100 Things That I Think Are True

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75 Things That I Think Are True In The Trenches

Like many of you, I’m a sucker for a good quote.

The best quotes often distill a lifetime of wisdom into only a few words, which is likely why some of them continue to resonate for decades (and in some instances, even centuries) after first being articulated.

Over the years, I’ve compiled quotes from countless books, mentors, podcasts, and blogs, and in each instance the quote represents an idea that I believe to be fundamentally true. Below, I present this collection of quotes to you, in hopes that some of them impact you as much as they’ve impacted me. Most importantly though, I’m proud to finally be able to tell my wife that all of those years of highlighting books in bed have finally led to a tangible piece of output.

To the extent that you enjoy the format below, know that I deserve none of the credit: My inspiration for publishing this blog post came after listening to a recent episode of the Morgan Housel Podcast, during which he presented his listeners with a collection of quotes that were particularly meaningful to him. So, any credit for what you enjoy can go to him, and any blame for what you do not enjoy can be directed squarely towards me.

I’ve done my best to attribute each quote to its original source, but it I’m sure that I’ve made many errors and omissions in the process.

Nonetheless: Happy reading.


  1. “To the man with only a hammer, every problem looks pretty much like a nail” (Charlie Munger)

  2. The biggest myth about entrepreneurs is that they’re born risk takers. Entrepreneurs aren’t risk takers, they’re risk mitigators. Indeed, they often decide to pursue an entrepreneurial endeavor because they see opportunity for an outsized reward relative to the risk that they’re taking in pursuit of that reward (the first part of this quote is attributable to Jim Sharpe)

  3. If you can’t explain a given topic to your grandmother, chances are you don’t truly understand the topic yourself    

  4. A problem well stated is a problem half solved
  5. When making major decisions, be a fast “no”, and a slow “yes” (not a direct quote, but idea was taken from actor Matthew Mcconaughey)

  6. It’s amazing what a group of people can accomplish when nobody cares who gets the credit
  7. Imposter Syndrome is often just a byproduct of ambition. Instead of resisting it, embrace it as a sign that you’re pushing towards your highest and best self
  8. If you treat people like adults, they’ll generally tend to act like adults. If you treat people like children, they’ll generally tend to act like children
  9. “Read last year’s forecasts before you take next year’s too seriously” (Morgan Housel)
  10. “Every successful business is a loosely functioning disaster” (Brent Beshore)
  11. If every conference, panel, or CEO round-table forced all of their attendees to drink a truth serum immediately before the event started, the likely result is most attendees would leave the event feeling comforted and supported, not inferior and self-conscious
  12. The sum of the hours that you spend working is not a proxy for your levels of commitment or ambition

  13. “You’re not going to get rich renting out your time. You must own equity – a piece of a business – to gain your financial freedom” (Naval Ravikant)

  14. If you regularly have the “Sunday scaries”, you’re in the wrong line of work

  15.  “Every job looks easy when you’re not the one doing it” (Jeff Immelt, former CEO of General Electric)

  16. We often arrive at home at the end of the day in a tired and emotionally depleted state. The patience, thoughtfulness, and engagement that we strived to achieve at work often doesn’t seem to follow us home. In this way, the people who are most important to us regularly get the worst of us  
  17. “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at best knows in the end the triumph of high achievement, and who at worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” (Theodore Roosevelt)

  18. “The world is too complex for 100% of your actions to dictate 100% of your outcomes” (Morgan Housel)

  19. The ability to quickly identify and rectify bad hires is arguably as important as the ability to make good ones
  20. Regret almost never results from trying and failing. Instead, it often results from never having tried at all
  21. Big lessons sometimes require big tuition payments
  22. Organize your time according to this simple framework 1) Things I have to do; 2) Things I want to do; & 3) Things other people want me to do. Simply being aware of this is likely to minimize the amount of time that you spend in category #3 (framework adopted from Shane Parrish)

  23. “The main thing is to keep the main thing the main thing” (Steven Covey)

