Category: #unfiltered

Posted on

#unfiltered #50 What is Your Opening Bid?

“Is your opening bid to assume trust – to assume someone is trustworthy – and to grant them the full benefits of that? Or is your opening bid to not trust, but the trust can be earned?”

Over the past weekend, my friend shared this brilliant interview between Jim Collins and Shane Parrish at Farnam Street. The same friend who recommended this podcast that catalyzed my essay on how to think like an LP. So, needless to say, when she sent me this one, I had to tune in. I’ve been a big fan of Jim for a long time, ever since one of my favorite college professors recommended that I read Good to Great. He has an amazing talent with wordsmithing – bringing seemingly incongruous concepts together in analogous harmony. So when Jim uttered the above quote, I took my Staedtler pen and 180 g/m2 paper out.

“Have you ever considered the possibility?”

Jim also shared, “Brutal fact: Not everyone is trustworthy. And the brutal fact is that some people abuse that trust.” Some people will abuse that trust. Some people will really let you down. But that, in my opinion, as well as Bill Lazier’s – Jim Collins’ mentor, is just the cost of living. That shouldn’t change your disposition in the world, but rather illustrate how much more you should cherish the ones that are trustworthy.

Jim furthered that notion with another anecdote from his mentor, Bill. “Have you ever considered the possibility, Jim, that your opening bid affects how people behave? If you trust people, you’re more likely that they will act in a trustworthy way. So it’s a double win. It’s the best people and they’ll behave in a trustworthy way. The flip side is if you have an opening bid of mistrust, the best people will not be attracted to that. If you have an opening sense of you have to earn my trust, […] some of the best people are gonna be like ‘I don’t need to put up with that. I’ll go do something else.'”

Thinking aloud

Coincidentally, a few weekends ago, one of my good friends hosted a thought lounge. The first I’ve participated after hearing about it for a few years. The purpose of which, and I quote, “is meant to be a place where passionate people come together to practice dialogue and have meaningful conversations.” Every person brings in a topic that’s designed to spark kinetic intellectual energy that each lasts for 12 minutes. And where “creative conflict” is encouraged.

It just so happens that one of the four topics that came up that day was the law of attraction. A concept that states that similar people attract each other. And that one’s thoughts can attract similar results. The more you think you will succeed, the more likely you are to succeed. And likewise the same might be true for failing. One of my fellow participants brought up a great Henry Ford quote: “Whether you think you can, or you think you can’t – you’re right.”

And it acutely reminds me of a story I once read in Tim Ferriss’ Tribe of Mentors. Robert Rodriguez, who directed one of my childhood favorite franchises Spy Kids, shared with Tim when asked the question, “If you could have a gigantic billboard anywhere with anything on it, what would it say and why?”

“I like the idea of setting impossible challenges and, with one word, making it sound doable, because then it suddenly is. So I’d choose FÁCIL! for my billboard. It’s a good reminder that anything can be done, with relative ease and less stress, if you have the right mindset. […] Attitude comes first.”

In closing

“Is your opening bid to assume trust – to assume someone is trustworthy – and to grant them the full benefits of that?”

That’s the line I need on my fortune cookie. If one day I unwittingly become a foolhardy skeptic, I want to open up a fortune cookie after a lonely meal I’ve stuffed myself to the brim on. On a quiet late night Uber ride home, thinking I’ve eaten all I can eat… I want to read that line.

My opening bid is trust. It always has been. And I hope it always will be. I know that people have taken advantage of my kindness and trust. And I know there will be more that will in the future. But I hope I never lose the optimism in my eyes.

My opening bid is still trust. What’s yours?

Photo by Marek Piwnicki on Unsplash

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

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

Posted on

#unfiltered #49 Doing Boring Things

I recently tuned back into Elizabeth Gilbert‘s, author of Eat Pray Love, 2016 interview with On Being. It also happens to be one of my favorite interviews about creativity and curiosity. I found myself pausing, rewinding, playing, pausing, rewinding, then playing again one line again and again.

