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Client Horror Stories

Transcription of Mark Jacobsen’s episode (That time you poured your heart into your moonshot, but ended up burning down 3 acres of Stanford University)

Transcription of Mark Jacobsen’s episode (That time you poured your heart into your moonshot, but ended up burning down 3 acres of Stanford University)

This transcription belongs to Episode #20: Our Beloved Host, Morgan Friedman, meets the US Air Force leader and strategist Mark Jacobsen. Please watch the complete episode here!


Morgan (Host):  Hey everyone, welcome to the latest edition of client-horror stories. Tonight, I’m excited to have a special episode different than all previous ones because this one is not about a client despite going against the branding of the name, but about a story of a non-profit that turned very challenging. As we go through the story, we’re going to get a bunch of lessons and details that definitely are applicable to working with any client or a boss. Mark Jacobsen, it’s great to have you tonight.

Mark (Interviewee): Thank you, it’s a pleasure to be here!

Morgan (Host): Let’s jump right in! I think a good starting point is if you start by telling us the adventurous story that I read all about in your book last night, and you, listeners, should also.

Mark (Interviewee): Yeah, thanks!. Despite that introduction, I’m an air force officer who’s also an entrepreneur, still on active duty, but have done a lot of entrepreneurial things, and the book that morgan referenced is one I just released titled, “Eating glass; the inner journey through failure and renewal,” which is a part memoir but is also partly a guide to help people who are navigating the aftermath of a brutal failure experience, which I’m sure we’ll get into. It’s something that we don’t necessarily talk about enough, so my story begins in 2013, 2014. I was a c-17 pilot in the air force; if you’ve been following the news in Afghanistan, these are the cargo planes that are trying to evacuate people. 

They are long-distance cargo planes, and my job was to move cargo and people in war zones. I am also a middle east specialist; I spent a couple of years learning Arabic living in Jordan, I earned a master’s degree in conflict resolution there, and I’ve always had an interest academically and personally in civil wars. My story started in the 2013-2014 time frame when the Syrian civil war had started. It was an absolutely brutal conflict, a peaceful uprising that became violent, particularly as the regime attacked its own people. 

I was in eastern turkey doing research among Syrian refugees for a degree program when the Syrian government started starving out entire cities as a means of breaking their will. I was meeting people who had survived sieges, who had loved ones inside starving, just horrific news, and people would ask me as a cargo pilot, “Why doesn’t the united states go in and deliver aid? You can do whatever you want; you’re the air force?” Speaking as an air force pilot, the honest answer is, “No, we can’t go wherever we want, especially in the middle of a hot war zone. Big cargo planes get shot down unless we launch a whole war to fight our way in, which we weren’t at war with Syria.” But that got me thinking, surely in the 21st century; there must be a way to get some aid into besieged areas. 

I couldn’t let that thought go; I felt an obligation as a c-17 pilot, as someone who spoke Arabic, as someone who knew the region who was studying the war, to try and think about how he could do this. To make a long story short, I had an idea of using large numbers of small drones to swarm small packets of aid, so the image in my mind was like a conveyor belt just delivering parcels or maybe an army of ants stealing a picnic lunch, and you could get a little bit of aid in over and over, and potentially feed a cit, Or, if nothing else, at least get in high-value, low-mass goods like medicine, baby milk, whatever it might be. I spent a couple of years building a non-profit around this idea; all I had was my own resources; I was bootstrapping with my own money, building in my garage, learning about radio control airplanes and drones, and autopilots, reaching out to my networks to find volunteers. 

It was a very scrappy grassroots effort, but we did manage to bootstrap it. We started building the technology; we built drones, we did have a lot of success, we built drones that could fly a hundred kilometers and deliver packages, we did a major event in California where we trained Syrian-Iraqi refugees on how to operate our planes, and we had families building parachutes and packing boxes. We really showed that this paradigm could work, and we did that in the United States. So, our next step was to try and get to Turkey, adjacent to Syria, where we hoped to replicate this demo and demonstrate that everything was ready to go. 

If we could just get the right legal permissions, we could get the first drones over the border now. As you can imagine, this is an incredibly complex project; very early nascent drone technology was politically complex, it was legally complex, so we had to fight a ton of battles to get this far, and we were badly burned out, but we kept trying. We knew that the sieges would be moving north to Aleppo near Turkey, and we were trying to prepare for that moment. But we came to a make or break moment where right after we did this major event in California, we were broke, we were bootstrapped, we needed money, and there was gonna be this really nice BBC documentary coming out about our project, and we would have one shot to raise money. 

