Category: Life

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#unfiltered #90 If A Song Took a Lifetime to Play

music, song

Just the other day, I was listening to one of 99% Invisible’s episodes, interestingly titled as “As Slow As Possible,” named after the organization ASLSP, which stands for the same. My knee-jerk reaction was that the abbreviation and the first letters of each word just didn’t match up. Luckily, Roman Mars and Gabe Bullard explained. Although it still left something more to be desired.

“The title is also a reference to a line in James Joyceโ€™s novel Finnegans Wake. The line is: ‘Soft morning, city! Lsp!’ Where lisp is just spelled L S P.”

Nevertheless, the episode itself circles around the concept of taking one song and using the entire lifespan of a pipe organ (639 years) to play that song just once. That even a single note would take two years to play. A fascinating concept! And which led me down a rabbit hole of thought experiments.

What if we took our favorite song and extrapolated that to the human lifespan? Say 90 years. What note would we be on today? Have we gotten to the chorus yet?

So for the sake of this thought experiment, for a brief second, let’s walk down the lane of music theory. Take the average pop song. The average pop song plays for about three minutes. And many at 120 beats per minute. Apparently, 120 bpm is also the golden number you want to get to if you’re working a crowd as a DJ. You never start at that speed, but you work your way up throughout the night. And if you can get people’s heart rate matching the beats per minute, you’ve hit resonance. But I digress.

So, taking round numbers, the average pop song has a total of 360 beats. Most songs are in 4/4 time. In other words, four beats per bar. An average pop song takes about 2-4 bars for the intro. 16 bars for a verse. Possibly, another 4 bars as the pre-chorus. And the first chorus doesn’t really start till bar 25. And usually lasts another 4-8 bars.

Now, if we were to extrapolate a song to the average human lifespan. 90 years. 360 beats across 90 years. Assuming it takes 24 bars to get to the chorus, the chorus doesn’t start until we’re 24 years old. And the full chorus doesn’t end until we’re 32 years old. With each note lasting a full three months. And the second chorus starts around age 48.

Then again, I remember reading somewhere that most pop songs are played in multiples of four or eight. And that most of these songs only have 80 bars. If that’s the case, the first chorus doesn’t kick in till we’re just past 28 years old and ends around 36 years old.

In either case, the first chorus happens around the time when most people would define as their prime. Young enough to take risks; old enough to be dangerous. The second chorus seems to fit as the second wind people have in their careers. Hell, HBR found, the median age of a startup founder when they start is 45. And with that reference point, they’ll be 47 or 48 when they become venture-backed.

Obviously, this is just me playing around with numbers. Correlation does not mean causation, of course. But nevertheless, the parallels… curious and uncanny.

P.S. Jaclyn Hester and my episode together on Superclusters got me thinking about a lot how much music applies to our lives and how we live and think.

Cover Photo at the top by Marius Masalar on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜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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#unfiltered #89 The Palate Setter

cheese

Around the time I wrote a blogpost on culinary tips I had amassed from various chefs, I ended up getting one more piece of advice from a James Beard award winner. The culinary equivalent of a Pulitzer. In fact, one piece of advice that came in right after I clicked publish on that blogpost. Which I subsequently failed to include.

I had asked, “How do you know the palate you come into the kitchen with today is the same as the one that you came in with yesterday? And similarly, what about the one tomorrow?”

To which he responded, “I don’t know.” For a brief second, there was silence. Both of us knowing that the void will be filled, but left there for dramatic effect. “Swiss cheese.”

“Huh?”

“Swiss cheese. Not the fancy stuff, the one you find in the refrigerated section in the supermarket. Every day, when I go into the kitchen, I take a bite of swiss cheese. To me, it has the perfect balance of umami, salt, nuttiness. And the supermarket brand one is always produced with a consistency in their quality. If my bite that day is not as salty, then my palate is muted, and I should salt my dishes that day a little more. And so on.”

And I found that fascinating. Recently, I was reminded of that advice when I was chatting with my friends on preparation rituals. When we start something, to get us in the right mindset, what is the set of practices in which we use to orient ourselves?

Back when I was still swimming competitively, we used to always say the hardest part about swimming is getting in the water. Effectively, starting. The below were some other rituals that came up in that conversation. Part in hopes that it may inspire you to start your own, partly to make sure that I immortalize these practices for myself.

Music

The tuner in many ways is the swiss cheese in music. Something so consistent that it becomes the benchmark for what sound should be. Is your instrument too sharp or too flat?

But from a ritualistic perspective, I’ve seen many play the scales to loosen their fingers, but one of my favorites from my buddy who plays the flute in the orchestra is beatboxing, while playing the happy birthday song. The song choice itself matters less than using one’s entire mouth to enunciate certain beats. And so, by the end of the song, the windpipes and larynx are fully massaged and ready to go.