“Everything that is interesting is 90 percent boring.”

She further elaborates, “And I think one of the reasons that both my sister and I ended up being authors is because we were taught how to do boring things for a long time. And I think that’s really important, because here is one of the grand misconceptions about creativity, and when people dream of quitting their boring job so that they can have a creative life, one of the risks of great disappointment is the realization that, ‘Oh, this is also a boring job a lot of the time.’ It’s certainly tedious. It’s a boring job I would rather do than any other boring job. It’s the most interesting boring job I’ve ever had. […]

“And we are in a culture that’s addicted to the good part, the exciting part, the fun part, the reward. But every single thing that I think is fascinating is mostly boring.”

She takes it from a perspective that everything has its boring parts. So you have to learn to accept what’s boring along with what’s interesting. I think she’s absolutely right. But while I was tuning in again to that same interview – those exact same lines – for who knows, the 20th time, I thought… maybe there’s something more. Forgive my brain for having the tendency to jump into numbers and equations. That for some reason, one of the primary ways I understand life has to be through some quantitative lens. I thought, what if we take it from an expected value perspective.

Expected value = 10% * (Utility of interesting) + 90% * (Utility of boring)

The utility we gain from boring, often times, is of course, well… boring. Some utility value less than zero. Or in other words, more often than not, we lose utility. On the other hand, the utility we gain from interesting is positive. So, then it becomes a balancing act between what’s interesting and what’s boring. That in the decision to pursue something interesting, there might be the below subconscious calculus:

10% * (Utility of interesting) > 90% * (Utility of boring)

To shine a different light, is the interesting part interesting enough that it outweighs all of the boring parts combined, and ideally, more?

Take, for instance, writing for me. I love writing. It’s meditative. Thought-provoking. And it’s challenging. But at the same time, editing, filling in the keywords for SEO, finding a cover image, all the way to writing when I don’t feel inspired, but I do so to commit to a weekly routine is tedious.

Similarly, Gilbert uses the example of raising children. “Raising children — I’m not a mother, but I’m a stepmother, I’m a grandmother, I’m a godmother, I’m an aunt, and I know that 90 percent of — especially, being with very small children…

“Incredibly — it’s hard. And then there’s the moment where you realize, ‘Oh, my God, this is a spark of creation that I’m working with, and this is magic, and this is life seen through new eyes.’ And creativity is the same, where 90 percent of the work is quite tedious. And if you can stick through those parts — not rush through the experiences of life that have the most possibility of transforming you, but to stay with it until the moment of transformation comes and then through that, to the other side — then, very interesting things will start to happen within very boring frameworks.”

For many of this blog’s readers, it’s starting a business. Whether you’re changing the world or the people you care the most about, that mission is what drives you. That’s what makes it interesting. And every time you hit a milestone –

  • Your first user outside of your friends and family,
  • Rated #1 on Product Hunt,
  • One of your customers writes a handwritten love letter to you and your team about how you saved her family,
  • You finally have enough revenue to pay your team members who’ve been working with you for free for two years,
  • $1M in ARR,
  • 50,000 users,
  • You reach profitability,
  • Your dream investor says yes,
  • A Fortune 500 business offers you 9 figures for your business,
  • And the list goes on and on.

… it’s exciting! But let’s be honest, not every day will be sunshine and rainbows. 90% of your days will be tedious. Some percent of those days or weeks might even suck! 90% of your days will be you working to find and reach that 10%. And if that 10% is just that amazing, it’ll make that 90% worth it.

In a sense, it’s like the Pareto Principle. 80% of your utility will come from 20% of your achievements. That star 20% – your customer love letters, providing employment for all your team members during the tough days of COVID.

In an analogous mental model, in everything that is boring, there might be a small percentage that makes it interesting. Now I’m really curious as to what I might discover here.

