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Life Update: What am I up to?
Startups, searching for a business, and four years post-army.
It just hit me the other day that I hit my 4 years post-army mark.
Do I miss it? Sure, at times.
I miss how much going to work in the army felt like going to just hang out with my friends (sometimes….not when I was in the S-3). Right now my life is very me-focused (more on that later), but I don’t have a team I work with at the moment and I work from home and I feel that lack of a team more acutely.
And yeah, I’d be lying if I said I didn’t miss the adventure aspect. I got to jump out of planes, shoot machine guns, and blow stuff up. Don’t let anyone tell you that isn’t fun.
So yes, I miss parts of it. I would go back and do it again. But I am glad I left.

My First Big Failure Post-Army
After the army, I went on to go get an MBA and the plan after graduation was to work on a startup, Vet Journey. Many of you even helped me out in the early phases of testing the platform. I had high hopes for it but ultimately decided to leave the project back in April of 2023.
It was a tough commitment to quit. People started associating me with the company and it aligned very well with The Veteran Professional and it seemed like I was very much the right guy to make this happen.
So what went wrong?
I backed myself into a corner:
After I graduated from business school, I took a job with one of my co-founders in Vet Journey. He has an existing recruiting business and offered me a job there. On paper, this seemed like a great idea. My boss would be my co-founder. I knew he would be able to give me a lot of flexibility so that I could do my day job and work on Vet Journey at the same time. The problem came when I wanted to leave that job. I now had to figure out how to navigate telling my boss I wanted to quit, but also that I wanted to stay his business partner. It was a strange dynamic that left me feeling the only way I could really quit the job without spoiling our relationship was to also quit Vet Journey.
I trusted, but didn’t verify:
That boss/partner told me his company was doing well. He made it sound like the company was flying high and I took him at his word. But when I started and got to peak behind the curtain, the reality was very different. Lesson learned: ask to see the contracts.
Have uncomfortable conversations early: When I joined the startup, I saw right away that we had some issues with how the equity was split and how we valued each team member. It didn’t make sense. But I kept punting that conversation, which just made things worse.
Overall, I’m not upset about how this venture. I did not accomplish what I set out to do, but learned a heckuva lot along the way.
Pivoting to Searching for a Business to Buy
I first heard of a search fund from Justin Nassiri’s podcast, “Beyond the Uniform,” before I left the army. I kept it in the back of my head and thought, “That might be a good option one day.”
While at business school, I focused on a startup. I knew that I wanted to give founding a new company a try. But I told myself that if the startup didn’t work out, I should take a look at buying a business.
So there I was, April 2023, newly married, a year post-graduation, and a failed startup attempt under my belt. My new wife and I talked about it and agreed to take a swing at the idea of buying a small business.
But I didn’t dive headfirst into the darkness without a flashlight. I took some effort to de-risk this plan first.
Took multiple classes at school:
I was fortunate enough to go to an MBA program with a handful of classes related to the topic of buying a small business. That helped me get familiar with the idea and processes needed.
Started part-time before going full-time:
Truth be told, I probably mentally quit my job and the startup 4-5 months before I actually did. I found myself looking at businesses in my spare time and even made an offer on one a few months before I quit. This gave me the ability to test the waters before jumping in.
Connected with people and learned:
I interviewed several people on the podcast who were in the sphere of buying businesses before I made the jump myself. (Look, I do the podcast for you all but make no mistake- I also do it to learn a lot myself). I also talked to a dozen or so investors and other business buyers who gave me the confidence to see that I could complete this act of buying a small business.
Current State
A few months ago, I got a signed offer from a business that does IT work for the federal government. Essentially, that places us into an exclusive relationship where they can’t take offers from anyone else during a defined period, but I can still look at other businesses. This also gets you more access to “peer under the hood” of the business. Most importantly, this is the critical step in getting banks and investors to start taking you seriously and dusting off their checkbooks.
While under offer, my job is to conduct my diligence on the business, finalize negotiations with the sellers, and arrange financing through a combination of a bank, investors, and the sellers. So being under a signed offer is by no means a done deal - a lot can still go wrong.
This deal….has been a journey. In the first few weeks, the Small Business Administration (SBA) changed some policies around their loan program that directly affected this deal. Then we had to find investors.
Then I was 100% sure the deal was going to close.
The next week I was 100% certain it would not.
Right now- we don’t know. There are some factors outside of anyone’s control at the moment that should shake out in the next few weeks.
All this is to say is that this process has been a roller coaster of emotions. I’m reminded of the sign outside of Ranger School:

We need that for anyone thinking of buying a small business.
The Future
Fingers crossed we get this deal across the finish line.
I then plan to zero in on running a great business and hiring a few key players to take me out of the day-to-day of the business.
Ultimately, I plan to then have the capital to invest back into other veterans seeking to start or acquire a business.
Stay tuned.
- Mark
P.S. Are you thinking of buying a business? I recommend taking a look at Acquira and its accelerator as a way to get started. They place you in a cohort with other business buyers, help you vet deals, and then help you put together the financing to close on a business. Take a look HERE and use the link to get 10% off.