Tag: social experiment

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Poker, Event Design, and Vulnerability

poker

(FYI, the first three paragraphs, from a content perspective, are all ‘gotcha’ moments and are irrelevant to the lesson one would probably take from this blogpost. Feel free to skip to paragraph four if you don’t need the extra context.)

Yesterday, a good friend of mine invited me to an intimate event he was putting together for experts to share their insight around a particular problem in today’s society. If he’s reading this blogpost, he’s going to insist on the fact that I’m a co-host. A title I’m embarrassed to take on since he does 99% of the work of why this event is as thoughtful as it is every month he does it. But I digress.

At the very end of the event, my VC buddy who came, came up to me to ask for some advice. “David, I host these poker nights every month for about 30-40 people. But I would love your thoughts on how I can make this event format more engaging and also unique, like the way you host your events.”

Spoiler alert. I never gave him a good answer to that question. So, if you came for that answer, joke’s on you. Or if you really want an answer to that, DM me, and I’ll share my thoughts.

But what happened after was quite interesting. My buddy who hosted the event last week — let’s call him, Danny — posited that poker was a particularly bad activity to do for an audience of founders and investors. Why? Lying is not a practice investors want to encourage in the founders they’re backing. The worst thing that can happen in a VC-founder relationship is that you find out the company is dying when it dies because the founder couldn’t be honest with you sooner. You want a clear line of communication between investors and founders all the time, so investors can help you course correct if they see you heading down the wrong road. And poker is a game that encourages lying.

To which, I agree from the angle of VC to founder relationships. Even personally, I don’t jump in any investor-investee relationship if I don’t think that investee (be it GP or founder) cannot be honest and vulnerable with me in the moment or in the long run.

My other VC buddy — let’s call him, Josh — countered with the fact that yes, poker does encourage you to lie, but most people he plays with have a clear separation of church and state. They know that poker is a game. And as a game, the behavior that is exhibited under such rules stays in the game. What happens in Vegas stays in Vegas.

At the same time, while poker isn’t really the game to play to be vulnerable, Josh said that poker is a great environment to see how a founder reacts to stress. As well as, how they deal with the hand they’re dealt, figuratively and literally. You get to see if a person is risk-averse or risk-taking. Under what conditions? And when their competitors get aggressive, do they step up to the challenge or take a back seat. Do they spend time looking at their hand or analyzing their environment?

Again, also a lot of merit to what Josh said.

Then, ensued a bit of back and forth.

In my opinion, they’re both right.

In my experience, most founders don’t lie easily. While I haven’t done any market surveys if founders are more likely to lie if they play poker versus if not, I also believe that most invitations to poker nights among closed circles stay in closed circles. In the sense that most poker hosts pre-qualify if a person is a high integrity individual before they invite a guest to play poker. So in other words, a high selection bias.

People are more prone to lying or hiding facets of the truth when their ego is attacked. When something so core to their identity is questioned and put at risk. The higher the stakes, the more likely someone is to lie. In most poker games, and with sane people, the bets never exceed a meaningful portion of someone’s net worth. They’re not risking tomorrow’s dinner on the table.

Admittedly, in games where the primary adversaries are the other people present there, one is less likely to have opportunities to be vulnerable. Like poker.

On the other hand, in activities or games where the primary adversaries are themselves or the environment, there is no need to hold pretense. As such, people are more likely to be vulnerable. And have opportunities to be vulnerable. Like pottery, or glass-making, or maybe even golf.

That said, humans are creatures of comparison. We tell ourselves narratives that prescribe meaning to our actions and the actions of people around us. So even in the latter situations where the primary adversary is either themselves or the environment, you want the variation of proficiency levels to be low. In other words, each individual’s proficiency level needs to be as close to the median proficiency level as possible. Or what many will call, levelling the playing field.

For instance, let’s take painting. Painting is a skill where the dispersion of proficiency in the world is rather high. Some people exhibit the talent of Picasso or Georgia O’Keefe. Many others are happy with a decent looking stick figure. If the activity is art, one way to level the playing field is that everyone is blindfolded. Each person loses a sense that is quite crucial to their ability to produce great art. A handicap that instantly brings the variance very close to zero.

