Several years ago, I met a young couple, Bill and Ann. They were interested in buying their first home, but were hesitant about using all of their savings. Bill was a city employee, and Ann was a schoolteacher. They had great credit scores and had saved a sufficient amount for a down payment, but not much more. They were newly married and planned on starting a family in a few years. Although they both had stable jobs, they were limited in their chosen careers as to how much money they could actually earn. Their concern was they did not want to be “house poor,” a term commonly used to define someone that spends so much on their mortgage, they have little or no money left for savings or other non-essential expenses.

I recommended to Bill and Ann that they consider buying income-producing property as their first purchase. I explained that if they purchased a duplex instead of a single-family home, they could live in one half and rent out the other half. Since the rental income would offset a large portion of their mortgage, they would still be invested in real estate without feeling “house poor” at the end of each month.

Bill and Ann took my advice and purchased a duplex. They were thrilled with the investment; three years later, they sold it for a sizable profit and purchased a triplex, living in one unit and renting out the other two. Four years after that, Bill and Ann started a family and decided to move into a single-family home. The real estate market had seen solid growth in that time frame. Bill and Ann refinanced the triplex, using cash from their newly acquired equity to purchase their new home, while still maintaining cash flow from their triplex. A decade later, Bill and Ann had two children, two dogs, two triplexes, a duplex, three, single-family homes, and an 8-unit apartment building.

I recently received a voicemail from Bill that said the following:

“Hi Craig! I just called to say thank you. I am sitting on my 40-foot Hatteras pulling out of my boat dock and looking back at my wonderful home. Ann and I would have never been able to have this life if we had not listened to you. Thank you.”

Ann and Bill stayed the course. They followed all the rules of the road, and they found their way to Perpetuity. You can too. Let’s get started.

I once had a client, named David, who came to me shortly after his wife had passed away. David explained to me that he and his wife Helen had discussed downsizing, but the thought of moving out of the house they had raised their family in made for melancholy feelings, so the decision to move was continually shelved. After Helen passed away, David’s perspective on the house changed dramatically. The house had become a sad reminder of a loving partner and a life gone by. David was finally ready to move. David and Helen had owned their home for over 20 years, and they had seen strong market appreciation over those two decades. David wanted to downsize from four to two bedrooms. He also wanted to be on a single level as the stairs in his current home were wreaking havoc with his knees. Most importantly, he wanted a view of the ocean and to be geographically closer his daughter.

David contacted me about selling, and he was pleased when I told him the value of his current home, but he was shocked when I told him what the average list price was for a condo fitting his search criteria. I suggested David speak with both his financial advisor and his accountant before making the decision to sell. A day later, David called me back with the sad news that he simply could not afford to move. I asked what the issues were. David’s financial advisor had told him that the purchase of a new home would greatly increase his property taxes and in turn make his cash flow far too tight.

I asked David if he had spoken to his tax advisor. He had not. I suggested that he contact his CPA and discuss Proposition 60, which allows a California homeowner over the age of 55 to transfer their tax basis with them a single time if they purchase a primary residence for equal or lesser value (there are, of course, other restrictions and rules, but that is the basic take). Two days later, David called me back with the mixed news that although the Proposition 60 would help to greatly reduce the monthly cost of his desired new condo, his accountant felt the association dues were too high for David to take on with his fixed income. Again, David was distraught. He truly wanted his ocean view condo near his daughter. Now I was distraught, too. I could hear the sad disappointment in his voice. David’s lack of cash flow was stopping him from living out his golden years in his dream home closer to his family. Money was the issue, but in this case, money was also the answer.

I reminded David that the first $250,000 in proceeds from the sale of his house are tax-free (shockingly, his accountant had failed to mention this to him, yikes!).

I suggested that David buy his dream home and an income-producing property; the proceeds of which would offset the cost of the high HOA dues on the condo. He liked the idea, and after a little more research, he called me back and excitedly said, “Let’s do it!”
I listed David’s house and quickly found three qualified buyers. Next up was the income property search. I located a two-bedroom condo in a college town that had great rental history. David used his $250,0000 of tax-free gains from the sale of his home to purchase the condo. The rents from the investment property easily paid for the expense of that property with enough left over to cover the expense of the condo’s HOA dues plus a little extra to put in his pocket every month. The cash flow off the condo and the anticipated annual appreciation of the property far outweighed the ultra-conservative bonds David’s financial advisor had originally suggested he invest in. David got his dream condo and cash flow in Perpetuity. David also got a new accountant and a new financial advisor.

