The Future of Philanthropy
The United States is the most charitable country on earth, but the systems and technology in place for giving are rife with inefficiencies. The state of corporate matching programs is a major culprit, with estimates of as much as $5–7 billion of eligible donations going unmatched. Jake Wood, founder and CEO of Groundswell, saw an opportunity to do better for average Americans, who give a much larger share of their take-home pay to charity than the ultra-wealthy, but don’t have access to the same resources and benefits.
Groundswell unlocks philanthropic giving at scale by making charity an employee benefit, giving people the power of a personal foundation in the palm of their hand: a 401K for giving.
Service has been at the core of Jake Wood’s life and career since joining the U.S. Marine Corps after a Division I college football career. Shortly after Jake returned home in 2010 from two tours in Iraq and Afghanistan, Haiti was struck by a devastating earthquake. As traditional aid organizations struggled to deploy relief efforts, Jake quickly mobilized a team of veterans and doctors to help on-the-ground. That effort evolved into Team Rubicon, the disaster-response organization Jake led as CEO for 12 years before founding Groundswell. Under Jake’s leadership, Team Rubicon grew to over 150,000 volunteers, responded to nearly 1,000 disasters, raised nearly $300 million for their work, and was named one of the best places to work.
In honor of both Veterans Month and giving season, we sat down with Jake to talk about moving from Team Rubicon to building a technology startup, and the leadership lessons he’s bringing with him.
You’ve lived a life of service, from the U.S. Marine Corps to building Team Rubicon. How has this path led you to Groundswell?
Service and impacts have always been really important to me. At the same time, I always knew in my heart that I was an entrepreneur. In my decision to leave my post at Team Rubicon, I knew I wanted to start something again, and I was concerned that I wouldn’t be able to come up with an idea that would still serve the greater good. I feel really lucky that I was able to take what I’d learned as a first-time entrepreneur building and raising money for Team Rubicon to come up with the idea that has become Groundswell.
Groundswell puts the power to solve the world’s problems into the hands of the many, rather than the powerful few. Why do you believe that will work?
The issues facing our communities are inherently local. With an issue like homelessness, there are systemic issues that we need to address, but at the end of the day people sleeping on the street need a place to sleep, and that’s a local issue. I think that there are a lot of inefficiencies in identifying local solutions to what are naturally local problems.
We’re not aiming to replace large, systemic philanthropy. Some problems have to be solved systemically with major infusions of capital. All too often, though, that doesn’t happen because billionaires are trying to get to Mars instead of solving real-world problems.
Why are you starting by working with employers?
In my experience at Team Rubicon, I saw just how tragically complicated and inefficient corporate matching programs are. I got the idea for Groundswell late at night, as most ideas typically come. I started thinking about this idea of upending corporate matching using a traditional donor-advised fund (DAF) approach.
There have been a lot of people who have tried to create new and novel ways to give to charity and a lot of them never scaled. Right away, I knew it was not a technology problem. It was immediately a scale problem. That was really the impetus for what has become our primary go-to-market strategy.
What is the state of charitable giving in the US right now? What does it look like after Groundswell?
America remains the most charitable country on the planet — and it’s not even close. There’s a few trends that are happening. More and more people are giving online, but there’s a ton of inefficiencies in online donations, mostly due to transaction costs. Additionally, there’s estimates that as much as $5–7 billion of eligible corporate matches go unmatched, which is mostly due to the horrific state of existing matching platforms.
The average American is giving a really meaningful portion of their take-home pay to charity, relative to the ultra-rich. Our hope is that we make that as efficient as possible so they’re getting the most bang for their buck. These are precious dollars that average Americans are sending out to charity, and it’s unfortunate that they don’t have the same resources that ultra-rich people do. I think we can make the pie more efficient, but I think we can also increase the size of the pie.
How has your journey been from the non-profit sector to the for-profit world of Silicon Valley?
After having some of our initial fundraising calls, I called Heather Hartnett and said, “Heather, raising money is so easy.” She told me, “Now you realize that when you were running a nonprofit, you were training with ankle weights on.” That was the perfect way of putting it.
I think for-profit companies are much simpler. You have direct relationships with your customers, you build a great product, and the customer pays you directly for it. In the non-profit space, you build something great and ask somebody else, who isn’t directly benefiting, to pay for it. I’m really excited about the elegant simplicity of building a company — and that we’ll have a significant war chest to do it early. It took me four years at Team Rubicon to raise what I’ve been able to raise in four months at Groundswell.
What are the top tenets for leadership that you’re bringing from Team Rubicon to Groundswell?
We’re really focused right now on building a foundation that’s rooted in our people. We’re making a very deliberate decision to build an in-person culture. In the aftermath of COVID, that makes finding talent a lot harder. We knew that was going to be the case when we made the decision, but our hypothesis is that having an in-person team will be a strategic advantage in the coming years and that the headwinds we see now will become tailwinds in the future.
We made that decision because we believe culture will be critically important. Startups inherently move faster, and it’s key in those environments to build a culture where everyone is aligned to the same vision — where in the absence of a plan, you are consistently getting to the right decision and the right outcome.
You have a proven ability to attract and rally strong teams around you, and create deep conviction in what you’re building. What’s your strategy for building strong teams?
Storytelling is one of the most underutilized tools in a leader’s toolkit. If you think of your company like a story, it’s got a beginning, a middle, and an end, it has characters, protagonists, and antagonists. Unfortunately, it also has plots and twists and unexpected turns. If you treat your team like they’re just unnamed characters in the story, then they’re going to show up like unnamed characters and they’re going to put in unnamed-character effort. If you treat them like a consequential character, if you give them a name, an opportunity to impact the plot, and treat them like a hero, then they show up like a hero.
Human beings want to be part of a story. Great leaders give people that opportunity.
Who inspires you?
I remain inspired by the incredible volunteers that I had the opportunity to work with at my last company, Team Rubicon. Collectively, they were the most selfless and change-driven people I have ever met. Countless times they would drop everything to fly to a community they’d never been to in the aftermath of a storm, all for the chance to make a difference on the worst day of a stranger’s life. Our nation could use more people like them.
Interested in joining Groundswell’s mission? They are hiring across product, sales, and technology. See open roles here.
