#39 – Jake Wood: Thrive in chaos. Team Rubicon CEO Jake Wood joins the show to discuss the story of Team Rubicon, his personal and professional development, and the release of his new book, Once A Warrior. Links to his books:

Once A Warrior https://amzn.to/39XRzAP
Take Command https://amzn.to/37RElTN

October 21, 2020 • 52:21

Aaron Spatz, Host, America’s Entrepreneur
Jake Wood, CEO. Team Rubicon

Aaron  00:05
I’m Aaron Spatz and this is The Veterans Business Podcast. A podcast centered around the stories of US military veterans and their adventures in the business world following their time in service, its stories of challenges and obstacles and an inside look at how veterans find their life’s work, their purpose in their post-military lives.

Welcome to another edition of The Veterans Business Podcast. My name is Aaron Spatz and I’m so excited that you’ve chosen to tune in today. It’s my hope that through the stories of this podcasts that you find stories of encouragement and insight to help propel you in whatever ventures that you are currently going through right now. So if you enjoy the show, please tell others about it. If you’re listening to this on an audio only platforms such as Apple or Spotify, I would be incredibly grateful for a positive review. If you really enjoy it, consider subscribing. And if you have any questions, any feedback about the show, whatsoever, feel free to email me at podcast@boldmedia.us. I sincerely enjoy getting to interact with you. And if there’s anything that jumps out, please, please, please let me know.

It is my sincere honor to introduce our guest this week, Team Rubicon’s CEO, Jake Wood. Jake served in the Marine Corps before transitioning out into a variety of different roles, including his most recent notable work, The Positivity Project, The Council on Foreign Relations, and of course, the nonprofit, Team Rubicon, where he serves as its CEO. Jake is the author of the book, Take Command, and has a new title being released shortly titled Once A Warrior. Jake, thank you so much for joining the show today.

Jake  01:42
Yeah. Thank you for having me. Looking forward to the conversation.

Aaron  01:45
Yeah, absolutely. It’s a sincere pleasure. And so just for everybody’s insight, and I know your book is probably going to cover all or if not, most of these questions. But no, I would love to get a little more insight into who you are. So what inspired you to do in the military? Take us a little bit on that journey.

Jake  02:03
Yeah, yeah, that goes way – I did not really come from a military family but I had a couple of formative experiences growing up that I think kind of subtly and not so subtly pushed me into the Marine Corps. I often look back on a moment I had when I was a young boy. My dad was working at a job in Austria, in Europe. So this is like 1989, which is a really interesting time to be in Europe. The Berlin Wall was coming down, the Soviet Union’s kind of on the verge of collapse.

And so we were living in Austria, and in one weekend, my parents took me and my sisters to a place called Mauthausen, which was a Nazi concentration camp. And that was a pretty formative event for a young, I don’t know, six or seven-year-old kid, you know, really  pretty unvarnished to look at just how evil mankind could be. And that’s a life lesson that’s immensely valuable up until that point in anybody’s life, you know, evil is like Wile E. Coyote cartoons. And so, to see just the depths to which humans could crawl was just eye-opening to me.

But I think one of the things that was most powerful about that weekend was the last exhibit that we looked at was the exhibit of the liberation of the camp when Patton’s army fought through Nazi lines and got to Mauthausen to liberate the last remaining prisoners who of course were on the verge of death. And these were people that had been starved, they were practically awaiting the gas chamber or the gallows. And that was a really powerful moment. Just seeing those men riding in on jeeps and tanks and caring so compassionately for those people that had survived to that point.

And so I’d say, I often look back at that moment and think that’s really when I started thinking about joining the military. I think any six or seven year old boy grows up like everything that they pick up becomes a gun and they play good guys and bad guys. And most young boys, I think, would have some level of that experience, but I really did think I joined – that being said, I never did. Coming out of high school, I took a different path. I went to college, didn’t go to do ROTC or anything like that. And then my freshman year in college, 9/11 happened, and I don’t want to speak to your audience about 9/11 and what it meant. I think anybody that was alive and a young adult remembered that the world changed forever that day.

And in that moment, I was really inclined to join. I thought about joining, at options to join. I think I probably went so far as to speak to a recruiter, but I was on a full scholarship to the University of Wisconsin. I was playing football. I felt like I had all these opportunities, that frankly, I just didn’t have the conviction to give up. And so I kept playing football, kept going to school. And then finally, right for my senior year, Pat Tillman died, and being a football player, that hit close to home. And I just realized that I’d done kind of a lot of talking during my time. I thought just saying I supported the troops was enough. I thought just thinking about joining the military was enough, but we all know that person. You know, that person that you meet and says, you know, learns that you were in the military and they tell you some stories about how they almost joined. And I just realized I didn’t want to be that guy. And so as soon as I graduated and played my last football game, I enlisted.

Aaron  05:49
Wow. That’s an incredible statement. And it’s definitely not the typical story, right? Guys like me probably follow more of a typical pattern, especially if you came from a service family, it’s more likely than not that. But your journey is really unique. And I think sharing the experience there in the concentration camp, and then it just kind of opening your eyes to just how depraved people are and how we can treat each other. And then I like what you said because it is so true. Everybody either almost joined or they know somebody that was in, right? That’s almost always what happens.

