Category: Ideas/Creativity

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#unfiltered #53 A Different Way To Count

I have this conception of a personal Hall of Fame. For every piece of content, individual, and or experience in my life that has drastically changed the way I live or the way I think about life. Upon entrance, I find myself facing three large corridors – each adorned with text in Garamond font, framed in the corpse of a giant oak tree. In the corridor to the left, it’s the “Content Hall”. Arguably, the most competitive of the three halls to get into.

I only meet so many individuals in my life. I would say somewhere on the magnitude of tens of thousands. To pick tens of individuals among 10,000 is a 0.1-0.2% chance of induction.

The same is true for experiences. Excluding my daily habits of sleeping, eating, and others that have become second nature, there are very few extraordinary experiences among the ordinary. And in pursuing something extraordinary over a prolonged duration, that something extraordinary becomes ordinary to you. So, over time, you end up regressing into a step-wise function of finding the extraordinary in the extraordinary. To choose from a select few of these extraordinary in the extraordinary experiences at various learning curve spurts leaves an even smaller sample size.

Yet the same can’t be said for content. We consume a plethora of content on a daily basis. From obvious content drops, like YouTube, books, shows, and podcasts, to the non-obvious, such as emails, conversations, street signs, and opportunities that make you pause in the buzz of daily life. With tons of constant inputs from multi-directional sources, picking the handful that has altered your life’s course has a far lower acceptance rate than being struck by lightning.

For me, one of the greatest pieces that exists in my “Content Hall” is The Tail End by Tim Urban. There are a multitude of great anecdotes in it, but my favorite of which is, by the time we turn 18 years old, we’d already have spent at least 90% of our time with our parents.

Presidents

Say I live to 90 years old. In my lifetime, I get to see 22 US presidential terms. 22 presidents max, but many presidents hold office for two terms rather than just one term. There’ve been 46 presidents in the history of the United States so far. 21 of which served two terms. For ease of calculation, there’s about a 50% chance that any president will hold office for two terms. That’s 16 presidents, give or take, throughout my entire life. I’ve lived through Bill Clinton, George W. Bush, Barack Obama, Donald Trump, and now Joe Biden. That’s 5, and only 11 more to go. Of course there’s the chance of early impeachment. But let’s assume everyone serves their full term.

I’m 25 now. So, I’ve already seen almost a third of the presidents I will see in my lifetime.

Summer vacations

If I live till 90, I have another 65 summers to go. 65 summer vacations left.

If I settle down by 35, I have 10 more summer vacations left – entirely free from constraints and in my prime. I can go skydiving and play extreme sports, without having to worry about seeing the chiropractor. And I imagine, like many others out there, I have more than 10 summer vacation spots I want to hit, excluding the ones I want to have repeat visits to. I already wish I had more time.

Times I’m wrong

In preparing for this essay, for the past week, I tracked the number of times I realized I was wrong. Racking the numbers up each day for seven days. From getting the weather wrong to forgetting what I thought we had for leftovers to being one digit off on my recollection of industry metrics during a meeting, I make on average two small mistakes a day. Extrapolating that to the rest of my life, I have almost 47,500 more small mistakes left to make. I’ve never felt more human than I do now.

Of course, the above number doesn’t include all the times I’ve realized I was wrong after the fact, which I imagine accounts for a mountain of imperfections in its own right. Enough to rival the Great Pacific Garbage Patch.

Idea journals

Many of you reading this blog are no stranger to my idea journals. I go through a journal every four months. I have almost 200 more idea journals to go through, assuming I keep at the pace I’m going at now. 195, to be exact. Oh wow, I really need to invest in some shelf space in my future homes. Enough for over 20,000 pages and all hardcover leather-bound journals.

Breakdowns

Each time I conquer a mental breakdown I think I’d be more resilient. In many ways, I am right. In many more, I am still unprepared for what is to come. Just as the sun rises, I too will cognitively readjust to my stress levels. While I wouldn’t describe my breakdowns to be on regular intervals, on average, it seems to happen once every five years. At least a major one, discounting all the smaller frustrating moments I come across. That’s 18 total, and 13 more mental shifts I won’t be ready for no matter how much I prepare.

