Kyle Arteaga, Cofounder and CEO, The Bulleit Group

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Today The Storied Future Podcast welcomes Kyle Arteaga, cofounder and CEO of The Bulleit Group, an award-winning high-tech PR agency.

From an early age, Kyle believed that the science fiction of movies and television could become reality—had to become reality.

At the core of Kyle and his team’s mission is a recognition of the ways technology has shaped the present, and a determination to tell the stories of the companies that will drive the future.

In this episode, Kyle and Chris discuss how companies that are inventing the future can thrive in the midst of uncertainty and use narrative to change what happens next. They cover:

  • The influence TV shows like The Jetsons and Knight Rider had on young Kyle’s vision of what was possible
  • How comms can evolve to address the acceleration of invention, the proliferation of communication channels, and the complex desires and demands of customers, employees, and policy makers
  • How startups and enterprise tech companies can effectively tell their stories in a way that brings their vision of the future to life
  • Why having a strong narrative in times of uncertainty is critical to the future of your company
  • How to build an authentic narrative, and the importance of bringing your audience along on the journey

And much more!

011 Jake Wood: The Narrative of a Warrior

Jake Wood 00:00
We could get in a gunfight and, you know, our heart rate would never elevate above 75 beats a minute. That comes from repeated exposure to those things that are terrifying, and eventually you psychologically and spiritually and mentally can just overcome them.

Announcer 00:13
Welcome to The Storied Future Podcast with Chris Hare, a show that provides the knowledge and inspiration C-suite leaders need to shift the future. Hear from experts, innovators, and purpose-driven leaders who have harnessed the power of strategic narrative to create lasting change.

Chris Hare 00:31
Hi, and welcome to The Storied Future Podcast. I'm Chris Hare, and I'm glad you're here. Each episode I talk to C-suite leaders, experts, and innovators who have used the power of narrative to change minds, change behavior, and change the future. In today's show, The Narrative of a Warrior, I speak with Jake Wood. I've been looking forward to this for a long time, and I'm so glad Jake was game to come on the show. He's the founder and CEO of Groundswell, a software company that enables companies to make philanthropy an employee benefit. Groundswell launched in 2021, after raising 15 million in venture capital led by Google Ventures. 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. Since 2010, Team Rubicon has recruited over 150,000 volunteers and responded to nearly 1,000 disasters and humanitarian crises. Prior to Team Rubicon, Jake served for four years in an elite Marine Corps Scout Sniper unit, leading Marines in combat in Iraq and Afghanistan. He graduated at the top of this class at boot camp, the School of Infantry, and the Marine Scout Sniper course. He received three meritorious promotions with one in combat, and is the recipient of the Navy Marine Commendation Medal for Valor. Jake's memoir, Once a Warrior, was an Amazon best seller, and Tom Brokaw stated that, “It's the book America needs right now.” In this episode, we explore Jake's search for a narrative that would give his life meaning and purpose through serving others; how the story, narrative, and culture of the Marine Corps transformed Jake into a warrior; how Jake faced fear and overcame chaos on the battlefield, and how the lessons he learned can help company leaders tame chaos and face down their fears; the origin of Team Rubicon and how Jake and his team used storytelling to align donors, employees, the public, and over 150,000 volunteers around a shared mission; and finally, how he and his team at Groundswell are transforming the future by writing a new narrative that unleashes generosity to change the world. Let's dive in.

Jake, thanks for joining The Storied Future Podcast.

Jake Wood 02:47
Yeah, Chris. Thanks for having me. Excited to join here.

Chris Hare 02:49
So in April 2004, Pat Tillman of the Arizona Cardinals was killed in Afghanistan. He had enlisted in the United States Army in the aftermath of the September 11th attacks. And in your book, Once a Warrior, you write that when you saw the news on TV, it hit you hard. “I locked eyes with myself in the mirror, pulsing with shame. Pat Tillman was the man I dreamt of becoming, the type of man who answered the call, who gave without counting the cost. How had I become a young man concerned only with enriching himself? Where Pat had been selfless, I had been self-centered, Where Pat took action, I was happy to stand on the sidelines. Where he found courage, I found fear.” Jake, what path were you on prior to that moment? And what were your dreams for the future?

Jake Wood 03:37
Yeah, well, when that moment happened, I was wrapping up my junior year at the University of Wisconsin, I was playing football for the Badgers. And, you know, I think that's in part why Pat's story resonated so much with me. He was a professional football player, I was a Big 10 football player. And if you rewind the clock three years prior to that moment, 9/11 had happened, and I was a freshman on campus. And after growing up for a good part of my life thinking that I would actually join the military, I instead, you know, at the end of high school made the decision to go and take a football scholarship and go play football, not join the military. And so I think, you know, again, with Pat's story so resonant for me, I just after three years of making a bunch of excuses for why someone else should go off and fight that war in Afghanistan, I realized that, you know, the right choice, at least for me, was to get off the sidelines, I guess kind of literally and figuratively, and join my fellow countrymen doing that. It was an interesting time. But it was just one of these powerful moments of reflection that, unbeknownst to me at the time, forever kind of changed the arc and trajectory of my life.

Chris Hare 04:47
Can you rewind from that moment to when you were a kid? You talk about the fact that as a kid, you had a desire to serve, and you'd gotten good at silencing that. Can you talk a little bit about where you think that desire came from? And then what did you decide in that moment when you heard the news about Pat?

