From Army Officer to Silicon Valley

A case study against getting an MBA

Free Beer, Free Food, and Free Happy Hours

Last week my startup laid off 270 people due to a misguided strategic decision made by the CEO.  2019 was a year of growth for the tech world.  Investors threw money at anything with two legs, a pulse, and a quixotical idea.  Our CEO met all these criteria.  2020 ushered in a few failed IPOs and overnight, investors cut the growth money and started whispering words rarely heard in the Silicon Valley—"margins, profit, and sustainability.”  Oh my. The failure in corporate strategy trickled quickly to the tactical level.  In a matter of an hour, our data team was halved.  Those fired mourned as they were told to leave before noon, and those remaining picked up the slack.

Funny thing is, I’ve loved every moment of this roller-coaster ride into tech and data.  It has been a wild ride that I would have never predicted in a million years. Just over a year ago, I sat on the DMZ in South Korea preparing my transition from the military with a GMAT study book in hand.  As a good staff officer, I created an excel sheet to help me prepare for the transition.  I built a timeline and list of resources in the excel tabs.  Most importantly, I queried LinkedIn for veterans in dozens of careers and in a tab created a list of over 100 potential leads.  I strategically crafted and sent LinkedIn messages to these leads to ask for 15 minutes of his/her time.  And it worked. With a 92% hit rate, I am forever indebted to the veterans who entertained my stupid questions (there is a difference between “project” and “product” manager) and helped pave my path to civilian life. One of the most important things I learned was that there is no SOP— every one of the people I spoke to had a different story and conditions that led them to a successful civilian career.  At the end of each phone chat, I asked myself “how happy does this person seem and how much do I relate to this person?”  The answer to these questions steered me away from pursuing an MBA and pushed me into the ever changing world of tech.

In my search, I came across Shift.  Shift is an amazing organization that launched my career into tech and eventually data.  Shift uses the Career Skills Program to give transitioning service members the opportunity to participate in a six month internship while still active duty.  After an application process, Kate Moon and Mike Slagh brought me into the Shift framework and recreated my resume and spoke to me extensively about the transition.  They listened to my interests and helped me tailor my resume to pursue those interests. I don’t say goals, because a newly transitioned officer tends to be more clueless than a 2LT (or at least I was).  But Shift entertained my delusions and helped guide me into a role where I could truly flourish. They arranged interviews with numerous companies and helped me decide on a company for a three-month internship with the Business Intelligence team. I could not have transitioned without them.

Three reorganizations, a promotion, a giant layoff, and a year later, I am now on the data team doing everything data—engineering, science (machine learning!), analytics, etc.  Standard issue is free beer, free food (hello avocado toast), and free happy hours, but also the opportunity to grow and learn at a pace unparalleled at a big company, let alone the military.  FOMO is real sometimes, when my classmates post acceptance letters from top MBA programs on their social media.  But then I remember when they get out of their program in 2 years, they will be $150k in debt and a project manager, program if they are lucky.  Last time I checked, data engineers make much more than program managers and work a fraction of the hours.  And this incredible experience riding the tech roller-coaster in San Francisco? I would not change a thing.  

For anyone who wants to recreate my transition experiment, I recommend two things.

1)    When you talk to people, ALWAYS ask if they can make an introduction to someone else. This practice builds your network and network is key. Also ask if you should be asking any other questions. This practice gives people a chance to politely keep you on the right azimuth.

2)    Be prepared to suck a bit. Like not Sapper school suck (SLTW!) where you can just keep swimming, but real intellectual and emotional suck as you drown in an identity crisis while kids who just graduated college swim circles around you because they can git branch and you can’t (yet).  This feeling is normal and you will get through it.   

TAMU Grad, Army Officer, Commercial Real Estate Sales

So, you have made the decision to leave the military and go into, what we colloquially call, the “private sector”.  And since you are on the sitreps2steercos Instagram and blog page, you probably want to take advantage of your VA education benefits, get an MBA and do something big in Corporate America.  It is a great plan/path and it’s one many a veteran has taken before you.  But are you sure this is the right path into the private sector for you?  The purpose of this blog article is to encourage just a few of the readers to reconsider the MBA to banking/consulting route and to think about diving straight into sales. 

At this point in your career, you have decided you want to go into business and make money.  Why else do you go into business but to make money?  Side note: It will amaze you how many people lose focus of this in business.  The thing is, there is more than one way to do that in the private sector.  You don’t have to be an associate at a bank, a private equity shop or a consulting firm to make a lot of money.  Most important thing you can do before you make the plunge is to find out who you are and how you want to spend and invest your time rather than waste it.  Take a brief moment to honestly reflect and answer the following questions:

Are you a numbers person, or are you a people person?  You can be both, but as it turns out you are more one than the other.   A numbers person likes accounting, hangs out in excel spreadsheets and scores high on the Introvert/Thinking of a Myers Briggs test - numbers people tend to have a higher Intelligence Quotient (IQ). 