So we decided to do a crowdfunding campaign where we would launch it at the same time that the BBC story broke. We would try and ride that publicity wave and get not just the funding but the political support that we needed. We kind of bet everything on that campaign because it was our one shot, and I was very nervous about launching a crowdfunding campaign, given that we could not guarantee how this would turn out. This wasn’t like delivering a book, an app, or something; we were trying to access a war zone in a very complex war. We did it anyway, we ran the crowdfunding campaign, and right around the time that was coming together, the wheels started to come off. 

Our volunteer team was badly burned out, me most of all. Our lead engineer was in the same boat, we’d expended a lot of our resources, and we were largely Stanford students. This happened while I was at Stanford earning a Ph.D., so we were trying to hold it all together. Also, the war got considerably worse; the rise of the Islamic state really changed the political dynamics and the optics, and there was very little will to do humanitarian work in Syria. Turkey got increasingly dangerous very quickly, and then in July, a couple of months after the crowdfunding campaign, we actually crashed a drone at Stanford in a dry lake bed called lake Lagunitas and started a brush fire that burned three acres of Stanford and very nearly escaped and became a wildfire. We got that contained; the fire department did; we were very lucky it wasn’t worse, but that fire sort of symbolically represented the implosion of our effort. After that, our back was broken, if you will, we had a very difficult time trying to get moving again, and we realized this just wasn’t going to happen. But we had all this crowdfunded money sitting in our bank account, we had all these pledges and promises we had tried to make in good faith, and for me in the leadership seat, I had to figure out how do I continue leading an organization that is failing if it has not already failed. 

For me, that set in motion a very difficult season of my life of severe burnout, stress, feeling like we’d failed and let people down, and trying to navigate that experience while still leading the team responsibly shutting down the organization. Then finding my way forward again a year or two after that when everything I had poured so much into with my team had come to an end, and that’s largely the journey that I talk about in my book is that when you are an entrepreneur, and you have led something like this, poured your heart and soul into it, and it doesn’t work out, how do you move through that time and how do you get going again?

Morgan (Host): It’s a powerful story, even more, powerful in the book where each of these moments that you are alive over in one sentence in excruciating detail.

Mark (Interviewee): Yeah, excruciating. Is probably about right; I don’t want that to turn you off because it’s a redemptive story, I hope, but it was a very difficult season of my life, and I think it’s a common experience for entrepreneurs when you talk to people who have led a startup through failure, you know some people just seem to it bounces off. But there’s a subset of people who strikes them like the death of a loved one; it’s a traumatic experience.

Morgan (Host): Even for the people where it seems like it just bounces them off or bounces off of them, the rubber people, it turns out humans aren’t rubber, so these sort of people, in my experience, are those people who are fine but then five years later it all comes out and then have some form of delayed post-traumatic stress syndrome.

Mark (Interviewee): Yeah, I think you’re right. When I talk to people about this, what I tell them is, “If you don’t do the work to process that, it will become kind of a shadow that follows you around. It’s going to affect you in ways you might even understand, it can affect your family, it could affect your leadership style, or how you go into your next venture. So sooner or later, that bill will come due,” and I just encourage people to do the work of processing through those experiences. 

Number one, to avoid that shadow haunting you, but also because when you face it and when you grapple with it, you can actually really grow through that experience; how we learn to process those things can teach us practical lessons that can also really enrich us as people, helping us understand ourselves, our strengths, our weaknesses, how we lead, how we deal with challenges, and for me, it was a very difficult time, but it’s also a very fruitful time.

Morgan (Host): Yes, that makes sense. So one question that I kept on wondering as I read your book last night was the following; if you had to re-do that experience, what would you have done differently in order to manage a lot of the different situations and characters differently?

Mark (Interviewee): That’s a great question, and it’s challenging because this was a crazy project from the beginning. This was a moon shot, right? We celebrate moonshot thinking; we read inspirational books about it, excite ourselves about it, and tell people to go pursue their dreams and change the world. But the reality is that when you pursue a moon shot and give it everything you have, you create kind of a dangerous situation with a high risk of burnout because you’re feeling this thing with your passion, energy, and love. 

Then when it crashes and burns, you’ve got a lot of yourself wrapped up in that; if it crashes and burns, I should say. But I’m not sure if you could pursue a moonshot any other way, so you know, I sometimes ask myself, was it foolish to try this at all? This was always a long shot; was it wise to just invest every waking hour in a project like this while I was still a Stanford student and dealing with my family. I don’t know; I think to some degree, it was always going to take a lot of time for me to try this. With that said, I think there are some things I could have done differently. We talk a lot about things like setting healthy boundaries and maintaining healthy lifestyles. I think anyone who’s doing entrepreneurial work, that’s an important lesson, and it’s very easy to discount health.