Jake Wood 05:00
Yeah, you know, I grew up, I was always pretty active in the community. You know, when I was in high school, I was, you know, in student government and responsible for things at the high school, like the student hunger drive, which was a big deal in our high school’s Athletic Conference, all the high schools competing against each other. And I kind of took point in running and managing that and kind of organized a couple of other fundraisers throughout the school year for various things. You know, I think I'd always been focused on community service, not court-ordered community service, you know, like genuine community service. And part of that, I think, was just how I was raised. I had two wonderful parents, they taught me to think about the advantages that I had in life, and to never take those things for granted. I also had some interesting experiences. When I was a young kid, my parents, we actually moved to Europe when I was a young boy. And one of the things I do write about in my book is this moment, probably the first year that we were there, where they brought my sisters and I to a former Nazi concentration camp called Mauthausen. And that was a really rude awakening for, I think I was probably seven years old at the time, for a young boy, because it was just, you know, it was just unvarnished evil. And I don't think that many young kids get exposure to that type of evil, or they get that perspective on the world that early, but it's really, I think, eye opening for me, just how bad the world could be. And one of the things I often talk about is how powerful it was to see the exhibits that focused on the liberation of the camp, which happened in 1945 by Patton's Army. And you saw these black and white photographs with these young American men who’d sailed across the ocean to go fight for people they'd never met in a country they'd never been to. And I just always found that to be so powerful. And so that was always kind of rooted in the back of my mind, this idea of being like those guys I saw in those photographs. And, you know, I was always one of those kids that would always talk to that military recruiter when they set up the table in the high school cafeteria and handout brochures. I was always over there, chatting them up. The Marines and the Army fascinated me. I went through the early stages of applying to West Point in the Naval Academy. I actually secured my nomination letter from Iowa's Senator Chuck Grassley, who's like 150 years old, and still the senator from Iowa. Twenty-five years ago, he was the senator, still is today. But then, like I said, I had this opportunity to go play football. And in 1999, when I was making that decision, or 2000, when I was making that decision, it didn't seem like it was a very consequential decision because we weren't at war. And there didn't seem to be one on the horizon. So it was really easy to say no to the military and yes to football.

Chris Hare 07:49
So in that moment, when you heard about Pat, what was the decision? And where did you go from there?

Jake Wood 07:54
Yeah, so basically, that day I decided I was going to join the military. Like I said, I was a junior, and I wanted to keep my options open as to whether I would enlist or go in as an officer. And I also felt a commitment to the team. So I made the decision then and there to join. I didn't know exactly how that would look. But I knew I wanted to graduate first before doing it. And so that summer, about a month after that, maybe two months after that, as we were closing up spring football and getting ready for the summer, I went into my coach's office, and I said, Hey, Coach, even though I have two years of eligibility left, I'm going to take only my next year, and I'm going to make it my last year on the football team. And then he looked at me. I'd had a bunch of injuries, so maybe he kind of thought it was just related to the injuries I've been having. And he said, Well, what are you going to do? I'm going to join the military. And he was like, You're out of your freakin’ mind. But that's exactly what I did. So I played my last game January 1, 2005, and immediately started training for the military. You know, I explored a bunch of different options. Do I can go in as an officer? Do I join the Army or the Marine Corps? And a bunch of different things factored into that decision, right? I ended up walking into a Marine recruiter’s office and enlisting into the infantry as a private.

Chris Hare 09:04
And do you remember that moment? So when you get off the bus at boot camp, you step onto the yellow footprints that are painted on the tarmac there. What was that feeling, if you can recall?

Jake Wood 09:13
Yeah, I mean, those yellow footprints are so legendary in the Marine Corps. You know, it's the first thing you see that night at, like, 2am when you're dragged off the bus by screaming drill instructor. And, I mean, honestly, I remember standing there on those yellow footprints thinking, Oh, my God, what did I get myself into? Because it's just a total shock and awe moment, and it's designed that way. I mean, they're trying to overwhelm you and bewilder you, and they're pretty good at it. They're pretty good at it. But as nervous as I was, as anxious as I was, I think I was also probably beaming with pride even though I probably had a terrified look on my face, because it was exactly where I wanted to be. And I knew that I was only 13 weeks away from becoming a Marine and that was the biggest goal in my life at the moment.

Chris Hare 09:59
You know, as I was listening to the audiobook of your story, it kind of hit me that the first part of your life was kind of the struggle to write your own narrative or to find a narrative. And obviously, the Marine Corps has a very strong narrative, right? They’re the storied fighting force, nearly 250-year history. What did that feel like to all of a sudden step into that and have that narrative kind of take you over? Like, you didn't have a lot of choice, right?

Jake Wood 10:21
I think the Marine Corps does a remarkable job of storytelling. You could probably say that in most of the military branches, but I think the Marine Corps is really unique in how effective they are at it. And, you know, you mentioned almost 250 years old, we just celebrated our 247th birthday.

Chris Hare 10:34
Happy Birthday, by the way.

Jake Wood 10:35
Yeah, the Marine Corps, the Marines take their birthday a little too seriously, it’s kind of a joke. But it's because there's such immense pride in the institution. Again, the Marines do a great job of making Marines feel as though they are a part of something that's bigger than themselves, that they are a thread in this tapestry of the greatest fighting force the world's ever seen. And that without you as that individual thread, the tapestry would fall apart, or that it would not continue into the future. And so, you know, I often tell people when I'm talking about organizational culture or leadership principles, I'll talk about the power of storytelling. And I'll mention that, you know, at the School of Infantry after boot camp, when instructors are teaching young marines battlefield tactics for things like how to respond to an ambush, or how to tactically withdraw from a firefight or something like that, they'll go to a whiteboard or a chalkboard, like a football coach, and they'll draw the X's and O's of the tactics. And they'll spend five minutes doing the X's and O's. And they'll spend 25 minutes telling stories of Marines that have come before you and experienced that moment, and how they responded in those moments. Because they know that, you know, when you inevitably run into that moment on the battlefield, that close ambush, or that tactical withdrawal, you're not going to remember the X's and O's, because Marines aren't that smart. But you'll remember the stories, and you'll do everything that you can to rise to make yourself a part of that story, to make your effort, your courage, a part of that Marine Corps lore, and that's a powerful motivator.