In closing

All the above calculations were in the scope of 90 years old. But the awesome part is if I live past 90, every day will be icing on the cake. It’ll be better bang for my buck!

The point of this mental shift isn’t to be 100% accurate (’cause I know I’ve made quite a few generalizations). But rather reframe how we choose to live our lives.

In comparison with the hundreds of thousands of years the human species has lived, we are mere century inhabitants. And in the whole history of Earth, if we were to count on a 24-hour clock where the formation of Earth began at time 00:00:00, humans have lived just over a minute. We have short lives. Maybe that’ll change some time in our lifetime, with technology, CRISPR, or some sci-fi derivation.

But that doesn’t mean we can’t live fulfilling lives. Or as Garry Tan puts it, most people are “short term optimists” and “long term pessimists” and end up picking smaller problems to tackle. Rather, we gotta be “short term pessimists” and “long term optimists.” We have short lives, but let’s live a life where our impact lasts beyond our physical lifespan.

Making every second count,

David

Photo by Djim Loic 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.

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#unfiltered #51 The Fickle Jar

pickle jar, fickle jar

I’m promiscuous… with ideas.

Many of my friends are no stranger to the ephemeral nature of my creative outbursts. Some of these ideas are whimsical in nature. Where, from the start, they carried no real weight behind their punch. A deplorable few collected dust in the attic, as a product of giving myself the time to think twice. To second-guess myself. In fact, partly due to being in VC, I became quite proficient at saying “No.” I was so good at saying “No” that I forgot how to say “Yes”. And as I wrote before, the theme of this year is to say “Yes” to more opportunities to experience growing pains. So, when my friend brought up something she used to track things she repeatedly says “Yes”, then “No” to, I was intrigued. She called it her fickle jar. And of course, I had to ask.

Both she and I share common ground. In the sense, that we happen to be promiscuous when it comes to ideas. We mint and host a multitude of ideas. But often don’t give most of our thoughts a double take before we abandon them. They retire from our lips before they have an opportunity to marinate in our minds.

So both of us needed this fickle jar. The fickle jar is a jar chronicling everything you might be fickle on. Soft commitments of “I should do X.” Or “It’d be cool to do Y”. It’s a visualization of the loose promises you make to yourself. Every time you think of a something you want to or should do, write it down. Draw it in its own bubble. Each idea isolated from the next – though some might be related. And each time you follow through and act on the idea, you color your bubble in. When you finish a jar, make another one. Over time, you can visually see what your creativity to commitment ratio is.

Over the next few months to years, I know I’ll accumulate enough fickle jars to have my own fermentation station in my basement. The goal of all of this is to visually track my partiality between creativity and commitment. But moreover, to emphasize intentionality. In the event I propose an idea – which is inevitable – it’s not a fleeting thought. And those of a less ephemeral nature, I take it and give it a go, regardless of the outcome. Hesitation has always been the enemy of my progress. Ideally, over time, I commit to most ideas that spring up. But realistically, I know it isn’t possible. Neither should it be a priority.

Yesterday morning, I was reading First Round’s interview with Irving Fain, co-founder of Bowery Farming, who recently announced their $300M Series C round. While not your first-time founder, having built CrowdTwist (acq. Oracle) and iHeartRadio, with Bowery, he, nevertheless, jumped into an industry he knew little about.

“I could sit on a chair and think my way around this problem for another decade, but when building a company, you never avoid that moment where you have to jump off the cliff. In some respects, what you want to try to make the cliff-to-ground ratio as small as you can. But there is no amount of work and research that avoids the fact that at some point you’re jumping off into the abyss.” So like Irving, I need to have the nerve to jump into the abyss – at least more so than the status quo. I just have to say “yes” to the genre of ideas that have historically left me in decision paralysis.

Fain goes on to say, “Before I started my first company, I spent enormous amounts of time evaluating, evaluating, evaluating, saying no, and evaluating, evaluating, evaluating, and saying no. And in hindsight, I look back and say, ‘Wow, I said no to some great ideas.’ I spent way too much time getting to the wrong answer, arguably.”

