Hi Mark! Who are you and what are you currently working on?

I’m an Air Force officer, a writer, a professor of strategy and innovation, and an entrepreneur. I just released a book titled Eating Glass: The Inner Journey Through Failure and Renewal. I wrote the book after founding and leading a moonshot nonprofit effort to break starvation sieges in Syria using swarms of small drones. The effort ultimately failed.

Nothing in my experience prepared me for the emotional and mental journey of a major failure; the “fail fast, fail forward” mantra is obviously important but glosses over the very real pain. I wrote the book to help others navigate their own journeys.

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What’s your background and how did you come with those ideas?

I was an Air Force C-17 cargo pilot, tasked with flying cargo into war zones. I also grew up building robots with my dad, taught myself coding, and created numerous software projects in the Air Force. I also spent three years learning Arabic and earning a Master’s Degree in Jordan.

Around 2013 the Syrian government began using starvation sieges and medical deprivation to break the will of the Syrian people. In 2014 I did research among Syrian refugees in Turkey, and it seemed like every conversation was about the sieges. I couldn’t stop thinking about the problem. It was impossible to fly big cargo planes into Syria’s heavily defended airspace, so I conceived the idea of building an air bridge using large numbers of small drones. I consulted from the beginning with Syrian activists and aid organizations, who saw promise in the idea. We called the effort.

How did you go from idea to product?

I was uniquely poised to tackle such an ambitious moonshot effort because I was an Arabic-speaking cargo pilot and Middle East specialist with a background in robotics, software, and entrepreneurship. I reached out to my network immediately and built a grassroots volunteer team to explore the idea. 

This was not a conventional startup. We were all-volunteer, not profit-driven, trying to address a complex, urgent, real-time problem in any way possible. My strategy was to bootstrap support by setting and achieving small, incremental milestones, each of which could earn us more support and funding.

I used my own money at first. I spent months in my garage or at the local park experimenting with emerging drone technology, while also recruiting and building a team. I was en route to Stanford to begin a Ph.D. in Political Science, which gave me access to fantastic engineers. We also recruited law students and people with nonprofit expertise, who helped us incorporate as a nonprofit corporation.

These first months were incredibly difficult, involving dozens of crashes, multiple engineering re-designs, and countless meetings pitching to people who thought I was crazy. The idea was crazy. But we also started flying drones reliably, airdropping packages, and finding volunteers and supporters who saw potential in what we were doing.

Which were the strategies to grow your business?

At each stage, I set an incremental goal that would advance our progress and help us win greater funding and support. Our roadmap ended up looking like this:

1. Create a low-budget video of autonomous drones dropping packages, which we could use to show that we were serious and raise some funds. 
2. Build drones capable of dropping small packages on 100-kilometer round-trip flights.
3. Conduct and professionally film a major demonstration in the United States, involving Syrian refugees, which would prove that we had everything we needed to take the capability overseas.
4. Repeat that demonstration in Turkey. This dress rehearsal would prove we could get aid over the border if we just secured the right permissions.
5. Fly a single drone over the border and drop medical supplies to a hospital.
6. Assess, partner with a larger organization, and hopefully scale.

We achieved the first three goals. A year after beginning the effort, we were reliably flying autonomous fixed-wing drone flights and dropping packages at roundtrip distances of up to 100km. We conducted an amazing demonstration in California and produced a professional video. BBC also flew out to observe and produced a beautiful video story. In the wake of that success, we launched a crowdfunding campaign to fund goals 4 and 5--taking our capabilities to Turkey and then, hopefully, to Syria.

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When did things start to go in the wrong direction?

Even as we reached the pinnacle of our success, the stress and breakneck pace were taking a toll. We were badly burned out. Many of us were full-time graduate students at Stanford. I had naively imagined Stanford faculty would embrace our passion for social innovation, but our faculty saw us as hopelessly distracted from our real work of earning PhDs. Dropping out to lead the Syria Airlift Project was never an option because I was still an Air Force officer.

The project’s complexity also became overwhelming. The Syrian Civil War grew more complex and brutal with the rise of ISIS (the precursor to the Islamic State), Eastern Turkey became dangerous, and any will to support the Syrian opposition evaporated. I spent months trying to find a way to get our team to Turkey or Jordan without success.

