#unfiltered #11 What I Learned About Building Communities through Social Experiments – Touching Jellyfish, Types of Social Experiments, The Thesis, Psychological Safety and Fairness

jellyfish, social experiment, psychological safety, how to build a community
Are these jellyfish friendly or not? Will they “bite”?

As colorful and as beautiful jellyfish are, we are still scared of the possible danger that each possess. So, most of us only admire them from afar. And for many of us who have seen some, we’ve watched them float gracefully in dark blue aqueous solutions across a sometimes distorted film of glass. These beautiful mysteries of the deep blue.

To Touch the Jellyfish

Much like my fascination every time my parents brought me to the aquarium as a kid, I’ve been fascinated with the people around me. Especially about the thin, sometimes distorted, film between these exceptionally fascinating souls and me. The distortion created as a function of society’s, as well as their own, efforts.

Exactly a year and two months ago, I embarked on a journey to host small-scale social experiments, like:

  • Hidden Questions. A game where no one else knows the question, except for the person answering it. And where the person answering has the choice of sharing the question that inspired the answer or taking it to the grave by taking a shot of hot sauce (about a 700,000 on the Scoville scale, for reference) or a variable number of Beanboozled beans.
  • Brunches with Strangers. Quite literally, Saturday brunches with strangers. Hosting a cast of people from all walks of life. Like founders, street artists, astrophysicists, concept artists, athletes, criminal investigators, filmmakers, college drop-outs, and much more.
  • The Curious Case of Aliases. Where players (strangers to each other) under aliases guess each other’s hobbies, occupations, deepest fears, etc. after only playing in a 30-minute game session. For instance, skribbl.io. Cards Against Humanity. Codenames. And Mafia.
  • And, the most recent addition to my small Rolodex of social experiments, Improv Presentations. A TED talk-like night where people present someone else’s creatively esoteric slide decks, with no context as to what’s in the deck until they’re on “stage”. To the postmortem dismay of my cheeks and core, we saw everything from how to survive a cat-pocalypse to how to master the art of DM’ing using military tactics to how to be a good plant parent.

The Thesis, The Questions

As COVID would have it, the lack of in-person interaction and self-quarantine inspired the last two. Yet, all of which with the same thesis: helping make the world feel a little smaller, a little closer, and a whole lot more interesting. Starting not with the people who bathe in the limelight, but with the people directly around me.

Why is it so hard to be candid with strangers? And sometimes, even harder with family and friends?

Do we need alcohol, drugs, crazy incidents, violence, a lack of sleep, or stress to truly be ourselves?

Though not all-encompassing, people seem to be naturally curious about things, events, status, money, and gossip. Why aren’t people more curious about people – well, as just themselves? Like me, you’ve probably posed and have gotten the question: “How are you?” or “How are you doing?”. And likely, with more times than one is willing to admit, we didn’t really care about what the answer might be. Often times, since we know we’re just going to get a “Good” or “OK” in response.

If you want to have some fun, I highly recommend the next time someone asks you that, say “Terrible”. And watch the computer chip in their brain malfunction for a quick second.

What did I learn?

I won’t claim I found the universal truth or a holistic answer to any of those questions I posed above. Because I haven’t. After all, someone I really respect once told me:

“50% of what you know is true. 50% is false. The problem is you don’t know which half is which.”

So, in my life, my goals are two-fold:

  1. Build a system to help me discern my two halves of knowledge.
  2. Expand the total capacity of what I know.

I will share more on this blog as I am able to draw more lines of regression myself.

But in the context of this post, through social experiments, I’ve discovered that people yearn for psychological safety. Not only does Google’s Project Aristotle share its effectiveness in the workplace, it’s equally, if not more true, outside of it as well. The reason that it’s sometimes easier to share your thoughts and struggles with strangers is that strangers often won’t judge you to the same extent as friends and family do. Frankly, they don’t have much context to judge you from – implicitly and explicitly.

People want fairness. Not in the sense of you get 1 cookie, so I should get 1 too. But a fair system to be judged by. That I will get the same benefit of doubt as you will give to anyone and everyone else. When we all get drunk together, we will all be drunk and we will all relieve ourselves of any filters we may previously have. And though everyone’s drunk personality is different, and frankly everyone will still be judged… For that moment, that night, everyone’s on the same playing field.

The Applications

Let’s take most recent experiment with improv presentations as an example. The initial idea was that everyone should present their own slide decks. As serious or as silly as they might be. But some of my friends were hesitant. In their words, they felt they needed to “impress” or “have better public speaking skills”. Some simply said that they didn’t think they’d “be as good as others”.

Before our first “TED Talks@Home”, I shifted it altogether where we’d all be presenting each other’s presentation. All of us would have no context as to what we’re presenting until we get on “stage”. Whether we were experts on a specific topic or in comedy or deck-making, we’re all jumping into a bottomless pool together. After our second virtual improv night, this past weekend, between muted giggles and visual laughs, one of the presenters told me that it wasn’t as bad as she thought it would be, and that she’d want to do it again.

