Category: Ideas/Creativity

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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 — 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.

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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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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2023 Year in Review

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

  1. The Science of Selling – Early DPI Benchmarks — One of my favorite lines from Jerry Colonna’s book Reboot is: “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.
  2. 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.
  3. 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.
  4. 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.
  5. 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

  1. 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).
  2. The Non-Obvious Emerging LP Playbook — Stay tuned for more content on this front!
  3. 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.
  4. 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.
  5. Five Tactical Lessons After Hosting 100+ Fireside Chats — I’ve a feeling this one won’t age well, but hell, maybe it ends up being like the #3 spot on giving thanks. Time will tell.
  6. 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!

Photo by Polina Kuzovkova 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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How to Make People Feel Special at Events

gift, present, christmas, happy, holiday

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 every time 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.

  1. What if we only did one event per month? If so, what would that look like?
  2. What if we only did one every quarter?
  3. 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.

  1. If I had to host an event for just one person — just one — what would I do to make it an unforgettable experience?
  2. What would need to change if I did so for a four-person dinner?
  3. A six-person dinner?
  4. What about a 10-person event?
  5. What about for 50 people?
  6. For 100?
  7. 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.

Photo by Kira auf der Heide 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 #80 How I Balance Time

time, clock

A friend trapped in his own tumultuous schedule recently reached out to ask how I seemingly effortlessly manage my bandwidth. For starters, I try, but even I get swamped. And I’m sure people I’ve worked with closely can corroborate. So if anyone has a better way, I’m all ears.

That said, as I mentioned, I do try. And naturally, that means I think about balancing my plate a lot. From shower thoughts to systems to keep me accountable. I’m going to share below the four things I shared with him, in hopes you’ll find some use for your own life here.

  1. I have a whiteboard in my shower. (Although, you might remember I mentioned this before.) In a list format in the top right corner of the board, I write down everything I’m involved in, especially the ones that require my attention. This way, everything is always floating around somewhere in the back of head. And when I shower, I take the one I’m most excited about ideating and just let the kids run wild in the attic.
  2. I like asking myself the question: What would I do if I knew I would fail? And subsequently… what skills, relationships, and experiences can I gain that would transcend the outcome of the project itself? With those two questions, it helps to take the emotion out of the equation and consider it rationally. Which helps in arriving at a decision that I won’t regret. And naturally since I have a pretty high bar with what I choose to embark on, that does mean I say no to a lot of things.
  3. Work with people who are as passionate or more passionate than you are about the project or subject matter. You also want to work with people whose passion is independent of yours. For instance, if they’re only doing a project ’cause you’re excited about it, the lack of internal motivation, I’ve found, to be draining over time when I work with someone who isn’t intrinsically motivated to put in their all. It also ensures that if on an odd day out, I’m just 30% as motivated as I am usually, they come in with at least 70% of their motivation. And as long as the collective motivation at any given point in time is greater than 100%, we keep working on it.
  4. Lastly, I categorize activities and projects by how often something requires my attention. Some things require my attention daily. Others weekly. A handful of others biweekly. Or monthly. Or quarterly. A few annually (like taxes, ughhh). And at any given point in time, I will have no more than two items/projects per bucket. For instance, I will have no more than two pressing things that require my attention daily. And so yes, I’m context switching. But not nearly as much as one might think. The caveat is that when an activity becomes muscle memory and requires very little thinking to execute (i.e. exercise, brushing your teeth, showering, journaling, or so on for me), then that activity/project no longer counts toward its respective bucket.

Photo by Jon Tyson on Unsplash

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

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

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

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#unfiltered #78 The Gravitational Force of Accumulated Knowledge

apple, gravity, newton

You can’t always be the fastest or the brightest or the most talented. For the most part, anything that can be measured with a metric, or put on a business card or a baseball card — anything with an absolute ranking — is not something you can always control. You can be the fastest 100-meter dasher in the world today. But tomorrow, there will always be someone who’s faster. Today, you can be the youngest founder who’s raised venture capital. But tomorrow, someone will outdo you. Today, you can sell the most Girl Scout cookies. But tomorrow, someone will outsell you. The Guinness World Records is proof of that. You get the point. Because you’ll be in fashion one day, and out the next.

