Creativity starts at 2 degrees

creativity, hand, paint

One degree of freedom removed from the status quo is what most people, even if they can’t do, can imagine. And because they can imagine itโ€””I could have come up with that idea myselfโ€โ€”what you have doesn’t feel innovative. They may ask you โ€œwhyโ€ once, but theyโ€™ll get to the answer they expect to hear pretty quickly.

Starting at two degrees of freedom removed, you start at the imagination’s imagination. The fringe of the fringe, so to speak. Then, by most people’s standards, you are creative. Not one standard deviation but two standard deviations from the mean. Which starts putting you in the uncommon 5%.

It’s where the average person starts calling you “built different”. I don’t know if that phrase means anything if itโ€™s overused or used by people who refuse, for whatever reason, to be different themselves. But nevertheless, you are 1 in 20 of their friends who feel like they and their 19 other friends are doing the same thing. If you want to impress insiders and people labeled by others as โ€œbuilt different,โ€ you need to be two more degrees of freedom removed from that. At least 4 degrees of freedom removed from the mean. So instead of โ€œwhy,โ€ they usually start their line of questioning with โ€œhow.โ€ โ€œHow did you think of that?โ€

If you’re taking the โ€˜perfectโ€™ stat sheet of a hire these days, across different variables (schooling, prior companies, prior job titles, years of experience, extracurriculars, skills, resume template, cover letter template), a normal applicant exudes familiarity across all the above variables. The โ€œrequiredโ€ five years of experience across companies youโ€™ve heard of, but may not be extremely exciting. They go on hikes on the weekends, hang out with friends, watch Netflix. Theyโ€™re applying for a Director role through the job portal and submitted a cover letter with references, having been a Senior Manager and Manager before that. A hire thatโ€™s built different will have all the above, except for two. Instead of climbing the corporate ladder, they started a company and sold it to private equity. They didnโ€™t apply through the job portal, but directly cold emailed the hiring manager delivering a deep dive report on what problems they see in the organization and how to fix them. Thatโ€™s a hire thatโ€™s โ€œbuilt different.โ€ But in the world of exceptionalism when there are hundreds, maybe thousands, who can/have done the same, you need all of the above and more. You built a media business on the side. You also went the unorthodox path of schooling yourself. Self-teaching. You created a podcast to interview people in this field to help you learn. You started more than one business here. And youโ€™ve come via the referral of a board member.

If youโ€™re an artist drawing a horse, the average artist will draw a long muzzle, side-set eyes, a mane, four legs, a tail, a smooth back and maybe a saddle. A innovative artist might instead draw a horse with a long muzzle, a side-set of eyes, a mane, four legs, a tail, but instead of a smooth back, draws with the armor of an armadillo. A creative artist will take all of the above, and change the legs to octopus arms and the tail into a skeletal one with a barbed one that ends with a flower. At some point, as you iterate more, it stops looking like a horse, and something else entirely.

I find this to be useful exercise in all areas that require imagination or in industries where there are incentives to be different. Craftsmanship and art being more obvious examples. Startups fundraising. VC funds fundraising. Saturation of the job market, especially with hires in AI requiring deep domain expertise and/or different perspectives. Football plays in overtime and you have the ball. Cold emails to busy people.

Of course, there are industries or moments where it pays to be the same. Where a large amount of trust is involved. Where the risk of something adventurous or out of scope could be catastrophic (to lives, to reputation, or to income/revenue). Where you only have so much wiggle room before you are alienated. Political campaigns. Kids asking for money from your parents to buy โ€œgroceries.โ€ Neurosurgeons. Flying a plane with passengers (unless this is a Red Bull campaign). Choosing your safety gear when going free climbing.

But I dare say most could use some creativity.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Offloading vs Outsourcing

consulting, outsourcing, advice

Offloading is when someone (or something i.e. AI) does the work that you know how to do yourself, but you would rather save the time you would have on the task on something else. You know how to course-correct an action, input and output. You know right from wrong. What makes sense from what makes no sense.

Outsourcing is when someone (or something) does work you donโ€™t know how to do yourself. When you get a result, you don’t know if it’s a good or bad result. You have no idea the implications of that result. Everything seems to make sense.

