Why I Wanted To Build A Real Estate Empire

Why I want to irrationally build a real estate empire

In 2002, I was one year into my new job in San Francisco when I decided I needed to build a real estate empire. The dotcom collapse was traumatizing and I wanted to own real assets with more stable cash flow.

After a couple years, my desire for real estate increased. I want to own a real estate empire so I could retire early and live off the income. But then the housing crisis hit, ruining my confidence that I would one day be free.

Now things are lollipops and roses. Rental income is strong. Valuations are at all-time highs. Mortgage rates are now at all-time lows.

Yet, rental income has dropped to below 10% of my overall income. At the same time, owning physical real estate has become my main source of stress. As a father of now two young children during a pandemic, the last thing I want to do is manage tenants and deal with maintenance issues.

To maximize lifestyle and profits, I should rationally sell all rentals while valuations are at all-time highs and focus my attention on building an online business since it's more fun and profitable. As we've seen through the pandemic, any business that can't be shut down has dramatically become more valuable.

Despite the logic, I refuse to sell my entire rental property portfolio because of one main reason: insurance against a difficult life for my children.

Life May Get Brutally Difficult For Our Children

Owning a real estate empire is one of the best ways to hedge against a difficult life for my children. Let's go through why life will be harder for our children.

Getting Into University Is Hard

Follow any college admissions acceptance record and you'll notice a steady decline over time due to a rise in competition. Average GPA and SAT scores for elite schools have never been higher, yet getting in has never been harder. Kids of all races are realizing the frustration Asian kids have been going through for years now.

Record Low College Acceptance Rates - Why I Wanted To Build A Real Estate Empire
90%+ of you won't get into a prestigious university, and that's OK.

Getting A Great Job Is Impossible

Read any media publication, and there will be articles droning on and on about how prohibitively expensive it is to live in any major city. It gets incredibly depressing, especially for young people looking to establish roots.

Observe who gets a job at all the sexiest startups and highly coveted organizations. They all come from the same elite schools over and over again, yet many still complain how they are just scraping by.

Life seems like it's only going to get MORE competitive with globalization, not less competitive. Our children need lots of luck and parents who plan way in advance for tough times.

By definition, only 10% of the working population gets to be in the top 10% income earner bracket. And only those in the top 10% earn an income of at least $115,000 a year according to the IRS.

I could choose being in the top 25% ($68,000) as a income goal for this article, but it's very hard to get ahead living in a big city when you need to pay $2,500+/month in rent or $1.2M+ for a median priced house. Of course nobody needs to live in an expensive city to get ahead, it's just nice to give our children as many options as possible.

Related: How Much Do The Top Income Earners Make By Percentage

Our Kids Have It Rough

Given there's a high chance my son won't get into a top 25 college, won't land a job at a top 50 company, and won't make a top 10% income, he might get thoroughly bummed out with all the rejection since he'll grow up with peers who will. Maybe he'll end up just asking us for help during his entire adult life!

Further, there's a chance my son's visual disability (nystagmus) may make it tougher for him to learn or be treated well by others. It's too early to tell, but I'm hopeful his nerves and cells are just slowly developing and he'll turn into a completely healthy boy

It'll be incumbent on me and his mother to encourage him that it's OK if he attends city college, works at Macy's, and makes minimum wage so long as he's tried his best. I really don't care what type of career he has so long as he's helping other people and finds his work rewarding. But I fear that even with our reassurances, he may not be happy.

Life has an incredible way of beating the most optimistic of us down. We like to compare our progress to others, which inevitably makes us unsatisfied.

Two Reasons For A Real Estate Empire

Once you have your living expenses covered, you can live in any of the most expensive cities in the world and be OK. By being able to provide subsidized housing (if necessary) for my son in an expensive city like San Francisco, it'll open up more opportunities.

Subsidized Housing Makes Life Easier

I know so many people who are deterred from moving to places like New York City or San Francisco because of high housing costs. What a shame to be unable to pursue a dream due to cost.

Post-pandemic, I think big city living is going to BOOM again. As a result, job opportunities and real estate bargains will be soaked up.

After being away from the workforce for the past five years, my #1 joy from not having to work is not having to commute. It would be nice if he didn't have to spend three hours on the road a day to work at a job he doesn't love.

90+ minute commutes have risen due to the cost of housing increase

Real Estate Empire = Job For Kids

The second reason for owning multiple pieces of property is to give my son or daughter a job if he or she one day ends up jobless. I have this fear that he might not even be able to get a cashier's job at Macy's because Macy's might not even be around in 23 years. Perhaps the robots will eliminate the need for most lower income jobs we have today.

Also, what if the Macy's hiring manager is prejudice? What if his disability keeps him from getting ahead? We always hope for the best for our children, but the reality is they seldom achieve their best lives without a little bit of luck and help.

Related: The One Ingredient Necessary For Financial Independence

By having a rental property portfolio to manage, I'm hoping that if all else fails, my son can take pride managing a family asset that might one day be his.

He'll learn about real estate, negotiations, property management, people management, market trends, and so much more. I will be the most patient and loving mentor to him. From there, he might be able to build his own real estate empire.

Less than 50% of the population can afford housing in the coastal regions where many of the jobs are

A Parent's Job Is Never Done

Nobody really told me how much you worry as a parent. It's rather debilitating if you can't get past thinking about all the things that could go wrong with your child, especially things that aren't fixable due to genetics. The only thing we can give our children is lots of love and support.

As parents, perhaps the right thing to do is focus on living our best lives now so that our children can also have the best lives possible now and in the future.

It's counterproductive managing a rental property for a couple decades so my son can one day use if it's taking quality time away from us now. Having all these hopes and dreams for our children without giving them a chance to explore on their own is unfair.

Good thing that buying rental properties today is a financially savvy move. The value of cash flow (rent) has gone way up because interest rats have come way down. It takes a lot more capital to generate the same amount of risk-adjusted income.

I just don't want him to fall through the cracks. Perhaps gutting it out at a miserable job will build character. But maybe all a miserable job will do is make him an aimless vagabond who is bitter at the world. You should see the Twitter feeds of real estate reporters who rent. It's just misery after frustration after indignation.

It worries me if he has to go through all the things I went through to get ahead. I don't think I could do it again if I had to start over. Further, so much of my accomplishments were directly attributable to luck. Good thing our children are more resilient than we think.

Of course I won't tell my son of this escape hatch plan until he's ready. Then he might get completely demotivated to make it on his own.

Only when he's tried his best and is down on his luck will I invite him over for a beer one evening and say, “Surprise son! Everything will be OK. We're so proud of you. We've got something awesome that we hope you'll enjoy doing.” He'll have no idea what'll hit him because he'll have grown up in a regular old house with frugal parents.

Related: How To Invest In Real Estate If You Don't Want To Own Property


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88 thoughts on “Why I Wanted To Build A Real Estate Empire”

  1. Wendy Martens

    I am amazed at how you great of a father you are. You are planning for future generations. This is the value every father should strive to achieve.

