Military To Veteran To FinTech Startup

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[Today’s military transition advice is brought to you by veteran Giff Carter of Stash.  If you’re interested in contributing your interview at, please see our posting guidelines.]

What influenced your decision to join the military, and what led to your decision to leave active duty?

Image of Giff Carter, Chief Revenue Officer of StashInvest. |

Giff Carter, Chief Revenue Officer

GIFF CARTER (GC): I’m a bit embarrassed to say, but the movie Top Gun. I joined in 1989, it was shortly after the movie came out, the Cold War was in full force and, well, it looked like it would be really cool to be a Naval Officer. I was in NROTC at college, graduated in 1993, and then was a Surface Warfare Officer for 5 years. When I got out in 1998 after a couple deployments to the Arabian Gulf, it was peacetime, the first Internet boom was in full force, and it seemed like a great time to start a new career.

Did you consider drilling with the Reserves or National Guard after active duty?

GC: Definitely, but when I left the Navy I went to graduate school and didn’t feel that I had enough control over my schedule to commit to active reserves.

How did you prepare for your transition? What was a good idea, and what was a waste of time?

GC: Before I decided to go to graduate school, I looked at taking a job straight out of the Navy. I had two real problems — basically, I was on deployment and couldn’t really interview, and I also didn’t know where I wanted to live/work. I’d grown up in the mid-West and didn’t want to go back to Cleveland, and had lived in Boston, Oakland, and Honolulu while in the Navy. This was basically pre-Internet. I didn’t really know where I wanted to live. Ultimately, going back to school solved those problems — it got me back to the mainland and into a structured environment where I could think through where I wanted to live, go to interviews, etc.
So, I did a terrible job of preparing for the transition. Looking back, understanding those key issues of where geographically you want to go, what kind of work do you want to do, do you want to go back to school — those would have been so, so helpful.

Finally, money. It was way more expensive than I planned for to fully move into civilian life. I was moving from subsidized housing in military communities into a city (Boston, it turned out) and it was so much more expensive than I had anticipated.

What military skills helped your transition, and what do you wish you’d learned before you left active duty? 

GC: The biggest things that helped me in grad school (and beyond) were time management, diligence, and attention to detail. In grad school, I was married, and I treated school as a job. I got up at 6 am every day, studied until 8 am went to school and went to class/studied until 6pm, then spent time with my wife. My classmates had a decidedly different study schedule. So I graduated number 2 in my class. That’s helped me so much. You know those quips — 80% of life is just showing up, and simply reading the document / presentation / instructions gives you a huge leap on those that don’t.

Looking back on your transition now, what would you advise your younger active-duty self? What lessons did you learn?

GC: Like I said, I did a terrible job of preparing for the transition. In retrospect, understanding key issues of where you want to go (geographically), what kind of work do you want to do (professionally) is hugely helpful. Do you want to go back to school, and finally, preparing yourself for the expenses and cost of living outside of the military. All of these decisions and considerations are incredibly useful when making the switch.

Now that you’ve been out for a while, what do you miss about the military? What do you not miss one little bit?

GC: I miss the sense of mission. While most every business has some societally beneficial mission, helping people save, buy a home, get entertainment, etc., for the most part, commercial life does not address core issues of protecting safety and society as a whole.

I don’t miss the mid-watch at all.

What advice would you give to someone who has 2-3 years left on their active-duty obligation and isn’t sure whether to stay in?

GC: Don’t get seduced by money. Between pay, reenlistment bonuses, and the huge amount of training and education Uncle Sam will pay for, the military can be a pretty good economic deal, at least to set you up for a second career. I’d focus on what you really like doing — if the mission, the excitement, the service really appeals to you, stay in. At the same time, don’t be seduced by the illusion of job security. If you don’t love being in the service, go find something you love. Lots of jobs and opportunity out there (so long as you are willing to relocate and are tech comfortable).

How did you end up at Stash? What convinced you to join the team? What’s surprised you about working at a startup?

GC: I was working for a large company, and part of my job was to look for startups that we might invest and partner with. I found Stash through two friends — one was also looking for companies to invest in, the other just started using Stash and couldn’t stop talking about it. So I met Stash and was blown away by their mission of helping regular folks, not rich people, achieve the American financial dream. We talked for a couple months, and eventually, I left the world of big companies to go help Stash help everyone. It’s way more rewarding.

Any other advice for navigating the transition and the job search?

GC: As to jobs, try to prioritize what’s important to you — job security, glamour industry, career progression, etc. But whether a big company or a small company, really try to go to a growth company. Opportunities come faster and are more valuable in growth companies.

Giff Carter is the Chief Revenue Officer of Stash, making investing and saving more accessible to the +109M Americans who are underserved by the big incumbent institutions.

Related articles:
Marine to Veteran to Entrepreneur
Making The Transition: Federal Civil Service
Reader Update: From The Military To Bridge Career To Retirement
      (Ben, this story still makes me smile every time I see it!)
The transition to a bridge career
5 Ways to Ease the Transition from Military to Civilian Career



WHAT I DO: I help you reach financial independence. For free. I retired in 2002 after 20 years in the Navy's submarine force. I wrote "The Military Guide to Financial Independence and Retirement" to share the stories of over 50 other financially independent servicemembers, veterans, and families. All of my writing revenue is donated to military-friendly charities.

  1. This is an awesome interview. I have a background in helping service members through their transition, so this really hit home. It’s so wonderful to see the lessons learned and the success story being shared with veterans. It’s this type of advice that helps others going through the transition process now. Excellent story! Thank you for sharing!

  2. Great interview and story! I agree with you that military service can be a great economic deal in setting someone up for a great and often lucrative career. I work with quite a few folks who are collecting a full military retirement and are also making six figures, and Uncle Sam paid for their degree.

    And I also agree that opportunities come fast at growth companies, but they can also fall apart faster. I worked for a small dotcom company during the boom in the mid-90’s and experienced that first hand!

    Comment? Question? What's on your mind?