When youโ€™re new to a space or young in your career, and you have no prior relevant experience and context to rely on, you should avoid outsourcing at all costs. In other words, AI is quite detrimental as it stands now to help you become an expert. It will be world-class at helping you become mediocre.

The first time I read a term sheet having no other reference point, everything made sense to me. The first time I read an LPA, the same was true. The first time I read the clause “the general partner should spend a reasonable amount of time on the fund”, it seemed to check out. Only later did I realize that reasonable is not the same as significant or majority. Hell, even now, I know nothing about drug discovery. And AI for drug discovery made sense to me when I first heard it, but it wasn’t till I asked my friends in biotech did I realize there were many more limitations than I expected. The list goes on. Since there are a lot of things I know nothing about.

You should spend all your calories, time, attention, energy, resources, favors on getting guidance from more experienced professionals who have know-how that do not exist in the public domain. That LLMs have yet to get access to train on.

Wisdom cannot be outsourced to AI, podcasts, articles, tweets, social media, public panels and fireside chats, and arguably any medium where there is an audience that has no reason to withhold any secrets.

The only difference between offloading and outsourcing is taste.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Motivations

deer

Crossposting this from my LP specific Substack…

I met a family office last week and she asked me a really interesting question. Probably the question a lot of us are asking ourselves. Whether youโ€™re a VC or an LP or someone looking to hire team members.

How does one really understand another person?

The short answer is Iโ€™m still looking for the answer to that question myself. And probably will continue to do so till the day I die. Kinda like one of those questionsโ€ฆ What is the purpose of life? Is there other sentient life in the universe besides us and what are they like? What happens to all the memories we forget? But I digress, though you can probably guess Iโ€™m writing this piece in a good mood ๐Ÿ™‚

And so I responded.

Doubt I or anyone really has the answer to that. But thereโ€™s that Charlie Munger line: โ€œShow me the incentives, and Iโ€™ll show you the outcome.โ€

My first step in every investment conversation is understanding why someone does what they do. Are they trying to prove someone wrong (ie a parent, an ex, their kids, former boss, etc.)? What is their chip on shoulder if they have any? What gives them joy? What gives them pride? How do they identify themselves? Who do they see themselves as? Is there something theyโ€™re unwilling to tell me? Why? Whatโ€™s stopping them?

And some permutation of the questions below is what usually comes up in conversation. While I donโ€™t have a checklist of questions I have to ask, as long as Iโ€™m not sure what my sparring partnerโ€™s motivation is, I keep trying to figure out. Hopefully, the below questions serve as inspiration for you. Or are just more questions to your arsenal.

  • What is your selfless motivationโ€”the one that goes in the Forbes interview? What is your selfish motivationโ€”the one you tell yourself when youโ€™re struggling? Your selfless motivation will inspire you on your best days. Your selfish one will keep you going on your worst.
  • What do you want to have written on your epitaph? Do you have adjectives or words you particularly like?
  • What is the greatest regret youโ€™ve had? Why?
  • Whatโ€™s the greatest thing youโ€™ve ever done that no one around you knows about? Proudest?
  • Whatโ€™s the proudest sacrifice youโ€™ve made that no one knows about?
  • Is there a question no one has ever asked you but you would like to give the answer to?
  • What is a question you feel uncomfortable asking me?
  • Is there a set of questions you would feel uncomfortable if I asked you?
  • Why did your spouse first fall in love with you?
  • Why do you think each of your former bosses hired you? Would you say they all hired you for the same reason?
  • What’s the closest you came to breaking?

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Questions

tea

My girlfriend and I hosted a tea tasting omakase at our home over the weekend. Three teas and tea pairings across a few hours, with activities mixed in.

Our friends really seemed to like the questions they were asked as part of our icebreaker at the very beginning of the tea tasting experience. So thought that it might be worth sharing for all of you, as, say, introspective queries that you might journal with. Call them journaling prompts. Or 69 questions to fall in love? The number 69 was not intentional, by the way.

The below are just a combinations of questions that I’ve liked over the years, questions I’ve heard from others that I liked, and questions I’ve personally come up with. If you’ve been around here for a while, you might see some familiar lines of queries from the podcast, this blog, and even my question-off with Kevin.

