“I won’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.
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.
The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. 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. I’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.
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.
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 — friends, hangouts, Netflix, YouTube, hobbies, exercise, passion projects and more.
In the same way, Robert Downey Jr. or Emma Stone or Timothée 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 — two or three — 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 — and as such, my style — as I continue recording LP content. To me, that’s the human behind the money behind the VC money. And each person — their life story, the way they think, why they think the way they think — 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.
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.
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 the 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:
Learning a new skill or framework
Creating a core memory
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
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.
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.
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.
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.
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 fiancée. 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.
It’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.
#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.
Our tiny blue marble has spun yet another lap around its closest star. From a job change to starting a podcast, between visiting Japan for the first time (and holy frick is Japan amazing!) and blacksmithing my own santoku chef knife while I was there, and from building the most unlikely friendships that will last for decades to come to realizing life rarely goes according to plan — a good reminder of Mike Tyson’s line: “Everybody has a plan until they get punches in the face.” — and from attempting to convey my year in one sentence to realizing this is the longest run-on sentence I’ve written on my blog to date, it’s been a great year.
While I wasn’t aware of this till recently — courtesy of doom-scrolling on Instagram, this year’s been a year where I’ve “used the difficulty.” To echo the amazing Sir Michael Caine. For those unfamiliar with the phrase, I highly recommend listening to the full 2002 interview, but at least this.
In short, you can’t always control the situation you’ve been given, but you can control how you react to it. If you want your life to play out like a comedy. If you want it play out as a drama. Or if you want it to play out like a feel-good movie. Use the difficulty to your advantage and act accordingly.
By the numbers
Interestingly enough, despite writing whatever I find fascinating on a weekly basis — in other words, not optimized for search engines — just under half of my blog’s views come from search engines. Primarily, and I mean 95% of which from Google. Followed by LinkedIn (which accounts about a third of my views) then Twitter (~7%).
As many other aspects of life, the viewership of my blogposts also have a Pareto distribution, where they seemingly follow the power law. With my top blogpost winning more than twice the views of the second highest. And the second highest with double the audience of the third highest, before the views plateau out across all the rest of my essays. Even for this year alone, my most popular blogpost is eight times more popular than my second most popular.
And every week I feel honored that I have readers like you who tune in to my weekly musings and our family has only grown since.
Something I’ve noticed when looking at the numbers is that I seem to have the most readers arrive at this humble piece of virtual real estate every October, barring 2021. And I wonder if it’s a function of the market’s interest crests then or that I just happen to write better pieces around then.
In addition I’ve started measuring my habits since October, only to realize, holy hell, I am inconsistent with them. While I’d love to blame travel and work, the simple truth is it’s hard to manage what I didn’t measure before. Hopefully in 2024, we’ll see a lot more consistency.
P.S. the last day, aka today, is down, since the day’s just started and I haven’t logged in anything yet. And for those curious, I’m tracking this all on a Notion dashboard.
But my favorite thing that I started measuring, is that little trophy icon in the first column of the “Evening” section. And that little trophy stands for: “Was today truly worth it?” Defined by me learning a new skill. Gaining a brand new insight about the world. Or created a core memory. And I’m happy to say that that box gets checked about two times per week. 🙂
Post publish edit: The last icon is often how I take a cold dunk/shower, as opposed to a hot one. Having friends, former housemates, and my partner exclaim and tell me “I know you shower more often than that” made me realize that icons don’t do some things justice.
2023’s Most Popular
The Science of Selling – Early DPI Benchmarks — One of my favorite lines from Jerry Colonna’s book Rebootis: “It’s buy low, sell high. Not buy lowest, sell highest.” In the world of VC, we spend a lot of time talking about when to buy, how to buy, and who to invest in. But rarely about the other side of the playbook, selling. Or exiting positions. And while different investors have shared the what behind selling — in other words, the exact percentage they sold at, how much they sold when they could — this blogpost was one of the first, and maybe first (who knows), to explore the why and how behind selling positions in portfolio companies as a private investor.
The Non-Obvious Emerging LP Playbook — The blogpost that set me down the path I am now on. To explore how I can help the next generation of capital allocators is investing into the innovation economy. Simply put, the emerging LPs.