Luckily, it seems more than 60% of my friends, colleagues, and acquaintances come back to participate in more brunches or game sessions or improv nights. 1 in 4 guests have proactively started friendships outside of the experiments. And about 5% have introduced their new friends to their friend circles. A small handful have also been inspired to start their own. So, maybe I’m doing something right.

Building Communities

The same (psychological safety and fair system) holds true for building communities, creating your corporate culture, and finding and keeping your friend group and your significant other. Although in the context of building communities, but applicable elsewhere as well, I forget who told me this once:

“A strong community has both value and values.”

– The person who told me this, please come claim this quote

Value is why people initially come out to join a community and admittedly, reach out to be a friend. Whether it’s because of who you know or what you can offer or how you can help them pass the time, it’s the truth. Values are why they stay. And safety happens to be one of those values.

In closing

As always, my findings aren’t meant to be prescriptive. But merely act as a guide – another tool in your toolkit – so that you are better equipped for future endeavors.

Like with people, when one day I get to touch a jellyfish, I don’t care about being stung. But I do want to know where I can touch where I won’t be stung. And subsequently, where I will touch where I know I will be stung. The difference between going in blind and not is that when I get stung, I am prepared to be.

Photo by Mathilda Khoo 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!

#unfiltered #10 Idea Journals – How to Start, Prompts that Stretch your Parameters, The “Right” Setting, Embracing Imperfection

idea-journaling, sunrise, sunset

Three weeks ago, in the prelude to this post, I mentioned the art of ideating and how I personally pursue the expansion of my creative horizons. Though I have or had other systems in place (i.e. whiteboard in the shower, pen in pocket everywhere I go, meditation), idea-journaling has been, by far, the most impactful in stretching my creative muscle.

When you start:

  • Dedicate your time to doing it daily, with no cheat days. Set aside ten minutes each day to do so.
  • Invest in a journal you love. Don’t skimp. I fell in love with the Moleskine sketchbook at first sight. Though I have graduated to the Leuchtturm1917 sketchbook now. For me, investing in a higher end journal made me more inclined to journal daily – not wanting my Hamiltons go to waste.
  • Don’t worry about completeness or complexity. A journal entry can be 1 sentence or 5 pages or even a drawing. Regardless, dedicate a minimum of 1 page to each entry, even if you only fill it in with 1 sentence.

Explore different mediums of thought. Here are some of the prompts I started with:

  • Write a short story.
  • Draw a picture.
  • Design a logo.
  • Compose a tune.
  • Jot down a recipe you think could work. And after, how would you plate this dish?
  • Create a new language.
  • Write a poem in that new language (or language that’s not your native tongue).
  • What stood out to you today?
  • Write out a conversation you would have with your role model, a celebrity, your boss, your friend. Or even what your follow-up conversation would look like with someone you talked to today?
  • How would you resolve a problem that’s plaguing you now?
  • If you could change or add one fundamental universal law, what would you change and why?
  • And, if you’re still stuck without a prompt, what should be the question or prompt you ideate with today?

Why? By exploring different avenues of creative output, you give your mind more degrees of freedom to think. Expand your parameters. That’s why multi-linguists are able to host such a vast vernacular bandwidth.

The Setting

Just like the process of idea-journaling, the setting in which you do so is equally as important. Why? You ideate best in a positive or neutral environment, when you won’t tie down emotions and biases to the environment you’re journaling in. Find your sweet spot, and make it a routine. When and where do you find yourself to be the most relaxed and/or the most creative?

For me, although I don’t shy away from ideating throughout the day, I find my mind the most expansive: (1) right after I work out, and (2) right after a good hot shower. And though rare, if the above two don’t work, I take at least a 20-minute walk, tuning into either a podcast episode I’ve heard before or a non-lyrical playlist.

Once I find peace in the preamble of my ideation “ritual”, then I settle down in a place where I feel comfortable and at home. Before the crisis, my go-to spot in the city was Sightglass Coffee on 7th. Now it’s in my backyard garden. With good lighting and a cup of chamomile or green tea.

Embracing Imperfection

My idea journals are a sanctuary for me to be imperfect. And arguably, its is where I found myself to be the most courageous. I didn’t have to cower in fear of judgment and biases from other eyes. And I can be unapologetically myself. Over the past 2 years, I’ve been lucky for that same courage to have bled outside of the book-bound acid-free pages.

If I can quote a line from the prologue of Bob Iger‘s brilliantly wicked book, The Ride of a Lifetime

“True innovation occurs only when people have courage[…] Fear of failure destroys creativity.”

Give yourself room to fail. You’re not going to like every single one of your ideas. In fact, if you’re like me, you might end up hating 4 out of 5 ideas you have when you first start off. But keep at it. Make it a habit. And one day, you’ll notice the distribution of good-to-bad ideas shift in your favor.

If you’re anything like me, when I get stuck, take some time to look up at the jewel-studded indigo canopy above. As your mind hops between one twinkle to the next, you might pick something up in the traversal.

As you make it a habit…

Although an unintentional upside when I embarked on this journey, the endeavor is truly meditative, perpetuating a positive feedback loop of euphoria. And over time, you’ll find yourself concepting more robust and intricate ideas. Hopefully, unbounded by your situational constraints. The sky’s the limit!

Photo by Leon Biss 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!

