Category: Life

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The Question-Off

flowers, plains

One of my favorite questions as of late has been: “What is it you do to train that is comparable to a pianist practicing scales?” To me, it is fascinating to deconstruct a practice, or an action, or a set, and just drill on only one element of that practice. Every accomplished musician, athlete, veteran, chef, just to name a few, is uniquely familiar with the concept of repetition and refinement.

For example, part of my job, as now a podcast host, on top of doing research, prepping and making sure the guests are comfortable, getting involved in the editing room, just to name a few, is to ask questions. And because of the way I host Superclusters, my goal is to ask guests questions they’ve never been asked before. Admittedly, tall marching orders to those individuals whose job is to ask questions to get to the bottom of something in ways the recipients of their capital and their network may not expect. But alas I try. That said, I thought, how cool would it be if I could practice asking novel questions to someone who’s seen it all?

Admittedly, there are very few souls out there who would make great sparring partners for this drill. One that’s seen, heard, and thought of almost every known question out there. And even less I have had the chance to personally interact with. Of my limited Rolodex, luckily, the first person I asked was game. And that person happens to be this guy called Kevin Kelly.

The exercise would be, over a 30-day period, for me to ask him one question every day with the hopes that at least half are ones that he’s never been asked before. He then one-upped me and said he’d do the same. As such, it resulted in 60 queries that go beyond the obvious. While I’m not here to share the results of this “question-off”, I wanted to share the below as I hope this inspires you in ways that you might not have considered before. And if nothing else, fun journaling prompts for yourself. As such, I’ve bolded some of my personal favorites.

Kevin’s questions for me:

  1. What would you do with a billion dollars? (After you gave your family cars, houses, yachts, and vacations, you would still have a billion dollars.)
  2. Do you see yourself as part of an intellectual heritage? Who is on your tree?
  3. What is a prediction you made that was very wrong?
  4. What is the occupation that is the opposite of what you do?
  5. You get to relive one day of your past life. You could either return it as was at full volume, or you could change it. What day do you choose?
  6. If your life has a motto five words or less, what would it be?
  7. What significant law do you think should be changed?
  8. What do your friends get wrong about you?
  9. What influential person would you most appreciate a compliment from?
  10. What is something you can’t do that you’d give up 10% of your current wealth to do exceptionally well?
  11. What do you know more about than anyone else you have met?
  12. What is special about the neighborhood you live in?
  13. What question do you wish people would ask you?
  14. You get a 2-way ticket in a time machine. Do you go to the past or future? How far?
  15. What is a rule you gave yourself as a child that you still keep?
  16. What is the most recent thing you did for the first time?
  17. Who is a thinker more people should know about?
  18. What’s the strangest compliment you’ve ever received?
  19. What widely accepted “fact” do you think will be proven false in the next 50 years?
  20. What’s the most useless skill you’re proud of?
  21. What is one non-obvious piece of advice you would give to someone who wanted to get rich?
  22. They are making a film about you. What should the theme song be?
  23. What is a famous book you think everyone should read, but for a reason other than the one it’s famous for?
  24. What is something everyone you know of has done, but you have not?
  25. What is the most profound thing you’ve learned from a work of fiction?
  26. What is a popular piece of advice that you think is completely wrong?
  27. What part of you is a mystery to you, the part of that you least understand?
  28. What memory do you return to most often?
  29. What’s the most persistent myth people have about you that you’ve never bothered to correct?
  30. What’s a small thing you lost that still bothers you?

My questions for Kevin:

  1. What was your earliest relationship with money?
  2. Was there any specific groundswell in your early childhood and early life that led to the highest rate of change and growth? Were they largely technological, political or cultural in nature?
  3. If you had a billion dollars to create a secret society that will last 200 years into the future, how would you go about doing so and what would they be working on?
  4. As someone who’s used ChatGPT to write a novel you’ll never publish, yet has been an original thinker, thought-provoking writer for decades, what parts of your writing — no matter how far into the future, no matter how good the AI gets — will you never AI touch?
  5. One of the pieces of advice you once gave was to be able to learn from those you disagree with or offend you. Has there ever been a relationship that has most challenged the grounds of which your ideals stand on? How do situations that have led you to refine your ideals differ from those that reinforce what you believe in?
  6. 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?
  7. Kevin, you’re a futurist. You see the world beyond the horizon. But to take a step back, there’s a quote from the show The Office that I really like: “I wish there was a way to know you’re in the good old days before you’ve actually left them.” With all the doom and gloom around us today, what are the reminders you keep close to your heart that today, we’re still in the good old days?
  8. There’s so much gravitas and leniency given to a founder and their crazy ideas, but I’m curious, in your opinion, what were the greatest innovations at WIRED that weren’t a Kevin idea?
  9. Has there been a habit or practice you’ve observed from an interviewee of yours that you’ve worked into your own rotation?
  10. What, if anything, do your peers oversimplify about being a writer? And what, if at all, do they often overcomplicate?
  11. What was your first failure? How did you know when to quit?
  12. If you were to put together the perfect interviewer piece by piece Mr. Potato-Head-Style, how would you go about it? Who’s the researcher? Who opens the interview? Who’s the one in charge of going deep in questions? Who closes out the interview? Who’s responsible for the in-person interview setting?
  13. What is the question that has taken the most mental calories for you to answer? Why?
  14. You took a variety of roles across your career — some of which you’ve co-created and started, others you joined. Were “what’s best for the company” and “what’s best for Kevin” aligned the whole time?
  15. When you have time to wonder, what’s the thought of idea you regularly find yourself coming back to because you find it so interesting, but most of the world may not?
  16. What about your past do you desperately not want your children to know about?
  17. One of the great Kevin Kelly-isms out there is “Don’t be the best. Be the only.” How much time and discipline do you think is necessary for an individual to fully appreciate that they themselves are the only one doing something? At what point does it become part of their identity?
  18. As an enthusiast who’s been enamored by photography since you were in high school and took a deep dive into it in 1970, if you had a camera that could only take three photos total starting from today, what three moments would you photograph?
  19. When was the last time you adopted the habits, wisdom, or advice from someone you disliked or held very little respect for?
  20. What is an example of a mentorship relationship that you’re particularly proud to have your fingerprints on?
  21. What’s something others would believe you’d be highly proficient in, but no matter how hard you’ve tried in the past, you’ve found it extremely difficult to raise your skill level at that?
  22. What is it you do to train that is comparable to a pianist practicing scales?
  23. If you lived your life 1000 times, would would be true in 999 of them?
  24. What is the greatest accomplishment that you regret having achieved?
  25. 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?
  26. What coffee table books best encapsulate Kevin’s personality today? And would your coffee table have looked different today than in your 30s?
  27. If you could only choose 2 personality traits to pass on to your grandchild — 1 strength and 1 weakness, which 2 would you pass on?
  28. What was one major life decision you’ve made where it was better to not over-intellectualize the decision-making process and shoot from the hip?
  29. You’ve had a non-traditional path to your life and your career. The stuff that typically goes in movies. And in so much of what you do, you’re a dreamer. You’re a visionary. How much did they first pay you to first give up on your dreams? Why did you say yes or no?
  30. As someone who’s once recommended people to go to funerals, what is your biggest fear around what someone might say at yours?

Photo by Ahmet Yüksek ✪ on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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Why I Don’t Pay for LinkedIn Premium

ruler, short

“I didn’t have time to write a short letter, so I wrote a long one instead.” — Mark Twain

I write on this blog because I can write to think. I can write as a stream of consciousness. But at the same time, it is just that. It’s long.

But when it comes to reaching out and getting a stranger’s attention, there’s beauty in brevity. 200 characters. If you can’t get the attention of someone you don’t know in 200 characters. Hell, even 100 characters. Then no pitch deck, no long blurb ever will. Just because a house has more square footage doesn’t mean you’ll stop and visit the house.

People are busy. Investors are busy. Recruiters are busy. The world’s smartest, brightest, most ambitious are busy. A great cold message can go further than almost any warm intro can. Most people are just not good at writing them. They’re too verbose. (Caveat, a lot of my outreaches are too, but I highlight the 20 words they need to pay attention to in that email. And they may not all be in the same sentence.)

To be fair, LinkedIn Premium is really the Trojan Horse for this short piece. Keep exercising the cold outreach muscle.

I still do it every week. And so far, the response rates to ones I handcraft are better than what AI can write for me. The platform of outreach may vary. Question I always think about is where are the people I’m reaching out to spending a lot of attention, but there’s just that slight deficit of inbound information. Sometimes, it’s literally a messenger pigeon.

Photo by William Warby on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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Intro Policy

dogs, meet, intro

I used to send intro requests for as many people as I humanly could. Admittedly, a sillier, more naive me a long, long while back.

The most number of intro requests came from people I did not know. Usually founders. Given that I had just entered the venture world at that time, I was labeled as an investor or, at least, someone, who was connected to the investor world based on my LinkedIn. I also had a habit of adding anyone who reached out to connect (unless they were obviously spam). At the time, I thought, “What was the downside?”

Spoiler alert: There is a downside.

They would try to tell me about their startup. Then asked if I would invest. I’d say no, so they’d ask if I knew anyone who might be interested. A fair question. And a natural lead-in, had I offered any names, to: Can you intro me to them?

In trying to be a good Samaritan, I’d ask for the deck and blurb in a forwardable email. Half of them would. Half of them would say something to the effect of “You know enough about my company already; you write the email.”

And my dumbass, fearing to offend, would go out of my way to write intros for strangers who didn’t even bother to write anything themselves. So, I’d send that email to a friend or colleague in the industry. “You interested?” along with the email they sent me. And if they didn’t, just their LinkedIn, website, and/or deck.

Naturally, most would say no. Some would ask for my take on them. To which, I’d share that I didn’t know much about them outside of the obvious. I wasn’t investing myself, but they wanted to meet. 10-20% of the time, some friends and colleagues would say yes. (To this day, I wonder if it was just their policy to say yes to all warm intros or they were trying to be considerate of me. Some, over the years, I’ve asked. As such, it’s all the above.)