Jake  06:32
Right, exactly.

Aaron  06:34
And then that football connection between Pat Tillman and then you – so, I mean, do you feel like that’s what kind of made things snap for you? You’d seen 9/11, wasn’t quite enough to put you over the edge, and then you see what happened with Tillman and you’re thinking about that. And I mean, what caused you to just –?

Jake  06:55
I mean, I think when you look at what happened in the days and weeks after Tillman’s death, there was a deep exploration of who he was as a man and as an American. And I think a lot of people were talking about how he was such a man of conviction and integrity and courage. Both people that he played with, people that he went to school with, people that he then served with. And I just thought to myself, like, man, I don’t know that people would talk about me that way. And it’s not that I was a bad guy or that I was a wimp or any of those things, but I just thought to myself, like, I’ve been talking about doing this for – at this point now – 15 years of my young life. My country’s at war in two different theaters, I’m going to do it. Like now’s the time to do it. Stop making excuses. So yeah, it was definitely a turning point for me. It really forced me to look inward.

Aaron  07:49
Yeah. I mean, that’s really powerful. And then actually doing it, and then you actually shipped out and then you were well on your way. So yeah, just briefly take us with you on the journey when you were in.

Jake  08:06
Yeah. You know, the Marine Corps is unique, and yet in that, you can kind of game the system and pick where you’re going to serve. Because if you enlist west of the Mississippi, you’re probably going to go to San Diego and be a West Coast Marine. If you go east of the Mississippi, you’re probably going to go to South Carolina. And so I was at school at Wisconsin, which is east of the Mississippi. I thought, man, San Diego sounds a lot better than South Carolina. So I went back to my hometown in Iowa, enlisted out of there. I got orders to boot camp in San Diego, which was great. Of course then the Marine Corps will always get theirs. And so after graduating from School of Infantry, I got stationed at 29 Palms, California, which is like the worst duty station in all the military.

Aaron  08:48
Well done, well done.

Jake  08:48
Yeah, yeah. So I got assigned to 2nd Battalion, 7th Marine Regiment out of 29 Palms. And in 2007, we rotated into Anbar Province as part of the surge, ran counter-insurgency for seven months there. And so 2007 was the deadliest year of the war. So it was a tough time. My squad leader was wounded very quickly in that deployment. I got promoted to corporal right thereafter and kind of had to step up and fill some of that void, which was tough as you would imagine.

And then came back. I was really lucky. We lost some really good men over there. I was fortunate that I came back alive in one piece and ended up taking the INDOC for the scout sniper platoon and got selected into that and was lucky enough to get a slot to go to Marine Corps Scout Sniper school and shipped out over there, spent about ten weeks, you know, every day wondering if I had what it took to graduate. And plenty of days, I was convinced that I didn’t, but I was lucky enough to graduate.

And pretty soon thereafter, we were in Afghanistan. I was in a six-man sniper team working in an area of the Helmand Valley called the Sangin City, working really closely alongside the British troops, specifically an Irish unit. And fantastic men. I mean, really, they loved to fight. They were good, they were great soldiers. And again, was lucky to come back after a really, really tough tour. And then I just was faced with the choice that everybody’s faced with at some point, which is, you know, do I re-up and keep doing the fight or do I get out? And not to bury the lead, I chose that it was time for me to move on to something else in my life. I got out of the Marine Corps in 2009.

Aaron  10:44
Wow. Wow. Well, one, I mean, from one veteran, from one Marine to another, man, thank you so much for your service. And extremely, extremely kinetic deployments for you. And so just grateful that you made it back in one piece.

Jake  11:01
Yeah. You know, I think we all hope for kinetic deployments because we’re young and dumb. And then we kind of get punched in the face by them and we realize they’re not all they’re cracked up to be. So you know, I don’t regret it at all. I’m proud of the work that we did. It was tough. The Marines I served with dug in, fought like hell, but yeah, in retrospect, I think you’d probably stop wishing for those kinds of tours after you’ve been on a couple of them.

Aaron  11:32
Sure. Yeah, absolutely. Well, thanks for sharing a little bit of those experiences. So then you punched out then after your initial contract. And so you went to POS REP, right? You’re co-founder there?

Jake  11:50
Yeah. Not immediately. That was a couple of years after I got out. Yeah, I had an idea for a technology company that was probably a little bit before its time and certainly underfunded in execution, but the idea was to build a smartphone app that would basically be a blue force tracker for veterans and so a geo-based, location-based social network exclusively for the military community. And we launched that in 2012. And it was great. It was kind of the first of its kind. We had tens of thousands of veterans sign up and basically what would allow them to do was connect with veterans in their physical proximity. So you can do that over chat. And then if you chose to, you could just meet up in person for a beer, share experiences, whatever it might be. And you could search for people that maybe served in the same unit, had the same or similar experiences.