Five Tactical Lessons After Hosting 100+ Fireside Chats — In fairness, had no idea this blogpost was going to do as well as it did. And luckily, I am now able to stress-test and get better at asking questions and hosting interviews through not only what I continue to do in the world of venture, but also through my new podcast, Superclusters. Where you’ll see some of my learnings above in action.
10 Letters of Thanks to 10 People who Changed my Life — In all honesty, it still befuddles me to this day how this blogpost consistently ranks this high. I don’t namedrop here, and I don’t use any clever SEO techniques, yet every day this blogpost seems to find organic interest. Nevertheless, I’m glad it has. And if it empowers people to be more grateful to the people around them, I’ll have done my job. There’s also a deficit of content and knowledge here for sure, but I’m still trying to figure out what that something is.
How to Think about LP Construction — Not all LPs are created equal. It’s something I’ve known for a while. Both in conversation with other LPs and GPs, but also in learning of the different types of motivations to be an LP. For some, VC is an access class, not an asset class. For others, it’s the exact opposite. The latter is more likely to be a large institution. Nevertheless, that’s one example of many. And it was incredibly rewarding to hear GPs I really respect share what they’ve learned across multiple funds.
All-Time Most Popular
The Science of Selling – Early DPI Benchmarks — Turns out you all love tactical frameworks, so my goal is to share a lot more with you in 2024. I have a couple in the works as we speak (or as I write this).
10 Letters of Thanks to 10 People who Changed my Life — If anything, I hope this inspires people to write one note or letter or record a voice note of thanks to someone who’s helped you become the person you are today.
99 Pieces of Unsolicited, (Possibly) Ungooglable Startup Advice — Don’t worry already in works of many more iterations of this. And while I can’t promise when the next one will come out since it’s I’m really only including what I think are the best pieces and most tactical pieces of advice, I will say it’s a matter of when not if. I’m 20 in for the founder one. And 12 in for the investor one.
How to Pitch VCs Without Ever Having to Send the Pitch Deck — Back in 2021, I knew that this blogpost was going to hold an evergreen spot up here. And I’m pretty sure it’ll flirt around here even longer. While it’s only been two years since, and while there’s also a mountain of public resources on how to pitch, strangely, most people still struggle to connect to the people they want to. And it’s true for both founders and VCs. Ya, the latter seems ironic, until you see that founders are pitch judges, juries and executioners as well. For them, from talent. Until you also see that our parents are often the harshest critics of our decisions. Yet some have no experience working in the world in which we do. All that to say, oftentimes it’s easier being the judge than the judged. I can’t claim much of the insight here as original, but rather have to thank the fact I have really smart friends. Smarter than me at least. The flip side to the wild performance of this essay may just be one of the closest titles I have to being clickbait-y.
2023’s Most Memorable
In all honesty, the most memorable each year to me were ones where I was scratching my own itch. Some, by the numbers, perform better than others. But for me, each of the below represent the greatest delta in either knowledge acquisition or insight development. Of course, not mutually exclusive to each other.
The Science of Re-upping — I enjoyed writing this one in particular not only because I got to work with Arkady and Dave on this — two minds I greatly admire, but it also became the perfect opportunity to learn more about the world of professional sports beyond the players and scores themselves. Two birds with one stone. I’ve always admired folks who are able to pull from various, seemingly disparate topics and analogize them to venture. And while I still have many more miles on my odometer to go, this was one of the amazing opportunities to take a stab at marrying two different worlds through stories.
How to Think about LP Construction — I will admittedly take any opportunity I can to talk to my favorite people. And this was another one of them. That said, to get them all in the same metaphoric room to talk about the same topic, where the energy of one inspired another, now that’s something special. Funnily enough I did the vast majority of these interviews for this blogpost asynchronously, but upon sharing the final product with the group the week before publication, there was an incredible amount of energy (gratitude, stand up comedy routines, and so on) in the group. And all this was over email.
The Science of Selling – Early DPI Benchmarks — This, in many ways, was an accidental piece. Not only did it come up in conversation over Friday brunch quite randomly (serendipity at its finest), it also took, at least compared to the above two, the least amount of time to write. The first draft was ready in about an hour. And including all the edits, it came out to about two hours of work. It’s a gentle reminder that sometimes your best pieces are the easiest to write.
