How to Win.

Everyone needs to develop the correct mindset for growth. Every day in life you will run into people with negative mindsets and bad advice, this is going to create a negative feedback loop and you want to avoid these people at all costs. We are going to break your mindset up into digestible chunks. Below is a quick list to keep in your back pocket.

A successful man will take the following actions:

  1. Avoid every human being who complains about things beyond his or her control
  2. Seek out mentors who give opinions based on real life experience
  3. Avoid all men with a pessimistic economic outlook on life
  4. Surround yourself with men who have succeeded in your field of choice
  5. Drop stagnating peers within your social circle
  6. Seek out young up and comers that you believe in

For a trained reader the first bullet is a trap followed by an actionable second bullet to prevent falling into it.


Avoiding Complainers

“Does anyone know a happy and successful person who complains all day?”

Lets agree here, everyone has problems. Maybe the problems for your neighbor are lighter than the problems you face today but this does not change the fact that your neighbor still struggles with day to day issues of some sort. If we can simply agree that everyone has an issue they are trying to solve then we can take the first step in avoiding a complaint in the first place. This point is best served in examples:

Example 1 Race: In the USA this is a heated topic and will be for the foreseeable future. We have stereotypes. Yes this is not fair. We have people from all walks of life African Americans, Indian Americans, European Americans… etc and each ethnicity is going to be stereotyped in some way. Nothing can be done.

While we can sit around the bar and state that it is unfair that Asians are stereotyped as being good at math and African Americans are stereotyped as being violent, talking about the subject is not going to change your life one bit today. Instead address each issue and do what you can to control it. If you are perceived as dangerous, become well groomed and well dressed. If you are perceived as shy and intelligent, let them assume you are intelligent and focus your energy on improving your salesmanship. Solve the problem.

Example 2 Technology: One major change that will never go away is innovation. Capitalism is a system built to solve problems as fast as possible and allow the inventor to prosper from the solution. Are people glued to their smart phones? Yes. Can you prevent men and women from purchasing smartphones? No.

Instead of analyzing the situation and how this is bad for you on a personal basis you should immediately ask how you can use it to benefit your life. It is easy to find the negative to a situation and significantly harder to find the solution to the situation. Maybe social skills will decline over the coming decades, or maybe you can create an application for the smartphone that will add value to the user. We will wager that if you can do the latter you’ll be much happier than complaining about the former.

Example 3 Culture: You have a belief system, so does your neighbor. While you may agree with us and hate the explosion of tattoos, skrillex haircuts, flip flops, kangaroo courts and general entitlement… again only attack issues that can be controlled. You cannot prevent a person from obtaining a tattoo and you cannot prevent someone from shaving their head.

What can you do? You can befriend thousands of people and gain their respect. Now if they ask your opinion on attractiveness they are much more likely to take you seriously. This is not going to change a country over night, but it is going to change your personal environment which you are responsible for.

With the examples out of the way, this begs the question on what is a complaint and what is asking for advice? The difference is simple, a complaint has no actions and advice is followed by action. Lets take it a step further, and create a simple definition. If you have not taken direct steps to improve your situation, you are complaining. If you have taken multiple steps but have gotten no where, you’re asking for advice.

The best example of inaction versus action can be found in the weight loss industry. The weight loss industry attempts to sell you a special formula that will allow you to lose weight without changing your lifestyle. For anyone with a shred of knowledge regarding diet this is a terrible decision. Instead you should attack the problem yourself and find guidance from those that have succeeded.

Person 1 (Complainer): I am overweight please help me lose it right now.

Person 2 (Needs Advice): I lost 20lbs the last 2 years but want to lose 10-15lbs more. I have tried but can’t seem to lose any more weight here is my diet/exercise routine can you help me lose weight?

If you meet people in camp number one, do not reach out to them and do not spend your time trying to bring a horse to water that will not drink. If the person you are speaking to is in camp number two, well you have a new friend standing in front of you.


Seeking Out Mentors

“A problem with freedom of speech… Everyone has an opinion they deem valid.”