  2. Chinga Reddy

    The best thing my dad did for me was instill fear in me, fear of failing, fear that I will end up sweeping the streets, made sure that I know I’m on my own and that he will NOT be there for me. Growing up, there was never a day I did NOT hate him or wished he would return home late or maybe not return home. My mom even though stayed home was emotionally never existent. She used to tell me how great she was because even though she did her MS from a prestigious college, sacrificed her career so that she can take care of me. They were miserly but would tell me they were being frugal because if I did not get into a good school they will need the money to pay for private school. I was compared with every kid they knew of and how great that particular kid and worthless I was. As a kid, i NEVER got a single gift from my parents. ZERO. Now that I’ve succeeded in life, I feel like an imposter. I am in the top 1% (AGI) in the US, have a loving wife and an adorable year old kid. I have a huge home, drive a German car, pay an annual tax over 3 times the average salary in the US. I am not happy and wonder everyday what would make me? Take home point, love your kids, be there for them, guide them on what is right and what is wrong and as Sam says teach them not to fail due to a lack of effort.

  3. Interesting, Sam. I can definitely empathize with kids being central in every decision you make. I’m in the same boat with my two young ones.

    But I think I’m in another world when talking about the issue with high-priced housing in big cities and with elite universities. I grew up in Atlanta metro and went to school at Clemson University (state school) on a football scholarship. So, those experiences mark my perspective.

    But I did look at ivy leagues and had a chance to go there. And I’ve had chances to live in the big cities. But in both cases I gravitated towards smaller, up-and-coming areas (like the small southern university town where I built my rental portfolio).

    I guess all of that to say I don’t see the increased competition at universities or increased price in big cities as a bad thing. I see it spilling over and people moving to all sorts of other, cool, more affordable places in other parts of the country and the world. Remote work is getting easier and easier. Even here in Ecuador where we’re living this year, American and Canadian money is spilling over because of all the expats who’ve moved here (earn there, spend here).

    So, I think our kids will be fine because the pie has gotten a lot bigger. Opportunities are spilling over into new places. And the rest of the country and the world has plenty of fascinating paths to explore.

    PS – what’s your comment plug-in. I love it!

  4. Sam if you are talking about amblyopia, I unfortunately is afflicted with it. My parents didn’t discover it until I was 7. To this day my left eye vision is very poor.

    I am horrible at golf because of poor proprioception and depth perception. I also suck at baseball. Cannot field a fly ball st all. But I am actually ok at other sports where my insight into the nature of the game compensates for my visual defect. I am a decent shooter and passer in basketball.

    I also went to a top 15-20 university so it didn’t affect my academic performance too much although I probably would not try to be a surgeon lol.

    I am sure your kid will do great. Correcting it so early plus modern technology. And even if he had slight visual impairment at worst he’ll be like me making top 5% income.

    1. Howdy JAck, thanks for sharing. Yes, it could be something to do with the brain and eye not working correctly together, hence his lack of ability to fixate his eyeballs on a focal point for a long time. I’m assuming that a lot of it is just him looking around, developing, wondering, etc. And hopefully technology and new techniques and things we do now can help him see better in the future.

      Good thing about golf is that it sucks. Takes too long, costs too much! lol. And with baseball, how many times are we gonna play pickup baseball as adults? Have you tried tennis though? hmmm.

      Glad things have worked out for you! I’d love to learn more about your story offline or through a guest post if you are willing. I cannot get enough of people overcoming any sort of impairment and leading a good life. I love stories of motivation and hope!



  5. Hi Sam.

    My brother was born squint and the local doctors wanted to operate and fix it. At the time, my grandfather was undergoing treatment for his deteriorating eyes (diabetes) in another city. A doctor at the specialist hospital noticed my brother and his squint in the waiting room and stopped to examine him. After a few minutes, he advised my parents NOT to have the operation done as my brother’s eye would straighten after the bridge of his nose matured a bit more. And sure enough, when his big nose grew in, his squint corrected itself. Second opinions are a must!

    Stay positive and remember kids are resilient. He might just outgrow it. Also, he’s already leaps and bounds ahead of every other kid out there. He’s got a financially savvy family unit! Whereas the rest of us dense hamsters have to struggle with understanding Personal Finance 101 and overcoming financial fear at 34.

    Even if he has a disability, so what? I’ve seen plenty of disabled people who are more ambitious, more driven and more capable than some able bodied people. Disability seems to breeds grit, determination and strength.

    You’ve mentioned that entrance to university is getter harder and harder. But have you considered that if your son has a disability, he may have an easier time getting into a prestigious university (or even employed)? I know that it forms part of the entrance quota. So maybe where you’ve failed, he’ll succeed?

    Wishing you and your family all of the best!


    1. Thanks for sharing this hopeful piece of news QK. We’re definitely hopeful that his eye muscles will get stronger and his brain and ocular nerve will coordinate better as he ages. After all, he’s just a few weeks old and an ophthalmologist told a parent whose daughter had eye issues that it takes a person about 7 years to fully develop their vision/eyes.

      Both of us have poor vision (glasses/contacts), so it’s not a surprise he may have poor vision. We just feel bad and some guilt for passing on such poor genes to him. But we’ll get over it and love him as much as any parent can. Whatever his condition turns out to be, we’ll always be there for him!

  6. I have some rental property and have been considering purchasing more. However, one thing that gives me pause on building a long-term real estate empire (besides the infrequent headache of a bad tenant since I primarily own Class B properties) is the potential impact of 3D printing on the housing market. I think banks, existing homeowners, and governments have reasons not to encourage 3D printing, but you have to think it is going to have some impact on costs and existing real estate valuation on a multi-decade timeframe. I’m curious to know how you are considering this risk with the rest of your thought process. Love your blog. Keep up the great work!

    1. Class A is too much for me. Class C is a surprise repair waiting for me every 3 months. 3d printing houses is interesting visually. But we have to remember there is a reason or reasons why wide spread adoption is not happening. Will it happen maybe you are right but you’re investing and locking in your majority of $ against 5,10 or 20 years into your future.

      Apply this exact logic against retail stores replaced by online shopping. And traditional rentals of an entire floor or 3 of unfurnished commercial real estate with you cycling to the local furniture stores oneself being replaced by well thought group workspaces where you can rent by 6 or 12 months contacts, a desk, an office depending on your budget and needs that is inclusive with amenities of snacks, drinks, group activities, security guard, group discount on great furniture, network of investors businessmen. These exist but to what % of the total of 100%. And will it increase, or stay the same at a future date. This is what I mean by commercial properties and retail properties changes underway.

  7. Its normal to worry about our kids but I hear it never ever ends, so its best to have some sort of coping mechanism for the constant worry.
    Warren Buffet did say he doesn’t spoil his kids in anyway EXCEPT one, and that was to provide them the best education available (notice he didn’t say the most expensive) to them.
    I believe that is the best thing to do as well and it would go very much further than giving them something that makes their life easier (eg. real estate, a built up business, cash etc.).
    Many parents out there have built up their own businesses with the hope of their kids taking it over but anecdotally, most kids don’t take up the offer.
    My dad offered me a spot within his business once he retired but my first response was no thank you, to me it just seemed wrong to get something like that on a platter and have to work with other business partners who may have worked as hard as my dad but to see his kid take his spot without effort. Its been 20 yrs since the offer, and I don’t regret it at all. All I’ve achieved, I’ve done it on my own (apart from the education that I was provided for by my parents). Its something to be proud of. I am since extremely grateful and thankful to my dad who had the faith in me or trust to takeover the company. The thought counts and he knows that.
    I see someone like Trump, who obviously had lots of help from his dad and is no doubt a shrewd businessman himself, but that leg up will always be hanging over his head (or maybe not, depending on his personality which I think he genuinely did it all on his own).