But if there’s anything I learned from hanging around the dragons and phoenixes — all pen names for perpetually and persistently world-class individuals, it’s that there’s gravity in being a voracious consumer of content. In being a voracious curator of what one feeds their brain. Information diet or fitness as one of my friends calls it. Being the most knowledgeable — or the pursuit thereof — has a longer shelf life and a half life than all other phenotypical isotopes. Or my fancy schmancy way of saying, all the other titles one can earn in their short lives.

It also happens to be closest pursuit where one unit of input roughly equals one unit if not more of output. For instance, to be the fastest sprinter, one extra hour of practice doesn’t consistently yield one second off your personal best. But if you’re regulating your content intake algorithm, for instance reading books, and not doomscrolling on TikTok, one extra page read is more often one more unit of knowledge you can apply in the future. Or if you’re asking good questions, one more coffee chat yields you another year or two saved of mistakes you could have made in your craft. As such, one should spend time reading, listening, watching and asking.

I spent the past weekend tuning into one of my favorite talks by Bill Gurley. (I knowww……. It really took me this long to actually write this essay.) In it, he shared that one should always “strive to know more than everyone else about your particular craft.” He goes on, “That can be in a subgroup. What do I mean by that?

“Let’s say you love E-sports. Let’s just say you’ve decided multiplayer gaming E-sports, like, this is it for you. You grew up gaming, “I love it.” All right? Within the first six months of being in this program you should be the most knowledgeable person at McCombs in E-sports. That’s doable. You should be able to do that. Then, by the end of your first year you should be top five of all MBA students, and, hopefully, when you exit your second year you’re number one of any MBA student out there. It doesn’t mean you’re the best E-sports person in the world, but you’ve separated yourself from everyone else that’s out there. I can’t make you the smartest or the brightest, but it’s quite doable to be the most knowledgeable. It’s possible to gather more information than somebody else, especially today.”

It so happens to be why VCs ask about your previous experience before starting the company. It’s why they look for passion. It’s why VCs ask for you to show that you have spent time in the idea maze. And it’s why the goal of a pitch meeting or any meeting with someone you hope to impress is to teach them something new. They’re all proxies for a founder’s rate of learning. The rate that one acquires knowledge is often directly proportional to the rate of iteration.

At some point later in the same talk Bill Gurley does above, he says, “Information is freely available on the internet. That’s the good news. The bad news is you have zero excuse for not being the most knowledgeable in any subject you want because it’s right there at your fingertip, and it’s free, which is excellent.”

It’s true. There’s a lot of things out there on the internet. But with anything that is known for its volume, there is much more noise than there is signal. And sometimes the best approach is to find the smartest people or most referenced and most peer reviewed sources. So while there is a world out there behind covers and a .com address, sometimes the best thing to do is ask.

Page 19 thinking

Seth Godin shared something recently I wish I had heard sooner — page 19 thinking. It was in the context of compiling an almanac — a compilation of world’s greatest thinkers about the climate crisis. When Seth and the team first started off with a blank page, they knew that “in the future there will be a page 19. [They] know that it will come from this group, but [they also knew] there [was] not anyone here who [was] qualified.” So, to resolve that dilemma, someone had to ink the first paragraph of page 19. Then, that person would ask someone else to make it better. And then, that someone else would ask another. And it would go on and on until page 19 looked like a real page 19.

What made this approach special was that ego was checked at the door, and people were empowered to co-create the best version of that work. Seth went on to share, “But once you understand that you live in a page 19 world, the pressure is on for you to put out work that can generously be criticized. Don’t ship junk, not allowed, but create the conditions for the thing you’re noodling on to become real. That doesn’t happen by you hoarding it until it’s perfect. It happens by you creating a process for it to get better.”

In the world on Twitter, the above goes by another name — build in public.

One of the greatest blessings in writing this blog is that I get to ask really smart people a lot of questions. While a lot of knowledge exists behind two cardboard slabs, or these days, in a six-letter, two-syllable word that starts with ‘K’ and ends in ‘E,’ the richest concentrations of insight exist in gray matter.

If you’re a founder or someone who’s embarking on a new project, there’s a saying I love, “If you want money, ask for advice. If you want advice, ask for money.” Ask people to pay you or to invest in you. You’re gonna get a plethora of feedback. Feedback that comes in flavors of noise and signal. But it’s up to you to figure out which is which. Nevertheless, that rate of learning, assuming you’re out asking, building, asking, and building some more, compounds.

