How The Rich Get Richer: Strategies For Competing In A Rigged Game

How the rich get richer: helping you compete in a rigged game

Let's look at how the rich get richer. After all, half the battle is staying rich for multiple generations.

Making money is like playing a competitive sport. You train hard all your life for those moments on the battlefield where you win all the spoils or go home empty-handed. You console yourself after a loss for having tried your best, but eventually, you realize the game is rigged.

For the past 12 years, I've played USTA league tennis. It's a great way to stay in shape, meet new folks, and keep the competitive juices firing. Everyone needs to balance mental activity with physical activity if they want to stay healthy.

For the past six years, minus one year off due to the birth of my son and one year off due to the pandemic, I've played at the 5.0 level. It's a treacherous level filled with ex-college players and even ex-pros. Few have a beer gut and everyone has at least one weapon, be it a cannon serve or a heavy topspin forehand.

Battling Against The Odds

Let me use league tennis as an analogy of how the rich get richer. I really enjoyed playing 5.0 level tennis my first year (2015). It felt like I had joined a new fraternity of men I never played with or against before.

I joined a team of newly promoted 5.0s and high-level 4.5s and we relished just playing against high-level players, not concerning ourselves with victory.

USTA Rating Distribution - 5.0 tennis
USTA Rating Distribution. 1% are rated 5.0

During the second year, I no longer had as much fun because the experience wasn't new anymore. In fact, the experience started getting old because I kept losing. It didn't feel fair to match up with a 4.5 partner or a borderline 5.0 player like myself and battle against two veteran high level 5.0 opponents over and over again.

After following a 2-3 season with a dismal 1-7 season I thought surely the USTA would bump me down to 4.5, but it did not. The USTA said that because I lost some very close matches with a 4.5 partner against two veteran 5.0 players, those losses actually helped boost my rating.

During the 2018 season at 5.0, I realized there was no hope of ever getting ahead playing on a public park team unless I made some drastic changes. I was getting older, slower, and sustaining more injury.

How the rich get richer in competitive league tennis

  1. If you are an elite player, you will be recruited by a private club. They will give you a discounted rate, sometimes wave the initiation fee, and certainly fast track your membership. The public teams from public parks will have no chance of ever recruiting you because they have nothing special to offer.
  2. Once the private club has some elite players, it becomes easier to recruit even more elite players to its team because similar-level players want to play with other similar-level players and create a social network. Meanwhile, public park players either don't have the money or the connections to join a private club and are stuck playing with whoever joins that year.
  3. Private club players develop a familiarity with each other's games because they tend to be long-term members. Having a strong chemistry is huge in doubles. Public park players are always rotating doubles partners because the team is open for anyone to join.

This is how the rich stay rich and keep on getting richer. They have all the competitive advantages already. Then they get even more help by playing with even better connected, wealthier, and more powerful friends.

When you already have a $10+ million net worth and hang out with other $10+ million net worth people, you're inevitably going to get even richer.

Kept On Battling Against The Odds

In 2019, I was excited to play doubles against an opponent I had lost to 5-7, 6-7 in a two-hour match a couple of years earlier. He had played for UVA, a national collegiate powerhouse. His partner was an ex-Harvard player.

But this year, I partnered with a 54-year-old guy whom I never played with before. Like me, he didn't play D1 college tennis. And my UVA opponent partnered with not a 5.0 rated player, but a 5.5 rated player who was once ranked 500 in the world!

Talk about a stacked game. We lost 3-6, 1-6.

From these three points, you can see how there is almost no way the middle class, let alone the poor can fairly compete on an even playing field. What is required to get ahead is a tremendous amount of luck and hard work. No surprise.

But besides luck and hard work, let's look at some other strategies to help you compete against the rich in a rigged system.

How To Compete In A Rigged Game

Now that you know how the rich get richer, let me share some tips on how to compete in a rigged game.

1) Sandbag your abilities.

Sandbagging in recreational sports is commonplace. People purposefully throw games so they don't get bumped up. By playing at a level below your real ability, you can win more. It's great to see how far your abilities can take you, but after reaching your peak potential, you may want to swallow your pride and move back down.

One of the keys to getting ahead at work is to consistently over-deliver on expectations. The way to consistently over-deliver is to realistically under-promise what you can deliver. You must act a little dumb to get ahead. This way, you'll always be able to surprise on the upside.