#unfiltered #9 Living to Eat – Supporting the Service Industry, Fine Dining Musings, Restaurant Selection Criteria, Tipping, and the Notebook

living to eat, fine dining

I had originally planned to write this post back in February, but when the coronavirus came crashing in 6th gear, I thought it would have been unwise to urge you, friends and family to venture beyond your doorstep. So this post fell into the depths of despair, hoping to find its way to center stage after we were on the road to recovery and when restaurants reopened.

But yesterday, over a Zoom call, in catching up with a fellow foodie and college buddy, he suggested that I still post this. Not to urge people to eat out. But as a voice to support the many struggling restaurants, cafés and bars out there – many of which include our personal favorites. Before I dive into this post, I want to explicitly note 2 disclaimers:

Disclaimer 1: As I mentioned above, this post is not written to incentivize you to go eat out now, but rather just illustrate my musings as someone who loves food. And as many other businesses are feeling the brunt of the impact in the status quo, the culinary industry is no exception. Your favorite restaurant yesterday may not exist tomorrow. And you won’t even be able to experiment with any of the below musings if we don’t put a hand out now and support them when they need us most.

Disclaimer 2: I am neither a professional chef/cook nor is my trade being a food critic. So take what I say with a grain of salt, as with anything I write. Below is merely my observations in one of my most expensive hobbies as a foodie.

Given the extravagant length of this post, here’s a TL;DR:

  • Why I don’t resort to Yelp/Google when picking a new dinner destination
    • And a couple of my favorite restaurants in the Bay Area
  • My calculus for tipping – and why there are times I choose to not tip
  • Why a notebook may be your best friend in your culinary adventures
Continue reading “#unfiltered #9 Living to Eat – Supporting the Service Industry, Fine Dining Musings, Restaurant Selection Criteria, Tipping, and the Notebook”

#unfiltered #8 The Oasis – Fiction, Books I’ve Recommended/Gifted the Most, How I’ve Kept Myself Busy Outside of Work

book, fiction, reading

Lately, I’ve picked up a few fiction books – 2, to be specific – The Three Body Problem by Liu Cixin and Mistborn: The Final Empire by Brandon Sanderson, by recommendation of a friend and founder, respectively. And damn, they’ve rekindled my love for worldly escapes. Prior to high school, I used to be the biggest fanatic of fiction books. Although proportionally smaller, my fictional “library” at home still includes:

  • every single book in the Magic Tree House series by Mary Pope Osborne
  • the entire Redwall series by Brian Jacques,
  • every single one in the LEGO Bionicle series,
  • the Alex Rider series by Anthony Horowitz,
  • Dune by Frank Herbert,
  • The Steel Wave by Jeff Shaara,
  • and much more.

And to further how much I nerded out over fiction, I knew our local librarians by their first name and memorized by library card number by heart (to this day) – all for the sake of fiction. But as I grew older and entered my teens, I was told that I should have outgrown fiction. That it should stay as a remnant – a fond memory – of my “youth”. So, I slowly acquired the taste for non-fiction, biographies/autobiographies, business books and documentaries.

Yet, in some ways, in this serendipitous situation, when now I have more free time, and by fervent inspiration from the two aforementioned angels, I found sanctuary in other worlds. I saw with my imagination and heard with my eyes. For lack of better words, it was magical.

From non-fiction, I’ve been able to walk alongside the greats who have once or now inhabit the reality on this small blue pearl amidst a sea of unknown. From fiction, I’ve been able to walk alongside the greats who have never lived in this reality, maybe never will, but somewhere out there, they hold the keys to our dreams. Each hold a proud seat in my heart, but the latter has been dormant for over a decade.

Books I’ve Recommended/Gifted the Most

I should preface that I’m not the most voracious reader out there – although that’s been changing over the past 4-5 weeks. But here are my favorites which I’ve recommended/gifted the most:

  • 2018 fav – The Messy Middle by Scott Belsky
    • Short (1-3 pages, on average), but incredibly insightful chapters of product/design/leadership lessons from a founder/investor/product leader, especially during messy times post-honeymoon stage of being an entrepreneur. My favorite pages… 232-234. A set of three questions to create a lovable product.
  • 2019 fav – The Trillion Dollar Coach by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle
    • A dedication to the most well-known least famous person in Silicon Valley. From the book title, you might be able to guess what he did – all of which he took zero compensation for. Having been suggested and subsequently read too many leadership books earlier in my career, when I first suggested this one, I was quite skeptical. I thought it was just another one of those, until I heard the name, Bill Campbell. A name which I’ve heard more than once from various people who attributed their success to him, since 2016. And I’m so glad I didn’t dismiss this one. I only wish I could have gotten to know the amazing person this book is dedicated to.
  • Startup fav – The Hard Thing About Hard Things by Ben Horowitz
    • A book that doesn’t sugarcoat the tough decisions in building a company – a set of decisions illustrating on how he dealt with situations when things just wasn’t going his way. Rather than being prescriptive, it gave me a framework for understanding the various struggles a founder will encounter – most of which I had yet to see when I was recommended to read this book. Quite pertinent in today’s landscape, ironically.
  • Most nostalgic/impactful on personal growth – The Art of War by Sun Tzu
    • I was first given this book when I graduated from elementary school, as the problem child, though not in the traditional sense. I had a knack for blaming others when problems arose, but this book helped me understand people better and where people were coming from. In all honesty, I don’t know why it clicked when I was only 10, but it did. Apart from my childhood bias, though specific to leadership in a military regime, you can draw several parallels between the art of war and business and life.
  • Fiction fav – Salamandastron by Brian Jacques
    • Brian Jacques throughout the entire Redwall series just has such a way to weave suspense and an emotional attachment to the various characters. Admittedly, it was the first fictional book I cried to while reading, so it holds a special place in my heart.

