In this episode of the RKD Group: Thinkers podcast, hosts Justin McCord and Ronnie Richard sit down with Gabe Cooper, founder and CEO of Virtuous, for an insightful conversation on the intersection of technology and generosity.
Gabe shares his journey from software development to the nonprofit sector, reflecting on lessons from past failures, the importance of leadership and maintaining work-life balance. They also discuss the evolving future of fundraising, including AI’s role in strengthening donor relationships and optimizing nonprofit operations. With a mission to drive $10 billion in new generosity, Gabe’s passion for making a meaningful impact in the nonprofit world is at the heart of this discussion.
Gabe shares:
- His journey, which includes a blend of technology and nonprofit work.
- How generosity was instilled in him from a young age by his parents.
- The importance of pattern recognition in technology and music.
- How learning from failures is crucial for growth in entrepreneurship.
- That leadership requires defining reality and empowering your team.
Show chapters
- 02:48 The Intersection of Nonprofits and Technology
- 06:05 Gabe's Journey: From Software Development to Nonprofits
- 08:51 Learning from Failures: Insights from Past Startups
- 12:06 Leadership in the Nonprofit Sector
- 14:48 Work-Life Balance as a CEO
- 18:08 The Importance of Durable Friendships
- 21:09 Memorable Impact Stories from Virtuous
Meet our guest
Transcript
Justin McCord
All right, Gabe, I warned you that we were gonna talk about you, so ... unless you want to phone a friend and have us talk to them about you. But, no, I mean, I've been thinking about, like, there's a lot of stuff that I wanna understand and unpack, but I wanna start with: Where in the world did the idea of combining nonprofits and technology, like, when did that pop on your radar? What was the moment that that was like, yes, this is the course I wanna go?
Gabe Cooper
Yeah. Yeah, yeah, it's a good question. I, this … probably there's an evolution, probably a few different moments in time, but early in my career, I worked ― I'm old, so I was a software developer in the first .com boom and bust and love software development, love building product, but then, as you might imagine, like, I got a little bit disenfranchised. There were a lot of routines and a lot of dumb decisions that weren't necessarily good for the world back in the late ‘90s, early 2000s, and so I had this, it's like, there's gotta be more meaning than this, the stuff I'm doing right now.
So that was sort of one moment. I actually went to work in the nonprofit space, and I think that that made me think, well, I really like nonprofits, and also I work at a slightly faster pace than most of these organizations, and I wanna have an impact beyond just one nonprofit.
And I think, probably, the third moment was, for about eight years, I ran an agency ― I did custom software development, some digital fundraising kind of stuff. And I think we just got our, got a lot of pattern recognition working with a lot of big nonprofits, like, very common tech challenges that were standing in the way of generosity. I mean, we go from one organization to another having to build custom stuff on top of their existing tech stack just to help them do the bare minimum of the right thing to do for their donors.
I'm like, gosh, this is ridiculous. All of these orgs are handcuffed to tooling data systems, even how their teams are structured, that are preventing them from growing the way they need to grow to serve their mission. I think it just grew out of frustration of seeing that year after year after year; it's like, somebody has got to fix this problem. And then, at some point, it just hit on me: Oh shoot, maybe you're the one that's supposed to help fix this problem.
That happened about ten years ago, but I think for me, more than anything, I, my like, personal passion in life is generosity. Right? So like, not just … part of it's the, these organizations we get to work with, they're doing amazing work and generosity funds at work. But a lot of it, for me, is actually what it does in the heart of the donor. Right? So, when people give away their, their time or their money, they, they tend to be a lot less selfish, a lot more focused on their neighbor, which in the world we live in seems to be a pretty valuable thing. And so, I think that's the thing that kind of animates me and gets me up every morning.
Justin McCord
Yeah.
Ronnie Richard
I think you're saying there's like, a Venn diagram of you that's a cross of generosity and technology. When you were younger, as a kid, did you notice a lean toward either of those two things? Like, a lot of times, someone who grows up to be an engineer, they, as a kid, they take things apart, and they were constantly tinkering with things. Were you drawn into software and developments early or anything like that?