Morgan (Host): Let’s dive inside of that a bit. I like your phrase to set healthy boundaries, but let’s be specific with that. In the entrepreneurs or the non-profit founder’s journey, what are some boundaries that, for example, you think it might have made sense to have said? By the way, what makes it challenging is exactly your comment from two minutes ago that to do a moonshot, you put yourself in, and you put your heart in, which is fundamentally the destruction of the boundaries. So the real-world question is, how do you balance the two?

Mark (Interviewee): Yeah, so I think there’s kind of a more inner-soul level of this, and there’s also a more pragmatic day-to-day level. At that inner soul level, somehow, we have to recognize that we are not our work, and we have to be okay having an identity outside that and that if the work doesn’t succeed, we can still have our identity. But that’s hard to do because we put so much of ourselves into this thing, and that’s just, I think, something you learn through living, doing it, and trying to be wise. 

The tactical day-to-day, it’s very easy to let healthy habits slip; things like physical exercise, sleep, nutrition it’s all the basics we know it. But when you’re in the hot seat, you make excuses for why you don’t have time for that, you need to do this, you need to do that, and often entrepreneurs are very high-energy people. We’re often manic, if not literally than metaphorically; we have tremendous energy, and as I was going into this, I felt strong, I felt capable; I had never felt so alive as leading this great humanitarian project. I was able to get by on not enough sleep; I was able to work from dawn till dusk, take care of my family, and be a student. I convinced myself and said, “It’s okay; I don’t need all these other healthy habits and boundaries.” The subtle danger there is the damage accrues over the long term; it doesn’t hit you in a week. It might hit you in six months, and by then, it’s too late. So I think from the beginning, keeping healthy daily routines, I think there’s a lot of other kinds of tactics, having a good morning routine of waking up and having time to start your day before you engage, the same thing at night, how you unwind and how you shut down.

I learned too late in the project not to check my email after about; I don’t know, 8 p.m; because if I did, something would blow up my night at 8 or 9 or 10 o’clock, and I wouldn’t sleep that night. I’d lay awake, stressing and wondering. My mind would be going 300 miles an hour, so I think there are a lot of just wise things we can do. Then if you’re a leader, also trying to bring those disciplines to the people who work for you, one of the things I realized as someone who led volunteers was that they were motivated by their passion. They weren’t going to sleep; they were going to do whatever I asked because they were intrinsically motivated, so for me as a leader, I would not throw things at them at nine o’clock at night or encourage them to take a weekend off. Those kinds of things lead to a much healthier team; they give you more energy and more an ability to run the marathon over the long term. So when I went on later to do the second type of startup, I tried to lead more from that place. 

Morgan (Host): I think that’s an excellent framework; I want to share two personal ways that I do in order to deal with this because perhaps for someone listening, this might help. Everyone knows it’s healthy not to check your email on this and this, but when your heart is in it, and you’re so into it, it becomes hard. Here’s what I personally thought; first, about 20 years ago, I decided that I was going to spend 90 minutes every single night of my life, no matter what, improving my writing and the process that I decided then is to spend 45 minutes reading or rereading classic literature and 45 minutes writing for fun like not for work. By committing myself emotionally to that ritual 20 years ago and doing it no matter what, the most stressful, difficult moments for me have become a form of catharsis. 

No matter how crazy and intense things are, I need to disconnect that I’m never going to bring that ritual no matter what, that I need to disconnect in order to force myself to get distracted. A second version is one that I only have to do by myself, but I should do more. I’m a fan of the ancient Jewish wisdom to just disconnect for one day a week, you know, the Sabbath. And what’s powerful about that is everyone knows it’s healthy to disconnect; that’s why weekends exist; it’s only good, but when there’s so much pressure, so much to do, it’s really hard to do this. But what’s powerful about the idea of the Sabbath is it’s the force of God behind it. If God says, you have to do this, like I’m doing it, so it’s like a best practice, but because it’s given this religious framing, it gives it so much more power to really force you to disconnect, which forces your mind to disconnect and really goes a long way towards being able to set these sorts of boundaries.