The same phenomenon happens when a publicly traded company reports quarterly earnings. After 20 consecutive quarters of beating analyst estimates, analysts are either complete dumb asses, the company is just truly amazing, or the company has mastered the art of sandbagging. 

Sandbagging is important because stocks get crushed, especially growth stocks, when they miss analyst estimate. Conversely, stocks tend to outperform when they beat.

2) Directly ask for help.

One of the most insightful commentaries that have come out of an Asian Coalition suing Harvard for racial discrimination is what an Ivy league university admissions officer revealed. She said, and I paraphrase, “Out of all my years working at XYZ university, not once did I get an e-mail or a phone call from a special connection advocating for a potential Asian applicant. Whereas I was always fielding favors for other applicant races.

In other words, stop believing that meritocracy alone gets you to the promised land! Swallow your pride and be bold enough to ask someone important who you've worked with for help and a favor. Self-advocate. Sell to others why you are worth fighting for. Don't be so modest. If you don't call in the favors, you are at a huge disadvantage to anybody who does.

Find a balance between offense (active self-promotion) and defense (letting your merit speak for itself). 

Take Financial Samurai for example. Oftentimes I believe my content is good enough to get recognized by larger outlets, so I don't bother promoting my work. Yet, I'm frequently passed over because the white journalists that dominate the personal finance media tend to only reach out to fellow white bloggers. People just tend to help people who look more similar to themselves.

Instead, I need to pitch my work because I'm one of the few who actually has a financial background writing about personal finance. Yet, so much about online growth is marketing.

Related: Three White Tenants, One Asian Landlord

3) Befriend the unicorns.

While applying to a pre-school for my son, I learned that there were spots for only four non-sibling kids out of 300+ applicants. In other words, my boy has less than a 1% chance of getting in. We have zero expectations. But, we can improve our chances by going to fundraising events, befriending board members, trustees and so forth.

The rich aren't evil people. Just like everybody else, they want what's best for themselves and their children. Make an effort to get to know them by asking for introductions, be proactive about meeting up, and say yes to social events, especially ones that are for good causes. No matter what your socioeconomic background, someone is connected somehow to someone who might be able to help.

Seldom do people ask for help outside their circles. Make it a point to try and help that someone first before asking for anything. I found the best way to befriend rich and powerful people is by sharing a common interest. In my case, that interest is tennis.

Unfortunately for my son and for us, we got rejected/waitlisted from 6 out of the 7 preschools we applied to. Just as well as we wouldn't have sent him during the 2020/2021 school year anyway due to the pandemic.

4) Blaze your own trail.

Sometimes the game is so stacked against you that you have no choice but to take all the risk by doing your own thing. I knew that my chances of getting promoted to Managing Director were slim working out of a satellite office. Hence, I decided to leave work and go straight to the top as the CEO of my own company. Succeed or fail, it would be all my doing.

If you are from humble beginnings, one of the greatest gifts you have is that you don't have much to lose. Why do you think there are so many immigrant success stories in America?

If you already come from a wealthy family, there's too much downside to doing anything other than becoming a doctor, financier, lawyer, techie, or consultant working for someone else. Then again, once your family is super rich, you can really shoot for the moon.

On a professional level, there's nothing that gives me greater happiness that growing Financial Samurai from nothing. To be able to generate enough online income to comfortably take care of my family of four in expensive San Francisco makes me proud!

Now I've got a book deal from Penguin Random House to publish a book in 2022. As someone who subscribers to the Legacy Retirement Philosophy, I'm thrilled to be able to make my family proud.

5) Marry into wealth.

You can either work hard for your money, or you can marry into wealth. I used to think this was an utterly BS strategy, but now that I'm older, I see the merits of finding companionship with someone who can provide all the comforts in the world. It can get very tiring being a sole income provider.

If you can't afford to attend a rich private school for undergrad or your MBA, then the next best thing is to hang around in the same circles as the wealthy. Finding love is a numbers game. The more you can put yourself in a situation to meet a wealthy person, the higher your chance of finding a wealthy lifelong partner.

We know that wealthier people buy groceries at Wholefoods instead of at Safeway. Wealthier people tend to shop at Nieman Marcus than at JC Penny's. They go to the opera, the ballet, and to galas.

They tend to play golf. Here in San Francisco, you might want to just hang around at one of the many Facebook, Google, and Apple shuttle stops to start up a random conversation about how to generate more fake news revenue.

It feels amazing building your own wealth. But all the people I know who married into wealth don't seem to mind flying private one bit.

