Transition Interview Series: Part 1 with Judson Kauffman

A conversation with former SEAL and entrepreneur Jud Kauffman about what it takes to find purpose, and why your military service isn't an identity.

            Earlier this year, I found myself looking for some counsel with respect to a few organizational changes we were considering within the Veterans’ Outdoor Advocacy Group (VOAG). Someone recommended I reach out to Judson Kaufman, former SEAL and founder of multiple successful businesses in the last decade. Oddly, I knew of Jud. We met in 2009 at the Brentwood TN YMCA, when I partook, and he administered the physical readiness tests required to join the Navy.

            After some back and forth, I met up with Jud for lunch in Austin, where he now lives. We connected the dots back to 2009 and he told me about his experience as an entrepreneur, and his inability to find satisfaction post-service until a transformation took place that was centered around self-awareness. Seemingly, we had a great deal in common. We’d served on the same SEAL team during different decades, both had young families, and at least at one point or another struggled to define what our post-service identity was going to be. 

            Initially, I held back the admission that his experience felt partly like a challenge and partly as if it were a cautionary tale in my own search for post-service satisfaction. However, it eventually became obvious as I realized the many commonalities between Jud’s current focus as a speaker and coach, and my attempts to develop this publication into a collection of thoughts that assist the military transition process.

Through this series of profiles, my goal is to establish that separation from the military is far more than simply a vocational transfer, to highlight its complexity and to show how the process unfolds over a longer period of time than one might expect. I found getting to know Jud, and our conversation below demonstrates all of the above. Fortunately, he agreed to recount some of the key inflection points we’d talked about, that got him where he is today.

When we met in Nashville in 09’, you’d moved there following two Iraq deployments, do I have that right?

Right. I deployed with the intelligence community as well, before the teams, and some time as a rescue swimmer. But yes, two deployments to Iraq and then got out and moved to Nashville working for the Navy as a civilian.

Got it, and you were getting an MBA is that right?

No, at that time I was getting my undergrad from Belmont University. Sort of an unhealthy period looking back, if I wasn’t working, I was partying, working out some.

Somewhere around there I met this guy, still working for the Navy. He was an entrepreneur and asked me to come work for him. It was a consumer product company. I was VP of product development, working my ass off drinking and partying a lot at that time. One day I get this call from a buddy in the teams, Brian Bourgeois, I’ll never forget, I get a call from this SEAL, still in the teams, and I’m taking a bubble bath. He thought that was hilarious.

This is Brian Bourgeois who passed away last year?

Yeah, that’s right. He wants to know what it’s like getting out. “It’s fucking hard” I told him. I guess this was 2012. I said, “Nobody understands what kind of experience guys like us have had, so nobody assigns any value to it.”

Everyone I was talking to at that time wanted to hire me at an entry level. No one had really demonstrated the skill transfer back then. Wasn’t like it is now.

“That’s a real problem” Brian said, “Someone should do something about that.” So from there I was inspired to start this company called Exbellum. It was going to be like a secure LinkedIn for SpecOps guys. It did well, it worked I suppose but it was hard to monetize. Nobody really wanted to pay much money for that service. We ended up looking a lot like a recruitment firm that also provided management consulting services, and I ran that for a handful of years.

Are you in Austin by this point?

Yes, so after four or five years of that I wanted to use my GI Bill, so I moved to Austin. I just chose a Master’s in business because I didn’t know what else to do. Everyone else was getting MBA’s so I thought, I’ll just do that. While I was there, that’s when I started Desert Door Distillery and eventually TerraDepth.

Wow so by this point you’ve got a master’s degree and you’re running two companies?  That’s a lot of hats. You’re married at this time?

Correct. I had gotten married, I had kids at this point.

So eventually at this time, I started feeling like I had done all the things that I was told I had to do in order to be happy. Growing up I was told to pursue these specific things and those specific things, if achieved will equate to happiness.

In reality, I had a hard time finding joy in anything, and I really didn’t know who I was. A lot of it was feeling empty really, pissed off all the time, this was around 2017. Eventually it got so bad that the thought of ending my own life had entered the picture. I had kids, so I ruled it out for them, but every day for a matter of months and maybe even a year, suicide was in out of my head.

Finally, I end up having this real shitty night, and the next morning I decide, if I’m not going to end my life, then I have to change it. I really didn’t have any respect for myself, I didn’t love myself, I didn’t know what the fuck I was doing, nothing gave me joy. On paper, I had every reason to be happy, former team guy, CEO, I had made a couple bucks by this point, but inside I was empty.