Photo by Sophie Dale on Unsplash

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

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

Posted on

#unfiltered #48 Am I Valuable in this Ecosystem?

In the past month, I’ve doubted myself and my abilities more than I have in the past two years combined. Half from putting myself intentionally in tough conversations, half from pursuing new opportunities to see them turn belly up. The latter is merely a fact in life. But coupled with the former, I can’t say I was always the happiest camper. So, when in one of the former’s conversations, someone asked me: “Are you worth anything in the startup world?”… I hesitated for more than a day, before I had the courage to give myself an answer. While it was a rhetorical question then, it is a question I need a companion answer to now.

  1. Nothing. Without entrepreneurs, I am useless in this ecosystem. On the flip side, if there are entrepreneurs that I can help find product-market fit and grow, I’m a percentage-based function of their growth. Let’s say as an investor, I own 10% of a company. If the company’s worth $0, then I am too. If it’s not zero, then I’m worth whatever 10% of the whole is worth. Is that a representation of my true market value? No. It’s merely an assumption that for, say, $250K for 10%, I am worth, in the long run, at least 10x of $250K to help founders move faster on their journey.
  2. Something. How much? I don’t know. My job is to help pair founders with the knowledge, skills, and relationships that will transcend the outcome of the venture itself. They say entrepreneurship is never a zero sum game. Even if your idea doesn’t find its product-market fit, the time you spend hustling is cross-applicable to any other industry. Can founders find the knowledge, skills, and relationships without me? Most likely. There are so many resources online via YouTube, Medium, Substack, Quora, just to name a few, that it’d be silly of me to think I’m essential. What I can do is expedite the journey towards their goals. Hopefully even alleviate some stress. And even when I do so, I’m only truly useful in one chapter of their journey rather than the whole novel. But if my worth is just to reduce the friction it takes to get us one step closer to live in the world we want to live in tomorrow, then so be it.

I’m reminded of what Ashmeet Sidana of Engineering Capital said recently. “A company’s success makes a VC’s reputation; a VC’s success does not make a company’s reputation. In other words to take a concrete example, Google is a great company. Google is not a great company because Sequoia invested in them. Sequoia is a great venture firm because they invested in Google.”

Photo by Sunrise Photos on Unsplash

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

Posted on

#unfiltered #47 Two Ears, One Mouth

I’ve been this self-proclaimed “few screws loose” for a while. Rationally, what I do, it doesn’t always make sense. But in their post-mortems, my adventures often turn out to be invaluable lessons of growth. The month of March was no exception.

It all started with someone who reached out to tell me I didn’t know what I was talking about. And subsequently, that I should stop writing. It certainly wasn’t the first, but definitely the most direct one to date. I saw where he was coming from. I’d never personally taken an idea from inception to scale, much less exit. On the venture side, I’m a scout, and well that means, I don’t personally invest in many deals, if at all.

At the same time, it’s not like I didn’t expect such a comment. As a content creator, even an amateur one, I’m putting myself out there. And in doing so, I’m opening myself up to criticism. This, well, just the first of many more to come. In fact, I’ve alluded to it before. As Jeff Bezos once said, “If you can’t tolerate critics, don’t do anything new or interesting.” Now before I make myself seem smarter than I actually am by appealing to authority, I’m not. Simply, I believe their few words profoundly summarize what might take me an essay to convey.

In writing weekly content, and subsequently, doing my homework to write the best I can on any given topic, I give off the illusion that I’m smarter than I actually am. And every once in a while, I fall victim to using esoteric phrases. Like I could say the same statement above as: I give off the illusion that I have a larger repository of information than I have. But I do so because sometimes I really, really like the phrasing I come up with or come across. It’s more of a personal fulfillment than a misleading façade.

Like I’ve mentioned before… I write to think. An unrefined concept that through the process of writing, I come to a more robust understanding. But let’s be honest, it’s not all up and to the right. It’s a rollercoaster. I love how Packy McCormick, who authors Not Boring, described his own writing process.