Jill was an entrepreneur, and after having built and sold two successful businesses, she decided it was time to tackle real estate investments. She decided to get her real estate license and aced the test the first time through. Jill planned to buy a property and be her own agent; thereby earning the commission herself and recouping part of the out-of-pocket money she would need for the down payment. Jill liked the south side of town, and she knew it was a desirable rental area since it was near both a hospital and a college. Jill found what seemed to be a great building — five single units all in seemingly good condition. Jill negotiated with the listing agent and was pleased to get the property for 10 percent less than the asking price. Jill’s father was a retired contractor, so Jill decided to ask him to inspect the property. He had built over 40 homes and was excellent at his job. Jill’s father made a list of some minor repairs, and Jill negotiated with the seller’s agent to repair nearly the entire list of items her father had called out.

Next up was the loan. Jill contacted her bank and a few other lending institutions that had been recommended by friends and most of the quotes were fairly consistent on the cost and terms of the loan. Then, Jill heard a radio advertisement for an online lending company that advertised an unbelievably low rate. Jill called, and in minutes she was convinced this was the correct route. Vince, the lender for the on-line company, quoted her an amazing rate with almost no out-of-pocket costs. Jill reviewed her notes and then re-contacted all of the lending institutions she had spoken with to see if they could beat or even match Vince’s deal. None could come close. Jill filled out the online application and had Vince begin to process her loan. Being a diligent real estate agent, Jill went about removing her contingencies one by one. However, she ran into her first snag when the appraisal did not come back from the lender on time. Her appraisal and loan contingency periods were nearly up. Jill requested an extension, explaining to the listing agent that the appraisal process was taking longer than expected. The listing agent explained to Jill that the owner was doing an IRS 1031 exchange and was already in escrow on his next property. The agent further explained that there was a backup offer in place for all cash and that this other buyer was now more desirable than Jill to the seller since the all-cash offer could close almost immediately. Jill was issued a “notice to perform,” which stated that as per the purchase agreement, she would need to remove all of her contingencies within 48 hours or she would be in breach of contract, potentially giving the seller the unilateral right to cancel the transaction and go with the other buyer.

Jill called her Internet lender and was told that Vince was no longer with the company. She asked who was handling his files and found out his clients had been divided up among several different online agents at the company. Jill’s file could not be immediately located, but Mr. Nelson, Vince’s superior, assured her he would personally get back to her within 24 hours. After two days went by, Jill called and was told Mr. Nelson had left on vacation and would not be returning for 10 days. Her sale was scheduled to close in 17 days. Another supervisor got involved two days later, and her file was located in underwriting. When Jill asked who was covering for Mr. Nelson while he was gone, she was told, “Oh, you can just talk to any of us.” Each time Jill called, she got a different representative, and the answer was always the same, “Your file is still being reviewed in underwriting, give it a day or two.”

Knowing that there was another anxious buyer waiting in the wings, Jill did not want to let this property get away. She decided to make a business decision. She removed her contingencies in order to honor the contract and move the transaction forward. The next day, Jill heard back from the online lender. The property on which she had a contract for $592,000 only appraised for $510,000.

Jill also found out that since the building had five units, she would need a commercial loan, and the rates for commercial loans were higher than the loan rates originally quoted to her over the phone during her initial call. If Jill tried to cancel the escrow, the seller could sue her for damages, and she could potentially lose her 3 percent deposit. Jill decided to continue with the transaction and had to come up with an additional $77,000. Between borrowing from her 401K and her parents, Jill was able to raise enough money to close the escrow.

