Category: Life

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The Cure to the Loneliness Epidemic

lonely, alone

This past weekend, in my endless doom-scrolling, I stumbled across one of Olivia Moore’s amazing threads.

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 Suster recently 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.

Source: Rishi Taparia’s Building Relationships Through Research

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:

  1. Level 1 – The Basics: LinkedIn, Common Connections, Google, and Company Website
  2. Level 2 – Digging in: Social Media
  3. 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 Rockefeller built 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 Fleischmann once 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:

  1. 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.
  2. 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:

Photo by Lukas Rychvalsky on Unsplash

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

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

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My Ever-Evolving Personal CRM

The soul dwells in things and in people you cherish.

I don’t remember where I first heard that line. But it’s a line that resurfaces in my life quite regularly.

Building and, more importantly, keeping relationships alive is something I get quite nerdy about. Have always been nerdy about, and have personally made a few angel investments on this front as well.

A few friends and I literally spend a few hours riffing on topics like this. So when Obi launched my episode with him on the Frugal Athlete, it sparked a few more conversations about my Airtable CRM, which I thought might be helpful to share some additional context.

I will also preface that my goal of even keeping a CRM in the first place was not motivated by a fear of not remembering hundreds of names. My fear was not remembering that one friend who’s been a champion in my life.

What’s in the CRM?

So I have the usual table stakes I imagine most, if not all, CRMs have:

  • Name
  • Location
  • Email
  • Socials
  • Preferred medium of communication
  • How we met
  • Year we first met
  • Last time we chatted
  • Job title
  • Company
  • Past companies
  • Expertise
  • Things they like/dislike
  • Birthday

But the reason you’re here is not for the table stakes. You’re here for what I include that others may not. So let me share a few.

Chill Factor

This one is simple. Different people have different propensities to go deep. Some choose not to. For others, maybe we just don’t know each other well enough. But it’s a reminder to myself (just because I’m quite unfiltered sometimes) that not everyone I know is comfortable with being vulnerable. It helps me, especially for someone I haven’t chatted with in a long time, calibrate the tone of how I reach back out to them.

Why I’m useful to others

While most people track a person’s expertise, I also track how I can be helpful to others. Sometimes it’s my network. Other times, it’s the events in which I host. But also, my network (i.e. they want intros from me), or job opportunities, or advice in which I can impart in different functions/industries. In the world of being an investor, the most canonical question a VC can ask is “How can I be helpful?” Which in all fairness, is a good question showing one’s willingness to help. But if I have context already, instead of asking that every time, I can take it one step further and actually offer specific things in which I am helpful to them in.

My bucket list

One thing I learned very early on as someone seeking advice and mentorship is that one of the best ways of giving back is to follow up once you’ve actioned on someone else’s advice or suggestion. It shows you take their words seriously. And so as soon as I built my CRM, I decided to track everyone’s recs. And when I finally check off something on the bucket list, I know who to go back to and thank for the recommendation. For many, that comes as a welcome surprise.

It also helps me help others when people ask me to recommendations, be it book, restaurant, movie, tourist spot or otherwise.

Quotable moments

No screenshot here unfortunately; just because some thoughts have been shared in confidence. But if you’re a repeat reader here on this blog, you’ll know I love quotes. And I love collecting quotes. And naturally, any time someone shares a tweetable soundbite or a banger, I make sure it’s not lost to the cosmos. I may not share all of them, but when I do, I know who to give attribution to, but many of my friends have admittedly used my CRM and me as their biographer.

In closing

I don’t want to get too metaphysical about this. But my Airtable is less so of an automation or an attempt to outsource friendships, but more so, it keeps me honest. When my memory slips and fails me, my CRM reminds me of the little moments that make my friends awesome!

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 #83 There Doesn’t Have to be a First Place

medal, winner, gold, first place

I recently learned that in FISM competitions — competitions hosted by the International Federation of Magic Societies (if the letters aren’t in order, it’s because FISM is in French not in English), that the judges don’t have to award any prizes. Meaning if they don’t think any of the magicians and their acts are up to par, they don’t have to dole out a first, second or third place. And according to Simon Coronel, it happens quite often. The goal is simple. That winning first place should mean something. Not just because you’re better than the rest that day or that year, but that you really deserve to stand among the greats.

