What Being an Army Helicopter Pilot Taught Me About Being An Entrepreneur

Every Veteran’s Day, I am reminded of the decade I spent in the military and the immeasurable impact it has had on me as an entrepreneur. Beyond the genuine camaraderie, black & white mission success criteria and a certain tempo that exists among military members, there were many lessons I learned that find their way into my daily life as a technology focused  entrepreneur, co-founder of a startup accelerator and innovation partner to large companies. Here are a few of the most important lessons learned:

  1. Don’t confuse effort for execution. Plain and simple, it’s all about results. No military objective was ever won by just trying hard and having good intentions. Mission success depends on “good enough” execution to achieve its objectives. Notice I did not say perfect execution. While perfection is a great benchmark to strive for, the reality is that a win is a win, and a mission accomplished is just that. A good effort isn’t enough and if that is your ultimate measuring stick, then be prepared for failure because you came up short. As Viper said in Top Gun, “there are no points for second place.”
  2. A good plan seldom survives first contact. In the world of an entrepreneur, this means that a well-developed business plan doesn’t usually hold completely firm when it’s implemented. Product – market fit, customer feedback, employee related issues and even funding challenges can wreak havoc on the best laid plans. The reality is that you have to be prepared to adapt, improvise and overcome adversity if you are going to be a successful startup. As an entrepreneur, your job isn’t to follow your well written plan without deviation; it is about finding a way to make your startup profitable, sustainable and ultimately worth more than the total dollars invested. It’s more about the planning process than following the exact written plan. Be prepared for the plan to change while the goal stays the same. Plan your work but be prepared to work your plan.
  3. Always fly the aircraft. As a helicopter pilot, you learn funny helicopter related jokes, sayings and insights that make you realize that many things can go wrong quickly. You learn what a Jesus nut is (the nut that holds your rotor blade to your mast, and if it comes off you will be meeting your maker). You learn what the “golden BB” is, which is the one random, one in a million lucky shot that kills you that you simply can’t avoid. You embrace that a helicopter turns “jet fuel into noise” and you don’t really fly a helicopter, but you beat the air into submission. All of these sayings make you realize, however, that no matter what the circumstance or how dicey a mission can become, you always have to continue to fly the aircraft. If a segment light comes on indicating an engine fire and you end up becoming fixated on this problem, you can take a bad situation and make it much worse. No matter how stressful things can become in the life cycle of a startup, you must continue to manage effectively to have time to resolve your issues. Don’t ever stop flying the aircraft.
  4. Don’t confuse age, rank, expertise and authority.  As a young pilot I was gung-ho, ready for action and well aware of my rank, especially when flying senior officers. When you run a startup, you often find yourself surrounded by young people. Everyone has to be some age, and you should not assume that just because your team members are young (assuming you are older than they are) that they don’t have the knowledge or skills. (By the way, this applies in reverse too). Rank is important to understand who makes decisions. Be in charge relative to your rank and be prepared to make decisions when needed while living with the decisions of others. Respect the rank but not at the expense of throwing common sense or lawful orders out the window. Expertise is a funny animal. In the military, you can be young with low rank and possess a tremendous technical expertise or specialized skill that demands respect. Listen to people who possess technical expertise and look beyond the age or rank that it may come from. Lastly, understand authority can be situational but must be respected when applicable. When someone steps aboard my aircraft, I am in charge of everything that ultimately happens on it. It doesn’t matter what rank someone wears or any other factor. If I am the pilot in command, you will do as I ask while we are flying, because your life (or the lives of others) may depend on it. If the person on board the aircraft doesn’t like it, they can take it up with me when we land. My authority extends from wheels up to wheels down safely, and after that it is back to following orders based on rank. Be sure to listen, respect and pay attention to the right people at the right time without letting certain labels or attributes get in the way.
  5. Have a Plan B in your hip pocket. As a helicopter pilot, I often would joke that you take off expecting to crash. Unfortunately there is some truth to this saying. Even on the nicest flying days (“clear blue and 22” means clear skies with 22,000 foot ceilings, 22 mile visibility) that seemingly nothing could go wrong, I am looking for a place to “crash land” as soon as we take off. My situational awareness makes note of power lines (that can ruin your day if you are heading to the ground in a forced landing), wind direction (it is always preferred to land into the wind, and depending on the wind speed, sometimes a necessity) and flat level ground that can withstand a hard landing so as not land then roll your aircraft. I take off with Plan B in my hip pocket, and as an entrepreneur I am always thinking about the five things can go wrong on the way to the one thing that we are trying to get right. Effective risk management means having a Plan B, and maybe even a Plan C, D and E too.
  6. You must have positive transfer of (flight) controls. Flying a helicopter requires tremendous aircrew coordination and being able to pass control of the aircraft back and forth between two pilots as needed. Depending on the type of aircraft (traditional side by side seating or tandem front-back seating), the mission conditions (night vision goggles vs. daytime) and the mission profile (low level high speed or leisurely cross country higher altitude), there are times when the transfer of controls must happen seamlessly, flawlessly and with little extraneous chatter or verification. The best way to accomplish this is through a three-stage hand-off procedure that goes something like this: Pilot A – “You have the controls”, Pilot B – “I have the controls”, Pilot A – “You have the controls”. This is an especially useful drill for entrepreneurs and startups in the eras of high speed information transfer, remote teamwork and information passed via electronic means. Being able to pass info quickly, absolutely and predictably means confirming information received and understood upon receipt, followed by the sender acknowledges that you have received it. This positive transfer of information is crucial to long term success and avoiding communication failures that can derail the best plans by the best teams of entrepreneurs.
  7. Take care of your people. If this means eating last, staying up a bit later to make sure your team returns from its mission or you spot check basic housing conditions to makes sure your team and their families are ok, then so be it. Take care of your team and your team should be prepared to execute against the mission. Taking care of your people is a 24/7 all the time requirement. Be aware, however, that you must also take care of yourself too, otherwise you will be no good to lead your team to success or contribute based on your expertise.
  8. Be prepared to make decisions with only 80% of the facts in. The remaining 20% seldom provides any real insight to make a substantially better decision, but taking action once you have made a decision can be the best way to bridge this gap and gain an advantage based on situational learned knowledge, feedback from customers or just being able to fine tune as needed. And also remember that “boots on the ground” knowledge is sometimes more important than theories or stale knowledge from the rear. Having boots on the ground allows real time intelligence to advice the commander (CEO) of what really is going on, and how to adpat strategy and tactics to accomplish the mission. 80% of the facts allows you to take action. By the way…you will NEVER have 100% of the facts so embrace this.
  9. Remain calm. When things start going wrong, it is easy to come unwound and lose control. If you happen to be flying a helicopter when things go wrong, losing your cool can make all the difference between flying your way out of a bad situation versus “balling up” your aircraft because you cracked under pressure. The worst times often require the coolest heads to prevail. Be sure to remain calm when things get bad, so you can keep control and live to “play another day.”
  10. Remember that teams win. Share credit where credit is due and know that teams working together can allow ordinary people to accomplish extraordinary things. Teamwork (and the attitude of the team”) can allow superior results to be achieved by a numerically inferior force. Think about the Navy SEALS and other small units (aircrews) that rely on superior teamwork, training and agility to get the job done. “An army of ten well led will beat an army of one hundred without a head.” Work as a team and recognize the talent on your team. Winning requires operational harmony of your team members, cross training for redundancy and an understanding of the mission at an individual contribution level.