And so it was almost like a safety net for veterans and the inspiration was my best friend, one of my fellow Marines, my sniper partner, a guy named Clay Hunt who killed himself in 2011 in Houston, and you know, really tragic suicide. His death was also though the inspiration for a bill in Congress called the Clay Hunt SAV Act, which focused on retooling the VA for better mental health care and suicide prevention, which is great.

But at his funeral in Houston, yeah, I’m sitting there and I see all these Marines that we’d served with that show up to his funeral and we’re chatting and they all lived within 15 miles, right? And nobody knew that the other guy was there, right? So Clay didn’t know these other three Marines were there. They didn’t know each other was there. And the result was that, you know, in this moment where Clay was feeling weak, he was feeling alone, he was feeling like he didn’t have purpose. He didn’t realize that he could pick up a phone and call these Marines that knew exactly what he was going through. And the result, and it’s not the direct cause, but the result was he died. And it was just tragic to me that there wasn’t a tool to help prevent that.

And so we set out and we build it, and it was a spectacular failure. So you know, I think this is a business podcast, you know, lessons learned. We didn’t raise enough money. Our go-to-market strategy was poor. We tried to partner with the VA, which was an abysmal experience, through their innovation, the VA in the department, which is a complete misnomer. And the result was we had to shutter the doors on that company about 18 months, which is unfortunate. I’m not saying it’s going to be the next Facebook, but I think it was a good idea that had legs.

Aaron  14:50
No, I think that’s great idea, man. You’re talking about it, I’m like, man, how did I not know about this? No, because, I mean, I think that’s key. And to sit on this for just a second, because I think this is a great topic here. You know, we get out, I mean, I’ll speak to my experiences, which sounds eerily similar to so many others. But you get out and finding that community again is very difficult. And it’s there, though – that’s the thing. So when I was in, I thought that this was as good as it’s going to get. The partnerships and the friendships and everything else are never going to touch what it was like being on active duty. And then I get out and then you eventually find some people and you realize, man, it is a strong, strong network, but the challenge is kind of to your point is finding each other. And some people kind of go off the grid. Other people are a little bit more harder to track down. So going a little bit more into the weeds. So if you don’t mind, share a little bit more about the VA partnership program or whatever that program was looking like, what was that?

Jake  15:57
Yeah, I mean, so the VA Center of Innovation was a department that they established, I think, under the Obama administration. I could be wrong. And it was tasked with finding, identifying, in some cases, investing in, and acquiring technological solutions to VA problems. And that could range from advances in electronic medical records to PTSD treatments.

And I don’t want to speak too candidly about it, but we had early meetings with very, very senior leaders in VA who promised money and integrated partnerships that would have rolled out the platform – broadly speaking – across all VA constituents. And we spent a lot of money on attorneys drafting what those agreements look like and all of that, you know, tens of thousands of dollars in attorney’s fees for, again, an underfunded startup tech company. And they dragged it on for 15 months, and at the end said, “Sorry. Yeah, all those written promises we made with you, we’re not going to be able to do any of it.” And at that point, we were effectively out of the money. So you know, really nothing you can do there. I mean, tons of lessons to unpack from that as a business leader. But just an extremely unfortunate lesson, a costly lesson.

Aaron  17:31
Yeah. And I guess to kind of sum it all up, I mean, it’s kind of what we would probably expect when it comes to dealing with the federal government. It’s probably going to be a very cumbersome and lengthy process, to put it lightly.

Jake  17:46
Well, I mean, there’s a reason that the way that the industry and the government contracting industry is as consolidated as it is. It’s very hard. I mean, you can’t survive in the defense or government acquisition space unless you are SAIC, unless you’re Northrop, unless you’re Lockheed. If you’re a commercial off-the-shelf technology, getting adoption inside the DOD, the VA, you know, it’s almost impossible.

Now they’re trying to make improvements to the system so that our war fighters can get better, what’s called commercial-off-the-shelf (COTS) technology, and there’s classic examples of this. One technology partner the Team Rubicon used for many years, a company called Palantir. They actually just went public on the New York Stock Exchange, you know, $25 billion company, brilliant software platform used by intelligence analysts in addition to a bunch of other applications for big data analytics.

But you know, famously, they were kind of the software platform that was leveraged in the pursuit of Osama bin Laden, and you know, a great Silicon Valley company, take it out of the box. It’s probably an overstatement, and it works. Well, the Army couldn’t just buy Palantir. They had to go and make their own version of it because of some bullshit regulatory reason, right? And so they spent billion dollars trying to build their own, and it was totally squandered. And you had all these soldiers that are just saying, “Hey, just give us Palantir. It’s what the NSA is using, it’s what the CIA is using. But the bureaucracy doesn’t allow it.

And so it’s frustrating. Perhaps getting better. It’s been almost a decade since my experience. But if you’re going to get into the startup world, you better have a deep war chest if you want to contract in a big way with federal government or you better have a better different go-to-market strategy.

Aaron  19:51
Yeah. Well, I mean, I think, one, because this is a topic that I’ve been kind of diving into on the edges. Because the companies I lead, we have zero experience as it relates to government contract work. And it’s fascinating to me because there’s a lot of information about it out there. There’s tons of different processes to go through. And I just realized that there’s a lot of opportunity for a business. There’s a ton of opportunity. But it seems like more often than not, your best way in for a lot of these anyway – again, this is coming from a guy who does not know next to anything about the space, just to be clear – is to partner with or be a sub to a sub of a sub on a project. And that’s how you start to get a little bit of a resume going.

