Terrible Jobs; Good Lessons

I think everyone has had a terrible job before. The worst jobs or clients I’ve had have been the most interesting to look back on and see how they have shaped my approach to FIRE, business and life in general. I’ve had terrible people I’ve worked with and terrible jobs but these 2 are the ones that stand out in what shaped me and my approaches to business and management.

UPS Management – What a total shit show of a place to work. If you work in management at UPS up until YESTERDAY (11/10/2020) you are not allowed to have a beard. It’s this strange management structure that hasn’t fundamentally changed from the 1950s. These strange structures makes the general work environment insanely toxic. Supervisors (that is what I was) are the lowest levels of management and there is a never ending chain of management above them that only care about numbers. The higher up the person is that decided to get angry about a number that day and yell at the guy below them the worse that shit was gonna be. God help you if a VP started the chain; you might lose your job if you don’t make it better quickly. Notice how I’m just saying number? That number could be production, overtime, hours per shift, skilled hours, delayed pieces, it’s all just some number that a nerd (like me) made up. Shit rolls downhill and I’m certain that phrase originated with someone who worked at UPS. Impossible standards and working insane hours to meet those standards created a terrible place to spend time. Despite all this wasted time, energy, expense, hours and human enjoyment this company makes billions every year.

Crazy publisher man – While UPS has its flaws I have heard it has gotten better since I’ve been gone which is going on 13 years now. All my best terrible job stories come from just one place. My first job as an accountant in the private sector was for a company that published OSHA books and sold them over the internet. Really he copy and pasted text from OSHA websites, did some formatting, made them into giant books at his own printer and sold them to companies to put on a shelf and gather dust. I thought he was a genius. He was making over $5 million in PROFIT every year with less than 20 employees. I was so excited to be this guys ONLY accountant. Fuck yeah, let’s do this, I thought. Unfortunately, that guy turned out to be the most bat shit and evil human I’ve ever encountered. Inches from an employee’s face screaming and spitting at max volume…weekly at least. I think I lasted like 3 or months before I got my first one and told myself I would not stay. I did as little as possible each day and job hunted hoping to get fired. He fired someone about every 10 days of his 18 person staff so it couldn’t be that hard. When he finally did fire me for not coming in for 2 days I said cool and got my stuff. When I filed for unemployment he had his staff attorney create some crazy story and deny my unemployment. It was something with a signature on a check he said was my signing his name? It’s been a lot of years and the story they made up was never fully told to me by them or the unemployment office. I was denied and from talking to other coworkers learned that he did that every single time. He would fire someone and then intentionally lie to ruin their lives just a little harder. Big time asshole and yet each week there was a new hire unknowingly walking into hell. Even crazier is that he still was making north of $5 million a year.

As I’ve gotten older and done decently well in business I think back to that job as the worst and best job I’ve ever had. It’s certainly the one I learned the most at. I learned that business is easy and some ideas are so good that you make money in spite of yourself. Ever since I worked for this crazy bastard I’ve asked myself and my friends the question “What would this guy’s empire have been like if he were just a decent human being.” He was doing everything with entry level people that he trained himself and then scream opposite instructions at two weeks later. He hired a full-time attorney as part of his staff mostly to fight his crazy legal battles and deny unemployment to people he fired. There is more, a lot more to tell on this guy but at the end of the day he was making millions.

Ever since then I’ve approached my business life with the goal of not becoming these people. Once I got more into FIRE I felt sad for that crazy man. At the income that business made when he wasn’t there would pay for the most luxurious life a person could imagine. Instead he toils in there wrecking up the place and holding himself back way past the point of him even needing the money.

I learned that you work as hard as you can, treat people decent, spend some but invest more and when you have enough you get the fuck out.


Wildfires and Climate Change

Well FIREDad has just returned from our first mandatory evacuation from our home and let me tell you it sucks. I know you’ve seen people interviewed that say it’s so much worse than you can imagine and let me tell you they are right. There really is nothing quite like having less than an hour to pack all your things, animals and family members into your car then driving away with a hellfire inferno on all sides of you.