  24.  “Life, in part, is like a poker game, wherein you have to learn to quit sometimes when holding a much-loved hand — you must learn to handle ( . . . ) new facts that change the odds.“ (Charlie Munger)

  25. A CEO’s strategy is only as good as her ability to communicate it
  26. “A company’s culture is a macrocosm of the CEO’s psychology” (David Sacks)

  27. Not everything that is important needs to be quantified, and not everything that can be quantified is important

  28. The biggest temptation of a software CEO is to throw bodies (specifically engineers) at problems

  29. Nobody knows what it’s like to be an Entrepreneur or CEO unless you’ve been one
  30.  “Winning has a price. Leadership has a price” (Michael Jordan)

  31. A CEO’s ability to manage her own psychology is at least as important as, if not more important than, her ability to manage her business
  32.  “You think buying a business is hard? Try running one. You think running a business is hard? Try selling one” (Badge Stone, of WSC & Company)

  33. Setting too many goals is one of the primary reasons why most companies find themselves achieving none of them

  34. “Work expands so as to fill the time available for its completion” (C. Northcote Parkinson)

  35. We over-estimate what we can accomplish in a day, and under-estimate what we can accomplish in a year

  36. You can make excel say anything that you want it to say 

  37. In certain circumstances, jobs, or stages of one’s career, there likely are high returns to playing the “brute force” game (a singular focus characterized by unsustainably high levels of imbalance, hours worked and/or sacrifices made). There are, however, an equal number of circumstances, jobs, and stages of one’s career where there are not only diminishing marginal returns to brute force, but in many instances the correlation might actually be negative. In instances like these, a “clarity of thought” game is being played. Most problems are experienced when: a) One doesn’t recognize which of the two games they’re currently playing; or b) One takes advice from (or compares themselves to) somebody who is playing a fundamentally different game from them

  38. Every boxer has a plan until he gets punched in the face (Mike Tyson)

  39. There’s no such thing as “no”, just “no for now” (Jim Sharpe)

  40. Turn “what” problems into “who” problems (Jim Collins) (for example: Instead of asking what you should do to solve a problem, ask instead who should solve it, or who has solved a similar problem in the past)

  41. Either change the people, or change the people

  42. The use of Debt when financing an acquisition is like the use of salt in cooking: If you don’t add enough, it’s really easy to fix. If you add too much, it’s really hard to fix

  43. “Running a business is learning to go to sleep at night with unresolved issues” (Paul Orfalea, founder of Kinko’s)

  44. “The only way to learn how to be a CEO is to be a CEO” (Ben Horowitz)

  45. How you do one thing is how you do everything

  46. If you have to make a list of pros and cons, then the answer is “no”

  47. You’re killed by the bad deals that you do, not the good deals that you don’t do (Jeremy Giffon, paraphrased)

  48. Fear of failure tends to be highest among those who have never really failed at anything

  49. The loudest boos usually come from the cheapest seats

  50. “Every battle is won before it is ever fought” (Sun Tzu)

  51. “There are two types of successful people: Those with imposter syndrome, and sociopaths” (Morgan Housel)



  1. “Enlightenment is the space between your thoughts” (Eckhart Tolle)

  2. “Your superpower very often sits right beside your biggest wound” (Tim Ferriss)    
  3. When the student is ready, the teacher appears

  4. The root of most interpersonal problems can be traced to the difference between agreements and expectations    

  5. Life is what happens to you when you’re busy making other plans        

  6. Insecurity is loud, confidence is quiet.    

  7. Vulnerability is often one of the traits that we most appreciate when its being demonstrated by others, yet it’s the trait that we least often demonstrate when we deal with others ourselves           

  8. No virtue is free

  9. Everything has a price

  10. Happiness = Reality minus expectations 

  11. The days are long and the years are short
  12.  “If your best friend were to ask how she could live a better life, you would probably find many useful things to say, and yet you might not live that way yourself. On one level, wisdom is nothing more profound than an ability to follow one’s own advice” (Sam Harris)