Jake  20:39
Yeah. I mean, your only chance for survival is to get acquired by a Northrop or an SAIC and just use their go-to-market channels to get in, and that’s perfectly fine, but just know that before you get into the game.

Aaron  20:55
Absolutely. Yeah. And then real quick about Palantir. Yeah, I saw that. I saw they went public and I had a little bit of experience with their products in Afghanistan. It was a superb product. So I’m interested to see what different ways they go in terms of what they decide to do.

Jake  21:12
Yeah, it’d be interesting. I mean, I think that they’ve had some success in commercial adoption. A lot of financial institutions like banks are using them to try to catch white-collar crime and insider trading, various fraud schemes like that. A lot of police departments are using them. So it’s still a lot of military and law enforcement applications. But you know, it’s a good product and it’s built by the smartest people in the US there in Silicon Valley. Sometimes we just got to admit that.

Aaron  21:43
Right. Yeah. As painful as that may be to some folks, but yes.

Jake  21:48
Yeah, exactly. Exactly.

Aaron  21:50
So, I mean, I guess you’ve already kind of answered my next question, which I was going to ask you to kind of take us with you on the entrepreneurial journey. Where did that start for you? And it sounded like at some point in between getting out and then going and getting things going with POS REP, you’re obviously doing some other work just to make ends meet. But was it your friend in Houston that you feel like kind of got the entrepreneurial thing going for you? Or was it something else?

Jake  22:20
Well, I mean, I think I’ve always been entrepreneurial. You know, I wasn’t exactly like Mark Zuckerberg growing up, but I tried my hand in a couple of different entrepreneurial things. It was something I always kind of aspire to. When I was getting out of the Marine Corps, being in California, I thought I wanted to go up to and try my hand in Silicon Valley. I knew that it was going to be hard to drive up to San Francisco, knock on Twitter’s headquarters’ door and say, “Hey, I’m a sniper. You should hire me.” I just didn’t feel like that was going to play well. So my first plan was to go to business school.

Aaron  22:55
Sure. Try.

Jake  22:58
Yeah, yeah. So my first plan was to go to business school and just try to, you know, one, take some time on the backside of those tours and take some time to myself and slow down a little bit, but also to polish off my analytic skills and start networking so that I actually could explore opportunities. The one thing you don’t have to develop when you’re an enlisted Marine is a strong professional network unless you’re going to be going into contracting business or law enforcement. In the officer courts, it’s a lot easier. A lot of those men and women, they are coming from strong collegiate programs and alumni networks. If they go into an academy like the Naval Academy or West Point, I mean, those are among the strongest professional networks in the world.

So I was going to go to business school. And predating POS REP, we actually started Team Rubicon. So, you know, Team Rubicon, we started that 60 days after I got out of the Marines. And so I really started cutting my teeth as an entrepreneur doing that. So much so to the point, you know, I ended up dropping out of business school after the first semester, really, to focus on it full-time. Figured I’d rather go to the school of hard knocks than UCLA’s MBA program. And then about two years after that, that’s when we tried to launch POS REP in parallel. That was kind of the second lesson: Focus on one thing. Not everybody’s Elon Musk and can build a spaceship company at the same time they’re building a car company at the same time they’re building the best solar panel company in the world. So unless you’re Elon Musk, pick one thing and focus 100% on it.

Aaron  24:38
Right. Oh, man. That’s so good. That’s so good. No, well, then, walk us in through the genesis of Team Rubicon.

Jake  24:48
Yeah. So, you know, it’s actually one of those business ideas or startup ideas that was never an idea. We – well, I shouldn’t even say we at the time it happened, it there was no we. I was sitting in my apartment in Los Angeles watching the news when the Haiti earthquake happened and hadn’t started school yet. I still had six or nine months before my MBA program was going to start. It was, again, 60 days out of the Marine Corps and kind of had that confidence streak that young Marines do. And so as I was watching the disaster and chaos unfold at Port-au-Prince, Haiti, I just thought, man, I can really go down there. I think I could help.

So I called a couple of buddies that I’d served with, guys that I played football with. And we got a team together who went down to Haiti four days after the earthquake. While we were down there, that’s when we first saw the two things that are critical to any business venture. One, kind of a need, right? So a need or a gap in the current marketplace. And two, a unique solution. So the need was that disaster response is just inadequate, right? We need a new paradigm. We need a new model for it. Lives are on the line. Disasters are increasing in frequency and cost. So this became apparent to us that there was a gap in the market.

And then, you know, we discovered while we were down there, that Marines are – not just Marines, but military veterans come back from wars in the Middle East, they’ve got great skills and experience that can be applicable in disaster zones and humanitarian crises. So we had our unique solution and then we had a choice. Is this something that we want to do? And we decided to come back from Haiti and incorporated as a nonprofit and we’ve been building and growing it ever since.