Over time, I would just include “I’m not investing. Only met them once.” in addition to “You interested?” in those emails.

Then one day, and I don’t remember when I first thought to myself, why the hell am I putting my reputation on the line each time for someone I don’t know and personally haven’t bothered to dig deeper only to write an email to show I also didn’t care about them? Why would I put myself through that? It had also become emotionally taxing to me to go through all those actions only to disappoint the founders (and myself) 99% of the time. Not only would I feel bad (often delayed disappointment and resent at myself), but I also wasn’t doing anyone any good.

So I stopped. Full stop. Period.

Around the early innings of the pandemic when it felt like there was a greater influx of deals and noise.

My rule became, and still is, unless:

  • I’m investing/invested
  • I’m advising (investing my time)
  • I’ve worked with you before and I would instantly jump at the chance to work together again
  • I’ve hired you
  • I’ve known you for so long and to a level we’ve become good friends and I feel like you’re a good reflection of the people I choose to surround myself with (that does not mean you have to be successful, but that you need to have good values and the discipline to pursue them)
  • You are someone I care about
  • Or someone, that has wowed me in a fundamental way.

AND I know the other person who you want an intro to well enough…

I’m not writing any intros.

I still read every email I get. Cold or not. And I still respond to every warm email I get. But for my fragile heart that can’t stand disappointing more people and the volume of emails I get, I’m not responding to any emails that look like they’re templated, AI-generated, or written without care. So I can focus on the ones that matter.

Photo by Collins Lesulie on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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Vacation Responders

vacation, beach

I started this practice back in 2019, inspired by two legendary people, but also that vacation responders are so boring. Why? If I’m going to take time off to have fun, why not make my out of office response fun to read as well. And so I followed through. Every vacation responder I’ve had since has always been… different.

The more I did so, the quirkier they got. And I found it as a fun creative writing exercise too. I took it so far to the point that of the many different email addresses I’ve been lucky enough to have over the years, I almost got “fired” because of my vacation responder through that email address. “You don’t seem to take your job seriously.” I do. In fact more seriously than most I’m led to believe. And I love what I do. Every career choice I’ve made I’ve made with the intention of serving the people I do serve with the utmost respect. Customers. LPs. Investors. And so on. But doesn’t mean I can’t have fun. I don’t take myself seriously, but I do take my job.

Then recently, having just gotten back from a break, a friend asked why I don’t share my vacation responders publicly as potentially inspiration for others to write interesting vacation responders. And I thought, why not?

I don’t plan to start a movement here. This may just be me and my own weird sense of fun and what makes me giggle. But in case it might offer you a little giggle as well if you haven’t emailed me when I’ve been out, sharing my last three vacation responders below.

Pandora

The date is [date redacted]. I’ve just been told that I won the government lottery to be shot light years into space to find answers – to go to the largest moon of the planet Polyphemus, Pandora. Nervous, but ready, I’m jotting this in my diary before I go into cryo.

[NEW ENTRY]

The date is [date redacted]. I’ve just awoken from the best slumber I’ve had in a long time. Only to be interrupted by this rude guy called Miles Quaritch. Apparently, I’m only allowed to address him as Colonel. He looks like the person Colonel Sanders would be if he did P90X instead of fried chicken.

I’ll be updating this diary periodically before I one day return back to planet Earth.

[UPDATED NOTE]

Training is tough. Got the lights knocked out of myself a few times. Now sitting with a black eye as I’m recording this entry.

[UPDATE 2]

Food is odd but good. Still learning when to use utensils and when not to. Seems like the general answer is to not to.

[UPDATE 3]

Ahhhhhh, they found us-…

[UPDATE 4]

Hell has broken loose!!

[UPDATE 5]

All is quiet on the western front.

[UPDATE 6]

Ahhhhh-…!

[UPDATE 7]

I’m alive.

[END TRANSMISSION]

I know I’m supposed to say I won’t be able to respond until I get back on [date redacted], but the truth is I’ll be lying out of my ass. In always having my phone with me, I will more likely than not see a notification blip pop up on my phone lock screen, assuming I still have service on Pandora. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself I’d unplug and enjoy my life as one of the Sky People as best as I can. So, I’m going to run an experiment. I’m going to let you decide:

  • If your matter is really urgent, resend the email with your subject line preceded by [URGENT] and I’ll try to respond nimbly.
  • Otherwise, I’ll respond when I return to the beautiful SF.

Escaping into chaos,

David

Feudal Japan

So….. I just watched Shogun. A phenomenal show. 11/10 would recommend.

Loved it so much I created a time machine. You didn’t just scoff at me, did you? Who are you to say that I can’t invent one? We have robots, quantum chemistry, DNA cloning, generative AI. Of course I can make a time machine.

Not to reveal my hand too much here, since I’m not sure the world is ready to accept a time machine yet, but an EKG’s ability to monitor micro-pulses and a quantum computer that can perform quantum calculations based on limited historical datasets can do wonders.

