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After I figured the small mom and pop bug companies weren’t for me, I applied to a few larger Ag (Dow, Bayer, Syngenta, BASF) companies for a sales job. I also applied to a few larger pest control companies like Terminix (who was owned by Servicemaster at the time). Honestly, Terminix was the first to call me back. They even flew me down to Tampa from Jacksonville for the interview. At 24, I was on top of the world getting to fly somewhere for a job interview. I got the job as a young “BMT” aka Branch Manager Trainee. I was so proud of my accomplishment! After they told me I was hired, they flew me up to Memphis (Servicemaster’s HQ) for my initial training for a week. The thoughts that went through my head were, let’s just say quite lofty. Dreams of ascending the corporate ladder, making tons of money, being well known and respected to everyone at the company, being President of Servicemaster! At 24, I thought I was going to rule the world. I am sure you remember your first “I’ve made it” job from your early to mid 20’s.

Well, unfortunately as I mentioned in some early newsletters, it was more like a crash and burn in my corporate career. 25 years of ups and down, promotions followed by demotions, followed by me finally throwing my keys on the desk at 47 and never looking back.

Back to that house I bought. That home was a small condo in a development called “The Brooks” in Bonita Springs, FL. On the corner was a big cow pasture which has since been turned into a huge outdoor mall. Coconut Point Mall to be exact. Long story short (read the earlier newsletters for a more detailed overview of how this unfolded), this condo was initially meant for me to live in. Then something weird happened. I have always liked reading about Real Estate. I subscribed to the Naples Daily Newspaper weekend edition and each weekend would spend hours looking at the multi million dollar beach front homes for sale in Bonita Springs and Naples. I’d drive down the road and see these huge houses and think “One day!” Again, the lofty dreams of a 25 year old.

Scrolling through the newspaper I came across the rental sections and I noticed condos in MY DEVELOPMENT that were listed for rent for $5,000/month. Exact same model as mine. My mortgage payment was only $1,200 and I thought “How are they getting that much for rent?!?”. Then I learned about the snowbirds. Retirees from up north who come down to South Florida for a few months to escape the cold. The midwestern folks follow I-75 down to Southwest FL. The northeasterners follow I-95 down and end up in Southeast FL. Yes there is some crisscrossing, but for the majority of old folks from up north, that’s the route they follow. I decided to try to rent my place out. I got it tidy, took some pics with my digital camera, uploaded them to some vacation website called VacationRentalsbyOwner.com. Back in the late 1990’s, you literally would type all of that out to get to the site. Even though the founder secured the domain of VRBO in 1995, no one knew what that acronym meant back then. So the main site was reached by typing the entire thing out. Oh, and we had to get paper checks mailed to us for the vacation rental booking.

Long story short, I moved out of my $1,200/month mortgage condo from November-April, rented a room from a friend of mine for $300/month and rented my condo out to the snowbirds for $4,000-$6,000/month depending on the month. From my recollection January and February brought in the most dough back then.

That was my first run at real estate and I was hooked. So I did what every smart real estate investor did back then…I went and levered up, bought a couple more properties over the next few years and nearly went bankrupt during the 2008 collapse. I told myself I would never touch real estate investing again. But, here we are and I now own a sizeable amount of land in East TN. How I got here is discussed in some recent newsletters and I don’t want to be redundant to older subscribers but to say the journey has been more of a rocky, treacherous crawl versus a straight up rocketship would be an understatement.

This leads me to the place I am now. Building a retreat center in one of the coolest little spots in the Southeast that I have found. It reminds me of what the Appalachian Mountains were like hundreds of years ago. Natural, views for miles, sleeping outside with a full view of the milky way passing from one side of the sky to the other, wildlife and just miles and miles of mountain range to explore

I stumbled upon the first piece of land in early 2020. I had started buying some property in Pigeon Forge as an investment after taking a break from real estate for over a decade. That itch really never went away. Even during my 12 year hiatus from real estate I would always look at real estate listings, calculate investment potential in my head, but then just bury those thought in the dungeon of my mind, locking them away, never to see the light of day with action. After I bought my first cabin in early 2020, my realtor presented me with an “opportunity”, even though it wasn’t in the heart of Pigeon Forge or Gatlinburg. From a Short Term Rental investment standpoint, I talked to a few people I met on some Facebook Smoky Mountain STR Investor groups and nearly everyone said “Don’t buy there…it’s too far away, no renters will want to stay there if visiting Gatlinburg or Pigeon Forge”. I called my realtor and said, “I’m not sure but I would still like to go take a look at it.” I visited the cabin and fell in love. I had never seen anything like it. The views, the seclusion, the drive to get to it. I didn’t care what any of the hard core investors thought, I was buying it.