    All kids are different FS, I think rather than take the risk of building up a RE empire for your son and him not taking the offer, concentrate all your efforts in educating him on the world (which I bet you will be extremely good at) and let him fly. If he does need help, you’ll always be there, and that will be the greatest gift you can give him.

  8. I am not confident real estate will be as good in the future as it is today. The reason is self driving cars. With self driving cars, commute is not longer an issue.

    That implies residential location is no longer an issue. How will that affect the premiums of “prime real estate”?

    With more of our shopping being conducted online via ecommerce, there’s less demand for big box retail stores. Amazon is taking a chunk out of Best Buy’s profits. Sears and Blockbuster is shutting down.
    Amazon prime is moving into fashion and clothing delivery now.

    How does that affect commercial real estate values?

    Airbnb has got to be taking profits away from traditional hotels. What are the valuations on hotels ever since airbnb came out?

    These are all major game changers that I see affecting the economy and real estate values. I am not sure exactly what areas of real estate will benefit from these changes. For that reason, I don’t think it’s a good reason for me to put a large chunk of money into real estate. A moderate amount to diversify against other holdings such as stocks, businesses etc… is ok.

    If we take a step back, the changes that tech has brought into our lives over the past 10 years is massive. The iphone came out in 2007. Uber in 2012. If I’m going to make a big financial bet for the long term future, I have to make sure I’m doing it with very good odds. How tech will affect real estate, those odds are not clear to me yet.


  9. In Vancouver’s Marin county aka west Vancouver houses I mean mansions average $12mm and lived often seasonally by family of 4 or 5… And I can’t help but wonder what kind of motivation the kids who live in these single family homes will ever have to build a career for themselves. Cause they’ll never be able to buy the same house the parents bought as an employee. I guess that’s a wonderful breeding ground for entrepreneurs.

    1. What are the big industries driving Vancouver’s job growth and income growth to result in such high property prices? I just don’t get it. What are the big companies out of Vancouver?

  10. Two quick comments: can I request an article on setting up a trust and how to go about that as we have to get around to that and I’m guessing thats something you have done or will be doing shortly (it would be great if you could address kids with disabilities. Also, does that communting chart include one qay or the total miles of a two way commute? Thabks, Sam

  11. Your First Million

    “Now things are lollipops and roses. Rental income is strong. Valuations are at all-time highs. Mortgage rates are still close to all-time lows. Yet rental income has dropped to below 10% of my overall income. At the same time, owning physical real estate has become my main source of stress. Given my life is relatively stress-free, any type of stress is ironically magnified.”

    I can completely understand this. Owning rental property in a city like San Francisco that has such terrible landlord/tenant laws, rent controls, etc… could be very stressful in so many different ways.

    One of the ways to avoid these stressors is to go much bigger! When I was starting out in real estate, I was very stressed all the time. But as my portfolio continued to grow, adding more and more properties and more and more tenants, my stress level virtually disappeared!

    As my portfolio got bigger and I bigger, the more work I delegated to a property management company. At this point all I do with my apartments is recieve a direct deposit of rental income and pay the mortgages. I’m sleeping like a baby ;)

    If you are in real estate and you are stressed, it could be because you haven’t gone BIG enough yet! Think Big!

    1. Very interesting point. Counterintuitive, but makes sense. How many units do you have, where are they located, and when did you start? Your profile on your website is somewhat of an enigma. What do you do? It seems like your RE portfolio is so huge what drove you to start your site?

  12. Grant @ Life Prep Couple

    Being worried is just part of the job as being a new parent. It is incredible how much love you have for them and how would do anything in the world for them. Mine is 8 months old and I have spent a lot of time trying to envision what the world might look like in 22 years.

    It is very difficult to imagine how far technology will be able to take us in that amount of time as it seems to still be growing exponentially. Will college be taught in virtual reality classrooms? Will humans be augmented by robots to the point where a couple people can run an entire Amazon distribution center? Will the average life expectancy be over 150 years? We don’t know the answers to these questions but they do present unique challenges.

    I think you nailed it with:

    “The only thing we can give our children is lots of love and support.”

    And remember you’re the Financial Samurai so of course your kid is going to be a total bad ass.

    1. Definitely self-driving cars and virtual classrooms in 22 years! And average life expectancy should hit 100 for our children, which means all the reason to save and invest.

      Thanks for the encouragement! We shall see. I just want him to be happy and treated with kindness.

  13. Brad - Maximize Your Money

    I love this post, and the comments. We have one child – 21-yo rising senior in college. We’ve told her we’ll help out through the calendar year when she graduates next year and that’s it. I think requiring her to go through some struggle will be good for her.

    I love Kendall’s comments above and would say “+1” for the most part.

    There is an 80%+ chance we’ll die with a few million left so she might get some wealth dumped on her, but that’ll likely be 50 or so years from now and we expect she’ll be established by then. It will be a blessing but not anything needs (we hope and expect).

  14. Many changing trends on the horizon.
    Why don’t the top universities expand to include more students and earn more money?

    I have great difficulty understanding why the world can’t compete and beat california yet. California seems untouchable but it’s only cause of Goog, Fb, Amaz, Uber, Airbnb who each employ between 10000 to 100000 techies. The other 100s and likely 1000s of California pipe-dream companies all have been highly forgettable for the last decade. If you were a leader in India or China I really can’t understand why you wouldn’t have your country produce 100000s new students trained in tech every yr. Then the need for California would drastically fall. Why you would have your country continue to produce instead 100000s of new students training in history, literature, art? Makes zero sense to me.

    1. It’s the network affect. The dirty secret is that folks are no smarter here than many other cities/areas. But we have an installed based of connections and very wealthy individuals which is hard to break.

  15. Surprised there’s an emphasis on top schools. More and more top schools are providing a free education online while a certificate will cost you tuition (Stanford, MIT, Harvard, Georgia Tech). Speed up their learning curve and they can be taking college courses in middle school. Don’t overburden them, but there’s enough guided online courses that they can get general or specialized education. Tons of coding courses, youtube channels with artists, free online books, etc.

    1. I just decided to use these tops schools to demonstrate the point of declining acceptance rates. Given I also work at a top high school in SF, I can see and sense the anxiety of the students and parents.

      But I so DON’T care about spending $70,000 a year to go to a top school since I didn’t go to one, didn’t spend that, and believe in all the free educational resources currently online.

      So my challenge is to encourage and provide guidance. I’m not going to be a Dragon Dad. I swear it.

