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Best business decisions Screencaps readers have made in life

Let’s not waste time today. I want to be inspired. You want to be inspired. Let’s do some inspiring.

*[Ed. note] Remember, “business decision” doesn’t necessarily mean a decision that made you a pile of money. “Business decision” can also mean things like calling off a wedding at the last minute because it was going to cost you a fortune during the eventual divorce.*

• Rick from Virginia Beach, VA writes:

Seriously enjoy this community. I’ve been entertained by you and the entire OutKick clan since the beginning of the RO RO. Thank you and all of the peeps for keeping it light, fun, educational and hilarious.

I played football at Duke (i mean Woke U) in the 80’s and upon graduating I was interviewing with the FBI, Secret Service and the ATF. It was an extremely long and exhaustive process. While I was involved in this process I was bartending/personal training and pretty much leading a life of debauchery. This was an extension of how I handled the entirety of my college years. After this 3 1/2 year interview and background check process, they figured out the real me and all three agencies passed. I was crushed but determined to throw middle fingers at the Man!

About this time I met my wife and started to get my ducks in a row. My personal training business was flourishing. But I couldn’t make money unless I was at the gym. So I had a grand idea to open up my own spot where I could have membership dues and keep up the PT as well. It took 8 years to finally get this done and we’ve been at it for 25 years now. This was the best thing that could have happened to me. I couldn’t imagine working as a government stooge, especially in this environment. The decision to open my own business and work for myself is beyond the best business decision I’ve ever made.

Thanks for all that do for the regular peeps,

• Brian writes:

8 years ago I was working at a law firm making a good living with good benefits but was not happy because I was working for someone else and a lot of other little reasons.

One night I was sitting up watching “A Bronx Tale” and Sonny explained to C that he paid his guys well but not too much because if he did they wouldn’t need him anymore. I knew at that moment he was describing my life at this law firm and I had to go out on my own.

The next morning I told my wife what I wanted to do. She told me she loved me and we’d find a way to make it, and that our 3 daughters would eat well and we would eat Raman noodles every night if we had to until I made it.

I started my own law firm with four cases and a very low-paying contract for legal work and have never looked back. I now have two law offices in two states. The lesson is simple: Bet on yourself and don’t look to anyone else for your success.

• Proud TNML member Galen in TN writes:

Without a doubt my best business decision was ENTREPRENEURSHIP. As I was coming to the end of my 30-year teaching/coaching career I knew I wanted to remain active in retirement and still make money. I read every book I could get my hands on concerning real estate investing and decided to jump into the rental property game. 

I bought the rental property “bread and butter” 3 BR/2BA brick ranch homes and, being a wannabe handyman, I was able to do many things on my own. 

Not satisfied with that, I started my own lawn care business before it became cool (talkin’ to you TNML!). I had most everything I needed already due to the rental properties and only had to purchase a zero turn SCAG. No employees were hired because I just wanted to keep it small and do all the work myself. Lots of hard work, but the profits were all mine.

Entrepreneurship allowed me the flexibility to set my own schedule of days and hours to work. If I don’t want to mow on Mondays, I don’t. Coming from a profession where every minute of every day was accounted for, the freedom that my businesses allow me is as nice as the money itself.

Now that I am 65 I have reached the holy trifecta of a Pension, Social Security, and Medicare ( “f” you lib libs because I worked for 45+ years and paid into the system…it is MY money!) Life is great and I have plenty of free time. I have my health and the ability to “Do Hard Things,” walk regularly, ride my bike, hit the gym, play pickleball, and hit the beautiful East Tennessee mountains and lakes.

I am making more money now than when I was working 60 hours a week between classroom and basketball and another 15 a week at home grading, planning, calling parents, etc. Yes, it takes a while to build. The final result is worth the sacrifices. Sadly, I think too many Americans of our wonderful USA feel entitled and it should be handed to them. Not the way to success, ‘flakes!

Thanks, Joe, for the platform to express our opinions with a like-minded group. No matter the age group, being a true American with the freedom to start your own business is a beautiful thing!

(Photo by Ronald Martinez/Getty Images)

• Jon F. from right here in NW Ohio writes:

Without a doubt… Rental properties.  During the housing crisis (2007) I bought my first rental property for $42K.  Put a little north of 12K down and had a mortgage payment of less than $450/mo. while renting it for $815/mo.   

The Toledo market was unique where the property values took a nosedive, but rents still stayed relatively level. Was able to pick up 5 more over the next 4 years and didn’t pay myself anything… put everything back into the properties for upgrades and maintenance. 

I owned 3 rental props before owning a home for myself.  As property values went up, I sold and put the profits toward better properties.  The most properties I ever owned at one time was 13 and it felt like I had no life because this was all in addition to my normal job.  Down to 5 right now and only 1 has a mortgage.

• John L. writes:

Hi Joe.  I expect you will receive a lot of interesting responses on this, especially from your LinkedIn fans.

In my case I decided that I no longer wanted to be an accountant/auditor, so I went back to MBA school full-time in the fall of 1982.  Like many of my classmates, I initially pursued investment banking–with little success.  Pivoting to commercial banking, I found a summer internship in the Midwest followed by a full time job in New York City.

Basically, I stumbled into a branch of banking called cash management, which then evolved into the field of transaction services.  This includes payments, deposit taking, international trade, supply chain finance, and securities processing, and generates tens of billions of dollars annually for the largest banks in the world.  I eventually specialized in the area of international trade.  At my last employer, while our share price tumbled below a dollar in the 2008 financial crisis, our transaction services business kept the lights on and we continued to be rewarded.