With that back drop, once you’ve developed a positive action taking personality it is best to maximize your results by applying correct information.  This is a key step to success. Accurate information is expensive, rare and difficult to find. In an ideal situation your life will constantly look like this:

Objective à Personal Attempt à Improvement à Personal Attempt à Failure à Guidance

You have an objective in mind and do your own basic research to get there. After personal attempts and failures you improve. Then the pain comes. You hit a road block for several months and can’t seem to jump the gap. Now it is time to seek out guidance.

Finding the Correct Mentor: Your ideal mentor will have the following qualities: 1) older than you, 2) more years of experience in the task, 3) worse environment relative to you, 4) willingness to help and 5) passion for the topic. Generally speaking, if a person is unwilling to help it means they do not believe in you or they lack a willingness to help, you can try to control the former but nothing can be done with regard to the latter. In addition, successful people have an addiction to giving back in some way because they typically have a passion for the topic. There are rare exceptions to this rule which is why we have made it a 5th point, however to achieve excellence in anything requires a baseline of passion. With the backdrop out of the way here is your step by step.

  1. Find your exact field and shoot for men/women in the exact same field 10+ years older than you are today, located within a few miles of your current home
  2. Read the biographies of the individuals if possible, gather baseline information about their history and find an individual who had less assets to work with than you currently have access to
  3. Cold email, cold call and do anything to get in touch with these individuals, you should pick up at least one, here is a basic template:

“Hi my name is XXX I am interested in learning about XXX. I have achieved my goals of XX and XX but am having trouble with YY. I would love to have a few moments of your time to discuss YY and would be happy to adjust to your busy schedule”

The goal is to keep your pitch short and sweet: 1) you tell them what you want to learn, 2) what you have done already to try and achieve your goals and 3) you make it clear that their time is more valuable than yours and you won’t waste it.

  1. After reaching out to several men and women you will likely find 20-30 minutes of time to chat with an expert or possible mentor in the field. Be sure to prepare questions and examples of your struggles that prove you have attempted to grow
  2. Once you obtain as much information from your new possible mentor, go and put the advice to action. Leave the phone at home and execute on the advice
  3. Assuming the advice was valid and helpful you will see results, now you can update your mentor with progress. The chances of this person helping you in the future is now sky high as you have validated his opinions and you have delivered results.

“Hi [name] I just wanted to write in to say thank you for XX and XX after heeding your advice I accomplished XXX. Without your input this would have never happened” (Ideally you attach proof of your accomplishments as well)

We know what you’re thinking, what if the person does not want to help me? Well you can take a guess at the answer… Keep searching. Most people who are successful in life take great joy and pride in helping younger up and comers succeed so it is only a matter of time before you find one person willing to spend a few minutes of his or her time with your development. As mentioned above, it bears repeating, do not waste any of their time.


Avoiding Pessimistic People

“If you hope the world ends, your world has already crumbled.”

You would think that complainers and pessimistic people are the same. Unfortunately, these people are crafty beyond belief so we should take the time to make sure they are neither complainers nor pessimistic. The incessant complainer is easy to capture since he/she cannot help but constantly bring down the atmosphere in the room. The pessimistic person is much more crafty, he/she is a self-proclaimed “realist”. The only thing *real* about this persons view is that it is a view from his or her current state of life.

Knowing that a pessimistic person will have a silver tongue that will convince you of his/her viewpoint it is best to flesh out these people with a three simple direct questions.

What have you done to fix X?

Have you ever tried to contact person Y to address your issue?

What makes you believe this is true for all people?

Usually a pessimistic person or *realist* is only speaking from a vantage point from his own life and has not made the effort to contact or mingle with those that have already overcome his/her issue. You’ll notice that this is a theme, they have relied solely on their own reality and refuse to step into the shoes of another man or woman. They have a rigid and unchanging belief system. Don’t fall into the trap.

Continuing with this theme, you can take your contact list and quickly find the pessimistic people who have infiltrated your contact list. This simple trick is going to make your life easier. When you scroll through their name in your phone ask yourself the following question.