Take another example. Golf. Another sport where skill levels may differ drastically. One way to collapse the variance function is simply to have everyone swing with their non-dominant hand.

The goal here is not to only handicap the skilled, which may lead to passive aggressive discontentment. The goal here is to handicap everyone and help everyone divorce themselves from tying the result to their ego.

I’ve always optimized for activities and event formats that help people bond. If you search up ‘social experiments’ on this blog, you’ll see exactly what I mean. I love events that elicit curiosity, as opposed to competitive spirit. Maybe it’s to atone for my own competitive spirit. Knowing that if I have the chance to compete, I will. And well, sometimes, when I’ve set my goal on winning, I can be a misery to be around.

P.S. I appreciate all founders and investors who have invited me to poker nights. While I have played in a few, I can confidently say that I suck. I have a terrible poker face. 🙂

P.P.S. For my readers that are way wealthier than I am — you know who you are — I cannot afford your million dollar buy-ins at the table. That is just way too much funny money I do not have.

Photo by Keenan Constance 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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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 #44 Le Raison d’Etre for Social Experiments

social experiment, curiosity

Over the past few weeks, a number of people have independently asked me, “What do you hope to accomplish with your social experiments?” And “What are you hoping to solve through your social experiments?”

Usually when people ask, I say things like, “Helping the world feel a little smaller, closer, and a whole lot more meaningful.” Or “Helping strangers become friends in minutes.” While it’s all true, I came to that conclusion after I started. Yet, the real reason I started was simply out of curiosity. I didn’t have an end goal in mind. I didn’t have a hypothesis I was trying to prove. Frankly, I just had a yearning knowing I’d find answers, but not knowing what kind of answers I would find.

For the longest time, I felt pressured to give a reason. Particularly, one that was results-oriented. In a world, where outcomes speak for themselves, I felt that a genesis starting from pure open-ended curiosity wasn’t enough. The reasons I gave were less for others, but more for myself. This self-inflicted feeling of inadequacy. Infinitesimally small, but still lurking around.

Walter Isaacson‘s recent interview with Tim Ferriss led me to introspect once again. Known for his incredibly intricate studies on the lives of Steve Jobs, Leonardo Da Vinci, Benjamin Franklin, just to name a few, and most recently, Jennifer Doudna, he said:

“Be curious about everything. All walks of life. Arts, and sciences, technology, and the humanities. That’s what Steve Jobs did. He had one foot in the arts, another foot in technology, and he did not make a distinction between those two. That’s what Leonardo’s Vitruvian Man is about. It’s a work of art, and it’s a work of science, and he didn’t make a distinction between those two. And for Jennifer Doudna, she doesn’t make a great distinction between the life sciences and the humanities. And by being curious about all things, she’s about to see the patterns in nature.”

It’s funny that it took a message from someone else for it to resonate, no matter how many times I’ve told myself the same message. While I can’t even begin to compare my selfish curiosity to the greats of Doudna, Jobs or Da Vinci, but like them, I start from a state of open inquiry. I, a humble traveler, merely enjoy the meandering adventure my curiosity leads me on. As my French high school teacher used to say to us all the time, “Bon voyage!”

Photo by Joseph Rosales 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!

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#unfiltered #39 Five Lessons from Trying to Engineer Serendipity in a Virtual Environment

startups, spark, how to engineer serendipity, social experiments

Over the past few months, I’ve been slowly experimenting with how I can take Hidden Questions online, while not sacrificing the intimacy of the relationships it builds as well.

Hidden Questions started as a question game I played with friends and colleagues, which eventually expanded to other strangers. The goal of which was to deepen our friendship within minutes rather than weeks, months, or even years. In sum, a game where each person has to answer the question truthfully, but is not required to reveal what the question is. The catch is that if the person decides to conceal the question, they have to take a “punishment” (i.e. crazy hot sauce, disgusting foods, durian, Beanboozled jelly beans, etc.). Before they decide to or not, other participants can ask clarifying questions, as long as it’s not “Is X the question?”, and bet additional units of “punishment” if the answeree chooses to conceal the question. Of course, if the answeree does reveal, the people who bet will take the “punishment” instead.