Podcasts / Streaming

For me, it’s doing 20 burpees while listening to a collection of my favorite podcast clips that I’ve saved from other podcasters, then sitting down and skimming through this list of catchphrases that I’ve since called “The Rookie Guide for Veteran Podcasters.”

For another friend, who’s far more accomplished than I am on this front, it’s doing a series of vocal exercises and facial massages. The former of which expand in both pitch and volume (from a whisper to singing in a voice suited best for operas).

From a third friend, it was religiously taking a 1-hour nap about an hour before the recording session.

Giving live talks

This isn’t from any of us in the room at the time. But Tim Ferriss has also gone on record sharing what he did in preparation for his first SXSW talk when we just launched the Four-Hour Workweek. That he was staying in a friend’s home who had cats. And he kept practicing his talk in front of the cats trying to get their attention. None of which, I assume, knew anything about what he was talking about, yet if he could convey his intent, energy and emotions through to the cat, he’d have a fighting chance getting the audience’s attention at SXSW.

Photo by Camille Brodard on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜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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#unfiltered #88 Koi No Yokan

love, heart

In a late night conversation with my high school friend last week, I picked up a fascinating Japanese phrase from her. Koi no yokan.

The best translation of it that I found was ‘the premonition of love.’ It serves as the antithesis to the notion of love at first sight. It’s love that takes time to grow on you. Slow, but steady. A seemingly acquired, yet inevitable sense of fate. It’s a feeling that begins when you meet someone you’ll eventually fall in love with.

It’s a remarkable concept with no direct English parallel. It sits in rarified air between words like hiraeth, hyggelig, and yลซgen. All of which have inextricable meaning behind a seemingly simplistic string of letters. While I’ll leave the afore-mentioned three to your own rabbit holes, as you might imagine, I’ve been having quite a field trip across the linguistic landscape.

Koi no yokan.

It’s a concept that’s often applied to the enamor between humans. This may just be me being a sacrilegious foreigner, but I find the same linguistic beauty with passions.

In many ways, my love for the emerging GP and LP world was the same. If you told me back in college, that I’d want to spend a few decades of my life obsessed over demystifying the space, I’d have called your bluff. Might have even called you bonkers.

And while I’d been hovering like a satellite around the space for a while, it wasn’t till I started writing The Non-Obvious Emerging LP Playbook that I realized there was an inkling of a yearning there. Answers only led to more questions. Each insight I learned was always paired with another punctuated with a question mark. And it honestly was a really fun exercise. I didn’t write that blogpost for anyone else. Just myself. Like a public diary that encapsulated my intellectual expedition in the LP world. Even before I published it, even before any other feedback I got for it, it felt special. All catalyzed by an opportunity to back a first-time fund manager I’d been honored to see grow as the last check in.

At that point, I still had neither committed to the idea of really being a capital allocator nor to the promise of more of such content.

And when that blogpost finally saw daylight, and a number of readers responded in kind, a tenured investor asked if I was going to write a book. It seemed only fitting that a non-fiction 200-page book be the successor to the 12,500 word blogpost. So pen met paper.

I revisited old and forged new relationships off the momentum of the blogpost. And around 80 pages into the manuscript, I ran out of things to write. I didn’t know how to continue. It felt both lacking and comprehensive at the same time. I could add in more examples. Case studies. Or just superfluous language. The equivalent of turning “my dad” into “my wife’s father-in-law.” The latter of which I swore to myself I wouldn’t do.

So I stopped.

Put it aside. And went on with the rest of my life.

But time and time again, I’d find myself staring at the ceiling at night, journaling, or writing on my whiteboard in the shower about the afore-mentioned topics. It became borderline annoying that my mind kept circling back to it and I was doing nothing about it.

So frick that. As I once learned from Max Nussenbaum, who I got to work with sooner after, the fastest way to test out if there’s a market for your ideas AND if one’s interests are sustained across longer periods of time is to just write about it. And I did. Here, here, here, and more.

At one point, my buddy Erik asked if I was going to start a podcast. At first, I dismissed the idea. Didn’t think I had the skillset or the personality for one. But man, I lost even more sleep in the ensuing weeks after he seeded the idea in my head. And so I started a podcast. (Which holy hell, I can’t wait to show you Season 3 on July 1st)

I realized much later, probably a year after I stopped writing the book, that the reason I couldn’t write anymore, despite asking so many really smart LPs for help, wasn’t that there was nothing more to share, there was still a lot… Hell, even each family office had a strategy so unlike the next. And as the saying goes, if you know one family office, you really only know one family office. So no, it wasn’t because there was nothing else to write. In one world, I could have just written an encyclopedia of strategies. It was that there was so much that had yet to be written, ever, about allocating into emerging managers.

