The plane that you do not see is the one that will eventually shoot you down. In dogfights with more than two aircrafts, pilots tend to focus too much on the enemy planes that they see, investing too little time searching for the ones that they don’t. More often than not, the plane that they don’t see is the one that ends up shooting them down. In business, we spend too much time focused on the competitors that we “see,” but we often fail to spot the company that will eventually run us out of business. By the time we do, it’s too late. Keep looking…
As a part of my series about “Life and Leadership Lessons Learned In The Military”, I had the pleasure of interviewing Roey Dor, the President & Co-founder of ‘Obligo,’ a financial technology company that rids both renters and landlords from the burden of residential security deposits. Before devoting his work full-time to Obligo, Roey lived in Tel Aviv where he served as Co-CEO of ‘141 Group,’ an Israeli holding group, and co-founded ‘City-People’, an urban renewal company which was recently acquired by a publicly traded construction company. Roey served in the Israeli Air Force as a fighter pilot for 8 years (+12 years in reserve). Following his service, Roey went to Haifa University where he received his B.A. in Economics (2008).
Thank you so much for doing this with us! Can you tell us a bit about your childhood “backstory”?
I was born in New York to Israeli parents. My father was a skilled musician and my mother a talented architect. At the age of 3, my dad was asked to play in a high-profile rock ’n’ roll album in Israel, so we just jumped on a plane and moved to Tel Aviv. I spent my entire life in Israel before moving back to New York in 2018. My childhood in Israel went by with no extraordinary tales. I was a mediocre student and spent most of my free time running outside, surfing and playing guitar. As I grew older, I took an interest in physics and math; but make no mistake, surfing was still my main passion in life.
Military service in Israel is mandatory, but I always felt like I should strive to make the most of it and challenge myself. This is why I spent my last year in school preparing myself physically and mentally to the best of my ability.
And what are you doing today? Can you share a story that exemplifies the unique work that you are doing?
Today, I’m the co-founder and president of Obligo, a financial technology company that rids both renters and landlords from the burden of security deposits. Instead of paying a security deposit upfront, we enable apartment renters to pre-authorize their landlords, such that their landlords can bill them up to a predetermined amount. If a charge is made by the landlord, Obligo pays the landlord right away and gives the renter the option to pay in installments.
Startup work, especially in the early stages, can be very diverse and exciting. One unique and rewarding experience that I recently took part in was organizing a deposit-return party for a building that decided to offer our product to all existing renters in the building. We gathered all the residents together for a big celebration in the communal area. The cherry on top was seeing the residents’ faces once we handed them thousands of dollars back and hearing them talk about what they plan to do with it. We heard so many unique stories and got to know these Obligo users on a more personal level. You’d never expect that such a simple solution could have such a positive impact on a person’s outlook on life.
Can you tell us a bit about your military background?
I served in the Israeli Air Force (IAF) as a fighter pilot for eight years, and continued flying in reserve on a weekly basis for 12 more years. During my 20 years of service, I had the privilege of flying A4s, F4s and a few different models of F-16s out of four different Air Force bases. I met inspiring people, forged strong friendships and, most importantly, met my beautiful wife Yael, the flight simulator instructor who taught me how to fly the F-16!
During my service, I also participated in a few very meaningful, yet highly classified, missions that changed my life. Pilots are constantly being put to the test and often experience moments of uncertainty that have serious consequences. In my experience, these moments helped build my character and improve my decision-making abilities because I was usually required to handle them by myself.
Can you share the most interesting story that you experienced during your military career? What “take away” did you learn from that story?
Unfortunately, the most interesting story is classified, but I would like to use this opportunity to share a story that sheds some light on the more human aspects of flying. It is a story that I believe many readers will actually be able to relate to…
When I was already an experienced pilot, I was sent on a mission that required refueling in midair. Now, air refueling is by no means unusual. Pilots do it all the time and as you gain experience, it comes quite naturally. My mission started and was going according to plan. Being an experienced pilot myself, I felt completely relaxed and in control as I was approaching the stage of air refueling. Then, something went wrong.
All of a sudden, this feeling of hesitation came over me as I started thinking about what was about to happen. Air refueling might sound mundane, but if you stop and think about it — it’s quite insane. At a speed of 300 knots, which is about 345 miles per hour, I needed to fly within 10 feet of another aircraft and align a tiny refueling door on the top of my fighter jet with essentially a garden hose trailing from the back of a Boeing.
