End of the Road. What to Expect and How to Spot Them

When you reach your financial security levels, most people ask “what next?”

Instead of answering the question, which is impossible for each person, we’ll provide a sneak peek at how your actions will *likely* change. As noted this is from the perspective of a business owner and no longer from someone interested (at all) in Wall Street. In addition, we’re assuming you’re a single male. Finally, this post can also be interpreted as “how to spot someone who has made it”.

1) You Will No Longer Have an Interest in “Opinions”: A common criticism here is we delete comments from people we don’t like and mark them as spam so they never return. Why? Simple. We don’t care about the opinions of people we don’t know. When you’re set for life you think differently. This is not a forum for “discussions” (see waste of time) and should never be viewed as one.

Instead of doing what most regular people do, we do the opposite… The typical person will ask 10+ people their “opinion” on a topic to make sure they make the “right move”. When you’ve already made it in life you’re not wasting your time discussing topics. You’re spending your time getting things done. This is simply because a successful person *knows how to find the right answer*.

Most people don’t deserve the right to an opinion in the first place. Why? They have not succeeded in the topic they wish to speak about. Instead of polling tens, hundreds, or thousands of people to get an answer that feels right, you’ll have a clear and concise step-by-step process to finding the right person to answer the question. Instead of asking strangers or acquaintances, you’ll go through your personal process and find the right person. Once that person is found, you pay the price to obtain the answer from them and execute as they say. 

2) Disconnection from People: In our prior post, explaining how money will change your life, several unsuccessful people attempted to ignore the word *temporary* when we walked through the *temporary* negative effects of money. This is because your average person is looking for an excuse to avoid getting the things they want the most (fear of failure). This disconnection will likely ebb and flow depending on your own personal state. But. For the most part, it will be *temporary* in nature as you learn to hide your wealth from society (assuming that is the path you take).

It is certainly not normal to wake up on a Monday or a Saturday and not know the difference. For most, the days are clearly different as they have people to report to and deadlines to meet.

Interestingly, when financially set, you’re better off creating a reason to get on a somewhat normal schedule on weekdays to create your own grounding mechanism (avoid downward drug and alcohol spiral). This will help bridge the disconnection gap a bit. The gap will always be there. But. You’ll find ways to ground yourself for a more “relatable” life style.

Hint: there is a reason many rich people turn to charity work, forced human connection.

3) Nothing to Talk About: Unless you’re out with friends to meet other new people, you’re not going to have much to say in one on one conversations. You’ll come off as eccentric already. Most people have many issues they want to vent about while your entire goal is finding new challenges or sources of entertainment (dopamine rush without the health impacts).

You’re certainly not going to blow the lid on exactly what you’re doing so you’ll find yourself avoiding the topic everyone talks about: Work/Money. Ironically, once you have it, you don’t talk much about it during your *personal life* (again assumes you’ll be a stealth wealth person).

Since you have less to talk about, your social priorities will shift quite a bit. The only way for you to be enticed to go out and have fun is if there is someone you specifically wish to meet. Otherwise, you’ll likely go out solo and have a carefree night without being interviewed for the 100th time about “What is it that you do again… exactly?”.

4) No Stress: Assuming you’ve learned the art of stoicism, you’re not going to have any stress in your life at all. Your only interest will be in maintaining your current health, which is worth more than every single cent in your bank account. If we think about stress, it usually involves negative things that could occur to you if you fail at doing something. Therefore, if you can fail at anything and still be fine… it is almost impossible to become stressed. Your only stress will be self inflicted through physical exhaustion (fitness) or product creation (mental stress).

The real takeaway is that no one can apply stress to you anymore because they have no control over your life. Similar to creating forced human connections by picking up a routine that is done during the weekdays, you’ll create self inflected stress. Most will turn to the money game, trying to increase the numbers on a screen since it is the hardest game to play. There is no fun in life without a challenge.

5) Irrational Buying Behavior: You won’t think about *planning* for purchases anymore, you’ll simply look at items you want… buy them… or go through long stretches of buying nothing. If you’re earning more than you can spend the behaviors you exhibit won’t make much sense. Sometimes you’ll find yourself buying many items at once for prices that appear to be inflated (you won’t care) and other times you’ll delay purchases for long periods of time because you don’t feel like spending the time to obtain them.

The key here is that planning is no longer in your vocabulary when it comes to general goods/products. You’ll learn that possessions don’t matter much to you and all of your planning will surround memorable life events (trips) that take up material blocks of time.

6) Skyrocketing Time Value: The value of your time will increase at an exponential rate, you’ll become more protective of your free time on a weekly basis. Tolerance levels also decline at the same rate. This means you’re going to quickly change priorities and where you spend your time will rapidly evolve on a monthly basis *at minimum* as you review each week and the time you used wisely or burned each day.

An interesting note is your hobbies will evolve as well, for better or worse this blog will become a more sporadic hobby in the future. We haven’t seen much need to write anymore. We feel the content on the blog is already enough for anyone with a high IQ and competitive drive to succeed without silly motivation or discussion.

On a more positive note, we’ve officially started creating a basic product we wish we had several years ago. When our internal metrics are hit we’ll go ahead and press publish with limited “marketing” since books are not good products for money making purposes (Why? it is non-recurring revenue).