Venture as an asset class was not the Wild West, still an alternative and still risky, but there have been predecessors who’ve productized the practice. But allocating to Fund I’s and II’s without proof of a track record was a horizon most had yet to cross.

Hell, I wrote a LinkedIn post just yesterday on how I think about evaluating Fund I track records without relying on TVPI, DPI, and IRR. And why I think more funds of funds should exist.

An excerpt on my LinkedIn post

Simply put and in summary, there’s a complexity premium on not just venture capital, but specifically on evaluating Fund Is and IIs. And I don’t mean the big firm spinouts who have a portable track record. I mean the real folks who are truly starting to build a firm (not just a fund) for the first time.

I don’t have all the answers. Sure, as hell, I hope to have more in the near future. But I’m ridiculously excited to find answers (and more nuanced questions) โ€” putting science to art โ€” as an emerging LP.

If you couldn’t tell yet… I think I’m in love.

And if you’re interested, I’d love to have you join me on this ride.

Photo by Mayur Gala on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜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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DGQ 21: What’s going to get you excited to be at this business in 5 years?

watch, time

This one was inspired by Harry Stebbings’ episode with Dan Siroker that I tuned into earlier this week. In it, Dan describes his most memorable VC meeting, which happened to be with Peter Fenton at Benchmark. Where Peter asks Dan, “Dan, what’s gonna get you excited to be at this business in five years?”

In sum, what are your future motivations going to look like? Nine out of ten times, it’s likely not going to be exactly the same as the one today. And given that it will look differently, can you still stay true to the North Star of this business as you do today? What’s gonna change? What’s gonna stay the same?

For the most part, the people and the problem space are likely to stay the same. The product may look quite different though. And it’s highly likely that in five years, you would have found product-market fit. So, that’s Act I. Is it the advent of the next chapter of what your company could look like that gets you excited? Hell it might be. You can then tackle a bigger problem. A larger market. An adjacent market. Or what Bangaly Kaba calls the adjacent users. For some founders, it’s the market they always wanted to tackle, but couldn’t when they realized their beachhead market must be something else.

While I can’t speak for everyone, here are some of the answers I’ve personally come to like over the years. From either founders or fund managers:

  • There is no other industry that offers the same velocity of learning that this one provides.
  • I want my company’s legacy to outlive my own. And I want to empower the next generation of builders with the resources and the power to solve the greatest needs of our generation.
  • I want to go home and tell my my wife/husband/kids that I lived my fullest life today. And this is what gives me endless joy.
  • Act I was solving a problem I faced. Act II is solving a problem others face in our space.
  • Getting on the phone with a customer and hearing how much our product changed their lives makes me really happy.
  • If I’m not regularly putting the firm’s reputation on the line, we’re not trying hard enough. And I live for that challenge.
  • I want to build a world where people don’t settle for “It is what it is.”
  • No one else is solving the problem I want to solve in the way that I believe it should be solved.
  • I want to continue to be a superhero, a role model, for my daughter/son.

In many ways, it’s quite similar to the question I ask first-time GPs or aspiring GPs about their motivation.

Things in venture exist on long time horizons. For founders, it’s at least 7-9 years before an exit. For fund managers, it’s 10-15 years per fund. And that’s just a single fund. Anything more is longer. So in order to compete against the very best, you need to have long time horizons. You must have the resolve to stay the course. As Kevin Kelly says, “Theย main thingย is toย keep the main thing the main thing.”

Along the same vein, there’s also a Jeff Bezos quote I really like: “If everything you do needs to work on a three-year time horizon, then youโ€™re competing against a lot of people. But if youโ€™re willing to invest on a seven-year time horizon, youโ€™re now competing against a fraction of those peopleโ€ฆ Just by lengthening the time horizon, you can engage in endeavors that you could never otherwise pursue.”

Photo by Luke Chesser on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. Itโ€™s an inside scoop of what goes on in my nogginโ€™. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. Iโ€™ll let you decide which it falls under.

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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A Jerk’s Guide to Being Kind

dog, bully, fight

First off, my lizard brain that optimizes for immediate gratification thought “A Jerk’s Guide to Being Kind” would be a fun title. Clickbait-y (kinda). Great for SEO. So I used that as my prompt for this public journal entry. ๐Ÿ™‚

So, if you didn’t come for a public apology and how I say no, I’ll see you in next week’s blogpost.

Secondly, I was reading Chris Neumann’s blogpost this week, aptly named “The Beginner VC’s Guide to Not Being a Jerk.” And realized, holy frick, I’m a jerk. In it, he describes five things that VCs do that come off as jerkish.