Shortly after taking ownership of the building, one of Jill’s tenants gave notice. During the walk through of the unit, Jill noticed the refrigerator and stove were gone. The tenant informed Jill that she owned those items and had the right to take them with her. The owner had not informed Jill that most of the tenants owned their own appliances. Had Jill requested estoppels, she would have learned this fact before moving forward. She would have also learned that each tenant had paid two months security deposit plus last month’s rent. The seller had not informed Jill about that either, and Jill had not reviewed the leases properly. These oversights cost Jill thousands of dollars, but it was peanuts compared to the tens of thousands of dollars it cost Jill to replace the cracked foundation her contractor / inspector / father had not detected during his inspection of the property. Had Jill properly studied the rental history of the property, she would have noticed a high turnover rate and high-vacancy factor. Had Jill understood the type of building she was buying and the area she was buying in, she would have factored these issues into her offer. If Jill had known how to correctly evaluate a property based on the historical data of the recent comparable sales, she would have never made such a high offer in the beginning or possibly never made an offer at all on what she once thought to be “an amazing deal.”

The good news is that eventually Jill sold the property and broke even. She reinvested her equity back into real estate. When Jill next purchased, she hired an experienced local agent with extensive market knowledge. He introduced her to a qualified lender, a well-trained property inspector, and an exceptional management company. Jill has stuck with her team ever since. She is now the proud owner of three apartment buildings and is currently in the market for her next property.

Joe decided to become a real estate baron. His friend Michael was making a killing flipping houses, and although Joe did not know anything about real estate, he did know one thing for certain: He was much smarter than Michael. If Michael could do it, he could do it better. Joe searched the local paper and found the “#1 Agent” and “Local Expert.” He made the call and explained that he was ready to start flipping houses. His agent assured him he had made the right call and told him about an “amazing deal” that was about to come on the market. The agent explained he had just gotten the listing and that no one else knew about it. He told Joe it would move fast, and if Joe was a serious investor, this was absolutely the deal to start with.

The pro forma numbers the agent presented to Joe indicated amazing upside potential. Joe’s agent assured him if he got the rents up and did a little paint and carpet fix-up, Joe could flip the property quickly and make a killing. Joe was eager to begin his new career. Although both the price of the property and the down payment were substantiality higher than Joe had originally wanted to spend, Joe’s agent assured him it was a great investment and if he hesitated, it would be gone. Joe instructed his agent to write an offer; after just two counter offers, he had the property under contract. When the transaction entered the appraisal phase, Joe was shocked that the property did not appraise for the sale price. Joe’s agent, Michael, continued to tout the pro forma numbers on this deal, pointing out that the rents were absurdly low and backing up his statement by showing Joe ads for other similar rental properties in the area that charged much higher rent. Joe felt confident in working with the #1 agent and decided to take his agent’s advice. He accessed a six-figure line of credit on his home to make up the difference on the appraisal, thereby falling within the underwriters’ lending requirements. Joe closed escrow on the property and planned to raise rents quickly to what he had been told was market value. The plan was to use the increased cash flow to pay off the line of credit quickly and be profitable in a very short time. Instead, Joe came to find out that the building he purchased was under rent control, and although his agent was correct in stating the units were “under market,” Joe was extremely limited in how and when he could raise rents. Joe was finally able to raise the rents, but the process took years not months.

In 1964, Betty and her husband Robert decided to purchase their first home. They were torn between an 1100 sq. foot home with two bedrooms and 1.5 bathrooms on a 30 x 90 lot in Manhattan Beach just a few blocks from the sand, or a slightly larger 1250 sq. foot home with 3 bedrooms and 1.5 bathrooms on a 50 x 150 lot, a few miles inland in Redondo Beach. They carefully weighed the pros and cons of each purchase. The Manhattan Beach home was priced at $27,000, and the Redondo Beach home was priced at $21,000 — a 30 percent difference in price.

Betty liked the spacious lot in North Redondo Beach, and she liked the idea of the third bedroom. They were planning on having a family, and more bedrooms with a big backyard seemed like a better fit. Robert liked the proximity of the beach. He thought the smaller house was sufficient for their first home, and if the family grew, they could add on a bedroom or even two by adding a second story. Betty argued that a big backyard would be important for children. Robert countered that with the beach just two blocks away, the smaller house actually had better outdoor space. Betty did not like the fog that rolled in every morning and typically hung around until midday. She said it depressed her, and since she would be staying home with the kids, she wanted to be further inland where sunshine was more consistent. Robert finally relented with a promise from Betty that someday, they would move to a beach cottage after the kids moved out.