We also struggled to keep up with the engineering. Drone technology was still primitive and emerging, and we spent countless hours shaking out bugs and addressing problems. We didn’t have the time or resources to do proper systems engineering. In July 2015, we crashed a drone in a dry lakebed at Stanford. The ensuing brush fire burned three acres. The Fire Department barely contained it. 

I had a personal breakdown at this point. I had always prided myself on my ability to shoulder superhuman workloads and thought I was expertly managing the stress. But months of continual effort took an insidious toll. I needed to shift my effort back to my Ph.D. studies, but I felt trapped in the nonprofit; we had just completed our crowdfunding campaign and all the funds sat in our bank account. I had no idea how to keep faith with our donors. I couldn’t sleep. I couldn’t even check email without feeling overwhelming dread. 

The team wasn’t doing much better. My lead engineer was badly burned out. Many of our volunteers drifted away, focused on other responsibilities. The nonprofit survived another six months, dead in the water, as we tried to find a way forward. I struggled mightily under the emotional weight. Finally, in December of 2015, we dissolved.

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Which were the causes of your project’s failure?

We knew from the beginning that this was a difficult moonshot with a high probability of failure. 

The complexity and difficulty of the project were certainly a root cause. We were trying to develop and field an unprecedented kind of technology, on a fast timeline, into one of the world’s most horrific war zones, with almost no resources. So many things could go wrong. The political and legal issues in play were staggering. 

Even as we devoted ourselves to the project, we kept asking ourselves, “Is this idea even a good one?” It was hard to know. We tried to responsibly challenge our thinking. We had Syrians on the team and consulted with Syrians and international nonprofits. We talked to people on the ground. But the only way to really validate our hypothesis was to get into the region and start experimenting, which was incredibly difficult to do. So we went a very long way without being able to confirm our hypothesis about the idea’s value.

Many advisors urged us to scale back our ambitions. They (rightfully) told us we were doing too much by trying to implement every piece of the value chain ourselves. They urged us to develop our paradigm in non-conflict zones. We sent two teams through Stanford’s Ignite summer business program. Both teams developed business plans for turning our idea into a sustainable business--but both ditched the objective of addressing starvation sieges in Syria, which was our entire reason for existence. I wanted to address that problem, not build a drone delivery company.

The project’s overwhelming difficulty aside, the root cause of failure was our lack of a viable business model. We relied on volunteers and a shoestring donor-funded budget. The project depended heavily on me personally, but I had a full-time job as a Ph.D. student and the Air Force would call me back in three years. That put us on a clock. We knew we were barreling towards a crisis but kept kicking the can down the road. I thought if we could just prove the technology in Turkey, we could build a partnership with an organization that might take over the work. In retrospect, the lack of a viable business model was fatal from the start. 

I learned a lot about both the opportunities and challenges of relying on volunteers. Passion, humanitarian goodwill, and love fueled our team. That allowed them to perform miracles. Even though the effort ultimately failed, they achieved amazing feats in an extremely short time period. 

However, running a team on passion and love brings real dangers. My favorite definition of burnout is “unrequited love”. When you pour your heart and soul into something, you run a real risk of heartbreak when your love goes unreturned. We cared so deeply, worked so passionately, believed so wholeheartedly in what we were doing. The project’s failure left me bereft. It felt like the universe had betrayed me. I’m now much wiser and more careful about being a good steward of both my own passion and the passion of people who work for me.

Which were your expenses? Did you achieve any revenue?

We operated on a tiny budget. In our year and a half of operation, we spent maybe $12,000 of my own money, $3,500 of prize money from an innovation competition, and $5,000 from donors. Because we relied on volunteers, we paid no labor. Most of our funds went into drone hardware or tools. Some companies donated hardware, software, or pro bono services. Towards the end, we raised $40,000 of crowdfunded donations and won a $40,000 grant that we ended up declining. We donated our remaining funds to charities supporting Syrians.

We never earned revenue nor planned to. As a small scrappy nonprofit, we sought donations. Our most important currency was relationships. We needed partners who believed in us and supported us. By that measure, we had mixed success. Many people were skeptical but we also found amazing allies and supporters.

If you had to start over, what would you do differently?