  1. Donโ€™t Use Possessive Adjectives
  2. Donโ€™t Multitask When a Founder is Pitching
  3. Donโ€™t Badmouth Founders
  4. Donโ€™t Mansplain
  5. Donโ€™t Ghost Founders

And of the five above, I know I’m an offender of three of the above. Using possessive adjectives. Multitasking. Ghosting. Probably in that order from most frequent to least frequent. (Sorry, Chris. Sorry to founders I’ve done this to.) The first two I don’t do intentionally, nor do I do the either of them often.

Not sure if it makes too much of a difference, but rather than say “my company” or “our companies,” I do say “our portfolio companies.” Just with one extra word in there. Occasionally, will let it slip when I’m trying to shorten the sentence I’m saying.

I know I’m more prone to multi-task when I’m not the only investor in the room, and definitely when I’m not the primary investor. Again, don’t do it often, but it happens. And I never do so when I’m the only other person in that conversation. 99% of the time I do let the founders and GPs I talk to know that I’m just taking notes of our conversation. Personally don’t use the AI notetakers, but that’s a discussion for another day.

And ghosting. My goal is to get to inbox zero every day. And I really do my best not to ghost. But three things will always happen:

  1. Some email or text always ends up slipping through my inbox. Either it goes in spam, or during certain days, I’m bombarded with hundreds of emails and it slips through the cracks. And I do give every founder and GP who pitch me the right to re-surface past emails if it does slip through.
  2. If the email or message seems like it came out of an automation or mail merge AND I’m not interested, I do let it drop. I read EVERY email for sure. But if that email looks like the same one that you send to every investor, those have been going straight into the archives more and more. That also means that some emails just read like it’s an automated email even if it doesn’t, and it slips through.
  3. There’s a shortlist of people who have abused my old personal policy of responding to every email I get. And so for those people, I’m not sorry if I do ghost you. That said, it’s a pretty short list of people (probably 30-40 people as of now).

And lastly, well, I’ve made founders pitching me cry. Not something to brag about. But in sharing what I thought was honest feedback, I made tears flow.

So, in summary, I’m probably a jerk.

In my mind, a jerk is someone who prioritizes their own beliefs and priorities to the point that they either intentionally ignore or severely de-prioritize others’. Although I try my best not to ignore what other might want or need, but I do often prioritize my own. So to add on to all the above, I’m sharing some situations where my jerkiness comes out and what I say in those moments.

When having tough conversations

I actually learned this while listening to Lenny’s podcast with Matt Mochary. When I need to let someone go. When I need to call a friend out on their bad behavior. Or when my partner and I get into a fight. “Preface hard conversations with: This is going to be a difficult conversation. Are you ready?”

In addition, I also preface with how long I think the discussion will take. “May I have thirty minutes of your undivided attention?” And what the topic will be on. No point in blindsiding the other person.

It helps set the stage. And if the other person needs more time, they have the option to back out. Moreover, all tough conversations are 1:1 conversations. At least for me, even if it relates to many, I start notifying them all on a 1:1 basis.

When trying to leave a conversation at an event

This one also isn’t original. I learnt from a friend of mine who is far more eloquent than I am. Not all conversations at events are created equal. And sometimes, at an event, especially a networking event, my goal is to say hi to the event host or to talk to someone else on the floor. And in between, I may find myself in another serendipitous. Case in point, yesterday, I ended up meeting a founder who sold his last company for $500M exit to a large Fortune 50 company in the parking lot and who was figuring out his next thing. Serendipitous. And super fun, but I was going to be royally late for another event if I stayed chatting in the parking lot.

So, when I need to leave a conversation, instead of excusing myself to go to the bathroom or get more food, I’ve learned to say, “I’d love to ask you one last thing that I’d beat myself up tonight if I didn’t ask before I need to go say hi to XXX.”

One, it timeboxes the next few minutes of the conversation. Two, I’m still interested in the individual and I want them to get the last word before I head out.

For 1:1 conversations

I usually let people know at the very beginning of the conversation that I have a “hard stop” at a specific time. Which 90% of the time is true. Usually another meeting. Or I have just way too much work on my plate that I need to get to.

When turning down a meeting (for now)

I wish I had more time in a day to talk to awesome people. I also wish I had more energy in a day to talk to awesome people. But unfortunately, I only have 24 hours in a day. And well, I’m an introvert. As in, I enjoy writing this blogpost you’re reading right now since 5AM in the morning than telling someone in a live conversation what I will end up writing here.

As such, if I’m interested in meeting at some point, I usually say something to the tune of: “I would love to meet, but if I do so within the next XXX weeks / months, I would have failed in my promise to the people I care about. So if you’ll allow me to be a good friend / family member / supporter of my existing projects and investments, could we revisit this in YYY weeks / months?”

Other times to save everyone’s time, since I won’t find my interest levels gravitating towards said topic, I let people know it just isn’t of interest to me in the foreseeable future, and that their luck may be better elsewhere.

