The Pursuit of Originality

Life Lessons

  1. Investment: Pay close attention to what billionaires are doing with their money. Elon and Bezos sold right before the bottom fell out
  2. Life: Face difficult conversations and tasks head on and immediately. Otherwise it will fester
  3. Investment: Excellent partnerships are invaluable (Sam Zell)
  4. Investment: A deal with four steps, instead of one, has three additional opportunities to fail
  5. Investment: know the capital asset pricing model
  6. Investment: most investors sell when they need money (at the bottom) and buy when they don’t need money (at the top) which creates absolute returns less than the average market return
  7. General: Take time to think
  8. General: don’t spend any time arguing with people whose ideas you know to be stupid
  9. Investment: interest rates to assets are like gravity to an apple, when one is low, the other can grow uninhibited.
  10. Investment: looking at exact numbers is foolish, looking at a range of numbers is ideal
  11. General: learning is not memorizing, it is changing behavior
  12. Management: don’t tell people how to do things, tell them what to do and let them surprise you with the results
  13. General: act on instincts and have unwavering self belief
  14. Investing: Be patient, have cash so that when the right deal comes you can move fast
  15. Investing: Take profits. When you are doing as good or better than the best average year, take profits and wait for the next opp
  16. Career: Don’t sell anything you wouldn’t buy yourself. Don’t work with anybody you don’t respect and admire. Work with only people you enjoy.
  17. General: Buy clothes that you love in the size you are TODAY
  18. General: the face of the puppet doesn’t matter, it’s all about who has the hand up its ass
  19. Learning: It is ok, and even advisable, to RE-read (RE listen) to important books and media many times
  20. General: If you’re looking for value, look where no one else is looking
  21. Investment: you never lose money by taking a profit
  22. General: always find motivation. Whether it is your own or in others
  23. General: it is the details which make something interesting
  24. General: every hardship is an opportunity. Full Benefit
  25. General: Be the one who imposes the strictest standards on yourself. Only then will you ever be able to expect the same from someone else
  26. General: there is nothing more important than the time you spend with the people you love
  27. Investment: Have money when everybody else is panicking
  28. General: make use of every opportunity to increase your chances for victory
  29. Work: DO NOT take a safe job before you are 30
  30. Money: Debt is fine if you aren’t going to take too big of risks with your life
  31. Money: Never bet against the fed.
  32. Hospitality: 95/5 rule – watch 95% of costs to the penny, and spend the last 5% “irresponsibly” for items that make a big difference
  33. Real Estate: Real Estate is not an end in itself, but a device to bridge gaps between the needs of disparate groups. The greater the number of groups you connect, the greater your profit
  34. Life: never find yourself stuck in a period of time in the past. Always recognize and react to the present
  35. Real Estate: Land can be whatever you want it to be. The only limitation is your imagination
  36. Real Estate: in matters great and small, not logic, but emotions sometimes carefully rationalized to resemble logic, more often than not decide most issues
  37. General: Belief comes before ability
  38. General: All models are wrong, the real work is in figuring out if they are so wrong as to no longer be useful
  39. Investment: one of the best things that my parents could have done is put a mortgage on the house at 2.5% and used the proceeds to invest in treasuries at 5% two years later
  40. Life: The purpose of life is finding out who you really are and living into that
  41. Life: it’s never too late to be who you really are or want to be
  42. Finance: Always take the optimistic side when pitching because no matter what they are going to apply a discount to make themselves feel prudent
  43. Personal: My purpose is to create
  44. General: Try it
  45. Building: make small spaces as nice as possible with materials b/c the absolute cost isn’t that much higher
  46. General: You are better than you think, never never sell yourself cheaply
  47. General & Investment: When you know you have an edge, bet heavily
  48. Investment: Oct 31 is the end of the fiscal year for mutual funds, so they sell into it for tax loss harvesting and other reasons, but can’t hold cash so the reinvest it Nov 1
  49. General: Genius lies in the fewest moving parts
  50. Prediction: focus on the things that are not going to change rather than trying to predict what will
  51. Lifestyle: The most valuable asset you can own is not needing to impress anyone
  52. Deals: time is more advantageous for the buyer than the seller
  53. Motivation: When we are at our best, we are not slogging through. Great people are driven, motivated, and engaged. If slogging is your status quo, then you may be in the wrong area
  54. Progress: Ordinary moments compound over weeks and months into extraordinary results
  55. Life: Stare at the fear. Feel it
  56. Learning: Knowledge can only be gained when we are actively trying to falsify it (scientific method)
  57. Decision Making : You only need to make one or two great decisions per year to have great outcomes. Conversely you need to be set up to make few big mistakes
  58. Investing: One or two fantastic investments can change the course of your financial life forever
  59. Risk: Always gear your life towards being in a position of strength during any market or situation
  60. Risk: With every assumption the likelihood of getting it right is cut in half
  61. Goals: visualize clearly what you want and obsess over moving forward, taking action
  62. Life: We are judged by what we do, not what we think or intend to do
  63. General: Don’t take No for an answer – ever
  64. General: Success is a natural and proportionate result of effort
