First of all, I should preface. Though I find templates to be useful when you’re shooting for quantity over quality, I default to only using limited elements of one, if at all, when my goal is quality > quantity. The goal with 90% of my emails I have ever sent is where I’m punching above my weight class, be it –
Applying to college – writing a letter to the deans of respective schools to get a personal tour,
Asking for funding – from top-tier VCs and potential long-term partners,
Or, exploring perspectives. I’m pretty liberal in my scope here.
If you’re here reading this and are looking for a silver bullet. If you’re looking to be that John Wick walking away from a massive explosion behind you… well, I regret to let you know – I don’t have one. I wish, but I don’t. But to me, that’s what makes this black box of relationship building ever the more fascinating. Had it been easy, I would have gotten bored real fast. Unfortunately, I have a limited mental stamina for things that work because… well, they work.
Inspired and encouraged by my conversations with 4 amazing souls over the past week – a founder, product manager, startup mentor, and my mom, here are the tactics I learned after years of reaching out to folks that inspire me, specifically closing one a week since 6 years ago.
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:
What is stopping you from sharing your thoughts candidly with them?
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?
#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!
Last week, I wrote a piece inspired by a conversation about diversity, and more importantly, the explicit and implicit biases we hold. And over the weekend, I’ve had some time to think. To think and introspect once again about the biases – explicit and implicit – that I hold. I was specifically reminded of an exercise I learned 2 years ago.
Snapping briefly back in time, one of the most creative and self-aware founders that I know – having just graduated from a top-tier startup accelerator, taught me a mindfulness exercise that he uses every year at the Burning Man camp he leads. I’ve used his framework not only to help myself surface my own unconscious incompetence, but also as the curtain call for a few of my social experiments. He starts with having people focus on their conscious self, then gradually begin to explore our subconscious:
“Take a few seconds to notice who stood out to you. Whom you liked. Who might have caught your fancy. Who you plan to meet up or hope to meet up with after today.
“Now, notice whom you just didn’t click well with. Whom you didn’t like. Who you won’t catch up with after today.
But what I found the most profound was his prompt for the last few minutes of the exercise:
“And finally notice who, for whatever reason, you didn’t notice at all. And pause… and ask yourself why you didn’t notice them.”
Like what the above did for me, I hope this exercise helps provide another frame of mind when considering who we unwittingly leave behind. Why we do so. And how we can shed light to our unconscious to bring to our conscious. Hopefully, in the process, expanding the upper and lower bounds of our cognitive bandwidth.
#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!
It was late that summer Friday evening. The sun had just crossed the horizon, changing the sky from blood orange red to a deeper indigo. Having put in 9000 yards, half of which were back-to-back sprints, we finally wrapped up our 2-hour practice, exhausted and slightly bewildered.
‘Twas our new coach’s first day on the job. We were expecting a chill practice, but this stranger made us work for it. And he did not beat around the bush. Relentless. In sum, he was the Gordon Ramsay of swimming.
Needless to say, he didn’t make the best impression on the team. And it was fair to say that some of my teammates were not his biggest fans. As they all shuffled out, and I had to wait for my parents to come pick me up from practice, I helped Coach with pulling the tarp covers over the pool.
Breaking the silence, he asks, “David, d’ya like to swim?”
“Of course,” I reflexively reply.
“Why d’ya like it?”
“It’s fun. I made friends. It helps me de-stress.”
“No.” And his next few words changed my perspective forever – both in swimming and in life. “You like to swim because you’ve won.”
Showing Gratitude
Obviously, in my prepubescent self, I took my coach’s comment for its face value. I like to swim because I’m good at it. Or at least, relatively speaking among my peers at that point in time. But as I grew older, that comment resonated with me on a different wavelength.
And a conversation with world-class hustler and founder of Fleeting (a company changing the landscape of trucking), Pierre*, last Friday reminded me exactly why. What I said then about why I liked to swim wasn’t completely wrong. I was able to achieve a moderate amount of success in the sport because my parents, coaches, teammates, and other friends supported and cheered for me. But I also forgot to thank one more for my accomplishments. The system itself.
Privilege of having access to coaches and supportive and ambitious teammates,
And, the seemingly minor technicalities,
My lane’s timers had faster reaction times compared to my competitor’s lane’s timers. For context, in regional meets, each lane would always have 3 timers each to record when you touched the wall on your finish, and they would take the median time as the final result.
My lane’s touchpad was working, but my competitor(s) may have had to rely on manual timers since their touchpad didn’t work. So, when it came down to close races and who touched the wall first, I would win.