  1. 528 Hz is the love frequency. The miracle tone. The Solfeggio frequency โ€” that very pitch โ€” that certain songs are tuned to make you feel inspired and emotional. To take a different definition of the word pitch, was there a pitch or story youโ€™ve heard in the past that inspired you to take action for seemingly unexplained reasons?
  2. If you could open a store and only sell one object that is meaningful to you, what would you sell?
  3. What’s the closest you came to breaking?ย 
  4. What’s an adjective you would use to describe your relationship with your mom?ย 
  5. It’s the last day of kindergarten, and you have the chance to walk home with the child you once were. What would you say to them?ย 
  6. What is it you do that you use to give you confidence?ย 
  7. What is a question you feel uncomfortable asking me?ย 
  8. Whatโ€™s something difficult youโ€™re going through that people donโ€™t often see?
  9. Is there a single question or a set of questions that has yielded you outsized returns when it comes to getting to know a person?ย ย 
  10. Charlie Chaplin has this great line where he says, โ€œLife is a tragedy when seen in close-up, but comedy in long-shot.โ€ Do you remember a part of your career or life that seemed like a tragedy in the moment, but is something you laugh about now?ย 
  11. What were some of your come to Jesus moments in the past few decades that your friends may fail to appreciate?ย 
  12. Iโ€™m curious, as you one day age and start to slowly lose your memories, what would be the last memory you would hold dear?ย 
  13. Has there been a habit or practice youโ€™ve observed from a friend or colleague that youโ€™ve worked into your own rotation?ย 
  14. What does one need to understand about your childhood and early upbringing to fully appreciate the person you are today?ย 
  15. If someone were to look at your calendar and only your calendar, what would they say your priorities are? What would you like to say are your priorities?ย 
  16. If you could pick any of the lessons in your life to canonize in a time capsule, which two would you pick?ย 
  17. Is there a routine or framework that serves as the scaffolding to how you think about life?ย 
  18. What, if anything, do your friends/spouse/family often oversimplify about being you? And what, if at all, do they often overcomplicate?ย 
  19. Whatโ€™s the worst pain youโ€™ve ever been in that wasnโ€™t physical?ย 
  20. Whatโ€™s the one โ€œwhat ifโ€ that keeps you up at night?ย 
  21. Whatโ€™s the biggest chance you never took?ย 
  22. What or who have you given up on?ย 
  23. Steve Jobs famously said that a typography class he took back in school was one of the most seminal experiences in his life and how he ended up building Apple. Iโ€™m curious, for you, was there a moment that you would attribute much, if not most, of how your mind works today?ย 
  24. What do you think makes your partner so successful?ย 
  25. In what ways do success fuel ambition and how might success damage ambition and hunger?ย 
  26. Whenโ€™s the last time you had a pinch-me moment?ย 
  27. What talent do you have that youโ€™re not using?ย 
  28. What is the no or refusal you keep postponing?ย 
  29. What commitments have you made that you no longer believe in?ย 
  30. What is the gift you currently hold in exile?ย 
  31. Is there anything you think the world is too dogmatic on? And in what ways are they too skeptical?ย 
  32. What in your life before you turned 18 was most formative to the person you are today?ย 
  33. If today, you could pick the age youโ€™d pass away, assuming youโ€™d be healthy the whole time, what age would it be? And why?ย 
  34. Whatโ€™s a system or game youโ€™ve hacked in the past year?ย 
  35. Can you think of a recent example where you said yes to something you shouldnโ€™t have?ย 
  36. What was your first failure?
    1. How did you know when to quit?
  37. If you were to put together the perfect human being piece by piece Mr. Potato Head-style, how would you go about it?
  38. If you were the main character of a movie about your life and you had an audience watching said movie, what would the audience be screaming at you to do?ย 
  39. If all your writing, speaking, and ideas were erased from the internet, and you only had the next 60 seconds to impart your wisdom, what would you say to the world?ย 
  40. Thereโ€™s a quote from the show The Office. โ€œI wish there was a way to know youโ€™re in the good old days before youโ€™ve actually left them.โ€ With all the doom and gloom around us today, what are reminders you keep close to your heart that today, weโ€™re in the good old days?ย 
  41. What was your earliest relationship with money?ย 