Wildfires have been a threat to homes since humans started building homes. When I was a kid I remember hearing about the wildfires and how they would burn some homes that were remote and especially cabins. Today these fires are burning bigger every single year with the fire that displaced our family being the biggest in CO history. This shit is not normal and feels like a crisis we are ignoring.

During our evacuation we stayed with our neighbors and got some interesting insight into the way others think. During the two weeks we were forced from our home we had a lot of time to think about what we would do next if our entire town and community burned to the ground. After a disaster there are the people that will rebuild every single time. Where I grew up these were the river people and every time they were flooded they would march back in and rebuild. The mountain people are no different; our neighbors would rebuild every time if the fire took it all. The FIRE family is not that way and we would walk away. It’s a very surreal thing to have to plan for and think about, but it’s an important exercise. It’s best to know what you would do in advance and have a plan rather than react emotionally.

Of course, Estes Park did not burn and life has returned to normal until the next hellfire comes in to threaten us again which I’m sure will be next year. Come on humanity, let’s just take climate change seriously. It’s about time and might even be too late.

America Divided in 3

The world is changing and America is no different and it feels like we are turning a corner that cannot be reversed.

The income disparity in the US has always been extreme, but what is happening now is a spread that might not be able to be overcome. I’m not talking about the billionaire class or the 1% or politics as those have been discussed by far more educated people that I am.

I’m referring to the cost of living across the US. There really are 3 Americas right now and it feels next to impossible to move up from one to the other. Let me explain.

3 levels of America – 

3rd world America – Deep south and rural north. Examples include: Rural Mississippi, North Dakota (not cities), native reservations.

2nd world America – Rural areas of 1st world states, populated areas in less desirable climates. Examples include: midwest metros, Raleigh NC, Des Moines IA, Albq NM.

1st world America – Big cities and states in great climates. Examples include: Colorado, all the west coast, most of the east coast, Chicago.

These have existed in three different levels for my entire life, but the disparity has gotten huge. Six years ago the FIRE Family moved from a 2nd world America to the 1st. We moved from Davenport, IA to Estes Park, CO. At the time we sold our home in Iowa for $150,000 – exactly what we paid for it 3 years earlier and purchased a major fixer upper in EP, CO for $300,000. 

At first glance those numbers don’t seem too bad since it’s double the price for a much more desirable location. I’ll concede that six years ago that was a doable trade and transition. The problems come in what has happened in those six years. The house we sold in Iowa is still worth basically what we sold it for. Our first house in Estes we sold one year ago for $475,000. We could have done some more work to it and gotten the value well over $500k.

The price we sold our first Estes home for was higher than we could have even afforded. That means in the six years since we first came to Estes we are lucky we came when we did, because as of today it would have been near impossible for us to afford that move. This is happening all over the country across all the different levels of America listed. Values of homes and cost of living in 1st world America continue to rise while the lower tiers are staying relatively flat and in the case of the 3rd world are actually decreasing. 

As with all things it is important to identify the problems and do your best to maximize the situation. In this case the move is to find some beautiful land and homes right on the edge of the 2nd and 3rd world and purchase a manor when the same money in the 1st world America buys you a 1 bedroom condo. 

If you find yourself trapped in 3rd world America or even the lower tiers of the 2nd world it is getting more and more difficult to transition to the top tier and if you are planning on it then move fast. Every year you let go by is going to become more expensive and restrictive. I was a full blown adult during the 2008 housing crisis and while it is obvious we are living in a real estate bubble right now I do not believe that bubble will burst especially hard in the 1st world America. There is just too much money at the top and these areas are extremely desirable. Demand drives up prices and good weather and recreation is not going out of style.

I expect in my lifetime we will see America divided in a more formal manner. If you’ve spent any time traveling this country as I have you’ll know that there really are multiple Americas and the disconnect has never been greater. The best we can do is take these observations and do the best we can for our future. For the FIRE Family this means we are planning to become self sufficient and use our income/savings from the 1st world to buy a massive property in the 3rd world with the intention of homesteading. While that goal is pretty unique the lesson is still there for others to learn. Wealth inequality is not just a 1% vs the rest equation. There are quite a few different problems that are arising from this issue and it’s important that we all stay educated and informed.