Chris Hare 12:08
I'm just hearing you say, like, there's the 5 minutes on tactics, 25 minutes on stories, but then there's just that consistent reinforcement, as you deploy, right, of just constantly hearing those stories, and constantly being trained and brought up and having those things reinforced, which I think is super powerful.

Jake Wood 12:24
Yeah, you know, again, I think every human being wants to be a part of the story. And nobody wants to be, you know, an inconsequential character in a story. They all want to be the hero of a story. And so I think it's just such a powerful tool for organizations and leaders to utilize, you know, to use storytelling to treat their team like characters in that story. And not just any character, but characters that, protagonists, people that are going to impact that narrative arc. And, you know, when you do that you unlock so much more from people. It’s just one of the things I encourage leaders to do all the time is really focus on that.

Chris Hare 12:58
And you mentioned sniper school. What was your kind of path through the Marine Corps after the School of Infantry?

Jake Wood 13:04
Yeah, so I, you know, I went through the School of Infantry. I was really fortunate. You know, maybe because I was a little bit older, maybe because I played college football, I was pretty good at it. I ended up graduating at the top of my class and getting an early promotion as a result of that. But I got sent over to a unit in Southern California in an area called Twentynine Palms. It’s probably the worst duty station in the Marine Corps, out in the high desert by Joshua Tree. And it's just really an infantry base. So there's really nothing going on other than warfighters getting ready for war and coming back from war. So you can imagine all the roughhousing that happens. But I was, you know, sent to a second battalion, seventh Marines. They'd recently rotated back from Iraq, spent maybe six months training up and were thrown right back into Iraq in 2007 as part of the surge that Congress and President Bush authorized to try to quell the insurgency that was rising. So in 2007, we went there, January, we were in a part of the Inmar province known as the Triangle of Death outside of Fallujah. And that year would become the deadliest year of the war. More coalition and enemy fighters were killed in that year than any other year. So it was tough. It was challenging. I received a promotion, a battlefield promotion, while I was over there, and came back. I was asked by a sniper that I'd met while I was over there to try out for the sniper platoon, which I was little skeptical of. I wasn't like in love with the mission set that the snipers had, but I, what I loved was the snipers that I'd met were the most mature, most professional, most committed Marines that I'd ever seen. They were highly proficient at everything that they did. And I just saw them as like, those are the types of peers that I want to have. So I tried out. I was really lucky that I passed. I'm not a very good shot, you know, in full disclosure, but most of the training, most of the Pass/Fail components of getting into a sniper platoon, it's less about shooting. It's more about maturity, judgment, the ability to learn, the ability to adapt, the ability to make, you know, good decisions under duress. And those are all things I think I'm pretty good at. Anyway, got into the platoon, you know, it's really bad, by the way, to be in a sniper platoon and not have gone to sniper school. So there's two classes of citizens in the sniper platoon. There's hogs, those are the actual snipers. And then there are pigs. And pigs are Marines that are in a sniper platoon, but that have not yet graduated from sniper school. And hogs just love hazing pigs. And so even though pigs tend to be the best Marines in the battalion, they're still treated like second class – worse than second class citizens in the sniper platoon. And so I spent about six months just getting hazed mercilessly. And then my reward was a trip to sniper school, which is the hardest school in the Marine Corps. You know, I think probably 60 to 70% of my class failed. Again, these are the best Marines from across the Marine Corps. So it's not like you have a low bar to get in. I was fortunate enough to graduate after 10 weeks. And then I was quickly sent to Afghanistan as part of a six-man sniper team tasked with tracking and hunting Taliban and insurgent forces. Pretty challenging tour, you know, limited resources, no air support, no artillery support, really kind of thrown into the thick of it. It was a bloody tour for the battalion, lost a lot of Marines. It was the bloodiest tour for any Marine Corps battalion that year. But, you know, I was fortunate I got home, all my fingers and all my toes, and made the tough decision to get out of the Marine Corps.

Chris Hare 16:23
You write that there are only two things that will keep Marines alive on the battlefield: your rifle and the Marines on your left and your right. Can you take me to a particular moment where these words really became real for you?

Jake Wood 16:34
I mean, I guess across both my tours in Iraq and Afghanistan, a lot of gun fights, you know, a lot of explosions, a lot of horrible things. I think the scariest moments for me were not the gun fights, they were the moments when they felt like they were imminent. Because when you're in a gunfight, like, after your first couple of them, you just, it's cliche, but training starts to take over. You kind of get numb to it and all that stuff. But it's the moments that precede them that I don't think ever get any less terrifying. And there were a lot of those. And you know, in Afghanistan, the horror stories I always tell, I wrote about it in a chapter in that book, were we'd run these, the area that we were in was the southern Helmand Valley. And along the Helmand River, there's a bunch of agricultural area. And typically the Taliban is there growing poppy, which supplies most of the world's opium. And so the Taliban protects that crop and harvest pretty fiercely. The State Department was trying to get the local villagers to grow corn instead of poppy, so they were paying them to grow this corn. Turns out, it was really good corn growing soil there. So this corn was just like 8, 10 feet tall. And I grew up in Iowa, so I appreciate good corn. But we'd run these missions where we'd have to navigate through these cornfields, which were thick as, you know, a jungle, and there were several nights where I was the point man on that team. So that meant, you know, I was out front kind of responsible for navigating the team through the terrain. And we'd be out there in those cornfields and all sudden, you'd hear corn stalks snap 25 meters off on your left or right, and you could kind of convince yourself that maybe you were hearing things, or maybe it was a stray dog or something. But then you'd pause, you’d hold your breath, you'd wait a couple minutes, you wouldn't hear it, so you'd start moving again. And then a couple minutes later, you'd hear it again, right? Snap – out there on the left or right. You know, in those moments, you knew that you were the one being hunted. And that was terrifying. And the only thing that I think kept allowed me to keep my nerve was when I was holding my rifle, like I said, but two, I knew I had five highly capable Marines that would do, fight tooth and nail in any circumstance to survive and win. And so even though I was the guy out there in the front as that point man walking into the boogey man's closet, seemingly, I knew I had five guys behind me that had my back. And that's a really special feeling. It's a really, as terrifying as it was, having five people behind you like that is a really special feeling.