  65. General: It’s just as much work to tackle big goals as it is small goals, only the consequences will be greater
  66. Investment: Never lose money
  67. Capital Raising: Investors are always looking for good investments, the easier you make it for them the more you will raise
  68. Deals: Come down to a few key points. If you can figure these out, then you will be an effective negotiator
  69. Investing: know how to spot peaks
  70. Investing: Only invest in a previous asset bubble when investments are 10% above previous lows, otherwise they may languish at the bottom (Schwarzman, Houston office 1980-1990)
  71. Politics: Several small but persistent and loud voices can shape the world
  72. Goals: Big goals are just as difficult as small goals, so always aim big because the rewards are out of proportion
  73. Career: Executives are made not born, and are constant learners
  74. General: Always write or call the people you admire and call or ask for a meeting you never know who will respond
  75. Networking: There is nothing more interesting to people than their own problems. Try to come up with ideas to help them
  76. Career: Information is the most important aspect of business, the more you know the more you can spot patterns and ideas
  77. Career: take hard jobs with steep learning curves and good training when you are young
  78. General: first impressions matter
  79. Investment: Never lose money, make sure the principal is always protected
  80. General: Don’t be afraid to ask for what you want
  81. General: if you see a huge transformative opportunity don’t be worried if nobody else is pursuing it
  82. Deal making: time wounds all deals
  83. Leadership: make decisions when you are ready, not on someone else’s schedule
  84. General: learn from all failures
  85. Business: hire 10s all you can
  86. General: Be there for the people you know to be good
  87. General: do what you can to help others achieve their dreams
  88. Investment: Liquidity at the right time can make a investment great, whether buying at the bottom or selling at the top
  89. Political: When the economy is going bad, people look to the government to bail them out and they are willing to give up a lot of freedoms
  90. Trends: Places change – to really understand what is going on you need to see the video not the snapshot
  91. Investment: Leasing to just one group/person puts a high level of concentration risk on an asset
  92. Cleanliness: The state of your space is the state of your mind
  93. Education: Grades are the score in the game of school
  94. Money: Money is the score in the game of business
  95. Money: Be long-term greedy don’t take $.25 today when you can take .$10 a year for the next 30
  96. Death: In the end we have nothing but the memories in our minds and the people surrounding us
  97. Communication: Learn to speak with anybody – over all types of modes, and many more opportunities will be unlocked with the older generation
  98. General: You don’t need to share the same dreams as others, even those you admire and respect
  99. General: Men will do nothing if they don’t have to, but once they have to, they can do anything
  100. Learning: Always write for yourself
  101. Investment: Just stay in the game
  102. Investment: Better to be positioned well vs being right
  103. Investment: Lessons to avoid – 1. Group decisions 2. Desire to conform to others 3. Asymmetry to risk and reward 4. Overdiversification 5. Inertia
  104. General: The world is for askers
  105. General: Build wisdom and then trust yourself
  106. General: Environment determines behavior. (Including people)
  107. General: The best way to form habits is to make rules rather than leave each opportunity up to decision.
  108. General: Never be afraid of the truth
  109. Development: Always go out with maximal plans knowing the optimal will be easier to get approved
  110. Bubbles: Modern bubbles can always be tied back to an inappropriate amount of central bank spending
  111. Career: Start as an assistant or shadow to a very powerful senior person and learn the endgame first
  112. Investing : avoid single points of failure by identifying them and mitigatibg them
  113. Investing: make bets that allow you to stay in the game long enough to take advantage of tough times or infrequent opportunities
  114. General: the past doesn’t predict the future, however the more recent past is a better predictor of outcomes than the long term. Think: Benjamin grams intelligent investor doesn’t work on todays enviornment
  115. General: Have no sunk costs
  116. General: the least productive hours are 9-12 at night, the most productive are the AM
  117. Investing: Avoid total loss. The bigger the edge the larger the bet. The smaller the risk the larger the bet
  118. Investment: Money making is not a constant, but happens in inconsistent and often unpredictable windfalls throughout life. Keep open to these windfalls
  119. Career: If you want to leverage your success so that you don’t need to work for long, choose a career that provides immense scale (trader, investor, writer, IE anything not paid by the hour that requires you show up and do the work over each time) This can be more risky however, because riches aren’t equally distributed)
  120. Randomness: Randomness is just un-knowledge
  121. Education: Grades are important because of cumulative advantage – whe n success starts early, it is easier to get success later
  122. Silver Rule: Do not do to others what you would not like done to you. IE mind your own business
  123. Public Speaking: spotlights reduce concentration so speak without a spotlight
  124. General: laws come and go, ethics stay
  125. General: domesticated animals animals have no chance of survival against their wild counterparts
  126. General: The wisdom of crowds is better for a judgement than an opinion
  127. General: First to speak exerts the most influence, especially among weak opinions or subordinates
  128. General: Understand you live in a bubble, understand that most people don’t think the way you do and don’t experience life the way you do.