When turning down an investment opportunity

This is actually something that was inspired by one of Jason Calacanis’ podcast episodes. And while there are many things I may not agree with him on, I really like the phrasing he uses to turn down founders who push back against his investment decision. And I’ve added some lines that best fit the way I talk. Which I also included this in my 99 series for investors.

“I always have to accept the possibility that Iโ€™m making a mistake. The venture business keeps me humble, but these are the benchmarks that the team and I all believe in.”

In closing

Sometimes I think it’s inevitable to appear as a jerk to some people out there. While one can try to reduce the splash damage, the truth is sometimes what you have to say may not be what the other person wants to hear or see. But as long as you hold yourself to a high degree of integrity and do so in as kind of a way as you can, I think that’s all that really matters.

Often times, I do believe it’s more important to be kind than nice. I hope the above helps.

Photo by David Taffet 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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DGQ 19: Does the overall level of the team make me question if I’d be a good enough to play in this industry?

“I wonโ€™t forget the first time I saw Jason Peters do a one-on-one pass set with Trent Cole, and being amazed at the speed, balance, and power I just witnessed. It reminded me, or looked like, a grizzly bear wrestling a panther. It was so impressive, it made me question if I was good enough to play in this league.”

Much of this DGQ was inspired by Jason Kelce’s retirement speech, delivered with the prose and candor befitting of a legend. Which for those who have yet to read/listen to it, it’s 24 minutes that will be well-spent, whether you’re a sports, football, or Eagles fan or not.

There’s something really special about being the underdog. Whether you feel it or others say it. That slight chip on the shoulder, that measured level of imposter syndrome, is fuel to the fire. There is a distinct advantage for being the dumbest person in the room, knowing that there are mentor figures on the team you can learn voraciously from, even if by osmosis. And if you do have naysayers, you have the greatest privilege to prove them wrong. It means that you have space to grow. That journey ahead, at least for me, is quite exciting.

After all, in Jason’s 2018 Super Bowl Parade speech, he quoted another line from Jeff Stoutland. “Hungry dogs run faster.”

Although not framed nearly as eloquently as Jason Kelce put it, it’s something I think about a lot. Does the overall level of the team make me question if I’d be a good enough to play in this industry?

Challenge is as scary as it is thrilling.

Similarly in VC, we often say it’s an apprenticeship business. And it’s true. Almost every great investor I know had someone who took them under their wing and showed them the ropes. Sometimes a set of people. And it’s incredibly hard to learn and check your blindside without someone who plans to dedicate a good portion of their time to do so. That said, the next best you can get is to learn by osmosis.

You are the average of the five people you hang out with most. So if you have the chance to live and breathe alongside people who intimidate you with their skill, intellect and the way they execute in a good way, take it.

Photo by Vicky Sim on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. Itโ€™s an inside scoop of what goes on in my nogginโ€™. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. Iโ€™ll let you decide which it falls under.

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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The Proliferation of LP Podcasts

I am under no illusion that there is a hell of a lot of interest in the LP landscape today. Not only from GPs who are realizing the difficulties of the fundraising climate, but also from aspiring and emerging LPs who are allocating to venture for the first time. The latter of which also have a growing set of interests in backing emerging GPs. And in the center console in this Venn diagram of interests lies the education of how to think like an LP.

I still remember back in 2022 and prior, we had Beezer’s #OpenLP initiative, Ted Seides’ Capital Allocators podcast, Notation Capital’s Origins, and Chris Douvos’ SuperLP.com. Last of which, by the way, can we start a petition to have Chris Douvos write more again? But I digress. All four of which trendsetters in their own right. But the world had yet to catch storm. Or maybe, the people around me and I had yet to feel the acceleration of interest.

Today, in 2024, we have:

There is no shortage of content. LPs are also starting to make their rounds. You’ll often see the same LP on multiple podcasts. And that’s not a bad thing. In fact, that’s very much of a good thing that we’re starting to see a lot more visibility here and that LPs are willing to share.

But we’re at the beginning of a crossroads.

A few years back, the world was starved of LP content. And content creators and aggregators like Beezer, Ted, Nick, and Chris, were oases in the desert for those searching. Today, we have a buffet of options. Many of which share listenership and viewership. In fact, a burgeoning cohort of LPs are also doing their rounds. And that’s a good thing. It’s more surface area for people to learn.

But at some point, the wealth of information leads to the poverty of attention. The question goes from “Where do I tune into LP content?” to “If I were to listen to the same LP, which platform would I choose to tune into?“

After all, we only have 24 hours in a day. A third for sleep. A third for work. And the last competes against every possible option that gives us joy โ€” friends, hangouts, Netflix, YouTube, hobbies, exercise, passion projects and more.