In closing

I’m not saying you should only read books or only talk to experts. I’m saying you should do both. Be relentless in your pursuit to learn. As Kevin Kelly once said, “Being enthusiastic is worth 25 IQ points.”

Luckily, knowledge also happens to be one of the few things in life that no one can take from you.

Photo by Priscilla Du Preez on Unsplash

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

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

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

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Three Lessons For Creating Unforgettable Experiences

games, playing, child

As those close to me know, over the past few weeks, I’ve been knee-deep in some new projects. Projects I haven’t been this excited to produce in a long while. One of which is around experiences.

At the same time, as friends and long-time readers of this humble blog know, I am no stranger to the world of social experiments and experiences. I still don’t have a great catch-all term for it. They’re not just another set of “events.” Events just remind me of the same conference, fireside chat, or happy hour playbook. But I try to take my events a step further. So, naturally, given my fascination around building experiences, I walk hand-in-hand with both psychological research and game design. The former of which I share a bit more in previous blogposts than the latter.

So, I’m going to dedicate this essay to three of the lessons I picked up in the latter.

  1. Create experiences that optimize for people who know no one else there.
  2. Don’t confuse complexity with depth.
  3. A great event is great not due to the event itself, but because of the story one gets to tell again and again.

1. Create experiences that optimize for people who know no one else there.

I had always had this somewhere in the back of my head. To design experiences where no one was ever left out. But when I caught up with a friend recently in New York, he codified it into what it is today. As someone who runs a design studio that builds immersive experiences in New York, he spends most of his time building experiences for strangers. And while friends may visit his exhibits together, the vast majority of his attendees do not know anyone else.

Take, for example, happy hours. Most happy hours aren’t designed for the person who knows no one. Usually the event itself is fairly laissez-faire. Most of which, the hosts don’t actively try to connect attendees. And so if you show up at a happy hour and the host is too busy to intro you to anyone, unless you’re an outgoing person, you’re likely standing near the edges, hoping to jump into a conversation if any group will let you. This often leads to events where people leave early and form cliques. It also optimizes for early birds, rather than the fashionably late.

Tactically, it’s creating excuses for people to jump in conversation. While not a problem for outgoing individuals, I need to empower everyone, including shy introverts, with tools to start conversations, where I and/or the experience shoulder the initial responsibility and blame to start conversations. That could be with customized fortune cookies where one is supposed to read their fortune to someone else. Or empowering people with a mission or an ask greater than themselves. For instance, to over-simplify it a bit, “I’m trying to put together a small group of everyone who’s wearing glasses tonight. Do you mind helping me find out all the names of the guests who are wearing glasses?” Or “I’m trying to resolve a debate with my co-host. Pineapples or no pineapples on pizza. I’m all for pineapples, but she isn’t. Can you help me find more allies?”

2. Don’t confuse complexity with depth.

This is unfortunately a fallacy I often find myself spiraling down the longer I’m given to ponder. And I lose myself in intellectual complexity.

Many years ago when a couple friend and I first decided to host an escape room in a mansion over three days and two nights, the greatest question we had was: How do we create an immersive experience over multiple days? And retain that level of immersion throughout? I thought, hell, what if we created a brand new language for the event. One that all guests would have to learn and practice throughout the event. We’d ease them in slowly, but the biggest puzzle could only be solved through adequate mastery in this new language. This easily gave me the greatest injection of dopamine when planning for the event. And I went deep, talking with linguistic professors, studying how Tolkien created Quenya, and how Cameron and Paul Frommer created the Na’vi language.

It was truly interesting to me and to many of my friends. But unfortunately, through user testing, to most others, while interesting to hear its backstory, was not fun to practice. I had ended up developing it to a level to where it departed from its English roots to resembling language of Scandinavian origin. Because of its complexity and how there were more guests who were English speakers than speakers of this new language, immersion broke almost instantaneously.

The great Mark Rosewater once defined interesting as intellectual stimulation and fun as emotional stimulation. While they’re not mutually exclusive, it’s important to not confuse the two.

There’s a great Maya Angelou line that I, like many others, like to reference. “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.” And it is no less true for gamified designs. Emotional satisfaction often runs deeper and longer than intellectual satisfaction. The former has a greater chance of becoming a “core memory,” to borrow from the brilliant minds behind Pixar’s Inside Out, than the latter.