Recognize All That's Unfair In This World And Proceed

Do I wish I was 6'6″ with a 145 mph serve? Only when I'm playing tennis. Otherwise, sitting in a car or on a long flight would be a PITA. I'm happy with my 5'10” frame, but recognize in order to compete effectively, I've got to train harder and eat better than someone with more physical advantages.

As the world gets richer, you will encounter more scenarios where your peers have had everything given to them. It's not their fault. Parents can't help but want the world for their kids. You can either get extremely jealous about their good fortune, or you can learn to accept reality, befriend them, and see if you can create some magic together.

Work on your merits, but don't be embarrassed to ask for help from those who can.

Related: The Top 1% Net Worth Levels By Age Group

Stay On Top Of Your Wealth Like The Rich

Sign up for Personal Capital, the web’s #1 free wealth management tool to get a better handle on your finances. Run your investments through their award-winning Investment Checkup tool to see exactly how much you are paying in fees.

After you link all your accounts, use their Retirement Planning calculator that pulls your real data to give you as pure an estimation of your financial future as possible using Monte Carlo simulation algorithms. What you measure can be optimized.

Invest In Real Estate Like The Rich

The rich diversify their investments into real estate. Real estate is a tangible asset that is less volatile, provides utility, and generates income. Stocks are fine, but stock yields are low and stocks are much more volatile. The -32% decline in March 2020 was the latest example. However, real estate held steady and appreciated in value then. 

The rich have real estate empires for cash flow and capital appreciation. Further, the rich buy real assets to leave to their children to manage and earn. Every single rich person I know has an enormous real estate portfolio for a reason. Real estate is a proven way to build real wealth.

Take a look at my two favorite real estate crowdfunding platforms. Both are free to sign up and explore.

Fundrise: A way for accredited and non-accredited investors to diversify into real estate through private eFunds. Fundrise has been around since 2012 and has consistently generated steady returns, no matter what the stock market is doing.

CrowdStreet: A way for accredited investors to invest in individual real estate opportunities mostly in 18-hour cities. 18-hour cities are secondary cities with lower valuations, higher rental yields, and potentially higher growth due to job growth and demographic trends.

I've personally invested $810,000 in real estate crowdfunding across 18 projects to take advantage of lower valuations in the heartland of America. My real estate investments account for roughly 50% of my current passive income of ~$300,000. 

53 thoughts on “How The Rich Get Richer: Strategies For Competing In A Rigged Game”

  1. If you have no real qualities, like to be part of a group and money and status is important to you, this is probably a good article. Otherwise, it reads like selling your soul and giving up your honour to be with people you probably do not really like and spending money on things that do not really give you happiness. I am of the opinion that time is still the most valuable asset on earth. Do not waste it on things that are not worth it.

  2. Great read, Sam. I enjoyed reading about your tennis experience and how the good players are all skimmed by the competitive clubs.

    That dynamic is rather common across many areas of life. The good are resorted into a higher class where they compete against and socialize with ever-increasing levels of competition to build their skills and relationships. This increased competition only elevates their game/studies/skills to a higher level and meanwhile, the middling-to-poor performers remain behind to fend for themselves.

    Take schooling for instance. The brightest students tend to leave their public schools or less-competitive private schools for spots in academically-recognized charters or more-prestigious private schools. They then go on to the most hallowed universities by improving their skills, or, as you suggest, knowing the right people. The earlier you can get into those circles, and the longer you can stay, the better off you are as the social network effects compound. This social capital gives you access to numerous advantages others have to work hard for and provides a barrier of entry of sorts. Simply stated, their social capital elevates them to a higher tier where they can surround themselves with the best.

    While that sounds disheartening, there is certainly room to join. Ingenuity goes a long way. Some of those folks were certainly born into higher tiers as you suggest, but sometimes making your own way provides its own benefits and access. At some point, everyone who has “made it” has had to work at it or have someone before them work to get them to where they are now. It’s very doubtful that the majority just fell into success. Much more likely is that they asked for help, were born into it, or worked hard to get where they are. And once you’re there, you’re not done. There’s a lot of maintenance involved to keep you where you are. Nathaniel Hawthorne observed American dynamism best when he wrote, “Families are always rising and falling in America.”

  3. @FinancialSamurai – I’ve played at 4.0 for the past couple of years and since it sounds you weren’t an ex-college player either, I’d love to hear what specific things you did that helped you get to 5.0 over the years. Also, how much of your game development was through coaching vs self-development?