For the sake of not overwhelming you with too much, I’ve only included the ones I’ve statistically recommended/given the most, as well as gotten the most positive reactions from folks I’ve offered these to. If you’re interested in a more exhaustive list, feel free to DM me – either through this blog or social media.

Keeping Body and Mind Busy

For many of my other friends and colleagues, they have found similar solace in books. Many in the kitchen. Some with instruments and a camera. A handful with a mic and Twitch or Anchor.

Because I have saved 2-3 hours of travel time every day now, I’ve been:

  • Doodling at least thrice a week in my Leuchtturm notebook, specifically their medium sketchbook (180g/sqm, so on the thicker end of pages);
  • Jumping on game sessions with friends over the weekends, like on Skribbl.io or recently, Songversations (Discord is definitely my favorite medium of social interaction, especially with all the bots they have. My favorite of which is the Groovy music bot where I can tune into music alongside my friends);
  • Reaching out to 1 new person I’m insanely curious about every week;
  • Idea-journaling every day;
  • Trying new recipes and methods in the kitchen;
  • Trying new home workout routines;
  • Reading fiction and non-fiction;
  • Writing for this blog 😀 ;
  • And, a new social experiment between friends, family, and colleagues, in hopes of making this world feel a little smaller, just a little closer, and a whole lot more interesting.

So, if you have the time and privilege to, explore new/’new’ genres and mediums of storytelling, creativity, and activity. Some may very well surprise you!

Photo by Ksenia Makagonova 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!

#unfiltered #7 Words are Food – Having Empathy, Job Resources Now, Letting Staff Go, and Perspective Shifts

words are food, empathy

I jumped on a call with my good buddy, incredible founder and one of the most magnanimous people that I know, Mike, not too long ago. And no, he did not pay me to say that. As always, we nerded about everything on the face of this planet, but one thing in particular stood out to me. And inevitably manifested into the foundation of this #unfiltered post. He said, just 3 words:

“Words are food.”

The more we delved into this rabbit hole, the more robust the metaphor began. But for the sake of not running your ear off, I’ll cover just one facet of our parallel.

Compliments are sweets. They’re great in moderation, but too many give you cavities. They wrap up a great meal, but you cannot live your life only indulging in compliments. On the other hand, constructive criticism are your vegetables. They may not taste the best, but they’re healthy for you. And a healthy diet should consist of mostly fruits and veggies. Yes, brussel sprouts and eggplants too. Of course, it’s important to note that blatant criticism, like “You suck” or “You’re dumb” is garbage. They neither taste good nor are they healthy for you. You can smell it from miles away. So just steer clear.

After all, you are what you eat. 😀

Empathy in Words

In the past 4 months, we are all going through a transitory stage in our lives – some more drastic than others. Some of us have experienced the deaths of loved ones. Some, a test of relationship integrity. Others, career shifts and a change in household income. For those of you who have been affected by the job market, my friend passed me this resource which I hope you’ll find use in honing your job search. Anecdotally, it seems pretty accurate.

And almost everyone, a dietary change and restriction, due to the market’s supply and demand. And it’s more important a time than any (not that you shouldn’t when the curve flattens and the markets recover), be empathetic.

Be kind – with your actions and your words. In these times, it’s so easy to be caught up in what’s not going right in your life, but you’re not alone. You never are.

Empathy in Business Now

Although this applies to so many different aspects of our lives, I’ve found its pertinence on the business front recently. When the focus of businesses now is on cash preservation rather than growth, which I’ve alluded to in previous posts (1. cash in private markets, 2. heeding advice , 3. brand as a moat), aggressive decisions can be tough. As the saying goes, measure twice, cut once.

Here are some examples of said (preemptive) decisions I’ve seen from founders so far:

  • Reallocating 30% of the company budget to the core business from expansion and venture bets (70-20-10 rule of thumb to 100-0-0)
  • 50% cut to CEO salary, 10% cut to management, 5% from everyone else, to try to minimize layoffs
  • 100% cut to founder(s)’ salary, 35% cut to management, everyone else keeps theirs the same, while offering healthcare benefits for temporary workers/contractors

The conclusion for some founders may reach the point of laying off people who followed you believing in your dream. You can check out Mark Suster‘s, Managing Partner at Upfront Ventures, rubric for questions you need to consider in empathetic moments of business decisiveness.

Empathy won’t change decisions. The tough, but true remarks are your vegetables. People will still have to eat them, but be understanding of where the people eating the food you cooked up are coming from. Rather than boil your brussel sprouts, offer crispy ones with a soy glaze, a little heat, and a layer of bonito flakes.

