Dare to Pursue the Unconventional Path (They Don’t Teach You THIS in School)


Not long ago, two identical twins were born, Brien and Brian. Brien was the older of the two twins, and throughout their childhood, always seemed to have a leg up on Brian. Brien was the better student, better athlete, better with the ladies, and just seemed like the type of guy who was always flying high and headed in the right direction in life.

By no means was Brian a slacker… He just couldn’t keep up with his twin brother, but then again, not many people could. Through hard work and persistence (they do teach you this in school!), Brian was able to somewhat keep pace with his more gifted brother. Both twins attended UC Berkeley and studied Mechanical Engineering. After 4 grueling years, they each graduated with that coveted B.S. degree.

Up to this point in life, they were about even, as far as an outside observer could tell. True, Brien graduated with high honors and was a member of the prestigious Tau Beta Pi society. On the other hand, you had Brian, who graduated with a C average and spent more time dancing than he did studying for finals. Still, they both walked out of the Greek Theater that gorgeous afternoon in the middle of May, as proud as one could be.

It is at point where we begin our story. The story of how a few important decisions can not only have a profound impact on your life but also alter its course entirely. The story of life…

The Story of Brien

Brien was always on top of things, so you wouldn’t need to remind him to go looking for a job immediately after college. He was a go-getter who had secured a full time gig at the local gas and electric company prior to the start of his final semester at school. Always one looking to get ahead in life, Brien opted not to take any time off after graduation, and immediately started working the following Monday.

The first three years after college went exceptionally well. Brien made strong contributions at work and was promoted on two separate occasions. He was now making a six figure salary + bonuses. Although Brien did succumb to some lifestyle inflation, he was also a diligent saver. He wanted to get ahead in life, and in his mind, getting ahead meant he absolutely must own his own house.

Brien’s Thoughts

Brien was sick and tired of paying rent. He reasoned, paying rent is for suckers. Why should he labor to make somebody else rich? Rent keeps going up all the time, anyway, so wouldn’t it make more sense to just buy a house and get a 30 year fixed mortgage? Besides, Brien was now in a serious relationship, and being the planner that he was, he was already thinking about their future… and kids.

Brien’s Plan

Fast forward five years, and Brien was now 29 years old. He was engaged, in great health, and after a lot of hard work (eight years), had the downpayment needed to buy a starter 3 bedroom, 2 bathroom single family home in the Bay Area. The house was located in the suburbs and very close to all the major highways. The schools were all excellent as well.

Everything looked good on paper… except the purchase price. The home was expensive, no question. However, the bank had pre-approved Brien and his fiance, so in his mind, he was absolutely qualified to take out the loan.

Here’s the breakdown:

Property Bay Area
Room 3
Bath 2
Interest 4.850%
Price $638,000.00
Downplayment % 25
Downpayment $159,500.00
Loan $478,500.00
Mortgage $2,525.01
HOA $25.00
Property Tax $418.42
Insurance $21.67
Monthly Payment $2,990.09


For the next ten years, Brien went full-speed ahead in trying to pay down the mortgage. He was laser focused… some might even say possessed. “Got to take care of the mortgage“, he reasoned. Once the home was owned free and clear, he thought, life would get infinitely better for his family. They would finally have some breathing room and some spending money to play with. So, Brien embraced the frugal life. Deep down in his heart, he knew that his main focus must be to eliminate the evil debt.

Brien was on a tear. He was paying down the mortgage at an accelerated rated. Although he opted for a 30 year fixed rate, he was shaving off years by being so relentless in his pursuit to pay it off. Every bonus, stock option, or other windfall went straight into the principal repayment.

Brien’s Struggle

Everything was going exceptionally well… until one day, the unexpected happened. There was a major macroscopic event that caused the global stock markets to free fall. Everyday, it seemed, the markets would close deeper in the red. The bleeding just wouldn’t stop. Brien’s 401k and retirement plans all took a nosedive. Even worse, the real estate market crashed as well. Brien’s $638,000 house was now only worth half that… at most.