Gabe Cooper
Yeah, it's an interesting question. I've thought some about that. I mean, I grew up in like a, a sort of a faith community in my household. My parents were very, very generous people, always thoughtful of others. So I think I saw that modeled in an early age for my parents on the generosity side. On the tinkering side, it's funny, like, a lot of software engineers, you'll find this, but they're actually drawn more toward music. So yeah, tinkering, like I was good in physics and math. I liked, you know, I liked building. But it's actually the creative energy around music. You walk into any room of 20 software developers, I guarantee you half of them are musicians. There's just something about that. And so I like, I always loved music as a kid, and I love creating music, so it's a weird connection between the two, but there's something about this like, craftsmanship-plus creativity that just like, fires up something in my brain that I really like.
And so I, as weird as it sounds, it may have actually been music that drove me more toward that sort of desire to build.
Ronnie Richard
A blend of structure and creativity.
Justin McCord
It's interesting you say that because, well … and you used the phrase “pattern recognition” earlier, which, my mind immediately goes to music whenever you said that. What do you play?
Gabe Cooper
I don't play anything well, but I played for years. I played in bands, and I played guitar, bass, mandolin, a few different things and had a small record label in my early twenties. That was a complete train wreck. I couldn't make a dime off of it, but it allowed me to produce music in my house for several years, which was fun.
Justin McCord
So, okay, so I actually had no idea. That's awesome. This is the kind of stuff that I love getting into. I knew about Brushfire as an agency and then obviously knowing about Virtuous, but even starting a record label. So, you're a serial entrepreneur.
Gabe Cooper
Yes, if you want to count the record label, then yes. And so that's my, you know, that's my, get your massive failure out of the way early on. And so, you can figure out how to do the right kind of stuff. And so, yeah, that, those … and then we had a, had a mobile app company with, with two buddies that was, we made mobile apps for golf, primarily, but then a few other sports as well. So Virtuous is technically my fourth, but it will definitely be ...
Justin McCord
Right? Hmm. Right?
Gabe Cooper
… my last. Now, number one, because it fulfills a personal passion for me that I just love. But number two, like, you just get to a certain age where starting with a blank sheet of paper again, it just is overwhelming.
Justin McCord
Yeah.
Ronnie Richard
You mentioned those “learning from failures.” Like, what did you learn from those? Sorry, what did you learn from those startups that didn't take off? Like, what have you applied lessons to what you're working on with Virtuous today?
Justin McCord
Well, and this one, go ahead, Ronnie.
Gabe Cooper
Yeah. I mean, I think with all, all of my companies, there have been like, sort of miniature failures, or sheer panic moments or existential crises along the way. And I think there's probably learnings. I mean, in that initial record label, I realized really quickly, hey, you have to, number one, you have to be really good at something. I think I was very mediocre, but, number two, like, just sort of business fundamentals are a little bit lost on you in your early twenties. Like you have to sell stuff for money, and you have to make more money than you spend. Right? A lot of times, like, you can see this in early startup founders. There's this sort of like, dream-big aspirational vision of the universe, which I absolutely love, but it's sometimes not anchored to like, the fundamentals of you have to build something that people will buy, and you can't spend all of your money. You know, it's, it's weird to say that, but I think that's a pretty common trait for people in their early twenties.
Justin McCord
Yeah, that maturation process is fascinating, you know, whenever you can, when you're in a place where you can look back on it and see those growth steps and those growth lessons. Now that you have, you all have experienced a tremendous amount of success and been able to make a dent for so many nonprofits in terms of what they accomplished through, you know, connected infrastructure.
How do you think about, as the leader, as the CEO of an organization that has high visibility in a relatively large sector ― it feels small at times, but it’s a relatively large sector ― how do you think about what that looks like to lead and have that founder-led approach in the market?