Mark (Interviewee): Yeah, I love both of those; that’s great! I come from a religious background, but I’d say the tradition I was raised in, Protestantism, never quite valued the Sabbath the same way that Jewish people have. I’ve always had a deep respect for that because you meet people who truly observe the Sabbath, like the power that it has. The closest I probably come is getting outdoors for a day and going out to the mountains; I do that fairly regularly and disconnect to spend time with nature. The writing I love your word, “ritual,” that’s something that I’ve tried to do because I love to write. I’m trying to be better about it, and I’ve never had that level you at.

Morgan (Host): What’s awesome about rituals is that rituals over time build an almost godlike power and force behind them because if you just say, “Oh yeah, I’m going to write,” as soon as your drones are exploding, you’re burning down Stanford, you’re running out of funding, and the disasters are happening, for humans like, “Okay tonight I’m not gonna write I have major challenges to do.” But when you have these deeply embedded rituals, it just forces this emotional disconnect which I find would really help with these boundaries.

Mark (Interviewee): Yeah, and I think that’s huge. Also, I think there’s something powerful; you used the word “catharsis,” and I think that’s helpful too. I think there’s something about creative types of activities; a lot of leaders have had these, like Winston Churchill, who led Great Britain through its darkest hour. He had oil painting was something he did in the midst of the war with the bombs falling on London, you know, he would do things like this.

Morgan (Host): While he also wrote the history of the English-speaking people, for which he got a Nobel prize in writing, and I’m like, “You’re like leading the free world to save them while painting while writing the funniest best history of the whole Anglo-Saxon.” It sounds more like a fictional novel than something a human being could do. Okay, I like mining your book, and I want to continue on this question to click back on the browser for about five minutes before the original question about what you could have done differently. 

Let’s say the lessons learned applied retrospectively, so this first lesson is the power of healthy habits, especially the boundaries which we dived into. I’m wondering what else you learned; I’ll frame it more specifically; there were a couple of moments in reading you’re reading your book where I was like, “Oh, it’s interest that he dealt with it like this, not like this.” So for a specific moment, reader, fast forward here if you don’t want to know what happens one moment in the book, there was a moment where you told the board you’re going to close it down, and then the board was like, “No sorry, you can’t.” Then you’re like, “Okay, I’ll keep it open.” To me, my instinct was that it felt weird and strange when the founder wanted to close it down, and everyone’s burned out for the board to force you to keep going. Because in the situations where I’ve seen where the key players all want to stop, but for external pressure, it doesn’t, it turns into like a walking dead scenario, when it’s like the walking dead scenario, it’s always better to just be dead. 

Mark (Interviewee): Yeah, right! That’s a great question; that was like in a couple of months after the fire, we were dead in the water, and I was agonizing over what we do. I felt like I was making this brave decision to shut the organization down because I wanted to be decisive for our terms and just wrap this thing up so we could get on with our lives. I didn’t want, as you put up, the walking dead, you know, the zombie organization lingering, and you know my mistake there was we were actually incorporated. We had a board of directors, and it was not in my authority to dissolve, but what I ended up doing was just shooting out an email saying, “Hey, I’ve made the decision that we’re going to dissolve and actually notified some external stakeholders,” and then the board was like, “Whoa you can’t do this.” I just made some screw-ups there, which came from inexperience. 

I had never led an incorporated organization before, and you know, having started in my garage that this shift from that of me just doing stuff to having a board of directors and a governance structure was new. There was a lot of rookie inexperience; what I probably should have done was gathered the board, let’s talk about it, and make a decision. Now there’s a broader issue here that might apply to other entrepreneurs, which is you’re always in this world of uncertainty, and you don’t know when things get hard; you don’t know if you should keep pushing or if you should stop. 

And I’ve got a whole chapter in the book on you to know when do you quit, but that’s something we don’t talk about, we don’t like the word quitting, and a lot of that has to do with risk. Well, what’s the risk if we try doing this? If we keep pushing, when do we cut our losses? And this is maybe something I would do; differently, I just didn’t know how to handle it at the time, but I saw all these negative trend lines happening that, you know, we had a lot of success, but things are going off the rails. My strong intuition was we were moving too fast, and we needed to slow down, and this was before we got to that kind of dissolution. So other people on the project and external supporters were like, “No, things are going great! You’ve got to double down and keep pushing when things get tough, and you’ve got one chance to go fundraise, you’ve got one chance to make this thing happen, you got to be bold, (that word kept coming up, be bold), and go do this.” I had a decision to make, do I trust my own intuition, or do I listen to these other voices? 