Aaron  26:43
Wow. And then take us through a little bit of the story then. I realize it’s fairly obvious, but for those that are considering some of these different options, I think it would be helpful to understand kind of how you think. So what were some of the decision, some of the factors that determine that you’re going to go nonprofit rather than for-profit?

Jake  27:04
Yeah. I mean, I think the nonprofit versus for-profit was fairly evident upfront. You know, this was a disaster response organization. It would have been really hard to run that as a for-profit, you know, not outside the realm of possibility. We could have set up as a for-profit and contracted back to different federal agencies or global multinational agencies. We could partner with insurance companies. But when other people are controlling those dollars, they also control the war. And we wanted to make sure that we always had a level of independence in where we would go and who we would help. And that meant that we really had to be somewhat untethered from that for-profit model.

So that was kind of an easy choice. I think that nonprofits, typically, it kind of a bad rep in entrepreneurial circles. People think nonprofits are like your mother’s charity, you know, like Mary Mother Sisters of the Poor, and you know, they sit outside and ring bells outside of the grocery store trying to collect some change. Yeah, that’s one version of a nonprofit organization. But in the very beginning, we said, “We’re going to be a nonprofit, but we’re going to build this like a real for-profit social enterprise. We’re going to have a great product. We’re going to sell efficiently. We’re going to deliver it well. We’re going to have amazing customer service. We’re going to innovate how we do things from a technology perspective.”

And so we often run into people who get to know our organization better and they’ll walk into our office. And the end of the day, they’ll walk out and say, “You guys are like a tech company. It’s unbelievable what you guys are doing.” And so I want people to understand that are listening, you know, there’s nothing wrong with starting a for-profit. Whatever I do next will probably be a for-profit, right? I want to try my hand at the other side of the coin, but there’s nothing wrong with starting a nonprofit. I mean, it doesn’t mean that it has to be like some stodgy, stale version of whatever your idea is. That’s just a misnomer.

Aaron  29:06
No, I think that’s great. Some other folks that I’ve had privileged to speak with in the nonprofit space kind of say the same thing, where you’ve got to treat it, run it, and view it as a regular business. It still is a business. It still has all the needs. There may be a few slightly different, unique challenges to them, but at the end of the day, you’ve got to make more than what you’re spending.

Jake  29:31
Yeah, absolutely. You got to balance a budget. And in fact, it’s actually more complicated because the customer relationships are disjointed. So when you’re running a for-profit business, in almost every circumstance, there are some exceptions, but the person who’s purchasing your product is the person who’s receiving it or servicing it. In our context, there are, you know, a hospital system has that same model. But for us, we’re taking, we’re getting money from one party and providing a service to another, which creates this triangular effect of expectations and expectations management and customer service. That’s incredibly complicated to navigate.

So, you know, I often laugh when people kind of, you know, when I’ll go to a conference and I’ll be sitting with a couple of entrepreneurs who have venture money and they’ve been on the cover of Fast Company or something and they’ll make some comment that leads me to believe that they think the Team Rubicon’s really pretty simple. “Well, it must be pretty simple to operate.” And I said, “Hey, man, we raised $50 million a year and we responded to 300 natural disasters in this year alone.” That ain’t easy to do. That’s logistics. That’s technology, That’s operational planning. That’s balancing a budget. It’s financing. It’s customer management. It’s anything but simple.

Aaron  30:52
Yeah, darn right. I mean, it’s incredibly complicated, and especially the kind of work that you’re doing is very, very complicated. You mentioned something a minute ago and I wanted to – you’ve already kind of actually addressed it, which is kind of funny because I was going to ask you what are some of the biggest misconceptions that you think people have about founding and running a nonprofit. So I feel like we already kind of hit that, but if there’s anything else that you had to add?

Jake  31:22
I mean, I would say that, yeah, I mean, that’s it. Just reimagine what you think a nonprofit is and can be and go out and build it. Don’t resign yourself to the construct of the model that other people maybe falsely hold.

Aaron  31:40
Sure. Well, then, so then you take us through some of those first years. So, you know, things kicking off in Haiti, but then take us through the growth path and that trajectory that the company was on and went do you feel like it actually was getting some steam and getting some legs and had some sustainability?

Jake  31:58
Yeah, I mean, it was brutal early on. I mean, if you’re thinking about starting a company for-profit or nonprofit, completely disarm yourself with the notion that it’s going to be like The Social Network story. I mean, it’s going to be awful. The number of times we were near bankrupt, the number of times we thought we weren’t going to make payroll, you know, you’re growing a staff, you’re making these calculated bets about investing back in the business by hiring people or adding some sort of asset, and meanwhile, you’re looking at this dwindling cash runway, wondering, “Hey, is it going to turn around?” And boy, I mean, we flirted with disaster. And that’s kind of, I guess, a pun because we’re a disaster response organization. We were flirting with disaster seemingly every year for four or five years.