Some references:

What’s changed?

After over 30 sessions in the past 3 months, a few things have been hotfixed since the in-person game:

  • One-time perishable links – While not the be all end all, vua.sh lets us create a “secret messages” where only the people with the link can access the question – and only once. Once the link is opened once, it’s dead. So, this gives folks a peace of mind knowing that no one can go back and find out what the questions are. The people who create these questions are the last group/individuals who play.
  • One-slide Powerpoint presentations, reminiscent of Jeopardy, with increasing risk/depth factor of questions, scaling punishments with question difficulty/depth.
  • Mailing the “punishments” to the people I’m playing with, like Sean Evans and his team does for their show, Hot Ones, where they mail their 10 hot sauces to their guest before the interview. This way, I can keep people accountable to the punishments
  • Zoom, or an equivalent web conferencing tool – Social distancing at its best. Even better now, ’cause I get to play with people outside the Bay Area as well.

The five lessons I learned

  1. Total conversation time virtually = 100%. Total conversation time in-person > 100%.
  2. First answer makes a difference.
  3. For group calls, preface with introspective intros.
  4. The “extroverts” take over.
  5. Take the bio break.
Continue reading “#unfiltered #39 Five Lessons from Trying to Engineer Serendipity in a Virtual Environment”
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#unfiltered #33 Inspiration and Frustration Pt. 2 – What Drives Some of the Most Resilient People Forward

A few weeks ago, I published Part 1 of this post on inspiration and frustration. In that time, its reception has been uplifting. Easily my most popular and well-received blog post to date. It also happens to be one of my favorite posts to have published so far. So, I thought I’d continue to ask people about their cocktail of emotions now, the below two questions:

  1. What is the one thing that inspires you so much that it makes everything else in life much easier to bear?
  2. What is stressing/frustrating you so much right now that it seems to invalidate everything else you’re doing?

But, each person can only choose one of the above two questions to answer.

Three of the below candid responses are people I asked from the first cohort, while the other eight are people I thought would add a new degree of freedom on perspective. All of which were drawn more to their inspiration than their frustration.

And as such…

  1. It takes a lot of things to inspire and motivate… rather than one individual thing. – Model, writer, founder
  2. I’m inspired to have a hand in making the world better for everyone through technological progress! – Venture capitalist
  3. I’ve made friends with a girl from my neighborhood grocery store and a stranger opened a door wide for me so I could run towards the train and not miss it. – Founding partner/CEO, investor, community manager
  4. When you start to understand that life is bigger than just you and me, there’s a shift in perspective that brings meaning and purpose to our lives. – Zynara Ng, public speaking coach, video producer, TED speaker
  5. We have the means to weather our current circumstances. – Business professor, consultant
  6. We have struggled to find an extremely valuable and painful problem to start with. Nevertheless, someone will figure it out. Why not me? – Startup founder
  7. We just got a new addition to our family. […] I look forward to future conversations about life and deep topics with him, just like this one! – Startup founder, podcast host
  8. We just tend to judge ourselves more harshly because we have our entire past and lived traumas that we judge ourselves by. – Senior policy aide
  9. Their thank you letters, pictures, and stories of how Vinder has changed or saved their business/life solidifies to me that I’m on the right path. – Sam Lillie, startup founder, hiker
  10. Since this goal is so long term and grand, it’s easy to realize that small things don’t matter. – Sohum Thakkar, engineer
  11. In a world that falls short of showing us unconditional love, I can live my life in such a way that I can be that source of acceptance that others need. – Engineer, writer
Continue reading “#unfiltered #33 Inspiration and Frustration Pt. 2 – What Drives Some of the Most Resilient People Forward”
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#unfiltered #27 The Impetus of My Social Experiments – Higher Research and the Application to Startups

bunny, egg, curiosity, curious, social experiments

People seem to love origin stories – both in theatre and in life.

“How did it all start?”

“How did you get into this career?”

Or…

“How did you meet your wife/husband?”

And well, I can’t say I’m one to push back on that.