7) Rapid Learning of Complex Topics: Since the two types of growth are essentially financial and mental, you’ll find time to dive into complex topics. Each month (or year) you’ll find a new “difficult” topic that interests you and become a quasi expert in the field. We use the word quasi as you’ll know enough about the field to have interesting questions, but you won’t have the tools necessary to solve those questions without giving up another major slug of your time.

Maybe you’ll be different but every 3-6 months you’ll find the *truth* about a new topic which only makes you much more dangerous as people will be unable to lie to you easily. You’ll find yourself saying the tried and true “Wow, I don’t know anything about XXX can you tell me about it?” only to see if the person is a liar.

8) Mainstream Understanding: Instead of being part of the mainstream, you’ll understand the psychology of the mainstream. This is vastly different from being a participant as you’re simply selling your items based on mainstream philosophies while you avoid partaking in any of them. To put it more simply, the things you find fun… people will loathe and the things you loathe… you’ll sell, because its what the mainstream wants.

There is nothing wrong with selling mainstream products as that is where the market is. The joke is that your own preferences never match up to the needs of your average customer. If your product works and you use it yourself… the way you sell it would unlikely ever work on yourself.

9) Stable Dopamine Levels: The largest rush you’ll ever get is when you’re free. There is no doubt about it and once you’ve gone through the temporary drug/alcohol spiral to try and chase that next high, you’ll settle into a steady emotional state. People can yell at you, they can suck up to you, they can even attempt to get physical with you… Your emotional state won’t change much. Unless your life is actually at risk you’re unlikely going to get a material adrenaline rush.

This does not mean you have no emotions, it simply means you will always be stable. The highs and lows are smaller and day to day changes are quite irrelevant. Try to envision a buddhist monk and you’ll get an idea, the only difference is a slight smile to your face as you won’t require the intense mental concentration.

10) Distain for Authority: So long as you’re not breaking the actual law (sent to jail) you’re not going to have a shred of tolerance for anyone who attempts to act as an authority figure over you. In short? You’re no longer employable.

An accelerated increase in your pushback to anyone telling you what to do will be seen in short order. We can’t speak for the rich men with wives who boss them around as we’ll never understand those folks, but the rest usually exhibit personality traits of a recluse. Historically, it was bad to be ostracized from a tribe as it was part of basic survival. In this case, the isolation will be self inflicted as answering to someone will not be on the priority list.

11) Inability to Be Bored, Only Frustrated: Assuming you have a type B personality, you won’t find yourself being bored. You’ll go through spurts of being social and spurts of learning new topics as stated above. There are too many topics to learn about and too many places to see to possibly become bored for long stretches of time. In fact, you won’t be bored for short stretches of time.

The one downside, is delays in time (airplane delays, traffic etc.) will drive you nuts. Burning of your time is one of the rare items (next to health/your family) that will have any ability to impact your emotions negatively. This shows up in two ways: 1) if it is a travel delay you’ll scramble to find productive things to do… likely fail at doing something remotely and 2) if someone is wasting your time, you’ll pay the bill and leave or simply leave the conversation abruptly if there is no reason to wait.

12) No Impact from Rejections: This is a broad topic but can involve trying to sell a product to dating. When you know that you’re already set, it becomes impossible for anyone to rattle you with a “no”. If a person doesn’t want to buy your product you simply move to the next. Similarly, if you’re chatting to a girl on a date and she is negative towards you it won’t even be an after thought. Previously, most people will feel some emotion when hearing a “no” in either work or play. But. Those days are long gone and you can even take an emphatic no publicly. The event will be forgotten within 24 hours.

You’ll only remember positive things from your past as the negative items won’t seem relevant anymore. Again. Forgotten instantly.

13) Decrease in Mental Circles: When you’re doing everything to climb up, your brain is “on” constantly. You’re trapped in your head for the most part trying to figure out the next move. When you’re done, it is *extremely* easy to turn this function on and off. You could have emails, phone calls, text messages and a siren going off in the background but you’ll be able to tune out all of it at a moments notice.

This is critical as being trapped in your mind actually reduces work performance. Being able to shut down all thoughts as if you are at rest will allow you to learn and create at faster rates than the past.

14) Annoyance With Travel: A small topic but a dead giveaway someone is very well off financially. They absolutely hate flights that are not direct. They absolutely hate being in the airport. Finally? They also absolutely loathe specific cities and will do their best to avoid them at all cost.

“To travel to love to laugh” is something younger people want to do. “To see the world”. You’ll be tired of moving around a lot and will have a few set places you will call home.

15) Everyone Knows Each Other: The triangle gets smaller and smaller on the way up. The reality is that anyone who works in the same industry as us (no, not Wall Street anymore) has probably already crossed paths several times. In fact, we’d wager that if you’re in the top 1% (keeping it simple) in your industry… You’ll know every single person who is at or above your level by first name and last name basis within 6 months. Simply no chance it won’t be the case.

Funny enough, when you go to events/parties… Everyone will know the same people as well. This is why it does not make sense to put your face out there unless you are willing to pay the toll of being famous.

Summary Notes

Below is a quick summary of what to expect and we’ll also throw in some fun nuances and see if anyone recognizes similar traits in people they know (that are financially set).