Robert and Betty stayed in their 3-bedroom, 1.5-bath home in Redondo Beach for almost 40 years. Robert died in 1996, and his wife Betty died a few years later. I never met either of them, but I heard the story from their son Lawrence who had asked me to sell the house. We listed the Redondo Beach house at $625,000 and received three offers. I was able to negotiate for the full asking price. Shortly after we opened escrow, Lawrence asked me what the little beach cottage his father had wanted would be worth in today’s market. All I said was that those properties had shot up quite a bit. I did not have the heart to tell him what he most likely already knew. The little beach cottage was located in the highly desirable area of Manhattan Beach. The land alone in that area was worth over $2,000,000.

Elizabeth and Howard met in their 20s. The two dated for a few months, and when Elizabeth told Howard she was pregnant, the couple decided they were meant to be together and married. After a few years passed, it became clear their marriage was amicable at best, but not fulfilling for either, so when their daughter completed college and moved across the country to start a new job with her fiancé in tow, Elizabeth and Howard decided it was time for them to go their separate ways. Howard was a few years older than Elizabeth and was very settled in their home of over 20 years. Elizabeth was in her early 50s and wanted a carefree lifestyle — no yard, no pets, and lots of travel.

The couple did not hire a divorce attorney. They simple sat down one morning and discussed how to split their assets. The couple had joint savings and checking accounts. They decided that they would close the current accounts, and each partner would take fifty percent from each account. Easy.

Next up was their individual IRAs. The couple had not seen great returns, and each had a different vision for the money. They decided to leave their respective IRAs in place and not touch them unless their daughter needed money. Each of them had a pension from their individual careers, and they decided each would keep their own pension cash flow as their sole and separate incomes.

Next up was their real estate. The couple owned two properties, both free and clear. The first was their primary home, which had been dubbed “The Nest” and the second was a six-unit apartment building purchased as a safety net, which they nicknamed the “The Net.” The couple called Barry, a trusted friend who was a real estate agent, and asked him about the value of the properties. Barry was familiar with both properties. He estimated the house to be worth approximately $850,000 and the apartment building to be worth approximately $925,000. The couple decided that since their daughter would inherit both properties eventually, the $75,000 difference in equity was a non-issue. They met with their CPA as to how best to transfer title without triggering a new tax basis, and within a few weeks all of their finances were separated.
Elizabeth was excited by her newly found freedom and ready to start fresh. She had worked diligently at her job for 30 years and earned a company pension backed by her former employer. Between the cash flow of her apartment building and her pension, she planned on a very luxurious life style.

She rented an apartment on the Wilshire corridor with a view of the Hollywood Hills and a doorman. Next, she leased a dream car — a convertible BMW.

After a few months of not working, Elizabeth was getting a little bored, so she spent the morning searching the Internet for the best airfare deals to Spain. She found a great price on two business class seats to Madrid and called her friend Debbie to talk about booking the trip they had always dreamed of. Debbie said she would love to go to Spain, but she suggested Elizabeth watch the morning news before they talked about booking a trip.

Being more focused on her Internet airfare search, Elizabeth had not yet caught the big story of the day. The company she at which she had worked for decades was in big trouble. Images of the CEO and other top executives rushing into limousines and avoiding reporter questions on fraud charges were playing over and over on every channel. In a relatively short time, the company Elizabeth had worked most of her adult life for folded and so did her company-backed pension.

Elizabeth was counting on her pension for her monthly bills. She had spent most of her cash on new furnishings for her apartment, her car, and a five-star ski trip. Her bills were piling up almost as fast as her savings were dwindling.
Luckily she still had “The Net.”

Elizabeth called her ex-husband Howard. The two met for lunch, and Howard worked out a plan for Elizabeth. Her apartment building had a newly vacated unit. If she moved in there, got rid of her Wilshire apartment building, and downsized her car from an $800-a-month BMW to a $325-a-month Accord, she could afford to continue to live on her own.

The cash flow from “The Net” kept Elizabeth in a comfortable lifestyle and even got her to Madrid, in coach.

Christina and Ryan starting investing in real estate when they were in their early 20s. Christina was a top-selling real estate broker who had an eye for good deals. Ryan worked for an airline. Together, they made a solid income, but neither of their jobs had any retirement components. Investing wisely was their only path to retirement. The couple had been diligent investors and obeyed the rules of the road. They bought properties that were distressed or poorly managed, and they turned them around. They utilized IRS 1031 to grow their portfolio and defer taxes to the future. They understood the concept of “value adds”; they knew how to improve a cap rate; and they also knew when to trade up. Their portfolio grew at a nice, slow rate.