Resort Skiing is a Curse on Humanity

No one around. Peace and perfection

The Fire Family lives in Northern Colorado in the mountains and winter is the most important season of the year. Winter means that every day is an adventure in the backcountry and each time we are lucky enough to go explore and play is a gift to be cherished.

My goal each year has been to get 100 days each season and while I’ve never hit that number I get to at least half of that every year since moving here. In the 6 seasons I’ve had in this wonderful place I have ridden a chairlift exactly one day. It was a pretty fun day with friends, and we were lucky to have one person with us who had discounted lift ticket pricing. Our party was 3 guys and since we all work together in one of FireDad’s companies I footed the bill. The total cost for the day which included 1 free lift ticket, 2 tickets at $30 a piece plus lunch with a beer each was still $150. Had we paid full price for that day the cost would have been around $375 for one day of skiing and an overpriced lunch.

The mountains serve many purposes, but the one I like the most is adventure. I do not find much adventure in resort skiing. In fact, I am here to say that resort skiing is a plague on humanity and the mountains.

Resorts are not natural. They take these beautiful and natural locations then proceed to alter them in generational changing ways. They rip tens of thousands of trees out, make fake snow, install concrete and metal structures to haul our fat asses to the top, use explosives to flatten areas of the mountain to be “accessible”, build giant cafeterias into mountainsides, etc, etc.
Ski resorts do serve a purpose. They are great places to learn the sport, have a luxury vacation occasionally, but the amount of waste these monstrosities produce and inflict on our world does not outweigh their good.

Alternatives? Get your ass in the Backcountry

Yes the foreign concept of putting skins on your skis and hauling yourself up the mountain, finding your own lines in powder never seen or touched by a human. This is skiing as our ancestors did things and as I get older I’m quickly learning that modern is rarely the best.

Backcountry skiing is only for experts though right?
This myth needs to go away. Just like a resort nearly every place in America you could ski has been already assigned a difficulty and skill level using the same system. A beginner shouldn’t do a black diamond at a resort just the same a beginner shouldn’t do a black diamond in the backcountry. I’ve been skiing and snowboarding my entire life and I am smart enough to not do any black diamond or above when I’m solo. I won’t touch most double blacks in the wilderness unless I am very confident of my line beforehand. It’s basically the exact same rules you follow at the resort except the trail signs aren’t there.

Ski resorts in the United States and most of the world are gigantic, billion dollar companies and conglomerates. The activists that love skiing and protest the pillage and destruction of natural resources seem to have a blind eye to ski resorts and it’s baffling to me why. The only thing I can come up with is that they just love downhill winter sports so much they feel it’s the only way. It’s not, and the alternative is much better.

How to get started?

You don’t need some fancy setup with special bindings, expensive skins and inflatable avalanche packs to get into the backcountry. Here is all you need:

  • A friend to come with your first few times
  • Skis or snowboard
  • If your setup is for a resort then a cheap pair of snowshoes
  • a pack
  • bungie cords or rope
Look at that, they fit on your pack!

Scroll through this picture gallery that I’ve collected over the last 5 years. Highlights include: beautiful scenery, powder deeper than you’ve ever seen it, and not a single line to wait in. Why would you pay a giant corporation your hard earned money for a shittier experience?

The Boy Scouts Had It Right 100 Years ago

I am an Eagle Scout and I am pretty sure a large amount of my decision making process was heavily influenced from my years in the scouts. While they didn’t turn me into exactly what they wanted (pretty sure they didn’t plan on anyone coming out a card carrying atheist) the core values of scouting are a great road map to build a wonderful life.

For those unfamiliar the scouts have a few mottos they live by. The list of 12 laws are particularly wonderful with almost no exceptions.

There are 12 principles a Boy Scout lives by which is actually considered the Scout Law. “A Scout is trustworthy, loyal, helpful, friendly, courteous, kind, obedient, cheerful, thrifty, brave, clean, and reverent.”

The 12 words in the Scout Law are so well rounded it’s hard to think of anything to add or remove.


We start strong with Trustworthy. Remain someone who’s trust is unquestionable in every circumstance. If you disagree then speak your mind, if you promise something you follow through and see it to the end. Being Trustworthy is one of the keys to financial success in our world and an excellent first word.