It was a basic cabin, run of the mill, 1,800 square feet, 4 Bedroom, 3 Bathroom. But man…the views. You could see mountains for miles and miles, in both directions and behind you. It was a complete 360 degree mountain view from around the cabin. Everyone told me not to buy it, but after visiting it in person, I couldn’t NOT buy it. I had to have this place. The asking price was $325,000. I offered $320,000 and they took it. House and 16 acres of land with pure seclusion. All the Airbnb gurus in the Facebook groups said it was too far away from all the action in Gatlinburg but I didn’t care. I honestly didn’t care if it rented at all. I just wanted it for myself and to sit on the back deck to enjoy the breathtaking beauty of what I saw.

Looking back, I could never have imagined this place would become the epicenter of my legacy. My life’s work. The thing I want to pass down to my kids and hopefully they pass down to theirs. So what’s the address of this place and how do you book it and why do I love this county? Some of you have waited 3 years for this reveal after seeing the pictures I post on X and all the adventures you see of Jimmy and me. So, what’s my real name and how do you book the cabin I am always posting pics from? Well without further ado:

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Sometimes in my financial ventures, when I have chased the “anomaly”, it’s come back to bite me. Whether it was in the stock market or crypto space, real estate ventures, or inventory for Amazon, I’ve had some serious flops. I would imagine we all have. I’d learn my lessons, lick my wounds and I’d move on to the next venture. One thing I never did though: I never quit looking for that next diamond in the rough. They are out there and often times, when the right one presents itself, you just need to have the guts to jump in head first.

From a return standpoint, my best real estate purchase was the biggest anomaly I ever embarked upon. It went completely against the norms of the area that I was investing in (Pigeon Forge and Gatlinburg, TN, which is an area people visit and usually want to rent a cabin). The house I was buying was NOT a cabin. But deep inside I knew it was going to be a good investment. I just didn’t realize at the time how good. My wife even told me “Don’t buy this! This is the ugliest place ever. It’s not a cabin, it looks horrible, this is not going to rent.” I told her to pipe down. I’m kidding of course, but I did tell her “I know what I am doing, I’ve been investing in real estate for 25 years, sit back and watch me operate”.

For all practical purposes, I bought what looked like a white double wide trailer on a basement foundation on 1/3 of an acre. I ended up making almost $700,000 on the flip in a little over 22 months. I paid roughly $200,000 for it and sold it for nearly $1,000,000 22 months later. Initially, everyone I talked to told me it was not a good idea to buy it. “There were plenty of normal cabins in the Smoky Mountains that I could buy, why buy a vinyl siding house that has no curb appeal?” they would say. Below is the actual address of the property, photos of the renovation and the story of how my “anomaly” of a purchase all played out. Sometimes you MUST think outside of the box.

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Now that things are off and running with the retreat center, I’ll be able to devote more time to showing the numbers of my rentals (the good and bad), how the Amazon business is doing, where I am parking my excess cash nowadays and other nuances of my finances.

With that in mind, I wanted to do a quick update of how the returns are for my recent cabin that I built on my own. I did a deep dive in my prior newsletters of how much it cost to actually build a cabin. I have also shown how idiotic it is to buy an existing house in order to AirBnb it in the current market of high appreciation + high rates. Will my thoughts on this ever change? Maybe. If rates drop significantly or prices correct in certain vacation markets, it might be worth a second look. But right now, it is EXTREMELY DIFFICULT to make any short term rental investment pencil out. I don’t what the Airbnb “Gurus” are telling you. If they are telling you anything other than “Be Careful out there”, they are full of it. The worst place you can find yourself financially is an upside down Airbnb with the inability to unload it. I am already seeing that time and time again in the Smoky Mountains.

Some people who jumped on the train in 2022, 2023 and 2024 are already feeling the pinch. In the Smoky Mountains and surrounding areas, basic cabins are not doing well at all. Cabins with some amenities (game rooms, movie theater room, firepit gathering area) are doing okay. Cabins with great amenities (Indoor or outdoor pool, indoor full sized golf simulators, pickleball, massive game room set ups, sauna, cold plunge, etc) are doing and will continue to do well.