I recently realized that some of the biggest risks I ended up taking is spending undue time amidst inaction. The risk is the opportunity cost of the time I could be spending elsewhere. Yet I choose indecision – an infertile stalemate. Crops won’t grow if the soil hasn’t been tilled.

She also noted, “Fickle also rhymes with pickle.”

Ironically, this essay almost became a fickle pickle ’cause I was too lazy to transcribe my fickle jar.

fickle jar
My fickle pickle jar

Cover photo by Reka Biro-Horvath on Unsplash

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

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

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Expert + Reasonable + Crazy Idea = Crazy Good

The amazing Paul “PG” Graham came out with an essay this month on crazy new ideas. And the thing I’ve learned over the years, being in Silicon Valley, is if PG writes, you read. In it, one section in particular stood out:

“Most implausible-sounding ideas are in fact bad and could be safely dismissed. But not when they’re proposed by reasonable domain experts. If the person proposing the idea is reasonable, then they know how implausible it sounds. And yet they’re proposing it anyway. That suggests they know something you don’t. And if they have deep domain expertise, that’s probably the source of it.

“Such ideas are not merely unsafe to dismiss, but disproportionately likely to be interesting.”

I’ve written a number of essays about crazy ideas. Here. Also here. The last of which you’ll need to Ctrl F “crazy”, if you don’t want to read through all of it. And also, most recently, here. But that’s besides the point. The common theme between all of these is that crazy ideas are not hard to come by. Crazy good ideas are. Good implies that you’re right when everyone else thinks you’re crazy. When you’re in the minority. And the smaller of the minority you are in, the greater the margin on the upside. Potential upside, to be fair.

As investors, we hear crazy pitches every so often. David Cowan at Bessemer even wrote a satire on it all. For the crazy pitches, go to episode five. The question is: How do we differentiate the crazy ideas from the crazy good ideas? But as PG says, if it’s coming from someone we know is a subject-matter expert (SME) and they’re usually grounded on logic and reasoning, then we spend time listening. Asking questions. And listening. ‘Cause they most likely know something we don’t.

That was true for Brian Armstrong, who recently brought his company, Coinbase, public. He worked on fraud detection for Airbnb in its early days prior. And he knew he was getting into the deep end with crypto back in 2012. But he realized how unscalable crypto transactions were and how frustrated he was. Garry Tan, then at YC and part-time at Initialized, saw exactly that in him. A reasonable SME with a crazy idea. Garry just released an amazing interview between him and Brian too, if you want to tune into the full story.

What if some of the variables in the equation are missing?

But most of the time the founders you’re talking to aren’t subject-matter experts with deep domain expertise. Or at least, they haven’t left an online breadcrumb trail of whether they’re a thought leader or if they’re reasonable human beings. So subsequently, in the little time I have with founders in a first or second meeting, I look for proxies.

For proxies on domain expertise, I go back to first principles. What are the underlying assumptions you are making? Why are they true? How did you arrive at them? What are the growing trends (i.e. market, economic, social, tech, etc.) that have primed your startup to succeed in the market? Does timing work out?

To see if they’re “reasonable” under PG’s definition, I seek creative conflict. How do you disagree with people? If I brought in a contrarian opinion you don’t agree with, how do you enlighten me? How do you disagree with your co-founders?

In closing

To be fair, we’re not always right. In fact, we’re rarely right. On average, in a hypothetical portfolio of 10 startups, five to six go to zero. One to two break even. Another one to two make a 2-3x on investment. That is to say, they return to the investor $2-3 for every $1 invested. And hopefully, one, just one, kills it, and becomes that fund returner. Fund returner – what we call an investment that returns the whole fund and maybe more. Of course, every time a VC invests, they’re aiming for the fences every time. As a VC once told me, “it’s not about the batting average but the magnitude of the home runs you hit.” And even in those 10 investments, it’s a stretch to say that all of them are “crazy” ideas.

But the hope is that even if we’re wrong on the idea, we’re right on the people.

Photo by Àlex Rodriguez on Unsplash

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Creativity is a Luxury

“Creativity is a residue of time wasted.”

I recently came across the above quote – the attribution to Einstein. And I found it extremely prescient. In the world last year. And in the years ahead.