Christina decided that the “slow” part was a problem. She convinced Ryan that it was time sell some of their real estate and invest in the stock market.

The couple decided to call Steven, a trusted family friend who had steered her parent’s portfolio for many years. Christina and Ryan signed up with Steven and his brokerage and within a relatively short time, just as Steven had predicted, the couple’s portfolio began to grow much quicker than their real estate holdings had been appreciating. The couple sold their income-producing property and began investing heavily in the stock and bond markets.

Some of their stock and bond portfolio were paying dividends, and they quickly re-invested those proceeds. The market began to really heat up, and the returns became intoxicating. The equity in their home had also grown nicely and in anticipation of future market growth, the couple decided to take out a second mortgage and begin remodeling their home. Soon after the remodel began, Christina found out she was pregnant. The couple was overjoyed.

The year was 2008, and much of Christina and Ryan’s portfolio was connected to subprime mortgages. When Lehman Brothers crashed, so did Christina and Ryan’s finances. Real estate sales slowed to a near halt, and the airline Ryan worked for began downsizing. Ryan was laid off. The remodel was costing double what the couple had budgeted, they were eating through their savings at a frightening speed, and the baby was due in a few months.

With Ryan unemployed, real estate sales evaporating, and dollars flowing out (not in) to the couple’s household checking account, Christina and Ryan decided to tap their $100,000 credit line on their home. When they contacted the bank to access the credit line, they found out the line of credit had been cancelled, as per the lending institution’s sole prerogative. Banks were no longer giving away money. To complete the remodel, Christina and Ryan tightened their belts, sold one of their cars, cancelled the cable, and clipped coupons. They finished the house, but their finances were also finished.

Christina told me the reality of their situation hit her in a grocery store while she was standing in line to buy diapers. Both credit cards were maxed out; her ATM was declined; and there was no cash in her purse. Unable to pay, she froze with embarrassment for a moment, as did the checkout clerk and the customers behind her.

“Put those on my bill,” the woman behind her said.

Christina remembers thanking the woman and leaving the store embarrassed, but also focused.

She got home and said to Ryan, “We need to sell the house.”

Ryan simply nodded. It was time.

The house sold quickly, and Christina and Ryan were left with enough money to buy a new, smaller home. Instead they decided to wait. Christina knew the worst was not over yet in the real estate downturn. They rented for a while, and Christina got a new job. Ryan stayed at home with their daughter. After a few of years, the couple decided the market was about to turn again. They bought in 2011; soon after, the market caught fire. Christina went back into real estate, and within a couple of years, they were rebuilding their portfolio.

Today, they are settled into their new home and own a small apartment building they recently purchased at a great cap rate. They plan to buy one investment property every other year, if possible, until they get to 10 buildings with a minimum cumulative annual positive cash flow of $100,000. In time, they will be enjoying their own Perpetuity, along with their wonderful daughter Sophia and new baby son Justin.

It took Christina and Ryan years to get back to where they already were before taking a side trip. The moral of the story is: You have a map. Use it! NO SIDE TRIPS! They are too expensive and usually not as fun as advertised, so why bother?

Twenty years ago, I had a client named Jason. He had just moved to southern California from upstate New York. On Jason’s 30th birthday, he and his twin brother Jasper were given an amazing opportunity. Their parents offered each of them $50,000 towards the purchase of their first home.
Jasper wasted no time and was under contract for a home within two weeks of the offer. Jason was reluctant about the idea of homeownership, but his trusted twin Jasper encouraged him not to miss out. Jason and I set out a few days later to find his first home. We looked at everything on the market for several weeks, and although we found a few suitable properties, Jason finally decided homeownership was not for him.

“Why?” I asked.
“I really like my freedom.” Jason replied.

I then peppered the conversation with all of the financially sound reasons to buy real estate, not the least of which was his parent’s offer to give him the down payment.

“I already told my dad I’m out for now, and he said the offer will be good when I’m ready.”