Chris Hare 19:08
You know, one thing we explore on this show a fair amount is the role of fear and how it impacts leaders making good decisions or bad decisions. What did you carry forward from that experience? Because I hear you saying, in the moment, it's just automatic, right? You're just in there and you're fighting. But it's the in-between where it's the silence, and it's the waiting that's scary, right? How do you lead through when there's fear post-Marine Corps?

Jake Wood 19:34
Yeah, I actually I talk about this a lot. Because fear is such a powerful human emotion for so many people. It's so hard to control. And, you know, fear almost always leads people to act irrationally. And so the thing that I always encourage people to focus on is just acknowledging when they're afraid, right? Because if you're afraid, but you're not coming to grips with it, then you allow yourself to make those irrational decisions that can lead to catastrophic consequences. So the first part of that is just self-awareness, right? And understanding when you're afraid and putting your antennas up for what those irrational decisions might be, how they might manifest, how you can put controls in place to avoid making those irrational decisions. But I think more importantly is, How do you address the fear head on? How do you find courage in those moments? Or how do you, you know, eliminate fear? I mentioned, like, the gunfights got easy, right? It's not to say you never had a moment where you're like, Oh, my god, that was a close call, you know, in the thick of it, but we could get in a gunfight and our heart rate would never elevate above 75 beats a minute. That comes from repeated exposure to those things that are terrifying. And eventually you psychologically and spiritually and mentally can just overcome them. I mean, the same thing happens, you know, as an entrepreneur, there's plenty of terrifying moments. Your runway starts shrinking. You lose a big deal. You're on the verge of insolvency, whatever it might be. If you've never been there before, it's really hard to control that fear. But that's why I like seeing these folks who are repeat founders. It's really powerful. Because, you know, they're like, everything's like water off a duck's back, they've been there, done that, and they're not getting rattled. It doesn't mean that they're not concerned, it just means that they're not afraid. There's a big difference between those two things.

Chris Hare 21:20
Yeah, and I think also hearing your story, you have a very clear set of leadership principles that you adhere to, but also very strong core values, right, that then drive all of that, right?

Jake Wood 21:31
Yeah, I think you have to start there. It's the foundation of everything that you do. And not just for yourself, but for your team. You know, your team will mirror what they see in you, they'll reflect what they see in their leader. And that means that if you are unprincipled at your core, you'll have an unprincipled organization at its core. And not only that, but if you're actually influential as a leader, you can actually start corrupting the lives of the people that you're leading, which is when you really start to see tragic leadership emerge. But yeah, core values are absolutely key.

Chris Hare 22:11
Since 9/11, 3 million men and women have served in Iraq and Afghanistan. I'd love to hear first, what was your experience coming home from war? And all of a sudden, that's all gone, that community's gone, that camaraderie is gone. What was that like?

Jake Wood 22:25
Yeah, it's funny, you know, it probably leads into the next topic. But my now wife who I started dating shortly after I got back from my second tour, you know, I'd only had about six or nine months left in the Marine Corps. She likes to joke that I actually never got out of the Marines. Because so shortly after leaving the Marine Corps, I started Team Rubicon, and with Team Rubicon recreated so many of the elements of the Marine Corps had given me: that sense of team, that sense of purpose. However, it wasn't always easy. You know, I think war changes you, regardless of how successful you are on the backside. I mean, frankly, if you don't come home from war, from combat specifically, changed, like, go see a shrink, like, there's something wrong with you. I don't think that change necessarily has to be bad. It's just change. It is what it is. I'm a different person for having seen combat. I don't believe that I suffered from post traumatic stress. But I do believe that I've changed, I've suffered moral injury. I've suffered survivor's guilt. But I also think I've experienced post traumatic growth. You know, I think I'm stronger for the experiences that I've had overseas, I think I'm more resolute in my sense of purpose moving forward. And those are things that I try to channel. But I also have to give credit where credit's due. I was very lucky to have an incredible family to come home to, and with that family a safety net if I had needed it. A lot of the Marines I served with came from dysfunctional families, and they returned to dysfunctional families. And that's tragic, because they didn't have that safety net, they didn't have that psychological and emotional safety to return to. And I can't say that that always led to challenges in their transition. But frankly, you know, it often did. That's tragic.

Chris Hare 24:09
And what are some of, you know, even beyond the Marine Corps, just in the military all up, what are some of the impacts? And how did that pain that that community was experiencing, that your community is experiencing, how did that lead to the founding of Team Rubicon?