There’s something truly magical about “Once upon a time…”. And I’m no stranger to fairy tales. Growing up, I was largely influenced by older female cousins and family friends. As soon as our parents left to their wine-sipping adult gossip around a table of blackjack, my cousins and older female friends would drag us to watch their favorite Disney movies on the VCR, namely princess movies. I’m not exaggerating when I say I’ve seen Beauty and the Beast more than 100 times or Cinderella more than 50 times. In fact, my friends in elementary school would talk about their favorite movies – Transformers, LEGO Bionicles, Peter Pan, and Tarzan. Yet, mine was Disney’s 1998 Mulan.

And they all started with “Once upon a time…”

So, it was no surprise when friends, colleagues, and then strangers started asking me:

“How/when/why did you start hosting social experiments?”

Continue reading “#unfiltered #27 The Impetus of My Social Experiments – Higher Research and the Application to Startups”
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#unfiltered #25 Meeting the Curiously Passionate and the Passionately Curious – The Why and The Where

travel, meeting people, rabbi sacks

“It’s the people not like us who make us grow.”

– Rabbi Lord Jonathan Sacks on The Tim Ferriss Show Ep. #455

I recently tuned into, at the time of writing this post, Tim Ferriss’ third most recent podcast episode, interviewing Rabbi Sacks. Although I’m a regular listener to the show, I wasn’t expecting much. I neither have a history of being religious nor spiritual – merely peripheral curiosity. Yet, I don’t hesitate for one second to say: It is, by far, one of the most insightful and enlightening podcast episodes I’ve heard in 2020. So, if you have a spare 1.5 hours, I highly recommend it, especially if you’re looking for a perspective shift on:

  • Leadership,
  • Seeking peer approval,
  • What a single cold “call”/visit could get you,
  • And the need for “cultural climate change” in the understanding between the balance of “I” and “we”.

And Rabbi Sacks masterfully weaves these concepts together. While my reaction will never do his insights justice, two other thoughts, each paired with their own story, I had to double click on:

“Good leaders create followers, great leaders create leaders.”

“What happens when you’re in a situation in which you have done something that has generated widespread disapproval? How do you deal with that?

“Win the respect of the people you respect.”

And I digress.

The Bubble

I’ve lived my entire life so far in the Bay Area, barring a few vacations and excursions here and there. I was born here. I went through 12 years of grade school here. 13 if you count kindergarten. And though I had the option of leaving the Bay for college, I ended up choosing a school here as well. Truth be told, I might as well have “Made in the Bay” stamped on my forehead.

I live in a bubble. But I know I breathe in one. Not just geographically, but educationally, racially, sexually, socioeconomically, and so on.

Being a shy introvert pre-adulthood didn’t help with broadening my perspective on life either. I still remember the days in high school when I dreaded the teacher calling on me. Clammy palms, cold sweat, rigid spine. I would never vocally question disagreement. Equally, I would rather be a people pleaser than cause what I deemed to be unnecessary friction. I was a seafood hors d’ouevres of perturbation.

So, by inspiration from a mentor, I took actionable steps to conquer my own demons. Meet one new person you’re extremely excited to meet every single week for a year.

While I still carry the artifacts of myself yesterday, learning to balance myself between the person I thought and think I needed to become and the person I was, I began my journey 6 years ago.

The Pop in the Bubble

I’d be fronting if I said I wasn’t scared shitless when I began. Though I don’t think everyone in the world has this dilemma, I’m confident I am not alone. I had and have all these scenarios playing in my head. A bunch of ‘what-ifs’. What if they think I’m too nosy? What if they don’t have time to respond? Or what if they hate me for bothering them?

They say it gets better over time. And they’re not wrong. But I still have that lingering, gnawing feeling whenever I click send or put myself out there. While, over the years, the fears never fully dissipated, I’ve learned to tango with discomfort. In the words of my mentor who inspired my journey:

“You’re never as good as they say you are, but you’re also not as bad as they say you are. And hell, you can’t even be bad if they don’t even know who you are.”

… which I believe he drew inspiration from Lou Holtz. Shortly after, I clicked the “Send” button at the bottom of my first ‘curiosity’ email. After all, like he said, what’s the worst that can happen? Getting ignored. And as such, I would be no better nor worse off than I was and am in that cross section in time. With that assurance, it eventually led me to find my cold email “template” and hosting social experiments, like Brunches with Strangers.