– No interest in opinions, therefore will come off as a “know it all” and will generally dislike people unless prefaced with a reason to be speaking to them.

– Generally disconnected from society creating a largely eccentric personality by default

– Does not want to reveal much about his/her life with new people and therefore avoids all topics that most people chat about (work/stressful situations)

– Appears to be largely carefree

– Irrational behavior when it comes to spending habits

– Difficult to get a hold of unless “sold” on the event

– Interested in many new topics and continues to learn a new obscure item each year

– Understands human psychology well, yet all decisions on personal basis appear to be done with cut-throat logic

– Un-rattled emotionally, yet easily annoyed when treated like a “regular person” by a regular person.

– Zero tolerance level for wasting of time or being told what to do (unless specifically asking an expert and likely paying for said information)

– The word bored is killed from the vocabulary list

– Cannot seem to understand negative feelings associated with rejection, because rejections have no impact on their lives

– Clarity of thought

– Speed of travel is more important than comfort of travel (will travel “in style” if it does not impact flight duration)

– Seems to have the same biz contacts that remain unchanged for many years


  1. Ambitious says

    This came at the perfect time. I just randomly found about $700k in a bank account putting me at nearly $2M net worth even after paying horrifying high US taxes. I have been drinking more (not getting drunk, but it is extremely fun to take hot girls out to the nicest cocktail bars in town)…

    This post is on point.

    “It is certainly not normal to wake up on a Monday or a Saturday and not know the difference. For most, the days are clearly different as they have people to report to and deadlines to meet.” – You’ll only realize it’s Friday when everyone starts talking about going out. It surprises me every week LOL.

    “you don’t feel like spending the time to obtain [material items].” This makes it hard to furnish your apartment lol.

    “instead of being part of the mainstream, you’ll understand the psychology of the mainstream” —-> You’ll see marketing….everywhere…it is horribly funny.

      • Ambitious says

        It would be revealing too much if I explained. It wasn’t just in “one account”, but I was pleasantly surprised when I finally organized everything. I thought I had about 200k in there, so I guess I was only surprised by $500k, but still. I was speechless. 😉

        PS. This article by Cernovich is good. http://www.dangerandplay.com/2016/03/26/why-rich-people-are-miserable/

        You can be incredibly happy being rich, but only if you weed out toxic influences in your life, and spend some time “enjoying” yourself in a positive manner. Many rich people are miserable, but most people are miserable in general.

    • Thomas says

      Yep. I’ve noticed all rich men who are controlled by their nagging wives live miserable lives. (ha, that rhymes)

      When you’re set, marriage definitely becomes a business contract with no room for error. Hell, why even include the contract. It doesn’t need to be set in stone, or ink for that matter.

      As for my childhood, getting stuck with incompatible (and extremely annoying) siblings is the worst. They know exactly how to get on your nerves.

  2. narmno says

    Some rough ideas:

    – Reads all the time.

    – Writes to remember things. Deletes 90% of what he writes. Doesn’t share his writing with the public.

    – Obsessed with assimilating information in a systematic way (mental models) and 80/20’ing everything with minimal bias. Visualizes his mental models. Dreams about them.

    – Chuckles when he sees news headlines.

    – Thinks 30’s and 40’s are the prime of a man’s life. Comfortable with death.

    – Nicer to women than the average person, though some of his private opinions aren’t in lockstep with what’s concerned “nice.”

    – Regularly reads about health, psychology, politics, mindset, etc. and focuses on finding connections between disciplines, as a way of compressing information.

    – Can justify each of his actions three ways: (1) quantitatively, (2) in terms of virtue (tradition and aesthetics), (3) in terms of mindset/psychology. Intuitively knows the downside of every action he takes.

    – Can easily (and brutally) rate the merits of a book.

    – Has mastered the ability to build up skill in an endeavor (e.g. a sport) using consistent routines.

    Trump also talks about the concept of “controlled neuroses.” It means being paranoid about certain parts of one’s life (an example in your post is time use) in an effort to reach a higher level of performance.

    I think many of these habits are fine to do even if you’re not quite on track to $1M by 30.

    It’s a shame that many high-IQ people don’t learn about this till their early 20’s. Intelligent should be reading the classics when they’re 8.

      • narmno says

        Visualizing where you want to be is, I think, a great habit. It’s also fun as hell.

        Here’s another batch of 10:

        – Can write an interesting book from memory. This comes off in conversation (though he may rarely engage in conversation since he’d come off eccentric). Most people have an interesting quip or two (“once I drank a gallon of Coke!”). He’s deeper than that.

        – Can’t stand watching movies. Too low-bandwidth.

        – Doesn’t flatter (except strategically; e.g. complimenting an author on his work). Knows everyone’s comfort zones and self-serving biases when talking.

        – Has mastered indirect language.

        – Doesn’t use touchy-feely words like “appreciate” or “problematic” in conversation. Precise vocabulary, including many simple expressions and turns of phrase.

        – Knows so much, he never nitpicks.

        – Such a good understanding of fashion, he’s unimpressed by clothes.

        – His clothes are carefully picked, but they do not identify him with any well-known group (especially a self improvement group). Also knows which type of clothes each group wears, and why.