And it got me thinking. Are there other fields that should strive for the same level of rigor?

For instance, does an Oscar need to be awarded every year for each category?

Or an Olympic gold medal for each event every four? (Although a caveat to my own, if the rules change, like when in 2010, they banned male full-body suits when swimming at the international stage, then there should be a reevaluation of excellence.)

And there might be some years that the best prize awarded should just be a second place one.

Then there are other contests, where the number of prizes only seem to increase. In other areas, namely to join certain rankings organized by members of the press, you have to pay for your spot. The latter of which I have no experience in. But had heard of accounts from friends who have.

The truth is it’s not my place to rate the world’s greatest artists or athletes. But it does make you wonder that if the magic society can hold themselves to that high of a regard, why can’t the rest of us do so?

Once upon a note

As all good Asian children did, once upon a time, I learned to play the piano since I was five. One of many teachers and admittedly the one I was with for the longest happened to this sweet lady who taught her students out of her home. And every year, usually around the beginning of summer, she would rent out a hall and host a recital between all her students. Every student (and she had 30-40 students) — from beginning to master — would play one song.

The whole recital would last about 2-3 hours. And at the close, there would be an award ceremony. For each skill category, there would be a Best of Show trophy. And for everyone else, a participation trophy. When I was first started off and was quite bad, that participation trophy felt great, even if I was only playing Twinkle Twinkle Little Stars. I put it at the top of my shelf next to my bed, so I would see it every morning when I woke up.

Then 1-2 participation awards later, they had lost their luster. The Best of Show is now what I was aiming for.

For a brief period of time, that was my goal. And eventually I got it. But I remember when I finally got it, I wasn’t nearly as elated as I thought I’d be. ‘Cause that year my teacher decided that one Best of Show wasn’t enough. Three felt right to her. To be fair, I don’t know if she had over-ordered or just felt the need to give more out due to some parental complaints. But I remember receiving mine alongside someone who I knew made a few hiccups on stage. And even though I did the best I could have, I didn’t feel like I deserved it.

So that night, I didn’t even put the Best of Show trophy on my shelf.

A side corollary to angel investing

The greatest feature of being an angel investor (as opposed to being a VC) is that you can be opportunistic. Your fund size is your own liquidity. You’re not tied down to a mandate. Or a deployment schedule. And if so, self-induced. What it means is that you invest only when you see a great company and team. Anything south of that means you don’t have to. You don’t have to award a check to a founder if you don’t feel they’re deserving of a first place. And because of that, “first place” actually means something. Not only to the founders you invest in, but to you.

That said, playing my own devil’s advocate, much of early-stage investing is luck-based game. And it is foolhardy to attribute to skill when a large amount of variables is unbeknownst at the time of investing — be it asymmetric information, or market conditions, incumbent moves, or purely black swan events in the future. The latter few, you need to count on luck more than once. And luck purely defined as “uncertainty in outcome,” in the words of the great Richard Garfield.

Photo by Brands&People 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 #82 Sometimes The Best Thing You Can Have In Life Is The Best Partners

This past week, my friends were sending me one of the latest Shark Tank episodes (apologies for not finding a better fidelity video), asking me: Would you have invested?

https://www.youtube.com/shorts/7Yf2BrfC_ww
If this link dies due to copyright issues (since I haven’t waited till ABC puts out their original version), just Google “Shark Tank Eyewris”

But I bring it up not because I’m here to share what my thoughts on the deal, but because of a powerful lesson shared on Shark Tank’s Season 14 finale.

The best thing you can get in life is often to have the best partners. That’s true in business. That’s true in romance. And that’s true in life.

And yes, it’s also true in venture. As a founder, it’s not about who gives you the most money. Or gives your business the greatest valuation. Unfortunately, both are often vanity metrics, underscored in the 2020 and 2021 bull era. It’s about partnering with the right partners who can take you to the next stage. Partners who will keep you honest. Partners who will call you out on your BS. And partners who will tell you the things you don’t want to hear, who will have you do the things you don’t wanna do, so that you can be the founder you were meant to be.