Were you thinking about combat a lot at this time? How much do you think your experience in Iraq was having an impact on what you were going through?

I thought there might be some combat related stuff. At one point I went and got a therapist at the VA and talked about some combat stuff and it wasn’t really helpful, but it did get the ball moving in the right direction, I guess.

I decided to buy some books on psychology and neuroscience and was spending a lot of time trying to identify what was wrong with me. Nothing really came of it except it did lead to a practice of meditation which really was the first thing that felt like it was moving the needle.

I started feeling a little better, still reading a ton of books. Books on psychology, philosophy, all kinds of stuff that wasn’t relative to my professional life, but looking for something that would explain what was going on in my personal life.

Then slowly I started spending time out in nature some, started doing things I enjoyed that I hadn’t done in years.

I was still working super hard. I was an executive you know? Just going hard, juggling a ton of things, and never making time for solitude, never making time for relationships. So, I started to think about all this type of stuff and started feeling a little better.

Eventually I get a call one day from a SEAL buddy who was very successful. He tells me he’s going to commit suicide. The same day, or maybe the day before, I had just read this article about psychedelic therapy, which was totally off the radar at this time, it’s still 2017. So I said, “look if you’re going to end your life, at least go try this first.” So he did and it completely transformed his life. So his experience was enough to convince me to give it a try. So eventually I did, I went to Mexico, and I do this multi-day immersive psychedelic retreat.

That experience was like stepping onto a bullet train. I felt like I had taken a few steps forward on my own with meditation and some outdoor therapy work, but this experience multiplied my progress tenfold.

Previous to this, I had been an atheist for a long, long time, but when I came back from that experience with psychedelics, I started thinking more about the whole idea of it all, not really in a Christian sense, but engaging in the idea of spirituality although somewhat defiantly at first. I bought all these books on physics and pharmacology, and I really wanted to understand what had happened. I probably read 2-300 books on these topics, still trying to rationalize and find answers to everything I was going through and what the psychedelic experience had done.

That’s incredible. So, was this before programs like VETS and Mission Within?

Right at the beginning, the whole idea of it was just getting its legs at this time, still very fringe.

Do you feel like you found the answer?

Well, what I realized is, what I felt leaving the military had very little to do with my combat trauma and a lot to do with identity. I experienced an identity crisis when I left the military. When you serve in the military, especially a unit like the SEAL teams or any really, your identity is defined for you, it’s very clear, and you go all in on that identity. The whole experience of being in the military has a very effective way of creating a world where you define yourself by the environment they create for you, which is outside of you. This is encouraged and is largely the definition of what it means to serve selflessly, or place “service before self.” The SEAL teams, or the ethos of being a SEAL doesn’t exist inside of a human being, it’s externally constructed and that’s what we identify with. You have to. You have to if you’re going to trust the next guy to jump on a grenade or run across gunfire to pick your ass up. You as well as the other guys around you have to go all in on this identity to be successful in that community.

The problem is this sets us up for a massive breakdown when we decide to leave. When you leave that community your sense of identity stays there, you move on. A void opens. The size of that void, I now know, is going to be determined by how you define yourself. You and I defined ourselves by the external environment of Navy SEAL, and that can cause problems, and it certainly did for me.

That makes a ton of sense to me. Certainly, something that I’ve experienced now that I’m hearing you talk through it. How do you think we “re-define” ourselves per se, especially when you see guys do 25 years, the last time they didn’t identify as a military member was when they were 18 years old?

What was required for me to heal, and I think what’s required for anyone to heal in this situation, is self-awareness, a very intimate level of self-awareness. This takes more courage than anything you can do in your life. I thought I had courage when I was a SEAL because I would run through gunfire if I had to, that’s bravery. Bravery is mostly external, and courage is mostly internal. Courage is looking inside yourself and admitting what’s in there and choosing to embrace it. Moreover, sharing that with the world. I’d say most of us are afraid to do that.

So anyway, I start this journey of self-awareness and that led to me discovering a new sense of purpose. What happened when I was this CEO executive business guy, was my sense of purpose disappeared, it was still with the SEAL teams, it was the mission of the U.S. military, it wasn’t attached to me as an individual.

What I learned, and what I believe is that we all have this authentic self, what makes us different from every other human on earth. I think it’s primarily shaped when we’re children and then eventually the ego tells us to cover it up or to avoid being ostracized or made fun of or whatever. Most people do cover it up, but some people don’t. Those people seem like they become the best artists, entrepreneurs, the best whatever. Those people seem to be highly admired because they show up as themselves and they’re vulnerable to the point of being likeable.