        – Respects people who made their money on their own. Doesn’t bash poor people. Blind to wealth.

        – Is unsurprised by his success. It was all a system.

        How about another batch of 10?

        – Never talks business with women (or regular people).

        – Knows whether a song will be a hit or not after listening to half of it once. [ Maybe not true for everyone. ]

        – Sleeps well most of the time, but unfazed by lack of sleep.

        – Unbothered by noise or unexpected events. Can easily turn it around. Trump is like this.

        – Positive when talking with other people.

        – Insults don’t affect him emotionally. He has already carefully examined his weak spots.

        – Doesn’t like talking with normal people but remains polite when talking to them is needed. (He doesn’t even seem impatient.)

        – Doesn’t bob his head to music. If he listens to music while working, listens to the same song over and over on headphones.

        – Never says something unless he means it.

        – Big ego, but not immediately evident in conversation.

        Another batch of 10? What about technical skills? Business skills? Fitness skills? Grooming skills?

        Nah, I don’t want to take over the comment section and bore the hosts. Regardless I think this is a really fun exercise, and dozens of these flow out as I type.

  3. YMoney says

    Having finally launched my first business, I have a LONG way to go to full freedom, but I just turned 25, and my beliefs are already changing about how fast I can get to that level (hint, its before 30, think its compiled confidence from previous Wall St experience and accomplishing other things)

    This being said, what I’ve seen is going through the process of making money completely on your own from an idea to the cash inflow of that first $1, you gain a new type of confidence. Things that initially seems confusing and hard, seem like non issues, and old thought patters seem stupid.

    I’ve already seen hints of what you guys say in this post, and its not because I’m financially free, but I think its because of the new confidence gained in the process of building something:

    As an example, and one that I’ve seen happen on my path already and its SUPER annoying:

    On # 1) People start by agreeing with you that its too hard to do something (build a business), but then when you accomplish it on your own and then tell them you did it or built something, they ALWAYS will then have their own opinions on how you can do it better when they havent even done it! They also have opinions on how you can grow it to peak levels, when they don’t even know what it took to launch…

    Lesson: Either don’t tell them you did it, tell them you did it and play it down, tell them you did it and they helped you (they didn’t), tell them you did it listen to their advice while daydreaming and then smile and nod at them.

    Awesome post!

    • Anon1 says

      >On # 1) People start by agreeing with you that its too hard to do something (build a business), but then when you accomplish it on your own and then tell them you did it or built something, they ALWAYS will then have their own opinions on how you can do it better when they havent even done it! They also have opinions on how you can grow it to peak levels, when they don’t even know what it took to launch…

      LOL reminds of that saying: “Opinions are like assholes. Everyone’s got one”

      Adding an addendum: losers seems to have so much more. Opinions that is

    • regularPerson says

      > tell them you did it and they helped you (they didn’t), tell them you did it listen to their advice while daydreaming and then smile and nod at them.

      IMO, it’s risky giving them kudos for something they haven’t achieved, because they may believe it and start bothering you ass to give them “they well-deserved credit”, which is 100% untrue and unfair to oneself.

      This could signalise to other regular losers, that saying some bullshit advice to you, means instant payoff fo them.

      And then, you can’t say “NO!”, because they gave you their “precious advice” (bullshit) and thanks to “them” (own idea + hard work), you’ve made it, so they deserve “their” pay.

  4. says

    Already starting to feel these effects, particularly the can’t tell the difference between Saturday and Monday.

    Most likely due to the fact I’m spending all free time working on the business. No where near the financial freedom goal, though.

    Age 24.

  5. The_Eccentric0 says

    Really want to thank you guys I’ve turned my income around dramatically from being in the Marine Corps make 24k a yr to less then a yr out pushing almost 200k. Feels like I’ve wasted so much time.. thanks to your reading I just bought a running dropshipping ecommerce business that I have to work on less then a hr a day that bringing in bigger bank.. Next goal is to hit 500k before 30 (28 now and now in WS sector) thanks to you guys I’m more then confident I can hit that before 30.

    I swear you could make a book and have each chapter as a post.. or just copy everything to PDF and make a bible.
    Keep it up fellas!

  6. says

    I’m experiencing a lot of this already only I’m not rich just self employed. Still striving to make more money but yeah definitely lose track of days and absolutely disdain authority. I hope this means I’m on the right path. Not giving up at all.

  7. says

    “It is certainly not normal to wake up on a Monday or a Saturday and not know the difference”

    I would add: It is certainly not normal to wake up and have no idea what day of the month it is.

    Fantastic post.

  8. says

    A comment from a guy moving from broke to not broke at a relatively accelerated pace.

    I was talking about barbecuing yesterday with the girl, and she says we can just wait for one of our friends to host it. I love my friends (lifelong guys and great) but the first thing I blurted out was “Then I’d have to sit around and talk about stuff waiting for food”.

    Man the disconnect is weird (especially for an extrovert), but it is VERY real. In the past year I have lost all common interest with people (unless it is boxing or talk of the future of science)–and I’m not even close to the end.

    The time valuation is super real (laughed my ass off at the direct flight thing). But as isolated as I’ve become, I’m happier than ever.

  9. says

    This post is so true.

    I’m not nearly as successful as I plan/will be, but I experience all of these already.

