Here is a recap of the evaluations according to my personal rubric:

Entrepreneurship Through Acquisition stands out as my best option.

So, what exactly is “ETA”? The University of Pennsylvania Venture Lab sums it up as “buying and growing an existing small business that has already demonstrated product-market fit.”

OK, that seems simple enough. I’ll buy a business that is already successful and has ongoing operations with the goal of growing it.

To do this, I’ll take on a large loan in order to purchase the business and be living under the weight of that large debt until it is paid off.

“Wait - I thought debt was bad; wouldn’t it be better if I start a company and bootstrap it into the next Facebook?”

Go for it! However, most people know that very few startups actually survive and thrive, and the odds that your new company will be the next Facebook or Google are incredibly slim. Personally, I’d be content with a successful business that no one has ever heard of (as long as it provides a good product to its customers and a good quality of life to its employees and owner).

Let’s get back to the debt. Yes, personal debt is generally bad because that tends to be debt against depreciating assets (boat, car, Gucci purse, etc.); however, business debt is the lifeblood of the economy. When the Federal Reserve raises interest rates, their goal is to “slow down” the economy. This basically means that they will slow the amount of debt capital available for businesses to grow by making it more expensive.

Let’s look at a simple equation then:

Net Income - Debt Service = Net Profit

If Net Income ≥ Debt Service, you are winning!

OK, so debt might be OK, but how do I even get started.

1. Self-evaluation: What most resources and experienced ETA people will tell you is to start by taking an inventory of your personal skills. This will help you to find a business opportunity where you can add value simply by being part of the team.

2. Personal financial statement: If you are going to take on debt to acquire a business, you need to get a full view of your personal balance sheet. How much cash (or cash equivalents) do you have on hand? Do you have a lot of outstanding debt? What is your net worth?

3. Target statement: Some experts will have a different name for this, but after you have figured out what you’re good at and how much money you have to deploy, figure out what type of business you want to purchase. Is there a specific industry? Is there a geographical requirement? Do you have a revenue or earnings requirement?

4. Go find it: It might be tempting to simply go onto bizbuysell.com and start into it. Many experts will discourage you from this. The thinking is that only the “garbage” ends up on bizbuysell; most business brokers have relationships with and lists of people they have actually met and know can close a deal. It makes sense and it reinforces that relationships and networking are key. Most brokers will sell their best listings before it even hits a big listing site like bizbuysell. That means, you need to pick up the phone and call business brokers in your target geography or industry to introduce yourself, make sure you tell them what you’re looking for, that you have the money (getting pre-qual’d at a bank can actually provide you a proof of funds), and are serious about closing. I did this and forged some relationships, it was not hard. That being said, I found occasionally browsing bizbuysell somewhat eyeopening. You may not find the best opportunity posted publicly on bizbuysell, but browsing the listings and contacting brokers accomplished two things: 1. I actually later followed up with some of the brokers and forged relationships and 2. It gives you a great view into the economics of small businesses and can actually open your eyes to previously unknown (to you) opportunities that might be a good fit for you.

I won’t go more into why or how ETA can be a great path into business ownership or how to do it, but I’ll link to some resources that I used below.

Read more about ETA’s advantages:

• Buy Then Build by Walker Deibel, great book

• ”Harvard Business Review: Buying Your Way into Entrepreneurship,” very solid article,

• HBR Guide to Buying a Small Business this expands upon the article above

• Business Wealth without Risk by Roland Frasier, a bit sensationalized, but some good info and ideas

For “non-traditional” businesses (mainly digital in nature), these are some good brokerage sites to tap into:

• Acquire.com

• QuietLight.com

• EmpireFlippers.com

If anyone has any tips or other resources to share, feel free to post them in the comments below.

Working in Media Production (as I do), a large portion of the workforce works on a contract basis as a freelancer. This is an obvious route I could take to jump off the ladder and “be my own boss.”

But before jumping at the most obvious solution, I wanted to create a rubric to help me evaluate opportunities and how they might help me reach my goals.

The Rubric

Level of Personal Difficulty
Early on, I knew I had to try to evaluate what unique skills and experiences I had that would help me in my next…whatever is next. So, I did that. I took some time to comb back through my life and résumé to see what I’ve been able to do well and what skills I now have. This grade tries to evaluate how hard an opportunity would be for me to execute, when taking into account my skills, strengths, and experiences.

Is it interesting?
This is kind of self explanatory. Ralph Waldo Emerson said, “Nothing great was ever achieved without enthusiasm.”

What can $100k buy me?
No, I’m not trying to see if I can afford a maxed out Rivian R1S. I have around $100k that I am able to deploy in some manner to help me into what’s next; so what does that $100k buy me towards my cash flow goals?

Competitive Landscape
This is a stab at reading how hard it will be to succeed in a certain opportunity when taking into account various market dynamics.

Does this grow into long-term wealth?
I don’t want to have to work forever, I want to build a nest egg (ahem, quickly) that can sustain my family and our quality of life well into the future. Does this opportunity appreciate in value or simply provide cash flow?