After all, mine doesn’t fall too far from the apple tree. But I digress. That one message led me down a path to jump on phone calls with other folks who found my content or myself to be disagreeable. Some more perverse and antagonistic than others. Five people total. Four who had just fallen on a series of unfortunate events. Two of which just wanted to be heard. The other two seeking advice and feedback. And last who seemed to find power through berating me for 20 straight minutes. One other who has yet to respond.

Why? I’ve known for a while that I’m terrible at having tough conversations. Some of my friends might know from personal experience. A number of other founders who’ve been on the receiving end of my inability to say “No”. Especially when I first began in venture.

I thought that maybe – just maybe – if I go to the more extreme end of the spectrum, I might get better at giving others the respect and time they deserve. While I’m not sure if the five conversations have helped me mature, they made me a better listener.

When two broke down during our short call, what they needed wasn’t advice or feedback or someone to tell them everything was going to be alright. They just wanted someone to listen. Just listen. Given my personality, I was constantly tempted to respond. To give advice. And to ease the “awkward silence.” But it wasn’t awkward at all. My inability to recognize the sanctity of silence made it awkward.

For the two other founders, they sought feedback since no investor they chatted with so far gave them any constructive ones. I couldn’t promise connections nor capital. All I could promise was my own radical candor. And they were free to do with it as they saw fit. So I spent 10-15 minutes with each, listening to their pitch. No questions in between. My thoughts only chronicled on a 5×8 notepad in front of me. And only after they’d concluded, I would share my thoughts.

The last one, frankly, there was nothing I could do or say that would have changed his mind. And rather than trying to, which would only reinforce his belief, the best I could do was stay silent and occasionally smile.

I’m reminded once again of a line someone I deeply respect once told me, “The quality of communication is measured by not how much comes out of your mouth, but by how much reaches the other person’s ear.” And another, “We have two ears and one mouth; we should use them in that proportion.”

And I am still working on it. I have a long road ahead, but I’m positive if I keep the above lessons in mind, I’ll go further faster.

Photo by Jonathan Sanchez on Unsplash

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

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

Posted on

#unfiltered #46 Soon May the Investor Fund

Not long ago, there was this massive TikTok craze on sea shanties. And while I don’t have a TikTok account, the ripple effects have reached me as well. What started as a shower thought after a founder recommended I gamify my advice to founders fundraising, well… turned into this. To the tune of Soon May the Wellerman Come:

There once was a team that put to sea
The name of that team was Friends ‘N Me
The winds blew hard, but growth tipped up
O’, burn that midnight oil (huh)

Soon may the investor fund
To bring us money and help and some
One day, when the term sheet’s done
We’ll take the dough to grow

She had not been two years from start
When push became the pull we sought
The founder called all hands and wrought
The product to scale now (huh)

Soon may the investor fund
To bring us money and help and some
One day, when the term sheet’s done
We’ll take the dough to grow

The servers’ now a right real mess
We had to call the AWS
They had us pay for more bandwidth
But that’s okay with us (huh)

Soon may the investor fund
To bring us money and help and some
One day, when the term sheet’s done
We’ll take the dough to grow

We’ve tripled our growth last year, oh yus
With dollar retention as one cause
When we were asked what it was
We said ’twas one twenty (huh)

Soon may the investor fund
To bring us money and help and some
One day, when the term sheet’s done
We’ll take the dough to grow

We’ve ten cust’mers that five of which
Are referenceable you’ll find on pitch
That one of which is kinda rich
They’re paying hundy K (huh)

Soon may the investor fund
To bring us money and help and some
One day, when the term sheet’s done
We’ll take the dough to grow

Photo by Katherine McCormack on Unsplash

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

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

Posted on

#unfiltered #45 Two Questions that Force Me to Face My Own Ego

“Ego is about who is right. Truth is about what is right.” – Mike Maples Jr.