  13. “Develop a taste for having problems. Behind our urge to race through every obstacle or challenge, in an effort to get it “dealt with”, there’s usually the unspoken fantasy that you might one day finally reach the state of having no problems whatsoever. As a result, most of us treat the problems that we encounter as doubly problematic: first because of whatever specific problem we’re facing; and second because we seem to believe, if only subconsciously, that we shouldn’t have problems at all. Yet the state of having no problems is obviously never going to arrive. And more to the point, you wouldn’t want it to, because a life devoid of all problems would contain nothing worth doing, and would therefore be meaningless. Because what is a “problem”, really? The most generic definition is simply that it’s something that demands you address yourself to it – and if life contained no such demands, there’d be no point in anything. Once you give up on the unattainable goal of eradicating all your problems, it becomes possible to develop an appreciation for the fact that life just IS a process of engaging with problem after problem, giving each one the time that it requires – that the presence of problems in your life, in other words, isn’t an impediment to a meaningful existence but they very substance of one.” (Oliver Burkeman)

  14. You don’t usually burn bridges by what you do. You often burn them by how you do it
  15. Some lessons have to be experienced before they can be understood
  16. It’s amazing how much more critical we are of ourselves than we would be of a loved one in an identical situation. If it’s so logical and intuitive to treat others with empathy and understanding, why isn’t it equally logical and intuitive to treat ourselves in this same way?  
  17. How much better would the world be if we all simply followed the very same advice that we regularly give to our own children?
  18. “One of the biggest causes of misery is the way we chronically compare our insides with other people’s outsides. We’re all (…) energetically projecting an image of calm proficiency, while inside we’re improvising in a mad panic. Yet we forget (…) that everyone else is doing the same thing. The only difference is that they think it’s you who is truly competent” (Oliver Burkeman)

  19. Never forget how wildly capable you are

  20. “A lot of people seem to have a necessary level of stress, and when their life is going well, they make up imaginary problems to fill the void” (Morgan Housel)

  21. “All the greatest blessings are a source of anxiety, and at no time is fortune less wisely trusted than when it is best. To maintain prosperity there is need of other prosperity, and in behalf of the prayers that have turned out well, we must make still other prayers. For everything that comes to us from chance is unstable, and the higher it rises, the more liable it is to fall. Very wretched, therefore, and not merely short, must the life of those who work hard to gain what they must work harder to keep. By great toil they attain what they wish, and with anxiety hold what they have attained. Meanwhile they take no account of time that will never more return. New engrossments take the place of the old, hope leads to new hope, ambition to new ambition. They do not seek an end to their wretchedness, but change the cause” (Seneca)

  22. “It is quite impossible to unite happiness with a yearning for what we don’t have.” (Epictetus);

  23.  “We suffer more in imagination than we do in reality” (Seneca)

  24.  “No person would give up even an inch of their estate, yet we easily let others encroach on our lives. No person hands out their money to passersby, but to how many do each of us hand out our lives? We are tightfisted with property and money, yet think too little of wasting time, the one thing about which we should all be the toughest misers.” (Seneca)

  25.  “You live as if you were destined to live forever, no thought of your frailty ever enters your head, of how much time has already gone you take no heed. You squander time as if you drew from a full and abundant supply, though all the while that day which you bestow on some other person or thing is perhaps your last. You have all of the fears of mortals and all of the desires of immortals. You will hear many men saying “After my fiftieth year, I shall retire into leisure, my sixtieth year shall release me from public duties”. And what guarantee, pray, have you that your life will last longer?” (Seneca)

  26.  “Comparison is the thief of joy” (Theodore Roosevelt)

  27. “God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference” (The Serenity Prayer)

  28. The journey is always far more important than the destination 

  29. “The road is always better than the inn” (Ceravantes)