But again, we were making well-informed smart bets on ourselves building a strong culture that could help navigate challenging times. But it wasn’t easy. But along the way, we continued to grow. But the thing is, you know, there’s the old adage like more people, more problems. You think you’re going to solve all these organizational problems by adding these people. But every time you add a head, your annual budget nut just goes up. It just means you have to raise more money to keep that person employed. And, oh, by the way, the complexity of an organization doesn’t grow linearly with the head count. So for every person you add, it’s not like if you go from four people to eight people, you doubled the size of head count, but you quadruple the complexity, right? You go from eight people to 16, again, you double it. But now you hundred fold the complexity. And man, it’s tough. It’s fricking tough.

Aaron  33:55
Wow. Yeah. But I think it’s important that people understand that. I mean, I feel like there is this misconception about entrepreneurship and about starting companies, that you just say, “Hey, I’d like to start a company.” And then you’d go skipping down the yellow brick road. And all of a sudden, just sunshine, unicorns and rainbows and cash is just falling out of the sky and life’s good. And it’s like, no, I’m not sure you understand exactly what you’re signing up for. And so I think it’s important for people to hear some of this.

Jake  34:25
Yeah. Let me tell you a story.

Aaron  34:28
Please, please do

Jake  34:29
There have been three periods during my time with Team Rubicon where I have been so stressed by the organization. And I would like to think that I handle stress pretty well. Been to war a couple of times, you know, frontlines. I navigate stress fairly well. There’ve been three periods of time where I’ve been so stressed, mostly for financial reasons, that I was literally grinding my teeth to the point that my molars broke in half. I’ve had to have three molars replaced because I was grinding my teeth so hard from stress.

Aaron  35:03
Dang, man. Wow.

Jake  35:05
I once joked giving a talk. I was at a conference. I was doing a panel and I said, “You’re not an entrepreneur until you’ve broken a tooth from stress. Let alone three.”

Aaron  35:17
Yeah, let alone three, right? Yeah, yeah. You’re setting the bar low by saying one.

Jake  35:24
Yeah, exactly.

Aaron  35:125
That’s awesome. So was it year four? Was it year five? Was it a major contract, a major donor? What did that look like for you? I mean, maybe never have felt that way, but has there been a point where you feel like, okay, got it, we’re on a sustainable path here? I see much more runway. We’re not having to build a train track while we’re on the train. We’ve got some runway here.

Jake  35:52
Yeah. I mean, I think that all of those moments are relative, right? So, you know, back in 2013, we would have looked back at late 2012 when Hurricane Sandy hit. And we would have thought, oh my God, that was so transformative. Well, it’ll never get better than this. And then you fast forward another, you know, we had some big moments in 2013, then we thought, oh my God, it’s never going to get better. And then, you go to 2017 with Hurricanes Harvey, Irma, Maria when the organization went from aa $15 million organization to a $35 million organization in a manner of five months. And there’s kind of a common theme throughout those moments. It was a moment of crisis, which in any moment of crisis, it’s either a threat to your organization or it’s an opportunity, right?

So crises, unless it’s entirely centered on your particular organization, generally speaking, crises are our macro events, right? If it’s happening to you, it’s happening to your other competitors. So these were moments of crisis, which, again, for anybody in any particular situations, either a threat or an opportunity, we choose to see them as opportunities. We had to be prepared in those moments to make bold decisions and then actually make them. There’s a difference between the two. Then what happens is, if you have success – and of course, success in those moments is never guaranteed. But if you have success, success begets success. So we took big bets during Hurricane Sandy because we were prepared to make them, we were courageous enough to make them. And then frankly, we had a combination of luck and determination that made those bets pay off.

But then what happens is you’re able to kind of keep those chips on the table and continue to make bigger and bigger bets. And so when the Moore, Oklahoma tornado hit six months later, now we were able to make an even bigger bet in our impact in that community. And then more and more companies joined in. And one of the things you’ll see with startup companies – particularly for like B2B companies, if you’re selling to other businesses – is that nobody wants to be the business that’s buying a service from a company and it’s their first and/or only customer, right? So you have to de-risk yourself to other companies that you’re selling to.

So for Team Rubicon, early, we kept hearing, “Yeah, your guys’ idea, it’s cute, but it’s not going to sustain. It’s not scalable.” But then we had kind of our first major company and foundation to take a bet on us. Then after Sandy, a few more big ones took bets on us, which meant that when the next one major disaster happened, these companies that we’d never heard of, we’d been de-risked for them to choose to back us because they can look at all these other customers – I’m using customers in that sense, for-profit sense – they could point to them and say, “Oh, this is this isn’t risky for me.” So, you know, all of those things factor in and what happens is your wins progressively get bigger.

Aaron  38:58
Yeah. I’d I love that visual and it’s so true. Nobody wants to be the first one. Everybody’s waiting for everybody else to make the first move. And then after that, the game on, and you got to deliver the goods, you deliver the goods, and then all of a sudden, word gets out and it’s all over the place.

Jake  39:16
Yeah, yeah. I mean, it’s kind of like having a hot hand at a blackjack table, and maybe this is a bad analogy. Somebody probably poke a hole on it. But I’m the type of blackjack player and I’m by no means an expert. But when I’m hot and I’m winning hands, if you’re smart, you’re taking chips off the table, right? Literally and figuratively. So, if I win a hand, I’ve got two $10 chips on the table, 20 bucks. Hey, dealers, can you give me 20, you know, $20 in chips? I’ll take ten, I’ll put it off to the side. I’ll stack ten. Now I’m betting 30. If I win again, hey, I get 30 bucks back and I’m stacking another ten on there. Now I’m betting 40, but I’ve already pocketed for that rainy day.