I distinctly remember reading this soundbite on page 64 years ago in Tim Ferriss‘ then-new book, Tribe of Mentors. With the recent string of world events over the past few months, I’m reminded once again of this line. It’s strange to think that our most available mentors come in the form of books. Yet, every time I realize this fact, I seem to stumble upon another Eureka moment.

I was a passively-rebellious kid growing up. Though not often, there were times I would swing left when my parents said right. High school, on the other hand, did not make it any easier for my parents. As if puberty was not enough, in high school speech and debate, I learned to play the devil’s advocate on nearly everything. Frankly, it didn’t matter if they were right or not. And in more times than I am willing to admit, I found myself in trouble for not heeding my parents’ advice. Physically. But more often, emotionally. I was just emotionally antagonistic to my own wellbeing. Something I was unwilling to admit for quite a while.

We live in an era where many debates have spiraled down the path of: “If I’m right, you’re wrong” or “If I’m wrong, you’re right.” But most issues – and I might even be as bold as to say, all issues – are not nearly as binary. Debates have become arguments rather than conversations. We fail to realize great constructive conversations are never zero sum. Socratic discussions lead to nuance and a spectrum of colors that are dimensionally vast. Many of us have chosen what is the easiest for us to swallow in that moment. That soundbites resonate more than 3-hour debate. We’ve turned our attention towards ephemeral efficiency rather than robust literacy. At the same time, we need to balance complexity with simplicity. Sometimes, matters aren’t as complicated as we make them out to be. Other times, they are and possibly more so.

Someone I deeply respect once told me. “The quality of your words are determined not by what comes out of your mouth, but by how much reaches another person’s ears.” Oddly enough, we fail to use our senses in the proportions nature gave to us. Two ears. One mouth. Yet, we often act as if we have two mouths and one ear. And I am not immune to that fact.

Over the years, due to the accumulation of scar tissue, I’ve learned to abstract who from what they are saying. When I hear advice, opinions or even facts from someone I am emotionally aloof or antagonistic with, I ask myself, if someone I deeply respect said the exact same thing, would I still be as averse as I am now?

If still so, why? What are my underlying assumptions to oppose such a claim?

Similarly, if someone I deeply respect (even blindly so) says something I agree with too quickly, would this piece of advice hold the same gravitas if it came from someone with little social capital?

Of course, the above is much easier when my inner weather isn’t hormonally turbulent. But when it is, I breathe deeply thrice. And ask myself the question again. And if still turbulent, then I repeat until I’m ready to face my own ego.

Photo by Krissana Porto on Unsplash

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

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

Posted on

#unfiltered #44 Le Raison d’Etre for Social Experiments

social experiment, curiosity

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

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

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

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

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

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

Photo by Joseph Rosales on Unsplash

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

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

Posted on

#unfiltered #43 Do I Like to Write?

writing, how to start a blog

An investor I had recently been put in touch with asked me this past Monday if I like to write. I thought it was a peculiar question at first. But it strangely kept gnawing at me as the week went on. While I can’t say for certain that it was that investor’s intention, it became a forcing function for me to reflect on my motivations.

If you’ll believe it, I used to hate writing. With a capital H. I used to dread when a teacher or professor would assign us essay prompts for homework. Many of my college and high school friends can probably attest to that fact. More so, I was the world’s best procrastinator. Ok, “best” might be overselling myself. But I had a track record for deferring my 10-/20-page essay until the night before it’s due. It was the antithesis of fun. I knew exactly what my professors sought. All I had to do was put the puzzle pieces together. Frankly, writing was a necessity to survive my academic career, not one I’d seek out as a passion.

It wasn’t always that way. In elementary school, I loved writing poetry. An exploration of my inner creativity, unrestrained by the educator’s whip. I also took part in school poetry competitions. As time went on, writing lost its sparkle, between book reports and persuasive essays.