Does this immediately replace my income?
This is kind of the linchpin. I’m ready to leap off the ladder, but if I don’t have a similar income ready to go, that is an issue.

OK, so now that I have my rubric, how does Freelance Media Production look?

Level of Personal Difficulty
Media Production is what I have done for 20 years, this would not be too difficult.

Is it interesting?
I love the adrenaline rush of Live Media Production and still find it interesting.

What can $100k buy me?
$100k can’t really buy me any level of cash flow with this opportunity, just runway to build a clientele.

Competitive Landscape
The landscape has definitely become more competitive and the use of AI will be a gamechanger, but I have specialized, in-demand skills and beaucoup experience.

Does this grow into long-term wealth?
No.

Does this immediately replace my income?
Yes*, after a period of time to build up my book, this would replace my income. I estimate it would take about 10-12 months.

OK. Freelance Media Production checks some boxes but, I’m not sure jumping off the ladder into this is worth it.

Residential Real Estate Investing
I have a small amount of experience and plenty of connections in Residential Real Estate Investing. This is obviously a broad category; anything from wholesaling house deals, fixing and flipping, or buying and holding rentals kind of fits in here. What does the rubric say?

Level of Personal Difficulty
I think this would be somewhat difficult for me; I’m not a seasoned “dealmaker.”

Is it interesting?
Maybe. Too hard to tell.

What can $100k buy me?
It depends, am I fixing and flipping, buying and holding, using leverage (obviously, yes)? I don’t think $100k helps me check the final box (see below), and that is potentially the most important.

Competitive Landscape
I think everybody and their brother, cousin, and dog “does” (or has done) Residential Real Estate Investing at some level. The interest rate environment makes a lot of this a bit more difficult (and I’m sure many have dropped out of the market due to that).

Does this grow into long-term wealth?
Yes, this is an excellent way to grow long-term wealth. Even dumb people can do it:

Does this immediately replace my income?
Maybe. Again, there are too many unknowns at this point and I’m not sure now is the best time to enter this market.

OK. Residential Real Estate Investing checks a few more boxes, but it is still no shoe-in.

Self Storage Acquisition
Self Storage is a sub-asset class of Commercial Real Estate. It has been on my radar as an investment for many years. The economics of Self Storage are simple: you own a piece of real estate for cost X, then you rent out many slices of that real estate for a fraction of X. The beauty is you are only providing minimal infrastructure (as compared to Multifamily), you really just provide a steel box on concrete.

OK, it is technically an operating business so it is a bit more complex than that makes it out to be. But nonetheless, it does have a few factors that make it very attractive:

• Stickiness - People hate moving their stuff; per industry expert, Scott Meyers, the average stay in a storage unit is 2.5 years.

• Valuation - Commercial Real Estate uses a cap rate to value property (not solely comps) and this can really help you juice appreciation of the asset.

• Simple business model

• No toilets, tenants, or trash

Self Storage has a lot going for it, let’s see how it rates:

Level of Personal Difficulty
Again, I think this would be somewhat difficult for me; I’m not a seasoned “dealmaker.” Additionally, I’m even less familiar with the world of CRE than I am with Residential Real Estate.

Is it interesting?
Maybe. The business is dead simple and can be formulaic, which I actually don’t mind.

What can $100k buy me?
You can get an SBA loan to purchase Self Storage at a 90% LTV. That means my $100k can purchase me a $1M Self Storage property. If we assume a cap rate of 5%, that means our NOI is $50k (before debt servicing). That is simplistic, but it definitely shows the difficulty of getting enough cash flow for the final box (see below) in the rubric.

Competitive Landscape
Self Storage has been a super hot asset class over the past decade. It is still a very fragmented market with a lot of “mom and pop” operators serving as acquisition targets. This has brought a lot more money to the market and increased competition for acquirers (or would be acquirers). Additionally, market dynamics have caused a bit of turbulence of late. Interest rates are high and storage rates are down, this makes any levered acquisition very hard to cash flow.

Does this grow into long-term wealth?
Absolutely, this is one thing that originally attracted me to this opportunity. There is a big chance that a person could do “one and done” - meaning “flipping” one Self Storage property could net over $1M in profit and leave you “set for life” (I guess this really depends on your spending patterns).

Does this immediately replace my income?
The difficulty of acquiring a property that cash flows at all right now (let alone enough for income replacement) makes this doubtful.

Entrepreneurship Through Acquisition

What is Entrepreneurship Through Acquisition? This is buying a successful, operating business and continuing to run and grow its existing operations. Harvard Business Review has a good article that provides more detail.

Let’s see how this stacks up:

*Note: a lot of the answers below are highly dependent on what type of business you plan to acquire - target wisely.

Level of Personal Difficulty
I’ve worked on technical projects, managed teams, and worked with vendors and high-level stakeholders. This would be somewhat hard for me, but I have well-rounded experience.

Is it interesting?
Running any sort of business will bring all sorts of surprises, it would be interesting in the sense that it keeps me on my toes.