  42. What is it you do to train that is comparable to a pianist practicing scales? Or a swimmer going to 5AM practice just to practice a single arm stroke?ย 
  43. Do you see yourself as part of an intellectual heritage? Who is on your tree?ย 
  44. When you have time to wonder, whatโ€™s the thought or idea you regularly find yourself coming back to because you find it so interesting?ย 
  45. If someone who knows you well were to write a product review of you, what features and bugs would they list out?ย 
  46. How much of your advice is a function of a glass half full? And how much of it is a function of a glass half empty?ย 
  47. What is the greatest accomplishment that you regret having achieved?ย 
  48. What is one major decision you’ve made where it was better to not overintellectualize the decision making process?ย 
  49. What was the harshest piece of criticism you gave where you knew that that individual or project was providing more meaningful value to the world than your criticism gave it credit for?ย 
  50. What part of you is a mystery to you, the part of you that you least understand?ย 
  51. Whatโ€™s the most persistent myth people have about you that youโ€™ve never bothered to correct?ย 
  52. If you could pay a monthly subscription to be a fly on the wall of the life of one person, who would it be?ย 
  53. When was the first time you had to be the adult in the room?ย 
  54. How do you tread the terrain between doing whatโ€™s expected and doing the unexpected?ย 
  55. What is your earliest childhood memory thatโ€™s so deeply imprinted in your mind that all else fails to compare?ย 
  56. Which role have you taken on in your career made you the most nervous as a professional and what felt most immediately like home?ย 
  57. If someone wanted to do some serious mudslinging, what is the least charitable interpretation of everything youโ€™ve built, of everything youโ€™ve done to date?ย 
  58. Thereโ€™s a great line by Soren Kierkegard. โ€œLife is an ironic tragedy, it has to be lived forward but only makes sense in reverse.โ€ For all the events and experiences that serve as building blocks of who you are today, what parts of that lore were more incidental than intentional?ย 
  59. Thereโ€™s a scene from the show The West Wing said by the late John Spencer who plays Leo, and the story he shares is: โ€œThis guyโ€™s walking down the street when he falls in a hole. The walls are so steep he canโ€™t get out. A doctor passes by and the guy shouts up, Hey you, can you help me out? The doctor writes a prescription, throws it down in the hole, and moves on. A priest comes along and the guy shouts up, โ€˜Father Iโ€™m down in this hole. Can you help me out?โ€™ The priest writes out a prayer, throws it down in the hole, and moves on. Then a friend walks by, โ€˜Hey Joe, itโ€™s me. Can you help me out?โ€™ And the friend jumps in the hole. Our guy says, โ€˜Are you stupid? Now weโ€™re both down here.โ€™ The friend says, โ€˜Yeah, but Iโ€™ve been down here before and I know the way out.โ€™ For someone whoโ€™s felt the growing pains of life, who were your friends who jumped in the hole with you?ย 
  60. If you wrote a book where the first and last sentences were the same but had different meanings, what would it be?ย 
  61. โ€œWhat most people call authenticity is a costume for childhood beliefs.โ€ Iโ€™m curious for you, what are the most seminal experiences you had and remember from your childhood that shape the way you interact with people today?ย 
  62. Thereโ€™s an interesting quote by Rishabh Gautam. “Waterfalls wouldn’t sound so melodious if there were no rocks in their way.” Youโ€™ve reached heights that most people can only dream of, but Iโ€™m curious, what were the rocks that stood in your way?ย 
  63. What is one thing you believe in that most people would fight you on?ย 
  64. If you could relive one of your career highlights as a semi-regular recurring dream, which one would it be and why?ย 
  65. Would you rather relive your childhood or see the lives of one of your parents before you were born?ย 
  66. Thereโ€™s a really interesting quote attributed to Voltaire. โ€œChange is annoying, but certainty is absurd.โ€ What are you willing to be absurd about?ย 
  67. George Bernard Shaw once said: โ€œThe single biggest problem in communication is the illusion that it has taken place.โ€ Of all the quiet things that should be said aloud, what were/are your biggest offenders of the illusion of communication?
  68. What version of yourself do you miss sometimes?ย 
  69. If your partner asked you, whatโ€™s one thing you sacrificed for me that I donโ€™t know about, what would you have told them?