And so what happens is your wins keep getting bigger. Now, eventually you’ll lose, right? Eventually you’re going to get punched in the face. They’re going to wipe your stack away. But you’ve been smart in how you’re planning for that, but you were making bets on yourself along the way. So you have to balance taking those risks. But if you’re not willing to bet on yourself, what are you doing? You shouldn’t be in the entrepreneurial game if you’re not betting on yourself.

Aaron  40:19
Sure. So speaking of bets then, what’s one of the biggest challenges that you faced either personally or as a company? What’s one of the biggest challenges that you’ve overcome?

Jake  40:34
Well, I think we’re facing it right now with COVID-19. I mean, this is obviously an unanticipated event. Nobody really has in their full year outlook a global pandemic that holds an entire global economy to a halt. And so, for us, it’s been coupled with a couple of things. So we’ve actually moved aggressively into responding to COVID. Team Rubicon has done everything from, you know, we sent 100 medical providers into Navajo Nation and decompressed the healthcare system there and treated 3000 COVID positive patients, to we’ve been running dozens of mobile testing sites across the west. And we’ve moved almost 10,000 volunteers into food banks to help with food distribution and everything in between, right? And in the meantime, we’re responding to tornadoes and hurricanes and all this other stuff.

And you know, our funders rewarded us early for our aggressive pivot into COVID and we got millions of dollars in grants to fund it. But then the broader macroeconomic picture has not turned more upbeat and so that money hasn’t continued. We’ve depleted it. Now we’re faced with this other challenge, which is the rise – I shouldn’t say rise, but, you know, well, I guess that’s the right word, the rise of social justice as this kind of preeminent dominant issue. A lot of our corporate partners are coming to us and saying, “Hey, sorry, we’re not going to fund disaster philanthropy for the rest of the year. We’re actually going to pivot and reallocate these dollars for social justice and racial equality issue,” which, listen, I’m not going to argue like, “Hey, good, we need to solve that problem.” But at the end of the day, that’s a crisis for my budget.

So we don’t know how long this is going to persist. We’ve got to figure out ways to adapt to the new normal, both the COVID normal plus the funding priorities normal. And you know, we got a lot of chips on the table. Going back to my earlier analogy, I’ve got 200 full-time staff we’ve got to pay. Mother Nature’s not slowing down so we’ve got to continue to have operational readiness to respond to disasters. And it’s a no-fail situation. We can’t afford to fail.

Aaron  43:03
Wow. I mean, do you find that the bulk of your funding comes immediately after like a major disaster strikes? Or is it longer-term corporate relationships?

Jake  43:17
Most often, no. So most often the majority of our funding in a year is our strategic investments from long-time corporate and foundation partners. For major events, yes, we’ll see this huge upswing in funding. But for the vast majority of disasters we respond to, we actually lose money on like an individual events basis. But you know, that’s the other thing that’s happened this year. You look at the hurricanes that have been hitting the US. We have another one right now. By the way, we’re in the Greek alphabet. This has only happened a few times in history. We’re at Hurricane Delta right now. We ran out of letters. Now we’re using Greek letters.

Aaron  44:01
That’s crazy.

Jake  44:01
Hurricane Delta. It’s going to hit the US as a category four – they’re currently estimating. This is just unprecedented. Hurricane Laura, which hit probably six weeks ago, in a normal year, that would have been a $10 million fundraising event. We raised 2 million. Three weeks later, Hurricane Sally hit the kind of the Florida-Alabama line. In a normal year, that would have been probably a $3 million event for us. We raised $100,000.

Aaron  44:31

Jake  44:31
That’s how bad the economic impact of COVID that’s impacting the philanthropy for these disasters that are going to continue to happen regardless of the pandemic.

Aaron  44:41
That’s true. That is true. It doesn’t make the disasters go away, right?

Jake  44:47
No, COVID doesn’t care. I mean, Mother Nature doesn’t give a shit about COVID.

Aaron  44:52
Right. Man, yeah. And then everybody’s tracking this hurricane. And I mean, so what does that mean for you? Just give us a little bit behind the scenes of what’s happening at Team Rubicon as you’re tracking a hurricane. What does that look like?

Jake  45:08
Like I said earlier, man, it’s a no-fail mission for us. We get our leadership team together. We get our operational planners together and we have a couple of sayings that we rely on internally. One is just dig in, the other one is don’t flinch. I got that one from my coach playing at Wisconsin. He’s a hall of fame coach. He’d always tell us, “You’re going to get hit in the face. Whether it’s a blitzing linebacker, whether it’s a wide receiver cutting across the middle of the field, you’re going to get hit in the face, don’t flinch. There’s going to be a moment in a game when you’re going to get stuffed on fourth down and they’re going to block a punt, don’t flinch.” And so, you know, when you’re facing your potentially fourth or fifth landfall of a major hurricane in a single hurricane year, you’re out of money and your volunteers are exhausted, don’t flinch. Can’t afford to fail.