The hits just keep on coming with word 2; Helpful. Being helpful to those around you is such a wonderful way to live your life. Your friends, family and co-workers know they can rely on you because you are always willing to lend a helping hand. Maybe you need to help someone meet a deadline, you help a co-worker for 2 hours on their project; maybe a neighbor needs help staining their fence. By remembering to always be helpful in turn you will have others always willing to help you.


No one likes an asshole. This applies to all forms of negativity like gossip, hate speech, intolerance and sorts of other bullshit. Be known as the person who is laid back, cool, tolerant and Friendly.


When I was younger and actively in Scouts this one was the one I forgot when reciting the list. It always felt like it could be rolled into friendly. I thought this way right up until I started experiencing the real world. People are fucking terrible and if you’ve ever worked in food service, cashier, etc you’ll know that a Courteous person can change the entire course of your day. Be understanding to those that serve you, be overly generous with gratuity, and not only will your path through life be more pleasant but so will everyone else’s you encounter. Think to the last time a fast food worker had to tell you to go park and wait. Did they act timid and a little afraid to tell you that info? Yeah, well it’s conditioning because way too many people are fucking awful human beings and being a little more Courteous makes the world a better place.


Kind is a synonym of Courteous! Yeah, that’s the point. Being a Kind person is so important they listed it twice so you won’t forget. Be kind to others; it’s really not that hard, but it is rewarding.


A rare miss, but I always treated this one a little differently. There is a time and a place to question authority and there are times to be obedient. In extreme circumstances like an extreme wilderness adventure where being obedient to your Scout leaders is crucial to keep everyone alive. There are times to disobey. Trust and listen to experts, scientists, and people whom you respect. Question authority that claims they have authority for authority’s sake.


We took a detour but we are back with some serious chops with Cheerful. We all like to bitch about our problems, stupid people, politics, squirrels that steal your bird seed or whatever other issue you have with the world. There is a limit and nobody likes a Debbie Downer or a Pouting Pete. The world is awesome and there is an unlimited amount of cool shit you can spend your time on this planet doing. Don’t get bogged down in the stuff that sucks. Focus on the good in all things.


It’s not going to come as a surprise that this is my personal favorite. The entire world of personal finance consisting of college courses, degrees, full-time speakers, bloggers, Dave Ramsey, Suzi Orman, MSNBC, wallstreetbets, countless books, and the Boy Scouts managed to nail it down with one word: Thrifty. The ability to give a lifetime of financial lessons in a single word is a work of art. Let’s explore why thrifty is the perfect word to include and how it covers all manner of personal finance advice.

  • Implies to get a good deal, due your research and make informed decisions
  • Combined with other Scout Laws means to help others in their time of need. If you follow this one also then you’ll have the financial means to help others.
  • Here are the most common synonyms of Thrifty: Frugal, Economical, Sparing.
  • Approaching your personal finance with the idea that each purchase or decision is made with the idea to get the best value for your money is a great way to live your life. It’s how I live mine, learned from Scouts, and continue to follow this law to this day.


In adult speak this translates to “don’t be a bitch”. Stand up and face your problems and fears. Tell the truth even if it’s uncomfortable. Stand up for what is right in all circumstances even if there are negative consequences. Don’t be afraid to venture into the unknown as discomfort is the source of inspiration.


Typically the first piece of advice a therapist gives to someone working on depression is to clean up their environment. It feels good, instills a sense of purpose and places value on your existence to see progress on something. If you ever go down the deep web rabbit hole and read about incel support groups, you’ll see that one of the first pieces of advice is to CLEAN YOUR ROOM. It doesn’t need to be perfect but a reasonably clean living space that isn’t filled with trash, dust and filth with have an immediate and positive impact on your life.


I have been an atheist who was raised Catholic for most of my life. The last memory I have of believing or at least following the Catholic God was around 3rd grade. I remember asking our religion teacher a question and getting yelled at for questioning something…..in school. From that point on I was on the “this is bullshit” train. Reverence to me has a different meaning. It means to respect the beliefs of others and let them live their lives in peace. Whatever views you may have is totally fine but you do not have the right to infringe on differing beliefs of others. Live and let live.