  16. Sam, providing a child with wealth does not necessarily mean you will raise an entitled brat. With your personality, highly unlikely. Also with you as a parent your child will be the best he can be. Now go make some children before the clock runs out! You’ll soon realize that children are the first real form of true wealth followed by health and lastly assets. You have the perfect trifecta. And you mention rental income is less than 10% of your income? Wow! Your rental income was 100k last I checked.

  17. Ms. Conviviality

    Just thought of another inspiring story: Andrea Bocelli. Maybe your son will take after you with his musical talents. He’ll have to do more than just a few recordings, though.

    1. Great example! Let me read more about his background. My son isn’t blind, just has trouble focusing. Keeping the faith. Speaking of musical talents.. I have very little, but I came up with a Samurai Lullaby I’ll play for you in a future post :)

  18. Adam and Jane


    On point again regarding on providing a job to your children one day.

    From the Millionaire Next Door,
    Economic Outpatient Care (EOC) is a term used to express when an affluent parent provides money to an adult child.

    My brother was financially lost after my parents shutdown the family business. He only worked for my parents and never held a job anywhere else. So after my dad passed away, my brother’s job is to manage the 5 rental apartments in two houses. My mom is basically giving up a bulk of her retirement money to provide income for my brother.

    Depending on parents for money is a big liability and it is a financial crutch. I have many cousins that got cars, houses (800K – 1.5 Million) and money (80K-100K) as an adult. Can these people fend for themselves when their parents are no longer here to help them? I think NOT! One aunt said to me that it is too late to stop helping.

    Let’s hope your children will pave their own road and will provide for themselves. If they know 1/10 of what you know for passive/online income, I have NO doubt that they will be fine!


    1. Howdy Adam,

      I didn’t recall the term, EOC. Thanks for sharing. 5 rental properties and two houses sounds like a good income stream and something that has helped give your brother meaning as well? Surely he can use some of that money to help your mom, who also has you?

      I’d love to hear more from you whether your parent’s property portfolio was a good thing, or not. I can’t really tell so far.

      I will endeavor not to be a crutch. But I know it’s going to be hard b/c all I want is to help….. but I’ve got to let him fall down so he can learn to get back up himself. I was thrown into the fire after college and feel much stronger b/c of it. If I had moved back to Hawaii at age 25.. I don’t think I would have had as strong of a drive, which I really appreciate.


      1. Adam and Jane


        Parents helping their children with a disability is a MUST!! I just pray the BEST outcome for your child and your family. I know you will be a fantastic dad! I just dont agree with parents that overly help their able-bodied children. I have many cousins like this. I am not jealous. We became FI on own. It just pisses me off when some of them dont appreciate what they recieved!

        My parent’s RE portfolio is a GOOD thing. They brought 2 houses in the 70’s for around 65K each and now they are worth over 1 million each. Each house is 3 families. My mom lives in one unit and the other 5 are rented out. We keep the rent WAY below market. One tenant was there for over 40 years and they basically paid the entire mortgage on one house.

        Luckily, I dont have to layout any money to support my mom. Her SS of 10K a year barely covers her meds. I also invested 200K of her money for 5% muni bonds and it generates 10K a year tax free for her to spend shopping for clothes and costco for her supplies. She is addicted to shopping ever since my dad passed away.

        After the water bills, RE tax, gas heating, electricity bills, upkeep, my brother has nothing to give to my mom. My brother has his own rent and 2 childen to support. I asked him to move back to one rental unit and his wife refuses too. EOC!!! Google that millionaire next door term.

        I see that my mom is a crutch to my brother. He does not even try to find a job on his own. My mom told me that she is sorry that she cant give me any money but I tell her that we are OK, we have enough money and we dont need anything from her. She really does not have much money anyway.


  19. Ms. Conviviality

    I’m going to try to fulfill your request for stories of inspiration. I’m not a parent so I don’t have any wise words to share on the matter. Instead, I’d like to share a blog with you that I’ve been following for 4 years now. I read Nella’s birth story and I’ve been hooked ever since ). Nella has Down syndrome but her family treats her just like they do her sister and brother. Of course, she does her therapy sessions but outside of that she’s just a normal kid that takes ballet classes and has play dates. It’s inspiring to see how they really enjoy making the most of life and the opportunities they are opening up for Nella by sharing their story and supporting Down syndrome charities/efforts. I love that her family tries to keep things as normal as possible for Nella, including the hope that she will attend college one day since there are special college programs for people with Down syndrome. Goes to show that anything is possible!

    1. Wonderful! Thank you for sharing. I will read about Nella’s story in its entirety.

      Anything is possible. And I’m so hopeful there will be new inventions and such to help folks with disabilities going forward.

      Just the fact that there will be self-driving cars everywhere w/in 10 years is awesome for folks who have visual impairment and can’t drive safely. That makes me happy, and our kids will only know what they know, so I think things will be fine. I’m so happy to be the father of my son who has the resources and time to help him learn!

  20. At what age would you have that hypothetical discussion over a beer? How young is too young to not let him struggle and claw and develop grit?

    I feel like I personally would be prepared for that talk with my own parents at 35 but better at my current age (40).

    This is something I think about as well with paper assets.

    1. Hi Eric,

      Great question. Regarding my specific escape hatch plan, it would have to be after he graduates from college and after he tries his hand in the working world or in entrepreneurship for at least 2-5 years. So perhaps the beer talk is between the ages of 24-27, b/c I don’t want to let him be discouraged too long if he’s really struggling. That might lead hi down a black hole.

      But he needs to feel at least a couple years of struggle in order to APPRECIATE the escape hatch or when things eventually turn for the better.

      Joy is less joyful without misery. 35 – 40 seems a little old, b/c I have this strong belief that it’s good to be where you want to be, or know where you want to go, or be on the path that will eventually lead to where you want to go by 30. 8 years after college seems to be a long enough time to figure things out.

      But I’m also biased b/c I knew what I wanted to do by age 19-20, and I left the workforce at age 34 and knew what I wanted to do again, after.

  21. I remember my first day of high school track – it was notorious for being insane. The coaches drove all of the new kids into the ground and then kept going. We were all throwing up after the first 30 minutes and had over an hour left after that. Anyone who wanted to quit could just walk away. Probably coaches doing this today would be fired. I was dizzy and trembling and about to pass out – I remember crawling to the locker room at the end of the practice.

    What I didn’t realize, until many years later when he told me, was that my father was parked nearby and watching the whole thing play out. He told me he was in tears and wanted to go kill the coaches.

    That night he asked me how practice was. I told him it was pretty hard but I liked the team. He asked if I was going to continue and I said, “Of course – why wouldn’t I?”

    I remember that story a lot now with kids of my own. We want to protect them so much, but sometimes the adversity they face is not only valuable, it’s accepted and even welcomed by them.

    “It worries me if he has to go through all the things I went through to get ahead.” Remember you wouldn’t be you without those experiences.

    Good luck and God bless!

    1. Man, great story! I think I will be that father b/c I wouldn’t want to be anywhere else and don’t have any office to go too! :)

      I ran track too! And threw up during the first week of practice. “If you aren’t throwing up, you aren’t trying hard enough!” is what my coach told me.

      I did the 200M dash and 200X4. BRUTAL to try and run your fastest for that long.