My Ever-Evolving Personal CRM — I wrote this blogpost after some coercion from a small group of friends who’ve been fascinated by how I stay in touch with people. And when they saw how I did it on Airtable, they asked if I would sell them my template (not that I had one at the time). Nor am I selling now. But nevertheless, the web of what we do, who we talk to, who we grow with, and why we do things is increasingly complicated and so far, there hasn’t been a great product out there that tracks this (and yes, I’ve used all the CRM tools out there). And so I created my own.
#unfiltered #83 There Doesn’t Have to be a First Place — I really enjoyed writing this one. Inspired by a podcast appearance by Simon Coronel, I learned that in the world of magic competitions, first place isn’t always granted. If the judges feel like a magic act isn’t on par with previous years, even if it is the best one that competition, they choose not to award a first place. Similarly, I think the world in a lot of ways has lost itself in the noise. That our definition for quality has fallen in the past decade. And I’m sure the older generations will harken back further. But I do believe a heuristic like this keeps us honest and that as a society, we move forward together, not just optimizing for short-term maximizations.
#unfiltered #78 The Gravitational Force of Accumulated Knowledge — Another fun piece to write about the power of how knowledge compounds. Not only in isolation, but also collectively. While that is a rather obvious fact, I loved the reframing of how to look at it from Seth Godin and Bill Gurley’s public interviews.
How to Retain Talent When You Don’t Have the Cash — One of the biggest lessons I learned at On Deck was that the team was amazing — in fact, world-class — at acquiring the best talent, but was shy on retaining the world’s best talent. To this day, I believe I have never worked in a higher concentration of brilliant talent than I did when I was at On Deck. And this blogpost is an homage to my former team, how brilliant they were, but also the lessons we took away from that experience.
7 Lessons from My Time at On Deck — And in the theme of On Deck, and how much I treasure the people I work with and the experience I had while I was there, last but not least, the culmination of lessons I took away from an 18-month period that I would never trade for any other experience.
And I started a podcast. Superclusters. (Or here’s on Spotify or Apple Podcasts if you prefer). It’s still too early to tell how Season 1 will do, with only six episodes in (the most recent of which here). But by next year, I should have more than enough to share about my learnings here. But early data seems to suggest that people love true stories more than they do tactics.
Until the next, stay awesome! And see y’all in the new year!
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.
Guilty as charged, but I was doom-scrolling on Instagram recently and I came across a reel where two Formula 1 drivers were asked to guess the race track given only a racecar’s engine’s audio (vroom vroom). And to my absolute amazement, the two were able to guess track after track. Some answers seemed to have only taken them a few seconds to figure out.
The Instagram reel came from this YouTube video for those who are curious.
So I couldn’t help but notice, how well they knew each track. That they had taken special notice to all the small bumps in the road. The turns. How long each turn was. All of it, without any visuals. It’s for the same reason I am always impressed everytime Bon Appetit’s Chris Morocco can recreate dishes by taste, smell and feel alone (no sight, he’s blindfolded). A lot of which is in line with the post I wrote last week. It’s not just about paying attention, but how to pay proper attention.
So this time around, I thought why don’t I bring this into the world of events. Something I’m deeply passionate about.
Experiences > Events
“Jonathan Yaffe, co-founder of the experience management platform, AnyRoad, defines an experience as something that stimulates at least three senses.”
I first read that line on page 146 in my buddy Lloyed’s book on community-building. And it made total frickin’ sense. Lloyed went on to write that Zoom sessions don’t count as experiences because it only engages one’s sight and sound. But events like Dining in the Dark, which my friend hosts, do count. Despite taking away sight, you’re tapping into taste, smell, and sound. The last of which occurs when there’s a band playing in the background, but with each course, a new instrument is added into the mix. And it’s because of experiences like these, they leave such strong impressions. Emotional impressions. Nostalgia.
Emotions, after all, are multi-sensory. And eliciting those emotions require you to fully commit. The question is how.
How to make people feel special at events
One of my favorite lessons I picked up during my time at On Deck was from Sam Huleatt. A strike is better than a spare. We were hosting sessions and events three to six times a month, depending on the time of the year. And Sam proposed that we go through an exercise. A thought experiment.
What if we only did one event per month? If so, what would that look like?
What if we only did one every quarter?