    1. Hi Andy, I was recruited by a small Division III school to play tennis for them (Mary Washington), but I declined to attend the College of William and Mary due to perceived better academics.

      About 10 years ago, I self rated as a 4.0 level player, not knowing what the various levels were. I figured it was better to start low and work my way up. But after around four matches or so, the system disqualified me and bump me up to 4.5.

      I played at the 4.5 level for around five years, and one year I went 13-0, went to the playoffs, then had a 9-3 record, went to the playoffs and then got bumped up to 5.0, 4 years ago.

      I would say that having Great partners help, having high Tennis IQ in terms of strategy helps, And just continuing to put yourself out there no matter what. I never shied away from competition and always battled had any spot. I remember getting off a 14 hour flight from Asia, and playing a singles match straight from the airport because nobody else wanted to play singles. I won.

      You have to have a warrior’s mentality where you just keep on practicing, and never quit. I finished my last post at 2 AM this morning, because I wanted to stay on schedule. I could’ve decided to go to sleep and published late, but I didn’t want to fail.
      I finished my last post at 2 AM this morning, because I wanted to stay on schedule. I could’ve decided to go to sleep and published late, but I didn’t want to fail. Watching videos of the greats before a match helped me get into the proper mindset as well.

      You’ve also got to figure out how to keep on improving on your weaknesses. For example, I have a one-handed backhand. Are used to only slice it, but then I was able to comfortably hit it with topspin. Then about three years ago, I started working on the 200 back in so I could more easily return crosscourt from the Deuce side in doubles.

      Now, I feel really comfortable hitting a two-handed backhand return and smacking a one-handed backhand from the baseline for a more powerful winner.

      I truly believe mindset is 50% of the battle. It is having a tremendous belief in yourself that you can win and will crush your opponents.

  4. There are a few well known Hong Kong billionaires that relied on #5 as an early important cornerstone to building their businesses & wealth (e.g. Li Ka Shing).

    BTW, this is a great & informative site!

  5. I have played USTA leagues in New England, and there are a significant amount of sandbaggers. There are a lot of 4.5’s in the Boston area that won DIII national championships at NESCAC schools (mainly Williams grads for some reason) and are somehow a self-rate on a men’s/women’s/mixed team because the captain of the USTA team wants to make nationals. They crush everyone at districts and sectionals, and then get crushed by one of the other states. The levels in New England never seem to match up with what California, Florida or the Carolinas have, so I guess it’s all relative in the end.

    Personally, I enjoy the challenge of playing someone I know is better than me. Not only do I relax more because I know I’m not supposed to win, but I know it’s the only way to improve my game.

    On the topic of “who you know,” the tennis community is a pretty great resource. Tennis has played a role in landing me my current job and my current apartment. I also have some great mentors in my job field who play, and I’m grateful that I can ask for their advice. Once you have that common bond through the sport, you really meet some great people who are driven to succeed.

    1. One question I like to ask competitive athletes is: Would you rather get up to your maximum potential but always lose to the competition? Or would you rather achieve one level below your maximum, but win most of the time?

      It was an honor to get bumped up to 5.0 level in 2015, but after three years playing in the league, I’m good with the experience now. I’d rather play more people my age and win more.

      How about you?

      1. About 10 years ago I decided to learn tennis properly as a self experiment on mastery. A good book on mastery is Peak by Anders Eriksson. Gladwell, Golvin etc based their mastery books on Eriksson’s original research. I am not at the end of my experiment yet but have got far enough on the journey to strongly believe pretty much anyone can get really good at anything requiring skill acquisition.

        Your question is interesting. When I was crap I wanted to win win win. As I got better I got far more interested in maximum potential rather than winning. Of course I do tend to win more now because I am so much better than before but I am far more interested in my performance than the result.

        Have you considered singles and/or ITF seniors tournaments? This gets rid of the “stacked game” problems in my view. Tennis is actually pretty easy to learn with low barriers to entry. You do need a bit of money to pay for lessons (essential in my view) but then it is simply a matter of time to practice properly and hard work to get sufficiently mentally and physically fit.

        I much prefer singles anyway. Your progress is more measurable, much more fitness gain than dubs and no one to blame when you lose or steal the credit when you win. Also when you get that great satisfaction of beating a big hitting youngster they cant use the “I don’t play much dubs” as their excuse!