Jake Wood 24:23
Well, I don't think it led to the founding of Team Rubicon, but it eventually became a motivator for the passion that we poured into it. You know, Team Rubicon was inspired by the earthquake in Haiti in January 2010. You know, I had been out of the Marine Corps for 60 days, watched that event unfold. It was kind of like another Pat Tillman moment for me where, you know, I saw this situation happening and had to make a choice. Do I want to stay on the sidelines or do I want to jump into the action and make the tough choice and do a good thing? I'm sure we'll talk about the founding of Team Rubicon, but as we were building Team Rubicon, over the next couple of years, we started to see just how powerful of a tool it was for a lot of veterans to rekindle that sense of purpose and shared mission and sense of community brotherhood/sisterhood that they had in the military. And so we really saw that as a powerful driver, particularly as, you know, for me, my unit ended up suffering, has suffered, more suicides than we did combat deaths to include my sniper partner. And, you know, I wouldn't say that we were a cure for any of those things. But we certainly were weaving Team Rubicon’s mission, we've had such positive impact in the lives of so many military veterans and their families. And I think that was a strong, really strong driver for a lot of the effort that we poured into it.

Chris Hare 25:46
So really, the initial driver was, Hey, there's this earthquake in Haiti, we can go and serve and help. And then what were some of the things that you saw there that really inspired Team Rubicon? How was Team Rubicon birthed out of that, I guess?

Jake Wood 26:00
Yeah. So you know, watching that earthquake unfold, and having just gotten back from Iraq and Afghanistan, I felt like I had a pretty unique background experience set of skills to help. So I ended up calling around to a couple of different organizations offering assistance and, listen, this was one of the worst catastrophes of the 21st century. So these organizations that were trying to get on the ground to help were completely overwhelmed and some random idiot in Southern California calling up and gumming up the phone line saying, Hey, you really need to send me, was not very value-added for them. I can look back on the moment and come to grips with that. But not satisfied with just sending $10 to one of those organizations, I ended up calling some of the Marines I'd served with and we organized a team of veterans and doctors. We went down to Port-au-Prince, the capitol, four days after the earthquake, got on the ground, started running these mobile medical triage clinics throughout the city. And it was pretty remarkable. I mean, the thing just started snowballing. People were flying themselves down to join our effort, in the middle of the night finding us. Again, it just kept snowballing. And we began to realize that it really was just taking all that skill and experience that we gained in the military and repurposing it for this humanitarian mission. And so we came back, and we incorporated the team as a nonprofit organization as a public charity. And we set out to try to build the best disaster response organization in the world. And 12 years later, the organization scaled remarkably, we've got 150,000 volunteers across the country, we've responded to over 1100 disasters and humanitarian crises, and just really kind of an incredible unintended outcome of what seemed like a pretty simple decision in the moment, which is, Hey, I'm just gonna go down there and help. You know, never intended to build a global humanitarian organization as a result.

Chris Hare 27:55
You obviously have a lot of, you know, when you're the co-founder, and then CEO, you obviously have a ton of stakeholders, right? Between the gray shirts (your volunteers), people that you're helping your board, your donors, et cetera. How did you over time shape your narrative? And then how did you align all of those different folks to pull it off?

Jake Wood 28:13
Yeah, I mean, listen, we were first-time entrepreneurs. We didn't know anything. I’d never had a real job in my life, outside of, like, summer jobs in high school and college. So it was pretty interesting to try to will this thing into existence in the early days, because we didn't know up from down. But I think we focused early on culture. I think I was fortunate to have come out of the Marine Corps where culture was so important, you know. And not just the Marine Corps, but the Wisconsin football team, really well known for its culture. It's the only reason they compete; it’s just not that talented, but it's really a culture driven organization and it allows it to outperform. And so we focused on that. We leveraged great storytelling. It was, like, key to our early success, it was this belief that we could inspire people to join our cause by telling them incredible stories of service and impact and really invested there before almost anything else. And I think it really laid a foundation for, you know, a foundation of this narrative that people wanted to be a part of. And those people were volunteers who were joining, it was donors who wanted to support and see the idea grow and scale, it was the survivors of these storms that we were helping, or these disasters that we were helping, and they all felt like they were part of that narrative. And I think it enabled us to scale really quickly, in what is, frankly, a really challenging industry to scale in – responding to disasters. It's not easy. It's complicated. But we were able to do it.

Chris Hare 29:41
Yeah, it's complete unpredictability, right? Planning, there's constant chaos, like you talked about and just planning for the unknown and having to respond in a moment. So you had that pivotal moment when you went to Haiti. Was there a moment years on where you're like, Hey, this is, like, is there a specific memory where you just felt it, and you're like, Man, this thing is, we're not there by any stretch, right? But it's really taking hold.

Jake Wood 30:04
I mean, I think we kept shocking ourselves at the heights that we could take it to. I remember the first moment that we laid out a half million dollar annual budget, and we were like, Oh, my God, this thing might be a million-dollar-a-year organization soon. Can you even believe that? And we thought, like, we’ll have arrived when we hit that, you know. And you fast forward nine years, and it's a $55 million a year budget. We just think, Oh, my God, we never could have imagined that I think, you know, today, we're probably fooling ourselves into thinking that we're nearing the ceiling of impact that we can generate. But I bet you, if we fast forward a decade, it'll be a quarter million dollars. Sorry, a quarter billion dollars 250 million. And so there were always these moments throughout these events that happened, disaster events, which are tragic, but also provided us moments in time where this tremendous need intersected with this tremendous opportunity to take a leap forward and scale our impact. And in those moments, I mean, sometimes you don't realize those moments for what they are. But we always bet on ourselves. In those moments, we took risk, which is inherent in being a disaster response organization, but I'm talking about like real organizational risk, like put the future of the organization on the line, to meet those moments. And they almost always resulted in 2x, 3x, 10x growth. Because as the cliche goes, luck is when preparation meets opportunity. These moments were opportunities, and we've been preparing for them the entire organization's existence, and we had the courage to bet on ourselves in them.