Do you see the key here? It’s not rocket science. You MUST separate yourself from the competition if you choose to ever embark on the Airbnb journey. Those who do will have good returns, those who don’t will find themselves wandering towards the destination of financial collapse. Make no mistake, a bad investment in real estate IS NOT like a bad investment in stock or crypto. With a bad real estate deal, not only do you lose your capital and investment, you lose your ability to buy pretty much anything on credit for around 5-7 years. I learned that lesson the hard way in 2008.

As I mentioned in the last write up, my latest new build cost $673,000 to build. It will sell for $1.3-$1.5 million. Great returns, but I now hold my new builds for at least a year before I sell them. Here is the actual rental link to my latest new build and the reasons why I hold them now instead of selling them immediately:

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“Hope is not a strategy”

I heard that little line for the first time when I was in my mid 30’s from the President of the company I was employed by. I spent most of my professional career there and it is the pest control giant that nearly everyone in the US has heard of. The Big O. I was in a meeting of operation manager’s. Guys who drove sales, profits and micro managed P&L’s. At the time, I was in the Entomology role for the Southeast US. I’d support local branches, train technicians on chemical applications and the various products we would use, go out to large commercial accounts who had major bug issues, etc.

The individual who triggered that response from the President managed the state of Florida for the company. He had 25-30 pest control offices in Florida reporting to him and a Hurricane had just blown through a large swath of the state. A quick crash course in the bug business: Pest Control is divided into two categories. Residential and Commercial. Within those categories there many other subsets like Termite Control, Bed Bug Control, Crawlspace encapsulation work, etc. The residential side is a door to door, “close the deal at the kitchen table”, type of business. Granted, as big as the company I worked for was, they got lots of inbound phone leads just because of their name and all of the commercials they run. But, many of the residential sales that occurred within the organization came from salespeople who were good at canvassing neighborhoods (knocking on doors) and offering “Free termite inspections”.

After one particular hurricane season, a significant portion of Florida lost one to two weeks of business capability because of the storms. Businesses closed, roads closed and people stayed home and I assure you, no one wanted a “Free Termite Inspection” from some random guy knocking on their door during this time. For the state of Florida, revenue was missed, profit plan was missed and it was a pretty rough month or two.

Fast forward to the corporate meeting. VP’s & Region Managers had to go over their numbers in sort of a “round table open forum” type way. Each individual who ran a state had to get up in front of the group and go over their P&L. Everyone obviously wanted to highlight their positives and minimize talking about the negatives since the President of the company happened to be in attendance.

The Region Manager for Florida got up. He was a long term employee, knew the business well and was good at driving profit and revenue. Unfortunately, (and obviously because of the hurricanes), his region recently missed nearly all of their sales and profit plans. During his presentation, he brought up the fact that they missed because of the weather and how challenging it had been recently. He mentioned the fact that “He hoped the weather would cooperate in the next couple of months and they could make up for the recent carnage in sales”. The president, sitting at one of the tables in the audience, hunched over at his table, scribbling notes during each presentation, all of a sudden chimed in:

“If I had wanted a weather report today, I would have called the weatherman”.

You could have heard a pin drop in the meeting room. The poor guy at the front really never recovered during that particular presentation. He stuttered and stumbled the rest of the way through. It was actually pretty sad and I remember feeling bad for him. He was well liked so he was safe from an employment standpoint, but, me being in my early 30’s at the time, I had never seen anyone get clipped in such a brutal, yet factual fashion.

Later in the meeting the president got up to speak to everyone. He didn’t bring up that particular presentation, but he did talk about growing the business and the strategy to grow a business. He then specifically said “Hope is not a strategy”. Everyone knew exactly what he was talking about.

Over the years, those words stuck with me. Often in life I have found myself thinking “I hope I do well here, I hope they have a good earnings call so my stock goes up, I hope this crypto investment isn’t run by scam artists, I hope my real estate appreciates”. Looking back, many times I would rely on hope rather than relying on my ability to perform. As I matured in my business and corporate life, I quickly began to realize that there has to be a plan. A plan is far superior than hope. And if you have a plan, based on data that you have observed, that’s even better. Sometimes you can plan all you want and still lose a ton of money. Data to back up your plan is imperative.