  129. General: When the music stops the claws come out – always be above board
  130. Knowledge: knowledge can only be falsified, never confirmed
  131. Statistics/Probability: When N=1 the machinery of probability theory fails. Some win the lottery, some experience unbelievable tragedy multiple times in life. Sometimes both can be true for the same person
  132. General: Never buy cheap paint
  133. Real Estate Cycles: Commercial cycles can be significantly slower than housing. Ex: 1980s office market crash lasted 18 years from peak 1981 to trough 1991, back to normalizing by late 90s
  134. General: Open your best wines on your worst days
  135. General: Embrace the discomfort and learn what you are made of through it
  136. General: you can learn or memorize anything, you just have to know the right techniques
  137. Life Experience: you go there to know there
  138. General: Everything is going to be OK
  139. General: the most important thing in life are relationships
  140. General: collecting more information and putting forth more effort is always a competitive advantage
  141. General: Strive to have clear vision
  142. Starting Business: You can never over-pay the best talent
  143. Starting Business: Identify the big trend and invest in technology supporting that trend
  144. General: Problems are opportunities in disguise
  145. General: Don’t hide your eccentricities, embrace them
  146. General: There are no perfect human beings
  147. General: Relationships run the world and reputation is everything
  148. General: See the world for what it is, not what you wish it to be
  149. General: Creating an original place means deliberately destorying things that work in order to embrace the possible
  150. Human Nature: People don’t want to BE informed, they want to FEEL informed
  151. Investing: Market cycles matter A LOT
  152. Investment: What will be the same or different 12 months from now
  153. General: Opportunity handled well leads to more opportunitiy
  154. Business: Stay in the game long enough to get lucky
  155. Investment: It’s easier to get to the 1st Million by working than it is to invest your way there with no money to begin
  156. Career: there is nothing wrong with spending the 1st part of your career in a big company – they pay you to learn. Even better if you’re in a high paying industry like finance
  157. Fashion: Dress purposefully. Everything you wear should have a reason
  158. Fashion: 50% of your look is your shoes. Can dress up or down your outfit
  159. Ideas: an good idea “spotter” will always be more successful than a good idea created because the world comes up with infinitely more good ideas than an individual can
  160. Ideas: stories stick, stats & poise don’t
  161. Stories: Don’t bury the lead. Make your ideas stick
  162. Exercise: Always do full range of motion weightlifting
  163. People: The best way to get what you want is to get people what they want
  164. Work: It’s not about how many hours you put in, it’s about what you get done while you’re working
  165. General: It’s more important to know how to get information than to hold information in your head
  166. Communication: Pauses are sometimes the best tool in communication
  167. Communication: What you say is who you are in others eyes
  168. Communication: Learn how to say “no” respectfully, definitively, and confidently
  169. Communication: Things you say to anybody and everybody have unknowable impacts on others, so make sure you say everything with purpose and intention
  170. Success: to be successful you have to put yourself in situations and places you have no right being in. You shake your head and learn from your own stupidity. But through sheer will you wear down the world and it gives you what you want.
  171. Time: it’s never too late to start something new. You have more time than you think
  172. Career: It is one of the best positions you can put yourself in to be the “boy” (the assistant) to the billionaire after college. Just the assistant for a couple years after which you may have access to their resources. These are the people that fly on the PJ but can’t afford to fly biz class
  173. Career: All that matters in a job is if the Principal likes you. People who do good work get fired, People who do good work and are liked don’t.
  174. Success: Have an audience. It is underpriced and will pay off immensely in proportion to the work
  175. Success: Listening to podcasts, consuming info, and doing research may feel like action, but until you really start building it is also a trap to make you feel like you’re taking action when you are not
  176. Confidence: Always reframe any “Why me?” to “Why not me?”
  177. Success: the only thing standing between you and what you desire is your limiting beliefs. Squash those and you will get whatever you want
  178. Success: you need three things to have success in making changes in your life: 1. Conviction 2. Incredibly High Standards 3. Excellent Strategy
  179. Change: Change is never a matter of ability – is always a matter of motivation
  180. Success: Ask yourself, what could I be #1 in the world at? Pursue that for extreme growth
  181. Goals: The competition for the average is highest and hardest, whereas the competition for the exceptional is non-linear, less crowded, and often easier
  182. Success: You set your own value in the market, so don’t set it too low

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About the author

Sophia Bennett is an art historian and freelance writer with a passion for exploring the intersections between nature, symbolism, and artistic expression. With a background in Renaissance and modern art, Sophia enjoys uncovering the hidden meanings behind iconic works and sharing her insights with art lovers of all levels. When she’s not visiting museums or researching the latest trends in contemporary art, you can find her hiking in the countryside, always chasing the next rainbow.