I tried to keep my cool and shake off these thoughts. I maneuvered to the right spot and was actually able to connect for a short period of time. But I wasn’t able to shake off my hesitations. I was stressed. I was breathing forcibly. I was fighting to keep my F-16 aligned. Why is this so hard? Why am I moving all over the place? In less than a minute, while these thoughts raced through my head, I lost my position and the fuel pipe disconnected. I lost my time slot and other pilots had to use the little time we had left to refuel. I was forced to return to base with the remaining fuel in my tank and did not participate in that mission.
I didn’t think too much of the incident at the time, as this was the first and only time that I had ever failed at refueling. But the next mission I was sent on that required refueling in the air, the same hesitations crept into my mind. I took off, reached the refueling stage and failed…again. When we debriefed the mission, I had no trouble explaining the technical aspects of why I had failed to refuel. But at this point, I already knew the real reason why I failed — and it was entirely psychological. As a senior pilot, I was embarrassed. I kept my thoughts and struggles to myself, and I mentioned nothing about my psychological issue in the debriefing session.
After two failed attempts, I started imagining what would happen the next time I had to refuel in the air and I really didn’t trust myself at that point. A good friend of mine somehow noticed that I was not my usual self. He approached me and asked if I was okay. It was hard for me to share the internal psychological struggle that led to my failures as I felt it was a sign of weakness. I was now officially scared of air refueling. Sharing my feelings with that friend is what eventually solved the problem. As it turned out, this friend had been working through a different flight-related psychological issue with a therapist. We were able to relate on many levels. He explained to me that certain physical gestures and breathing exercises can have the power to overwrite cognitive deficiencies and boost confidence. Basic exercises like spreading his legs in the cockpit seat and filling up his lungs with air helped him restore confidence in his abilities and improve his performance.
Armed with these new tricks, I was sent on yet another mission that required air refueling. Sure enough, the same wave of emotions and tension came over me before I even took off. I channeled the techniques that my friend had taught me, and it worked. I have successfully refueled in the air many times since. The bad thoughts and fear of failure were still sneaking in, but I was ready for them, fighting them and winning every time.
I think the lesson in this story is that everyone gets scared at one point or another. Courage is not the absence of fear, but the act of conquering it. Many people who we imagine to be fearless, from firefighters to big wave surfers, push through quite a lot of fear and stress to do their jobs. Feeling afraid is OK. It doesn’t make you any less courageous and it shouldn’t stop you from pursuing your dreams.
I’m interested in fleshing out what a hero is. Did you experience or hear about a story of heroism, during your military experience? Can you share that story with us? Feel free to be as elaborate as you’d like.
I hold an unpopular view that many heroes are cast into this role by pure luck, usually bad luck. When we do hear about war heroes, it’s often that they are being recognized after surviving an operation that took a turn for the worse. Don’t get me wrong — they are heroes; they performed professionally under crushing circumstances and kept their cool. I think we should definitely celebrate heroes, but we should focus more on debriefing the incident to make sure it never happens again.
The majority of operations go more or less according to plan, and while courage is often needed, no heroes are born.
Based on that story, how would you define what a “hero” is? Can you explain?
A hero in my eyes is someone who takes care of others when all you want to do is take care of yourself.
Does a person need to be facing a life and death situation to do something heroic or to be called a hero?
I don’t think you need to face a life-or-death situation to do something heroic, although it is sometimes a trigger for heroic behavior. If you’re coping with a difficult situation, one that would break most people and yet you prevail for the sake of others, it’s very likely that you’re a hero. Whether you’re a single mom with two jobs or an elderly person overcoming a spouse’s health crisis, heroes are all around us.
Based on your military experience, can you share with our readers 5 Leadership or Life Lessons that you learned from your experience”? (Please share a story or example for each.)
The first three lessons I would like to share are adapted from ten “dogfight” lessons taught in the Israeli Air Force. Some can be attributed to the “Red Baron” (Manfred von Richthofe), a German fighter pilot from WW1.
- The plane that you do not see is the one that will eventually shoot you down.
In dogfights with more than two aircraft, pilots tend to focus too much on the enemy planes that they see, investing too little time searching for the ones that they don’t. More often than not, the plane that they don’t see is the one that ends up shooting them down. In business, we spend too much time focused on the competitors that we “see,” but we often fail to spot the company that will eventually run us out of business. By the time we do, it’s too late. Keep looking…
- Reduce your speed below 400 knots only if you’re actually going for the kill.