    Success changes you big time.

  10. AC says

    If I understand correctly your product will be a book…

    Great, looking forward to it.

    Some extra patterns I ‘ve noticed of people who have made it:

    – They engage in a hobby neither heavily nor lightly. Their focus is elsewhere, but they want to be good in that hobby and beat other people at it. At least be competent, but not champion.

    – Most of them have a weak spot for something good that is consumable. It can be good food, good drinks, good wine, good cigars, good drugs, whatever. It must be of high quality (usually slightly expensive) and give a dopamine rush.

    – They respect the hustle especially in younger people (<30 yo) regardless of the amount of money it brings.

    – They rarely drive insanely expensive/fast cars, except for the occasional day off / for fun. Most of them pick a BMW / Mercedes or a jeep for the family.

    – They don't reveal much about their work, industry or work secrets. They will keep the "work" topic pretty generalised and will play themselves down a lot. When one wants to cut off the conversation when it goes to what "he is doing for a living" it's almost a dead giveaway he has something pretty good going for him.

    These are from personal observations, nothing set in stone.

  11. RE Guy says

    “We can’t speak for the rich men with wives who boss them around as we’ll never understand those folks”

    – Red Pill in business, Blue Pill in romantic relationships (as much as I dislike these distinctions for their oversimplification, they are useful here).

    It’s simple really, to become self-sufficient in a sphere there are a number of pre-requisites.

    One is seeing the “truth” of the people involved, in business and in romantic relationships this means seeing how the other person has interests not completely aligned with your own (and that you have interests not completely aligned with there’s), coming to peace with it, and finding a way to get a deal done anyway (assuming the two of you can find enough overlap). Truth in business might mean hiring someone knowing that they may try to one day leave you to defect to or become a competitor and treating them with an appropriate amount of distance, truth in relationships might mean giving up the maddona/whore fantasy and not believing you’ve found the perfect little angel because she’s the first 9+ who will actually come near your penis somewhat voluntarily.

    Another is being willing to walk away / be on your own for a period of time while you wait to find a deal that suits your needs. For business this might mean living meagerly while you start out a business and reinvest all profits. For relationships this might mean grinding it out at bars and clubs pushing yourself to quickly lay 7’s, 8’s, 9’s etc. increasing quality while refusing to submit to the boyfriend role.

    Yet another is the time and energy needed to develop and maintain a skill set. To build a business or to learn game takes time and energy, and unless you start relatively early in life, it can be difficult to do both effectively. Remember one thing, time is always ticking by no matter what decisions you’re making and you’re going to have to answer to that (both to yourself and to others). Trying to date attractive girls in their early 20’s will be a lot harder for you in 30’s if you have neither a solid bankroll or solid game (preferably both, or at least the foundation of each).

    The paradigm I have for all of this is that there is Red Pill and Blue Pill for business and game and there are all four combinations out there. PUA’s are BP(Bus)/RP(Game), The guys you are talking about (I’d include financial samurai in this, I’m prepared for the flaming (and I haven’t forgotten our bet on Trump Vs. Hillary)) are RP(Bus)/BP(Game), regulars are BP(Bus)/BP(Game), and this blog and people like The G Manifesto are RP(Bus)/RP(Game).

    I’ll qualify the PUA statement: Even if they are trying to run a business, often a PUA business, they are rarely very good at it (although they are aware usually of the futility of plugging into “the system” and working for “the man”). More often than not they are just negative about business/money which is another reason that they may have sought out PUA in the first place. To put it another way, they focus on leveraging game skills to get girls in absence of other factors (such as money) because they are incompetent at maximizing those other factors (also this helps explain the “looks/money/status don’t matter” maxims, it’s coming from guys who can’t/won’t obtain them i.e. a rationalization (or it is marketing directed at those who can’t/won’t obtain them, encouraging rationalization in others i.e. sales)).

    So the mirror image of the PUA is the rich guy who is owned by his wife. Again, this doesn’t mean he is totally unaware of male/female dynamics or his desire; his wife may very well be very attractive (he is rich and providing her an early retirement (23-27) by the way, hard to say no to that package). It’s just that he hasn’t done the work/introspection to get there. To put that another way, he makes more and more money so that he doesn’t have to deal with the realities of game. To paraphrase this blog: Once you reach 7 zero’s in your bank account, you’ll be a 7 for life. – True enough. But assuming all things are equal (being a 7 means dating a 7, roughly), then it is a heck of a lot easier and quicker to learn enough game (and fix your looks enough) to lay a 7 then it is to make a million, especially in today’s “liberated” culture, assuming there isn’t a personal emotional blockage to the process.

    Or to put it concisely; the PUA creates a self-sustained reliable system to get girls but not money, the rich guy/dominating wife creates a self-sustained reliable system to get money but not girls, the regular has no system and must rely on others for both, the playboy has systems for both.

      • RE Guy says

        If I have anything to say about it I’d go with Mase.

        That was a fun throwback. It’s positive and upbeat perhaps to the point of being corny. And the part of the video where he wears a shirt with a giant picture of his smiling face on it was great.