In careers, it’s no less true. I’ve always looked at careers from the perspective of who can I learn the most from. It hasn’t always been the highest paying or the biggest brand. Frankly, it was easy to turn down both of the before if I didn’t feel like I would spending the next few years working with the best. Not only in terms of acumen, but also in how much they cared.

My friend Nichole Wischoff’s recent tweet echoes the same.

To think that one doesn’t need others to succeed, that’s foolish.

#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 #81 Against All Odds

sunrise, sunset

A few days ago, I caught up with an old friend from college. Amidst our conversation on how I was spending my time, he asked me, “Wouldn’t your time be more valuable helping the winners in your portfolio than the others?”

And I told him, albeit a bit more defensively than I would have liked, “Our brand is determined by our winners. Our reputation is earned by helping everyone else.” One of my better ad hoc lines, if I say so myself.

But more so, and I might be naïve in saying so, I may not get the most number of hours for sleep a night, but I will say, when I hit the bunk, I have the best sleep out of anyone you might know. And I do so because I know I’ve meaningfully touched someone else’s life. And by extension of them, indirectly, a few others.

Just because most startups fail doesn’t make each of their endeavors any less important.

Malia Obama once asked her dad, our former president what’s the point in working on climate change if the difference is so miniscule. That the world is burning. And what can one person do?

To which, Obama said, “We may not be able to cap temperature rise to two degrees Centigrade. But here’s the thing. If we work really hard, we may be able to cap it at two and a half, instead of three. Or three instead of three and a half. That extra Centigrade… that might mean the difference between whether Bangladesh is underwater. It might make the difference as to whether 100 million people have to migrate or only a few.”

In the world of startups, which isn’t exclusive to our world by any means, there’s a saying that people love quoting. Aim for the stars; land on the moon. And regardless if you hit the stars or not, aiming for it gets you the escape velocity to be extraterrestrial. In other words, it’s not always about whether you hit your goals or not, but rather… it’s the pursuit of lofty goals that gets you further than if you didn’t try in the first place.

I’m reminded of a great line by Dr. Rick Rigsby quoting his dad. “Boys, I won’t have a problem if you aim high and miss, but I’m gonna have a real issue if you aim low and hit.”

So, in this week’s short dose of optimism, don’t aim low and hit. Stay awesome!

Photo by Mohamed Nohassi 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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The Tale of Two Risks: Market and Execution

market, flea market, farmers market

Folks coming out of school and/or are still in school often ask me how they should break into venture. It’s surprisingly a timeless question. The goalposts change every era. And as the signal-to-noise ratio and regression line oscillates in bull and bear markets, young professionals chase a moving target.

That said, while my opinions will likely change when the facts change, as of now, this is my best proxy for a timeless answer. Market risk versus execution risk.

Let me elaborate.

Early in your career, you should take market risk. Bet where others are not willing to bet. Or have the same starting point as you do. If the starting line is even, it’s all about how much faster you can run compared to your peers. And if you can outlearn them, ideally because of internal drive and motivation, you’ll be the incumbent in the space in the future.

Execution risk is what you pursue as you grow. Your network, your expertise, and your experiences make you a more robust executioner. You’re an incumbent. You’re a juggernaut. There’s no reason to focus on this risk when you’re younger because you don’t have an unfair advantage here. In fact, you have an unfair disadvantage. Others more senior to you have a better network, more expertise, and have done more reps than you have.

Steve Jurvetson recently shared the only rule of business that is inviolate. “Take any company that is large or top three in their industry. They will never lead the charge to disrupt that industry.” He goes on to say, that even in recent years, Google didn’t fight to change search until OpenAI. Apple is innovative outside their core business, but never in their core business. So as a result, innovation needs to come from the bottom. People who are willing to take market risk.

Similarly, in venture, as a young VC, you need to build your own thesis. For as long as you are investing on the basis of someone else’s thesis, you are competing on execution risk. And every VC who’s older, wiser, and more connected than you are on that thesis will out-execute you.

So… the risk you have to take is betting on a brand new thesis. That no one else is pursuing. No one else is investing by it. And that… is market risk.