These are just a few of the lessons learned from my time in the Army as a helicopter pilot that have served me well as an entrepreneur. Having flown everything from special operations support to high angle search and rescue, I can tell you that my lessons learned in the cockpit or in service to my country have shaped me to make me a better entrepreneur.  Good luck on your own entrepreneurial journey and your mission to make your startup venture a success.



About Herb Sih

Herb Sih is Managing Partner for Think Big Partners, an innovation-driven firm focused on advising the world's most progressive-minded cities, companies and entrepreneurs. Herb has a deep background in advising entrepreneurs and high growth companies, accelerating innovation and helping communities solve complex problems by building smart cities and connected technologies using human-centered design principles.


  • Ekpoole516@gmail.com' Erik Poole says:

    I happened upon your article after reiterating that old phrase of “clear, blue & 22 to a friend. I enjoyed your insightful article regarding the similarities of business and flying in the military. I share in both of those career paths and found myself fondly remembering your examples of crew coordination and how it lends itself to the civilian workplace.

  • Mr. Herb Sih,
    Thank you for this article.
    Thank you for your service.
    Much respect and honor to you and our forces that allows me; a civilian who has never been near a battle field, but who enjoys all of the benefits that you and our military have secured for more than two centuries.
    I am happily married to my H.S. sweetheart, raised 8 kids, worked several successful careers and then became a Pastor, all of it in safety, security and blessing. This would be impossible without your service and sacrifice.
    My father-in-law, Retired Army Staff Sergeant Duane Ralph Roberts served more than 20 years in military service including tours in Korea and four tours in Vietnam 282nd Assault Helicopter Co. flying Bell AH-1 Cobras.
    His handle was King Cobra.
    Most likely I will never meet you and I do not know if you will ever even read this note, seeing that your article is from 2014. However I must give honor where it is due, and I may not pass this way again. Please accept my humble thank you for the life that I have been able to lead because of you and so many others that I do not know; yet stood in the gap between the enemy and my family and our great and wonderful nation.
    God bless you richly,
    Marquis Wilson
    A citizen of these, our extraordinary United States.

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