That’s really inspiring and eye opening if I’m being honest. I’d like to believe I’ve had those conversations with myself but I’m not sure I really have.

Well, it’s terrifying. That’s why most people won’t do it. Most people get to their forties and fifties and that’s when that voice starts to ask “life, or at least our professional life is more than halfway over here, is this job I have really what I wanted my life’s work to be?”

The scariest thing I’ve ever done was that period when I resigned from TerraDepth. I had a secure income, I had status, and everything inside of me was telling me I need to quit. I was caught between these two messages, one message was my intellect saying, “this is smart, stay on this path, this is eventually going to make sense and lead to everything you want” and then my heart saying, “no this isn’t you; you’re living someone else’s dream, this is not what brings out the best of Jud.”

How do you look at balancing your responsibility as a father and husband and the necessity to provide for them with this simultaneous obligation you feel to be true to yourself? What if you come to the realization that whatever your purpose is, whatever your authentic self is, doesn’t align to a role that generates money?

I’d be extremely surprised if someone were to go through this process and it’s not obvious how to make money. It took me some time but eventually it becomes clear. When we understand and are working in what we consider to be our purpose, suddenly all the things we used to associate with work, changes. We feel like we’re where we’re meant to be.

When I think about being a father and my obligation to my family, there’s a lot there. There’s a lot of obligations, however one of them is being present and being the best version of myself so that they can experience me when I’m not angry, frustrated and distracted. When I was working 50 or 60 hours a week, there wasn’t a lot left of me for my kids or my wife. So what was their experience?  It’s Dad works a lot, sometimes he takes me to the park or does art projects with me but I don’t really have a deep relationship with him, and that’s okay, he works hard and I appreciate the life he’s given us. That’s how it was with my dad.

That’s not the relationship I want with my kids. I want to connect with them on a deep level, understand them, and teach them how to figure some of this stuff out faster than I did.

When I left TerraDepth, my wife was very scared, obviously. We had a mortgage, car payments, all that. I had to tell her “I’m not going to let us get into some situation where our family is deep in debt, or in trouble. But you need to understand, the message I’m getting, the feeling that I have is that I have to take this step and that if I jump, the net will appear.” For me when I invested in this journey, like I suspected the clarity came.

That’s a beautiful story. Other than sharing what you went through, how do you encourage other Vets’, or anyone really start to engage in this process?

It’s a process you know. I never thought about any of this stuff until I started exposing myself to some of these scary experiences, conversations, meditation etc. From there I started to feel like a more sincere person, something I never got in my work professionally. So my initial thought was like, okay, I have to quit TerraDepth. The way I responded to that was, “that’s terrifying”, and I just put my nose back to the grindstone, quit meditating, quit praying, quit all that stuff. After a few months, running and gunning I would start to feel a little more depressed, drinking more alcohol, and feeling like I’m not the guy I want to be, and then I would start again, back to meditating and what have you. The voice would come back telling me to quit. I went through that cycle four or five times. Eventually I did it, I told my partner, co-founder, one of my very best friends, I’ve got to go, and I left.

I’m thinking about having this conversation with a separating military member and how they might respond. What advice do you have for someone transitioning this year? Obviously, it’s a lived experience but what advice would you offer that person to set themselves up for success?

Yeah, I would say the most important thing you can do in order to have a life that ends on the highest possible note is to invest in self-awareness. Really get down to the brass tacks on who you are as a human being without any connectivity to the external world. You’re not a Navy SEAL or whatever job this person is coming from, that’s a job that you did. That’s not who you are. Until you can tell me who you are, and not bring up any job that you’ve ever done, you don’t know who you are. Don’t go and take a high paying job, because it’s a high paying job, because I guarantee you at a certain point, you’re going to start asking some really hard questions that you could be asking yourself now.

…

            As the hour concluded I made it a point to thank Jud for sharing this story, given the obvious that all of this must feel deeply personal. “I want this message out there” he told me. “I think it’s the most important message, or at least the most important message I can tell. It’s my mission, it’s what I’m coaching and speaking on.”

Listening to Jud’s journey from active duty to where he is today, deeply resonated with me and my hope is that the same is true for readers of The Transition. Today, Jud dedicates himself to helping others find fulfillment and purpose through self-awareness. You can learn more about the multitude of projects he’s engaged in at www.judsonkauffman.com, on LinkedIn and on Instagram at @judson_kauffman.