What can $100k buy me?
You can get an SBA 7(a) loan at 90% LTV for acquiring a small business. That means my $100k can purchase me a $1M operating business. Now, valuation of operating business is much more opaque, but a common multiple to start with would be 3x SDE/EBITDA (that is basically how much profit a business generates before debt service). If we assume 3x SDE/EBITDA at a $1M valuation, that gets us $333k in profit (before debt service) on an annual basis.

Competitive Landscape
This is highly dependent on what sector the business operates in, but there is a wealth of acquisition targets currently as many business owners (baby boomers) are retiring.

Does this grow into long-term wealth?
Yes, although the 3x multiple does not grow your value as quickly as a CRE cap rate, you can still grow a business that you could later sell at a higher valuation (creating long-term wealth).

Does this immediately replace my income?
Yes! (finally)

OK! Only one of the opportunities on my list checks all the boxes - Entrepreneurship Through Acquisition. But, what exactly does that mean? How do I acquire a business? What types of businesses should I look at buying? Where can I find one? How does the process work?

I understand that I simplified a lot of items in this post for brevity’s sake. I’m simply documenting my journey and thought process - this is not meant to be an exhaustive guide. Thank you for understanding!

A lot of people have midlife crises.

Maybe I would want to buy a midlife crisis car, but this author has some requisite criteria to buy a midlife crisis car that I don’t meet yet. That’s ok, I’m not really a car guy.

Professional Life

I graduated college in 2005 and began working in television in Los Angeles, CA. I started out in a gear rental warehouse, began also working in the field, and then exclusively worked in the field. I worked as a tape operator (remember tapes), utility, camera operator, and eventually Engineer-in-Charge.

Working in freelance television was fun and exciting! I would work 5-10 days a month at a different location with a different challenge almost every working day. I would earn enough to fund my next world adventure to either South America, Europe, Asia, or Iowa. (Just kidding, I’ve not been to Iowa.)

After about 4 years as a freelancer in LA, I got married. I realized I was not earning enough to raise a family and decided to seek something more stable.

I landed a corporate job as a Video Producer (I was actually a preditor) and relocated to Chicago, IL with my amazing bride.

I was suddenly making steady money, we had good health insurance, and even a 401(k). I began slowly climbing the corporate ladder; I received raises about every year and I received a promotion here and there.

It was comfortable. Not quite golden handcuffs, maybe bronzed handcuffs.

Fast forward 14 years and I’m still working for the same company. My wife and I now have 2 kids and are in a beautiful home that this job made possible.

I enjoy my job, it has been good to me. I’m very thankful for the providential path God has woven for me. However, I continue to trade my time for money and when I or the employer decide to end the relationship (perhaps abruptly), that will be it.

Handcuffs Eventually Chafe

Back to the midlife crisis.

I’m not sure if I actually have a midlife crisis, but I have had a sense of restlessness and uneasiness for the past year or so.

I realized that my kids are getting older and I only have them at home for 6 and 9 more years (and they may partially “disengage” sooner than that). I also realized that I had my identity wrapped up in my job. I felt eternally attached to my job and wondered what would happen if I ever was not doing it.

In 2021, I proposed to demote myself from department Director to a specifically-skilled individual contributor role. I was tired of the corporate middle-manager rigmarole and I wanted to move into a role that would allow me to work remotely from North Carolina (near extended family). I continued to perform my new job duties from my home office with excellence and was traveling about 4 times a year.

In early 2023, about 40% of my responsibility was taken from me by a power grab from another department. I had never failed in those responsibilities and had constantly raised the bar in those productions - but still, I was “quiet fired.” (I still get some schadenfreude by seeing the new “owner” of those responsibilities continue to flounder.)

Some might think that losing 40% of their job responsibility (with no corresponding cut in pay) sounds awesome, but I took it as an affront to my abilities, expertise, and identity.

That was the hair that broke the camel’s back. I realized that I no longer wanted my financial future, my family’s quality of life, and my identity controlled by corporate managers. I was ready to break free from not just my current bronzed handcuffs, but any handcuffs that I might attain through corporate America.

I started a rough escape plan.

The Escape Plan(-ish)

Before you start any new project or venture, make sure you define:

1. What you’re trying to accomplish

2. When do you want to accomplish it

3. How you will accomplish it

I took a Friday morning in February 2023 and went to the local Biscuitville for a big, long breakfast. I brought a notebook and pen and set my phone to do not disturb.

I had way too many carbs and way too much coffee, but I did a lot of reflection and came up with the first 2 steps above.

Our names are blurred out, but the numbers to the right are the ages of my wife and I and of our children.

Starting from the bottom, my first goal (for February 2025) was to be earning $120k/year (pretax) and only be working “school hours.”

This seemed attainable and seemed like it would allow me to live the lifestyle and spend the time with my family that I wanted.

The next goal (for February 2028) is to be earning $200k/year (pretax) and maintain my same “school hours” schedule.

The final goal (for February 2033) is to be earning $300k/year (pretax) and maintain my same “school hours” schedule.

You’ll see some important ancillary goals at 10 years to make sure that my kids will not have to go into debt for university (if they attend).

These goals and milestones would mean a secure financial future (and quality of life) for my family.

Just Do It!

OK. Now I have a plan of what I want and when, but the hard part remains - how.