” (14:35)
    • Use of cassette tapes for standardized messaging led to national success. (14:47)
  • Gaines played a vital role as a “fundraiser extraordinaire,” connecting donors with the cause and generating much-needed resources.
• Rush Limbaugh:
  • Described as “a gentle giant”—shy in person, but a powerhouse communicator on air.
    • “Rush was a very shy man...when he got behind the Abbey Mike, he was fat. And when he left the studio...he was a different person, very shy.” (18:16–19:29)
    • His authenticity and honesty were core to his national influence.
    • “Wouldn't have happened without Rush.”—on Gingrich’s 1994 victory (19:57)

The Revival of Mount Vernon

• Leadership at Mount Vernon: As regent, Gaines spearheaded the transformation of Mount Vernon into a modern, dynamic educational hub.
  • Recognized the need for a proper George Washington Presidential Library and drove fundraising for a $100M+ expansion.
• On Fundraising:
  • Stressed the privilege and honor of inviting people to contribute, often engaging donors by showing the site in person.
    • “I think that people that give you a lot of money to do something noble deserve to have their name on it.” (25:24)
    • “There's only one Mount Vernon, and people give to all sorts of things, but there is only one George Washington's home, and it needs to be spectacular.” (26:09)

On American Values and the Future

• What Gay Wants for America’s Next Generations:
  • Strives for her descendants to see “the good” in America—its exceptional founding, generosity, and decency.
    • “Every time I come home to America, I see really decent people and good people, all walks of life...” (28:22)
    • “America's founding is important because it was founded differently than any other country...There’s no other country like America.” (28:55)
  • Celebrates the upcoming 250th anniversary as an opportunity for renewed patriotism and historical appreciation.

Notable Quotes & Memorable Moments

• On Mentorship:

  • “Teachers have that opportunity, if they're great teachers, and take it. So it's a wonderful profession.” (07:18, Gay Heart Gaines)

• On Conviction in Leadership:

  • “She never let the fact she was a woman stop her from trying anything... she believed in what she believed. She wasn't just mouthing the words. That's key, Kevin. The politicians today, the ones that I admire and gravitate toward, you know, they have a deep conviction, they mean it.” (13:01, Gay Heart Gaines)

• On Fundraising Philosophy:

  • “The key is to ask wealthy people. There's no point in going to people that aren't if you need to really raise a lot of money...It's a privilege.” (16:11, 23:33, Gay Heart Gaines)
  • "Think about Mount Vernon. There's only one Mount Vernon, and people give to all sorts of things, but there is only one George Washington's home, and it needs to be spectacular. So they got it." (26:09)

• On Confidence and Action:

  • “When you believe something strongly, do it... When I wanted somebody to help me, I asked. And I don't think you should not ask.” (30:55, Gay Heart Gaines)

• The Famous 'Garbage Bag' Scene:

  • Gay recounts a night at GoPAC, trapped in an elevator filled with Christmas party trash at 11:30 pm, illustrating her relentless commitment.
    • “I have to climb over the garbage... I lost a beautiful shoe that I never found again because it came off from the garbage bag.” (34:41, Gay Heart Gaines)

• On Building Teams and Commitment:

  • “I remember walking into the room and looking around this big, long table, and there were 30 young kids with pizzazz... I kept eight people out of 30. And I told Newt, we just cut the payroll. And then I said, now we have to raise the money. Those kids were so fabulous. And I got to work every morning at 8, and I was always the last one to leave. And they got a message of somebody who was committed.” (00:01, 34:32, Gay Heart Gaines)

• On Going Big, and Fearlessness:

  • “Be fearless. Just tackle whatever it is, knowing you can make it better and just do it. Don't have excuses why you can't... You will fail sometimes, but that's okay.” (38:10, Gay Heart Gaines)

Important Segments & Timestamps

• [03:37–06:03] — Gay’s childhood around the world, and how it shaped her worldview
• [06:03–07:18] — The teacher who made her a patriot
• [09:17–10:25] — The start of National Review Institute, Buckley’s influence
• [11:21–13:33] — Margaret Thatcher’s friendship and leadership lessons
• [14:16–16:45] — GOPAC’s founding, Newt’s strategy, and building a winning team
• [18:16–19:57] — Rush Limbaugh, his shyness off-air, and his cultural impact
• [21:06–26:30] — Mount Vernon’s revival, fundraising philosophy, and visionary leadership
• [30:19–34:32] — Practical insights on courage, leadership, and building great teams (with the “garbage bag” anecdote)
• [36:42–38:10] — Final encouragements: “do it,” assembling the right team, the power of fearless action

Key Takeaways & Lessons

• Mentors and role models matter—great leadership is forged in part by inspiration from exemplary individuals.
• Conviction, self-confidence, and persistence are crucial for “going big.”
• In fundraising, treat the ask as a privilege and invite others into partnership for something greater.
• Surround yourself with committed, “like-minded” people; prune teams for quality and passion, not just quantity.
• Be fearless, take risks, and understand that failures are part of the journey.

Final Word

“Be fearless. Just tackle whatever it is, knowing you can make it better and just do it... You will fail sometimes, but that's okay.” — Gay Heart Gaines (38:10)

For more episodes and resources, visit goingbigpodcast.com.