Podcast Summary: RKD Group Thinkers — The Journey to Fundraising $3 Billion and More with Kevin Gentry

• Podcast: RKD Group: Thinkers
• Host(s): Justin McCord, Ronnie Richard
• Guest: Kevin Gentry (CEO of 10X Strategies, Host of Going Big Podcast)
• Release Date: May 15, 2025

Brief Overview

In this episode, hosts Justin McCord and Ronnie Richard dive deep into the world of large-scale fundraising with Kevin Gentry, a renowned nonprofit fundraiser credited with helping to raise over $3 billion across his career. The conversation explores the evolution of nonprofit fundraising, the career paths into the sector, the mindset required to “go big,” and how mentorship, risk-taking, and community-building are key to meaningful impact. Throughout, Kevin’s storytelling and humility shine as he shares memorable anecdotes and lessons from decades at the forefront of philanthropy and direct response marketing.

Key Discussion Points & Insights

1. Kevin’s Journey to $3 Billion (03:46–08:29)

• Humility in Achievement: Kevin clarifies he "helped raise" $3 billion, emphasizing the generosity of donors and the power of teamwork.
• Early Stories:
  • First major gift ask: Nervously asked for $50,000 and accidentally asked for $500,000 due to an extra zero — the donor agreed.
  • Key mentors included Charles Koch and Rich DeVos, who inspired his approach to scaling giving campaigns.
• Quote:

  “I want to be clear, I've helped raise $3 billion...I was really fortunate over the years to be involved with just some extraordinary people.” — Kevin Gentry (03:46)

2. Falling into Fundraising & the Lack of Industry Pathways (08:29–12:41)

• Accidental Entry: Like many, Kevin “fell into” fundraising, noting almost no young person deliberately seeks a career in nonprofit fundraising due to lack of awareness and formal training opportunities.
• Mentorship Role: Early mentor Morton Blackwell allowed Kevin to move into fundraising at the Leadership Institute.
• Quote:

  "No young person is given any expectation that they could be involved in a professional career in nonprofit or fundraising, with some just rare exceptions." — Kevin Gentry (10:32)

3. Lessons Learned & What Makes Fundraising Meaningful (12:41–17:00)

• Professional Reflections:
  • Fundraising connects those addressing society’s root problems with those having the means to help, creating partnerships that yield deep meaning.
  • Many philanthropists find more purpose in giving than in their own business successes.
• Quote:

  “Many people can get a much greater sense of meaning and purpose in their lives in working with a partnership to solve a big problem than maybe even they did in creating a great business.” — Kevin Gentry (13:18)

4. Barriers to Entry and The Need for Exposure (17:00–18:49)

• Career Discovery Challenges: It’s unrealistic to expect young people to “follow their passion” into fields they don’t know exist, underlining the need for better industry exposure.

5. Philanthropy Trends: Rapid Change & Consistency (18:49–21:35)

• Technology’s Impact: Society and fundraising are changing rapidly due to technology and faster information sharing, but the fundamental desire for meaning and relational, not transactional, giving remains.
• Quote:

  “I think many people are finding that philanthropy is an effective vehicle to [live a life of meaning and purpose]...I don't think we're moving from transactional to relational fundraising. It's always been the case.” — Kevin Gentry (18:58)

6. Direct Marketing: Lessons from the Legends (21:35–33:24)

• Direct Response as Leveraging Relationships:
  • Direct mail evolved as a means to scale what works best: one-on-one connection.
  • Strategic storytelling about iconic campaigns and mentors like Morton Blackwell, Mal Warwick, and Richard Vigory.
• Key Package Stories:
  • Dick Armey Letter for the Leadership Institute: A direct mail acquisition piece that broke all previous records despite initial skepticism.
  • The power of giving societies and emotionally engaging donor events.
• Mentorship Again:
  • Kevin stresses actively seeking out mentors, both older and younger, and continuously learning.