Struggling to come to grips with this grim new reality, Brien did what he did best, he poured his heart and soul back into his work. He worked even more tirelessly, sometimes 16 hours each day. Still, all this hard work couldn’t prevent the impossible from eventually happening…

Brien’s Reality

Brien was let go. The company was forced to make a tough decision, and had to do something in the face of this financial crisis. Ultimately, upper management decided to consolidate Brien’s entire group. Just like that, the impossible became reality.

Life had just kicked a man who was already down on the ground. What was Brien to do now? His house was not only underwater, but he was unemployed as well. His wife wasn’t working… she was too busy trying to raise their two kids. What about the mortgage payments? Principal + Interest alone were over $2,500/month. PITI approached $3,000/month, yet the place could only reasonably be rented out for $2,400/month… at most. Underwater and cash flow negative?!? That’s never a good place to be. Also, at this juncture, what bank would be willing to refinance? His home was now worth even less than he owed!!

And just like that, life happened. Brien was in serious trouble… Unemployment would eventually run out, so he knew he would have to find another job. The fear of missing a mortgage payment and having to go into foreclosure nearly drove Brien mad. He had immense difficultly coping with this potential reality. One late night, a week later, Brien had trouble falling asleep. He was breaking out in a deep sweat, and had trouble breathing. He got up, and tried to walk it off…

Brien’s “Fate”

Why me?” Brien constantly questioned. He didn’t get it. He did EVERYTHING he was supposed to do in life. He graduated from a prestigious university, worked tirelessly at his job, got married, had kids, and bought that house out in the suburbs. Yet, still things didn’t work out.Why was life so unfair?

More importantly, why did life have to be so damn difficult?!?


The Story of Brian

Brian, the “dancing machine”, was so ready to party it up and celebrate life upon graduation. What’s the rush to get a job so soon? After four long, arduous years of engineering, Brian was ready to live it up a little. Knowing that he wasn’t yet made of money, Brian indulged in fun, albeit, cheap fun. He created many lasting memories before he finally decided it was time to start looking for a job.

Unlike his Type A brother, Brian was a lot more laid back. He interviewed at a few places, didn’t get offers, and just brushed it off with a smile on his face. No sweat, he knew his time would eventually come. Finally, in early September, the phone rang and a job offer was on the table. Brian contemplated for a few days… He knew it wasn’t his dream job, but he was in no rush to have everything all at once in life. So, he accepted the job offer and went to work the following Monday.

Brian worked at this first job after college for a few years. In the process, he saved some money and traveled a bit. After the first year, he even took an extended vacation to Maui. The trip to Maui changed Brian’s life. He gained exposure to a whole new world that did not previously exist for him. Unlike his brother, Brian now had a greater appreciation for the simple pleasures in life. Most importantly, Brian learned that he must go through life thinking for himself, instead of blindly following the footsteps of others. Just because someone else did something, did not mean it was the right decision for himself, Brian understood. He had developed a wonderfully open mind.

Three years pass and Brian has progressed in his career. He still had his fun, but he was also getting good at saving money. Everything was going well, but Brian always felt somewhat empty with his lot in life. He liked his job well enough, but he really couldn’t fathom the thought of doing this for the next 30 years of his life. That, and the memories of Maui just wouldn’t fade for him. Brian loved to travel… and he absolutely wanted to see more of the world.

Brian’s Thoughts

With thoughts of Maui still lingering in his mind, one day, Brian finally decided to sit down and figure out what he wanted out of life. Here is the thought process he laid out:

Life is so short, I want to be able to maximize my time in this world. I enjoy a slower pace of life, one where I am afforded the freedom of being able to sit down for breakfast, listening to the birds sing. After breakfast, I love the idea of being able to exercise to get the blood pumping. Being able to take mid-afternoon naps would also be ideal. Late at night, I want to be able to spend time with friends and family, and not have to worry about bedtimes and curfews.

Ok, I know what I want. Now how do I make this happen? How do I buy all the time in the world… How do I get to pay for all of life’s luxuries… without actually having to work?