In the same way, Robert Downey Jr. or Emma Stone or Timothรฉe Chamalet (yes, I just watched Dune 2 and I loved it) is going to do multiple interviews. With 20, 30, even 50 different hosts. But as a fan (excluding die-hard ones), you’re likely not going to watch all of them. But you’ll select a small handful โ€” two or three โ€” to watch. And that choice will largely be influenced by which interviewer and their respective style you like.

While my goal is to always surface new content instead of remixes of old, there will always be the inevitability of cross-pollination of lessons between content creators. And so, if nothing else, my goal is to keep my identity โ€” and as such, my style โ€” as I continue recording LP content. To me, that’s the human behind the money behind the VC money. And each person โ€” their life story, the way they think, why they think the way they think โ€” is absolutely fascinating.

In closing

There’s this great Amos Tversky line I recently stumbled upon. “You waste years by not being able to waste hours.” And in many ways, this blog, Superclusters, writing at large, and my smaller experiments are the proving grounds I need to find my interest-expertise fit. Some prove to be fleeting passions. Others, like building for emerging LPs, prove to be much more.

Photo by Jukka Aalho 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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v28.0

I came across a quote recently, which I believe originates from Qi Lu, former COO of Baidu, and the one who created Bing, Microsoft’s search engine. “Luck is like a bus. If you miss one, there’s always the next one. But if you’re not prepared, you won’t be able to jump on.”

And your bus fare comes by way of preparation. The 10-year overnight success.

Or as the classic Seneca line goes, “Luck is when preparation meets opportunity.” Or as Louis Pasteur also said, “Chance favors theย prepared mind.” And by having a prepared mind at the bus stop, you’ve increased the surface area for luck to stick.

Of course, I could fill an entire blogpost with just quotes on what luck means. But I won’t.

Year 27 on this planet was simply a year to try new things. An exploration of the human mind. An exploration of what are the boundaries of the LP landscape. And what’s worth pushing on, and what’s not. The output of which culminated in events, new ways to operate, building trust circles, the podcast, more content on the blog, and of course, a lot more conversations with influencers in and away from the limelight.

The inputs of which came from my last year’s resolution.

A reflection

Last year, the goal was to find myself in the flow state at least twice a week. Truth was, at that point in time, I had yet to figure out how to truly measure it. And it wasn’t until October 15th last year when I started measuring the early semblances of it outside of just allotting time to be in the flow state. For me, it came down to a simple question. Was today worth it?

In other words, was today well spent? Defined by either:

  1. Learning a new skill or framework
  2. Creating a core memory
  3. Or by realizing something I never realized before, a new way of looking at the world around me.

Each of which, at least for me, largely become possible when I am in an egoless state working or thinking about something proactively than reactively.

As of writing this blogpost, I’m 16 weeks in. And I have 18 days well spent. On average, between one and two days per week. Leaning more on one though.

Though I might be able to allot time on a weekly basis on my calendar for “flow state,” I’m not always in the mood for it. That in itself was dependent on circumstance, timing, stress, and the disciplined pursuit of inspiration. The last of which was a luxury I couldn’t always afford. Sometimes when there are more pressing matters, I can’t help but find my mind wandering and stressing over more urgent matters than focusing on doing something new.

As such, to help me do so, I focused on things I could control daily: Was I consuming a healthy and diverse diet of information? Which I measured through reading, listening to podcasts and content, and conversations with different kinds of people.

I also look back at my journal entries for the past year, and anecdotally, more than 60-70% of them are about topics and tasks I had to do, pre-assigned (often self-assigned due to constraints). And a lot of them focus on the 10%, maybe 20%, marginal improvement and refinement of what’s been done already, rather than the 10X thinking I find more common in journal entries in the years before. The difference between reactive journaling and proactive journaling. The product of consuming too much (work, podcast, and otherwise) of the same genre of information. Simply, I didn’t cover all my macros.

So, this year…

So this year’s goal is no different than the last. To explore. To find myself in creative pursuits and in the flow state. And to take risks.

While I remember the lyrics, I often forget Sanderson’s Second Law. “Flaws/limitations are more interesting than powers.” Constraints are the breeding grounds of inspiration.

Not sure how much of this is lore, but I remember reading once that Bill Gates loves hiring lazy procrastinators. As his words once rung, “I choose a lazy person to do a hard job. Because a lazy person will find an easy way to do it.” For Gates, the constraint of time and energy on a responsible individual is the forcing function for brilliance.

While it’d be ridiculous to give myself a pat on the back for “brilliance,” there is immense value in time constraints, as well as intentionally handicapping myself to produce results. To not let perfect be the enemy of good.

As such, I’m going to impose limitations on myself as a forcing function of iteration, and hopefully by product of doing so, I live more days that are worth it. For now, the count is 19 since Oct 15, 2023 (when I started counting).