I know my own weaknesses; I can be risk-averse when I don’t know how things are going to go, and I said I’m going to trust these other voices. I kind of went against my intuition, and then the same thing happened a few months later after the crowdfunding campaign; with this decision, you’re talking about, do we dissolve? I want to dissolve, but other people are telling me no, we want to keep trying, and I went against my intuition again. So what lesson to draw from that? One of mine is to stick to my intuitions and argue for them. But I also know that sometimes I am wrong; there are other times my intuition was to back off, and other people challenged me to push harder; I did, and it worked out. So I don’t think there’s a right answer other than to be very thoughtful and recognize these decisions. But maybe don’t avoid the hard truths, the hard truths are staring us in the face, and one of the most challenging things as a leader is to get your team to look those things in the face and really talk about like what do they mean for us? Let’s not minimize what’s going on here because this is the existential threat we’re facing; how do we deal with this? Let’s not shy away from it and have a very sober conversation about it.

Morgan (Host): Well, I think it seems to me that there are a couple of lessons that we could get out of this moment. One is that it’s not that people’s intuitions are always right, some people have better intuitions than other people, or some moments of your intuition are stronger than that other moments. But what it seems to me is that intuition always has. When you subconsciously realize that there’s a huge problem that needs to change, that’s what intuition always has in common like before you consciously realize it. What that means is when you feel intuition, maybe the intuition is just like, send out the email and close it down wasn’t right, but you have to take what your intuition is saying and then really find a way to meditate on it. Think about it and turn that into a strategy; maybe when you feel this gut instinct, that’s when you get an outside voice on it, for example. Or maybe you set up some sort of process in order to to see if it could lead to a change. I’m a big believer in listening to your intuition, but rather than just doing what your intuition says, strategizing based on what your intuition says.

Mark (Interviewee): Yeah, that’s a really good insight. I went on to lead a second software development team later, a couple of years after this, and I practiced that in maybe a different way. I often felt fear; there was always some threat, and I was always worried about things and anxious about things, so I had to kind of learn to deal with anxiety. However, leading that team, I had learned a lot; it went much better, but like I’ve got all these anxieties which is a kind of intuition sometimes. And I had to do exactly that like let’s take this phantom, vague, nebulous anxiety, and write it down on paper and then just analytically ask myself what does this mean, what am I actually afraid of, what are the concerns, and what are the mitigation strategies. You’re right; that’s very powerful. 

Morgan (Host): Thank you, so that’s one lesson. Another lesson is this; you said that some of the advice that you had gotten was to be bold; in fact, I remember, sorry, I happen to have an awesome memory, so I remember how you said that in your book, which was that you were influenced by the work of Peter Diamandis who’s mantra was “be bold.” You even repeated it three times. It was like, “be bold, be bold, be bold!” I like the triple emphasis. So what’s interesting about that is when your thought and strategies are so influenced by someone else, like you explicitly talk about the amount of influence, it often becomes hard to separate out what you want and what’s best for you from these really smart people who are giving you advice. Hey, Peter Diamandis is really smart, be bold is, in general, great advice. 

But like with any general advice that you would read in a book, it’s different in every situation, every person; some moments you have to be bolder than other moments. So I think another lesson is when you unwind about why you feel these things, and this piece of advice to think about where the other advice comes from, and then think about the qualifications and how the applicability. You can’t always be bold, there are times for boldness, and there are times for tranquility as well.

Mark (Interviewee): Yeah, that’s so true. I feel like for any principle that you want to throw on the table, you could probably come up with the exact opposite principle. One example is from Winston Churchill again, “never, never give up.” On the other hand, you got sayings like, “you got to quit while you’re ahead,” “you got to know when to cut your losses.” You can have this tension for almost anything, and that’s where wisdom comes in. Wisdom knows what to apply when, and to your point about, you know, reading these books and being influenced; one thing I do worry about is that we have a whole cottage industry of books feeding a message of going out and pursuing everything you have. 

Be unstoppable, go be a badass, go be bold, launch your moon shot, and if you keep failing, then just keep trying, and you’ll succeed. All good things, I love those books, I spent a lot of time reading those books, but in some ways, they misled me because I probably was not very wise about how I applied that. I probably pushed too hard and didn’t have enough countervailing wisdom about things like, you know, just the pragmatics of building a scrappy little organization, making it sustainable, not burning people out, and really testing our value proposition to ensure that we are building the right thing. Is this gonna solve the problem we think it is, and there’s a whole pragmatic side of running a business or an effort that you need a range of advice? 