I was lucky to learn this lesson from one of the greatest designers of card games alive today. It was on a call earlier this year, where I was telling him about all the awesome bells and whistles I was planning on implementing for an upcoming experience. And I asked what he thought. To which, he responded: “Kill all complexity. Complexity is not a substitute for depth. Rely on your audience for depth. The more borders, the harder it is enjoy. Too few, it’s chaotic. Find the absolute minimum number of borders.”

The goal of creating systems is to create opportunities for serendipity. To create opportunities where people can dive deep. Not to force people to take the plunge when they may not be ready.

His advice just happens to rhyme with a quote I’ve always kept somewhere in the back of my mind, but now sits on the wall above my PC.

“Your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” — Sanderson’s First Law of Magic

3. A great event is great not due to the event itself, but because of the story one gets to tell again and again.

Under the ambiance of MarieBelle, which I still so fondly remember the moment my friend told me this, she said, “A great event is great not due to the event itself, but because of the story one gets to tell again and again.” It’s the truest definition of surprising and delighting. She was someone who used to work on the Dreamweavers team at Eleven Madison Park when Will Guidara was still there. As such the above lesson was a page out of Will Guidara‘s book Unreasonable Hospitality, whose best known for how intentionally he took front of the house hospitality at 11 Madison Park, one of the greatest restaurants in the world. 4 stars on New York Times, and 3 Michelin stars. He also happened to be the person who conceived the Dreamweavers team there. Just to give you an idea of how seriously they take their roles…

First off, the core of the event itself — the meat, the protein — has to be great. If it’s a tofu burger, it better be a damn well-marinated fat slice of egg tofu, double-fried to perfection. To Malcolm Gladwell, that’s the meal.

And only once you have it all, what’s the cherry on top? What’s the candy? Why would people want to talk about it? For events, that’s:

  • Delivering surprises — gifts and/or experiences they do not expect
  • Transferrable pieces of knowledge — insights, frameworks, or trivia knowledge that are useful even after the event
  • Meeting great people WITH great stories — “Did you know that [so-and-so] did X?” And for this to happen not just opportunistically but at scale, finding ways to help people share stories of vulnerability or of adventures that have yet to grace any public media is key. The easiest way is through questions. The slightly harder way is through a set of triggers where it makes sharing such a story natural.

In closing

I am, as always, a work-in-progress. And with the events I’ll continue to host this year, I’m going to learn more. And in time, be able to share more of my lessons, trials, and tribulations in this journey. In hopes, this will aid or inspire you on your path.

Photo by Holly Landkammer 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 #75 Why I Write Long Form Blogposts

typewriter, blog, write

This past Wednesday, I was having lunch with an artist-turned-VC. And as you might imagine, we had to cover every topic at the intersection of art and startup investing. But of all the ground we covered, one stood out — content creation.

She’s on the Gram, LinkedIn, and everything in between. (Although surprisingly not on Twitter.) But to help her focus, she uninstalls those apps on her phone. Otherwise, she says she’ll end up “doomscrolling.” I get it. In fact, many of my friends and colleagues have shared similar things as well. But…

I’m weird. At least among my friend group, I’m really weird. I’m terrible at social media. I’m an 80-year old stuck in a 27-year old body. At least on the social media front. I find it so hard to keep my attention on social. In fact, I schedule ten minutes three times a week to hold myself accountable to be on LinkedIn and Twitter.

So, when it came to sharing my thoughts and learnings publicly, it was a pretty easy decision. Of course, I eventually came to self-rationalize it as the ability to own my own piece of virtual real estate, but there are three more reasons I chose blogging rather than tweeting or social posting.

1. I write to think

I’ve written about this before so I won’t elaborate in length on my own rationale here, but share a few examples of others also holding it in high regard.

There’s only so much you can flush out in just 280 characters, or over any short post. And while some of my thoughts fully flushed out may only be that long or less, not having that restriction gives me peace of mind to not hold back.

One of my favorite George Orwell lines happens to be: “If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.”

On that same wavelength on writing, Jeff Bezos makes Amazon execs write six-page memos. In most companies, team members often resort to PowerPoint presentations. Take anywhere between five and ten slides. Maybe less, maybe more. It’s much less thought out than a six-page dissertation. As Bezos says, “The reason writing a ‘good’ four page memo is harder than ‘writing’ a 20-page PowerPoint is because the narrative structure of a good memo forces better thought and better understanding of what’s more important than what.”