Gabe Cooper
Yeah, it's interesting, especially in B2B SaaS. I think if you look at vertical software as a service generally and the nonprofit space and other sectors as well, there is always this, sort of, fear of losing your soul. A lot of times it's like, maybe private equity money that comes in, or a bunch of things being slammed together or the founding team leaving and you being left with a bunch of folks in suits that don't really know or care about your customers, right? And so that's, that's something that we have to sort of battle against every day to fight for our soul, if that makes sense. So part of it's just bringing the right people around the table and not getting out of your skis, controlling your own destiny so you can make the right decisions. And by “right decisions,” I mean, like at Virtuous and for me personally, it's always about the product and our customers, nothing else. Like, we have to do amazing research and development to build the best nonprofit products, the best products for our nonprofits, right? And so like, I hate the fact that for years, people have looked at nonprofit tech and said, yeah, that's probably 20 years behind the rest of the world. I think nonprofits should be out ahead, right? And so we have to like, sort of, hire a team and create a vision that that's really what nonprofits deserve.
And the second part is just being like, customer obsessed. Everybody on our team, we expect them to like, sort of, care deeply about the organizations that we serve. We … our customer experience team always says, default to yes, which means like, hey, if a nonprofit calls and they said, this thing stinks, you default to like, yeah, I'm gonna assume you're right about that. And I'm gonna lean in and figure out what you care about in the world. Like, you know, a lot of that, for us, means we spend a lot of time volunteering at our customers, going on site with our customers, like, working with them shoulder to shoulder.
But I think if you can sort of ingrain a culture of like, product led, customer obsessed, and that permeates the whole organization, like, it makes a big difference, and it makes it for a fun place to work too, honestly.
Ronnie Richard
You used a couple of words in there that I just want to call out. You used “obsessed.” “Customer obsessed,” and you talked about putting your soul into the work. Obviously, that's a lot of time and effort you're committing to your role as CEO, as to be expected, you know, in a leadership role like that. How do you, how do you balance that, that work-life balance, and finding time to do things outside of the office?
Gabe Cooper
I don't, I don't think I did that well early in my career. It's a lesson I had to learn. I probably ran way too hard, right? And like, burned it at both ends for too many years, which I regret in some ways. I think, you know, for me now, like, one of the things with my family is I just commit to being what I say is indispensable at home. Meaning like I'm integral to our nighttime routine at our house, and I don't want to give that up. Right? So, my 10-year-old daughter expects me to put her to bed every night. And that's just something that I'm not going to sacrifice on anymore, right, to get to that point. So, if you still want to deliver with excellence and have some sort of balance, it really means hiring really good leaders that are smarter than you. Right? So I think that's the thing, especially, I think over the last five or six years, that's been my top priority as a CEO is I have to identify and retain, attract and retain great talent. Like, I have to hire people that are all better at their job than I could ever be, and then I'm not up at 10 in the morning trying to cover off on something I shouldn't be covering off on. And so, I mean as a CEO, it really is about you have to create a very coherent vision of where you're going, then everybody has to be bought into that vision. You have to make sure you don't run out of money, but then the third, and probably the most important at our stages, yes, you have to attract and retain amazing talent and be incredibly selfish and greedy about the kind of talent you get on your team.
Justin McCord
It makes me think about a little bit of Max Dupree, and “Leadership Is an Art” is a book that I was given 10 or 12 years ago. And we talk about amongst our leadership team quite a bit that the role of a leader is to first define reality for their team. And so, whether or not that reality is like the state of play or how we want to show up for our clients, like, that … defining those pieces of reality. And the second team is, get out of their way. Like, to your point, the old David Ogilvy-ism of: Hire people that are smarter than you and get out of their way. I think those are also signs of maturation that come from time and opportunity.
Those two lessons were things that I learned from specific individuals that I watched and that I have been fortunate to be mentored by. Who … there are a lot of people that look to you in your organization and or in the sector that you have been able to speak into their lives. Who has spoken into your life over your Virtuous tenure that has mentored you and helped you grow or help you overcome unforeseen obstacles along the way?
Gabe Cooper
Yeah, I think for me, you know, me and this group of people that I hang with, we always talk about durable friendships. And so, there's a group of other CEOs and leaders that I'm not mentored by as much as, like, really good friends with that are also in the thick of it with me. And why I say use the word “durable” and “friendship” is like, somebody can read a Peter Drucker book and just tell you business truisms. But it's another thing when you have, like, folks that are actually in the trenches with you, that care about you deeply, that care about your family, that get to know you, that can actually say words that are more specific and true, right?