In my eagerness to someday be an entrepreneur, I had only consumed maybe one-half of the equation, and when things really fell apart, I also had no idea where to turn because we don’t have a lot of support for that side things. When things are falling apart, how do you lead? When your organization ends, and you’re just sort of adrift afterward, what do you do? That’s where you really need a lot of wisdom; that’s not always talked about, so you got to be careful of the selection bias in the books that are out there.

Morgan (Host): I actually just realized something while I was listening to you now. Before I hit record and we started this podcast, I was telling you about how an aspect of your book that I appreciate is that one of the subtexts is your internal struggle with the religion that you grew up in. What’s interesting is that all these books that you just alluded to, some of these books are inspirational like you can do it, you can succeed; there’s an interesting parallel to like the corpus of religious texts. 

There are just like these industries; I don’t mean this necessarily negatively; I’m trying to be neutral and dispassioned here, but there are these industries in both cases that are trying to tell you that redemption is right there. You just have to do these really intense things with your whole heart and soul, and you will be redeemed; you will be saved. But in reality, these things are lotteries, and guess what? Almost everyone loses the lottery.

Mark (Interviewee): Yeah, that’s so true! If you think about these industries, they exist to tell people what they want to hear, right? If you’re a book publisher, you’re going to sell books telling you how to go succeed and achieve your dreams. There’s a place for that for sure, but it does create a danger when we’re trying to tell people what they want to hear, and it is almost like a civic religion in a sense in this country of the inspirational. Go pursue your dreams; I’m a believer in that, but also, again, be wise about it and recognize where that meets reality.

Morgan (Host): I want to dive into that first thing because it comes to the heart of some of these challenges; the American religion is that you too can be president, but the reality is that there is no universe under which I could have been president of the United States. My parents told me when I was a little boy, “If I really want to be president, I can be,” but nope, that’s really not how the system works. 

Also, what’s interesting is there are other very similar industries where people realize it’s a lot like music; everyone knows if you start a garage band, you’re probably not going to be the next Beatles. You do the garage band and have fun, but only a very few people will actually think that they’re going to be the next Beatles. You do it for a couple of years in high school or college, and then it becomes like a Sunday hobby or something. But in silicon valley land, everyone believes that, yes, my company is going to be the next Facebook.

Mark (Interviewee): Right, and to use your example, once you accept the reality, it kind of frees you up to enjoy things more. If you’re out in your garage with your guitar, frustrated to no end that you’re not making it, you know being a celebrity, you’re going to be miserable. But if you can just love what you’re doing and go jam with your friends, it kind of frees you up. You brought up writing; I’ve dealt with that with writing because I love to write and I’ve never quite “quote” made it. It can be very demoralizing, and at some point, I have to just accept that, you know what, I love this, and I enjoy it, I’m going to keep doing it regardless of where it leads.

If you’re starting a company or an entrepreneurial effort, you can do the same thing. If you want this thing to succeed, you’re going to take it as far as it goes, but you may learn to be happy and content with, you know, the marginal contributions. My effort failed in the sense that we did not deliver aid in Syria, but we ignited a conversation that hadn’t really happened before about how you could use humanitarian drones in conflict zones. It was discussed in U.N meetings, and non-profits were involved, and you know, a lot of people on my team went on to go do other work. 

One of my volunteers is helping get Afghans out of Afghanistan right now, she’s organizing cargo flights like we planted seeds, and this is a big theme in my book. If you can just set this thing in the proper context, love it, enjoy it, and not put everything on this moonshot success home run, there are plenty of little wins along the way that you can kind of cherish, enjoy, and just watch those seeds being planted and bloom in ways you never expected. Just like if you’ve got that garage band, you’re going to make friendships, and people are going to go off and have life experiences, you know your lives have been enriched by what you did.

Morgan (Host): Yeah, that makes sense; being present in a moment is both surprisingly powerful and surprisingly hard to do. Another moment in the book that I want to talk about because it was also surprising; it might be something else to have done differently in retrospect was your decision to organize it as a non-profit. At some point in the book, you even called it out; you say that there were a bunch of people around you. I said, “Oh, it’d be much easier to raise money for this if this were structured as a for-profit.” Perhaps I drank too much from the silicon valley kool-aid, so my instinct is, well, even if the goal is to do good, you can get much easier access to capital and etc. In a classic startup structure as opposed to a non-profit structure, in retrospect, what do you think about going this path for that path? 

