My Story: The Sequel to the “Owning Unsexy Businesses” Thread

This is from Wall Street Oasis and really highlights where I am at with my own decision matrix in the “MBA/no-MBA/Leave secure job/Don’t leave job” spectrum.

“Anything worth gaining in life takes a solid brass pair.”

Hey everyone,

About six months ago I created a thread on WSO that ended up having a profound impact on my life. The thread was about owning and operating relatively “unsexy” businesses, and my goal was to pick the brain of other users to hear any thoughts or experiences they could offer (link:…).

The idea for the thread came to me after working on a couple specific sell-side deals. These companies were in relatively boring industries, yet they were generating millions for founders that seemed to have a pretty chill lifestyle (i.e., they certainly weren’t turning comments to a CIM at 3:00am). More importantly, these guys weren’t super brilliant or anything like that; in banking, you quickly realize that founders/C-level types aren’t nearly as smart as you think they should be. If they could do it, I felt like I could too.

So during a few 3:00am nights I began to realize that: a) I didn’t want to do banking forever, b) I wanted to be my own boss, and c) I wanted to start a company in one of these “unsexy” businesses that was easy to understand and offered consolidation opportunities (almost all of the unsexy success stories I had seen were basically just roll-ups). I didn’t have the faintest idea of what I actually wanted to do though, so I started the WSO thread to help jog my brain.

The thread had some great dialogue including a few ideas I had not previously thought of, in addition to a few websites for small business listings. I went to one of the listing websites and searched for businesses back in my home state (Tennessee), and after about 10 minutes stumbled on a listing that caught my eye: an established billboard company in an area of rural Tennessee that I knew very well. It was generating ~$125k in gross revenue and ~$100k in EBITDA, and was priced at ~$500k. I didn’t know the first thing about billboards until reading that listing, but I did some due diligence and shortly became convinced that this business satisfied every qualification I was looking for: passive business model, location agnostic, niche industry that most people did not understand, opportunity for consolidation, and of course high cash flow.

I ended up having a few diligence calls with the owner before deciding I wanted to go for it. I drafted a comprehensive business plan and applied for an SBA loan with 10+ banks. The process was grueling; I had always heard that SBA loans are sometimes more trouble than they were worth, and I can now attest to it. Everything moves at a snail’s pace, and the seller’s taxes were a mess so I was having to walk the loan officers through all the adjustments (it was tough to even schedule these calls during my work day). That said, SBA also provides 80% financing with 6% interest, much better than I could do on a standard commercial loan with no track record and minimal collateral. Fortunately the seller signed an LOI with exclusivity, so we went far enough down the path that an extra month or two before closing did not cause him to walk away (but he was very close!).

After about six months from start to finish, I finally was approved by the bank and closed on the deal. I have owned it for about two weeks now, and it still shocks me that I actually went through with it. There were so many opportunities to walk away: can I actually do this? will I have enough money? what if I suck? what if I go bankrupt? what if all the customers leave? what in the hell am I doing??? But at some point you need to just take the plunge, and I am proud of myself for doing it.

My current plan is to work my banking job for another 1.5 years, collect two more bonuses, than quit to move back home and work on the business full-time. I need to grow organically to reach my annual income goal, and it is hard to do that from another state (not to mention while working a grueling IB job). As cheesy as it sounds, banking helped me realize that I am a “work to live”, not “live to work” type guy, and I am looking forward to getting my free time back while making a nice income.

Sorry for the long post, this ended up being much longer than I anticipated. But I felt like I needed to post a follow up given how helpful the prior thread was for me.

If anyone has any questions, please fire away!

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