Scout is trustworthy, loyal, helpful, friendly, courteous, kind, obedient, cheerful, thrifty, brave, clean, and reverent.” When you really dive in and think about each word and it’s deeper meaning on a life it’s hard to think the Scouts were wrong. I was in Scouts long before the scandals came out and I believe my life is better as a result. While not everyone has the privilege to be involved in such a program we can still all read and understand their laws and apply those lessons to our daily lives.

Partnerships – Should you?

“The only ship that always sinks is a partnerSHIP” I read that somewhere from some guru and it sure seemed like bullshit at the time. After the last 15 years of starting multiple partnerships I can say that it’s mostly bullshit, but has a tiny amount of truth buried in there.

I’ve started quite a few businesses in my years and a lot of them have been partnerships. It just makes sense for a startup that is cost conscience that rather than hire someone and having to pay them every week you can instead join up with them. The first few years of the growth you have the benefit of an overqualified individual working for less than they are worth in exchange for ownership and future potential. In my time with partnerships I’ve had quite a few different approaches with varying degrees of success and failure.

  • Working for a sole proprietor to learn the craft then joining them – This one was a big mistake as I knew he was crazy. I never lost any money, but the headache every day was annoying and I wanted out in the end. I will never talk to this Qanon conspiracy crazy bastard again in my life and I’m better for it.
  • Joining up with someone that I only knew professionally. This worked out quite well and only ended because they wanted to bring their spouse in and I didn’t want to be a third wheel in a power dynamic where my voice effectively would be worth less. I moved on and am happy about everything that happened for the most part.
  • Starting businesses with your friends – This is the golden ticket to success. I avoided this for years because of the stigma. Everyone in your life, media, books, writers, gurus, bullshitters will tell you that starting a business with your friend is the best way to lose a friend and money. Those people are idiots.

Starting a business with your friends is the best thing you can do if your friends are decent people.

That’s the key to success with going into business with friends. Nothing really matters as long as you respect each other to begin with and have similar values. The mistakes I’ve made in starting businesses with people has always been working with people who didn’t have the same philosophies in life and business. That’ll dick ya down everytime, but if you work with your friends and are all driven towards having fun and making something awesome then you’ll have a blast and make money. 

As we are approaching FI I have gotten so much less tolerant for any work related bullshit. This also relates to any business I own a stake in. If I don’t enjoy it then I am out. With this scaling back I’ve noticed that the only businesses I am excited to work on each day are the ones that I’m doing with my friends. We are doing cool shit and are trying to be on the cutting edge every day if only for the sake of figuring out the best way. We invest aggressively on ideas we think are awesome and every ownership call is a goddamn blast because I’m just hanging out with my buddies bullshitting. It’s just rather than talking about politics we are talking about how to make our business the best it can be.

That’s my dad advice for the week – Get friends that are good people, then go into business together on something you would all have fun doing.


Make a difference in your community

The title of this post can relate to so many things in life and every single one of them will have a  wonderfully positive effect on your life and community. Social media activism is a feel good echo chamber and should be avoided at nearly every turn. Trying to change the world on the world or even national level means you are one voice of millions or billions. Unless you are a very unique person with generational skills to rise in fame, and I mean on the level that 100 years later we remember you so well you are referenced by your initials (FDR, MLK, JFK). If you aren’t destined to be a generational hero; I have good news for you. You can still make a difference in the world, but you are going to be a lot more effective if you think small.

It’s surprisingly easy to change a law at the town level. If you don’t like something and can find enough people to agree with you all then just write up your proposed changes, contact your Town Hall and request a ballot initiative. They will tell you how many signatures you need and when it’s due. From there you haul your ass around on your bike to all your friends, colleagues, business owners that might agree with you. Hell, go talk to people you don’t think will agree and see if they will sign your petition. Get the required amount of signatures and just like that, your new law, amendment or proposal is going to get voted on! 

Do you think your change is logical and could be changed without a vote? Go speak to your Town Counsel and all elected officials, write emails, interact with them on social media and explain your position. You’ll be surprised how receptive they are to a logical argument  and unlike when you call or email your senators, these people will listen, interact, hear you out and could even officially propose your amendments. 