And so, I think being a founder and a CEO can be lonely, especially if you're a solo founder, just … you feel the weight of the world is on your shoulders. And so, I actually think that durable friendships with like-minded folks that you can be arm in arm with is actually the thing that makes the difference more than just, like, the sort of the older Peter Drucker figure in your life that's gonna just tell you business wisdom, right? I mean, all of the content is all out there and consumable. It's like the application of that content and the thick of it that matters, if that makes sense. So yeah, that's good.
And the other thing is I've been pretty ...
Justin McCord
Totally does.
Gabe Cooper
… picky about who we invite in as investors and who's on my board. And so, those relationships aren't contentious. I've even told people when they're in a more … but like, I'm going to be really transparent here. Like, I'm not going to sugar coat anything, and I need people around the table with me that are okay with that and are willing to be shoulder to shoulder with me, like, you and me against the problem. And, and by sort of having a with that dynamic at Virtuous, it's allowed me to sort of garner the wisdom of a set of folks who've all been there before and have pattern recognition.
And so, that sort of authentic transparency combined with really smart people helps.
Ronnie Richard
In your, I think, decade-plus of since starting Virtuous, you've obviously worked with a ton of nonprofits and helped them improve their fundraising, streamline their fundraising. What … are there any memorable stories or moments that stand out to you that you just recall instantly of, man, that was a great opportunity; we helped that group out with ...
Gabe Cooper
You know, I've, this is a story I've told a thousand times, but it's, I don't know why it sticks with me so much. It actually happened in the really early days of Virtuous, so for anybody listening that's heard this, I apologize, but man, it's just so cool. We have a feature in Virtuous that it's like, hey, here's the next calls that you should probably make today. So if you're like a major gift officer or something, you're just, you don't know what to do with the next 15 minutes of your life, like, here's the next, you know, ten calls you should probably make.
We had a woman who was heading fundraising for a human trafficking organization. They were about 10 grand short of being able to run this project where they're going into Southeast Asia and rescuing people out of human trafficking. And so, she was panicked. Went and got the number, pulls up that list, calls down the list, and within about 30 minutes had raised all $10,000 to be able to, to get the project rolling and was so stoked about it, she actually drove to our office and bought a couple of our software developers lunch as a way to say thank you because she had time on her hands again. And so, just like that, the dynamic of, hey, using data to drive giving in a way that like, saves you time. And then just seeing the direct impact of that in the field of people being rescued. And then having the tie back to, like, my team getting to give each other a high five and our customer a high five like, all in a 48-hour span is just pretty special. Yeah.
Ronnie Richard
ends all around.
Justin McCord
That's awesome. It's so indicative, I think, a little bit of the culture and obviously of so much of what you have been come to be known by, which is that responsive mindset, the responsive framework in the book. And it's something that even spills out in those sorts of stories, right? That, you know, the proactivity behind it and having that even a part of the features that turned into those kinds of stories. That's fantastic.
You're kind of rounding out as you look ahead over the next decade plus, and you said this is your, ideally, this is your last startup and founder scene. Who knows what that story looks like down the road, but as you look ahead, what excites you about this particular time in fundraising and where you see Virtuous helping nonprofits solve some pretty heady problems right now?
Gabe Cooper
Yeah. Yeah. There's a couple of things there. I think, broadly, our mission is we want to create $10 billion in that new generosity in the world. So we measure like, the, how much you were doing, where you were going before and how we sort of level that up. And so at this point, we've measurably created about 1.2 billion. And so, I really want to get to that, that $10 billion mark.
I think what that looks like, probably, over the next five to ten years for nonprofits is going to be leaning into things like AI. Right? So if you think about the typical problems that a nonprofit's facing, if it's around responsive fundraising, how do I create more personal relationships with my donors to get them to act? It's about things like predicting behavior. Like, I want to figure out what my donors are most likely to do next or what they're really into, what moves the needle for them, and to be able to communicate effectively, you know, in a nuanced way against each of those, whatever their behaviors are, their interests are.