Before this one, I started two other blogs. Neither of which lasted past three months. Both of which I started back in college. Looking back no one asked me to start a blog, much less three blogs. But looking back, I attribute each time I started a blog to the professors I had. Particularly by their rare ability to make learning fun and contagious. It was much less the content of each class, but rather, the fact that we graduated each class armed not with just answers, but with two other faculties I found indispensable over the years:

  • The ability to ask nuanced questions,
  • And the ability to find answers and questions to answer those questions.

My senior year in college I had a third catalyst for writing. As you guessed, also inspired by my professor for a class I didn’t have many expectations for when I signed up, despite hearing glowing reviews from my friends. That year I began writing in journals every day. There is no catch. There are no cheat days. We just had to ideate at least once every day. No matter how long or how short it took, once a day keeps the demons away. At the same time, outside of a promise of commitment, there were no rules. There were no rubrics. No one would grade us on how and what we wrote. Full, uncontrolled creative liberty.

It took me about three months. Slowly, but surely, the spark returned. Over time, journaling evolved into blogging. The best part is I don’t even know what the next stage of my Pokemon evolution will look like. I won’t go in depth here on how I journal these days, but if you’re curious…

Over the past year, I’ve had an increasing number of friends and readers reach out to me and ask me how writing comes so easily to me. It sure didn’t in the larger arch of my life. And not, it doesn’t… not always at least. Some days it takes longer than others. But just like how I wake up and exercise first thing in the morning, journaling is a muscle I am training every day, if not multiple times a day. Whether it’s in my journal or on my Google Keep app or on a Notion page.

That said, I think I’m far less coherent as a speaker than as a writer. I’ve had friends and mentors tell me over the years in conversation, “David, you’re not making any sense.” Unfortunately, in more occasions than I would like, I have a feeling of cognitive dissonance when speaking, which I am actively working to mend. After all, I can only hide behind the veil of asynchronicity for so long. Ironically, I’ve been engaging in more and deeper synchronous conversations than asynchronous over the course of the pandemic.

Luckily, I also haven’t gotten writer’s block yet ever since I began this blog. But there have been certain weeks where I’ve been frustrated at the quality of my journal entries. Enough so, that it never makes it onto this blog. So it goes to say, I never run out of ideas; I just sometimes run out of ideas I think are nuanced enough to share. After all, it’s why I started the #unfiltered series. George Orwell once said, “If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.”

In closing

I never started this blog with the intention of tracking viewership growth. But I’d by lying if I said I wasn’t grateful and elated to see the reception of some of my essays. On days when readers reach out and say thank you, I really believe the sky’s the limit. When I reach out to people I look up to and they mention in our conversation that they enjoy the content I write, I struggle to contain my smile.

My swim coach once asked me semi-rhetorically, “David, why d’ya like to swim?” To which he followed up and said, “You like to swim because you’ve won.” While in terms of numbers I’m still far from “winning”, this modest scope of reception so far only compounds upon my creative joy.

When I pursue any endeavor in my life, I always ask myself: Are there skills, relationships, and/or enjoyment I build that transcend the pure outcome of this endeavor? (Or two cousins of this question here and here.) For this blog, yes. And it boils down to three reasons:

  1. I write to think. It’s a process of self-discovery. On the flip side of the same token, it’s to prevent my prefrontal cortex from atrophying.
  2. Creative joy. There’s something just so satisfying when a blank canvas turns into a cohesive illustration of my mind’s entropy.
  3. And knowing that, no matter how miniscule, it’s inflected a handful of people’s lives upwards. That, and knowing that every so often, somebody out there will smile as they read this.