  30. “To travel hopefully is better than to arrive” (Robert Louis Stevenson)   
  31. “Health brings a freedom very few realize until they no longer have it.” (Bronnie Ware)

  32. You become the average of the 5 people with whom you spend the most time

  33. “What man actually needs is not a tensionless state, but rather the striving and struggling for a worthwhile goal, a freely chosen task. What he needs is not the discharge of tension at any cost, but the call of a potential meaning waiting to be fulfilled by him” (Victor Frankl)

  34. It’s never the wrong time to do the right thing    
  35. “One day, I realized with all these people I was jealous of, I couldn’t just choose little aspects of their life. I couldn’t say “I want his body”, “I want her money”, “I want his personality”. You have to be that person. Do you actually want to be that person, with all of their reactions, desires, their family, their happiness level, their outlook on life, their self-image? If you’re not willing to do a wholesale, 24/7, 100% swap with who that person is, then there is no point in being jealous” (Naval Ravikant)

  36. “If you tell the truth, you don’t have to remember your lies” (Charlie Munger)

  37. This, too, shall pass (Tom Hanks recently had a great elaboration on this quote when he said “I wish I had known that ‘this too shall pass’. You feel bad right now? You feel pissed off? You feel angry? This too shall pass. You feel great? You feel like you know all of the answers? You feel like everybody finally gets you? This too shall pass. Time is your ally. And, if nothing else, just wait. Just wait it out”.

  38. There are an infinite number of ways to achieve any given goal. When choosing how you’re going to achieve your own goals, do things that make you feel more like you. If your goal is to lose weight, some might suggest that going to the gym 7 days/week is unsustainable. However, for some personality types, it is actually much easier to go to the gym 100% of the time than it is to go 75% of the time. Whichever options feels more like you, choose it, and stop listening to others who suggest the options that make them feel more like them.

  39. It often helps to act the way you want to feel

  40. You are not your thoughts (Sam Harris)

  41. To maximize learning, growth, and progress, it is almost always better to be a big fish in a small pond than a small fish in a big pond

  42. One of the surest paths to increasing your own happiness is to spend your time increasing the happiness levels of other people

  43. Anxiety is best described as “suffering in advance”. Yet, with the clarity that only hindsight seems to provide, the majority of the things that we worried most about never actually came to pass

  44. Give yourself permission to be human

  45. FEAR = False Evidence that Appears Real

  46. Nobody has it all figured out. Including, and sometimes especially, those who seem like they do.

  47. We often try to prevent ourselves from getting too high after a win, and too low after a loss. The unintended consequence however is that we often allow ourselves to fully feel the lows, but don’t allow ourselves to fully feel the highs

  48. When we try to get the best of both worlds, we often end up getting the worst of both worlds.

  49. “Nothing like a health problem to turn up the contrast dial for the rest of life” (Naval Ravikant)

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This episode is brought to you by Symphony, a company that partners with software businesses across the entire software development life cycle, including technical due diligence, team augmentation, outsourced development, technical consulting, and more. Symphony not only performs technical due diligence engagements for search funds, Private Equity firms, and strategic acquirers, but they also partner with those buyers on an ongoing basis on all things product (outsourced development, team augmentation, new product prototyping, UI refreshes, QA professionalization, and so on). Symphony is offering a full 15% off of any of their services for readers & listeners of In the Trenches. Just go to the Contact form on their website and tell them that you’re a listener of the podcast.

This episode is brought to you by Oberle Risk Strategies, the leading insurance brokerage and insurance diligence provider for the search fund community. The company is led by August Felker (himself a 2-time successful searcher), and has been trusted by search investors, lenders, searchers and CEOs for over a decade now. Their due diligence offering (which is 100% free of charge) will assess the pros and cons of your target company’s insurance program, including any potential coverage gaps, the pro-forma insurance pricing, and the structural changes needed for closing. At or shortly after closing, they then execute on all of those findings on your behalf. Oberle has serviced over 900 customers across a decade of operation, including countless searchers and CEOs within the ETA community.

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