I went on to found and lead a second entrepreneurial venture: a drone-focused software development team inside the Department of Defense called Rogue Squadron. This felt like such a gift because I was able to leverage everything I’d learned from the nonprofit. We had real resources. Our team grew to about 15 full-time people. The team was a brilliant success; in two years we became one of the most capable small drone teams in the United States government, and we supported hundreds of government organizations with our capabilities.

My biggest lessons were deeply personal. Failure hit me hard; it took me about two years to recover, and I still have scars. That gave me a lot of time to contemplate the lessons, especially since I was writing my book.

First, I learned to be much wiser and more careful about my own entrepreneurial passion. Entrepreneurs tend to be hypomanic; we pour our hearts and souls into things and then ride out debilitating crashes. Now I throttle my energy to maintain a marathon pace. I have organized my life around strong boundaries and self-care. I work extremely hard but my typical day also includes time with my family, exercise, adequate sleep, journaling, pleasure reading, and meditation. I try not to let my sense of self-worth become too entangled in my entrepreneurial pursuits, although this is admittedly a challenge. 

Second, I now take a much broader view of success and failure. Innovation is so nonlinear; the economist Joseph Schumpeter described capitalism as “gales of creative destruction.” We try stuff, the main effort goes sideways, and then unexpected seeds we planted along the way suddenly bloom. My nonprofit failed but we helped start a conversation in the humanitarian assistance world about drones for good; my volunteers went on to do amazing things in the drone industry; I leveraged my expertise to launch Rogue Squadron. 

In my book I write:

Each action you take plants seeds in this wild, vibrant, evolutionary jungle. Every investment in a colleague or subordinate could shape that person’s life. Your discarded creative projects become building blocks for the next generation, or for your own future efforts. Work you abandoned will surface in entirely new places, changed and yet mysteriously familiar. Lessons you learned long ago will help you avert catastrophic mistakes in the future.

This view of the world becomes almost comforting. You are not such a big deal after all, and that is okay. You faithfully play your part in the cosmic symphony. You make investments, plant seeds, and cast your bets on steps towards a better future. How much you plant will define your legacy.

Which are your favorite entrepreneurial resources?

Everybody loves tools, so I’ll mention that I have a YouTube series called Tools for the Life of the Mind, in which I share some of my workflows, which are built around Obsidian, Zotero, and Scrivener.

Beyond that, I’m going to give an unconventional answer to the question. One of the best and most overlooked things entrepreneurs can do for themselves is develop a rich inner life… cultivating a quiet, calm, reflective space in which you prioritize your own well-being and your personal relationships. I think of this as creating a walled garden, to which you can retreat when you aren’t out fighting dragons.

This isn’t easy in our chaotic, noisy, hustling world, especially as an entrepreneur. So I’ll share a few resources to help.

Flow by Mihaly Csikszentmihalyi, who set out to understand how to live a happy, meaningful life. He finds that control of inner experience is essential and lays out a framework to get there.

Jerry Colonna’s reboot.io and his book Reboot helped launch the modern executive coaching movement. Jerry takes his clients on inner journeys through the thoughts and emotions associated with business leadership, which we frequently hide out of sight. His podcast is always rewarding.

The poet David Whyte has written stunning and beautiful books about our relationship with work, like Crossing the Unknown Sea and The Heart Aroused.

Every entrepreneur should have a sport or an athletic hobby. Mine is rock climbing. Exercise is crucial for health and managing stress, but it can also be an incredible training ground for life. Climbing is a zen sport that requires the complete focused attention of body and mind, which makes it a wonderful balm for anxiety. It also requires a dedication to self-improvement and grappling with continual, sometimes overwhelming fear. The benefits to an entrepreneur are obvious.

Where can we go to learn more?

I invite readers to check out my book Eating Glass: The Inner Journey Through Failure and Renewal. I tell the story of the rise and fall of my nonprofit, but more than that, I help readers understand their own journey through a failure and recovery process. That doesn’t have to be an actual startup failure; we all have seasons when we feel stretched beyond our limits, grapple with impostor syndrome or self-doubt, or feel swamped by life. The book speaks to all that.

I also blog (sometimes) and have a newsletter at www.markdjacobsen.com.