And what if we only did one every year?
How does that change the way we think about events? What changes at each stage?
Honestly, one of my favorite exercises to go through when I feel compelled to hit a certain quantity and realize I have to find the optimal point between quantity and quality.
But since then, that inspired another set of thought exercises I do.
If I had to host an event for just one person — just one — what would I do to make it an unforgettable experience?
What would need to change if I did so for a four-person dinner?
A six-person dinner?
What about a 10-person event?
What about for 50 people?
For 100?
For 1000?
And so on.
At some point, usually around 50 is when things start hitting scale. But let me break down why each of the above before 50 are inflection points:
1 person. This person is your universe. You can’t make it any more tailored and personalized than this. It’s a date.
4 people. For the most part, still only one conversation happens at a time, but now as the host, you have to make sure no one is left out.
6 people. In my mind, this is the minimum number of people for more than one conversation to be happening at once. For the first time, you have to worry about flow of the event while you’re not capable of being present everywhere all at once.
10 people. You not have more than two conversations going on. Juggling with two is easy; for some, that may not really be juggling. But once you’ve added a third and a fourth ball, then this is real juggling. Here, the host has to think not only about the number of conversations, but to pay attention to folks who become satellites to conversations. Watching for people who are distracted. Uncomfortable. On their phone. And so on. But also, when conversations go too long. As the host, finding ways for people to enter and exit conversations easily is vital. It’s better to have less time than to have too much time.
And 50 people. For the first time, you need to think about having more than one host. You can only scale your time and attention so much. So now you’re training a team to be as attentive, if not more, than you are.
The larger the event, one can say the more polyamorous you have to be. You have to deeply care for each person. And while everyone at your event likely knows you’re “dating” everyone else, if you can still make them feel special — like the most important person in the world, that their time is valued, their attention is valued, and their presence, mind and insights even more so — then you’ll have done something 99.9% of event hosts have not been able to do. Frankly, probably would rather not do. ‘Cause, at least if you start small, it’s not crazy work. It’s quite easy, just requires more effort than most are willing to give.
Other times, event hosts just scale their events too quickly. And hit scale before they find their magic. So, if you can, do unscalable things before you hit scale.
Notice when in a conversation someone’s eyes divert. Notice when they ask to leave to use the restroom. And notice when people lean in to a conversation, as opposed to lean back. Just like a racecar driver notices how many seconds a turn is, when there’s an indent in the road, when the brakes are glazed and the tires need to warm up without having to look at them.
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.
I first heard this question from Morgan Housel quoting a Navalism (for the uninitiated, that means has its source tracing back to the one and only Naval Ravikant). And it makes you think, that in the multiverse, where each version of you lives a different life and makes different choices, what would stay constant?
These are things that are not attributed to luck. And as Morgan mentioned, “those are the things you want to focus on in life.” When predicting the future, many try to predict what will change, but the best bets with long time horizons are on those that don’t change. Things that aren’t attributed to luck. Or chance. In this world we live in, you’d be quite surprised the number of small, accidental decisions we make that lead to life-changing events.
Like you being 10 minutes late to a party meant that you somehow just showed up at the same time as your future spouse. And it was because of that, that led you to have a two-hour long conversation with him/her. Otherwise, you’d have spent the entire party hanging with your college friends.
Or because you forgot to bring your umbrella on a day it rained, it made you run into a hotel for shelter, where you stumbled upon the investor who led your Series A round. Because he/she too forgot to bring an umbrella.
Of course, I could play hypotheticals forever. Although I find it’d be a fun exercise to really examine how much of your most life-changing moments were due to serendipity.
As someone who makes their living on attempting to predict the future, that means we have to go back to first principles. For instance, human nature. Reid Hoffman’s framework that all great consumer products tap into one of the seven deadly sins. Something that despite innovation is timeless. Anecdotally, I do find some of the greatest investors — LPs and GPs alike — to be avid students of history, philosophy or psychology.
“Email is a wonderful thing for people whose role in life is to be on top of things. But not for me; my role is to be on the bottom of things.”
In life, while catchy and interesting and the talk of the town for that brief moment, sometimes it’s better to get to the bottom of things than to stay on top of things. After all, you only have so many letters on your tombstone.
The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. 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. I’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.