The above is no less true if you’re an emerging GP. Your fund lacks the resources, likely the connections, the experience, the talent, and the ability to out-execute your incumbent on your incumbent’s thesis. The solution is to just not play when they have the home field advantage.

It’s why thesis and the question “Why does another venture fund need to exist?” matter so much to LPs betting on new fund managers.

Photo by Kayle Kaupanger 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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DGQ 16: What is a story that you’ve told or have yet to tell where you either fight to hold back tears or fight to hold back giggles?

tears

Whenever I host fireside chats, I always ask three questions before the talk begins, usually a week in advance.

  1. What would make this interview the most memorable one you’ve been a guest for even two years from now?
  2. Are there any topics you don’t want to talk about? Or are sick of talking about?
  3. Are there any questions you have yet to be asked, but wish someone were to ask you?

On top of the above three questions , occasionally, I ask a fourth. Do you have a home run story that has gotten you a standing ovation in the past — privately or publicly?

The goal is simple. Despite hours of research and asking mutuals, sometimes I still can’t find anything that’s humanizing about my guest. And I know for a fact that all humans are imperfect. And that imperfection makes each person relatable. Just like when Neil Gaiman met Neil Armstrong. But recently, I’ve fallen in love with a new way to phrase the fourth question.

What is a story that you’ve told or have yet to tell where you either fight to hold back tears or fight to hold back giggles?

On my flight to New York recently, I watched a movie starring one of my favorite actors in the world, Tom Hanks, which inspired this question. And, subsequently this blogpost. A Man Called Otto. Inspired by Fredrick Backman’s A Man Called Ove. And I’m not ashamed to say, I cried during that movie. While Rotten Tomatoes may not give it the score I think it deserves, it was well-written and well-produced. Through it, I realized that powerful stories are powerful not because of how awesome the protagonist is. But by how relatable their weaknesses are. Their limitations. I’ll give an example… to avoid spoiling the afore-mentioned movie.

Spiderman isn’t awesome because he has mutant powers. He’s awesome because he’s prone to all the emotions and struggles, be it love, bullies at school, a horrible boss, and how he acts out against all of that. Spiderman’s much more relatable than a super billionaire who owns all the gadgets in the world or an alien from another planet. He’s just a kid from Brooklyn. Or Queens, depending on which Spiderman suits your fancy. And as Brandon Sanderson once said, limitations are more interesting than powers. Limitations make us human. And characters who exhibit humanness and still somehow overcome impossible odds are stories that are passed from generation to generation.

That said, storytelling, outside the realm of superpowers, is equally as true. In a world where appearance and social capital goes a long way, trying to be perfect, to look perfect, and to act perfect is a fallacy in the modern era. While we know we’re not perfect, as a society, we continue to strive for perfection.

After watching a lot of movies, and in my free time, watching acting lessons (FYI, would fail as an actor, but still find the craft fascinating.), I’ve learned we don’t cry when watching movies because the characters cry easily. We cry because the character is trying to hold back their tears. And we don’t laugh during a show or a movie because the comedian laughs easily. We laugh even more because they’re trying to hold back their own laughter. The narrators and characters we see are a reflection of who we truly are.

In many ways, if someone cries easily, it relieves the audience of the ability, some artists may call it responsibility, to cry. Someone, the actor or actress or character has diffused the tension already. But if they fight to hold back their tears, holding back the floodgates, we as the audience are more likely to cry in their stead.

Now I say all of this because I find most fireside chats and interviews unrelatable. Now it’s a product of many things. And I genuinely believe a plethora of individuals do have something powerful and insightful to share, but the stage needs to be ready for them. It’s rare for guests to drop some head-turning advice in the first 10 minutes. Which means… it’s up to both the host and the guest to hold the audience’s attention long enough, as well as create enough opportunities for the guest to shine. The above question, in my opinion, does both.

So all in all, going forward, rather than asking for a home run story, I will ask for stories where people are just people. And for stories that mean a tremendous amount to the people telling them. That they have no choice but to let even a little bit of themselves out emotionally.

Photo by shahin khalaji on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. 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.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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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