Anyway, by [date redacted], I will have been whisked away into the historic lands of Japan. Unfortunately, I will have very little reception as Starlink will have yet to exist in 17th century Japan. I hope to come back well-versed in tea ceremonies, bladesmithing, and with the honor of being a shokunin in a craft. On the off chance I get caught in the feudal wars between rising warlords, I’ve designed a failsafe that will pull me back into the 21st century on December 2nd, hopefully with all my four limbs attached.

I know I’m supposed to say I won’t be able to respond until I get back on [date redacted], but the truth is I’ll be lying out of my ass. In always having my phone with me, I will more likely than not see a notification blip pop up on my phone lock screen, assuming I still have service in historic Japan, which is possible since I’m using the neuromodulator in the time machine as the connection point to connect to 2024’s technology. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself and my partner I’d unplug and enjoy my time off as best as I can. So, I’m going to run an experiment. I’m going to let you decide:

  • If your matter is really urgent, resend the email with your subject line preceded by [URGENT] and I’ll try to respond nimbly.
  • Otherwise, I’ll respond when I return to the beautiful SF.

Cheerios and orange juice,

David-san

Outie out

I am told by my outie that he will be going away for period of time. And as I have gone through the severance procedure, as your humble innie, I will be unable to get back to you within that time. Not because I don’t want to, but I just won’t be awake then.

My outie has been quite stressed, but in the wellness room, they tell me he is loved and he has friends, and for these next few weeks, he’s spending time with people who love him.

I know I’m supposed to say I won’t be able to respond until I get back on [date redacted], but the truth is I’ll be lying out of my ass. In my outie always having his phone with him, our only mutual access point from the outside, he will more likely than not see a notification blip pop up on his phone lock screen, assuming we find a way to reconnect our innies on the outside, which should be possible as we have a master plan in place and an all-access card to make our innies’ voices heard. And I know that from time to time, I will need to interrupt my vacation to answer something urgent.

That said, I promised myself and my partner I’d unplug and enjoy my time off as best as I can. So, I’m going to run an experiment. I’m going to let you decide:

  • If your matter is really urgent, resend the email with your subject line preceded by [URGENT] and I’ll try to respond nimbly.
  • Otherwise, I’ll respond when I return to the beautiful SF.

Innie out,

David

Photo by Upgraded Points on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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On Writing

writing, journal

I’m not a good writer.

As a kid, I wrote poetry because it was easier to express myself in short form than long form. I also used to start writing fictional books, but stop after chapter one because I didn’t know how the story would develop. I was also the kid who would find five different ways to say the same thing in grade school, just so that my essay would hit the page limit. Yet still, my lowest grades among any subject was still English, particularly writing.

David Ogilvy, the namesake for the legendary advertising firm, Ogilvy & Mather, now just Ogilvy, once said: “Woolly minded people write woolly memos, woolly letters and woolly speeches.” The truth is I was, probably still am, a “wooly minded person.” But I try to be better.

That was the genesis of this blog. I didn’t have grand hopes of becoming famous. Or that I was going to make a career out of this. Still so, as it is still the reason why I haven’t said yes to any sponsors to this blog.

I write to think. I write whatever comes to mind. Simply, I write what I want. In fact, when the fact I have this blog comes up in conversation, I still actively tell me to unsubscribe. This isn’t an LP blog. Nor a VC blog. Nor a startup blog. It’s just my train of consciousness. Something I commit to every week. So, I’m extraordinarily honored to have a few thousand of you read this on a regular basis.

Thank you.

I don’t say that enough on this blog. But to all of you reading, I am deeply grateful you’re on this journey with me.

But… over the years, people have said I’m not as bad as I say I am at writing. Which might be true. We are all, after all, our own harshest critics. While I’m nowhere near the level of David Ogilvy or Brandon Sanderson or Maria Popova or Neil Gaiman or Susan Cain, in case it might be helpful, here are the gentle reminders I give myself when it comes to writing:

  1. Write as I talk. Incomplete sentences. One word sentences. Short, easy words occasionally sprinkled in with a $10 word I like. Tenacious. Idiosyncratic. Judicious. And yes, I’m conscious that I use ‘bandwidth’ instead of ‘time.’
  2. Write only when I’m inspired to. I don’t have a strict regimen of writing. I’ve met authors who have four-hour morning writing routines. I don’t. This is not my full-time job. But I enjoy writing. And I’m not publishing daily. I’ve committed to weekly. That affords me an immense amount of latitude for ‘productive time to be bored.’ I’m more often inspired by ‘touching grass’ as the kids call it than I am staring at my monitor or journal.
  3. In case I’m on a deadline and I’ve been uninspired up till the deadline, I have a very specific doc I reference. The metaphorical ‘break glass in case of emergency.’ It’s called the Emotion Catalogue. In it, I’ve tracked every single time I’ve consumed a piece of information that led to a specific emotional reaction. Happiness/joy. Sadness. Regret. Guilt. Jealousy. Anger. Inspiration. Fear. Creativity. Not sure if the last one is an emotion, but to me, it is. And if I’m supposed to write about a certain emotion, I need to feel that emotion. So I go to that catalogue, pick one or two of the inspirations within a section. And I consume it. Read it. Watch it. Listen to it.
  4. Use productive time to edit. Use inspired time to write. For me, that’s usually (not always) writing in the evening. And editing in the morning.
  5. I ‘idea-journal’ every day. If I can’t think of a new idea to write on, the journaling prompt I have to answer, “What is the most important question I should be asking myself today?” or “What did I really not want to do today? Why?”
  6. Write for one person. You. Or for me, the person I was yesterday. I am always guaranteed one happy reader. But also, if it’s helpful for me, there’s a good chance I’m not alone. And it’s helpful for someone else out there as well.
  7. Rewrite things often. The first idea is usually not the best, nor is it the most refined. Even if it’s five years from now.
  8. Be comfortable with dropping ideas. Sometimes I’m motivated to write something, but I lose motivation halfway through. Instead of making it homework for myself, it’s easier to mentally drop it. This is different from ideas I’m still motivated to write about, but can’t find the right concepts or words to put it into play. Those I mull over for a while. Sometimes, years.