        People often describe me as always being positive and occasionally misunderstand it to be some sort of pollyannaish outlook (not wanting to “burst my happy bubble”). Sometimes I’ll ask someone how they are and they’ll say “Could be better” to which I’ll respond “Could be worse”, or for instance complain about working that day to which I’ll respond “But at least you’re getting paid” etc.

        It’s important to be relentlessly positive and solution oriented, if your goal is to get the most out of life, in my opinion.

      • RE Guy says

        And. I might as well mention on the subject of positivity and solutions, this is why I avoid the whole discussion of feminism and the associated complaints. It’s silly because those guys would be better off learning how to seduce women effectively including increasing their own value, and because feminism was/is a movement where wage class women scapegoat wage class men.

        If you’re reading this, why the hell would you want to be part of the wage class? Read the post on escaping the middle class (and the rest of the blog). It’s a joke, I don’t care if women get equal pay with men, they’re both getting ripped off by working for someone else, so she fights for the right to be paid 1/9 of the value she creates instead of 1/10 (and he takes a pay cut to compensate). Who cares? They’re both dumb.

    • Ambitious says

      “the regular has no system and must rely on others for both”

      I don’t know why, but this made me crack up laughing out loud. SO TRUE!

      Money without game will bring a lot of unhappiness.

      Money + game + stoicism = amazing life.

      In the last couple of months I’ve had multiple relationships and random girls, and I feel 10x happier because of it. Living in a penthouse is not fun without some girls.

    • says

      What a fantastic comment once again.

      I wonder if the desire to leave a legacy through bloodline will ever kick in for the boys. You once said one of the writers was considering it. I’m curious to hear about it if he goes through with it.

      Cheers from France.

      • RE Guy says

        I don’t know if I said specifically that they are/should be considering a bloodline legacy, or if you were referring to WSP themselves. However I believe that some sort of legacy is necessary for psychological health past a certain age/success level; at some point it can’t just all be about you.

        I know WSP and I share that outlook. Whether or not they do that through a blog, mentoring young promising guys, a legit product that improves people’s lives etc. or through having children is up to them. It could be said that having children is the default and unimaginative way to create a legacy, unless of course you are Trump and trying to create a dynasty.

        Laughed out loud at top five worst ideas of all time.

    • Markximus says

      Great post.

      I really hope you start your own blog or continue to contribute to WSP because I find that your posts (such as this one) more nuanced in describing the framework to win in life.

      I didn’t understand it (and actually cringed) when I saw someone who I respected in business get bullied by his wife. Your post makes things so much clearer.

      Thanks Re Guy and WSP for improving my life. Sad to see WSP updates to be more sporadic but agree everything one needs to know about success is already spelled out here.

  12. SM says

    I just got on the freeway. Early 40s, in the same industry since I was 23. Learned a shit ton of information in that time along with building a massive rolodex of connections. Have just begun leveraging all of it for a return higher than anything that I could achieve with my small brick mortar business. I know what will get me to where I want to be by age 50 and that is what Im focusing on. Its a great feeling to be headed there. Its funny because I’ve been self employed for the last 10 years of my life. Its a business with its ups and downs, gives me a living (sometimes barely) yet Ive always acted similar to the way of people who have “made it”. I don’t suffer fools nicely, limited patience, ruthless on not waiting my time on frivolity, avoid assholes and leeches like the plague and considered rather eccentric. A buddy of mine has compared me to Howard Rourke in the Fountainhead. Now that Ive discovered the mechanism that will move beyond the business that gives me a living and gets me rich, it wont be too hard to fit the mold.. temperamentally/personality wise Im already there.

  13. Mr. Grey says

    You mentioned the part about rich men that have wives bossing them around and I have a theory as to how it got to that point, they gave into mainstream society. In my view, mainstream society shoves “youth” (live it up while you’re young!) and romance down everyone’s throats.

    An example of media and mainstream society shoving youth down everyone’s throat is how they push college as being the epitome of life (“best 4 years of your life!”). How you will never be around so many potential friends and life long partners, ever. I believe that a lot of these rich guys who had the potential to make a lot of money ended up giving in to the mainstream narrative about social life and romance, how it is so pedestalized by the media, and then they ended up getting married before 30.

  14. Scott says

    That’s a first. You guys mentioned family in your twitter along with health and freedom. I thought family didn’t matter since you guys always talk about avoiding kids and marriage. I guess you guys changed your mind.

    • Radduck says

      No change. Family refers to parents, etc. WSP’s message over the years: treat family with the same standards as everyone else. If they bring you down, distance yourself (ruthlessly). If they are a positive influence and deliver value, you’re incredibly lucky — keep them close.

      But either way, don’t let family members control or decide your life.

      “If your family is bringing you up and helping you grow, then hold on to them tight, for most this is simply not true.”

      “16) Turn Family Into Friends: For many, your family members are dragging you down and for others they are a positive in your life. The key is to separate your life decisions from their opinions – their opinions should have no weight on your emotions. At this point you should not use your family as a safe haven in life. If you lose your job, if you want to move cities, if you want to take a risk, it is on your shoulders. Remove the safety net.”

      “Your family only matters if they are helping you with positive reinforcement.

      Standards should be applied equally across the board. You wouldn’t let a friend try to bring you down so why does your family get a free pass?

      If your family *is* helping you… then absolutely keep in touch with them! A good family member is probably equal to two friends you’ve known for a decade or longer.”