Brian’s Plan

Brian knew that he needed to acquire passive income. It would be the only way to make his dream a reality. But where to start? Brian had no clue, but he was confident he would find the right answers. He researched into dividend growth stocks, and before the end of the year, he invested $5,000 into a few large-cap, high quality companies.

Generating passive income was fun. Over time, it even became addicting. Brian was enamored with the idea of getting paid for doing nothing. “Hard work is for suckers“, he would now routinely tell himself. He had figured out that the path to riches wasn’t through nose-to-the-grindstone hard work. No, the path to riches was through smart, persistent investing into high quality assets.

Two years later, Brian’s dividend portfolio was on fire! He was now 29 years old and had enough passive income coming in to never have to worry about paying his cellphone bill again. That $5,000 portfolio had evolved into a $25,000 portfolio through consistent investing and reinvesting. Earning 4% annual yield, that was $1,000/year in passive income.

Not having to pay a cellphone bill every month was great, but Brian wanted more. He wanted to eliminate his biggest expense — rent! Brian was paying $800/month in rent, and the thought of making his landlord richer every month was starting to get on his nerves. His landlord never fixed anything up nor improved the place…

Brian’s Plan Evolved

Through research, Brian discovered the world of real estate investing. Initially he was shocked to discover how cheap houses were in many parts of the country! Brian was used to seeing “for sale” signs across suburbs in the Bay Area, with listings regularly going for $500,000 and above for a single family home. Shoot, his brother was just getting into contract for a $638,000 starter home…

Brian was on to something. His inquisitive nature had led him to discover something wonderful… a secret many seasoned investors don’t share with newbie investors:

Rents don’t scale with purchase price.

Brian ran the numbers. He saw for himself what could happen if he invested outside his own backyard:

Property Indiana
Room 3
Bath 2
Interest 4.85%
Price $95,000.00
Downplayment % 25
Downpayment $23,750.00
Loan $71,250.00
Mortgage $375.98
HOA $12.50
Property Tax $60.00
Insurance $45.00
Property Manager $107.50
Vacancy $86.00
Maintenance $86.00
Monthly Payment $772.98
Rent $1,075.00
Monthly Net $302.02
Yearly Net $3,624.23
Cash-on-Cash 15.26%
Cap Rate 8.56%


Brian was banking $1,000/year in dividends with his $25,000 portfolio. But now saw a different path… One that was more risky, but also potentially more lucrative. That same $25,000 could be used for a downpayment which could help him earn $302.02/month, or $3,624.23/year, triple what he was getting through stocks. That would cover almost 50% of his rent! The best part? Someone else would be paying down his mortgage for him. He would own the property free and clear after 30 years.

You gotta take risks while you’re young, right? Brian was all in. He got into contract and secured his first rental property.

Brian’s Plan Evolved Even Further

After one full year, the property was performing just as expected. No real surprises, and some awesome cash flow! Brian was hooked and on cloud 9. He wanted more… He reasoned, if he could just acquire another two properties in Indiana (3 total), he would basically never have to pay for rent ever again! He could even continue living in the expensive Bay Area. He reasoned, if his own rent increased, he would simply pass on the “savings” to his tenants in Indiana to help offset it.

Just for fun, Brian ran some more numbers to prove to himself that his plan to buy out-of-state rentals was superior to his brother’s plan of pouring his life savings into a starter home in the Bay Area. Here’s the breakdown:

Brother’s Home: $638,000
Brother’s Downpayment: $159,500
Brother’s Monthly Rent: $2,525.01

Brian’s Investment Downpayment: $23,750*3 = $71,250
Brian’s Monthly Rent: $800
Brian’s Offset Rent: ($302.02*3) – $800 = $106.06

That’s right. By purchasing just three rental properties in the Midwest, Brian would not only eliminate his rent entirely, he would have an extra $106.06/month returned to him from these investments. By living rent free, Brian knew he could supercharge his savings and buy even more rental properties!

In contrast, his brother had unloaded almost $160,000 into a downpayment that was earning him $0/month in passive income. That’s a lot of capital doing NOTHING to make your life easier. Even worse, Brian’s brother was still on the hook for a $2,525.01/month mortgage payment that could NEVER be missed for the next 30 years!