Think about it for a minute. How often have you seen a new restaurant pop up in an area? Same building, different cuisine and name every few years. You’d think some of these restaurant business entrepreneurs would step back and understand that there is a good chance they may face the same fate as the previous 3 establishments that have been there and subsequently closed down over the last 5 years. But, just like many entrepreneur mindsets, they feel like they have something different. Some flare, some amazing cuisine, some new atmosphere that will change that and cause them to succeed. They base their plan on “hope” and that can be a lethal strategy.

When it came to my Short Term Rental endeavor, after I purchased my first one in March of 2020 and had a quick little scare with Covid shutting travel down temporarily that April, I knew I had a good thing cookin! By June, people were flocking to the Smoky Mountains. Flights, Cruises, International Travel had shut down and everyone was driving for their summer vacations. Couple that with the fact that no one wanted to stay in hotels around other people, the AirBnB market BOOMED. By July, it was no longer a “hope” for me. In fact, the first purchase in March wasn’t based on hope. Removing Covid from the equation, I ran the numbers backwards and forwards on my first purchase. Below is the link to that first one.

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After taking a trip to the Smoky Mountains with my kids February of 2020 and seeing the decent returns cabin owners made, I decided to take a plunge into a new venture: AirBnB’s. I didn’t have a crystal ball to anticipate the insanity in Real Estate over the next few years. I just wanted something that would cash flow. During that time I was having some struggles at work, in my personal life, with my side hustle business.

A day after my daughters and I arrived to the Smokies, Amazon sent me an email saying they were shutting my e-commerce business down over a single product complaint (yes they are that brutal). Coincidentally at that time, I also really wanted to get out of corporate America. After 25 years of ups and downs in my career trajectory, the grind had started to wear me down. I was banking on my Amazon business to save me and give me an exit but I realized quickly that I couldn’t be 100% reliant on that income when it could be snatched at any given moment. Pretty much my world seemed to be imploding. I needed another alternative.

I remember it vividly. I woke up before my kids that morning in the cabin and checked my emails. I then opened the Amazon email. “We are temporarily suspending your listings…you can appeal this decision by…”. My heart sank. I began to panic over Amazon, I was stressed about my corporate job, I had gone through a divorce. Sitting on that couch in this small cabin, I started doing the math in my head of what I paid for the stay vs what the owner’s mortgage might be and thinking that I need to find another avenue for income.

I thought…“I paid $1,500 to stay in this cabin for 3 nights. Let me look on Zillow and see what the owner paid for this. Hmmm $200,000 in 2018. So they probably have a $1,200/month mortgage. Now, let me check their calendar. Every weekend is booked and even some days during the week. I just paid this guys mortgage with one weekend stay and these other weekends have paid his mortgage for the next 5 months. Maybe I should get some more info on this cabin rental market”.

Those were literally the thoughts going through my head that morning. I got on the phone with the cabin rental agency that I booked the cabin with and asked the agent if she knew any good realtors in the area. I just wanted to talk someone. She connected me with one and I officially had a realtor in the Smoky Mountains. The realtor presented me with quite a few cabin options. I analyzed the potential income vs all of the estimated expenses I would have with an AirBnb (Mortgage, Taxes, Insurance, Electric bill, Water bill, internet, cable, wear and tear) and decided to pull the trigger on my first one in March of 2020. Granted, my last real estate venture back in 2003 ended in disaster by 2008 with foreclosures, ruined credit, finances turned upside down, so I was very hesitant to ever touch real estate again. But after running the numbers every possible way, I decided to move forward.

And then the world shut down.

I thought to myself, “Here we go again. I just can’t freaking win with this real estate stuff!” and for about a month it felt like a bad dream. Lots of post closing regret, lots of worry, lots of anxiety. But then a remarkable thing happened. Pigeon Forge eased restrictions (their entire economy is based on travel revenue) and it was off to the races.

That was it. That was the life changer for me. One simple initial cabin purchase. I paid $280,000 for that place. Before I closed, I received multiple estimates on what the rental income would be from reputable cabin management companies. High end was $75,000/yr. Low end was $55,000/yr. If you’d like to see some photos of my basic cabin I bought in 2020, the address is:

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After experiencing the various ups and downs of Real Estate, for me, what I am about to embark on is a no brainer. Low entry cost and high cash flow and a very untapped market. As I mentioned in the first part of this “New Construction Pivot”, series, the real estate that I feel the most confident in and that I will be plowing all of my cash is:

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I was first introduced to land by my dad. My dad’s side of the family grew up on some fairly worthless land in North Florida. Dirt roads and swamp land. That is until Peyton Manning and his family bought a big chunk right next to ours and I watched a series of catastrophic events unfold with one of my uncles.