Of course, there were moments I was a victim to said system as well. And I remember those moments far better than when I won as a result of the system.
So what?
The thing is, when everything is going my way, I often take it all for granted. One of the only times I realize and realized that there might be any flaws to the system are when I am left out. I have been and am a member of society that has profited from the systems – in swimming, in higher education, in work opportunities, just to name a few. And I’m sure there are even more I have yet to realize that I have benefited from.
The past few weeks have been a wake-up call to America, to the world, and to myself for what we have all let pass without questioning. And admittedly, it may be difficult to assess what explicit and implicit biases we have when we, in the words of Coach, are “winning”.
Diversity at the Table
So, it comes down to two fronts: internally and externally.
Internally, introspectively, let’s ask ourselves:
What have we won as a result of? And, what are we still winning in?
What have we benefited or profited from?
And just as there are winners, there exist still who have yet to win. Or win in a more consistent manner.
Externally, we need to bring into the fold those who have yet to win to help us assess what systemic flaws exist in our status quo. Frankly, it’s incredibly difficult to find our implicit biases alone. I know that I’ve been reminded multiple times in my life by those who are more cognizant in those arenas than I was and have been. And, those underrepresented and underestimated by the system can use all the help they can get.
Together, I’m confident we can find a better solution.
#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!
Looking outside my bedroom window, I watch as the limitless canopy above me slowly changes from a velvety warmth to a crisp blue. The morning jays chirp in a heavy New York accent, asking when the next metro will arrive. They fly by my window several times, stealing a glance at me. Thinking “we haven’t seen this fella at this time before”. Their eyes beckon as if I held the answer to their pressing question. I don’t.
I’m writing this piece with a heavy arm, due to the Wii Sports I played with the fam yesterday evening. All the while, feeling its weight as I sip the green tea my dad bought from who knows where. He brought back the small, unassuming brown bag to our household last year, with neither a name or a place to call home. From my friends in the business, they tell me that’s a sign of high quality leaves. ‘Wouldn’t that also be a sign of the exact opposite?’ But I never had the courage to ask. Ironically, my palate betrays my thoughts. A warm earthy coating enveloping my tongue, with an expected bitter finish. My culinary friend sent me a copy of The Flavor Bible 2 days ago. In it, I learned a simple math equation:
Flavor = Taste + Mouthfeel + Aroma + “The X Factor”
Right now, in this moment, I think I finally graduated from high school algebra.
Google tells me we’re hitting a summer 94 here today. This year I have yet to don a farmer’s tan. On the brighter side, I’ve spared my skin the horror of being overcooked. A few friends and neighbors have gone to orchards and vineyards to cherry pick and brought back the spoils of war. Some coming back more cherry-looking than the cherries themselves.
Another friend, elated with starting her boutique culinary business, sent me a couple bags of agar powder to experiment with, which I have yet to open. Today, after work, I’ll put them to good use. Or bad use, if my human guinea pigs crinkle their nose from my mad science experiments. Who knows?
Well, I’m headed downstairs now to start another great day. This time, with a beautiful sunny side up with dash of furikake, smoked paprika, and good ol’ S&P.
Why am I writing this? There’s been a concentration of negative energy surrounding us right now. And when I say ‘us’, I use the royal ‘us’ in a loose sense here. In these special, turbulent times, life’s become increasingly stressful. For a handful of my friends and family, it’s easy to find someone or something to blame. In some cases, there is a responsible party. But in most others, the ‘blame’, if we need to give the beast a name, is shared in a much broader sense. And we forget the beauty in our world. What we’re grateful for. What we have lived to see in another spectacular day.
And once again, I’m using the royal ‘we’.
Many of my colleagues use the Five Minute Journal App – short snapshots of daily gratitude. The first thing they do every morning. But I think I’ll stick to longer expositions.
#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!
I met a founder (let’s call him Stan) recently who was about to close on his first big executive hire into a team less than 10 strong. Naturally, I asked what the rest of his team thought of that person. Stan replied, “I haven’t asked them yet.”
So, I subsequently followed up, “Were they able to meet him?”
“He’s been by our office, and I’m sure he’s had the chance to chat with them already.”
When he said that, two things stuck out to me:
Stan’s use of “I’m sure…” implied neither that he was sure nor that he took care to verify.
He seemed to have skipped a fundamental step in building a team. And by transitive property, how it would define his team’s culture.
The Culinary Parallel
Synonymously, a day later, my friend asked me, “How do you come up with your ideas for flavor mad science?”