Perspectives Forward

Recently, I had the fortune of connecting with a founder whose parents were refugee who found sanctuary in the states. She put things wonderfully into perspective, when comparing the current situation to the one she was familiar with as a child.

“There are 2 camps of refugees: (1) those who want things to go back to the way they were before, and (2) those who move forward knowing that life will never return to the ‘normal’ they once knew.

“And those who progress forward are those who believe in the latter.”

When the dust settles after all of this, life won’t ever be the same as it was 4 months ago. The hospitality, transportation, travel, and service industries, just to name a few, will irrevocably change. You friends and family may have lost dear ones.

Alas, I’m an optimist. And I know that we’re going to come out stronger than we were when we went in. We’re going to have to get used to a new diet. I dare say, even a new vernacular.


#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!

#unfiltered #6 The Quantum State of Advice – The Marriage of the Schrödinger Equation and Cold Emails

quantum, schrodinger's cat, advice
Photo by Danilo Raphael Reyes on Unsplash

“The rearview mirror is always clearer than the windshield.”

– Warren Buffett

Although Mr. Buffett said that in relation to business, I find it equally true everywhere else. Just like the rearview mirror and the windshield, I want to denote the dichotomy between feedback and advice.

  • Feedback – given post-mortem, after-the-fact, help after peering into the rearview mirror
  • Advice – given “pre-mortem” or in an ad-hoc sense, help offered proactively, looking through the windshield.

As this title suggests, for this post, I’ll just be focusing on advice. And well, that may be as profound as this post will get, the rest is just a trip down my nerdy shower thoughts after watching this video about parallel worlds my equally nerdy friend sent me.

You have been warned…

The world right now

Well, you see, I work in an industry that thrives off of giving advice. Especially in these trying times when businesses are not only trying not to lay off their staff, many are working around how to stay afloat. My friends in culinary projected a 50% decline in occupancy rate, but at this point, have shifted entirely to to-go options and lowered their own salaries anywhere from 35% to 100%. My pals in D2C (direct-to-consumer), transportation, or travel have been punched in the gut. And, my entrepreneurial buddies are doubling down on cash preservation, rather than growth. The rule of thumb we’re telling founders to have at least as much runway to weather the next 18 months. So if that requires pushing up your fundraising schedule, then time to re-prioritize.

The nerd comes out

But after decades worth of receiving advice and years worth of giving advice, I learned something that seems like a no-brainer now. You see, the thing is advice is both right and wrong simultaneously. You can say it’s in a superposition of being right and wrong… at least until that advice is observed by its subsequent application and result.

Let’s take it a step further. Can we predict the probabilistic effect of advice on a given situation? Sure. So, let’s take a look at the Schrödinger equation.

Image result for schrodinger equation

There’s a few elements that stand out. |Ψ(t)> denotes a time-dependent function. And, H(t) denotes the sum of the kinetic and potential energies for all the particles in the system. In relevance with advice, the timeliness ( |Ψ(t)> ) of the advice matters – in relation to both where you are now and where you’re heading. The eigenvector of you. At the same time, it’s important to factor in your velocity now and everyone and everything else’s involved in the situation.

You might be wondering how come I didn’t analogize to the classical mechanics version of this equation: F=ma. Excellent observation! The reason is that the classical mechanics version doesn’t account for wave-like probabilistic outcomes. And advice and its relative observation by application doesn’t have a guaranteed outcome. Rather, it plays a hand in either increasing or decreasing the outcome of an event.

Here’s an example

One of the first lessons I learned, if not the very first piece of advice I got, when learning about ‘Cold Emails 101’ was:

“Limit your email to 3-5 sentences.”

Makes sense. I didn’t want to bombard the person I was reaching out to. I want to make it easy for them to read and reply to. But over the years, I learned that the real answer to email length is ‘It depends’. If you’re reaching out to someone who:

  • already has a lot of clutter in his/her inbox,
  • has expressed disdain or annoyance in reading emails,
  • doesn’t check his/her inbox often,
  • has a succinct personality (person-of-few-words),
  • or anything else that suggests they’re not going to bother with a long email,

… then send the 3-5 sentences. But if that person:

  • wants to see that you’ve spent your time doing your diligence (not a generic spray-and-pray email),
  • has a more extreme sense of self-worth,
  • is curious/open to flushed-out new ideas/perspectives,
  • enjoys a tale,
  • is a comedian,
  • or anything to suggest that a longer email may stand out to them,

… then craft a longer message. I was able to get in touch with some of the people I really admire by crafting lengthier emails. That said, there’s always a bit more nuance in all of this. Here’s a piece I wrote last year that may provide some context. And this is only probabilistically higher, holding all other variables constant.

Even so, there’s always more than two options. DM them on their most active social media platform. Get an intro. Send them meaningful content. Send a hand-written note by messenger hawk. Visit them in person, without unwanted trespassing. Go viral by making a lollipop with their face on it. Buy an extrasolar star and name it after them. The list is endless.

In sum, the advice of limiting the verbage of your emails is right and wrong at the same time. It merely depends on where the person you’re reaching out to is at and where they might be headed, as well as your own goals in life. And of course, as with any advice, limiting your sentences may boost or detract from the likelihood of a reply.