        ITF seniors (and I believe, additionally, USA have their own similar aged tournaments) has a wide ability range so you will win some and then lose some at those tournaments if you are 4.5 or 5.0. You can also combine it with travel interests as there are tournaments all over the world.

  6. Excellent story–I wasn’t sure where it was going at first, but it’s well written and then BANG it comes together and the analogies round out everything. “Face time” was and still is important for many things like promotion, help, and support. I know several very smart introverts that never seemed to get very far–and several mediocre, well-connected extroverts that advanced past their ability.

    A saying I never liked, but acknowledge as having merit;

    “It’s not principles but personalities that move forward.”

  7. siliconvalleyscrooge

    Talked with some buddies about landlord experiences recently.

    One said their mother rented out a family property at a profit, for while, until a tenant brought in a dog, against the rental agreement.

    She told the tenant to get rid of the dog (pit bull). Tenant refused, but the landlord didn’t say much since the tenant kept paying the rent on time.

    Ultimately the tenant left, but after a few months of trashing the rental unit.

    Buddy said, “Yeah, it was hard for a passive Asian lady to put her foot down with the problem tenant, even though it was within her legal right.”

    So, for point #2, being direct has its benefits.

  8. I always found running and tennis to be a great alternative to golf when it comes to networking.

    I enjoy running and it’s amazing how many past coworkers I run into at races and out jogging.

  9. I grew up fairly poor and went to a public university. I got my MBA at one of the top schools and it changed everything.

    What people don’t understand is that the education is a commodity but the network / relationships are invaluable. Knowing the right people opens up opportunities that you never thought were possible

      1. Politely butting in, MBA taught me that (useful) information is currency (not money). People who make money want to know how to make more money. People want to know who you know, what you know. Coming from an engineering background, I thought information was like, facts you know, data. Nobody had taught me to network, or the power of networking until I got my MBA. And that the ‘opportunities’ that MBA gets you isn’t like a red carpet, but more like it changes the way you look at things, recognizing situations that can be turned into opportunities.

        1. I went to a small branch of a somewhat prestigious university, but it was part-time and at odd hours between and after work, so I made few lasting contacts there.

          I found that getting an MBA didn’t really open many doors for me, but it has kept some from being shut in my face, and I’ve made measurably better salaries because of it. One employer even sent me to teach at a major university for several years as a member of the faculty. That taught me a lot!

          Probably the biggest advantage though, is it taught me how to invest and not to be shy about doing so, even with my own money.

  10. Lot of talk about tennis but good article. Young people need to be told this stuff, because even the very smart ones don’t always realize it on their own right away, and then are more likely to waste effort resenting it, or even flat out defying it, rather than working with it. Sure wish someone had had that talk with me before I finished college. Took me quite a few years to realize that being in the top few percent of people doing what I was doing wasn’t apt to get me anywhere I wanted to go . . . not just by itself it wasn’t.

  11. I feel like some clarification is needed here.
    Granted a social circle and a helping hand from a well off or high positioned person help but just “entering” that circle isn’t that easy.
    It’s very easy if that’s who you go to school with and grow up with, because you don’t care when you’re young how rich or connected a person’s dad is. You just like the same sport or video game and start hanging out. The friendship grows and the benefits come naturally later.
    For an adult making the transition it’s a bit like dating: you won’t find someone when you’re “looking for the one”. You’ll find someone when you’re doing your own thing and enjoying it and come across that person that shares your interest.
    Playing tennis helps you connect because you really like tennis. Someone else joining a tennis club to meet successful people would fail miserably.
    Connections are huge but they grow from real shared interest and experience. Really if you want a leg up you have to gain that connection first if you’re starting from zero.
    In terms of the reality of the stacked game…it’s the only reason I still network and go to any work “social” events. It’s not for me, I don’t really like most of the people there (this does not contradict my point above btw because at a certain point even without shared interest shared benefit can carry the load) I max out at time for like 4 real friends. It’s to keep connections because one day my kid is gonna need a phone call made for them from X to get Y. And I’m sure most people at these things tolerate me because at some point they may need me to make a phone call.
    Anyway my point is: this only works when starting from scratch when you really develop a shared common interest.

  12. As a fellow USTA player in Honolulu, I have also been in situations playing against higher level opponents and for you and your new partner to have lost 3-6, 1-6 is quite respectable. My playing level tends to rise when playing against a better opponent and allows me to learn and improve my tennis game. I take much more pleasure in making a higher level opponent (or sandbagger) earn a hard fought win than easily beating a lower level opponent. The USTA has age-based leagues which evens the playing field but I have seen matches where a much older player wins based on his experience, analyses, and tactics. I guess my point is that we should always strive for our maximum potential and there many ways to help achieve that.