Photo by Yannick Pulver on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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My Advice is Better than Your Advice

clown, stormtroopers, different

One of my favorite Hunter Walk lines, and one I cite quite often is: “Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.”

Investors are more likely to drive a company to the ground than otherwise. Founders listen to the advice of people they deem to be more senior and more experienced than them, as if they were written into the Bible. The cold, hard truth for people who give advice is that:

  1. Not all advice is created equal and most advice is situational.
  2. Your advice is more likely to be useless than useful in the aggregate supply of advice.

Advice should always be taken with a grain of salt. And oftentimes, certain pieces of advice is overweighted given the brand of the person giving it (who is right vs. what is right) and/or given the number of times the advice is given.

I’m lucky enough to be asked to be an advisor to a small number of funds, startups, and non-profits. Nothing to ever be worth bragging about. In fact, sometimes I wonder why I have a seat at the table. Nevertheless, lucky to share a drink with people smarter than me. I also realize that I’m a work in progress, and love to learn, just for the sake of learning. I’m not the famous person in the room, nor am I the most experienced person in the room.

So…

  1. I always preface my advice with “Take this with a grain of salt, and this is purely my opinion – one among many others. I trust you to make the final judgment call of what makes the most sense.”
  2. I give the unorthodox opinion. If I don’t have one, I don’t share any advice. I will caveat that I play in the early stages of company formation, when organizations are more so the pirates than the navy. When things are non-obvious, and need to fight to have a seat at the table. And given that the company and/or fund’s job is to question the status quo, I believe it is my job is to enable the founders to consider unorthodox paths. The minimum I can do is suggest that even if my advice is wrong, there are more paths than the one or two options we have in front of us. Or as Mike Maples writes in his book Pattern Breakers, “breakthroughs require pattern breaking.”

All in all, is my advice better than yours? Or anyone else’s? Who knows? But at least it’s different.

Photo by Mulyadi on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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Happiness

I had a number of people ask me what I’m doing next. So I told them.

One of the key pillars of what I am doing now is content. It’s why I write this blog. It’s why I produce Superclusters. It’s why there are a few new projects I’m working on that will shed light to this opaque world in which we’re in. Particularly in venture. In the allocator world.

I don’t hold anything back. There are no other cards I’m hiding up my sleeve. When a friend, an acquaintance, a stranger ask me how I do something, I tell them. Unfiltered. Without restraint. Without reservation. Without hesitation.

And for some reason, recently I’ve had more people ask me why. “What’s in it for you?” “What’s your master plan?” “Do you make more money this way?” “Why not just do X?” “You know you can get people to pay you a lot of money for this.” “Aren’t you afraid of being obsolete?”

Some questions come from a place of fear. Others, a place of greed. None of it from a place of joy.

There’s nothing in it for me, except for one thing. If I can help one more person not fall through the pitfalls I went through, or help one more person live a more meaningful life, or help one more person smile, I’d do it in a heartbeat.

There’s a great line I remember watching in the show After Life. “Happiness is amazing. It’s so amazing it doesn’t matter if it’s yours or not. A society grows great when old men plant trees the shade of which they know they will never sit in.”

I just want a better world. I want to make people happy. And I don’t care if it’s my own. But making another person truly happy makes me happy.

Whether you believe me or not, that’s up to you. But that’s all I have to say.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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Feeding the LP Beast

feed, bird

My family and friends have always enjoyed local restaurants and never found that higher end culinary flair ever satisfied the beast within. Also, having been a swimmer in a prior lifetime, I also ate like a vacuum cleaner. Food was inhaled rather than chewed.

In 2015, my mentor brought me to my first fine dining experience. One with a Michelin star at that. It was a multi-course meal, filled with words I knew the definitions of, but the permutation of which left me perplexed. Palate cleanser. Salad forks and dinner forks. Kitchen tours. And more.

I remember one distinct course where they had served us clams with the shells attached in a bowl. And another ornate bowl after we de-shell. The messiest part of the dinner, to be fair. After we were all done, they cleaned the table and brought us a glass bowl of water. With slices of lemon and grapefruit, adorned with flower petals.