You’re probably here thinking: “What the hell does this have to do with team-building and culture?” But bear with me here. I swear there’s a parallel.
Although, like all of my ideas and insights, I can’t say any of my flavor experiments are truly original, I always start off at the drawing board with flavor maps. And, you guessed it! Not even the concept of flavor maps is original. A few years ago, an amazing chef taught me this very trick of how he concepts new recipes every season at his critically acclaimed restaurant.
So, what’s a flavor map?
The idea of a flavor map is to start with a core ingredient – the star of your dish. And then slowly add other flavors and elements onto your diagram one by one. The catch is that every new flavor you add has to pair well with every single other flavor on that diagram.
Two flavor maps where I used green tea as the (co-)core ingredient.
Personally, I just try to think of a dish that I enjoyed, or know many other people enjoy, as the basis for a drawing a line between a pair. The reason I do so is that many generations of experts before me have already done the legwork to make these flavors work. And I’m just iterating off of their discoveries.
The more scientific approach is through flavor networks – specifically food-pairing and food-bridging. In summary, food-pairings are when you combine two ingredients with the same flavor molecules, like cheese/bacon or asparagus/butter. The most bizarre one in a 2011 Harvard study is probably blue cheese/chocolate, which share 73 flavors. On the other hand, food-bridging is when you take two ingredients that don’t share any flavors, like apricots/whiskey, and bridge them with an ingredient that shares commonalities with both, like tomatoes.
Yong-yeol Ahn and his colleagues explore the nuances of flavors and recipes in their 2011 research, which you can find here. But if you want the abridged summary, there’s a great one on Frontiers. Yet, as one of the co-owners of a critically-acclaimed molecular gastronomic restaurant told me not too long ago, take the research with a grain of salt. Food science is still extremely nascent and lacks consistent data points, especially across cultures.
Looping Back
Just like a complete flavor map has all of its ingredients working in cohesion with one another, a strong team needs to hold the same level of trust and respect. I’m not advocating that you need to agree with everyone on your team. In fact, disagreement on warranted grounds is better. But to be a well-oiled machine, a team can only be agile if you reduce the unnecessary friction that may exist now or arise in the future.
Although it is important that every team member can ‘food-pair’ with every other member, what I believe is more important is to have a fair mitigation system to ‘food-bridge’ all current and future disagreements. A system to resolve disputes and to prioritize tasks at hand. To have not only trust in each other, but also in the system design.
The cherry on top
Of course, I don’t know if Stan just forgot to set up times for his team to meet with the potential hire between his various tasks of running a business. Or if he had something he wanted to hide from his team. Regardless, his decision, or I guess, lack thereof to do so, would be detrimental to the delicate string of trust that connected his team to him.
To his and every other founders’ credit, there are often matters that seem obvious to an observer, but less so, when one has skin in the game – some degree of emotional attachment. And the deeper one is in the weeds, the harder it may be to follow rational behavior. Loosely analogized to the boiling frog problem. That said, some actions are excusable. These can often be caught by either a mentor or a close friend/family member. But there are a handful that aren’t. The same can be said on a macroscopic perspective as well. Between friendships. Lovers. Coworkers. You name it.
And, luckily for Stan, this falls under the former.
#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!
Last week I spent some time with my friend, who joined me in my recent social experiment, brainstorming and iterating on feedback. Specifically, how I could host better transitions between presentations. She left me with one final resonating note. “Maybe you would’ve liked a creative writing class.”
I’ve never taken any creative writing courses. I thought those courses were designed for aspiring writers. And given my career track, I never gave it a second thought. Well, until now. I recently finished a brilliant fictional masterpiece, Mistborn: The Final Empire written by #1 New York Times bestselling author, Brandon Sanderson. So, that’s where I began my creative journey.
In my homework, I came across his YouTube channel. One of his lectures for his 2020 BYU writing students particularly stood out. In it, he shares his very own Sanderson’s Laws.
The three laws that govern his scope of worldbuilding are as follows:
Your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.
Flaws/limitations are more interesting than powers.
Before adding something new to your magic (setting), see if you can instead expand what you have.
Outside of his own books, Sanderson goes in much more depth, citing examples from Lord of the Rings, Star Wars, and more. So, if you have the time, I highly recommend taking one and one-fifth of an hour to hear his free class. Or if you’re more of a reader, he shares his thesis on his First Law, Second Law, and Third Law on his website.
But for the purpose of this post, the short form of the 3 laws suffices.
The First Law
Your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.