Every pilot knows how hard it is to shoot down a fast flying plane. If you’re flying very fast in a dogfight, you’re almost immune. The speed increases your survival chances, but it also makes you more lethal to enemy planes (speed translates to energy, which aircrafts can use to either dodge a missile or close in on an opponent). In a hostile and uncertain environment, flying fast becomes even more important. Flying fast requires discipline. More often than not, pilots who are restless — or just too aggressive — end up over-maneuvering against the targets they see, wasting too much energy and slowing down. It’s that lack of speed that eventually gets them killed. Our business is like a fighter jet. We should fly it as fast as we can and avoid reacting and paying too much attention to what our opponents or competitors are doing. If we simply fly faster than them, we are very likely to win the battle.
- Don’t deviate course in a dogfight unless you get a “direct order from a general.”
This one is a bit hard to explain and it involves some humor. The humor here is that there’s no way, or time, to actually consult with a general on a decision to deviate from course. In other words, this figure of speech means ‘do not deviate from course,’ period. This is meant to emphasize how dangerous the decision to deviate from course can be and that any deviation should be weighed very seriously.
When a plane is in a dogfight, it is usually turning. Let’s say you’re turning right, performing a right-hand circle in the sky. If that is the case, then it is very likely that your opponent is doing the same thing and he’s somewhere on that circle trying to close on you. If you decide to go into a left-hand circle, your opponent will have a major advantage as they will have a smaller angle on which to close the circle and will be able to position themselves closer behind you. That being said, turning in a different direction can also save your life because the opponent could react too slow or just get confused, and if you’re fighting against multiple opponents, deviating at the right time is required to save your life.
In certain situations, it makes sense to deviate; however, pilots tend to deviate impulsively more often than they should, finding themselves in a worse situation and wishing they had stuck to their original plan. The business lesson here is to respect your plans. Pivots are important — they could very well save your company’s life — but if you pivot impulsively and change your plans too often, you’re very likely to lose. Having patience and letting time work its magic can take you a long way.
The next two lessons are deeply embedded in IAF culture as well, and I think we can all use them in our day-to-day lives.
- The art of debriefing, and how to avoid making the same mistake twice.
In the Air Force, we would debrief on literally everything. If we went on a field trip or organized a party, we would write a debrief, share it with our peers, and file it in a folder. At first it felt like a waste of time, but as soon as we got used to it, we couldn’t stand working without it.
The debrief usually consisted of three components: first, a very short description of the event. Second, mistakes that were made and things that could have been done better. Third, an in-depth look at what specifically could be done in the future to prevent the same mistakes from happening again. The bigger the mistake, the more it is shared. This is why success stories in the Air Force are kept relatively quiet while failures grab the majority of the attention. Relevant debriefs are read prior to additional attempts at the same mission and important lessons are incorporated into briefings
Debriefing is an art, and it takes time to master. At times, we probably took the practice too far, but we rarely made the same mistake twice and we were incredibly efficient. The lesson is to debrief, focus on failures and share what can be learned with other employees. If your organization doesn’t debrief, you are making the same mistakes over and over again and the worst part is you don’t even know it.
- Truth telling as a core value:
All human beings are potential ‘liars,’ it’s only a matter of the price we are faced with for telling the truth. To explain better, I would argue that your first response would be to lie if telling the truth meant a life in prison or the death of a loved one. Try to imagine a situation where you are a pilot who made a mistake and bombed the wrong target. The question is, are you going, to tell the truth or are you going to come up with an excuse that would prevent everyone else from learning from your mistakes?
The answer has very little to do with the actual mistake you’ve made and a lot more to do with the punishment you think you will receive for telling the truth. If the punishment is death, you are very likely to lie because you have literally nothing to lose. If the punishment is missing the next flight, and you know that you’ll receive positive feedback for a thorough debrief, you are very likely to tell the truth. In the Air Force, a sincere debrief earns you respect and trust. You will often gain more than will you lose for a mistake that was properly debriefed. On the other hand, if your squadron commander doesn’t trust you, your jet-flying days are over.
In business, we might think we know what’s going on in our organization as managers, but we have likely been shielded from a lot of bad news. The bad news is extremely important in moving forward and improving, yet our employees are probably reluctant to share it with us. If you can encourage honesty in your organization, you will start hearing some bad news — but this is actually good news!
Do you think your experience in the military helped prepare you for business?