The disclaimer

As is the nature of an analogy, it breaks down when you get more granular. I should mention that I’m no astrophysicist (dealing with the macro) nor am I a quantum physicist (the micro). And I’m sure if any relevant occupation were to look into my analogy, there’d be tons of holes. I am merely a peripheral enthusiast.

quantum advice
My scribbles on paper which turned into this post.

#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!

#unfiltered #5 The Insider “Silicon Valley” TV Show – The Show, plus Thoughts on Eccentric Cold Emails and Crazy Startup Pitches

Tech satire.

I gotta say I love it! Memes. GIFS. YouTube vids. TikTok clips. The whole nine yards.

As a testament to how much I love satirical memes and GIFs, six years ago, when I was testing out “best” cold email methods, as a semi-random A/B test, I emailed half of the folks I reached out to, leading or ending with either a meme or GIF. The list ranged from authors to musicians to researchers to Fortune 500 executives to founders to professional stone skippers. And the results weren’t half bad. Out of 150 odd emails, about a 70% response rate. Half of which resulted in a follow-up exchange by email, call, or in-person. The other half were gracious enough to say time was not on their side.

So when I learned, from the most recent episode of Angel podcast, about David Cowan’s version, I just had to check it out. And I wish I had only discovered it sooner. Made by Director Martin Sweeney, and co-visionaries, Michael Fertik of Reputation.com and David Cowan of Bessemer Venture Partners, bubbleproof is tech hilarity… made by the folks who have tech day jobs. Though I still haven’t watched the 6 seasons and 53 episodes of the Silicon Valley TV series yet. Sorry, friends who keep recommending it.

I just finished episode 5, where they share a snapshot of comedic ideas and pitches – from lipid fuel technology to an Airbnb marketplace for prisoners. And not gonna lie, I had a good chuckle. But when the episode wrapped up and I finally had a chance to think in retrospect, those ideas could have been real pitches in some world out there. When I first started in venture, I met with my share of cancer cures predicated off of a happiness matrix and feces fuel and African gold brokers. In case you’re wondering, yes, I did get pitched those. The last one admittedly should have come through my spam folder.

In these next few weeks, while you’re WFH (work from home), if you’re curious about tech from the ironic perspective of those who live and breathe it every day, check the series out. Only 10 episodes. 7-15 minutes per. (And while you do that, maybe I’ll finally get around to watching Silicon Valley. But no promises.)

As a footnote, Bessemer also has a track record for being forthcoming and intellectually honest. I would highly recommend checking out their anti portfolio, that lists and explains not their biggest wins or losses, but their biggest ‘shoulda-coulda-woulda’s’.


#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!

#unfiltered #4 Namedropping and Intros – Why my default is to not to namedrop, Direct/Indirect Consequences, Making/Receiving Intros, and Notes on Friendship

namedropping and intros, fame
Photo by Einar H. Reynis on Unsplash

One of my buds asked me over the weekend why I often don’t namedrop, mostly in respect to this blog. Well, other than the quotes I use that already exist somewhere on the Interweb. It’s not the first time I’ve been asked about namedropping. And I usually my TL;DR response is that I want to respect their privacy and time.

My longer answer is a bit more nuanced. Here are my reasons to why:

  1. If I’m true to my emotions, I would love to namedrop at every opportunity I get. Given that some of the folks that inspire me to write specific pieces are echelons above me, it would help me get exponentially more traffic. And for a minute, I can convince myself that people come to my site for the content. Yet, in reality, there are confounding variables, part of which is whom I’m rubbing my shoulders with.
  2. Although I tell them during our conversation, I send my pieces to the people who inspire me retroactively. In receiving feedback, if existent, after I publish my thoughts, I can truly give a play-by-play cross section of my thoughts at any given time. If I believe the feedback/advice is pertinent, I will compound upon the advice in a future post. After I publish the pieces, if they want to be associated with it, they can, which leads to my third point.
  3. Fame is a fickle thing – a double-edged sword. I’m not saying my blog currently has millions of views every month, nor am I projecting that it’ll ever. Would be nice, but not a priority. But since I do write on a public blog which can be found via various search engines and browsers out there, I am cautious and respectful of people’s comfort levels in the face of the public eye. So, before they decide to have their names on my blog, I send them this incredibly intricate piece Tim Ferriss wrote about fame. On the bright side, social recognition, the opportunity to take on bigger projects, the ability to mingle with people of a similar or greater popularity, and more. On the flip side, stalkers, harassment, extortion, death threats and so on. In understanding the “disclaimers”, then I retroactively put their name up.

Because of these reasons, I’m also, to my friend’s credit, testing the question: Are these people real? The supposed elephant in the room. No matter how much I plead my case, there’s little I can do to convince you these individuals are real. I don’t host a podcast (although I may in the future), nor do I ask them to post on their social media about my content. If you don’t believe they are, they aren’t. If you do, I thank you for your confidence in me. And that’s all I can really say to that question.