Sales people, as it turns out, are more relationship driven and therefore more people driven.  They tend to score higher in the emotional quotient (EQ) as opposed to IQ.  They are attuned to what people want and they figure out how to help their clients quickly and efficiently get what they want. They like picking up the phone, building relationships and view relationship building greater than transaction making. 

Did you struggle on a staff putting together that winded bullshit power point deck?  Missing the most minor of details only to be chewed out by your staff weenie boss?  If that was your Hell, you may want to consider sales.  Details matter in sales but in a very different way because the details are fleshed out in the way you read people and create relationships.  This is completely different than the technical detail-oriented issues you dealt with on staff.  

Were you really good at understanding a colleague’s point of view, empathizing with it, helping them achieve their goal so they would help you achieve your goal down the road?  Sales is something you want to consider.  It is probably a latent skill for you that you haven’t uncovered yet because you haven’t gone into the private sector up to this point in your life. 

How badly are your trying to get away from authority?  If you hated unnecessary red tape, overly invasive leaders breathing down your neck over things they shouldn’t have been worried about in the first place, you need to understand, this will still in part be a problem for you at a big corporation as a W2 employee.  No, you aren’t urinating in a cup on a monthly basis, but the command and control is still there.   The bureaucracy at a bank, in many ways, is worse than the federal government itself.

A 1099 or small business owner doesn’t have to deal with this.  The straight commission 1099 sales person is as free of a human being as there is in the private sector.  You are doing what Peter Thiel told us to do in his book “Zero to One”: 1) No brick and mortar (work out of your home or your car or someone else’s office if you franchise); 2) No employees, though eventually you will get partners and possibly staff, 3) No inventory.  If having a small property book, with few supervisors as possible, and being a lean manager is something you want, then 1099 Sales is for you.

There are, of course, tradeoffs to this lifestyle.  Since you are on 1099 status, you pay the other side of taxes and don’t withhold (your Social Security taxes go from 7.5% to 15%).  There is also no pension fund or 401(K) you are paying into which means you have to have the discipline to plan your own retirement.  So, when a recruiter tells you that you should be making $250,000.00 a year in year 2 of your business, be careful with your expectations.  Remember that that number is “income”, not salary and there is a difference.  In this case, $250,000.00 really means roughly $100,000.00 in take home pay (in a no income tax state) when accounting for your costs when starting your business, paying higher taxes and covering your retirement costs.

Still not crazy sold on sales? Doesn’t quite have the luster you are looking for?  Consider this, according to Market Watch, the vast majority of billionaires started out in sales.  This shouldn’t be a surprise to anyone, since the soft skills you learn in sales you really only learn on the job and they are the skills that help you move up the latter or start a business and follow through with it.  It may not be sexy and what you had in mind but it will get your further in life if not change it altogether. 

Bottom line, who are you?  Are you wanting to be in a large group dealing with other people’s problems, personality conflicts, etc., or do you want to operate in a lean environment where people are your business not exclusively numbers in a computer?  Do you have the discipline to be your own boss?  You need to figure out who you really are before you make this big decision you are about to make.  Do not let the Post 9-11 GI Bill distort your decision making i.e. “I must get an MBA since the VA is paying for it and leverage my ‘military leadership background’ in corporate America with my fancy degree.”  Remember, if you plan to have kids, you can pass your GI Bill off to those kids, or your spouse.  An MBA or Law Degree takes 2-5 years depending on how you execute the program and how many degrees you get.  It would be a shame to go through all of that when you didn’t need it in the first place.

Navy E-6 to Management Consultant at Accenture

I did 5 years in the Navy and made it to E-6. Got out and worked at an investment firm in the Bay Area. Now work at Accenture as a management consultant. I did a part-time MS in Finance on the weekends. Still enough GI Bill for MBA if I hate consulting.

Retired Army to Bank of America

I’m a retired 13Z5V who is now a VP Product Sales at BofA covering LATAM. I have been with the bank for almost 5 years and came through the Veterans Associate Program (VAP). 

 Most of my Army years were in the 75th RR, 82nd or 173rd. I made my transition happen because I had a good CDR and sold my plan accordingly.

 When I was a 1SG I told all of my guys that they needed to get their bachelors degree and work hard. I didn’t drink too much of the kool-aid to see my guys after years of service get screwed over during transition like I saw others get.

 The O’s always got it the worst since the peer pressure was strong by career O’s who didn’t know any better. 

I’m happy to assist in anyway I can.