AI can be an incredibly powerful tool and help predict those kinds of behaviors and provide people with the right next steps, right? So I think, you know, that's going to be a … it's really important for us on our roadmap, like, how we're building into that reality. But I think it's going to be really powerful for nonprofits.
I think the other thing that's true about software, especially SaaS, is like, will it shift dramatically over the next five to ten years? I think, historically, the idea with SaaS is that you want software, software as a service, you want software that helps you do your job better. Right? So everybody's trying to build software that helps you do your job better. The thing that's changed, even over the last month or six months, is the expectation is now, I want software to do my work for me. It's a completely different, fundamental shift so that in, you know, I'm sure probably many people listening have heard the buzz around things like AI agents, but the idea with AI agents is, you're using AI to be able to figure out what to do next, but you're actually having the software take action and do the work for you.
Ronnie, I can stop there for a second, just, if we want to give Justin a time to get back on.
Ronnie Richard
We can keep going. He's probably trying to log back in. Obviously, we'll edit this part. But yeah, we can keep going. Do you want to pick back up? You were talking about AI agents taking the work for you.
Gabe Cooper
Yeah. So for me, a few examples of that look like, you know, I don't, I don't have time to write a personalized email to everybody on my list, but AI should know enough about the language of your organization, what really resonates with your donors, to be able to craft copy and creative in real time that's personalized for each donor, right? Like, it shouldn't be hard to get data in and out of my database. AI should be smart enough to recognize data, sort through it, shove it in and out of my database. It should be smart enough to know that this person might be a good recurring donor. I can probably automate a series of text messages and emails to them to be able to convert them to be a recurring donor without anybody having to lift a finger on my team, right? I mean, this is the world we're moving into where AI agents, AI plus automation, is beginning to do the work for you.
So yeah, it's a long, rambling way of saying, this is what gets me excited. This is what's on our roadmap. And I think it can be a game changer for fundraising.
Ronnie Richard
And the beauty of that is we all know, at nonprofits, people wear so many hats, and they have so much on their plate often, and they're being asked to do more and more, even, when you think about, keep getting more and more channels and more and more different ways to communicate with donors. And that's more and more ways to do those tasks that people have to do. So, if we can use AI and automation, these tools you're referring, to, to free up some tasks, what a game changer that is.
So, Gabe …
Gabe Cooper
When I go into fundraising teams, I think that two competing priorities are always like, hey, our donors are more distracted than ever, right? They're getting 7,000 ad messages a day. They're in doomscrolls on social media. They're getting personalized content to them. It's harder and harder to break through because people are more and more distracted. And I don't know how to break through that and connect with people personally in a way that makes sense to them, right?
And the other hand is like, I have a limited team, and I’m really strapped for time. There are 10,000 people, 100,000 people on my file, and I have, like, six people. Like, the math doesn't work for me to actually build a personal relationship, right? So you have both of those tensions pulling at the same time. And I think that's what we've been building at Virtuous for the last ten years is solving for that problem. But I do think AI combined with automation or AI agents are the next wave in how you begin solving both of those problems at scale.
Ronnie Richard
Gabe, we look forward to seeing what you and Virtuous have coming in the next few years. Before we wrap up here, I’ve just got one last question that we didn't answer earlier, and that's, what was the name of your record label?
Gabe Cooper
It's a great question. Caspian Hum Record. So, Caspian Hum, H-U-M. It's after the C. S. Lewis book “Prince Caspian.” So, it's like what Narnia looks like when everything is put right.
Ronnie Richard
Love that book. Love that book, love the “Narnia” series. All right.
Justin McCord
I think there's an insight into Gabe in that specific instance, that reference.
Gabe Cooper
That's awesome.
Ronnie Richard
All right, well thanks for joining us.
Gabe Cooper
Thank you, guys, so much. It's been a fun conversation. Bye.
Justin McCord
Thanks, Gabe.
Group: Chat is a production of RKD Group. For more information, including how you can partner with RKD to accelerate growth for your fundraising and nonprofit marketing needs, visit rkdgroup.com.
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