A few months later Jason met Alan, the man of his dreams, and the two moved to Hawaii. After Jason moved, he and I exchanged a few Christmas cards but after a couple of years, we lost touch.
Years later, I ran into Jason by chance in an airport. We both had a little time before our flights, and we caught up over a cup of coffee. Jason told me that he and Alan had lived in Hawaii for a few years, but ultimately settled in Seattle. I asked if he had ever taken his parents up on the offer of the down payment on a home.

“No,” he said. “One of my biggest mistakes was not buying a place when I had the chance.”

Jason told me that his father’s seemingly solid financial position had melted down rather quickly when he discovered his business partner had been embezzling. Jason explained his that his father’s former business partner leveraged most of the company’s holdings into a series of bad investments. Then, when it became apparent that he could not pay the debt back, he syphoned off all the remaining cash before disappearing.
Since Jason’s father owned the company 50/50 with the former partner, his father decided to do the right thing and sold off what he could salvage from the company. He then used most of his personal assets to pay back investors and debts. Jason’s father avoided any lawsuits but was left with very little in the way of personal wealth. To make matters worse, Jason’s mother had died last year, and now his father was showing signs of early Alzheimer’s. His doctor recommended that he enter a care facility. Jason’s brother Jasper had three children, and he and his wife both worked full time, leaving the couple little to no discretionary time or income to put towards their father’s care. Jason and Alan would be covering the costs on their own.

Jason lamented on the offer his father had made so many years ago.

“I wish I had taken my dad up on the down payment to buy a place. My brother was the smart one. His mortgage is nothing. I really should have bought when I had the chance. The care facility for my dad is crazy expensive. I doubt I will ever be able to buy a home now. Woulda, shoulda, coulda.”

As you might imagine, I had a few thoughts to share on the subject of his future ability to buy a home, and we spent our last few minutes discussing his current family and financial situation. I mapped out a few ideas as to how he and Alan could afford to get into the real estate market. I suggested Jason speak with a real estate agent I knew in Seattle. Jason and I finished our coffee and headed for our respective flights, promising this time to stay in touch.

I recently received an email from Jason that he and Alan were doing well and had settled into their new home. In the email, Jason explained that he had worked with the agent I suggested to lay out a plan for using Jason’s income as well as his father’s social security income to create a blended household where Jason’s father could live with Jason and Alan as opposed to a care facility. The numbers worked and so did the living situation.

I received a Christmas card from Jason last year showing all three of them in horrendously bad Christmas sweaters in front of a roaring fireplace.
Jason scribbled across the front just three words — “Home at Last!”

In the late 1980s, I scraped together every dime I had, and along with two friends, Cindy and Shawn, I purchased my first piece of investment real estate. I was 26. The property consisted of two, tiny houses on one big lot in a suburb of San Diego. The rents covered the majority of our mortgage, taxes, insurance, and maintenance.

A few years later, I purchased my first primary residence, a condo in Hermosa Beach, California.

I held both properties through a short market cycle and saw a dramatic upturn in real estate values; both properties had taken a nice ride on the equity train. I began building my portfolio by utilizing the IRS 1031 tax exchange and traded my San Diego property for an income property with better cash flow.

I then refinanced my primary residence and pulled cash from my equity-rich Hermosa Beach property to begin increasing my portfolio via leveraging. I was on the path. I started with a small fix-and-flip and then reinvested into duplexes and triplexes. I moved into larger properties. Next up was a five-unit building, followed by an eight-unit building. Then came a 15-unit building, and then a 22-unit building. My portfolio was growing nicely, and I was on the road to Perpetuity.

But then I took a side trip. With a hot stock market, I refinanced and pulled out cash to buy “can’t miss” stocks. Then, I ventured into tenant-In-common deals run by a company with an amazing track record. The stock market failed as did my stockbroker’s “can’t miss” stock picks. Worse yet, the tenant-In-common company I had invested heavily in turned out to be a Ponzi scheme. My “side trip” cost me more money than I care to admit and set me back at least a decade. I knew the rules, but I thought I could bend them. Never again.

Follow the simple “Rules of the Road” laid out in this book, and then sit back and wait for the equity train to arrive. Given time, rents go up, values go up, and so do your profits.

Success will be yours if you simply stay on the path and remember to keep the ultimate goal in mind. Cash flow for life. An annuity without end.