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Knife Shopping

knife, santoku, chef

A friend of mine was in the market for a new chef knife. The first one his wife wanted to cherish and asked me for thoughts, which gave me my little stage time to nerd out. And I thought… hell, might as well share my thoughts here as well.

So, a couple things to consider when you’re choosing a knife. For now, I’m going to exclude most of my commentary on how to take care of knives (i.e. wash, knife cloth, sharpening on whetstones, etc.).

  • How do you cut? Up/down or rolling motions?
  • What will you cut most of the time?
  • How often will you use the knife? Daily? Or for special occasions?
  • How important is knife control to you? Do you like letting gravity “do the work”?

Given your answers to the above questions, it’s easier to then figure out if German or Japanese steel is better for you, the heat treatment/HRC, full tang or hidden tang, and so on.

So let’s take this one by one.

If you cut up and down, Eastern/Japanese knife shapes may serve you better as they have straighter edges. Western/German knives have more curvature along the knife’s edge, which is useful if you cut in a rowing motion.

In general, full tang (meaning the metal of the blade extends all the way to the back of the handle) means you’re controlling the knife more. Whereas hidden tang (the metal of the blade extends partway through the handle) is more front-weighted, and more popular among chefs who “let the knife do the work.”

If you’re cutting veggies and fruits or in general softer material, knives with higher HRC (Rockwell Hardness C-scale) where higher means the metal is cooled faster, are better. And in general, allows for thinner knives and more precise cuts. Think sushi knives. Personally, I think an HRC of 58 is good enough for regular use. But some prefer 59+. The upside is that they retain their edge longer. The downside is they chip more easily then lower HRC numbers (cooled more slowly when making the knife). Lower HRC knives are better for cutting bones and hard material. They tend to dent (softer metal) rather than chip. Think meat cleavers.

If you’re using a knife regularly, say at least 3-4 times per week, I’d recommend going stainless steel (which is what most people prefer anyway) instead of carbon steel. The latter rusts easily (or patinas easily, the layer of rust that develops on the outside of low alloy high carbon knives). Also easier to upkeep with repeated washes. Do dry with a cloth instead of letting them air dry though. Knife oil helps, but is not mandatory on stainless steel knives. For presentation or special occasion purposes, aka to show off, a lot of people prefer the looks of high carbon steel knives.

In general, you can get a great starter knife for $80-200. Up to $500 if you want to splurge. But anything north of that is really the premium you’re willing to pay for each artisan.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

What is your play style?

video game, switch, play style

On a quarterly alchemy session with my buddy Matt (yes, we have a quarterly-ish ideation/philosophical debate session), he asked me, “If you were a video game character, with both pre-set stats as well as the stat points you’ve accumulated through experience to date, what’s your play style? How would you best utilize your stats and skill trees towards your goals?” Furthermore, how might someone else with the exact same stats play your character differently?

First off, I like video games. I had a gamer in me in my past. Probably still, if I were given the chance to restart. But alas, a dangerous trade for me. So do note the bias in the intellectual resonance I had with the question.

Secondly, the underlying assumption in this line of questioning is that while the distribution of stat points vary per person, there exist others who would have the same set of stats as you do and the same skill trees. The same builds. But just because you have the same builds does not mean you have to have the same play style.

Thirdly, that last question is probably most interesting. How might someone else with the exact same stats play your character differently? How might someone else reach a different conclusion to “min-max” your play style? Or potentially more critically, how are you not leveraging certain skill trees to maximize your odds of “beating the game”? Skill trees that are underutilized or have been set aside to collect dust so far. Skills you earned as a child. Or in college. Or in your first job that you failed to keep putting the pedal to the metal.

To take the gaming analogy further, every time there’s a new update, your character build has to evolve with the associated nerfs and buffs to certain skill trees. In other words, with each new world order, are your past skills more or less relevant? As such, you need to change your build every world “update.” Be it the internet to the cloud/SaaS era to the AGI era and so on. Given the pace of technology and culture, there will be several “updates” to the world within your lifetime. And no one wants to play a character with an obsolete build.

I can’t take credit for this since I haven’t read the book yet, but when I was telling another friend about the above, she used the phrase “the leash of your past” inspired by a chapter in Bjรถrn Natthiko Lindeblad’s I May Be Wrong. Which I think is quite apt to this analogy.