I’m not saying you shouldn’t stand up for your positions and politics nationally, but if you want to see immediate change your best bet is to start in your own community.

Budgets are stupid, exhausting and need to die

Budgets are the worst lie being told by the personal finance industry. People like Dave Ramsey are happy to sell you a shitload of useless products to budget more effectively. All you have to do is pay him some money for those products and he promises he will save you even MORE money back!

If you’re brand new to the concept of how money works then sure, budgeting is a great form of training wheels. Once you have a basic understanding of saving, investing and Money 101 then budgeting is a colossal waste of time and resources. How is budgeting still a thing that is being sold to people in the FI/RE community? 

Over the years I have tried every budgeting approach you can think of. I kept trying different approaches and then always giving up or failing. The reason I kept going back was I would fail then end up reading some blogger or article about how budgeting is the number one key to financial success! Turns out, that’s all bullshit.

When you look at ways to simplify your life you’ll want to look put the magnifying glass on every way you spend time each day. After multiple failed attempts at budgeting I was trying again. Putting each item I had bought in a spreadsheet to figure out how much I spent, trying to figure out how to categorize some random purchase and I realized this is a colossal waste of time. Don’t believe me? These are Dave Ramsey’s top 10 signs you need to spend MORE TIME on your budget.

1. You’re constantly worrying about money emergencies.
2. You use the same exact budget each month. 
3. You aren’t tracking purchases.
4. You don’t have a budget line for giving. 
5. You overspend in one category. A lot.
6. You forget annual expenses. 
7. You need space for a new budget line item. 
8. You aren’t budgeting to zero. 
9. You just hit a Baby Step milestone. 
10. Your budget doesn’t line up with your money goals. 
11? You Need to Refresh Your Budget by Season 

How many hours a month am I supposed to dedicate to this bullshit? I have to spend every single dollar before the month begins……why?

Here is what I do now and I have done for the last several years. It takes almost no tracking, no line items, no seasonal budget adjustments and it maximizes our savings.

FireDad’s budget approach:

  1. Automate all your savings and investments
  2. Spend less that what’s left in your account
  3. Don’t waste money on stupid shit

There you go! If you follow the patented FireDad budget not only will you not stress about your zero balanced budget, you won’t think about budgeting at all! Even better there are no envelope systems to buy, no software, no step by step books, this budget can fit on a sticky note you attach to your credit card and can sit in your wallet unaltered for years like that expired condom.

Stop wasting time on worthless tasks that over complicate life.

Cheap TVs are amazing

If there is one thing a dad is good at it’s spotting a deal and Firedad is no exception. Gather round kids, it’s story time.

I graduated high school around the same time as the television revolution. The time when flat screen and plasma TVs were just starting to become good enough, light enough and affordable enough that the average family could afford the technology. My roommate a few years later actually purchased a 50” plasma when she got a really good paying job and we all thought it was the tops. From then until about two years ago the technology kept getting better and cheaper with us reaching the point now where shit is insanely cheap and the tech has pretty well flattened. Sure the newest and best is slightly better, but entry level is worlds better than what we had in the 2000s.

Go on Amazon right now and you’ll find a fully functioning smart TV with Roku 50” for $225. Once you start getting huge the prices go back up (cheapest 75” I found is $750).
The highlight here is a 50” fully functioning smart TV with incredible picture quality for $225! This is the point where a salesman would tell you that those are “old” technology and you really want the QLED or curved or ultrathin or whatever new thing is out. The truth is that society has reached the point where “old” TV technology is awesome. 

They are so cheap!

At this price we added one to our guest room and bedroom. I’ve been thinking about adding one  to the patio as well. The convenience to watch YouTube videos anywhere or stream Netflix in the background for so cheap is unlike any other point in history. 

The next TV related thing to do is to drop your shitty and overpriced cable package. Cable television is a cancer on society and the sooner you can get  away the better. Our televisions show shockingly little TV. We sometimes stream old shows at night, but mostly it’s wonderful background videos, movies or YouTube tutorials. It’s very convenient to have a large screen streaming a cooking step-by-step as you’re working in the kitchen.