My experience in the military definitely helped me in business. My service taught me how to design and execute plans; make difficult decisions; measure achievements; hold myself accountable; cope with difficult situations; overcome challenges; debrief to avoid making the same mistake twice; and manage relationships with employees, partners, and investors.
As you know, some people are scarred for life by their experience in the military. Did you struggle after your deployment was over? What have you done to adjust and thrive in civilian life that others may want to emulate?
When my deployment was over, to my own surprise, I actually ended up opening a bar in Tel Aviv with two friends from my squadron. We had little knowledge and no past experience, but the business was very successful and we ended up spending a few years in the hospitality industry. We didn’t do it because we were following a strategy or because we were running away from our military experiences, but I actually think it was a good way to adjust to civilian life, and we certainly had a lot of fun.
Are you working on any exciting new projects now? How do you think that will help people?
My business partner and brother Omri and I, are investing all of our time into Obligo. We feel that we can make a real difference by releasing hundreds of billions of dollars that are tied up in security deposits back to renters who can invest this money, or use it to repay some of the consumer debt, which has already snowballed into a worldwide epidemic.
What many people don’t realize is that landlords hate security deposits just as much as renters do because landlords cannot use this money and are forced to open separate bank accounts for each renter. This requires tons of accounting overhead and paperwork. We hope that Obligo will become the new standard for renting in the coming years and that our technology will improve the lives of millions of people.
What advice would you give to other leaders to help their team to thrive?
These days, we tend to expect immediate results when we change something, which causes us to make too many changes in a short period of time. The result is a feeling that we’re making progress, but are we? I would argue that the opposite is true — we are actually hindering our progress. Technology has improved business and communications dramatically, but people and organizations still require ample time to get used to new features and products, or even just to hear about them. A bit more patience, planning and trust in the plan laid out by your ‘past self’ will prove more effective and efficient in the long run.
What advice would you give to other leaders about the best way to manage a large team?
I would advise managers and leaders of large teams to over communicate. I know it sounds trivial, but we tend to think everyone knows what we’re focusing on and that everyone hears every word we’ve ever said in a meeting. What’s more often the case is that we’re surrounded by people who are hearing things for the first time. This is also why I think we should be more patient with employees who are making mistakes due to synchronization issues. Many times, we’ll find it’s actually our fault.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?
My particular person would be my childhood friend, schoolmate and fellow squadron member Eran Heffetz. Eran was always a very organized person, his father was a pilot, and everyone knew he would end up as one. I, on the other hand, was not. As a son of a musician and a surfing addict, the odds of me becoming a fighter pilot were not in my favor. In Israel, more than 20,000 people start the screening process and fewer than 20 get selected. I literally had no idea what it meant to be a pilot and I never would have made it into the flight academy if it weren’t for Eran. Through the flight academy and to this day, Eran has always been a role model to me. Three more people who I can’t thank enough are Ron Chen, our third wingman who has been with Eran and me since flight academy days; Omri Dor, my brilliant younger brother and Obligo’s co-founder who introduced me to the world of technology; and Yael Dor, my beautiful wife, and the mother of our three wonderful daughters, who made all this possible.
How have you used your success to bring goodness to the world?
Honestly, I don’t think I’m doing enough. I’m mainly focused on Obligo these days and bringing positive change to renters’ lives by eliminating the need for security deposits. I am also not as successful as you might think (yet), at least not to the extent that I would be able to bring large-scale goodness into the world. I definitely want to do more, and this question is making me think about how I can do so.
You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the most amount of people, what would that be? You never know what your idea can trigger. 🙂
If I could inspire a movement, it would probably have to do with strengthening relationships between people and increasing everyone’s social ‘skin in the game.’ Today, we hide behind our phones and computers, which makes it easy to forget that people are real and that we are all in this together. As soon as I figure out how to do this, I’ll make sure to share it with your readers.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
Celebrate the small wins, big ones are rare and often disappointing.
We tend to develop expectations and imagine what it would be like to sell a company, sign a big deal or raise significant equity. But after negotiations, legal work, signing papers and waiting for all the conditions to materialize, the ‘win’ is slightly disappointing and often feels like old news. The happy moments in life are the smaller wins along the way, so make an effort to celebrate them.
Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them 🙂
I would have to choose Kelly Slater who has been my surfing idol since I was 15 years old. Still competing at 47 years old and with 11 world titles, he’s definitely my G.O.A.T.
Thank you so much for these amazing insights. This was truly uplifting.