Outside of the blog, I try not to namedrop, unless it becomes impossible to explain a conversation topic without using their name. I’ve had such cases before that upon using X person’s name, friends, family, coworkers, and/or acquaintances implore an introduction. After all, as my job entails, I live off of introductions. I live and breathe in a relationship-based industry. And because I do, I’d like to say I have a deep understanding with the value, as well as the risks, a person needs to take:

  • to make an introduction (which I brief in this piece),
  • but also, to receive an introduction.

The person making it is risking social capital, or in other words, their reputation. The person receiving it is risking time (and effort) allocation. And when you’re punching above your weight class, the person receiving it has to weigh the opportunity cost of taking an intro versus the projects they’re currently undertaking, as well as prioritizing a new contact over their existing network. If I do make an intro, I always shoot for a double opt-in, where both sides agree to it.

Early last year, I heard something I don’t know why it didn’t click sooner. As part of the Crazy Gremlin (CG) (long-story short, we couldn’t think of a better name) event series which I help co-host, we get in-person feedback with each and every attendee. Why? We can dig deeper than we can with survey forms, like:

  1. Understand the deeper emotional spectrum,
  2. Ask pertinent follow-up questions,
  3. And, notice macro- and micro-gestures that’ll supplement how forthcoming their answers are (i.e. Does a “9” on the NPS question really mean a “9”?).

For context, the thesis behind CG events is helping strangers become life-long friends overnight.

In that feedback process, one of our attendees told me: “I’m never going to come to your events again.”

I asked, “Why do you say that?”, assuming that we did something terribly wrong.

“You guys didn’t do anything wrong. In fact, you held a better event than I imagined. But in coming to the last event, I realized I would rather prioritize my current close friends than spend time meeting new people, whom I don’t know if I’ll catch up with later.”

He made me realize that:

  1. We failed at bringing people closer together, fundamentally being comfortable with being vulnerable, at that event.
  2. There’s a giant population of folks out there who say they want a social life and to meet new people. But what they really mean is that they’re still looking for that friend or group of friends with whom they can really truly be themselves with.

To this day, I don’t think namedropping or making intros when only one party could benefit is conducive to lasting friendships. So, although it makes me giddy, and you can argue, in a myopically-beneficial sense, I proceed cautiously.


#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!

#unfiltered #3 Plan Bs – Should we have them?

I woke up today with a thought that’s been gnawing at me for years now. Why do we have backup plans – Plan Bs, Plan Cs, etc? Does it inhibit our drive? Or readily prepare us for the worst? At what point are we sacrificing our commitment for safety?

When I started this blog, my writing mentor recommended that I have 10 pieces written and ready before I launch my blog. And I did exactly that. All cards out, I still have 8 of my pieces saved in my backlogs, which as you have already deducted, I’ve used 2 of my pieces already. Why? My mentor told me that, in my commitment to publish content weekly, I will indubitably have dry spells – dry weeks. And I did… twice. So, I regressed to my lowest common denominator and pulled something out of my archives. But during those two weeks, it helped me stay in my comfort zone. That instead of fighting writer’s block (if such a thing exists), I chose to run from it.

Part of the reason I started this #unfiltered series is to help me be content with content. I am guilty of 8/10 times second-guessing my way out of doing something. If I contemplate over something long enough, I’ll realize fears that I never thought possible, and opt for the safer option – not doing it at all.

From when we were young, we’re taught to always prepare backup options. When applying to colleges, we’re told to apply to our 2-3 reach schools, and 10-15 other schools we’re confident about getting into. When applying to jobs, one of my hometown neighbors, 2 years my senior, advised me to apply to 200 jobs, expect 10-20 interviews, another 3-5 for final rounds, and 1-2 offers to choose from. Effectively, asking me to apply to 198 backup alternatives.

I get it. As the saying goes, beggars can’t be choosers. Both high school and my early years of college have drilled that saying into me – by my peers and by my teachers.

A part of me hates it, but a part of me realizes the truth in there. I saw that circumstances played an even larger role for my friends and peers who:

  • are going through tough times in this pandemic and economic downturn,
  • (whose) parents came from a lower income bracket,
  • are POC (people of color),
  • are female,
  • are/were open about their different sexual orientations,
  • didn’t graduate from a 4-year college,
  • lost limbs or appendages due to accidents or conflict,
  • are/were in debt,
  • and much more.

Half a decade back when I set out to meet one new person that drew my insatiable curiosity a week, I realized I’m a goddamn privileged person living in the 21st century. I’m a perfectly healthy, heterosexual Asian male who graduated from a 4-year university. If all hell breaks loose and my net worth goes to absolute zero, I have my parents’ home to go back to and a room and bed to call my own. And as a full disclaimer, the fact I’m contemplating this question in the first place means I’m privileged enough to do so.

And because I’ve had the liberty to do so, I realized that my greatest personal achievements came from when I didn’t give myself the option of a Plan B. For the people I reached out to and am in touch with above my weight class, I either have given it my all or was prepared to do so. For swimming, I treated each competition as my last, meaning I either gave it my all or nothing. And during more nights than I can count, I beat myself up over my inability to reach a milestone.

Yet, now in the land of venture, we learn to hedge our bets and come up with contingency plans. We learn once again to diversify our portfolio, and not put all eggs in one basket. Does that lead to why many investors fundamentally don’t have the conviction to lead deals?