  22. I think a way for you to be less anxious is to promote alternative lifestyles as your child grows.
    Nothing says he has to go to college, or get a traditional job. The degree, 9-5 job, and white picket fence is the norm in today’s society, but it is not the only option.

    There are independent learning alternatives. For example, Treehouse for coding and Lynda for many other courses such as drafting and management. Your child could even learn a new language on Duolingo. I cannot say how these alternatives will be received in 20 years, but his ability in a chosen field will be certification enough of his expertise. If given the choice between a candidate who has several years of experience and a candidate who just graduated, an employer will always take the experience over the degree.

    Entrepreneurship is always an option too. He could become an independent contractor in his chosen field. Consider EdventureGirl (@ http://www.edventuregirl.com). She didn’t have traditional schooling and she has been quite successful, even before earning her college degree.

    In short, don’t worry too much. 18 years is a long time, and it’s not like he will be alone in this journey.

    1. Hi Sara,

      I think you are right. And who is better to promote an alternative lifestyle than his parents who live an alternative lifestyle right now? I actually have a large post about this in the queue that I’m waiting to publish.

      I am a big proponent of NOT following the status quo.


  23. Sam, this is one of your most genuine articles. Your son will be alright and you will as well – if you have doubt just read your own messages. At the age of 18 months I had multiple eye surgeries to correct stigmatism in both eyes as well as amblyopia (lazy eye) – a nerve disconnect that does not allow me to process stereoscopic vision. To this day and after much eye therapy growing up I still have these vision limitations. They have not been limiting but showed me that each individual sees the world differently. Being able to relate to one another’s world is therefore a powerful skill. My sight disadvantage taught me this throughout life. I started reading your articles before graduating university (not a top tier school) and my first job was nothing to mention – since then I have been promoted or moved upwards 7 times and lived in 5 states and London. Love your son and do not believe there will be any limitation if the eye disorder persists. Recall your abundance article and have hope.

    Long time lurker,

    Sent from mobile.

    1. Hi Ben! Thanks for reading for a long time and sharing your thoughts.

      I love what you wrote, “They have not been limiting but showed me that each individual sees the world differently.” That is beautiful, and I hope others will see others for who they are and accept him for who he is.

      My biggest fear for him is not financial. It is being treated fairly and kindly by others. Kids can be cruel, and adults can be mean and prejudice. I’ve been through too many cruel encounters to think about. I hope he finds a partner who loves him as much as my partner loves me.

      It is wonderful you’ve been promoted so much and have traveled all over for work. I’ve always wanted to work overseas, but never did. Perhaps you’d be open to sharing your story in a guest post one day. It would truly be an honor for me, and for other readers also on a similar journey.

      Thank you!


  24. Scott Thomas

    Great post, Sam. I’m in a similar situation …. 50 years old, nearing retirement, I also live in California, and thinking about the best possible situation to leave my children to help navigate their future (which I agree will be more difficult than ours was). But I differ with your conclusion.

    Rather than choosing the route which you feel is more stressful (real estate), why not focus on what you enjoy and what is most profitable for you (online business), then you can leave your child/children with a solid inheritance that they can use however they need? Thinking about our children’s future is important, but it’s impossible to predict what situations they’ll be facing in 20-30 years. (Just think about how much tech, online businesses, SF, Silicone Valley, etc has changed in the past 5 years, and try to predict where things will be in 30 years!). So rather than leaving them a real estate empire, why not just leave them with a big pile of cash?

    I love your point about leaving them a place to live in an expensive city, but leaving them a nice home in SF won’t help them if they get a job in Shanghai. The cash flow from your real estate empire would help them to buy a home wherever they want, but so will a big pile of cash from your online business. It sounds like it’s less stressful for you to generate your big pile of cash via your online business rather than real estate, so why not do that?

    Love to hear your and your readers’ thoughts … I’m facing similar decisions now and I can use all the help I can get!

    1. You’re right. I originally entitled this post, “The IRRATIONAL Reason Why I Wanted To Build A Real Estate Empire,” then I decided to simplify it b/c I couldn’t come to a definite conclusion on what I wanted to do. But I’ve laid out some hints in this post for a future post I plan to publish on what I’ve done with my single family rental.

      I can’t leave a big pile of cash. It just feels too wrong. I want to pay for education, and perhaps provide subsidized housing (he needs to live on his own) if absolutely necessary. But cash is a motivation killer. I’ve seen in way too many times.

      Robbing a child of their drive, potential, and independence is one of the worst things a parent can IMO. But maybe my thoughts will change!

      What I want to give him is a tremendous education from me as well. I can teach him about: real estate investing, stock market investing, bond market investing, climbing the corporate ladder, networking, online media, marketing, writing, speaking, tennis, and lots of other stuff. I’m not going to just rely on the school to teach him stuff. I’d like to teach him stuff that I’ve spent 20-40 years learning b/c I have the TIME to do so for the next 20 years.

      I’m pumped!

      1. Hi Sam,
        I found your site through my husband who raves about you and after reading just this one random post that caught my eye I can see why.

        First off – your honesty is incredibly refreshing!

        Secondly – as a mother of a teen I worry like crazy some days, but mostly beam with pride to see he has learned many of the beliefs we hoped to instill.

        Things like; you are the sum of your 5 closest friends – or that your actions are much louder than your voice – and that your honesty, integrity and your word are values that can only help you.

        In my experience; the biggest thing I have seen parents do to harm their kids is to not talk to them.( It has to be at THEIR level or it doesn’t work as well).

        We talk many times a week about what’s going on (including what hubby & I are up to).
        For example; our son recently started skyping again with a former school mate who moved away. She was cursing like crazy and referencing many inappropriate topics in a back-handed way he didn’t quite understand.
        We had a long discussion on where this behavior might be coming from and why I was upset by it (her mom is a friend of mine). It helped clear the air and since then our son has asked questions and brought up several other good questions regarding the situation which allowed him to find a way to cope that works for him.

        My point is this. Being a parent NEVER turns off.
        Yet I have seen many parents allow others or the media to teach their kids “what the world is” at certain stages in their development by not talking with them about all they are exposed to. Digitally, audibly etc. almost like they get lax at certain points (sit a kid in front of a brand new movie but not watch it with them) the kid may have no point of reference and think something awful is normal behavior for instance.

        There is plenty of craziness out there, which we all know.

        Always making the time discuss what is current in your kiddos world provides so many subtle benefits.

        Given your thinking way ahead of the game with your strategy, leads me to believe you all will be more than fine – after all it’s the prepared who find their way!

        All the best and I will be reading lots more when it’s not so blasted late.

  25. Keeping rentals you don’t like on the off chance that your son will both need and want to live in one of them one day seems unusually irrational for you. If you’re willing to subsidize his future lifestyle, you can just give him $5k a month or whatever with which he can live anywhere he chooses! Giving/having liquid investments will give you a lot more flexibility to maximize his use for and enjoyment of your bequest.

    Maximizing your net worth and income streams while minimizing your stress should be your goal. Less stress means more energy (and time) to put into mentoring and loving your little boy.

    1. You’re right. It’s irrational, although there are long-term financial reasons as well e.g. I believe real estate prices will be much higher in SF 23 years from now.