    1. Thanks Wayne. It’s definitely better than a poke in the eye.

      I wonder how the competition overall is in Honolulu? Surely pretty good due to the ability to play year round. I like going to the Ala Moana courts and playing pickup.

      1. Hawaii usually does well at the USTA nationals. Majority of players here around 3.5 – 4.0 but there are also a lot of high-caliber former high school standouts and college players. Ala Moana courts are popular and I usually play pickup games on the mauka side. What I like about Hawaii is that people come from all walks of life and get along relatively well with each other, on and off the tennis courts. When hurricane Lane recently approached the islands, 3 strangers I encountered while filling up gas, shopping, & walking the dogs told me to ‘be safe’. This sense of ohana and aloha spirit is something I didn’t experience much growing up on the mainland and I feel extremely blessed to live here.

  13. Even though the system may be rigged, the US is still the land of opportunity. My family immigrated to this country with nothing and then on top of that my parents both passed away soon after. Yet I managed through getting good grades, working to pay for college, and subsequent hard work and good luck to have the opportunity to make $300 million by my 40s. All from merit and luck rather than connections or family money. And I know of dozens of other stories similar to mine, including my own siblings and my ex-CEO who’s now one of the richest people in the world with a $10 billion plus net worth.

  14. Love the post. Had a Crazy Rich Asians vibe to it.

    Some great advice here. Self promotion is indeed hard for myself. I feel like it is built into me to be more meek and modest given my Asian upbringing.

    Also asking for help has also been difficult. Here we don’t want to be seen as incompetent or stupid so you have to take a leap of faith.

    On the other end you also want to make sure your environment will allow for you to ask for help.

  15. Interesting to hear you say you’ve had this laid back attitude for too long to your detriment. You seem to have been incredibly proactive on many fronts, rather than just going with the flow – but I assume you’re talking more about promoting yourself. It’s all relative – we can always be doing more!

    I’m certainly in the laid-back camp at the moment, which I think point #1 Sandbagging works well with – hadn’t thought about it that way before but is definitely how I like to operate!

    Completely agree with all your other points for getting ahead, especially with networking and asking – assuming you have the drive and reasons to do it. I know it doesn’t sit well with many people but is a fact of life.

    Cheers, Frankie

    1. Hi Frankie – I’m proactive in solving problems. I definitely don’t just sit there and wait for things to happen to me e.g. engineer my layoff.

      When I first started FS, I was pretty good at outreach and stuff for about three years. Then I just focused on my writing. Although the site has organically grown every year, I definitely haven’t maximized its revenue or traffic potential because I haven’t been building relationships with larger publications.

      What I’ve discovered now is that my energy and time is less due to the birth of my son. My wife can’t really help much anymore as well. Therefore, I’ve lost anywhere from 4-8 hours of energy, and I have done plenty of 6am to 1am care+work days with 1-2 hours of rest in between. Once I realized I couldn’t keep up these hours, I had to find a better way.

      So, I’m proud to say as of today, I signed a syndication agreement with one of the largest publishers online. And I will also proactively pitch my work once a quarter now. Let’s rock!

      The CNBC article last week did wonders.


    1. Paper Tiger

      I had a boss who had added a twist he considered very important to that saying. His opinion was, “it’s not what you know and it’s not even who you know that matters, its WHO KNOWS YOU that really makes the difference.

      That was probably some of the best career advice I ever received and served me well.

  16. “Take advantage of your advantages”. I eventually realized that smarts and work ethic are a simply a type of advantage- genes, family, culture.

    Good looks, charm/funny, connections, inheritance, etc are just more advantages, some better than smarts/work depending on the circumstances. Nothing unfair in playing the hand you are dealt as best as you can, and doing what you can to take a good share of the pots. But I do draw the line at pushing others down to climb up, I wish more would feel the same…

  17. Ms. Conviviality

    I have noticed that the top 5 people one surrounds him/herself with makes a difference in their level of success. My husband is a good example because he grew up in a low-income family. During the 2008-09 recession, my husband’s painting business was not doing well since people weren’t spending their limited funds on repainting their homes. My husband’s income was impacted so significantly that he was facing foreclosure on his primary home. He didn’t have any family to financially assist and he only had ~$20,000 left on the mortgage. As difficult as it was to ask for help, he reached out to his college buddy who was a real estate investor. His friend gave him the money to pay off the mortgage and they agreed on a 2-year repayment plan with total interest of $3,000. We now live in a mortgage free house which frees up a significant amount of fixed expenses that can go into other investments.