On the founding side, you have it almost flipped. When you are trying to make ends meet, there will be times you have to take that one option and go all in. And you can’t let go until you do everything you can to make it a reality. When you sit in a position of privilege, you can have several contingency plans to hedge your bets. Ben Horowitz, author, founder, and investor, illustrated the dichotomy in his piece (and one of my favorites) about peacetime and wartime CEOs. There’s a part of me that strives to find that sense of urgency, like a wartime CEO. And go all in. Maybe this pandemic is the test where I can find where my values really lie.

To be frank, I haven’t come up with a conclusion to the dilemma. For now, I can only hypothesis-test and keep good track of the data that comes my way. But, so far, I can say that one’s tolerance for risk is positively correlated with one’s free cash flow.


#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!

#unfiltered #2 Culinary Tips – Cook vs. Chef vs. Flavor Mad Scientist- The Carbs, the Proteins, and the Whole Spectrum

unfiltered vc, cooking tips
Photo by Calum Lewis on Unsplash

As a result of my love for food, and eating out, honestly, a bit too much, what started as engaging conversations with chefs at some of my restaurants, and eventually chefs from across the country turned into a passion for cooking. Uhh, well, although I can’t call myself a cook or chef, I have categorized myself as a flavor mad scientist.

  • Cook – someone who can prepare food
  • Chef – someone who can create recipes appreciated by a wider audience (personally, don’t care if they’re a professional or not)
  • Flavor mad scientist – someone who attempts to be innovative and likes experimenting with permutations of flavors and textures (80-90% ‘failure’ rate), aka me

So, I chatted/learned from chefs/cooks, ranging from some of the most prestigious kitchens to my favorite home kitchens. Here are some tips and hacks I got from some of the best:

For the carbs:

  • You can tell if a risotto (or rice in general) is cooked by smearing a rice grain on a flat surface. If it smears without noticeable lumps, you’re good.
  • Add a teaspoon of olive oil in the pasta dough to give it a bit of shine.
  • Flour matters. Don’t just use all-purpose. 00 (double zero) for silkier flour and pasta chewiness. Durum for coarser grinds, longer cook times, and for making flatbreads; some use it for pasta too, depending on the chef. And so on.

For the proteins:

  • Score the fat of a (ribeye) steak before searing, so it’s easier to render the fat. Score is a cross-hatch pattern. More surface area to render.
  • Use tongs to cook steak and a spoon to butter-baste (I swear I used to think it was spelled “butter-basing”)
  • Don’t cook cold proteins (meats/seafood). Let it rest till room temperature before cooking.
  • Allow for meats to rest for as long as you’ve had it in the pan to better absorb the flavors.
  • Before searing proteins, dry with a paper towel or season generously with salt to reduce moisture and splatter once you put it into the pan.
  • Hot pan/hot oil, quick sear and won’t stick to the pan.
  • Brush fish with mayonnaise to prevent them from sticking to the grill. And a great browning too.
  • Use cuts of meat that are rich in marrow and collagen (cartilage) to make stock, like wings, chicken feet, chicken carcass, pork knuckle, etc.
  • If you don’t have a meat thermometer, stick a metal rod (or a cake tester) into the center of the meat. Then place the rod on your lower lip. If it’s cold, more time. Hot, it’s done. If you’ve burnt your lips, well… in gamer terms, GG.

For everything else:

  • If your meats or onions ain’t sizzling in the oil, the oil in your pan isn’t hot enough.
  • To not bruise your herbs when chopping (or chiffonading if you want to be fancy), you need a sharp knife and cut once per cross-section. You can tell if you bruised your herbs by the residue they leave on the chopping block.
  • Lemon juice, ideally fresh, helps fruits from oxidizing (after being cut), so it retains its fresh color.
  • Flavor extra virgin olive oil (EVOO) with herbs (i.e. bay leaves, basil, rosemary, thyme, oregano, etc.) for the “secret” zing to your recipes. You can do the same with white wine that’s used for deglazing the pot/pan.
  • Zest citrus in once in one fluid motion with a zester to prevent mixing in the bitter rind.
  • Use fine grinds for salt and pepper to season pre-cook, and coarse grinds for post-cook/presentation.
  • Buy whole spices and a spice grinder (or pestle and mortar), instead of ground spices. You’ll get fresher and richer flavor that way.
  • Toast spices for more flavor.
  • Under-seasoning is a rookie mistake. (Admittedly, after this tip, I fell under the category of over-seasoning.)
  • Keep your work station clean. Mise en place.
  • Wear short sleeves while cooking, or roll up your sleeves.
  • If you’re a 4-eyes, like me, invest in contacts. Glasses can fog up from the steam, and possibly blur your vision in critical moments.
  • Don’t skimp on costs. Quality cookware and ingredients lead to quality food. (Not saying you can’t otherwise get a good meal, but you’ll notice the difference.)

This post was inspired by a friend’s comment on my Instagram post on February 5, 2020.

culinary tips, unfiltered, plating
You may notice that I just transcribed what I wrote on paper to this blog, with some extra sprinkles on top.

#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.