      The funny thing is, I never thought about just handing him $5,000/month (equivalent to the net cash flow of this property) if the time comes. That is a lot more flexible. I think I don’t about this option b/c there’s no WORK and responsibility tied to the $5,000/month. When that happens, I may extinguish his drive and pride.

      So if I go the flexible route, I should figure out something for him to do. And that is a potential new post: working for my online media company. BINGO.

      But wouldn’t it be great to pay hime $5,000/month to work for my company, and use a part of that income to pay rent in a property I own? :) Ahh… the mind is always churning.

      1. Sam,

        May I suggest getting him on the payroll immediately. If he, ” you” fund his Ira for the next 18 years by putting $5500. In per year into an index fund averaging 10 percent “historical average”it will be worth 223k when he’s 18. Not putting a penny extra for the rest of his life it will be worth close to 20 million at age 65.

        The only kicker is that you need to show them making 5500 per year if you want to contribute that amount.

        Thanks, Bill

      2. Haha I get what you are saying. It probably *feels* worse to hand over large chunks of change to your kid to employ (enabling!) rather than simply allowing him to live rent free somewhere while he figures life out (appropriately supportive!). But the effect is the same, and your kid – and your kids’ friends – will recognize it. In fact the effect could be worse because your child won’t be invisibly deploying funds but will be living in a relatively lavish abode which will give him all sorts of status despite possibly earning very little, being very young, and/or not having earned any of it.

        If you’re talking about giving him a RE empire to manage rather than a place to live, I can appreciate that and it makes more sense. But it still doesn’t mean you have to keep THESE properties for the 2+ decades in the meantime if you don’t want to. You can always buy an apartment complex 25 years from now and let him manage it at that point if you need to. And that will give you location flexibility as well. Besides, your child may be shy and creative and tenderhearted – in other words he may possess roughly zero of the traits necessary to be employed as an effective property manager. You might have to endow a museum for him to curate instead. :)

  26. Hi Sam,

    The worrying and anxiety relating to your kid NEVER goes away. However, as time goes by you do learn to handle it a little better.

    My 17 year old daughter is doing a 400 mile road trip today on the interstate and over a mountain pass. My wife and I are both terrified. She told me. “Dad, sometimes you got to push the bird out of the nest if you want to see it fly” I love that kid!


    1. Gotcha Bill! And good luck to your daughter on her road trip. Glad you have your wife to hug during fearful times :)

      I think I would breakdown and buy her a tank before allowing her to go.

  27. Love the emergency plan and forward thinking, but odds are your son turns out far better than you alluded to in this writing. (I’m making that assumption based on your work ethic and the likelihood he’ll learn some of that from you.)

    Then you’ll have less to worry about and he might build his own empire without your help. Wouldn’t that be nice?

    Questions: Do you plan on passing FS to him when you’re older? If not, what’s your plan for this site?

    1. After July 1, 2019, the lights go out on FS. That’ll be my 10 year mark, and then it’s on to the next chapter.

      But if I see some creativity in my son, maybe things will change!

  28. Mr. Freaky Frugal

    Sam – As a parent of 2 adult children, this is difficult shit. I don’t have a son with a disability, but one of my sons is gay and there are still plenty of people that have a bias against that. It has not slowed him down so far.

    After I became an adult, I asked my Dad if he worried about us (his offspring) and he said that “you always worry at least a little.” I can confirm the same thing as well. The best advice I can give on that is get used to it. It’s not going away. Ever.

    Most parents – me included – would like to protect there children from the hardships of life. But it really doesn’t work very well because the hardships of life shape you into who you are. From your blog, I think they have shaped you. Would you agree?

    The best thing you can teach your son is resilience. And that only comes from watching fall down and then helping him to get back up. Eventually he won’t need any help and he will just get back up on his own.

    1. Thanks for sharing. I’m so happy your gay son is born relatively recently, rather than 40+ years ago. We’ve come a long way in terms of accepting everyone, but we’ve still got a long way to go. One of the reasons why I love bigger cities like SF or NYC is because there’s so much diversity and acceptance. I love, love Amsterdam too.

      You are right about my experiences and any hardship I had shaping who I am today. We need our children to go through hardship to make them grittier, more appreciative, and happier people in the end.

      How old are your sons?

  29. The best thing my parents did for me was teach me how to work hard (for example, my sport required me to wake up every morning at 4 am) and they told me from a young age that I would have a “free ride” to a college of my choice. So that’s what I’m doing for my son. I wouldn’t want him to grow up feeling entitled, but I do want him to know that I’ll support his education. If he had a disability, I think I’d have a different approach and think about some kind of trust (or real estate empire) to support him.

    1. Was that sport crew? 4am sounds brutal!

      I plan to show him consistently strong work ethic by waking up by 6am every morning, teaching him about things and answering questions before he goes to school, being there when he’s home to play and teach, and do some more work from home.

      Interestingly enough, as a work from home parent, I can demonstrate more work ethic than a parent who works 14 hours in the office. Just thought of this positive thought! YES!

      1. I was in a similar situation to BH. My parents helped me with the things I needed, not the things I wanted. They covered sports participation fees and helped with college costs not covered by scholarships the best they could. Everything else, like iPods, cell phones, college books, entertainment, etc., were things I could save my money and purchase myself. It helped me realize how much things cost, and then I decided if these items were actually worth spending money on.

        Sports taught me a lot about working hard. In college, I swam, so I was usually up at 5AM most mornings to weight lift or practice and then back to the pool later in the day for a double session. Nothing teaches you about hard work and humility like training and competing for a mile swim. If you make your goal time, you are on top of the world. If you miss it (sometimes by hundredths of a second), you wonder why you even bothered to train so hard. There are no shortcuts. You just have to go back to the grind and hope that your hard work pays off in the end.

        Congrats on the new addition. With a dad like you, I’m sure he will turn out just fine.

  30. Vancouver Brit

    I agree with Sam above, have a little faith in your kid and definitely don’t give him everything on a plate. You’re sounding a little paranoid and protective in this post. Giving your children everything they could want in life for no effort is a sure fire way to raise an entitled, spoiled adult who is incapable of looking after themselves in the real world. What does it teach your child if he knows he has your wealth/real estate to fall back on?

    You should be very careful how you portray your wealth and ability to look after your son to him. I wouldn’t go letting him know he has a real estate empire to fall back on or a place to live for free in San Francisco is he fails. All this does is discourage him from even trying, providing him with zero drive or work ethic. You might end up creating self fulfilling prophecy where you actually cause your son to fail by giving him everything because you’re scared of him failing.

    I’ve seen first hand the damage that can be caused by a person being given everything in life by their parents, it’s a real threat. I assume you have heard of the three generations of wealth? If not, look it up, you want to avoid this at all costs.

    I guess long story short is, it’s great you want to support your child and I don’t disagree with this (every parent would do the same). However, he shouldn’t know you will always be there to fall back on. In fact, you should try and make him think that you won’t be there to fall back on when really you will be. You said it the other day, FEAR is one of the keys to success. He needs to fear not succeeding in life in order to succeed. You giving him everything he wants removes this fear entirely.