Brian carried out this thought experiment further. What if he worked really hard to save up the same $159,500 that his brother did, over time? Instead of using it on his own personal residence, what if Brian instead decided to continue investing that money into rentals? How much passive income could he generate?

Plugging in the same rate of return as his first three investment properties, 15.26%:

Brian’s Long-Term Investment Downpayment: $159,500
Brian’s Annual Return: $24,339.60
Brian’s Monthly Passive Income: $2,028.30

Brian’s Revelation

Brian was starting to see the light. By sticking to his plan of making a lot of money in an expensive area, but investing it back into a cheaper location (where cash flow makes sense), Brian could not only cover his ENTIRE monthly rent back home, but also his ENTIRE expenses for any given month!

What a liberating conclusion! By acquiring just SEVEN financed rental properties, Brian would have enough passive income to reach early financial independence!

But what about the future? What about wife and kids? What if the wife wanted to live in the same type of suburban “dream” house that his brother had just purchased? Brian thought for a moment, but quickly concluded, in an expensive area like the Bay Area, renting still makes absolutely more sense than buying!

If Brian wanted to rent the same carbon copy house as his brother, he could do so for about $2,400/month. Since his “downpayment” was generating $2,028.30/month, he could live EXACTLY like his brother for a meager $371.70/month. That’s a far cry removed from his brother’s outrageous mortgage payment of $2,525.01/month. Even better, Brian wasn’t on the hook for property taxes and HOA dues like his brother.

And if Brian lost his job? No big deal, he would simply move into a cheaper location. He had no fears about short-sales and foreclosures. If his tenants lost their job, he would simply find another one to carry on the baton…

What about home ownership? Brian scoffed at that silly concept. His brother was always boasting about how he would own his own home free and clear… Unlike Brian, who was just a renter. But Brian realized, at the end of 30 years, “I’ll also be a home owner. As a matter of fact, with the same downpayment I’ll actually own SEVEN properties, instead of your ONE.” Who’s the real “home owner”?

Brian chuckled. He couldn’t believe no one bothered teaching him this kind of stuff in school. He also realized that his dream of retiring early onto a tropical island was looking more and more realistic.

Brian’s Reality

Ten years go by and Brian sticks to his plan of investing into rental properties. He started off with just one rental, but once he formulated his plan, he knew he had to get to at least seven to secure his financial freedom. Ten years is a lot of time, and through frugal living, continual investing and reinvesting (the snowball effect), Brian was able to purchase 15 rentals in all. To reduce his risk, Brian didn’t put all his eggs into one basket, but instead invested into many different markets across the U.S. His passive income was now over $4,500/month, and although he continued working, he had no fears of being laid off.

Brian’s “Fate”

Why me?” Brian constantly questioned. “How did I get so lucky in life?

Brian was financially free and loving life. Every year, he vacationed with his family. On many occasions, they even visited Maui. At this point, Brian figured he could probably keep working for maybe another five years or so… but who’s counting at this point? The family is happy, he’s stress-free, and life is just wonderful!

He did EVERYTHING he wasn’t supposed to do in life. He did graduate from a prestigious university, but he was pretty lazy at his job, not a go-getter, and he didn’t buy that house out in the suburbs. Yet, still things worked out.Why was life so amazing for him?

More importantly, why doesn’t anyone bother teaching you this stuff in school?!?

Print Friendly, PDF & Email
Sharing is Caring:
0 0 vote
Article Rating
Notify of
Newest Most Voted
Inline Feedbacks
View all comments
Fast Weekly
6 years ago

You didn’t ask to use my story, and you misspelled my name. There is a “y” in there :o) We were taught it because it doesn’t serve anyone elses benefit for us to learn it. Ah buddy, members of our community are just different.

By the way, I’m guessing you pulled those housing financials from your portfolio….right?


Joe S
6 years ago

It is not taught simply because we are taught that the “consumer” creates a vibrant economy. Simply a lie. Continued success my friend and keep inspiring!!


Done by Forty
6 years ago

Just a fantastic angle for this piece. You can write, friend.