How I will measure success, with a North Star of at least 2 per week

While I don’t know what else will come up, my goal is to color in as many pickles as I can in the fickle jar. For now, to hold myself accountable:

  • Publish the intuition vs discipline blogpost (final draft done by end of February)
  • Host an escape room where all the clues to escape are based on each guest’s individual stories (March)
  • Build a repeatable framework for backing GPs as an individual LP (by the end of February)

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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Lessons from Season 1 of Superclusters

microphone, podcast

I’m in my fourth year of writing this blog and never once have I called myself or identified as a content creator. As many of you know, I write to think. I do so out of joy and intellectual stimulation. In many ways, I write for myself. Or better put, as a form of self-expression. Other than posting in the morning, as is thematically helpful for my blog, I don’t really have much cadence to posting. Nor have I looked too deeply on analytics. Nor have I really optimized for SEO. In other words, finding the top searched topics in my industry and writing a blogpost for each of those highly trafficked keywords. I haven’t done that, nor do I want to. I haven’t chased people down to subscribe. In fact, there are times I try to convince people to not subscribe (due to the scattered nature of my content).

To that end, I had not been a content creator.

But with the launch of Superclusters, for the first time, and still a work-in-progress, I am designing the content for someone other than my immediate self. Although, do I take opportunities to scratch my own itches? Yes… yes I do.

But in doing so, I am starting to think about creating content for others. And to do that, I need to look at what people like and tune in to.

Now at the end of Season 1, some quick learnings…

Note: The below gets a bit nerdy on numbers. Mostly as an accountability metric to myself to be paying attention to the below. This may not be for everyone, but in case you’re curious, and/or working on creating your own content, hopefully the below might be helpful.

  • Between all the platforms, YouTube seems to be the most popular channel. Followed by Apple Podcasts then Spotify. Where Apple Podcasts only has half or so the number of plays than YouTube does. And Spotify has three-quarters the listens compared to Apple.
    • May be helpful to note that YouTube and Apple Podcast count plays as just someone viewing the video for a split second (“greater than 0 seconds”), whereas Spotify counts a play as someone who’s played the episode for at least 60 seconds.
  • YouTube seems to be better for discovery than the other podcasting platforms, with over 4.5X the impressions compared to the next best, Spotify. 28K versus 6K. Tracked by last 30 days, not all time.
  • For short-form vertical content, TikTok continues to perform better than both YouTube and Instagram, especially for new audiences. Still perplexes me since I imagine the demographic on YouTube has more of my intended audience. Nevertheless, even on YouTube shorts, the shorts are consumed by a younger audience than the long-form videos on average.
  • Instagram, in general, performs poorly in terms of discovery among new audiences. But that might simply be, I haven’t learned the IG algorithms well enough yet. Moreover the new algorithm seems to prioritize completion percentage. And given that it’s hard to shorten even my short-form content to less five seconds or less, unless I just make people read while playing some kind of looped video in the background, Superclusters will likely continue to perform poorly on IG.
  • On YouTube, 90%+ of Shorts viewership comes from non-subscribers than subscribers. where 75-80% come from non-subscribers, the average for the full podcast episodes.
  • On YouTube, 41% of my audience comes from the US. TO break it down further, 50% comes from the US for long-form. 27% for short-form. Spotify, 67% comes from the US. Apple Podcasts, 87%.
  • Interestingly, by city, according to Apple Podcasts, New York City takes the cake on where my audience reside.
  • Across all platforms, most of my listeners/viewers are in the 35-44 age range. Accounting for almost 50% across all platforms. Followed by the 28-34 age group, then 45-59 age group. In general, Superclusters has a larger younger audience fan base on YouTube, compared to Spotify and Apple Podcasts. The latter two with similar distributions.
  • Superclusters audience is also about 75% male, 25% female.
  • While less than 0.05%, fun fact, the only other subtitles used on YouTube to tune into my podcast was French (outside of English).

Popularity versus watch time

The most popular episode on YouTube is Chris Douvos’, followed by Ben Choi’s. Episode 1 and Episode 6 respectively. My suspicion was that while both were super fun to record, Chris’ episode came first but may by the end of Season 2 be surpassed in viewership by Ben’s.

On Apple Podcasts, it’s Samir Kaji’s. And on Spotify, it’s the post season episode with Jeff Rinvelt and Martin Tobias.

But what’s most fascinating to me is that among the nine episodes released for Season 1, on YouTube, the top four most popular episodes have shorter average watch times than the most bottom five. On average a two- to three-minute difference, where the least watched episodes happen to have 7-8 minutes of average watch time.

In closing

All in all, there’s a lot of work to do ahead. And as I’m recording Season 2 and my team is hard at work in editing those episodes, all of the above insights are helpful to keep my finger on the pulse. Do let me know if I’m missing any areas I should be paying attention to or measuring.

Otherwise, for Superclusters, I’ll see y’all again in early March for the launch of Season 2.