My friend told me recently, that in the hallowed halls of Zappos, there’s a line by the great Tony Hsieh:
“Just because you can’t measure the ROI of something doesn’t mean you shouldn’t do it. What’s the ROI of hugging your mom?”
Too often we measure by the business incentives and not our own intentions. Humans are social creatures. We enjoy the company of others. No matter how much or how little. No matter if you’re an extrovert or introvert. There’s a line in my buddy Lloyed‘s new book, From Grassroots to Greatness, that I absolutely adore — a lesson he picked up from surviving the Gulf War.
“Life’s not about the destination, nor the journey. It’s your companions who matter the most. The people traveling down the road with you.”
I hosted a 20-person dinner on Wednesday. The theme was simple. Good people, good vibes. The room was 100% investors — LPs and GPs. And at any other venue, with the concentration of minds we had, the conversation would also be 100% cerebral. Markets. Political dynamics. Investment opportunities. Tactics. And so on. Ok, maybe only 90-95% cerebral, but my point still stands.
So the question is how can I, as the host, diffuse the tension in the room, where people use their amygdala, more than their pre-frontal cortex. Or in less cerebral terms, how do I get people to just have fun?
And not to get too technical (unless it is of interest, then let me know), it was setting the stage and arming people with the ammunition to not regress to their normal habits. The former lent itself to explicit statements of good vibes. The latter was executed by an order of custom fortune cookies, with all the fortunes inside containing a fun fact from someone else who was present that day.
The result was a casual night of laughs and hugs underneath the canopy of the San Franciscan sunset.
A friend asked me the next day, “What did I get out of it?”
To which I simply replied, “There’s no ROI on a good time.”
Pennies and quarters
I came across this reel while doom-scrolling on Instagram. I’ll try to find it, but at the moment forgetting the attribution. But the influencer posed the question: What’s the difference between 100 pennies and 4 quarters?
Weight.
The sum of each set equates to a dollar. But if you were to put 100 pennies in your left pocket and 4 quarters in your right, you’ll feel the weight on your left side. And in this analogy, they’re worth the same, and that there are some people who have value but are not worth the weight. Not everyone who has weight is worth carrying.
So, what?
In the age of social media (which in fairness has very much gone off thesis from its original intentions), the number of friends one has or followers or subscribers seem to matter a lot more than the quality of those relationships. Similarly, in the metropolitan world, the number of cards your Rolodex can unfurl seem to take priority over true friendship. In fact, there’s a whole phenomenon called the strength of weak ties.
I don’t think that’s right. Is there ‘value’ in knowing a lot of people? Sure. But life isn’t about numbers and stats — how much you make, or how big the deal you just struck was. In fact, the only numbers that’ll be on your gravestone will be the day you were born and the day you died. That’s it.
The sad truth is more and more people in modern society feel lonelier and lonelier. Hell, there’s plenty of literature on how many of the world’s top celebrities — in other words, some of the most followed / subscribed-to people in the world — feel incredibly lonely. And frankly it’s on overoptimization of what can be measured, and forgetting about what makes us happy, joyful, content. And spoiler alert, for all the economists and statisticians, it’s not utility points.
In closing
And so when my friend shared his adventures at the Zappos office with me, which I’ve never been to, now I really want to.
So, until the next, be kind, stay awesome, go tell someone who’s made an impact on your life, thank you, and give that person a hug. You don’t have to wait till Thanksgiving to do so.
#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.
The most provocative part was when she posed the question: If you need an app to make friends, is that a negative signal?
The solution, in her words, “the long term winner here is likely to be… interest-graph social networks.” Furthermore, “platforms that give people an ‘excuse’ to gather, either IRL or digitally” are immensely powerful. Where friendship is a byproduct of usage but not the main or sole purpose of being on these platforms.
I agree that dual-purposed social networks and platforms are a wonderful solution, but, and I may be biased, I don’t think it’s the only solution.
As a former power user of networking or friend apps like Shapr and Lunchclub (yes, I used an app to make friends), I’ve made some great friends via both of those platforms. But at the same time, I was an early user for both. Both had yet to be widely adopted at the time.