Creativity is the ability to find inner peace in a busy world. To weave cacophony into symphony. The ability to recognize and chart patterns between the pixels and decibels around us. A guiding, focusing, and metaphorical – and I mean metaphorical in its truest form – principle that abstracts you from the literal shackles of your current situation. Now before I get to abstract…

I’ve written about where I find my inspiration on numerous occasions, including while I’m:

  • Exercising
  • Driving
  • Cooking
  • Showering
  • Listening to podcasts
  • Washing the dishes

… just to name a few. In each of the above, I give myself the intellectual bandwidth and the time to ponder. Simply ponder. With no goal or predestination in mind. Frankly, this blog is a product of such intellectual adventures.

And I know I’m not alone. In the world coming out of the pandemic, this may cause a new revolution of creativity.

Our grassroots

Hundreds of thousands of years ago, we transitioned from a nomadic to a more specialized lifestyle. The transition to specialized roles in a hunter-gatherer society allowed hominids to share the responsibility of survival. As we learn in the basics of economics, economies that have comparative advantages who trade can create a larger global supply of goods and services. In this case, it was the cooperation among the citizens of the same society that freed individuals’ bandwidths to explore other interests, including, but not limited to:

  • Controlled use of fire
  • Adaptability to colder climates
  • Specialized hunting tools, like fishhooks, bow and arrows, harpoons and bone and ivory needles
  • Intricate knowledge of edible plants

While hand-built shelters likely go as far back as 400,000 years ago, and huts made of wood, rock and bone as far back as 50,000 years ago, it wasn’t until the Neolithic Revolution that agricultural culture became a permanent habitual change. In the emergence of an agricultural lifestyle, humans now freed up time they would have otherwise spent on migration or hunting. And with that same free time, they invented more creative means of living, not just survival, like the means to combat disease and increased agricultural knowledge. Economists Douglass North and Robert Paul Thomas call this Neolithic Revolution the “first economic revolution“. The two state this was the result of “a decline in the productivity of labour in hunting, a rise in the productivity of labour in agriculture, or [an] … expansion of the size of the labour-force”.

Maslow’s Hierarchy

If we look at Maslow’s Hierarchy of Needs, the evolution of free time, and therefore creativity, makes complete sense. Psychologist Abraham Maslow wrote in 1943 that humans make decisions motivated five tiers of psychological needs.

Maslow’s Hierarchy of Needs

A person’s most basic, tangible needs are at the bottom, whereas the intangibles reside at the top. And according to Maslow, you cannot begin to fathom the higher echelons of your needs, like esteem and self-actualization, until you’ve fulfilled the tiers underneath. Maslow also calls self-actualization “growth needs” and the lower tiers “deficiency needs”. In a very real sense, when you’re struggling to find food and shelter or job security, you don’t have the mental capacity or free time to entertain how high your potential can go. Time, specifically leisure time, is a luxury for people who have fulfilled all their deficiency needs. And that leisure time is what creatives need.

Asking the best

Of course if I was to write anything on creativity, I had to ask my buddy, DJ Welch (IG, LI) – one of the most creative minds I know. Not only did he grow his YouTube channel to 370,000 subscribers in less than three years, he was also an artist for Lucasfilm, Instagram, Cartoon Network and more. Now, he’s working on a new project – Primoral Descent – one that I’ve been excited for the public to finally see.

“As a child, my parents let me have a lot of free time. They let me make my own choices. They let me be imaginative. That’s when you come up with innovation. Creativity is a river above everyone’s head.”

When I asked him to unpack that, he said, “Good ideas are gifts from the universe – fish that swim in that river. All you have to do is learn how to reach up and fish for them. And just like fishing, if you stick around long enough – if you’re patient enough, you’ll be able to catch a few. But you never know what fish you’ll reel in. Just that you will.”

Toys for adults

We see the same with entrepreneurs and creatives. They have time to think. Time to reach into that river and pull out an idea. They are investors and the medium of investment is their time. In fact, you can argue they’ve dedicated almost every waking hour to optimize themselves to offer a creative solution or perspective into the market. They’ve made it their job to be innovative. After all, innovation, by definition, is a creative solution. Under Einstein’s definition, we could call them professional time wasters.