If you look up the top 50 US banks from when I graduated in 1984, less than 10 now remain–with the loss of several hundred thousand jobs.  The combination of my post-MBA career choice, some hard work, and a lot of luck resulted in an uninterrupted 37-year career that took me around the world (76 countries) and took very good care of my family.

• Kevin J. writes:

I’m sure you will hear from much more successful guys, but here’s mine- back in June 2003 I was 32 years old without a degree and working as a desktop support tech for a healthcare company. My wife was a teacher and we were trying unsuccessfully to have kids with the idea she would be a SAHM.

I decided to go back to school on an adult education program to get a degree in management and with tuition reimbursement (remember that?) and double incomes we ended up not needing any loans. By the time I finished the program in December 2004 she was almost due to deliver our first kid. I graduated on a Saturday, our first kid was born the next Wednesday, and I accepted a new position (made possible by finishing my degree) the following Monday.

That was the most life-altering 10 days of my life, and set me on course for a trajectory that has kept us comfortable though the economic ups and downs of the ensuing 18 years.

• Greg OC writes:

Best Business Decision

Leaving the W-2 Employment world to start my own Consulting business in 2018. Working remote most of the time with a few businesses and then when Covid hit assisting more clients that no longer could afford full-time employees. Purchased 2nd home in South Carolina and hired family to assist business. Now I get to see grandchildren more often and have them relocate to same area. And sneak out for Golf year round. Home Run.

Best Books – anything by Vince Flynn/Kyle Mills featuring Mitch Rapp character. Also, Brad Thor and his main star Scott Horvath.

Bands – Kansas/Yes/ELP. Also, anything Southern Rock especially Allman Bros, Lynyrd Skynyrd & Outlaws.

Keep up the great work Joe. Again, golf and cocktails on me.

• Ben B. in Huntsville, Alabama writes:

Two lucky breaks:  

1) learning at a young age (22) to work for a mom-and-pop TV station.  Good pay, rapid promotions.  Owners recognized W-O-R-K and rewarded it. 

Became a department head at 24, tee-d up my future.  I’m 50 now and working for a much larger mom-and-pop and it’s a good career in automotive.  

2) For 20 years we saved my wife’s paycheck and then went all in on real estate 7 years ago.  We didn’t dip our toe, we went in the deep end. 

No choice but to succeed, or we would do generational damage.  IT WORKED!    

Final tip: Go work for some enterprise that sells a lot of expensive products to a vast customer base.  There’s enough for you to earn a great living.  


Good stuff from everyone.

I know Kevin J. is all worried that his “best decision” wouldn’t stand up to the others, but as I told him via a personal email, this is Screencaps. This isn’t some Forbes column. I told Kevin J. that we have readers who consider buying a mower and crushing a few yards around town to be an incredible business decision (it is, BTW).

One thing you’ll 100% always see out of this column is balance. We have some big dogs floating around Screencaps and we have some of the most incredible humans who keep this country churning along like our friends in North Dakota, Bob in Oklahoma, to the military guys who’ve sent me dispatches from all around the world, etc.

What sticks out to me from these emails is how many of you bet on yourself and your work ethic. I know the popular opinion on social media is that this country is absolutely screwed once the Boomers start kicking the bucket. Then I hear from the Screencaps community and I know things will roll on with this country. Now, we just need to figure out a way to stop people across this country from shitting down their legs and slamming fentanyl into their veins, but that’s a topic for another day.

Keep the “Best Business Decisions I Ever Made” emails rolling. This is the inspirational juice that some of us need to kickstart our lives. Help your fellow man or woman with your stories.


Vortex some wings this weekend for the football games

• Mike T. passed this one to me. I need to hear from him on how the chicken wings are in France. I assume they’re terrible, but Mike T. & Cindy T. are hanging out on the French Riviera, so there might be a chef in that area who knows how to Vortex.

Speaking of the Ts, Mike wants us to know about a food item he’s crushing this week:

Socca is a French chickpea specialty. It’s had to order from what looks like pancake batter, baked in a round pan in olive oil. It’s usually baked in a pizza wood-fired pizza oven. Top with salt and pepper, savory and delicious!

Follow along with the Ts — here!

Having IG loading issues on Screencaps?

• Ryan W. is back with an update:

The fix I provided seemed to work for a bit then it stopped. Got tired of cleaning the data So I gave up and just started using Chrome browser for iOS. Once I See your morning screencaps tweet, pop over to the chrome app, open Outkick, culture, and then click the article and Blackbeards delight! Works every time. I didn’t get a Batterydaddy for Christmas but I did pick up this little beaut from Amazon for $10 last week. It is a game changer.

Would you go on a Screencaps-hosted Kentucky bourbon tour?

I’ve been throwing this around in my head ever since my Louisville-Lexington trip a couple of weeks back. Would you Bourbon Bros® be interested in a two-day summit of some sort based out of Louisville?

I’m in the exploratory stage right now, so speak up if this idea interests you.

That’s it for this final Thursday in January. Fire off those “Best Business Decision” emails and let me know if the bourbon trail would make sense.

Now go have a great day. I have at least two Zooms coming up over the next 90 minutes, so I need to get my head right.


Numbers from :

Stuff You Guys Sent In & Stuff I Like:

Written by Joe Kinsey

Joe Kinsey is the Senior Director of Content of OutKick and the editor of the Morning Screencaps column that examines a variety of stories taking place in real America.

Kinsey is also the founder of OutKick’s Thursday Night Mowing League, America’s largest virtual mowing league.

Kinsey graduated from University of Toledo.

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