Welcome back to the Lead with Heart podcast. I’m very honored to have Jake Wood as my guest today. Jake is a Marine Corps veteran and the founder and CEO of Groundswell- a software company that enables companies to help their employees become modern philanthropists by providing tech-enabled donor-advised funds. Prior to launching Groundswell, Jake served as the founder and CEO of Team Rubicon, a disaster response organization that is widely considered one of America’s leading nonprofits.
We discuss scaling an organization, the importance of storytelling in fundraising, developing a strong corporate culture, and the future of philanthropy.

In this episode:
- [01:15] Jake’s background and what led him to found Team Rubicon and Groundswell
- [07:16] Founder syndrome and delegating responsibilities
- [12:07] Instilling a strong corporate culture
- [15:52] Strategies to maintain a strong company culture throughout scaling
- [19:52] Strategies for scaling your nonprofit
- [23:36] The ethics of storytelling
- [27:37] Donor-advised funds and nonprofit collaboration
NOTEWORTHY QUOTES
“Organisations are no different than any living organism. If they’re not constantly evolving, then they’re just slowly dying.”
“It’s incumbent upon a CEO, not just to define the values of an organization to the culmination of your culture, but to then ensure that every element of how you operate reinforces those values.”
“Culture is what guides people’s decisions in the absence of orders.”
“Most people, whether they want to admit it or not, they want to be a part of a strong, powerful culture, a tribe, a community of like-minded people.”
RESOURCES
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CONNECT WITH JAKE
Jake is the founder and CEO of Groundswell – a venture backed software company aiming to democratize philanthropy by building a new category at the intersection of fintech, benefits tech, and charity. Prior to launching Groundswell, Wood served as the founder and CEO of Team Rubicon, a disaster response organization that is widely considered one of America’s leading nonprofits. Before this, Wood served four years in a Marine Corps scout-sniper unit, leading Marines in combat in Iraq and Afghanistan. He is a graduate of the University of Wisconsin with a dual degree in Business and Political Science. Jake’s memoir, Once A Warrior, was an Amazon best-seller.
LinkedIn: Jake Wood
Instagram: @jakewoodtr
Website: jakewood.co, groundswell.io, and teamrubiconusa.org
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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