One last thing. It’s not a deal if you don’t need it or want it. Just because I’m saying these things are a great value does not mean you should get one unless you have a use for it. Nothing you pay money for is a good deal if you didn’t need it.

Now hand me the clicker.

So You Wanna Buy A Sports Car?

Some of us are just born with a love of cars. It runs deep in our blood. I believe that electric is the future, but I  also believe that a naturally aspirated engine with perfectly engineered steering can create religious experiences. So whenI hit the age, income and NW to comfortably start thinking about a purchase this ridiculous I knew I had to do it right. I knew my wants list and for today’s blog post we are only talking about wants. Anyone that says a sports car is a need should really check themselves at the door. 

My wants list was pretty small but pretty specific: it had to be a manual transmission, regular maintenance had to be DIYable, I wanted it to be daily drivable and trackable, and I wanted it to be a Porsche. 

After a ton of research I settled on a 1999-2004 911 4S also known as the 996 generation. If you’re not into cars the story of the 996 is fascinating. If you are into cars there is a good chance you’ve heard about it by now as the secret is starting to get out. 

The Porsche 911 is the flagship sports car. Every generation over the last 50+ years has been beautiful, powerful, fast, fun and track ready from the factory. For this, and many more reasons the Porsche 911 has held its value surprisingly well and in lots of cases has become worth more than the original MSRP for good models built before 1999. You see in 1999 Porsche made a few changes to the 911. First it went water cooled from air-cooled which was pretty much necessary to keep up with the performance of competitors. They also implemented some changes that  most automakers do of sharing parts across models. The cardinal sin of the 996 was sharing its headlights from the Boxster and going away from the classic 911 round headlights. 

There are a few other gripes about the 996, but the truth is that at its heart and core the 996 is a 911. It drives just as good as it’s more expensive brothers and sisters and it does it for less than half the cost of nearly every other generation. Here is mine – a 2004 911 Carerra 4S.

996 backcountry

I bought this car for less than the price of a new Camry including delivery and some minor repairs. I’ve had the car about a year and in that time it has actually appreciated about 15% from what I paid. That’s the funny thing about sports cars – the markets fluctuate and if you spend the time researching you can clearly identify vehicles that are undervalued. I’m not advocating for trying to make a profit with your sports car addiction I’m simply saying that you should make the purchase smart and with some forethought. Other than maintenance and repairs the cost of owning my very own piece of vehicle art will cost almost nothing. Meanwhile a 2020 Carerra 4S is $127,900 before options. Ask yourself if you want the car for the status or to maximize your enjoyment for every dollar spent? 

I will always take the approach of maximizing my dollar spent. I drive a car that I had a poster of in my locker in high school and my total cost of ownership so far is less than a fully loaded Kia. I’m into this car for under $30,000 and it’s a pristine example. You can easily find amazing, exciting cool cars for so cheap if you just know the markets. I actually found a friend of mine an Aston Martin Rapide for $52,000 a few weeks ago. It was a 2012 with 40,000 miles.The original MSRP was well over $240,000. He had always wanted one, is pretty close to a Fat FI/RE number and was blown away when I found his dream car for less than a new F-150. 

Do your research, learn the market and buy used but reliable. It’s a great experience to learn the known issues of your dream car and how to wrench on them yourself. It’s a far more rewarding experience to have something you need to take care of rather than walking into a dealership and signing up for a giant loan. 

In 2019 85% of new cars were financed and 56% of used cars were financed. Exotics are financed at a rate of 89%. Imagine having to make a monthly payment on something you can’t even use every day, doesn’t that sound miserable? I don’t think I could enjoy my beautiful sports car knowing it was chained down with debt.

The principal of buying used, learning the market, being an educated buyer and paying cash are principals that apply to nearly every major purchase. Whether it’s a house, car, boat, vacation home, plane, yacht, villa, or island the same rules apply. If you do what everyone else does you’ll learn nothing, gain nothing and be stuck with payments the rest of your life. Who wants that?

I remember my grandpa working on old mustangs and ancient fords he pieced together from junk yards. He was a child of the depression who didn’t go to high school. I’m still working on being as frugal as he was, but those skills made their way down the bloodline of finding the right deal and doing as much of the work yourself as you can.