After all, your past self won’t thank you for staying the same, but your future self would wish you changed sooner.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

“Be strong enough to be gentle”

Three conversations happened recently.

One, an LP told me that he pit two fund managers against each other by asking their shared portfolio founder, “If you could only choose one, who would you keep as an LP?” Then went on to relay that answer back to both of the respective managers.

The manager who lost the vote shrugged and didn’t feel the need to really engage in the ragebait. The one who won the vote ended up making some remarks along the lines of “I don’t see why anyone would ever want to work with [insert other GP’s name].”

Two, similarly, I met a GP for the first time last week who pitched me a strategy he thought was unique. To which I responded with, “What are your thoughts on [insert VC firms with similar theses]?” He replied with a whole list of reasons of “why X, Y, and Z should never be in business in the first place.”

Three, I caught up with another Fund I GP earlier this week. Second conversation, who pitched me a strategy he thought no one else was doing. I asked the same question, listing some competitors with the same strategy, stage, and focus. He said he’d never heard of them, then asked me to repeat those names. He Googled each. Scrolled through their portfolio and website and LinkedIns. Then started his response with, “I guess I’m not as unique as I thought I was. Here’s what I think they’re doing right…”

All three conversations carry notes of similarity. Each either directly or indirectly ending with one of two paths. In the first one with the LP, do I agree with his method of execution? Not really. But nevertheless, he received the answer he was seeking.

Yet in all three, I can’t help but be reminded of something Peter Cullen (who’s best known for being the voice of Optimus Prime from Transformers) said.

It’s not immediately apparent on the relevance. But he says, as the inspiration for how he voiced Optimus Prime, “Be strong enough to be gentle.”

True strength and mastery has no need for infighting. No need to demean others. No need to push others down only so that they will look better by comparison. Most Midas investors I know are not bragging about the fact they’re on the Midas List, at least I haven’t heard Vinod or Marc brag about it. They’re on the Midas List because they can pick great companies. It’s not that being on the Midas List allows them to pick great companies.

Those that are the best of their craft, across industries, and that I’ve been lucky enough to be in their presence are both gentle and generous with their learnings. What’s proprietary is the execution not the idea. And by being generous and gentle, you end up commanding a lot more respect and admiration. If you’re truly stronger than others, you know how to control your strength. And only use it, when necessary. Most situations do not demand the necessity.

You need not prove your strength to a flower. Neither a butterfly. You need not prove your strength to a baby. To a feather. The inability to control one’s strength for the situation required can only exist in the absence of maturity. And the absence of mastery.

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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

The Wrong Question for the Ambitious

I was chatting with a friend over the weekend who made me look stupid.

We were catching up after a while and we were talking about career paths and opportunities, and I had shared that I was offered to join a few large institutions late last year and earlier this year. Both of which I eventually turned down. And that one of the canonizing questions I had in the back of my head among 2-3 others was: When I leave, could I say I was successful because of the institution or in spite of the institution?

And for the first time, after sharing that set of questions with a few friends when I was in the process of making a decision, someone called me out. “That’s a bad question. That’s a horrible question.”

He goes on, “The question presumes that you are either joining a has-been or never-was institution OR that you couldn’t do anything meaningful while you were there. Given the names you’ve told me, the former is most likely not true. Instead, the framing of the question should be:

“What can you do at this institution that no one else with that job title has done?

“Something you actually wrote about before. On top of that, what can you do at this institution that no other institution would allow you to do? And how can you leverage the hell out of that? Why would you even join an institution where you can’t even leverage their success to date? That would make you look dumb for joining a bad institution when you have the opportunity to join a great one.”

Photo by Timothy Barlin on Unsplash


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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

GP EQ

conversation, eq, fundraising

A conversation with an LP reminded me of this recently. Can we trust a GP’s word that they’re a good picker if they can’t assess how likely an LP is to commit?

I’ve had multiple conversations with GPs where they tell me XXX and YYY are excited to come in the fund, and they just need more time to close their fundraise or for their process. Then the same XXX and YYY LPs ghost these GPs for months on end. For me, that’s enough for me to question their level of commitment, but not having been in those conversations firsthand, I can’t speak to the actual incentives. Sometimes, I actually know XXX and YYY LPs well enough to pick up the phone and dial them right away and ask them what’s up. Which I do. Only to hear from them and they say they had passed already.