    1. I love that your husband asked. Friends, and even acquaintances really want to help people in need. But if you people want to be so presumptuous as to try to extend a helping hand out of fear they might be insulting the other person’s pride.

      There’s no shame in asking for help, especially when you asked someone who you know or have helped before. What goes around comes around.

      1. Ms. Conviviality

        You’re right that good people do want to help others. My husband had made his request over the phone with his friend. My husband felt humbled that it took less than 5 minutes for his friend to call back and agree to the loan after he spoke to his business partner, his dad. It helped that the dad thought well of my husband too.

  18. Martial arts Mama

    I agree that you need to ‘befriend the unicorns’ to improve your status in life. However, it’s not because you want to get something from them, but because you are highly influenced by the people you surround yourself with, in terms of your values, ambitions, and work habits. After a certain age, your peers influence you more than your parents.

    My husband and I both grew up in immigrant families with very little money or status. We worked our butts off to get into the top schools in the country. This was the best thing we could have done since we found friends with like-minded goals and lofty ambitions to achieve. We were friends with them NOT because of their status, but because of their similar backgrounds and work ethic.

    When I now look around at our peer group from college, almost all of us have made it to the top of our careers and/or the top 1%. More importantly, we still have the same authentic relationships with each other. It is entirely too transparent and off-turning when people try to establish a relationship in the hopes of gaining something.

    In martial arts, I have found a similar experience by choosing to train at one of the top schools in the nation run by a US national team coach. Being surrounded by the top athletes and the hardest working ones, pushes me each and every day to get better and equips me far better for competition than by training at an average school.

    1. It’s definitely better to base relationships off common interests, and not because there is an agenda.

      But you’ve got to put yourself in the shoes of folks who didn’t get into top schools and who are on the outside, looking in. If you want to get on the inside, you’ve got to be proactive in making an effort to extend outside your social/economic circle. Too few do so.

      For me, tennis has helped me meet all different types of folks. And for you, martial arts has as well.

      We just can’t passively sit back and have things come to us. I’ve had this laid back mindset for too long to my detriment.

  19. I went to school with some really rich kids. Two of the richest girls stand out in my mind. One acted like a princess, wore designer clothes, and got a brand new car the day after she crashed her first one. The other was so down to earth, got awesome grades, wore plain regular clothes, and was really nice with a calm and sweet personality. I told myself if I ever became rich I wanted to be like the second girl.

    I came to peace long ago that there will always be people with more money than me no matter what I do and that there will always be people with a lot less.

    Interesting note you made on that person in college admissions never getting requests to help Asian students. Good to know!

    1. Good to know indeed! Self-advocate all the way. This is what I’ve been encouraging readers on FS since 2009, and what I will encourage my boy.

      I wonder how much of demeanor is DNA. Great to be that second girl.

  20. Marrying into wealth is extremely bureaucratic. Instead of working at Goldman Sachs you live in a family like Goldman Sachs. Pecking order and respect won’t come until the elders die off literally and you produce an heir…

    Dreading every family meal, the cold icy stares of relatives, imposing ridiculous traditional rules that don’t fly in America…

    Just go watch crazy rich Asians.

    1. marrying into traditional Asian family is just as ridiculous, wealth or no wealth. If I’m going to have a crazy Asian family, I’d rather have it with money too! Lol

      Yes even though I have more money/net worth than some of my Asian relatives, they still kind of mock/look down on me because of my status as an “immigrant” in America. Being “rich” isn’t just about how much money you have.

  21. Wow. There is a lot of actionable information in this post. Your life experience is pretty unique, and the practical examples for competition, work/results ratio, wealth-building, and especially moving in-and-out of social circles, would be very valuable to others if you ever think about writing another book.

    This must have taken quite a bit of time and thought to pull together, thanks for sharing FS!

    1. Thanks for the acknowledge JayCeezy. I’ve got a lot of stories to share, but at the same time, I want to protect everyone’s privacy as well. It’s been very insightful for myself to see how the extremely well-to-do live, and I do want to provide these interesting insights.