Chris Hare 31:40
And what role did technology play? I know you guys were kind of born in the cloud, live in the cloud. What role has technology really played for you all?

Jake Wood 31:49
I mean, when you think about what we did, we basically built a nationwide organization overnight, right? We had these, initially, hundreds of volunteers in all 50 states, we had to find a way to stitch it all together, get them on the same operating picture. And we didn't have the luxury of having a template. It was almost as if we built a nationwide franchise model without ever having built the first franchise, right? And so truly building the plane as we were flying it. And one of the key pillars of being able to do that was to lean into technology aggressively. And I often say, and you kind of mentioned that we were born in the cloud, one of the advantages we had was we didn't have any legacy systems that we had to get rid of. We could build from scratch. And it just so happened that our founding coincided with this incredible cloud-based computing revolution. And so many of these Software as a Service platforms were emerging that allowed us to implement solutions relatively cheaply, relatively quickly. Of course, we found ourselves five years later with this Frankenstein of a tech ecosystem that we then had to burn to the ground and start over. But that's fine. You know, we had the strength of conviction to do that, to make those like hard choices five years in and redesign everything. And we were able to go to companies like Microsoft and tell an incredible story of our vision for what a tech-enabled disaster response organization would look like. And again, and we've talked about storytelling a lot, but Microsoft walked away from that first meeting, and they bought in, and they bought in in a big way. And the result has been an incredible partnership that's lasted five or six years and resulted in incredible platforms that we've collaborated on, built together, and then have made open source to other organizations out there that are mobilizing tens of thousands of volunteers. So really lifted the entire space up through our vision for how technology could improve outcomes.

Chris Hare 33:50
I know last year, you transitioned out of being CEO. What did that handoff look like for you? And what were some of the most important lessons from handing over the reins and handing over that narrative?

Jake Wood 34:00
Yeah, I had always known that I was not going to lead Team Rubicon forever, both because I wanted to start other companies, I knew I there were other things I wanted to do in my career. I'm also a big believer that organizations should have leadership changes. I think it's healthy for organizations to do that. And so that had been the plan for a long time. Frankly, I'm amazed that I ran it for 11 years, you know, that I didn't get run out of town or I didn't get bored earlier. But about five years prior, I brought in a new Chief Operating Officer that I eventually promoted into president. His name's Art delaCruz. He’s just one of those guys where I was constantly amazed that he joined to be my number two, just one of these immensely talented guys, and not just talented, but accomplished. And you know, we brought him in with the intent of him being the succession plan, and neither of us, I don't think, that is gonna take five years for us to enact it, but lo and behold, we loved working together and I kept finding myself challenged and motivated. But the time finally came. I knew as we were in the midst of COVID, that everything would change on the back end of COVID. And it just seemed like the right time to then have the organization's next leader lead Team Rubicon into that change. So we enacted that plan, we were slow and deliberate with how it looked. But again, we're just really fortunate that we had him waiting in the wings. And it felt great. Honestly, it felt great. It's an exhausting job to run a disaster response organization, responding to terrible things, 24 hours a day, seven days a week. And it was just such, I mean, it was simultaneously the greatest job I think I'll ever have, but also the most draining, so I needed to step away. But I also think it was what's best for the organization, and Art has certainly proved that as they're having a bumper year this year, and things are doing great.

Chris Hare 35:53
That's awesome. So I'm guessing someone like you, you had a ton of ideas of what you wanted to do after you left. Talk to me about Groundswell and how you honed in on that idea and where that inspiration came from?

Jake Wood 36:04
Yeah, so one of the things that was funny, as soon as I told myself that I was leaving, that it was time, I immediately had a couple of ideas, and one of them was Groundswell. And really, the idea for Groundswell was, I guess, one of the things I had observed running Team Rubicon was just how inefficient philanthropy can be, and really through two different lenses. One was, it always drove me nuts that normal people who give away, often, a greater percentage of their wealth or income, didn't have access to the same giving tools the rich people had. And that drove me nuts, because I didn't feel like that had to be the case. The second thing is Team Rubicon raised a lot of money from companies. And one of the things I observed was companies think they're really good at giving away money, and they're actually really bad at it. And I just felt like there was an opportunity to help them solve that. So kind of a meandering way of saying, we came to this idea for Groundswell with this vision of democratizing philanthropy. And what that meant for us was, How do we build the world's most modern giving platform and unlock, for normal people, the same giving tools that rich people have access to? And then how do we package that as a corporate benefit that we can sell to companies, whereby they decentralize their corporate philanthropy? And instead of having the CEO make the decision about what they're supporting and why, empower their employees to support the things that matter most to them, as individuals, as diverse human beings with diverse perspectives on their community. And, you know, the result’s been Groundswell. We're really excited about the progress we're having. It's been exciting to see the reception it's been getting from companies, this idea of challenging them to democratize their corporate giving. You know, I think it's coming at a time when companies are scrambling to differentiate their benefits, to align their values with employees, to focus on social impact and issues like DEI. So I think there's a lot of tailwinds that we've been able to capture in our sails, and we're excited about the future.

Chris Hare 38:06
And what are, like, if you can take me inside, deeper into some of the employee mindset, and what are they looking for? And how can you all help them get there?