“Would people be happy if I brought this person to a party”

How easy is that? Would people be happier around this person and you’ve already broken the code. No one, literally no one, wants to be around a pessimistic person. Even when you’re down and out, depressed and feel like the world is on your shoulders the last person you want to hang out with is the pessimistic man/woman. People can’t help but want to be around the happy go lucky guy because it temporarily eases their mental pain. As much as we like to believe misery loves company, even miserable pessimistic people will choose to be around someone who makes them feel good. A simple benchmark indeed.


Create a Positive Surrounding

“Instead of allowing your environment to control you, build it yourself.”

This section is a slight divergence from finding your mentor. At this point you should have a small handful of positive mentors in your life and you should already be well on your way into becoming an expert in a field you are interested in. This means you need to simply throw yourself into the deep end of the pool. The difference between your environment and your mentor is that your environment will always contain negative people (unavoidable) and will always contain a few people you dislike (unavoidable).

Unlike the previous points made this is a larger picture point, we’ve already established that you will have a contact list that has zero complainers, zero negative people and a handful of people you aspire to be, now it is time to hold yourself to a higher standard. The personal adjustments have been made, now you must enter a world where you are at the bottom of the totem pole or close to it. This is the only way you’re going to improve and cross paths with new mentors and friends. You’re not going to make strides in an environment full of average men and women. Raise the bar.

The best way to raise the bar is as follows 1) niche groups, 2) competitive environment and 3) age discrepancy.

Niche Groups: Niche groups can range from an investment club at your university, to Toastmasters, to a meetup group for learning a foreign language to a sports group. No matter what the niche group is make sure you are not the teacher and you are not the best in the room. The entire point of joining a niche group is to learn from someone who is better than you, by default you will improve if you continue to play catch up in the environment.

Competitive Environment: Wall Street is competitive enough as it is. If you’re in this camp you’re already well ahead since you’re competing with the top 10% of the top 10% of universities in America. Beyond Wall Street you can still find ways to place yourself in a highly competitive atmosphere. If you’re interested in dating attractive women you try to compete at expensive bars and lounges. If you’re interested in becoming an amazing software engineer, take the job at Google instead of the job at the no-name tech company (exceptions for the incredibly brilliant who create their own companies). Last but not least, if you wish to improve your salesmanship, go into high-end sales. Much more risk and much more rewards come from selling a product worth $1,000 versus $50. If you fail in the environment, the fall from graces will be softer as you’ll be ahead of your peers who chose the path of least resistance.

Age Discrepancy: Better to be the youngest in a group of lions than to be equals with a handful of cats. The best way to put distance between you and your peers is to keep pace with those that are wiser, more experienced and more accomplished than you. The person sitting next to you can quickly fast track his career by hanging out with gentlemen 5+ years older than himself. Don’t let him beat you to it.

The big blocks are now put up. You have a handful of contacts who will help you, sparingly as their time is expensive and you are spending the vast majority of your time in an environment where you are one of the weakest links. There is no where to go but up if you continue to put in the work at this time.


Cutting the Cord

“You can lead a horse to water but you cannot force it to drink”

This piece should cut deep for many readers. Your phone is already free and clear, your environment is in great shape, yet some people are not on the same page as you and are quickly falling behind. It may be time to close the chapter. If your positive friend is nodding at all of the changes you’ve made he or she is going to have to take action or fall off the wayside.

This is not a pleasant experience.

You should go through this experience on a personal basis and from a friendship basis several times through your late teens to late twenties. You will drop hobbies and activities that were once fruitful and you will slowly fade away from friends who were a net positive on your life and are now living a life of stagnation. One of the worst feelings in the world. Losing a close friend.

The silver lining and good news in this case is when you decide to fade away from an activity or friend that was once adding value to your life is that you can remain in soft touch contact with the person on a monthly basis. Similar to your mentors, you are now a guiding light for those that were once on the same path as you.

From a personal basis, we all know the rock star athlete, musician or artist who simply could not realize he or she has reached their potential and should move on. This can easily happen to you as well. While it is always great to have ambitions and shoot for the stars there is a major difference between a realistic goal and a dream. By keeping your head on your shoulders you should avoid all of these traps.