The Where

Over the past few weeks, a few new people asked me: “Where do you find these people to reach out to?” Although it’s not the first and I assume certainly not the last, I thought I’d share in the form of this post as a possible inspiration for how we can grow, if I were to paraphrase Rabbi Sacks.

While I don’t characterize myself as a voracious reader, I allot time every day and have found many of my Senseis in the form of literature and discourse – online and offline, printed and taped, and in-person and remote. Including:

  • Books
  • Online articles/press releases
  • Newsletters
  • YouTube videos
  • Movies
  • Podcasts
  • Webinars/fireside chats
  • Textbooks
  • And, other people

One level deeper

To look beyond my own horizon, I tune into Pocket‘s Discover tab, or a platform I’ve recently fallen in love with, Readocracy. You can check out what online reading I’ve been up to lately on my Readocracy profile. And I can’t wait, when I can start tracking the books I read and the podcasts I listen to on there. I’m also fortunate enough to have friends who read, write, listen, and socialize with different social and professional circles than I do and am in. And as I meet more people, the spectrum of topics and interests snowball upon each other, as we help each other see new perspectives – some of which we never thought were possible.

Admittedly, where I find who to reach out to is, by no means, special or esoteric. In topics, I look into ones I’m genuinely interested in, in that moment and predictably beyond, even if it’s only a month or two, as promiscuous as I might be for many. In my short phases of promiscuity, I nevertheless take deep dives. Deep, yet often, not long. At the same time, I have a small handful of evergreen interests, like:

  • The art and science of building relationships,
  • The art of creating irreplaceable memories,
  • Psychology and mental models,
  • Swimming and intense athleticism,
  • Art as a multi-faceted definition,
  • Startups,
  • Technology and what lies at its frontier,
  • The final frontier – outer space and its cosmological inhabitants,
  • And the future.

In people, I look for two things:

  1. Inflection points in their life. Oxymorons/ironies. Overt and covert contradictions.
    • If I were to make assumptions given their initial attributes (i.e. education, age, gender, geography, career, life choices/circumstances, etc.), would I have been able to predict where they are now?
    • Of course, in making these assumptions, it is also my responsibility to be aware and to tread carefully where I should. Unfortunately, ignorance is not an excuse. If I’m unsure, I err on the side of caution.
  2. Deep intellectual curiosity and passion. Whom I call the passionately curious and the curiously passionate.

In closing

While I’m prone to talking too much at times, during these moments, it is my duty and the highest form of respect I can offer, to listen. If I were to take it from a selfish note, I learn so much more when I listen. And in actively listening, and actively checking my biases, to respond with thoughtful questions.

So, I’ll close on more thing Rabbi Sacks said in his recent interview with Tim Ferriss:

“Safe space means that courteous discipline of respectful listening.”

Photo by Mantas Hesthaven 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!

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#unfiltered #22 The Lesson I Learned from Purposefully Replying to Spam Emails – Persistence, The Attention Allocation, and a Little Hack I Use

phone booth, spam emails, communication, cold emails

A few days ago, I watched Yes Theory‘s recent heartwarming and inspiring video, Creating a Subscriber’s Viral Job Application. And if you have a spare 20, I highly recommend checking it out. Yesterday, I chatted with a friend about the influx of spam calls these days. So, I thought; now that’s a start of a #unfiltered blogpost.

As a warning, this post is slightly more eccentric than, admittedly, my average #unfiltered blog post.

Prefacing with spam

I used to write this newsletter, Friday Morning Coffee Break, back in college for one of the clubs I helped lead. (Now that I think about it, coffee seems to be the theme for my content drops.) So if any of you subscribers then are reading this post now, this anecdote will be a momentary skip down memory lane.

So, you see, I’m a huge fan of comedy. And 3 years back, when I first learned about James Veitch, I just had to try it out myself. Replying to spam emails. From Nigerian princes. Cold emails from ‘celebrities’. Confirmation emails that require replying to unsubscribe.

If you’re curious as to how he pulls it off, you can check out his Hilarious (yes with a capital ‘H’) TED talks: here, here, and here.