    1. Thanks. Check out the last couple paragraphs in the post.

      Also, are you a parent? If so, how do you manage your worries and what type of insurance plans have you created? Thanks

      1. Vancouver Brit

        Ah sorry! Yes, I did not read the last paragraph. I think that’s a wise move.

        I’m not a parent no, not sure if I will go down that road yet but we shall see. I was raised in a pretty working class family and for sure had nothing to fall back on if I didn’t make a success of myself. The most security I had was I always knew I had a bedroom in my parent’s home to return to if I did run out of money. I guess your insurance policy is an upgraded version of this, rather than it being your family home, it’s another home you own that he can use.

        Personally I don’t know if I would build an insurance plan for my child, but then again all that might change if/when I have one. As long as your child always has a safe home to return to when times get tough, to me that is enough insurance. This also provides some drive for him to succeed on his own as he (likely) won’t want to end up living with his parents his entire life. I find this is THE key driver for motivating young adults to succeed, to move out of their family home. In that regard, you might be better off simply ensuring you have a spare bedroom at home for your child if he needs it, rather than a spare, separate house.

        Heck, many parents go one step further and actually charge their children money for rent and food etc. if they REALLY aren’t motivated to succeed and move out on their own.

  31. I hope the potential eye issue turns out okay. It’s really hard when your kid is sick or could have long term health problem. As parents, we just have to do the best we can and live with it.
    I think it’s good to let the kids struggle too. They need to figure things out for themselves. If the safety net is too big, then they won’t push as hard.
    Good luck!

  32. “If a top 25 college has a 10% chance to get in that means if you apply to all 25, you have >95% chance of getting into a top 25 college.” — To be exact, if the probability is independent to each other, then the change of getting into at least 1 is 1-(0.9)^25 ~92.8%. However I highly suspect the assumption that the probability is independent in this case, which will render the above conclusion irrelevant.

    Not to be a downer, I don’t see leading a mediocre (by usual definition) life is bad, that means he leads a life quantitatively measured to be better than 50% other people and not as good as the other 50%. That’s a NORMAL life and why is that frowned upon anyway? Life is about the journey, not the destiny.

    1. Nothing wrong with a normal life. I think worst case, he’ll have an OK life, which is a nice worst case. But b/c he will be hanging around other kids with highly successful parents who may drive their kids to high achievements, he might feel like a failure, since everything is relative.

      Hence, the key for us is to figure out some way to keep things real, keep friends diversified, and manage expectations for him. I’ve already managed my own expectations for him per this article. I just want him to be happy.

  33. Sam,

    You will have told him about the escape hatch plan well ahead of time. He will be googling it! My boys today know so much more than I did at their respective ages (nine and six), given their ability to research on google, YouTube, etc. I would pick an over-under of ten by the time he has read all of your blog articles, including this one!

    Hopefully there is no issue with vision / learning that holds your little guy back. Catching it young, as it sounds like you have, can be super beneficial and the optometrists can do some amazing work at a young age to help correct any issues. Both my son and niece did the pirate patch (likely not the technical term) and had significant improvement in the eyes with issues. Not sure what you are going through and wishing you, your wife and son the best in resolving it.

    That all said, we have the exact same plan of having two rental units so that when our boys are college age, and older, they will have starter apartments. Like San Francisco, Vancouver is getting so much more expensive by the day and they won’t be able to afford a home otherwise.

    Will be writing in my Q2 update that we are likely assigning one of the two apartments though. Given the insane lift over the last twelve to eighteen months, I am too worried that we are approaching bubble territory and don’t want to leave money on the table. I will try to frame my thinking, pros and cons, how you do when making these decisions.

    1. Ha! You might be right about that. Gotta work on my stealth game a little more then.

      Do you mind elaborating on the pirate patch, what it does, when you discovered the eye issues, and how the progress has been? All I really want are several eye exercises I can do for my son so that I can strengthen his eye muscles and improve his chance at a healthier vision. Many doctors and parents say that glasses and contacts (both of which we have) help stabilize the eye. And some have reported their kids growing out of the issue. It’s one of those things were if there’s anything I can do to help improve his chances, I will!

      Good luck w/ your Vancouver property decision. It feels like Vancouver is more frothy than SF given the lack of a large industry that pays well. I’d love to check out your Q2 report.

  34. “It worries me if he has to go through all the things I went through to get ahead. I don’t think I could do it again if I had to start over. Further, so much of my accomplishments were directly attributable to luck. Good thing our children are more resilient than we think.”

    You saved yourself with that last bit about resiliency. Reflect on how all of the things you went through have made you who you are and remember it is not your job to ensure every bad thing that ever happened to you does not happen to your child. It should be your job to coach them through bad times early on while also providing them the tools to gradually be able to handle bad times on their own. Monitor and test their self-sufficiency frequently, then coach as needed. You will be continually amazed at the person he becomes and he will thank you profusely down the road. The best things my mother and father ever did for me were:
    1. Not doing everything for me
    2. Being great examples and role models by hustling their fingers to the bone
    3. Not letting their divorce when I was 7 impact their ability to parent as a team
    4. Not being my “best friend” all the time and enforcing rules, even when it caused friction

    I look back at those things and have an other-worldly respect for both of them. Our relationships weren’t always fantastic but they were always on a solid foundation of respect and love, yet have grown beautifully as I have grown up. They also appreciate my 100% financial independence from them since graduating college on-time five years ago. My mom tells me some of her proudest moments are when she hears from parents of other kids I grew up with that their kid either moved back in with them at 28, doesn’t have a plan in life, has three kids with no job or is hooked on drugs. Of course, she feels for the parents but she’s proud because she knows she has never had to worry about those things with me due to the choices she made in how she raised me, prepared me and gave me the tools to make good choices of my own.

    It’s okay to hold your child to high expectations. Combine them with love, patience, teaching and accountability. It’s okay to let your child fail. Coach them on learning, persistence, controlling emotion and understanding that some mistakes are okay while others are not, nor is failing to learn from mistakes. Finally, it’s okay to be afraid for your child. Use that fear to protect them from the real dangers in life instead of the minor bumps and bruises that make them stronger.

    You’re going to do great. I can feel it. Although, I’m 27 and have no kids of my own yet so I could be talking out of my ass lol keep up the great work! FS community believes in you!

    1. Thanks for sharing your thoughts Kendall! It’s great you have a good relationship w/ your parents who’ve been so encouraging along the way.

      What I realize, but don’t fully realize is that of course it’s going to be more tiring if I had to do it again, b/c that means I’d have to do it again TWICE.

      “Not being my “best friend” all the time and enforcing rules, even when it caused friction” – This is an interesting point which I’ve read several times already. Is it tough to enforce the rules while also being a great friend? I think that’s every parent’s dream maybe… but it probably gets messed up when less discipline happens.

      1. Sam, yes, it is, but I think it can be done.

        Remember this ONE thing, and you’ll be good:

        You son has to know that you LOVE him, NO MATTER WHAT. He can’t do anything to lose your love.

        It doesn’t mean that you agree with every choice or choices don’t have repercussions. Far from it. But you love him, and you will ALWAYS be there for him.