For Lunchclub, I was using it at a time when everything was in-person, and you only had the option to meet people on Fridays at 2PM or 5PM at either Sightglass Coffee on 7th Street or Caffe Centro in South Park in SF. The latter unfortunately closed recently. And that was it. There were no other options. I had often joked with friends that as you were meeting your friend match that week at Sightglass, you would be sitting next to the person you would match with next week AND the person sitting five feet over would be who you matched with last week. It was a tight community, even if it was an unintentionally designed community. A group of hackers, early adopters, investors, and people just doing cool things.
Then, as Lunchclub pursued scale, quality declined. And as Olivia shares in her thread above, bad actors ruined the experience altogether. The same was true for Shapr. For Clubhouse. Just to name a few.
But dating apps nailed it. They’ve reached widespread adoption. Olivia postulates it’s because they offer data points and filters that you can’t find anywhere else. For instance, who’s single. She’s right. But there’s another reason. These apps promote interest in others. Or amplifying inherent motivation to be on said apps.
Let me elaborate.
Be interesting and interested
I’ve written about the above line before. Here. And here. And likely a few other places that’s escaping my memory at the time of writing this piece.
The thing is most platforms promote being interesting. The heavy profile customizations. The ability to share your own thoughts. Platforms that incentivize you to go from a consumer to a creator. A lot of it is about me. Look at me. Look at how cool I am. How cool my life is. The strive for perfection.
How can I ever be like the person I’m following? My life is nowhere near as awesome as her/his is. Most social platforms prop users up as a point of comparison.
All that to say, there are a lot of apps that help you be interesting, but not enough that help you be interested. The latter takes work. There’s a line that Mark Susterrecently shared on a podcast, and I love it! Citing the late Zig Ziglar (which by the way, is an awesome name), Mark shared, “People don’t care how much you know until they know how much you care.”
I want to underscore that line one more time.
“People don’t care how much you know until they know how much you care.”
It’s why I love my buddy Rishi’s recent piece on how to build and maintain meaningful relationships.
In Rishi’s essay, he shares that there are three levels to doing your homework — each deeper than the last — and show that you care:
Level 1 – The Basics: LinkedIn, Common Connections, Google, and Company Website
Level 2 – Digging in: Social Media
Level 3 – Going Deep: Podcasts, Writing, YouTube et. al
The purpose isn’t to be all-encompassing, but to show that you care for the human sitting across from you. It’s the intention that matters.
The late David Rockefellerbuilt prolific Rolodexes to show that he cared. In fact, it’s cited that his handwritten notes on others stood five feet tall and accounted for 100,000 people. Alan Fleischmannonce wrote in reference to David Rockefeller that, “If you were so fortunate to be a fly on the wall for any of his countless meetings and interactions, you would hear him inquire about the smallest details of his guest’s life, from a child’s ballet recital to a parent’s recent health concern. Rockefeller’s interactions were said to be ‘transformational, never transactional.'”
And it’s also the small things that matter.
In closing
The reason why I think Lunchclub was so popular in the beginning is in two parts:
The platform reduced the friction — the back-and-forths — of scheduling. They gave you two times, and you either made it or you didn’t.
The platform’s early users were innately curious individuals. When I was invited on the platform, my friend pitched it as, “I’ve learned so much from the people I met.” And my friend was and is already one of the foremost subject-matter experts in her field. The same was true when I began using the platform. People spent more time asking questions than talking about themselves. In fact, in many conversations, it’d be a battle of who can delay talking about themselves more than the other.
People were simply interested. There was no agenda. And no agenda was the best agenda. No one was trying to peddle anything to you. No one was trying to ask you for money or intros. People were the ends in and of themselves, and not a means to an end.
All in all, while there are incredible platforms that help you build friendships through interest and hobby alignment, I do believe there is room for a friend app for the curious. Or at least to help you be a really good friend.
So if you’re building something there, ring me up. That said, no matter how great technology is, with AI and all, every great relationship still needs that human touch. AI and platforms and apps might be able to get you 90% of the way there. But if you don’t complete that last 10% trek, 90% is still incomplete. For those of you reading who are American football fans, running the ball 90 yards from one endzone is still an incomplete. It’s still not a touchdown. You need to run the full 100.
If there’s anything to take away from this blogpost, it’s to be both interesting AND interested. Emphasis on the latter.
And in case you’re curious as to how I approach caring, these might be helpful starting points:
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.