Jake Wood 38:15
Yeah, well, for the employees, I think that there has been a shift that's been happening in the labor market, right? So first, millennial and Gen Z workers are the largest share of the workforce now. And it's really well documented that they are searching for more than just a paycheck. They're looking to generate purpose alongside profit, social impact alongside profit, and they're no longer satisfied with the old maximizing shareholder value. And so I think if companies want to consistently win in that talent war for young talent, they're gonna have to find a way to prove that they are invested in social impact. Second, obviously, there's this focus now on diversity, equity, and inclusion. I think that it's received a lot of lip service from companies. Some companies are doing things that are really meaningful along those lines, and other companies are struggling to figure out how to make actionable their efforts in DEI. And one of the things that Groundswell does – because again, it's empowering employees to execute that corporate philanthropy, it's providing funds, charitable funds, to them directly to give away – it's really an acknowledgement that the issues facing our community are diverse. People are going to have diverse perspectives on what the most important issues are based off of their lived experiences. And, you know, the CEO who probably looks like me, white guy, probably a little bit older than me, great education, life of privilege, all that stuff, maybe his perspective on the issues that are most pressing in the community don't reflect the issues that his employees feel. So I think that's really powerful there. As well, the shift to remote/hybrid work. You're looking at people who aren’t even living in the same community as their corporate headquarters. So how do you empower them? And then lastly, there's just this new normal where there's an expectation from all of the company’s stakeholders, not just employees, but customers, investors, that those companies speak or act on the social issues that continue to arise. And it ranges from things like George Floyd to antisemitism and Kanye West to Roe v. Wade and the war in Ukraine. And for each of these things, there's someone in your company who sees this as the most important issue in their life. And they email HR, they email the CEO, and they say, What are we going to do about this? And listen, it's not unwarranted that they expect some action, but it's also unsustainable for the company to act on all of them. And so how do you have your cake and eat it, too? Well, we see it as really empowering your people to take that action on their own behalf.

Chris Hare 40:48
So what is the flow, like my experience as an employee within Groundswell, look like when I see something and I want to give right away, what happens?

Jake Wood 40:57
So, what our platform does is it basically makes philanthropy an employee benefit. And what that looks like for an employee is it's almost like an HSA or a 401k, but for charity. So your company signs up for the platform, they invite you into their Groundswell program, you download an app on your phone, you create an account, and basically you have your own Donor Advised Fund, which is a tax advantaged charitable vehicle that, going back to what I said earlier, has traditionally only been available to high net worth people. So now you have this great giving tool, it kind of looks and feels like a Venmo account on your phone. And you participate by setting aside charitable dollars to give away and your company can participate by either directly giving you money to give away, just gifting you funds, or matching the funds that you put in, again, like a 401k or an HSA. And then you give them to charity, through a native mobile experience that is kind of like the Robin Hood for giving. You know, a rich, immersive experience that helps you discover causes based off what you care about, based off what you see happening in the news, and investing in those causes confidently, providing much needed funds to organizations on the front lines, creating impact in the community.

Chris Hare 42:12
And as you've put the story together, what's been the hardest part about it, or the most challenging part, or what's been helpful for you in really putting that narrative together that really resonates?

Jake Wood 42:21
I think it's really just understanding our audiences. So I think we have the right talking points, I think we have the right value propositions, it's understanding, What are the specific pain points for each different customer audience that we're talking to that we can solve? So for some companies, we lean more aggressively into employee privacy, with others, it's DEI, still others, it's treating this as a component of compensation. I think that they're all really valid, and they all resonate with someone. It's how do we, early in conversations or in discovery, really figure out, Okay, which one is this person? Who is this person? And what do we lead with here? And we're getting there, you know, we've only been selling for five months. We've got a young, new sales team. So I think, you know, within the next couple of quarters, we're gonna have like a really good rhythm and a much better understanding.

Chris Hare 43:16
And I guess, in this current moment, what's been the hardest thing about selling it in, you know, when folks are laying off people left and right, big companies laying off folks, cutting spend, etc? What's the most challenging part for you all in selling into that space?

Jake Wood 43:32
Yeah, I mean, I think it's obvious, right? You have to convince people this is an area worth investing in. So, you know, in an era when people are trying to cut costs, doesn't mean they're cutting costs across the board, right? They're cutting costs that they see as extraneous, and they're reinvesting some of those savings into other areas that they think are going to accelerate growth. So one of the things that we believe is that as companies are maybe even going through layoffs, the employees that remain, they have a real interest in keeping them. Otherwise they would have laid them off, right? So, if you go and you reduce your workforce by 25%, how are you motivating and inspiring the remaining 75% to remain loyal and motivated to show up to work every day? And there’s a great anecdote. There's a technology company that I won't name but pretty well-known tech company, series D, valued over $4 billion, that we've been talking to for about nine months. And they've been indicating interest, they thought there was more of a 2023 benefit for them. And so that's kind of why the conversations were going a bit slow, that they were working it into their budget. And then all of a sudden, it came out in the news that they just laid off 40% of their workforce. And we thought, internally, we're like, Alright, well, that deal’s dead. But interestingly, about two or three weeks after that news broke, they reached back out and they said, Alright, we're ready to sign up Groundswell. And the motivation was that they thought it was a critical piece to building a culture in the aftermath that those really tough layoffs that would be material in retaining the remaining employees. So I think that there's that opportunity there. Is it easy? No, it's not easy. You got to convince people of that. And as a young company, we don't have a ton of data. It's really just trying to craft strong arguments that are not yet backed up by data. And that's never easy.

Chris Hare 45:15
I remember way back in the day, I worked for trillion-dollar company that's not Microsoft, but I won't name them. And I remember calling the Employee Resource Center and I said, What's the employee match program here for giving? And it was just dead silent on the other end. And they came back and they said, What's that? And I said, Yeah, that's the problem, right? But then saw the opposite. Like, when I went to Microsoft, it's like, Hey, how can we match a lot of your time and your money and all of that and help you give, right?