Keep staying awesome!

Cover photo by israel palacio 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 #86 Learning from Personal Mistakes, Excellence, and from Others

sand, filter

A few years ago, in one of my favorite coffee shops on 7th Street in San Francisco, over a vanilla cold brew, a then 25-year old founder told me that he had recently taken his then-first vacation in five years. Took a full week off. Didn’t touch work at all. And just enjoyed it with his fiancรฉe. But contrary to what one would expect, his body language that seemed to indicate the exact opposite of having a good time. Two hands cupped over his face, as he slowly dragged them both downwards in exasperation. Followed by many sighs.

He shared that in the time he was gone, the website crashed and the team had trouble bringing it back online. And when they finally did bring it back online, they were waiting for his approval to move forward. As such, didn’t bring it back online until he came back. With another large sigh, he went on to say that he’d never take another vacation ever again.

Running your own business is tough. Really tough. I get it. If you’re the founder, it’s your baby. And sometimes, it’s really hard letting go on what may seem like key decisions. Eventually, that becomes a slippery slope where I see too many founders needing to control every decision that goes on in the company. And even if you hired extremely well, you’ve capped your team’s potential by not letting them execute to their fullest capacity.

In the above dilemma, as you might know, it’s not a to-vacation-or-not-to-vacation problem. It’s a you-need-to-give-your-teammates agency problem. And it might seem obvious to you and me, to any third party observer. But it wasn’t to him. He was so frustrated that he was focused on the one new thing he did and believed that one new thing had a causal effect to a problem that was looming over his team’s head for a long time.

It is true that we are products of our scar tissue, but quite often, in an attempt to not be in the same situation again, people overcorrect. They take then run with the seemingly most extreme “solution.”

And in the times scar tissue start to form, start from first principles. Is taking a vacation really the biggest offender? Do great CEOs just not take time off? Is there something else that I’m not willing to admit about how the results played out?

What am I assuming to be true that may not have to be true? What are the raw facts, stripped of opinions and speculation?

Why was my team incapable of making that decision? Was it something that I told them before or did before that has since prevented them from making calls? What do I spend most of my day doing? Can I outsource some of my tasks? Some of my decisions? How would I do that? And only then, can I ask myself and others: what can I do from now on so that history doesn’t repeat?

Seeking and redefining excellence

And once you’re at the root of the problem, find others you admire who run organizations you admire.

Excellence is an interesting concept. One of the few words out there where its definition changes over the course of your life.

Itโ€™s one of the few words where it is not only different for every person, but that even within each person, every time you see something excellent, it sets a new bar and stretches that definition. Defined by only the most excellent thing you’ve seen.

The truth is that most great lessons happen to err on the side of examples. So to have people who define that word for you again and again are the “Sensei-s” you want in your life.

So spend time with others. Notice how they approach problems. And stretch your definition of excellence.

For the 25-year old founder who hadn’t worked any other job in his life, and only his own, there’s immense value in learning from others and building expertise at high-growth institutions. Or with people who you deeply respect.

Asking for the lesson

Tim Ferriss, on a recent episode with Noah Kagan, said, “Life punishes the vague wish and rewards the specific ask.” And I frickin’ love that line.

Be specific. No picking brains. You’re not a zombie or a vulture or a crow.

Not 30-minute coffee chats. Those quickly become recipes of asking for too much time with an amorphous ask. To a busy person, that 30-minute ask sounds like a recipe for losing 50 minutes to an hour of your life you can never get back. Including travel to and from. Time, as the only unreplenishable commodity, is precious. As Howard Lindzon said on the Superclusters podcast, when we’re young, we’re time-millionaires, but over time, we get poorer and poorer. We then become time-thousand-aires as we age. And eventually, we run out of temporal capital.

It is in times of need and struggle, that we often have the most prescient and specific ask to make of potential mentors.

“When in X situation, and after having Y results, my gut seems to tell me to do Z, but given that you’ve experienced these situations before or have likely seen these situations unfold, am I directionally accurate?”

In closing

There’s a lot of this hustle porn in the Bay Area. Loud claims of not taking any vacations or sleeping only three hours per night. Moreover media perpetuates and lionizes this way of living.

It’s not true. Science shows we do much better with eight hours of sleep. It shows that every so often, we need to take time to unwind, so that we can come back to be more efficient and inspired than before. You can clock in the hours, but that doesn’t mean you are producing quality in a one-to-one capacity.

And I worry that like the founder that took his vacation for the first time, then overcorrected, we live in a society where we’ve forgotten that we’re human. That we need breaks. That we need sleep. And that we can’t do most things alone, including building ambitious ideas and maturing as professionals.

Photo by NEOM on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. Itโ€™s not designed to go down smoothly like the best cup of cappuccino youโ€™ve ever had (although hereโ€˜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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