Equally so, it’s the same reason the best investors write memos for their investment decisions. My favorite public ones are Bessemer’s, which encapsulates much of their thinking at the time in amber. Turner Novak also turned his ability to write great memos to eventually raising his fund, Banana Capital. And the great Brian Rumao writes memos not just pre-investment, but also in his post-mortems where he gathers his learnings.

While I won’t go as far as to comparing myself to the afore-mentioned, I do find great pleasure and great learning from putting words on paper.

2. Longer feedback loop

My writing is more often a form of self-expression, self-curiosity, and self-discovery. So, unlike a product manager or founder who’s relentlessly testing and iterating on feedback, I enjoy longer feedback loops. I may start another content engine at some point that is for a particular audience, focused on feedback and iteration. But this humble piece of virtual estate will stay me. With no algorithm conditioning my attention span and yearn for external validation. That’s not to say I won’t ever (or have not ever) written things that you my awesome readers want, but it is only at the intersection of what you want and the what I enjoy writing about and asking others about that mint content here.

I also spend a lot of time thinking about audience capture, a term Gurwinder brought to my attention in an essay he wrote about Nikocado Avocado, which I also touched on in an essay I wrote near the end of last year.

I’m reminded by something Gurwinder wrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:

“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”

3. The impermanence of social media

Most things on social media are ephemeral in nature. It’s designed to capture the moment, but not chronicle the moments. On Twitter, you can only pin one tweet. On Instagram, you can pin three. And on LinkedIn, only three are visible on the featured carousel, and include, five max before it takes you down another layer of friction to discover more.

There’s a level of impermanence which makes thoughts feel whimsical rather than evergreen. To use a phrase I recently heard Tim Ferriss use, the “durability of the signal seems to wane so quickly.” And that made my thoughts feel cheap.

That’s not to say every post I write has their weight in gold, but the searchability and the evergreen nature of my favorite blogposts (saved in my “About” tab) are the reasons I keep most of my thoughts here.

Photo by Fiona Murray on Unsplash

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

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

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

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#unfiltered #74 What If Events Were Story Arcs?

castle, story, boat

“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”

That’s the arc of every great story in the words of Viola Davis on one of my new favorite interviews with Sean Evans, where she shares the secret to the hero’s journey.

In the world post-pandemic, people crave connection. A desire to go from URL to IRL. Everyone lost those years. Something everyone from a first grader to a college student to a young professional entering the workforce to a retiree could relate to. And in 2021, there was a re-emergence of events. Well-intentioned and well-founded. We had conferences, coffee chats, happy hours, fireside chats, oh, so many happy hours, panels, tech weeks, and… did I mention happy hours?

Most events out there are a time and a place for a collection of people. They’re static points in time. Not even counting the full spectrum of event planners, many of the best event planners spend tons of times on what makes events special, but change more about the small bells and whistles of an event than the overall flow. There are very few who take leaps of faith. Even less true for the vast majority of events, where events feel more of an afterthought than something that is designed to start or end a chapter in your life.

As such, everyone found themselves left with a goodie bag including a surplus of events, a lack of focus and attention, and a lollipop of exhaustion.

So, I had a thought last year, greatly inspired by my team at On Deck Angels. Instead of trying to host an event a month, what would need to change if we could only do one event a year? What would we have to do? Hell, extrapolating further, what if we only did one event every two years? Three years? Every Olympic arc? Which led to the thinking around, what do we need to do to make this the most memorable event that anyone has ever been to.

You see, I’ve hosted and co-hosted small and large-scale social experiments, but it was always for an audience who proactively and voluntarily signed up for. They were willing to do things outside the ordinary. But could I apply the same learnings to events for really, busy people who crave intellectual challenges, and who have been to so many events, they might be jaded?

So, below was and continues to be my collection of governing thoughts around answering that question, which will only grow and refine this year. In the theme of my blogpost last week, the below may be messy. Disorganized. Chaotic, even. Hope not, but possible. You’ve been warned. But I do hope that you might find at least one of the below frameworks useful.

Metrics for success

Every event needs a North Star. When planning the Angel Forum, as well as future events, below are mine.