        I told my son that over and over and over again. Then when I was telling him something I didnt’ agree with, I would ASK him “Am I saying this because I love you or am I trying to hurt you”. He ALWAYS answered the first part, whether he agreed or not. He KNEW I loved him, no matter what.

        Without getting on a tangent, having a son completely changed my views of God. I became LESS religious and realized that God loves us no matter what (and I no longer believe most of the religious teaching I was raised with).

  35. I can only address your statements from the point of view of someone who has struggled to get to where I am, and how my parents helped me to become a responsible and driven adult by not helping me (too much). I have finally cracked the 25% income threshold at the ripe age of 29. I quit college twice and finally got my degree 7 years after graduating high school. I’ve made bad life choices as well as financial mistakes, but kept at it, graduated, and became a CPA. I never had the promise of a safety net from my parents, but instead their assurance that they would be proud of me as long as I tried my hardest. I never once felt like I’d let them down, and this gave me the confidence to believe I could push forward. Parents, let your kids struggle and figure out the world on your own, supporting them along the way. The bulldozer parents are only leading their kids to be dependent.

    1. It is a testament to your parents that they never once let you feel like you let them down! I endeavor to be that type of parent. And I hope I can handle myself if he doesn’t end up trying his best.

      Congrats on getting your degree and breaking the top 25%! Grit!

  36. Probably an unpopular opinion but it sounds like you are already counting your son out, or at least it feels there is a good chance you believe he will live a life of mediocrity. Maybe it is your lack of faith in your parenting ability that is making you think of these scenarios.

    Why not flip the narrative on the schooling? If a top 25 college has a 10% chance to get in that means if you apply to all 25, you have >95% chance of getting into a top 25 college.

    Might get bummed with rejection? Hope you don’t raise a kid that weak.

    Maybe the reason why wealth doesn’t stay in generations is because the well of father doesn’t have confidence in his kid from the get go?

    1. Indeed. I have little confidence b/c I’m a new father. My confidence should rise as I gain more experience.

      I always set my expectations low. “Underpromising, overdelivering” has been indoctrinated in me since I first started working after college.

      I don’t want to expect him to always get a 100% on his test score and go to Harvard or else. What a miserable and stressful life he would lead.

      How about you? Do you have children? How do you manage expectations and such?

      1. It’s tough to manage expectations. Our kid is good at book learning, but he’s pretty bad at socializing. He has some behavioral issues and that’s a hard thing to accept. Yes, we are being strict with him, but it doesn’t work all that well. If we ever bring him in to get tested, I’m sure he’d be classified as “special.” Screw that. We’ll just do our best and keep going. You never know what you’re going to get with a kid. Every kid is different.

        That math about college application sounds wrong too. It can’t be that straight forward. If your chance is 10%, then it won’t improve to >95% just by applying to more colleges. Maybe 20%…

        1. We have one son who is a little older than two. I myself don’t want him to experience all the thoughts and emotions that I went through when I was younger.

          I have to be honest to say that I want him to be the best student in his class, go to the best school, and get the best job out the there. But the world is not so simple. I almost said good bye to the world wanting and trying to be the best.

          Based on my experience, I will be happy with whatever my son does as long as he’s doing his best and not involved in anything illegal.

          I’d be more than happy to give our son everything I have under the condition that he’s independent and hardworking.

          Thank you for sharing your story, Sam. I tend to worry a lot too, but I realized no amount of worries can put things in order on the way we want. Everything will be ok. :)

        2. That weird math assumes the application process is random, which is a ridiculous assumption. The same 90% of applicants being rejected at each university is closer to reality.

        3. Yes, screw that Joe! Every kid is different in terms of temperament, learning speed, predispositions, etc. I am not going to be one to have him conform to the way society wants him to be. The rigid structure isn’t something I truly believe in b/c there are so many ways to have a great life and make a great living, as you and I know!

          Good catch on the math :)

        4. >>He has some behavioral issues and that’s a hard thing to accept.

          I could relate to the way you described your son. The hardest lesson I had to learn being a father is “my son is NOT me”. There are a lot of bad things he did and tried that I never did. He was also super book-smart, which I never was. His make up is different than mine. He craves structure. I hate structure.

          Joe, I like your plan, the way you think. “All kids are different” and you’re going to do the best you can. I believe that is ultimately the best plan.

          It’s easy for me to look at the way I grew up and say “my son would have never made it”. But I’m starting to think if the circumstances were reversed (he grew up when I did), MAYBE he would BE different. I know MY father would have killed him if he weren’t. Haha.

  37. Save Splurge Deny Debt - Cameron

    Love the parental tone in this article. I think it is awesome to keep that thought of providing for our children top of mind. My family is the reason for all of my financial independence dreams.

    You are well ahead of the curve at providing something for your son that can leave a lasting legacy on your family for generations. They can always talk about their crazy great grandfather who bought homes all over when ‘experts’ thought housing was expensive and a bad investment.

    I guess I want my child to be motivated and hard working with the ability to do whatever he wants, but never tell him about having enough money to do nothing. The Warren Buffett money transfer system.

    Thanks for sharing this!

    1. I hear yah. I’m proud of my grandfather (RIP) for buying some property in Honolulu back in the mid 1900s. He said he was almost going to buy a nice lot on the Waikiki water front in the 60s or so, but didn’t b/c there was a butcher shop next door. Doh!

      If my grand father was a RE tycoon with water front property I wouldn’t feel spoiled or want to do nothing. I think I’d be totally inspired to learn from him and try to make my own fortune! SEEING our parents and grandparents hustle has inspired me the most. And any success they have is an encouraging datapoint that potentially I could do something similar too.

      So maybe drive is a part of our DNA. We can think: our parents our poor, I must do well to provide for them… or, my parents are rich, I must do well to show them I can stand on my too feet. That’s a positive, positive way to look at things which I think many of us do.

  38. Hugs! As parents worrying about our children is second nature – I can’t imagine how much harder it must be if on top of the regular worry, you also have to worry about a potential vision disability.

    Whatever happens though, your son is in your most capable hands, and he is going to be just fine.

    1. Thanks! Hugs back. I think about him every waking minute now. Just hoping for the best, and if the best doesn’t happen, that’s OK because everything is surmountable with enough love and support. Any disability he does have makes me want to care for him that much more. Maybe it’s evolution to help make dad’s want to love their sons more, just like how cuteness makes parents want to take care of their children more.

    1. Sam, you’re working to relieve your own stress and take care of your family. Who could possibly argue with that? Good on you.

      Passing down the family business is a great opportunity — if your son (or more children?) is/are interested in taking the reins and reign over Samurai-land, they will truly be blessed. Of course, they might want to go in a different direction (and I know you won’t be disappointed if they want to build a company or other effort on their own, just like you did).

      Still, while fear is a great motivator (you had a great post on that), there will be new opportunities you and I can hardly dream about right now. Your children, and my nieces and nephews will enter a world that — yes — might be scary to us nearly old-timers, but could be dazzlingly beautiful and full of new growth.

      With you and your wife as guides, I think your children will be more than alright; they will be loved, wise, and giving back to the world in ways you will be proud of forever.

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