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This New Construction Pivot series is going to be about a 6 part series. The more I get into writing this series, the more information I feel I need to share. For those who subscribe, you saw the specific niche in Part One that I will be throwing lots of cash into over the next 2 years. In that first newsletter though, I had lots of comments and private messages asking me to dig into how to find and buy the land, what to look for, how much to spend, etc. There is so much detail in taking on an endeavor like this, I would be remiss not to share every aspect of what it would take for you to do the same.

Over the past 4 years of my building construction, I’ve made lots of mistakes. I’ve spent money on land I shouldn’t have purchased and then hit grand slams on other pieces of land. I’ve discovered that some places are 100X harder to build on than others and also discovered that some counties are 100X harder to build in than others.

Below, I will outline some lots and pieces of land that I wish I had not purchased which presented EXTREME challenges to build on. I’ll also be going over some of the lessons in finding a great piece of land and what that entails. There are things you need to do up front before making a catastrophic mistake and finding yourself with a worthless parcel that you can’t do anything with and can’t sell.

Parts 4, 5 and 6, which will be released weekly moving forward will dive into more numbers, how to find good subcontractors, what you should be paying for certain aspects of your build and how to know if you’re getting price gouged.

As I mentioned in Part 1, the pot of gold at the end of the rainbow is building your own Short Term Rental in a vacation spot or close proximity to one. This could also translate to building your own Long Term Rental if you choose to go that route. Not hiring an outside builder who will make a significant profit off of building something for you, not buying an existing cabin…but building one for yourself. It’s much easier to do than you’d think. Heck, I had never built anything other than a Lego set 4 years ago. My life was centered around the bug business. But now I just broke ground on number 10 on my own. This will be a $1.5 million dollar luxury cabin and my build cost will be around $750,000 all in (including the land). Building your own will save you nearly 50% of what you’d pay for an existing one. I’ll be breaking down all the costs on spreadsheet, from the lot clearing and footer dig, to the framing, dry in all the way down to the finishing touches. I assure you, if I can do this, so can any of you. So let’s get down to the nitty gritty of finding the land.

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As I mentioned in my last newsletter, I have found a unique niche in Real Estate that I will be shoveling all of my liquid cash into over the next year. No it’s not the Kink Cabin, although I will be highlighting the numbers of it today. I’m sure the money maker that I’ve discovered will catch on sooner or later and there may be mass amounts of this style I talk about built, but better to be early to the party than late. I think I’m at the forefront of this one. Heck, I may even become the actual trend setter with it, since I know some of you may decide to try this yourself which will only increase the niche visibility. And then, as you know, with popular money making trends, things just start to spread like wildfire.

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As I mentioned in the last newsletter, this info is behind a paywall for a few reasons.

1. It’s an area I am gung-ho on and will personally be building for myself immediately. While the old Accounting 101 acronym applies to numbers, (FIFO - First in, First Out) I believe it also applies to trends. I don’t like to enter a trend at mid point and I definitely don’t like to be one of the last to enter them. The money is made when you spot a trend and you are one of the first to enter.

2. Lurkers - The more that read this, the more competition I may bring upon myself. While I know that the majority of individuals who read about a good idea don’t make a single move besides typing “Great idea, I’m gonna do that!”, some of you may actually do this. I could keep this entire money making idea to myself, but I like to see people succeed. At this point though, I’m not willing to share with X lurkers for free.

3. Anonymity - I once heard “Once you reveal your identity, you don’t get to put that genie back in the bottle”. I’ve been fairly anonymous for the last 18 months on X. A few know who I am, where I worked and other personal details about me, but I do still enjoy that most don’t. With some of these posts, more info about myself, my land, my properties, my new builds, will be made known. It’s hard to stay fully anonymous in the Real Estate niche and as I reveal more and more about my projects, I just prefer to have that info behind a wall.

Now, with that out of the way, let’s break down the numbers of this INSANE niche in Real Estate that I think is going to do some serious revenue over the next few years and it’s something that all investors could easily capitalize on.

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This is the one of those alpha moves that I have been looking for over the last year or two. Somewhere to plow my cash that can produce some insane returns. This 100% can be replicated by anyone with two caveats: it needs to be in a specific area that is prone to vacationers and you need to figure out how to do it yourself. I’ll elaborate later. I may need to break this up into two newsletters. The first going over the exact niche and the second, how to do it yourself.