Thinking it was a complementary drink, I took a swig. It was akin to spa water. Cool, and rather refreshing. Contrary to the calming effect of the drink, I saw, out of the corner of my eye, our waiter run across the room faster than any Olympian. After zigs and zags between tables, he stopped abruptly at our table. Now the whole restaurant stared curiously at what would happen next. Between lengthy exhales, he said, “Sir, this bowl is for washing your hands.” Embarrassed, I apologized profusely. To which, he consoled me profusely back. He took the bowl to get us a new one.

As I looked over at my dining mate, he said, “Man, I’m glad you took that bullet for us. I would have done the same.”

Nowadays, especially if I’m in a fine dining establishment, I almost always ask, “How would you recommend us to eat this?”

Most fund managers start the meeting off, almost immediately with the pitch. Most founders do the same too. I was at a virtual conference last week, where I was matched with 8 GPs on a 15-minute speed date, 6 out of 8 jumped straight into, “Let me tell you about my fund.” I get the urgency, but the first meeting should always be an opportunity to get to know the person you are talking to. As Simon Sinek says, start with the why. Then the how. Then the what. Most flip the order when they’re in pitch mode. Hell, some may not ever get into the ‘why.’

Most LPs do not invest in venture full-time. In fact, it’s the asset class they know least well. And within their smallest bucket of allocation, aka venture, emerging managers are the smallest of the smallest bucket in their larger portfolio. So if amount of capital equated to depth of understanding, most LPs know bar none about venture. At least, compared to you, the GP, who is pitching. Some may think they know a lot. They may even want to invest directly in early-stage companies themselves. And while they may not admit it to you, a number of LPs think your job, as a venture capital GP, is easy.

You, I, and every investor who has spent meaningful time in venture and is not deluding themselves, know that this is the exact opposite of any easy job that anyone can do well. Do note, raising capital easily and deploying capital easily and supporting entrepreneurs easily are all different things.

Nevertheless, depending on the LP’s proficiency level, you need to remind them:

  1. On venture and its risks (why the asset class) — Compare the asset class to others. Buyout. Real estate. Credit. And so on. Set expectations explicitly. If you yourself are not capable of comparing and contrasting between the asset classes, you should learn about the others yourself.
  2. Why emerging managers (Big multi stage fund vs you the Fund I) — You are not Andreessen, GC, Redpoint, Emergence, IVP, Industry, you name it. Neither should you at a Fund I or II. The risks of betting on emerging managers is present. If an LP indexes the emerging manager venture asset class, they’ll be disappointed. The mean is great, but the median is horrible. At least, compared to other asset classes they could be investing in. Do not pitch them, “emerging managers are more likely to outperform.” Inform them of the real risks at play.
  3. Why vertical/industry — Many emerging funds are specialists. For good reason. Based on your past experience, you’re likely to have more scar tissue but also real learnings than in other industries you did not have exposure to. Just like the first two, set the stage. How does your industry compare to others?
  4. Why you — Why the strategy? Why do you have GP-thesis fit? Why have all your previous experiences culminated to this one point in time to start this fund? And is your interest in running a firm enduring? If not, it’s also okay, but be explicit about it.
  5. Why they loved you — This is for the venture-literate LP AND if they’ve previously invested in you. Now they’re deciding if they should re-up. Were you true to your word? Have you stayed focused enough that your bets are still largely uncorrelated to the other bets in the LP’s portfolio? Why are you as awesome, but ideally more awesome compared to the last time you’ve chatted?

In that order. Starting from (1) to (5). Do not skip (1), (2), and (3).

If you jump straight to (4), that LP will consume that information within their own biases. Something you may not be able to control. And that will either make a fool out of them. Or a fool out of you. Just like I was at my first fine dining meal.

No one wants to be a fool. Don’t give anyone a chance to be one.

Photo by Santiago Lacarta on Unsplash

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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#unfiltered #93 Shifting Focus

focus

Folks with frequent flyer miles here know that I’m a big fan of Brandon Sanderson’s lessons on creative writing. So, when Brandon Sanderson shared his new course on YouTube, I had to check it out. And I’m glad I did. In it, there’s a story on a Hollywood pilot for a new sitcom.

A team in Hollywood would bring people in, and subsequently tell them that team would ask the test audience what they thought of the pilot episode after they watched it. People would then watch it. After, they would ask, “There was a commercial at break number one. What brand was this commercial for?” Why? They didn’t want people focusing on the commercials, but wanted to understand the efficacy of the commercial. According to Brandon, they used the same sitcom pilot for years, which they used as the constant to test the commercial itself.

As such, Brandon’s advice to writers was that you shouldn’t ask too many leading questions when asking for feedback. Otherwise you’d predispose your audience to the intentions of your script.

Interestingly enough, I wrote a piece last week on how I do references. In it, I also share some of the questions I use during diligence and reference calls. While the questions aren’t intended to deceive, they’re designed to get to the truth. For instance, instead of asking for a person’s weakness, you ask “If you were to hire someone under this person, what qualities would you look for?” If I were to ask a stranger about their friend’s weakness, 9 times out of 10, I’ll get a response that’s a strength in disguise. A stranger has no incentive to tell me negative things about someone they have known for a while.