Mark (Interviewee): Yeah, so that’s a great question. I think we did the best we could under the constraints, but let’s unpack that. I’m a military officer; I was still on active duty when I was at Stanford; I never had the ability to quit my day job to go run a company. So this was always something that was kind of shoehorned into weekends and evenings, and I was never going to be able to go spend my days talking with investors. So we were sort of necessarily scrappy. Also, we were trying to actually access war zones, doing things only governments and militaries could endorse, so what I envisioned was this becoming a military capability, just like the military could go deliver, you know, pallets with a c-17, we could deliver you know a bunch of drone teams and drones and go do this. I was just trying to create a temporary home for this idea to prove that it could work and then find some way to on-ramp it in the military, which doesn’t really have an analogy in the private sector. Now, how did we gone a for-profit? Let’s just say we’d solve that leadership problem; a lot of things we didn’t make sense. We discussed this with people at Stanford’s graduate school of business, we explained what we were doing, and they would say things like, “You are all over the value chain from top to bottom. Why are you talking about building your own drones, flying them, training crews, and delivering cargo? Each one of those could be its own company.” 

We were just trying to solve an immediate problem of getting these stuff into Syria, and because none of those companies existed and that infrastructure didn’t exist yet, we kind of had to own the whole stack, I felt like, so it was just too messy and new of space to really be a viable company in a very short time frame. But yes, you’re right; what are its points to sustainability? For this idea to really become sustainable, it would need a sustainable organizational structure that could have been getting folded into the military, but frankly, a company is more sustainable than a non-profit or a lot of other things.

And if we’re going to generalize a lesson there, from the beginning, we knew we had a sustainability problem. I had three years at Stanford, and I was going to go back to the air force, so I couldn’t have any time to do this again. I was also kind of the nexus of everything. This team wouldn’t have outlived my leadership very easily, and we were sort of hoping we would find some way to transition this to somebody and make it sustainable later, so there was magical thinking from the beginning that “Let’s just kick that can down the road, and we’ll solve it later,” and that caught up with us sooner than we wanted to admit. Having to grapple with the fact that there’s no real solution within reach for this, so anyone who’s starting a venture, you gotta be really careful about that magical thinking. You don’t have to solve all your problems right away, but if you don’t have a business plan that makes sense or you know you’re not sustainable, that probably is your number one priority to figure that out. For me, I just kind of denied that reality until it was too late. 

Morgan (Host): Avoiding magical thinking is an awesome lesson. Let’s continue diving into some because it’s interesting; a point you just mentioned a moment ago that I also remember in the book was that you started this as a non-profit, but you realize that for it to succeed, eventually, the military would need to absorb it. And then you have a page or so in your book talking about that, about the military’s failure to absorb it or their lack of interest in making it happen. 

So, having to work with some private companies that are crazy bureaucracies it’s the same challenge as trying to motivate or get a bureaucracy to do something differently. Something I’ve learned is that’s possibly impossible to do, so I was curious for some caller and some lessons on trying to get the military bureaucracy to change, and if, in retrospect, could you have approached the military in a different way to have made it more excited or more possible to support this?

Mark (Interviewee): So this is where I spend a lot of my time now, still being a military officer, and I’m actually a professor who teaches innovation in the military, so this is my wheelhouse. I think trying to innovate inside a large organization is so different that it needs its own words and its own way of thinking. I like the word “intrapreneur,” which isn’t commonly used to refer to someone who does the kinds of things an entrepreneur does, but inside an organization of creating new products and services and fighting for their adoption.

Morgan (Host): By the way, I just have to say, I own the domain “” Twenty years ago, I owned it, and at some point, I let it expire. Who knows who uses it today, but I’m like, “Oh wow, I went to” 

Mark (Interviewee): That’s great! Yeah, I’ve been trying to do some writing on that, I got some stuff on my website, which is @Mark d, but anyway, I think the key difference is that a lot of people who are entrepreneurs go read all the entrepreneurial books, listen to the speakers, and watch the ted talks because that’s what’s out there. They try and just carry that into their organization, but the rules are different. You don’t get adoption because you have a great idea. You can’t just take it out to the market and let the market decide. In a large organization, ideas get adopted through the bureaucracy; resources get allocated through the bureaucracy, decisions get made somewhere in the bureaucracy, even getting manpower, your own manpower, your own hours, is a decision made by the bureaucracy. 

So, learning to be an effective entrepreneur means learning the rules of the game inside your organization; it means learning who controls resources, who do I have to convince, and who do I pitch to? If I got prototypes doing well, how do I get that noticed at higher levels? Who has the authority to create a new division of the company or adopt this new product? Who’s got the ability to program out labor, so I have a team working on it? Who can improve experiments? All these questions, they’re very different in every organization, so the effective entrepreneur becomes, I think, kind of an insurgent where you’re down, you know, doing ninja tricks at the bottom of the pyramid to kind of find your way up to champions of the right levels which can help this thing get a shot. It takes a very carefully balanced attitude; on the one hand, you’ve got to be that insurgent who’s willing to do things differently, operate around the edges of how the company normally works, but you also have to be very loyal. 