The same is true in the world of entrepreneurship. Your ability to successfully fundraise is directly proportional to how well the investor understands your venture. Or more aptly put, how well you can explain the problem you are trying to solve. This is especially true for the 2 ends of the spectrum: deep tech/frontier tech startups and low-tech, or robust anti-fragile products/business models. Often times, the defensibility of your product comes down to how well people can understand what pain points you’re trying to solve. You may have the best product on the market, but if no one understands why it exists, it’s effectively non-existent.
Though not every investor will agree with me on this, I believe that too many founders jump straight into their product/solution at the beginning of their pitch deck. While it is important for a founder to concisely explain their product, I’m way more fascinated with the problem in the market and ‘why now?’.
You’re telling a story in your pitch. And before you jump into the plot (the product itself), I’d love to learn more about the setting and the characters involved (the underlying assumptions and trends, as well as the team behind the product). As my own NTY investment thesis goes (why Now, why This, why You, although not in that particular order), I’m particularly fascinated about the ‘why now’ and ‘why you’ before the ‘why this’. And if I can’t understand that, then it’s a NTY – or in millennial texting terms, no thank you.
My favorite proxy is if you can explain your product well to either a 7-year old, or someone who knows close to nothing about your industry. Brownie points if they’re excited about it too after your pitch. How contagious is your obsession?
The Second Law
Flaws/limitations are more interesting than powers.
Investors invest in superheroes. The underdogs. The gems still in the rough. And especially now, at the advent of another recession and the COVID crisis, the question is:
How much can you do with what little you have?
And, can you make the aggressive decisions to do so?
I realize that this is no easy ask of entrepreneurs. But when you’re strapped for cash, talent, solid pipelines, are you a hustler or are you not? Can you sell your business regardless? To investors? New team members? Clients/paying users?
On the flip side, sometimes you know what you need to do, but just don’t have the conviction to do so, especially for aggressive decisions. You may not want to lay off your passionate team members. Or, let go of that really great deal of a lease you got last year. You may not want to cut the budget in half. But you need to. If you need to extend what little you have to another 12-18 months, you’ve got to read why you should cut now and not later. Whether we like it or not, we’re heading into some rough patches. So brace yourselves.
But as an investor once said to me:
“Companies are built in the downturns; returns are realized in the upturns.”
The Third Law
Before adding something new to your magic (setting), see if you can instead expand what you have.
And finally consider:
Can you reach profitability with what you have without taking additional injections of capital?
Can you extend your runway by cutting your budget now?
But if you need capital to continue, do you need venture capital funding? I’m of the belief, that 90% of businesses out there aren’t fit for the aggressive venture capital model.
How scrappy are you? How creatively can you find solutions to your most pressing problems? And maybe in that pressure, you may find something that the market has never seen before.
In closing
Like a captivating fantastical story, your startup, your team, your investors, and especially you yourself, need that compelling narrative. The hardest moments in building a business is when there’s no hope in sight – when you’re on the third leg of the race. In times of trial, you need to convince yourself, before you can convince others. To all founders out there, godspeed!
And as Sanderson’s Zeroth Law goes:
Always err on the side of what’s awesome.
If you’re interested in the world of creative writing or drawing parallels where I could not, check out Brandon Sanderson’s completely (and surprisingly) free series of lectures on his YouTube channel.
Yesterday, having read my most recent blog post on social experiments, one of my friends asked me why I decided to finally start the blog. My simple answer was “to make myself obsolete”. The question that inevitably followed was:
“Why?”
Although not incredibly common, I’ve had a very small handful of friends and family ask me similar questions. All of which either directly ask or border “Why share all my secrets?”. Admittedly, all is subjective in this case, as I’m not keen on posting my social security or my social media log-in information on here.
Wouldn’t I be more competitive in this saturated (although I argue otherwise) market if I kept them to myself?
On a startup front, wouldn’t sharing the rationale of others and my own enable founders to “game the system?”
In response to (1), your competitive edge in the 21st century isn’t how many ideas you’ve hoarded, but how many you’ve executed on. And frankly, if we can cooperate to build a better world, why not?
For (2), if founders can “game the system” just by reading my blog, which requires them to have concrete evidence for growth and the questions fellow investors and I pose, well then, it’d be a great example of “faking it till they make it”. My blog merely provides a framework, plus a few stories, to how some of the smartest people around have overcome their obstacles. By the time the system tests them, I hope they’ll conquer the adversity in front of them and have the discipline to push forward.
What’s inside the black box?