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I give out a lot of free advice on Twitter but this will not be one of those times. Why? A) Because I am personally doing this one immediately B) I don’t need every lurker on the internet trying this and being my competition and finally C) There are quite a few revealing details about me on this one and I still like the semi-anonymity I have. This one is big and this is one area in Real Estate that I am extremely excited about. If you want to read about this niche in Real Estate that I’ve recently discovered, you’re going to have to forego your one Starbucks coffee for the month.

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Truth be told though, I also needed a small mental break. Am I interested in politics? Yes. Do I want political animosity to be incessantly in front of my face every time I open the app? No. But, unfortunately, in the climate we are in today, that’s just how it goes. There was an old saying in my corporate days when we would be readying new information or a new program to roll out to field operations. We would need our audience to absorb, in a short 3 day meeting, material that took us two years to prepare, which they in turn would need to roll out to their field employees. We would start the meetings with “Now everyone, this is going to be like drinking water from a fire hydrant”. That pretty much sums up how I feel with all of the political posts I see. A constant non stop barrage of mind numbing proportions. I realize I can mute/block people, key words and all the other tools in our arsenal to cultivate the feed to my liking. No matter what I did though, endless political material still shows up. And with that plenty of vitriol. I am sure, unlike everyone else with extreme discipline to keep scrolling on by, I inevitably get sucked into reading the comments of the posts and then look up and two hours have passed.

I would far rather see tweets about growing businesses, savings, retirement, Treasury bills, land, money, tax planning, estate planning, mountain life. You know, the fun and exciting stuff. The material that inspires your goals. But truth be told, at my age, I don’t get much “new” information to act upon when I even read those posts. I’ve built my wealth, retired from the corporate grind 15 years early, have my side hustles that sustain me and pretty much do my own thing. When you hit the 50 year old mark, you really aren’t going to learn a ton of new business and life information. You’ve learned most of what you’re going to learn…plus, you get stubborn. The key thing for most at my age is “Did we act on what we learned?”. For me, many many times in life in my 20’s, 30’s and 40’s, I learned what I should be doing, what I should be investing in, what I should be avoiding, how I should be acting, BUT I didn’t change my behavior. It took some hard life events to finally get me to start ACTING on what I knew and had learned earlier in life. I had the behavior in my brain, it just didn’t make its way down to my feet. Translation: I knew what I should do, I just didn’t do it.

• Don’t want to lose massive amounts of money with stocks/crypto? Don’t chase risky Stock Option Trades or crypto trades based on what you read on the internet.

• Don’t want to get crushed in Real Estate? Don’t take out crazy mortgage loans and lever up your eyeballs with rental properties like I did.

• Don’t wanna cheat and blow your family/relationship up? Then don’t even flirt. Run as fast as you can in the opposite direction of that person, including quitting your job if necessary. A lesson I had to learn the hard way.

  

While I do get tidbits of info that I can take action on with regard to business, taxes, life and other areas, it doesn’t make up for the exorbitant amount of time I would waste on the app. The ROI for me after a year of being on there constantly just isn’t there. The big gains for me on Twitter were actually things that most people would find trivial or silly. Getting a Ninja Creami after hearing about it non-stop on the app. Seeing Mike Cernovich post to put your HVAC filters on auto repeat order on Amazon for every few months when the filters need changing. (Game changer for keeping your Air Conditioner Filter changed in a timely manner).

With that in mind, I just needed a little mental break. I got extremely busy in my business life as well and the app just made me waste so much time on a daily basis. There are many parts of my personal life that I have not had much discipline with (as some of my long standing followers know), but one thing I can say…when it comes to my businesses, once I flick the switch, I get laser focused and driven.

My decision to take a break from Twitter actually came down to a mathematical equation. As most of you know, my Amazon business laid the foundation for my ability to walk away from a corporate America job after 25 years of be an employee of “the man”. I go into detail about this in some earlier newsletters. For those who have never done Amazon, August starts my holiday and Christmas season preparation. I begin sending in mass amounts of inventory to Amazon in early August. I started doing this back in 2016, after my first couple of years selling on Amazon. I began selling on Amazon in mid 2014, after transitioning from Ebay. During 2014 and 2015 I would send in my inventory to Amazon around mid to late October. It would arrive at their warehouse, get checked in and by mid November would be sold out. As I scrambled and attempted to send in more items in November, I realized very quickly “Every single person who sells on Amazon is doing the exact same thing and my inventory is taking forever to get checked in”.