Jake Wood 45:43
Microsoft is an incredible company. They've got the strongest, largest employee giving program in the world. And it's not by accident, it’s by design. It's because they prioritize it and they see it as an important part of their culture. And, you know, I've been up there on that campus, I think it's every October, when they face every manager, like, Hey, the manager’s manager is expecting 100% participation on each of those teams. That manager is out there emailing, calling, checking in with employees, Hey, why aren’t you participating yet? Why aren't you participating yet? And it's pretty special.

Chris Hare 46:16
But to your point, that first company has actually since discovered, like, Hey, we've got to retain our people, right? And we need to build that culture and allow workers to do that, right?

Jake Wood 46:23
Oh, I know. Because I just participated in that company's RFP. Yeah.

Chris Hare 46:29
Man, tons of chaos at the moment. You thrive in chaos, your whole career has been in chaos. What's the mindset that helps you navigate this, and what do you share with other leaders that can kind of help them as they lead companies through all the uncertainty?

Jake Wood 46:44
I think that there's a few things, and we probably don't have enough time to get through all of it. But first, I think organizations are set up to win or lose in chaos before the chaos happens, right? And if you don't have a foundation established before that moment that is rooted in a clear vision, a strong culture, a high degree of alignment across the team in what you're all trying to accomplish, what your objectives are, you're just going to flounder. Culture probably being the most important element of that. I define culture as the thing that guides decisions in the absence of orders. And when you think about moments of chaos, it requires people to be empowered. And it requires companies to work with institutional agility, to move with speed. And you can't do that if you don't have a culture that's helping guide them in their decisions, actions, behaviors, without being told what to do. You know, and if you can do that, man, you can unleash a ton of potential in the midst of chaos. And frankly, I think the best organizations always emerge stronger. But you have to be ready for them.

Chris Hare 47:51
I love that. You know, Jake, as we come to a close here, I'd love to end on a personal note. We haven't touched on what I see and hear is kind of the most important part of your identity, which is husband and father. How have those relationships and those responsibilities transformed you as a human and as a leader?

Jake Wood 48:10
Yeah, it's funny, I saw someone earlier this year post something online. It’s a guy that I’ve followed for a long time, I've got a lot of respect for him, though I don't know him personally. And he wrote, “Fatherhood is the only thing in life that actually lived up to the hype.” And I think about some of the things I've been able to do in my life – play college football, go in the military, serve in combat, start a company, be successful starting a company. There's a lot of hype around all of those things. I think people imagine what it feels like to do them and like, yeah, they were all cool. They were all fun. Like, we’d do them all again. Fatherhood is the only one that is hyped up, like everybody talks about how amazing it is to become a father, to have a child. It’s the only thing that actually truly lived up to the hype. So that's been amazing. And I think it made, you know, I think I've had some success in my life. But I've had a lot of tragedy. There's a lot of things have gone wrong over the last two decades. And a lot of that was at war. But having kids made it all worth it for sure. And, you know, when I seek inspiration for the future, and the effort that I need to put into the work that I'm doing, again, cliches, but they're cliches for a reason. Trying to leave the world a better place for my kids is chief among them, at a time when I think a lot of people are worried about what the future holds for generations to come. So yeah, I mean, it's been amazing and grounding and inspiring all at the same time.

Chris Hare 49:44
Well, thanks, Jake. This has been awesome. I really appreciate your time.

Jake Wood 49:47
Yeah, thanks for having me on. I hope to be back some time.

Chris Hare 49:50
Jake is an incredible storyteller. And when you string together those moments from across his life, you can see how those stories have shaped his personal narrative. You can also see how that narrative has shifted over time, and how he has taken control of that narrative to transform himself, transform his community, and transform our world, all in pursuit of a better future. Jake writes about this in his book, Once a Warrior, in a chapter called ‘Moments and Decisions’: “My decision to enlist wasn't spontaneous. Nor was it a complete surprise to those who loved me. It was the culmination of a series of moments in my life, beginning when I was seven years old and first discovered the true meaning of evil and the definition of hero. Oftentimes, we don't recognize these moments for what they are when they happen, but they shape us. They define us without our knowing. And sometimes we wake up and realize we are trapped in a version of our life that our moments didn't intend for us. Only then can we look back and appreciate those moments for what they were: the universe showing us our life's book and affording us the opportunity to read how the story should end.” And that's it. Thanks for joining us. Next week is our final episode of Season 1 of The Storied Future Podcast, where I'll be talking with Erica Brinker. Erica is the Chief Commercial Officer and head of ESG at Array Technologies, and you're in for a real treat. Until then, thanks for joining me. Please subscribe, leave us a review, and be sure to visit TSFpod.com for more information about Jake Wood and about Groundswell, as well as Show Notes and to check out other episodes.

The Storied Future Podcast is a production of The Storied Future, LLC, produced and edited by Ray Sylvester, audio engineering by Ali Özbay, logo design by Evan MacDonald, theme music by The Brewz. Your host is me, Chris Hare. Learn more about our work helping leaders create great B2B narratives for a change at www.thestoriedfold.wpengine.com.


Kyle’s LinkedIn

Kyle is cofounder and CEO of The Bulleit Group, an award-winning high-tech PR firm that’s working to bring sci-fi to life.

Their 50-person team in San Francisco, Nashville, Washington D.C., and New York consists of anthropologists, data scientists, physicists, politicos, and journalists all turned master storytellers. They get fired up when uncurbed experimentation leads to reinvention.

Kyle was previously Vice President of Corporate Development and Communications at Siemens, VP of Corporate Communications at Serena Software, Global Head of Marketing and Communications at Reuters, and Public Relations Manager at Netscape Communications. He has a B.A. in cultural anthropology from the University of Arizona.