I’m extremely happy to share “my” secrets. And I use the term secrets loosely, much like Peter Thiel does in his book Zero to One. In fact, the only reason I have any insight into life is that experienced experts were generous enough to share theirs with me. In other words, none of my insights are truly original. All are borrowed from the best, until I create a version that I resonate with more.
Simply put, if my ‘secrets’ and insights help even just one person out there to live a better life, then I’m a happy camper. My goal is to make the future a better place to live in. Oddly enough, it also happens to be one of the reasons I’m in venture capital. Only by sharing what I believe to be right and morally right am I able to help move the needle, if only by a little bit. As I’ve mentioned before, I’m a huge fan of people going through the idea maze and spending time and effort on insight development. If I can help catalyze those motions in my readers through my blog, then I’ll toast to that.
The Flip Side
However, I should mention there are secrets that I will carry to the grave with me. For instance, outside of the obvious, like SSN and credit card info, ones that…
My friends/colleagues tell me in confidence,
Cause more harm than good in the world,
Cause more harm than good to the people around me,
Carry malicious intentions,
And/or reveal why I put OJ in my breakfast cereal.
#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!
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:
Build a system to help me discern my two halves of knowledge.
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.
#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.
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As much as investors love founders with passion (or obsession) and grit, they also want to invest in founders who have the capacity to grow as individuals as much as their startup grows. And that boils down to how curious and open-minded they are. In other words, how coachable are they? In the past 2 weeks, I’ve had the fortuity to talk to 2 brilliant angel investors – each with their own respective formula for measuring founder coachability.
Formula #1: Assessing Peer Coachability
Last year, I shared a post about the importance of all three levels of mentorship – peer, tactical, and veteran. With the most underappreciated one being peer mentorship. For the sake of this post, let’s call the first angel, Marie. Similarly, Marie finds that peer coachability acts as a useful proxy for founder coachability. And she approaches peer coachability in a very unique way:
What do you and you co-founder(s) fundamentally disagree on?
Following that question, usually 1 of 3 scenarios ensue:
The co-founders can state what they disagree on. And by follow-up question, share how they resolved that disagreement, then how that applies to their framework for resolving future disagreements.
They figure it out on the spot. Better sooner than later.
They say, “Nothing.” And quite possibly, the worst answer they could provide. ‘Cause that means they just don’t understand each other well enough. It’s highly unlikely that given how complex human beings are, that there can be two ambitious individuals who have the exact same outlook on life. Even twins have variations in their perspectives.
Knowing what co-founders disagree on assesses not only how well founders know each other, but also, how they’ve learned from each point of friction. Whether intentionally or not, they become each other’s coaches and push each other forward.
Formula #2: Assessing VC-Founder Coachability
Jerry, on the other hand, tests the waters by offering a controversial opinion about building a business or an insight into the industry, but one he has conviction and experience in. Then, he waits to see how the founder responds. The founder(s) can either:
Disagree, and subsequently walk through where the dissent starts and offer a sequence of data and analyses as to why he/she believes in such a way.
Agree, but still offer how he/she reached the same conclusion.
In either case, Jerry is looking for how mentally acute a founder is and how much room for discussion there is between them. On the other hand, the strike-outs regress to 2 categories:
Disagree, and spend time trying to convince Jerry why he is wrong, rather than working to persuade Jerry to possibly see a bigger picture he might not have considered before. And sometimes, this bigger scope includes a marriage of Jerry and the founder(s) insights.
Agree or disagree, but unfortunately, is unable to substantially back up their claim. Becoming a yes-man/woman in the former, or an argumentative troll in the latter.
The Mentorship Parallel
Unsurprisingly, just like how VCs use these methods to assess founder coachability, I’ve seen mentors use similar methods to assess potential mentees. Many aspiring mentees seek mentorship for its namesake – that metaphoric badge of honor. Not too far from the apple tree when people start a business or come to Silicon Valley to be called a CEO or for their company to be ‘venture-backed’. A category of folks we designate as “wantrapreneurs”.
And unfortunately, many aspiring mentees find bragging rights to be the mentee of [insert accomplished individual’s name]. Yet they don’t actually mean to learn anything meaningful, much less accept constructive criticism. Realistically, no mentor wants to go through that mess. “If you want for my advice, you better take it seriously,” as my first mentor once told me.
In closing
A great VC’s goal is to be the best dollar on your cap table, but they can’t be that Washington if you don’t let them be one. And though it doesn’t call for your investors or board members to micromanage, it does mean you are expected to be candid in both receiving and using (or not using) feedback.
