Tail End Charlie

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Tail End Charlie

Besides learning a lot about military aviation – a subject that unashamedly excites me – Jeff is always fun to read; clear, concise and informative … that’s not a recomendation, just an acknowledgement 🙂

The ‘obvious’ seems to be: start a flying school … but, Jeff – and, you – may have other ideas. Also, work backwards: how big must a flying school be in order to generate Jeff’s required annual compound growth rate? My suspicion is that Jeff – or we – would need to come up with another angle entirely … a lot of capital … or, a unique twist: anything to make Jeff’s ‘small’ business grow BIG …

… quick!


I have to start with an explanation, give a couple of excuses, then get down to business.  You’re probably wondering “What the heck does Tail End Charlie mean?”  It’s a term relevant to military aviation and applicable to my situation of bringing up the rear on the growth engine exercise.

As best I can determine, the term has it’s origins during World War II and was used to refer to the poor sap who was the rear gunner in a bomber or the man guarding the rear of a patrol.  It has parallels in Naval Aviation where I’ve used it in reference to the last aircraft in formation or the last aircraft to land on the aircraft carrier.

The term meshes nicely with the seaboard landing scenario on an aircraft carrier.  For Naval Aviators, the term “Charlie” means that Mom (the boat) is ready to recover airplanes.  In Naval Aviation slang “Charlie” stems from the fact that Mom usually has to make a big sweeping turn into the wind so she can recover aircraft.  From the sky, the boat’s wake looks like a big letter “C,” or “Charlie” in the military phonetic alphabet.  If you’re “Tail End Charlie,” you’re the last to land.

So how did I end up as Tail End Charlie on the growth engine exercise, guarding the rear of the formation, paying homage to my fellow MITs and learning from their experiences?  A bunch of excuses is how.  I’ll save you the explanation only to say that everything else I’ve devoted my attention to this past month promises to increase my Net Worth.  So my heart was in the right place.  But I’m Tail End Charlie nonetheless.

Here’s my Diane’s Table…

Earn:  How do you make or want to make money Spend: How do I spend or want to spend money Ability: What am I good at or wish I was good at Do: Hobbies, Qualifications, things I want to do
Do or Have Earned Money By: Do or Have Spent Money On: Things I think I’m good at:
Flying Airplanes Boating Flying Airplanes Computers
Leading People and Building Teams Computers and Electronics Leading People and building Teams Home Improvements / fixing things
Teaching/Instructing Books Making Decisions Tinker with cars
Mentoring “Making Money Online” Learning Cutting to the heart of an issue or problem Conducting Financial Planning, Managing Money and Investing
By having a strong and successful family and marriage that focuses on Teamwork Cars Can simplify the complex in order to aid understanding, learning and decision making Reading
Want to make money via: Conducting Financial Planning, Managing Money and Investing Making Plans and Strategy Boating
Making money online Home Improvements / fixing things Leveraging the abilities of others Qualifications:
My own business Want to spend money on:
Viewing a situation through multiple perspectives Fly Airplanes
Passive income streams Personal Travel Seeing the Big Picture Things I like to do via work:
  Airplanes and flying Conducting Financial Planning, Managing Money and Investing Lead People and Build Teams
  Family Learning new jobs and information quickly Teach and Instruct
Speaking & Presenting
Plan, Strategize and Execute
    Home Improvements / fixing things Things I wish I did or want to do more of:
    Solving Problems Buy Real Estate
    Being a Husband and Father Make money on line
    Wish I was better at: Do more mentoring
    Meeting new people Travel with my family
    Being a better mentor  

When I step back and look at my table, several things jump out at me.  Flying, Teaching, Family and Leading/Team Building seem to be very prominent items.  Also heavily weighted are Reading/Writing, Financial Matters, Home Improvements and Making Money Online.

I’ll save you the time counting columns on my Diane’s Table.

The following items are consistent across four columns:

  • Flying and Airplanes
  • Teaching / Instructing / Learning / Mentoring
  • Family

The following items are consistent across three columns:

The Following items are consistent across two columns:

  • Cars
  • Boating
  • Computers

I have some ideas as to what all this tells me but I’ll save that for later in the dialogue that will hopefully follow below.  I don’t want to influence the discussion before the brainstorming and feedback that I hope will come from the rest of the MIT team.  Just remember my RCGR is 38% and I plan to stretch a bit and use Real Estate, Stocks, and a Small Business to overshoot my Number.

Until then, Tail End Charlie is “rollin in the groove” with the hook down, flaps full, three down and locked, ready to come aboard.

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Reader Comments

Hey Jeff, always wanted to learn to fly, so in a few years when I retire, I’ll be your customer.

my question is, if your intention is to start your own flying school, maybe you could draft some of your fighter jet buddies to come on board with you, you hold the majority of the company, and advertise that all the instructors are x-fighter pilots? This will also act to minimize your personal risk exposure.