7. The Untapped Power of Community (33:24–33:49)

• Building Communities of Fundraisers:
  • The most significant opportunity ahead is fostering a community of principled fundraisers, leveraging shared knowledge and support.

8. 10X Strategies & Going Big Podcast: Vision for the Future (33:49–37:35)

• Filling the Talent Gap:
  • The sector’s primary constraint is experienced talent; Kevin aims to spotlight leadership stories that inspire big thinking and risk-taking.
• Vision & Leadership:
  • Big social change is tied to bold vision and leadership, invoking historical examples and the importance of inspiring others to dream and act large.
• Quote:

  "If we can encourage more people to think big and go big, I think we're going to get to the root causes of more of the problems in society today." — Kevin Gentry (37:23)

9. Mindset Shift: From Scarcity to Abundance (37:35–41:27)

• Risk Aversion in Nonprofits:
  • Many leaders in the nonprofit sector are risk averse, stemming from resource constraints and a cautious culture, but major leaps are tied to embracing risk.
• Business Lessons:
  • Stories of entrepreneurs like Art Ciocca (creator of Franzia box wine) illustrate that risk-taking underpins breakthrough success.
• Quote:

  "These enormous success stories almost always go back to thinking big and risk taking. And if we can somehow marry that in the nonprofit sector...biggest problems we face in society...are at risk of being solved.” — Kevin Gentry (40:55)

10. Call to Action and Closing Reflections (41:27–44:19)

• Empowering Leaders:
  • The hosts express gratitude for Kevin’s work in empowering leaders and shifting the nonprofit mindset; Kevin calls for collective action to address society's most pressing challenges.
• Quote:

  “If we all learn how to be better fundraisers, we’re all going to do better at solving these problems in society.” — Kevin Gentry (44:01)

Notable Quotes & Memorable Moments

• “Maybe you don’t belong in this room.”
  — British major gift trainer to a young and nervous Kevin (04:24), on the mindset required for big asks.

• "I've never been asked for $50,000 in my life." “That’s okay. Kevin’s never asked for $50,000 either.”
  — Exchange with a donor and Kevin’s colleague (05:09), highlighting humility and humor early in his career.

• “Direct response is leveraging that one-on-one meeting.”
  — Kevin Gentry (23:25), on the strategic purpose of direct mail and direct response.

• “I have learned also as I've grown older that I find more and more mentors who are younger than me, who are teaching me in other areas. You can have mentors in all different kinds of areas.”
  — Kevin Gentry (25:06), on lifelong learning and the importance of mentorship.

Selected Timestamps

| Segment | Content/Theme | |---------|---------------| | 03:46–08:29 | Kevin’s first major asks, humility, key mentors & fundraising stories | | 10:32 | Reflection on lack of direct pathways into fundraising for young professionals | | 13:18 | On the deeper meaning and purpose found in fundraising | | 18:58 | Philanthropy trends and the enduring importance of relationships | | 21:56 | Why direct marketing endures & lessons from direct response pioneers | | 24:51–33:24 | Legendary direct mail stories & the role of mentorship | | 33:49–37:35 | Kevin’s new venture (10X Strategies), vision for the sector, “Going Big” philosophy | | 38:03–41:27 | Mindset shift: tackling risk aversion in nonprofits, business lesson case studies | | 44:01 | Final call to action on why better fundraising can change society |

Tone & Atmosphere

The conversation is candid, insightful, and down-to-earth, with self-deprecating humor, rich storytelling, and a clear passion for raising the sector’s leadership bar. Kevin’s humility and sense of mission, paired with the hosts’ camaraderie and curiosity, make the episode both informative and inspiring.

For Listeners New to the Episode

This episode is an essential listen for nonprofit leaders, fundraisers, and anyone considering a career in philanthropy. It offers a deep dive into the trials, triumphs, and lessons from one of the sector’s most experienced voices. Listeners will walk away energized to think bigger, seek mentors, and foster a mindset of abundance that drives real-world impact.