One year I was reading the Amazon Seller forums after my shipped pallets had not checked in 3 weeks after sending them in to Amazon’s Fulfillment Center. People who lived near a big Amazon distribution center were saying the UPS trucks full of incoming inventory were lined up for 2 miles down the road. Inevitably my items wouldn’t get checked in until late mid to late December sometimes, causing me to miss 2-3 weeks of the major Christmas rush. After experiencing that I decided to start prepping in the late summer. My new goal became: I needed ALL of my inventory into Amazon by October 1st. Anything getting shipped in after that day would be “gravy” if it got checked in by Amazon. Has served me very well ever since. Don’t get me wrong. I don’t stop sending in massive amounts of material after October, but I realize some of those items may not get checked into Amazon in time.

Back to my math problem. As most of you know, Twitter can be a major time suck. It is a GREAT avenue to make connections, meet friends, build businesses, stay informed of world events. But there is so much data coming at me I sometimes feel like I get trapped quicksand. I get sucked into scrolling and can’t get out.

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With preparing shipments for Amazon, I profit between $2,000-$4,000/day if I am cranking out items. And yes, that’s profit, not revenue. Revenue is obviously much higher as my margins hover around 20-25%. I have a few part time employees, but mainly, it’s me and one other person. Once I started doing the building construction, I had to scale back quite a bit on Amazon as I was just getting pulled in too many different directions in multiple states. To prep items, I have to receive them, unbox them, inspect them, re-barcode them with my labels, re-box them and them ship them off to Amazon fulfillment centers. We can generally do 400-600 units per day on average at my warehouse. I have had days where we prep, label and ship off 2,000-3,000 units in a single day to Amazon, but those numbers are not the norm. To barcode and ship off even 400-600 items, it’s an 7-10 hour job. As Holiday season was looming in my head,

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Last week I discussed the nuances of my experiences with Short Term Rentals, aka AirBnB’s. This week I want to breakdown how STR’s can make or break you, depending on a multitude of factors. Recently I have witnessed many individuals who jumped on the AirBnB train in 2022 and 2023 only to be financially decimated in 2024. There were certain pockets of America that were pushed very hard by realtors local to those areas as “The hottest vacation market around” or “The best location to start your AirBnB business venture”.

One area that I showcased a foreclosed home in a recent post of mine was Blue Ridge, Georgia. Now, chances are, not many of you have ever heard of Blue Ridge. I had never heard of it before I moved from Florida to Atlanta 15 years ago. I would venture to say with even more confidence that none of you have ever heard of Mineral Bluff, an area in close proximity to Blue Ridge. But, for some reason, this area was pushed as the next great investment opportunity as recently as LAST YEAR!

Growing up pretty poor in the North Florida/South Georgia area, there were certain spots in the Southeast that my parents would take me on vacation when I was a kid. These were the spots in the 70’s and 80’s that you could go to on a budget. Daytona Beach, Panama City, Gatlinburg, TN, Myrtle Beach, SC. Most people, even outside of the Southeast, have heard of these. They have entertainment for parents and adults, stuff for kids to do, lots of attractions, views of the beach or mountains. If I were to break the US into 5 quadrants, the Southeast, Northeast, Midwest, South Central and Pacific, I would venture to say that each quadrant has certain spots like this. Drivable, easy on the wallet and fun. These are places that have been popular to visit for decades and will more than likely be popular vacation destinations for decades to come.

While real estate in these vacation markets skyrocketed over the last 4 years, the problem started when towns that had very little allure road the coattails of the real estate boom, mainly because of their “investment potential”. Much of this proposed potential was pushed in STR groups online, by local realtors and by buyers who were actually making money at that specific time.

A few things happened during Covid that drove demand through the roof for the unheard of vacation destinations.

1. No one was flying cross country or internationally. From mid 2020 until pretty much early 2022, there weren’t a lot of people flying. International travel dried up, domestic travel from one coast to the other dried up, short one and a half hour flights from FL to NY dried up. As you can see by the worldwide flight data below, it all dried up and took a while to recover.

2. Kids and parents were sent home. Schools getting shut down and many being forced to work from home caused some families to hit the road, even when it wasn’t the normal summer vacation months. Short quick weeklong “working vacations” spiked. Parents getting antsy being stuck inside with their kids thought “Let’s get on the road and get out of this freaking house!” Mini vacations, where the parents kept working, spiked.