  1. Attendees go on a hero’s journey, revisiting Viola Davis’ words above. In other words, character development. The event should create opportunities for growth within the event itself.
  2. Every attendee continues to and is motivated to build friendships (as opposed to networking and purely transactional connection) after the event. If the event itself is the only reason for people to connect, but it does not give people incentive to after, it’s a failure (in my books).

For now, that means, not only the speakers and the presenters need to be curated, but also each and every person on the guest list. I have yet to figure out how to customize such experiences at scale, where each person has wildly different goals.

Narrative frameworks I use for events

To dig a level deeper, here are my frameworks for execution:

  1. Surprise and suspense — Surprise is when you relay information that the audience does not expect. Suspense is when you relay information that the audience is expecting, but does not know when it’ll drop. Suspense is how you keep attention. It raises expectation, but knowing when to deliver the news helps with creating a reality that meets or beats expectation. Surprise is, on the other hand, purely for creating alphas in this expectation-versus-reality model. It’s the main driver for overdelivering on a seemingly smaller, but still powerful promise. To do so, I find George Loewenstein’s 1994 paper on the psychology of curiosity super helpful. More on how the five triggers to curiosity influenced my thinking here.
  2. Candy versus the meal — A Malcolm Gladwell framework. Effectively, how people think and what people actually talk about are quite different. Candy is what people talk about. For example, if I were to talk about the recent Avatar movie, I’d talk about how amazing the motion capture and the CGI was. And in doing so, I’ve spoiled nothing. It tells you nothing about the plot, but it’s exciting to talk about. On the other hand, the meal is how people think. It’s the whole package, the whole story. The meal has to be well-worth the visit, but the candy is what gets people excited. More on that in a previous essay I wrote here.
  3. The audience must understand the rules of magic — This is a combination of the thoughts of Malcolm Gladwell‘s framework around tools and Brandon Sanderson’s three laws of magical systems. Give the audience tools to use at the very beginning of the event. It could be a framework for how to think about the event and every activity in between. It could be physical tools that they will employ throughout the event. And once you do, make sure your audience knows how to use those tools. Test them. Give them small, but easy case studies and questions. Make it easy. Don’t put them on the spot. And by completing that test, that satisfaction and joy will help motivate them to use it more later. As Sanderson’s first law of magic goes, “your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” More on my thoughts on Sanderson’s laws here.
  4. Plots — Like any good story, the narrative is governed by plots. The plot must thicken and build towards a climax. And it must be resolved by the end of the event. Leave little in the main plot to chance, but leave room for each guest to discover something extraordinary. Maintaining a minor amount of stress and uncertainty, while sharing examples and reminders of being open-minded to new experiences, goes a long way. Only after stepping outside one’s comfort zone can one grow.
  5. Always use the audience’s time in a way that does not feel wasted — Inspired by one of the greatest writers of all time, Kurt Vonnegut. I forget which lecture he did that I learned this from. But it’s always been a governing theme for what I do.
  6. End on an ending where the reader can imagine no other — No loose ends. Everything that is teased (whether the audience realizes it or not) needs to be resolved by the end. This might be a semi-controversial opinion among storytellers and creative professionals. But I’m biased. I like my stories to end with a bowtie.

In closing

As you might imagine, much of this is still incomplete. And I hope to share more as I continue down this path of exploration and discovery.

Photo by Artem Sapegin on Unsplash

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

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

Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

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v27.0

The Earth has once again gone through another orbit around the only star within four light years from us.

In the past version of David, I’ve published many blogposts. Yet one of the most continual topics that owns real estate in my mind is the idea of the 99 unsolicited, but more importantly, non-googleable (figuratively speaking) pieces of advice. I’ve already published two blogposts on the respective topics of entrepreneurship and VC. And am now compiling more and an additional set of life hacks. I imagine, at some point, I will for other areas of my life I want to spend mind space on. Asking questions. Hosting interviews. Events. LP stuff. Just to name a few.

In other words, I am on a constant search for tactical pieces of insight in the corners of both the internet and safely kept (often unwittingly) in the grey matter in 7.8 billion locations. Or simpler, I want to know what others know.

I was listening to a podcast featuring James Clear earlier this year. And in it, he said something I completely agree with. “Almost every idea you have is downstream from what you consume. When you choose who you follow on Twitter, you’re choosing your future thoughts.”

In an age that offers us a wealth of information and a million topics, posts, comments, videos, and algorithms that will distract us, it becomes ever more prescient to be a great curator. It doesn’t even have to be for others. At the very minimum, for yourself.