    • Wall Street Playboys says

      You must be new here. There is no change.

      If your immediate family is helping you keep them. If they are dragging you down you must separate.

      If you want kids, don’t get legally married and still have kids

      All set, no change in mind whatsoever.

  15. Yaze Sun says

    I am still not clear on the definition of “making it”. If “making it” meaning you never have to work again, I think that is too low of a goal. My definition of” making it” financially, is having assets worth of at least 1 billon USD dollars (2015 level) and enjoying an income of over 50 million dollars a year ( an average of 5% annual return which is reasonable) , besides that, I also want to have a gulf-stream private jet and a over 20 meters yacht that is ready to go at moment’s notice. And that is just my financial aspect of making it, i also want to have my contribution to humanity like what that gates foundation is doing, funding and running a campaign or project eradicating a disease, educate 100000 children something like that, I would not go into the details.

    But i do agree money comes first and is the most most basic part especially when it comes to doing philanthropy ( but trust me it requires more than just money, it takes time, effort, creativity, and time) . I laugh at people who said if I was given billions dollars, i can create a foundation just like gates’. Look like all the billionaires, nobody is running a foundation as well as Gates( i guess that is probably why warren gave 30 billion dollars away).

    My point is the end of the road for many people is too low of goal, aim high
    Many times your end of road are just some else’s start of the road

    • some random douchebag says

      I started writing a serious reply, but then I re-read your comment.. – Are you trolling? Because you obviously haven’t “made it” by any definition. Congrats, I did bite.
      If not, the whole post defines someone who “made it”.

      • Ambitious says

        Lol. I wrote a long serious reply as well, and then I deleted it.

        I’m glad we’re on the same page.

      • Eric says

        No, I am dead serious . Life is a game and we only get to play it once . Why not play it to be the biggest winner . Too sad most people think too small and play it to lose .

  16. Southern Cooler says

    An all around useful blog to which I’ve directed my son.

    I’m a bit over 40, didn’t per se become an entrepreneur until 29 and enjoyed a significant 8 figure personal exit a year ago. I can attest your lifestyle notes are dead on – there are very few people who understand or live through these experiences.

    I’ll add one item worth consideration: every man has a different level of “enough”. I’m not sure where mine is today – the effort for more great entrepreneurial runs is tremendous. One man will sit on $10M, another $100M and a very few never stop trying to become Billionaires – the drive is so strong.

    I’m trying to become much more well rounded and not launch more ventures which may not be worth the personal time investment. It is not easy though.

    Anywho, dead on!

  17. says

    I resonate with most of the things you’re saying in this post… HA being pissed at long haul flights and other time wasters. That’s me all day

    After a certain income/NW you just don’t have time for that nonsense

    I’ve never read something more relatable, disconnection from people is a real thing once you crack 7 figure income…

    This book on Audible might increase your happiness even further, it’s been helping me a lot. I definitely have the same neurotic, judgmental thoughts that you guys do about people in general. I still think getting along with the average people is good ROI on your quality of life though. Sometimes the posts get so harsh that I cringe because I think the same things and realized it’s been hurting me…


    Let me know what you think of that read, it’s like $6 on Audible

    • RE Guy says

      What’s up A? If you’re the same guy who made bank from before then I think I understand this comment very well.

      “I definitely have the same neurotic, judgmental thoughts that you guys do about people in general.”

      So a neurotic thought is just one that is unproductive towards your stated goals. Judgemental is contempt where you see yourself as different, and better, than the other person. So the questions are:

      1) Do these mindsets help you and what mindsets would help you reach your goals?

      2) When it is appropriate, if ever, to be judgemental or practice contempt?

      So for a start you have to understand that contempt is a form of ego protection, separating your “self” from others, and that compassion and humility is a form of ego death, connecting your “self” to others.

      Now, who is worth connecting with?

      Just asking that question, consciously, puts you ahead of 80-90% of the population. Working to execute on creating those connections, including being of value to the people you value whether that means self-improvement, controlling your emotional state to always be happy and positive, disciplining yourself in all areas of your life (integrity) etc. puts you ahead of 95%-99%.

      So an effective mindset would likely be to choose to invest in relationships with people you believe will give a good ROI, while finding ways to quickly mesh with largely unavoidable people who won’t give much ROI in a low investment and low risk manner (i.e. “smile and nod”). So in a sense you practice contempt for regulars who you know don’t get it and who you don’t want to spend the time educating (especially since it may take months or even years for them to catch up, which if they aren’t your children why would you even invest that much time and energy (which is also why having children is such a hassle, raising them from little savages to well adjusted adults plus paying for them)). The last part of this is the “don’t wait in line” / “pay for convenience” which is also to avoid as many regulars as possible etc. Or you could say creating “buffers” between you and the masses.

      And your suggestion about making connections with others and that being instrumental in creating a happy life is crucial, it’s absolutely necessary. Just pick parameters that you value such as ambitious, disciplined, humble, open to criticism and discussion without responding with personal attacks, fit (because it’s a leading indicator for other good traits) etc. Also don’t overvalue other traits which though might make the person a useful business connection (wealthy) or a useful sexual partner (hot), might not make them a particularly good investment for a relationship past either making money or getting laid, respectively.