6 years ago

What a great way to make your point. Really nice and engaging story too, well done.

I guess I’m a newer visitor to your blog, but am in kind of the same shift as you, starting out dividend investing, but seeing the better ROI in real estate. Now I just need to find some out of state markets to invest in…

Keep up the good fight!

6 years ago

This is such an awesome story brother. Everytime I read your blog it makes me want to hop into real estate investing right now. I seriously just need to sit down and make it happen. I think my lack of education is generating fear but at the end of the day you just have to do it. Keep the great content coming!

6 years ago

Long story, but core point I takeaway is something I’ve told numerous people before (most important in high cost areas). Do not conflate buying a home with making an investment or combine the analysis. If they want to invest in real estate they should evaluate real estate solely as an investment – buying an investment and renting where you live is a valid option. Few have listened, but I have convinced one long term renter who was considering buying not to buy which I consider a win.

6 years ago

Yet another article gently nudging me toward real estate investing! I’m sure you’ve posted about this and I’ll dig around to find it, but what are the top 3 things you’re looking at for potential real estate investments?

6 years ago

Just found your website through a couple internet searches. Great stuff on here – keep up the good work. I ,too, recently came to the same conclusion as you that real estate investing is THE way to go to obtain financial independence. I purchased my first two single family rental homes in 2012, and have had great success managing them myself. I’m not looking at buying my first apartment building (7 unit with commercial store front on the bottom floor). I’m curious as to why you chose 30 year mortgages as opposed to 15 year? I find the biggest struggle… Read more »

JC @ Passive-Income-Pursuit

That was a great comparison. The conventional wisdom isn’t always the best whenever your actually run the numbers. If it was completely up to me we probably would have held off on our home purchase just to have the flexibility in case anything came up. But since my wife has to deal with my job we compromised. And now she’s letting me go after some rental properties which I’m way more excited about. A house can be a huge liability in the wrong circumstance, like Brien’s for example.

6 years ago

I agree that a house can be a liability, but rental properties can be just as bad. The story fails to recount the trials and tribulations of Brienne (Brian and Brien’s older sister), who bought a rental property in Detroit, MI before the car industry went belly up and a mass exodus ensued. As long as you are doing your research and get your property at a good price, whether for personal or investment purposes, you should come out ahead. The problem with most people who purchase a home for their living space is that they let emotion get the… Read more »

6 years ago

Good stories and overall I agree. However, why did you have Brien go through a downturn and not Brian? What happened to Indiana real estate (value of properties, rental amounts) when things turned south around the same time the stock market plummeted? I liked the stories, but I kept waiting to see how Brian would fare during the RE bubble popping and his real estate losing value. Instead, he seemed to go through unscathed. What happens when he gets a bad renter that tears up one of his units? What happens when he buys in the wrong area and the… Read more »

6 years ago

I generally agree with this concept, I have started a similar investment strategy and have 30% shared-equity in one condo and 35% shared-equity in another condo in Arizona. I am 26 and live in northern California paying roughly $450 in rent which is actually covered by my current rental properties. With the cash deals, after fees and maintenance, I would say that my current personal returns have been closer to 6-8% and I would love to start using leverage to make closer to the 15% returns that you have mentioned. I was struggling between whether the cash only real estate… Read more »


[…] personally am looking at getting into real estate investing and am taking a bunch of pointers from FI Fighter who is building a very nice real estate […]


[…] time is just not worth it. So what’s the answer? Earn more! FI Fighter @ FI Fighter writes Dare to Pursue the Unconventional Path (They Don’t Teach You THIS in School) – See more at: … – A short story showing the alternate path in life most don’t […]

6 years ago

Great story!

Why don’t they teach you this in school indeed?! I am guessing even if they did not many kids would have the vision and risk propensity to actually go ahead with it, especially straight out of school. You’d have probably forgotten all about it after you’ve completed 3-4 years of college as well and have all that student debt!

Also, if everyone did it then… you know the rest… 😉


[…] Dare to Pursue the Unconventional Path (They Don’t Teach You THIS in School) @ FI Fighter – If you have never thought about investing in property before, you probably will do after reading this! […]