Welcome back to the Lead with Heart podcast! In today’s episode, find out why one consultant dressed in drag to motivate volunteers and learn the importance of making fundraising fun again.
Guest Rob Webb, a seasoned nonprofit consultant with over 35 years of experience, discusses the sustainability of fundraising efforts through volunteer-led campaigns. By empowering volunteer leaders to spearhead fundraising initiatives, nonprofits can navigate challenges stemming from staff turnover more effectively.
Rob discusses defining a culture of philanthropy over charity and the importance of passion for the mission. We discussed key techniques like making the ask comfortable, involving all organization levels, and viewing rejection as an opportunity.

In this episode:
- [2:30] Rob’s unexpected journey into nonprofit fundraising from swim coach to consultant
[7:21] Defining the culture of philanthropy vs charity and the importance of passion for the mission
[13:31] How volunteer-led campaigns empower donors and sustain fundraising efforts
[16:40] Techniques for training volunteers to feel comfortable asking for donations
[25:47] Involving all organization members in fundraising – from executives to frontline staff
[35:07] Viewing rejection as an opportunity
[36:03] Setting up sustainable systems so campaigns continue despite leadership changes
NOTEWORTHY QUOTES
“We all need to be making a conscious choice to support our employees, to invest in our employees.” -Rob Webb
“For a volunteer, they’ve got to make a mental decision that their love and passion for their organization is greater than their fear of asking for money.” -Rob Webb
“Asking is just telling your story and saying, ‘Hey, will you join me?’” -Rob Webb
“We have given them the best form of advertising for their organization which is word-of-mouth advertising from a volunteer who’s passionate and gives their own money.” Rob Webb
RESOURCES
Take the leap into successful fundraising with the Savvy Fundraiser Fundamentals Course. The ultimate guide designed for nonprofits that have been around for a while, but haven’t delved into the world of fundraising yet. This course covers everything from crafting compelling campaigns to collaborating effectively with your team, ensuring you have all the tools you need to elevate your fundraising efforts.
Are you ready to become an emotional connection master?
The EmC Masterclass developed by Dr. Lola Gershfeld is for everyone looking to enhance their communication and collaboration skills to raise more revenue for their mission. This groundbreaking Emotional Connection process has been integrated into top universities’ curriculum and recognized by international organizations like ICF HRCI, and SHRM. Use the code LEADWITHHEART to enjoy a generous 10% discount.

CONNECT WITH ROB
Rob Webb is the President and CEO of Rob Webb Associates. He has over 35 years of experience in nonprofit fundraising, management, and aquatics. He got his start in fundraising unexpectedly while working for the YMCA, and went on to become a Certified Fundraising Executive. Rob now runs a consulting firm helping nonprofits with fundraising, public affairs, and more.
LinkedIn: Rob Webb
CONNECT WITH HALEY
Haley is a Certified Fund Raising Executive (CFRE), Certified Stress Management Coach, and Certified EmC train the trainer. She is the Founder of The Savvy Fundraiser, a nonprofit consulting and coaching business. She has worked in both small and large nonprofit teams in the human services, homelessness, and youth sectors; and she specializes in the EmC process, nonprofit leadership, board development, and fundraising. Haley is a passionate, impact-driven, experienced nonprofit professional whose mission is to empower, elevate and engage nonprofit leaders to build healthy, thriving organizations.
Instagram: @thesavvyfundraiser
LinkedIn: Haley Cooper, CFRE
Website: thesavvyfundraiser.com
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