Lets take a look at a few:

Division 1 Athlete: Maybe you made it to a solid Division one school on a baseball scholarship. Unless that school consistently places athletes into the MLB… It is probably not going to pay the bills any time soon. Instead of hanging on to a lofty dream you should spend your time leveraging the free education you have received and focus on building on your next step, a career, while having athletics rank as your second most important task. You do not want to be in your mid twenties reminiscing about your past achievements.

The Artist/Musician: Maybe you or a close friend has always had a knack for art/music… however… similar to your athletic friend they were great but not good enough to obtain admission into the Juilliard School (replace Juilliard with name brand art schools). Again, similar to the athlete music and art lovers will be better off in the long-term curbing a hobby they are good at for an intelligently chosen career. There is no need to drop a hobby/skill you are good at, it can act as a secondary source of income, but living outside of reality can ruin your future.

A Best Friend: Similar to your own reflections, in life you are going to be forced to make the same judgment calls with regards to your close friends. Even if you have known him/her for 5+ years, if your ambitions, goals and work ethic all change simultaneously there is no other choice but to move on. A small percentage of people, likely less than 5% of people you will meet, will have the right attitude and mindset to continue improving.

Once you have made a few painful decisions in life, removing close friends or dropping activities that were once fruitful, you will be well positioned for the future. With your life nearing full throttle you can move on to the final step of recruiting younger men/women to join your path.


Paying Information Back

“No need to be afraid, the masses will never take action”

As you approach your late twenties you should be firing on all cylinders: 1) strong social circle, 2) a high income, 3) physically at the prime of your life and 4) no complaints about your dating life. If you have everything you want, you don’t spend your time hoping the world ends, instead you wonder if you can help someone else obtain success

One of the best feelings in the world is when you are able to find someone who is several years younger than you, pass them advice and watch it turn into another success story. The tricky part? You’ll find that 99/100 people would rather insult you, denigrate you and ignore anything you have to say. This is exactly why you should not be concerned about your secrets being revealed… The vast majority believe they already know everything, based on zero actual experience of course.

With the backdrop out of the way how can you quickly find young people to help? The answer is always the same, by searching for a similar belief system. Success will always breed success, by searching for a similar thought process communication is easier and results are achieved at a much faster pace.

Alma Mater: A good place to start is always college. If you went to a similar university or a school in the same prestige ball park, you will likely have a lot in common from the jump. Ideally, they have not fallen into the trap of believing everything they are taught and if they are like you, they will have their reservations. With that said if an email hits your inbox with a similar school it would be wise to respond for the sole purpose of giving back helpful information.

The Gym: Replace the gym with tennis court or golf course (there is a reason a lot of networking occurs on the golf course). When you are asked for your opinion on the topic, assuming your skills are above the average in the group, happily hand over all of your advice. If you can help someone improve physically they will likely listen to your advice in other areas in life. In addition, they may have something to teach you as well.

The Workforce: As mentioned before on the blog and elsewhere, your co-workers are not your friends. This is why you should stick to the “two rung rule”. What this means is if you are going to train and help an employee within the same firm you should be certain that they are two levels or more below you on the ladder. If they work directly beneath you and they are promoted… you are back to the cutthroat atmosphere you had before. Better to stick with employees that are a good 5-7 years behind you on the career trajectory to avoid perverse incentives. With that in mind, if an entry level employee with the right mindset and capabilities is looking for guidance you should jump at the opportunity.


Concluding Remarks

“The only way out is by moving forward”

You now have a detailed look at how your mind should operate. However… If you’re able to implement all of the ideas outlined above your life will likely improve. In the coming months as you get rid of wasting assets (poor friends and negative feedback loops) and spend your time focusing on what you can control (health, career choices and your contact list) things will “magically fall into place” as they say.


  1. Jake says

    Wow this is probably one of the longest posts you guys have put out, looks like it was written for an up and comer.

    Can’t agree more with most of these.

    • Wall Street Playboys says

      The general purpose of this post is to provide a summary for how to fix your life. If this doesn’t make sense then there are deep rooted problems in their life that needs to be sorted out.

      Life in general is very tough. It is even tougher to figure out who is helping you and who is wasting your time. That is why the framework is around how to choose between the haves and have nots.