  18. Natural Gas Analyst - Houston says

    This article is eerily spot on. I remember when I used to work in Equity Research a lot of the guys who got promoted to Analysts very quickly at my firm exhibited a ton of the exact traits mentioned above. Moving forward I began to adopt some of these behaviors for my own betterment — primarily those relating to the stoicism book.

    Btw haven’t posted in a while because as you know things have been hectic in the energy space and I’ve switched firms, been swamped with new responsibilities, and switched energy product groups so now I have a whole new (extremely different) market to learn (moved from natty gas –> LNG extremely diff market dynamics).

    Finally, if you guys need someone to do a Wall Street related post in the future — I’m your guy. I can also do something relating to the physical commodities space or Houston lifestyle type posts.

    Cheers! I’ll be attempting to contribute via the comments on a regular basis once again.

      • Natural Gas Analyst - Houston says

        Will do! And thanks, lots of interesting things happening in this market! With disaster comes opportunity.

    • J says

      Would be very interested to hear your opinions on living in Houston; considering relocating there after college

      • Natural Gas Analyst - Houston says

        I will reach out to the playboys soon, waiting for a weekend where I’ll have time to think out and produce a quality piece. Stay tuned!

  19. Anon says

    Hey guys,

    I just want to say thank you for the amazing content you have been given out over the years. I started implementing your advice into my routine on a daily to weekly basis and the it shows on the benchmarks every year again.

    Currently switched from a pointless degree (not necessary pointless, but I didn’t want a *job*, but I finished it anyway to get good marketing skills) to a career path at university. The ROI at the moment looks very good (low cost in education here) and I will probably go into the european Wall Street equivalent to get that cash.

    Been focussing on several skills over the years according to the motto you and Mikael Syding always provoke: always be investing. For example: because I’m in Europe I’ve been studying German to have the possibility to communicate with more clients in the future.
    The same thing with ‘practising’ the *opportunity spotting* – skill to see which markets can be potential business opportunities. Unfortunately, startup costs in my country are very high and as a student you won’t get a loan that quickly. Nevertheless I’ve been saving money and as soon as I reach enough I will pump it straight into a project to get the experience and a potential passive income.

    Summer is coming up, which means as a student enough time to focus on investing. I just bought Mike Cernovich’s book (here on Tuesday) as I’ve seen you guys promoting it several times.

    If I have to pick one tweet of you that would help anyone here it would be the following: “Smart people plan their days by *events* Normal people plan their days by the *clock* Complete the event before moving on. Big difference.” It improved my life by 200%.


    • Miller Time says

      Great reminder on planning days by events. Thanks for that.

      Just a reminder for you my friend, you can totally start a business with whatever money you have now . I think it would do you better to start now with what you have, than to wait months.

      You’re going to learn so much just by starting. Plus I’ll make a guarantee that you’ll change your biz idea or plan several times between starting and 1-3 months in. Especially if this is your first business.

      • Anonymous says

        Hey man,
        Thanks for the advice! I’ve been looking around Belgian law and it looks like you can start very low cost as self-employed instead of a corporation. The tax limit is capped at 50% instead of 33%, but that is a risk i’m willing to take.

  20. says

    Great Post… I’ve got a friend who is a 49 year old Billionaire. amazing how many of these things describe him. You would think he drives a fancy sports car, nope, his every day car is a 2015 Honda Accord. His ego/Self confidence is so high, I’m not sure most people even register in his world. He’s taught me a ton about my business and how the rich handle their money. It was a real eye opener for sure. Thanks for the great blog.

  21. Grant says

    This list is a perfect exposé on the pains of getting along with average people.

    For a very long time I struggled to reconcile my life/poverty with my attitude – It’s never been worth it for me to suck the proverbial dick – for brevity’s sake: to be a consumer.

    A couple years ago I posted a depressing comment on your blog seeking help(shitty family, no prospects). You summarily deleted it. It hurt my feelings. But, I understand why you deleted the comment.

    A few months later we DM’ed, and you advised I take a 40K buy-side job and keep looking – my only offer. I politely told my would-be manager to fuck himself in the last interview, and I graduated without an offer(quant undergrad). That was 13 months ago.

    I’m currently working with a deal team(loose term) under a broker dealer. We structure and sell deals. Private equity up-to the IPO and secondary.

    I’ve been building relationships and learning as I go.

    I’m currently negotiating terms for a small bridge, and simultaneously selling an offering. On private deals I net 6%($+WTS).

    They say you do what your parents do. My parents were in sales. I refused to accept having to sell shit to make money. I felt shame for my ability(and pleasure) to manipulate people. So I pursued science and suppressed my social skills – suffered all the way through a math degree(I do love math, though).

    I think if your blog didn’t exist, I would have stuck my head in the sand and persisted into a quant career. Your formalization of the idea that a salary has an ROI surely crystallized my distaste of subordination.

    The amount of money that can be made on any given day is unlimited. Why on earth would anyone work for a fixed income? I can’t imagine working for a salary.

    I still have a way to go – rebuilding the social skills, plans for business. But my path has been altered for the better because of your blog/tweets.

    Just wanted to say thanks.

    Beyond the money, I appreciate the positive impact of WSPs.

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