But at the same time, my job as an investor, though only a minority investor, is to help their friend grow. And I can’t help them grow if I don’t know what are areas they need to grow in.

As such, the focus isn’t on weaknesses. But shifting the framing to areas where I can complement them. Areas that if they worked on them in the next two years will make them a more robust leader.

There’s also another exercise I’ve really enjoyed working on with founders and emerging managers. I’d host a dinner where most people don’t know each other and what the other people are building. I don’t give them time to introduce themselves, but I ask every single person to bring their deck. During the dinner, they’re required to give their deck to someone else at the table. Each person then has a max of two minutes to look at someone’s deck, with no other context. After two minutes, decks are put away. And each person is required to pitch the startup or the fund as if they were the founder.

It’s a self-awareness exercise. Too often, when we’re looking at our own pitch day in, day out, we tend to lose perspective. We tend to miss things that are obvious to others. Through the above exercise, each person is able to notice what someone with limited time and attention took away from their pitch and what the delta is between what the founder wanted to convey and what the other person ended up conveying.

Photo by Romain Vignes on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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2024 Year in Review

2024

Undeniably, one of the most insightful books I read this year has been Setting the Table by Danny Meyer. Someone I’ve been a long time fan of. If you’re no stranger to this humble blog, you’ll notice his cameos throughout previous pieces I’ve written. I am also remarkably late to the game. The book came out in 2008. And to this day, is as timeless as it was over a decade and a half back. Thank you, Rishi and Arpan for gifting me a copy.

That book has led to blogposts like this and this. To finally cold email him (yay, he replied! Danny, if you’re reading this, thank you for making my day, hell, and a good portion of my year!). New ways on how I support GPs. More intentional ways to hire. Inspired me to take on two more writing projects and a new podcast series in 2025 (don’t worry, Superclusters isn’t going anywhere, but expanding). And I’m sure it’s only the tip of the iceberg.

And as one last fanboy moment for Danny, there’s a line he has on page 220. A line the late and great Stanley Marcus of Neiman Marcus fame once told him. “The road to success is paved with mistakes well handled.” A line I haven’t stopped thinking about since I read it.

There’s a saying in the entrepreneurial world that it takes between 10 and 15 miracles for a startup to succeed. Each miracle is a trial by fire. A right of passage. A test of character. I’ve always believed that the job of an investor is not to be helpful all the time, or share celebrations on social media, or facilitate just connections. Despite having done many of the above myself, those are all, in my mind, table stakes. Rather, the job of an investor is to be there for at least one of those critical points of failure and to be extremely valuable. To help an entrepreneur handle their mistake well, to borrow Stanley Marcus’ line.

In another episode earlier this year, Jaclyn Freeman Hester shared one of the best soundbites ever said on Superclusters.

“If I hire someone, I don’t really want to hire right out of school. I want to hire someone with a little bit of professional experience. And I want someone who’s been yelled at.”

While it makes for a great clickbait title, the lesson extends further. One only gets yelled at by making a mistake. One learns not by making mistakes, but the public embarrassment of that mistake. If someone learn of the negative aftermath of a mistake, one won’t get the feedback mechanism necessary to grow from that experience. To analogize it to elementary math, if my afterschool teacher didn’t slap me with a ruler every time I got 9+8 wrong, it would have taken me a lot longer to learn that lesson. If no one catches you accidentally making an inconsistent calculation on the balance sheet, you may never learn from that mistake.

All that to say, someone who’s been yelled at made the mistake, received the feedback mechanism to improve, and learned to handle it better next time.

So, in my long preamble, and not to bury the lead, 2025 will be the year of big mistakes. Maybe. Hopefully, well handled. 2024 was the year of laying the groundwork. A lot of which were made explicit via this blog. I’m not saying I haven’t made any mistakes. Yes, I’ve left the toilet seat up. I should have asked for more concrete examples during certain podcast interviews. Almost forgot to file my annual tax extension. Forgot to mention a sponsor at an event (luckily my co-host had my back). Made the rookie intern mistake at work. Twice. Different things, but nevertheless twice. But those mistakes will be small compared to the ones I’ll make next year.

Nevertheless, here are the hallmarks of 2024!