Now I don’t know what actually goes on between those two parties. What’s said and what’s not said. There are many LPs out there who give very soft “no’s.” In hopes to not offend, they imply it’s a “no.” There are also LPs who explicitly say it’s a “yes” ONLY IF ZZZ happens. Given the current market, most of the time, ZZZ doesn’t happen, which becomes an easy out for the LP. The LP’s felt like they’ve delivered the “no.” The GP is still hanging onto the hope the LP likes them enough to break the rule. And then, there are many GPs who have selective hearing loss.

Nevertheless, there are multiple instances of this. And it’s not my job to point fingers to any party other than elucidate that this exists in our world.

That said, even if an LP doesn’t explicitly say “no”, there should be enough breadcrumbs to point to whether someone is a pass. Probably harder to know if they’re a “yes.” But there’s definitely writing on the walls if it’s a pass. And it’s almost always better to assume an LP is an out than an in if there’s hesitation.

The outstanding question for someone like me or any of my friends who I’ve had this conversation with is… is this indicative of a GP’s EQ when talking to founders? Is this GP more prone to rewriting history and facts? Is there a massive perception bias here and is the GP living through rose-tinted lens?

Richard Feynman has this great line. “The first principle is that you must not fool yourself โ€” and you are the easiest person to fool.”

And I’ve also had this conversation with another GPs a few weeks back, and I said, “You’re either lying to me or you’re lying to yourself. One is worse than the other. But neither gives me a reason to back you.”

Photo by Priscilla Du Preez ๐Ÿ‡จ๐Ÿ‡ฆ on Unsplash


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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.

Casting Shadows

shadows

โ€œWhen small men begin to cast big shadows, it means the sun is about to set.โ€ โ€” Lin Yutang

It’s been 10 years since I first stepped into venture. Yet still, while I know more, have met more people, and have experienced more, and when I look back, I pity the knowledge and experience I had a decade prior… yet despite all that, I know I have still so much work to do.

This essay was born from many conversations over the years, but especially so, in the past few months, where I’ve witnessed conversation after conversation that follows the theme of:

“Have you met X?”

“I have.”

“What do you think of X?”

“X feels far smarter online than X is in reality. After meeting X, where I anticipated so much, I was only let down.”

Never meet your heroes, they say.

In venture, we live in a world where the average VC brags more about “being a part of the journey” or “excited to support” a founder they backed than actually doing the work. It’s no wonder that 70% of VCs add no value (though 15% more add “negative value”). But it is far easier to say the part, look the part, than do the part. With SpaceX and OpenAI’s IPO today, Anthropic’s tomorrow, and Databricks, Anduril, who knows what, the day after, we will find many more VCs congratulating themselves, raising larger vehicles, and casting larger shadows.

In an unreleased interview with a GP I really admire, she told me an anecdote of a founder she knows well. “All of my early stage investors made out like bandits with my huge exit, and I never got a thank you. All I saw was them talk about how they discovered me and how they had such a big role to play in my success. But no one said, thank you for returning my fund 10 times over. And here’s a token of appreciation, whatever the appreciation is.” Which echoes the growing sentiment in the ecosystem.

And here’s my own self-reflection.

I hope that I cast no greater of a shadow than my beliefs, thoughts, and remarks would allow. And I hope still that I have the humility to cast a smaller shadow than I would ever be allowed to.

People measure shadows by the potential and impact someone may have. I have a friend who turned 30 recently. And when we sat down to chat, he told me that people were no longer telling him that he has potential. And one of his greatest fears is that people only see the person he is today for who he is today, and no longer the person he will be tomorrow. That pressure, more than anything, meant he was no longer “young.” I don’t think anyone ever loses their potential as a function of age. I have friends double my age, still learning every day, faster and more studious than people half of theirs. To me, that is still potential.

And here I hope that the shadow I’m capable of casting is underestimated than overestimated. But at least to myself, I hope I never underestimate myself.

โ€œAfter Iโ€™m dead, I would much rather have men ask why I have no monument than why I have one.โ€ โ€” Cato

Photo by Pete Walls on Unsplash


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The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.