Photo by Aaron Burden on Unsplash

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

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

Posted on

#unfiltered #42 The Miracle that Catalyzes the Hero’s Journey

In the venture world, the word timing is thrown around in a very canonical way. Many investors and founders mythologize the concept of timing around a business. While there is some science and data that might be able to point in the general direction, success is a lagging indicator of timing. And arguably, the only way anyone can really determine if the timing is right or not is in hindsight. Investors that said they knew the exact timing of the market may just be attributing their success to survivorship bias.

To analogize it, it’s the same as knowing when to invest in the market or in a particular stock. Everyone wants to buy at the lowest, sell at the highest. Your ROI is positively correlated with the sell price, and negatively correlated with the buy price. But when is the lowest? No one really knows for certain. We can guesstimate a timeframe with reasonable confidence, but that’s the best we can do. The same is true for measuring timing in the market. Yet there is one thing that I’ve come to learn in my years in the venture world that’s as close as you can get to the “true” timing of the market. A miracle.

Let me explain.

One miracle

Every startup needs one miracle to succeed. One. No more. No less. Elad Gil said in an interview with James Currier at nfx, “Every startup needs to have a single miracle… If your startup needs zero miracles to work, it probably isn’t a defensible startup. If your startup needs multiple miracles, it probably isn’t going to work.” He further elaborates, “If you have more than one, you have compounding small odds and that means you’re very, very likely to fail.”

Before that miracle, if you’re truly creating a revolutionary business, by definition, you’re in the non-consensus. You have more non-believers than you do believers. If it were an obvious business, then everyone would do it. If everyone does it, economically-speaking, the ROI is low. In a situation, where every kid sells lemonade with the exact same recipe by the street corner, everyone is fighting for the exact same customers. Eventually, it’ll lead to a race to the bottom.

That single miracle is going to be that trial by fire. The true test of grit and founder obsession. That trial, whenever it is, predictable or not, determines if your product will stay a niche idea (and possible fizzle into obscurity) or a business that will change the world. For you and your business, that miracle could have been catalyzed by the pandemic, the GME short squeeze, ’08 recession (if you’re an older business), the inauguration, or something yet to come. The question is: How do you respond in the face of adversity?

Why is that miracle important?

Tim Ferriss once said, “Your superpower is very often right next to your wound, like your biggest wound. […] They’re often two sides of the same coin.” If you can survive and conquer that trial, the miracle – your superpower – becomes one of your strongest moats. The lessons you learned, the trust you (re)built, and the legacy you begin to construct. Those lessons – those earned secrets – while not impervious, will ideally be incredibly hard to obtain for others without walking through fire. A metamorphic journey from a vulnerable caterpillar to a beautiful monarch. What Joseph Campbell calls the “hero’s journey“.

And in the longer time horizon, that you are no longer just the protagonist of that miracle, but that you are also a producer of miracles for others. You are then capable of minting miracles systematically. Be it your customers, your team members, and your investors.

Why #unfiltered?

You might be wondering why I tagged this essay as #unfiltered. Frankly, it’s a new unrefined hypothesis that I’ve been playing around with. While it’s been inspired by others, I believe there’s more nuance I still need to uncover as well. That I’ll need to test a bit more to see if it can be a more robust thesis.

Going forward, I will continue to ask founders questions like:

  • What is the origin story of this idea?
  • If you were to fail in 18 months, what would be the most likely reason why?
  • Conversely, if you were to wildly succeed in that same time frame, what would be the biggest contributor?
  • Why are you a different person today than when you started this business? Who/what catalyzed this/these change(s)?
    • Examples of who: customers, team, partners, investors
    • Examples of what: black swan events, market trends, socio-economic habits, new technologies, an inflection point in your life when you faced impossible odds, failures, etc.

But I’ll be particularly looking for the earned secret among a miracle of adversity. Simply put, I’m looking to hear this song play in the background. The beginning of a mythical legend in the making.