      I was walking around at the California Academy of Sciences today with my boy and wife. There is this mural of insect art on the wall, with names attached to each for donors. Lo and behold, I see the name of the guy I played tennis with yesterday on the lower row with his wife. So then I looked at the plaque to learn about the art and the donors, and the minimum donation amount is $50,000!

      I’ll make him get balls tomorrow when we hit again.

  22. Simple Money Man

    The circles are very true. The more you hang out with certain people, the more you can learn from them (positive and negative). It’s so important to choose your circle wisely and find a way out of a toxic one if you are a part of it.

  23. I really don’t care about the rich or the poor. Right now, I am middle-class in my country. In less than 5 years we’ll be just new immigrants in the US and have NOTHING. All our real estate back home is not gonna help, since we’re not renting yet and won’t sell anyway. We’ll leave part of our business here and take my web design skills and create a new one where we move.

    Even if we’ll be poor for at least a while in the US, it’s better for my daughter than to be back home, since she has access to better education and, if she is to become a good tennis player, than living 3 miles from Flushing Meadows might just be the push she needs.

    So it really depends … rich in a country that offers some possibilities or poor in a country where we can really fulfill our potential (if there’s any) .. we’ll take the dive and see where it takes us.

    I started from zero a decade ago and made it work, with hard work and dedication I’m sure we’ll be doing OK.

  24. You’re right. It’s all about networking. I didn’t think it matters that much when I was young, but now I realize I’m wrong. It’s all about who you know. That’s human nature. Unfortunately, I’m horrible at this kind of thing and I just have to go on my merit. It works well enough and I’m fine with it. Hopefully, our kid is better at socializing and networking than I am.

  25. Honestly while it may be stacked in some ways, I prefer it to stay as is. Why? The counter argument is someone coming from poverty or lower middle class has clearly defined steps as you mentioned above which they can use to get ahead. Each time the rules change it becomes harder for those climbing as they have to relearn the new rules. Those on top won’t notice as they’ve already made it.

    So with that all said I focus heavily on my short game. No home run million dollar a year job needed for me, perhaps my kids. (Though not sure they’d want it anyway) But 6 figure jobs and multiple 6 figure jobs are much more readily available. It’s a percent and numbers game. 90 percent of best does pretty well and is an easier hill to climb.

  26. Charleston.C

    I particularly like the part where you said “Do I wish I was 6’6″ with a 145 mph serve? Only when I’m playing tennis.”

    Drives home the point that an advantage in one situation could very well be a disadvantage elsewhere. Life is all about maximizing the cards you’re been dealt, that’s the only thing we can do.

    I’m a fan of these life-motivation posts, as much as the analytical investment ones. Keep up the good work.

    1. Very true Charleston. I’m 6’4″ and while it’s great for point sparring and running, it’s a hassle in other areas. Finding clothes that fit has always been challenging. Cars aren’t really made with tall people in mind. The air up here is also thinner so there’s the occasional lightheadedness. :-)

      All joking aside, there are advantages and disadvantages to everything. People tend to overlook smaller people which can be an advantage when practicing “Stealth Wealth“. You’re able to get ahead without drawing too much attention to yourself.

      It’s usually better to focus on what you have going for you vs. what’s not in your power to easily change.

  27. Great tips Sam.

    You are right about college admissions for Asian background applicants which I consider myself a subgroup of.

    I didn’t enlist the help of others promoting me and assumed my grades and test scores would speak for themselves which I am sure a lot of students still do. But it is a bit of a rigged system and others take advantage of to get ahead. It’s all part of gaming the system.

    Sandbagging is an interesting concept as well.

  28. Getting ahead in life is like most things. The most direct way isn’t what you think it would be. I always use the example of a good golf swing or throwing a punch in martial arts. In both cases, your body (or more precisely your hips) play a larger role in generating power than a layperson would think.

    Building wealth is much the same way. The “work hard and get gold stars on your annual reviews” approach will only take you so far. You have to promote yourself along and always look out for number one to really get ahead. Much like money, no one is going to care about your goals more than you.

    Great post.

  29. Great analogy. Seems like you should not try to make the game fair, but rather play by the rules provided. I still hate when I see or experience examples of this though, like consistent hard work not being rewarded due to a rigged system. Well done on the ranking, top 1% in anything with a large sample size is commendable although it should not decrease the enjoyment due to the system.

  30. Great article. Can be applied to any scenario where the challenger must meet an entrenched encombant.

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