2024’s Most Popular

  1. Timeless Content for the Weary Investor — Our society spends quite a bit of time focusing on results, outputs, and success. All of which are lagging indicators of the blood, sweat and tears people put in. So instead, earlier this year, I thought it’d be interesting to compile a list of content that some of the most successful investors (LPs and VCs alike) consume. What goes in their information diet? What are the inputs? Some results may surprise!
  2. The Science of Selling – Early DPI Benchmarks — With the economy outside of AI hitting a standstill and hitting record low numbers in terms of liquidity, I’ve found a constant stream of new readers via this blogpost. Many of which I imagine to be fiduciaries and capital allocators. I do hope that one day there is more content on selling and exiting positions in a liquidity-constrained environment though. Although, I may just put out a blogpost on secondaries in the new year, inspired by a number of conversations I’ve had this year already.
  3. How to Break into VC in 2024 — It may be obvious by now that there’s no one set path to get into venture. I’ve worked with colleagues who ranged in majors from history to food science to economics to computer engineering. Additionally, those who have been a founder, a banker, a consultant, a product manager, an artist, an athlete, an actress, a public relations specialist, and the list goes on. But if you were looking for the closest thing to a silver bullet, maybe this essay would be a great place to start.
  4. Five Tactical Lessons After Hosting 100+ Fireside Chats — Surprisingly, this has stayed as a perennial blogpost. I realize even now looking back, how much I’ve learned since, but nevertheless a good starting point for those who want to interview others.
  5. The Non-Obvious Emerging LP Playbook — The first blogpost I wrote on the topic of being an LP. Still my longest one to date. Since then, I’ve learned an LP comes by many a name. Capital allocator. Asset owner. And more specifically, the difference between multi-family offices and single family offices. Family businesses. Access versus asset class LPs. And more.
  6. Non-obvious Hiring Questions I’ve Fallen in Love with — I’ve been lucky enough to spend quite a bit of time around talent magnets this year. And in the surplus of applications, they’re forced to quickly differentiate signal from noise. And these are some of the questions I’ve heard them use. And well, have also used myself when hiring these past two years.

All-Time Most Popular

This list hasn’t changed much this year. One can say I have yet to outdo myself. Which may be true. I admittedly, also haven’t shared these blogposts much on Twitter. In fact, over 70% of this year’s posts never touched LinkedIn or Twitter. When in the past, I invested a bit more time in expanding to new audiences. For any essay that did go a little viral this year, it was because of you, my readers. So thank you!

  1. The Science of Selling – Early DPI Benchmarks
  2. The Non-Obvious Emerging LP Playbook
  3. 10 Letters of Thanks to 10 People who Changed my Life
  4. 99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice
  5. Five Tactical Lessons After Hosting 100+ Fireside Chats

2024’s Most Memorable

This year was the year of LP content. Also, the year where I stopped using as many headers in my blogposts. Interestingly enough. It wasn’t any conscious decision, but at some point I just slowed my pace down. Excluding this blogpost and a few others. I wonder if I’ll use less next year.

So, to share them chronologically, here are some of my personal favorites:

  1. The Proliferation of LP Podcasts — I wrote this back in March at the beginning of Season 2 of Superclusters, and I still stand by this today. At the beginning of every content adoption curve, the question is: WHERE can I find this content? But as the content becomes fully adopted, in this case around being a capital allocator, the question will become: WHO do I want to / choose to listen to?
  2. From Demo Day to First Meeting: My Demo Day Checklist — There are times we have to make fast decisions when faced with a volume of options. Going to Demo Days and choosing who to follow up with is just one of such cases. I’m happy this year I’ve codified that practice when going to VC accelerator Demo Days. And I imagine it’s only a matter of time, before we’re faced with the volume of YC Demo Days, but for funds.
  3. The Power Law of Questions — As I’ve grown as an LP, I find myself being a lot more intentional with questions I ask fund managers. This blogpost serves as a record of questions I found myself asking quite often this year.
  4. Emerging Manager Products versus Features — In the startup world, the concept of products and features have become quite prevalent. One is a standalone business. The other is more of a subclause than a clause, incapable of being a product offering in of and itself. As I spend time thinking about an asset class, where the simplest, and likely, most facetious way of describing it, is we sell money, this blogpost serves as “value-adds” that deserve their own fund versus ones that should be built within a larger shop.
  5. Shoe Shopping — One of my posts where the title almost has nothing to do with the blogpost itself. But an observation of what differentiates VC funds beyond what they pitch the public.
  6. ! > ? > , > . — Another one of those blogposts where it’s hard to guess what it’s about from the title itself. Likely my worst essay title to date. Or best? A product of my gripe that most people don’t know how to ask for feedback. And good news! Some readers of this blog have reached out since asking for more directed feedback.
  7. Three E’s of Fund Discipline — A lot of GPs focus on entry discipline. A lot of LPs in 2024 focus on exit discipline. Both are equally as important, but both often forget about the third kind of fund discipline. Executional discipline. I give examples of each in this essay, which hopefully can help as a reminder for what is needed out of a great fund manager. A separate job description from just being a good investor. In fact, you can be the latter without ever needing to raise or manage your own fund, and still make the Midas List.
  8. Anecdotal Telltale Signs of Exceptionalism — One of the blogposts I imagine will continuously be updated. As even in 2025, I’m making edits to this one. This, at the end of the day, may just sit as an easter egg hidden in the deep corners of this blog. But for me, it will be a public log of things I’ve noticed, things I like, and things that I’ve seen work well for really exceptional people I get to meet and be friends with.

With that, 2024 comes to a close. See you all in the new year!

Photo by Eyestetix Studio on Unsplash

If you want to check out the past few years, you’ll find them encased in amber here:

4/12/2025 Edit: Added in Anecdotal Telltale Signs of Exceptionalism as one of 2024’s most memorable blogposts. One of the few blogposts that is likely to be dynamic, as opposed to static.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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.

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