Cover photo by Jon Ander on Unsplash

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

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

Posted on

#unfiltered #41 Pondering Purpose and Passion – Notes from Naval Ravikant on Clubhouse

fire, passion, purpose

I’ve been a long time fan of Naval Ravikant, so when he went on Clubhouse recently to share his thoughts, despite not having an iPhone (I know ?), I had to find a way to tune in. While Clubhouse is designed to be the ephemeral demystification of the broader world, there are a rarified few conversations I believe are and should be evergreen. Naval’s happens to be one of them. Whether Clubhouse itself compiles these knowledge banks or through some third-party service, we already have listeners and Clubhouse users recording these conversations. A temporary hack that paves the way for a broader solution.

Over the weekend, I found Naval’s definition of purpose to be one of the best I’ve heard to date:

“You have to live up to your own moral code. Your life is an eternal single-player game. You’re not competing against anybody else; you’re competing against yourself. You set your own desires and your goals. You have your own perspective. You have your own morality. And you have to live up to it.

“There is no standard meaning or purpose. If there was a single purpose or meaning for all of us, then we’d all be slaves to that single purpose. We’d all be robots – every one of us fighting each other in conflict to get to that one purpose. And there’s not even a single purpose for you necessarily, other than the one that you create. So, you get to create your meaning and purpose. You get to craft your own story here. […]

“It is a race, but you’re just running against yourself. You pick the finish line; you pick the goal line; you pick the meaning; you pick the purpose. So you can pick a meaning or purpose that is antithetical to happiness, or one that aligns with it.”

A month ago, my friend and I watched Pixar’s Soul. In it, the writers illustrated a powerful lesson on life’s inspiration. As Jerry enlightens Joe, that distilling your whole life into a singular purpose is “so basic”, Joe enlightens Soul 22, “your spark isn’t your purpose. The last box fills in when you’re ready to come live.” To live means to enjoy and savor every minute, every second, the entire 24-hour day, all 365 days of the year, and every year we are alive and breathing. Not just, and I’m generalizing here, the 40-100-hour workweeks. Joy and purpose, after all, was never meant to measured as a unit of time alone.

Many of us live life looking for our purpose in life – a singular destination. A singular raison d’être. We compartmentalize our entire lives into self-prescribed labels. In high school, it was either by our grades or our extracurriculars. In college, by our majors. In our adult life, by our job title. I can’t speak for everyone, but I’m willing to bet that most, if not all people, are more robust than just their full-time roles make them out to be. Just like I’m more than a VC Scout. That’s why I’m so fascinated by polymaths in our society.

In opening our minds to a world beyond a single degree of freedom, we give ourselves more surface area to find inspiration and happiness. As Tim Ferriss once said, “It is not that beauty is hard to find; it’s that it is easy to overlook.”

Equally so, his rhetoric on passion is equally as provocative. Or specifically, the relationship between your passion/obsession (more on obsession here and here) and domain expertise. The latter, as Naval calls it, “specific knowledge”:

“How do you gain specific knowledge? It’s almost a catch 22. Specific knowledge is built up by you through your passions. So, when they say follow your passion, it’s kind of what they mean. It doesn’t always lead to money, but it can. Because if you’re obsessive about something and learning it for your own genuine intellectual curiosity – not to get a degree, not to make money, not to impress your friends – you’re going to end being better at it than anybody else. So, I really believe that you should only read and engage in activities that you genuinely enjoy. And you should cultivate your intellectual obsessions without any goal that you may be surprised when you look back and connect the dots later that one of them developed into a goal. One of the hallmarks of specific knowledge is that it will feel like play to you, but it will look like work to others. So, anything that fits that model, you should develop. […]

“You get what you want out of life. You just have to want it badly enough. If it’s your all-consuming desire, you will get it. You will create the path to the destination no matter what it takes.”

Naval’s encyclopedic answers asked underscored once again a question I ask myself when I am the most lost:

What would I do if, at the end of the day, I would be only one applauding myself?

Photo by Almos Bechtold on Unsplash

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

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

Proudly powered by WordPress