Aaron  46:06
Wow. That’s incredible. And then, you know, shifting gears a little bit, then. You’ve got a book coming out next month, Once A Warrior. Would love to get a little bit more an insight into that book. Give us a little bit of a preview.

Jake  46:22
Yeah. I mean, Once A Warrior is really just a memoir that talks about everything that we’ve been talking about here. It’s the story of what led me to war, what my experience was like over there. When talking about my wartime experience, you know, it’s not like a chest thumping Rambo narrative. It’s really kind of a more introspective look at a young man at war on two hard tours. It’s a story of coming back. It’s a story of losing my friend to suicide. And it’s the story of finding my way forward, my purpose in building Team Rubicon.

And the fun part about writing that story was when I got to that point about Team Rubicon, which is really the back half of the book. It was the opportunity to tell that story through the eyes – not just to me, but through the eyes of these volunteers that served for us and some of the survivors that we’ve helped. And I think the stories are powerful. And I think most importantly, you know, in a political environment that we find ourselves in here today, we don’t have to, as citizens, settle for this narrative that we all hate each other and that America is crumbling. I mean, I think we’re at risk of that, but I think there is an opportunity for us to get reinspired in the future of this country. And I think that this book goes a long way in restoring that for the people that will read it.

Aaron  47:46
That’s exciting. And so it hits shelves next month?

Jake  47:49
Yeah. November 10th, Marine Corps’ birthday.

Aaron  47:51
Awesome, man. Hey, you couldn’t have picked a better date.

Jake  47:55
Yeah, I know. Well, the publisher picked it. They had no idea. So it was fate.

Aaron  48:00
Oh, that’s cool, man. That’s cool. So how can people get in touch with you? How can people learn more about Team Rubicon? How can people get involved?

Jake  48:08
Yeah. Well, if people want to get in touch with me, they can go to my website. It’s just jakewood.co. They can learn more about the book there and they can get ahold of me through the contact form. Would love, really, for people to consider signing up, joining Team Rubicon. We’ve got 130,000 men and women across the country that have signed up, tens of thousands who are serving every year in communities after disasters but we need more. There’s more opportunities for people that need us than we could possibly meet. So if you are inclined, we’d love to have you. If you can’t necessarily hop in your car or on a plane to go to a community after disaster, consider throwing ten bucks our away online teamrubiconusa.org goes a long way.

Aaron  48:57
That’s fantastic. And Jake, I just want to thank you so much for spending some time with me. Thanks for sharing your story. And we’re cheering for you. I wish you nothing but the very best with Team Rubicon. I’m excited for your book. And once again, I just want to thank you so much for taking some time with me.

Jake  49:16
Yeah. Appreciate it. Thanks for having me on.

Aaron  49:19
Man, what a fun episode. I’m so, so grateful to Jake for just being so incredibly open and honest just with his journey. Again, it just goes back to the whole entrepreneurial journey. It is a definite game of endurance. And I love his blackjack analogy, whether or not it’s perfect or not, like he was saying it, doesn’t matter.

But there’s several things that he said that stood out to me. So, you know, viewing a crisis as either a threat or an opportunity. And I feel like that’s where a lot of winners are made. In the face of a crisis, are you going to take it and are you going to look at it as a threat or as an opportunity to your business? I mean, I think COVID-19 has been a great example of that, where we’ve seen a lot of businesses have to flex and change and pivot and go different directions. So rather than seeing it as a threat, they went ahead and made it an opportunity for the business. And now maybe this type of business is doing something else. And so that was one thing. Success begets success. I couldn’t agree any more passionately with that statement. I feel like once people have gotten a chance to know you, know your business, know what you’re all about and see that you can deliver and can do good work, then word gets out.

And to de-risk. And I think that’s another really big thing, especially for early companies. And I believe this would be a topic that would probably spark a lot of arguments. So I’m actually prepared for many of you to disagree with this and probably an equal number that would agree with this. But de-risking businesses, I think, is critical, especially in the early days. And so how do you de-risk? Maybe your money-back guarantee and maybe it’s a lower rate, lower cost, maybe lower contract terms, free shipping, free returns.

There’s any number of different mechanisms for de-risking a business to make it a little bit more attractive for the end user and makes them feel a lot more comfortable about what they’re about to do. And then there’s nothing to say that, you know, later on, as you have a track record and you have proven, like Jake shared, okay, well, now we’ve got all these organizations calling us that we’ve never heard of. We don’t have any existing relationships, but they saw how we performed for these other companies and how these other companies worked with us and what that relationship looked like. And so now we have more people coming to us. So I think it’s a great idea.

And so I’m just incredibly grateful for you sticking around, for you watching, for you listening. Thank you so much. And I look forward to seeing and hearing you and getting to hear from you. I would love a quick note from you. If there’s anything out of the show that you’d like to see, if there’s any other questions that you may have, feel free to drop me a line, again, podcast@boldmedia.us, and we’ll see you next week. See you.


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