What I did

When I received:

Subject: Save a 80% Off meds delivered discretely to your door

Don’t miss this once in a lifetime chance to get 80% off of a lifetime supply of Viagra!
GotBanq

… my keyboard was ready.

Continue reading “#unfiltered #22 The Lesson I Learned from Purposefully Replying to Spam Emails – Persistence, The Attention Allocation, and a Little Hack I Use”
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#unfiltered #17 My Favorite Questions from Social Experiments – On Love, Emotions, Candor, and Goals

mirror, reflection, introspection, thinking questions, my favorite questions from social experiments

I’ve given myself the last two weeks to focus on introspection. Rediscovering cross sections of my life – crystallizing them in amber – to find where I can improve the most in. And in the process of doing so, I found inspiration in. I’ve known for a long time that I was, by no means, the smartest person out there. Arguably, my best ideas find the roots of their ‘originality’ in insights from others. From…

  • Friends
  • Founders
  • Investors
  • Subject-matter experts (SMEs)
  • Podcasts
  • YouTube videos
  • Academic journals
  • Blogs
  • And, really creative and really, really passionate people, where their passion is contagious.

… just to name a few.

But, that’s the best part!

Though it wasn’t my initial intention to do so, some of my favorite, most curiously introspective, most thought-provoking questions came from my guests during social experiments, particularly those who partook in Brunches with Strangers and Hidden Questions. Frankly, I can’t take credit for any of them. And just as I learned so much about them and myself from each, I hope you’ll be able to do the same. I don’t expect every question to resonate with you, but I suspect at least a small handful will. If so, my only ask is that you pay it forward in your own meaningful way.

Between 120+ guests between the two of the experiments, here are some of my favorite.

On Love and Emotions

  • When was the last time you said “I love you”?
  • When was the last time you wished you had said “I love you”, but didn’t or couldn’t?
  • Who was the last person you lost in your life that hurt you deeply (i.e. breakup, death, loss of friendship, etc.)?
  • When was the last time you uncontrollably cried?
  • When was the last time you genuinely smiled?
  • What emotion have you given an overemphasis on in the past year?
  • When was the last time you were disappointed in yourself? Why?
  • When was the last time you looked yourself in the mirror and thought “I’m killing it”?What might have sponsored that emotion?

On Lack Thereof

  • Is there someone you pretend to like but don’t? If so:
    1. What is stopping you from sharing your thoughts candidly with them?
    2. What is stopping you from liking them?
  • How many friendships do you regret having broken and never healed? Why?

On Candor to Others and Yourself

  • What are 2-3 things you look for in a person/friend before you are comfortable sharing a secret? How would you prioritize those 2-3 traits?
  • What are you dishonest to others about?
  • Why do you lie to yourself?
  • Over the past year, what have you gotten better at saying ‘no’ to?
  • What are some contrarian beliefs you hold deeply to be true?
    • (Also seen asked as) What is an unpopular opinion you have?
    • Who have you told? Or have you told anyone else?
  • If you could pass 1 value/trait down to your child(ren), what would it be?
  • If there was 1 trait that you could prevent your child(ren) from taking on, what would it be?
  • What is an unusual habit, or an absurd thing you love?
  • What is the best lie you ever told?
    • Do you believe it?
  • What is the most hurtful comment you once said, wrote, or expressed to another?
  • How often do you log on or log off of social media due to envy?

On Goals

  • Do(es) your long-term goal(s) scare you?
  • What’s the craziest thing you did for X?
    • Let X be any goal you’ve once had (i.e. job, relationship, family, grades, to learn, etc.)
  • What is something someone once said to you (good or bad) that keeps you motivated to this day?
  • What failure has set you up for success?
  • If you could title your own biographical movie, what would it be called? And what will it be called post-mortem?
  • What is your 10-year goal?
    • What’s stopping you from accomplishing it in 1 year?
    • If I held you at gunpoint, and told you that you had to reach this goal in 1 month, what do you have to do, starting from now?
  • If you could undo one decision you made in the future, what would that be?
  • What would you like to have written/said in your eulogy?

Photo by Nijwam Swargiary 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!

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