The amount of time I’ve scrolled through metaphoric cat videos on YouTube is appalling. And I realize that whenever I do, I face a dry spell of ideas. Luckily only briefly.

As of now, the world’s top social media platforms’ algorithms work against us. It surfaces us content we are likely to enjoy. Content that is high likely to reinforce our confirmation bias, as well as availability bias of the world. And the biggest problem with that is we are fed cousins of the same information rather than new, and possibly dissenting information that would challenge our beliefs. After all, these apps’ goal is to keep us on the platform. Not to close the app and do something meaningful with our lives. I’m excited for the day we get to build our own algorithms for consumption. But for now, it has to be more manual.

James Clear also goes on to say in the same interview when Tim Ferriss asked how he chooses which books to read. “First thing is you got to be willing to quit books fast. If you have baggage around finishing books, then you’re just going to be stuck and you won’t move on quickly enough.”

I’m guilty of the counterfactual. I’ve long prided myself on seeing things through. In fact, I still do. But at least on the consumption part, I’m slowing down my rate of learning. This year, I’m going to start measuring the number of books, articles, and podcasts I fail to complete, as well as the number of long form content media (i.e. books, movies, articles, podcasts, etc.) that have inspired an idea or an output. The goal is to optimize for learning and insight rather than completion.

Since this is the first year I’m measuring it, I won’t be able to measure the delta. But I’ll leave this encased in amber for David v29.0 and future iterations.

Doing things that are unteachable

My sixth grade teacher once told me, “David, you should be proud [she] copied you. That means you have something worth copying.”

I, like many others, spent the first 22 years of my life copying and learning from someone else’s or multiple people’s playbook. And often still do. The four years after I worked on being different. From the words of someone I look up to, “Be interesting and interested.” Where I put more effort into being interesting — doing interesting things, having interesting perspectives, asking interesting questions. I worked to create things worth copying. And when I started this blog, I followed that same ethos. I did and will continue to do my best to share my findings and takeaways. So that others won’t have to fall through the same potholes as I did.

At least, that was my belief until December 8th last year.

I hosted an event. An event I’ve never been more excited to host. An event where I was intentional about as many details as I could. And a byproduct of being in the flow state at least twice a week. While I’ll likely spend another blogpost taking a deeper dive on this topic, it occurred to me that events, just like any other medium of consumption — movies, books, podcasts, shows, and so on — should be stories. And every story has a beginning, a middle, and an end. But more importantly, every great story has:

  • An inciting incident — something that compels the protagonist to leave their current timeline to embark on something spectacular
  • A main plot (with sometimes multiple side plots)
  • Character development — the protagonist, as well as other characters, grow over the arc of the story
  • An ending where the reader (viewer or listener) can imagine no other (tipping my hat to Robert McKee)
  • And to use the reader (et al’s) time in a way that is not wasted (tipping my hat to Kurt Vonnegut)

To my joy, it was as great if not greater than expected. The feedback was phenomenal. In my excitement and post-event high, I shared with many friends, colleagues, and family about how I thought about the event.

And to my dismay, while most were happy for me, a friend told me:

“You’re built different. I could never do what you do.”

In subsequent days, two other friends told me the same.

And it reminded me of something John Fiorentino once said. “The things that are going to be valuable are the things you can’t teach or copy.” While I was initially dismissive of this corollary, I now realize there might be some truth to it.

So, how does that change the stories I’ll share here or anywhere? In the past few years, every time I do something new, there ‘s usually a voice in the back of my head that asks me, “How would you catalog this adventure on your blog? What would be the title of the blogpost? What kind of title works best for SEO?”

Going forward, I’m going to ask that voice to hush. Not to say I won’t share my learnings, but I’ll preface now that my future writings may not be written for search engine optimization. It’ll be raw. And from title to body, a truer expression of what I want to share.

So where do I go from here?

I’ve hedged to be fair my entire professional career. I’ve done tons, which on paper, seems like a lot, but I’ve never fully spent time immersing myself in only one thing. And nothing but one thing. I’m context switching all the time, which probably means I live 20-30% less of a day than a focused person.

So I’m going to have to take more risks. ‘Cause I’m starting to believe that in order to do something that cannot be copied, I’m gonna need to focus more.

Photo by Mike Lewis HeadSmart Media on Unsplash

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