3. Stimulus Checks - The first of the stimulus checks started arriving shortly after Covid hit. That influx of cash gave some families the extra money needed to hop in their car and take a small vacation that was easy on their wallet.

4. Ripple effect - While primary vacation markets skyrocketed, there was a major effect on secondary, tertiary and even markets extremely far away from civilization. “Get out of the city!” “Get back to nature!” “Go on a hike, you won’t catch Covid there!” were some of the taglines that drove the demand to visit markets that individuals had never heard of before, let alone ever visited before.

Long Term Rentals (rental property purchased with the goal of setting up annual leases) are pretty cut and dry. You know what your main expense will be each month, the mortgage/taxes. Other than that and any HOA fees you may have, you charge an amount for monthly rent (which hopefully is above your mortgage), collect the check, depreciate the depreciable part on taxes and wait for the sneaky expenses during the year, like the HVAC going out.

Short Term Rentals are a different beast. While neither LTR’s or STR’s are truly passive, LTR’s are usually way more passive than STR’s. Many people self manage their STR. When you see the term “self manage”, that means the owner is handling everything themselves. Bookings, Price per night adjustments, maintenance calls, In the age of electronics and wi-fi, it’s not really difficult to self manage. There are wi-fi keypad Schlage locks for your entry doors, wi-fi Honeywell Thermostats that you can control from 1,000 miles away when your guest leaves the AC on 67 all day in the middle of the summer, booking sites that sync to other booking sites (Airbnb, VRBO, Ownerez) for max exposure and minimum chance of double bookings. There is so much technology available for owners to self manage nowadays that it makes it fairly easy to do so. With self management, an owner eliminates the percentage of Gross Rental that a property management company charges. I have seen these fees vary from 10%-30%. Granted, a property manager handles everything from bookings, to cleanings, to maintenance and you just get the monthly check deposited, but that fee can prove substantial over time. Have a clogged toilet on the weekend? PM gets the call to handle, not you. You get charged for the visit and whatever the cost of the repair may be PLUS their management fee, but for some, not having to field calls or deal with difficult guests makes it worth it.

With the above in mind, a STR can get you sideways financially very fast if you purchase the wrong one. As mentioned above, secondary and further out markets, far away from a primary vacation spot, were marketed and pushed hard starting in late 2020. The party for many of that markets is officially over and many buyers in these markets are feeling the brunt of a high price + high rates + lowered rental demand. That is the trifecta of a bad real estate purchase, especially if the purchase was intended as a cash flowing investment. Let’s dig into the property that I showcased on Twitter recently and run the numbers from two different time periods, the purchase of the property in 2017 for $135,000 and the purchase from 2022 of $432,500.

Let’s run the numbers from 2017. Some of these will be approximations since I don’t have the buyer’s interest rate, monthly expenses, etc. I will be basing their expenses off of STR’s that I have had that are similar size and square feet. There will be a few assumptions like how much they put down, rates, income from rental, but the main goal will be to show you the disparity between two different purchases. A decent purchase that was done in normal times and a FOMO purchase, based on hype, emotion and a trend pushed by every online real estate guru imaginable.

Here are a few data points that I will be using. We will then back into the income or loss of the exact same property at two different times.

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Last week, I discussed some of my glorious beginnings of how I got started in flipping things which eventually morphed into Real Estate. These next two will be broken down into two segments. One detailing the income and expenses of regular Long Term Rentals and one breaking down the ins and outs of Short Term Rentals.

If you didn’t pay…

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Those are the new buzzwords of the year it seems. To me, they might be even more annoying than the “Team” buzzword that would infiltrate my corporate inbox on a daily basis that I wrote about last week. Despite the fact that “Get a side hustle” is extremely overused nowadays, I would be remiss not to say “Get a side hustle”.

How did my original side hustle start? Well, for the original one we would have to venture WAY back. Back to when I was 13 years old. I learned early on about the process of flipping. Flipping is exactly what it sounds like. Buy something for a certain price and sell it for more than you purchased it for. It doesn’t matter if it’s Real Estate, Widgets, Toys, Junk, Stock & Bitcoin (aka trading).

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I bought into it. Many do. For a significant portion of the population, corporate life provides a good life, a steady paycheck, decent medical insurance, fairly decent retirement. But, the security and steadiness defini…

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