  2. TP says

    Great post. Going to read through this a couple more times to digest it.

    What do you find the main difference is between someone who is straight complaining, and someone who is extremely down (initially) after a significant failure/rejection?

    In addition, how do you handle the latter in the very early stages after the failure?

    • Wall Street Playboys says

      You should read the post titled “I’m a failure”

      A complainer won’t find solutions they will incessantly annoy you with the same comments to death. Just ignore them.

      Everyone goes through ups and downs but once you see it is a character flaw eject eject eject.

      If you don’t like failure or have never failed, then you’ve accomplished literally nothing in your life. Once that is really engrained in your mind, you’ll enjoy the failure process.

  3. simpflm says

    At 28 years old I wished that I had learned the importance of cutting the chord sooner. I didn’t realize how insidious yet potent the effect of negative/stagnant family and friends and SO’s can be. Not only because they themselves are negative, but because the negativity distracts you from finding positivity.

    I was a deeply negative and cynical person in my mid 20s, I could have done a lot more if I had the positive, abundance mentality that I try my best to have now every day.

    Friends still whining about a ten dollar cover charge or ATM frees, angry baby boomer relatives whining about congress, people who scoff at my goals of making my online business succeed… who needs them? I had to say goodbye to a best friendship this year. He still lives at home, is currently jobless, and plays WoW. It still was very hard. Some of my best life memories involve him. He’s a great guy and I’ll never “ice” him, but there’s no precious time to be wasted on this earth associating with people who don’t take full responsibility for making their time on our planet the best possible experience.

    • Wall Street Playboys says

      If you can’t think of a single thing being added besides “good memories and funny guy” then there is generally a problem.

      No need to ice, if you run into them (unlikely) smile and be happy but don’t respond to any invites in the future. Your time should be too expensive, as you earn more you’ll find your friends will change faster and faster.

  4. Broski says

    Spotted one tiny issue: “do not spend your time trying to bring a horse to water that will not drink.” Just letting you know in case you didn’t catch it.

    Other than that, very solid post! (as per usual)

    • Wall Street Playboys says

      Probably poor reading on our end but do not understand your comment?

      “do not spend your time trying to bring a horse to water that will not drink.”

      Complainers and people who don’t try ti improve by themselves are all horses that will never drink the water. So don’t waste your time trying to show them the ropes, they are dead weight. Cut your losses.

  5. East Coast Month 2 says

    Tremendous post as always.

    I have read through “A Guide to Rational Living” and “No More Mr. Nice Guy” recently and am really beginning to internalize a few of the concepts (mental). I have moved from a small town, where I was emotionally and financial co-dependent on family and friends, to Washington DC for work (leaving comfort zone, no contacts). I’m consuming a protein rich diet: eggs, whey, salmon, chicken, and nuts, under 20 carbs (nutrition) and exercise often (2 days Muay Thai, 3 days Lifting).

    I realize I am making progress, but it can be difficult to go through each day without tending toward pessimism and complaints, as this is what I’ve been about and exposed to the majority of my life.

    Wondering if you guys have any solid advice for working on not complaining and not being pessimistic throughout the day? I’m the “not fun to be around” guy and am a bit sick of not being able to break through.

    Blog changed my life, hope I am not too old for it all (30).

    • Wall Street Playboys says

      To be honest it sounds like you’re doing everything right.

      There is no “light switch” there never is.

      Continue down the path and you’ll complain slightly less and less. There is no such thing as perfection so you’re going to have bad days here and there but over an annual basis you should notice improvements. That is why we draw the line at a full year comparison. Take yourself and your friends and ask “is this person noticeably better than he was before” if so then you’re doing it right.

      It sounds like you’re doing it right.

      Finally, you don’t need to become a stand up comedian. In fact, average people probably hate people like us. So you can revise that to “the right people should enjoy your company”.

      If the person who dislikes you is a nobody (no financial improvement, no physical improvement, tries to hate on you) well clearly people like that shouldnt enjoy your company. Neither should you.

  6. Al says


    Thanks for sharing great advice- spot on.
    Hang with the winners and you’ll become one

    You guys planning to start a store and sell some WSP gear?


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