@ Josh – I can see the fighter pilot twist. That could be an approach.

I’m personally not really “feeling” the “flight school” idea despite the obviousness of it in my table. After 20 years of military service, flight instructor pay is paltry (25-50K with several thousand hours experience), so I’m not sure how much of a draw it would be for other military aviators.

Most aviators will be making around 110K-125K/year at retirement so civilian flight instructor pay is a significant step down. However, with a pension in the area of 50K/year and flight instructor pay of 50K/year, I suppose there could be some interest. I’d just need to find the right type of person that is more intersted in flying than making a ton of money.

Thanks for the idea. I’ll add it to my bag of tricks. I still have some ideas that I want to run by everyone, but I’ll hold off on those until a few more MITs weigh in.

Thanks again, Jeff

Your chart seems very well organized. I like how it shows the consistency through the for columns. I am excited to hear about your intentions in the near future.

Man Jeff, I’m stumped on ideas for you. On one hand, you have immense and valuable leadership training, and incredible skill to be able to fly, but on the other hand, that industry in the commercial world doesn’t necessarily net you very much unless you have a super-unique business idea/niche.

@Scott – My dad thinks I should be a financial planner after the military. I have no specialized training or experience in finance nor even a business degree. Finance is more of a hobby for me.

I’m convinced that I could get a job after the military in any organization. I truly believe that Leadership is a unique skill (which can be learned) and someone who has the ability to lead can be transplanted into any organization producing any widget and be successful.

In my current job, I’m doing nothing even remotely related to flying. I’m in what is basically an acquisitions policy job for NATO. I’m in a leadership position where my followers are more senior (yes they outrank me) and have more experience (measured in years) in this discipline. But I’m effective because I recognize my limitations, leverage the experience and knowledge of my people and have built a team that desires to succeed. It doesn’t matter what the widgets are, people are pretty much the same where ever you go and leading them doesn’t appreciably change from organization to organization.

But finding another job isn’t what this MIT experiment is about, in my opinion. It’s about me (and the the rest of the MIT in their special ways) using my unique talents to start a business. So Leadership and Flying are some of my core competencies. Making things happen is a trait that I have and intend to leverage as well.

I think now is the time to spring some more of my ideas on the team now continue this discussion.

My dream job right now is to start an Air Taxi/Charter business. I know more than just how to fly. I’ve spent a fair portion of my career working in and leading Operations, Administration, Safety and Maintenance departments within a flying organization. Albeit, a military flight squadron, flight ops are flight ops. Your write a schedule, you make sure your people are trained and available and you institute an cultural environment that balances mission and safety.

For many years business aviation has been recognized for the unique benefits it provides senior leadership of the world’s companies. However, given the cost of ownership and aircraft operations, business aviation has belonged to large companies.

Today there is a new alternative that should enable a whole bunch of smaller companies to reasonably afford to charter a jet. A new category of business jet is being produced by many manufacturers (called Very Light Jets (VLJ)) that are cheap (relatively) to acquire and cheap to operate.

I want to build a business centered around the charter idea only targeting the little guys who have been too little to sit at the table of Business Aviation…until now.

So that’s one idea. The other is completely different. I can see an opportunity to build a leadership consultancy business that would help civilian companies organize, reorganize, improve work environments, build teams and improve their companies.

That’s a tall order and fairly presumptuous on my part to think that I have something over my civilian counterparts. However, I think the military afforded me (and my peers) a leadership learning experience that is dramatically different to many civilian business people.

This comment is almost a post in and of itself. Tell me what you think of my twists on my growth engine.


@ Jeff – My eyes glazed over until half-way when you discarded the J.O.B. idea 🙂 But, only because your compound growth rate probably requires it … on the other hand, you COULD aim to become CEO of Warren Buffett’s NetJets 😉 More discussion to come …

Sorry for the eye glazing. I felt the same way writing it. Another job is not what I want.

A complicating factor for me is my military service obligation which will make it difficult to go full bore after either one of these ideas for a few years.

I’d like try and use the internet (now) to begin to advance either concept in a productive (and profitable) way, then possibly transition to more of a classic bricks and mortar approach after I leave the service.

@ Jeff – In the words of Ricky Gervais (Extras and The Office – original, BBC versions): I was just “havin’ a laugh” …

We’ll have to work on the timing around all of this, because (from memory) your compound growth rate was large enough even assuming a ‘normal curve’ … now, we may have a two part curve:

1. During Military obligations – a-little-slow-and-steady as she goes

2. Post-Military obligations – super-bloody-fast, mate

Jeff, why not try to think of something the military could outsource (that is not done yet today) and build the company that can do that – using your contacts to make the contracts (sell it, that is, as a concept, then use your experience and those of your team in writing the proposals that win the business. Hopefully your core competency is something you can sell to someone else as a service, then work on selling the company off to another bigger DoD contractor.