You’ve got to show that you’re the kind of person who has the organization’s best interest at heart, that you’re a professional, that you’re competent, they can trust you to do your day job; that’s how you sort of get the trust and the access to higher levels to adopt your ideas. I’ve done that pretty well in the military, and I think I had the respect of the air force while I was doing this. My work got briefed to the chief of staff of the air force, the very top general in the air force, and he gave it a thumbs up. He’s like, “This is awesome! Keep at it; we need innovators.” The problem was that it didn’t translate into any resources; it was just verbal praise. I was very naive about the realities of what it takes to get resources and get ideas adopted; there was no way from the beginning that it probably would have happened. 

I learned a lot more about that later with my second team, the software development team, which was inside DOD. I became a lot more effective there as I kind of learned those rules of the game, and then at a personal level, if you’re inside an organization, you’re often very frustrated. You’re imprisoned by this bureaucracy that just makes everything hard, so there’s kind of a personal level of taking care of your own health is learning to take a deep breath and not let the organization get to you, which is kind of a different skill set or a different maybe a requirement than like an entrepreneur faces who’s got a lot of autonomy and freedom. Your battles are more of getting money and whatever, but it’s just a different operating environment.

Morgan (Host): Those are great lessons; I would say for a lot of the people who are listening, all three of you, hi! Hi mom! Dealing with the bureaucracy has a whole other level of difference because the entrepreneurs, you’re inside the bureaucracy. But then there’s like the external vendor or external contractor who’s trying to deal with bureaucracy, and it becomes even harder because you’re not on the inside. And if you are not on the inside, you don’t have access to the information or the people or really know what’s happening, and it’s a whole other can of worms in order to figure that out. 

Mark (Interviewee): That’s a great point; my last job in government, I was working with private sector companies, and I kind of had all the cards of being in government because I had the trust of being inside and having that information. But I saw the frustration on the private sector side of trying to do business with the government where they were trying to figure out the rules from the outside. Yeah, there’s probably a lot of analogies to that, and then another thing we didn’t really talk about is like social change, if you’re out leading an environmental movement or something, whatever the case might be, you’re trying to create social change, you are trying to persuade or influence actors that you’re not necessarily a part of, it’s a whole other world of how you create change.

Morgan (Host): Yeah, I agree. Those were the questions that I thought of when I read the book last night that I wanted to ask. To wrap up, stepping back now that we had that conversation, first, I can’t stop myself from saying I’m happy to have proved to you that I actually did read the book with me calling some specific details. But wrapping up something back, are there any other lessons, insights, or final points that you would like to make or perhaps repeat and emphasize to conclude today’s podcast?

Mark (Interviewee): I would just say, in conclusion, for people who want to lead a bold moonshot type project, by all means, go do it. But from the beginning, take care of yourself, pace for a marathon, take care of your people and find part of your identity and your happiness outside the project. Try to love the project, give it everything while at the same time holding it at a distance. I think that’s maybe the biggest takeaway I took from how to lead something like this. I’ll just say, we didn’t talk about it as much, but for those who have gone through a failure where something you have given your heart to comes down, and you’re looking for guidance, I’ll just offer up a last mention to my book, “Eating glass; the inner journey through failure and renewal.” There are not a lot of resources for those situations, and that’s really what I wrote it for, especially for those people. Just embrace the lessons, do the work to face that, and grow through them. That’s how we become wiser and better the next time around.

Morgan (Host): This is why we’re talking today; where even though this podcast is targeted a little bit differently, it’s about horror stories. A horror story fundamentally is about a failed experience, which is why a lot of the different lessons that we’ve spoken about from the set boundaries, dealing with self emotionally, practically dealing with bureaucracies, and so on applies in both situations.

Mark (Interviewee): Absolutely!

Morgan (Host): Mark, it was great to have you on. I hope you enjoyed this conversation as much as I both enjoyed it and enjoyed reading your book as well. 

Mark (Interviewee): It was wonderful! Thanks for having me; I appreciate it.

Morgan (Host): And everyone who is listening, thank you for watching! Thank you for watching and listening; until next time.


This transcription belongs to Episode #20, please watch the complete episode here!