As Chris Dixon says, “The next big thing will start out looking like a toy.” Today, we see the rise of NFTs, VR/AR, content creation, e-sports, and much more. Not too long ago, we had the telephone, and eventually the smartphone, as well as the internet. All of which had their origins as toys. And I know I’m only scratching the surface here. In order to have time to create toys, or for that matter, even play with toys, you need leisure time.

With that same time, more and more people are pursuing their interests and passions, creating, what Li Jin at Atelier Ventures dubbed, the “passion economy“. Similarly, more people are dabbling into new hobbies. In the pandemic, the average person saved 28 minutes of time that would have been spent on going to work. An hour on average for the round trip. Some people used that time saved to get more work done. Others used their time saved to discover new passions – be it baking, starting a podcast, hiking, or gaming. For many Americans, that extra time was paired with stimulus checks and communities coming together to cause political and economic shifts – for better or worse.

As Tal Shachar, former Chief Digital Officer at Immortals, said, “The next big thing in 2021 is the YOLO economy. Consumers will be more open to trying new products/services and spending on novel experiences, particularly with friends, as we emerge from the pandemic with pent up demand and few routines.” In the process of trying, you will inevitably uncover more surface area to expand on.

In closing

In 2021 and onwards, as entrepreneurship and solo-preneurship lowers its barriers to entry, we’re lowering the Gini Index equivalent for creativity. More people will have increased access to time – time to self-actualize. Time to challenge our status quo.

I love this line in Kevin Kelly‘s “99 Additional Bits of Unsolicited Advice“: “The greatest rewards come from working on something that nobody has a name for. If you possibly can, work where there are no words for what you do.” If you can succinctly describe what you’re working on, then you’re not really pushing the envelope.

Later in that same essay, Kelly writes, “A multitude of bad ideas is necessary for one good idea.” And to have ideas, you need time. As DJ and I were wrapping up our conversation, I asked, “So, DJ, how do you optimize for creative moments?”

And he responded with some great food for thought. “I nap. Sleeping is how I process information. As I go lay down for a nap, right in that lucid moment, I come up with my ideas. I quickly scribble them down, then go back to sleep. When I finally wake up, I go work on them. The great Winston Churchill’s naps were a non-negotiable part of his day. In fact, during WWII, he had a bed set up in the War Rooms so he could take his daily afternoon naps. Similarly, I often take 20-minute power naps around 2-3PM. And I’ve never pulled all-nighters. Thinking isn’t hard for me. Thinking is the part ‘efficient people’ [who work straight through the day] get stuck on.”

Cover Photo by Jr Korpa on Unsplash

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Losing is Winning w/ Jeep Kline, General Partner at Translational Partners and Venture Partner at MrPink VC

“I was a swimmer since I was very young and, you know, I never won. I never won.”

You’re probably assuming this is how the opening scene of a movie about a future world-champion swimmer begins. The beginning of the world’s most amazing underdog story. And you’re wrong. Well, not completely wrong. This isn’t a story about the world’s next biggest Olympic swimmer. Although it might be well-timed with the Tokyo Olympics around the corner. This… is a story, in my humble opinion, of one of the world’s next biggest venture capitalists. A story of a young Bangkok girl who became a VC from learning how to lose.

I’ve never been the smartest kid on the block. At least in the IQ department. So I make it my mission to hang out with folks who are smarter and more driven than I am. Jeep is no exception. I met her last month. And as if going from a World Bank economist to Intel leadership to startup advisor and investor to lecturing at UC Berkeley’s Haas School of Business was not enough, in our first conversation, she shared an incredible set of contrarian insights. So earlier this month, I had to jump into another conversation with her.

Something about going long

If you’re a long-time fan of this blog, you know one of my favorite Bezos-isms is, “If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few companies are willing to do that.”

Jeep is that same kind of superhuman.

“I started as a competitive swimmer since I was seven, and I swam so much and so hard, like three kilometers a day. It’s just a lot of practicing. I never even won a medal. And I kept doing it. And that was hard.

“Because other kids they got medals in different styles. So I learned early on in life what losing actually meant. And I think that’s very important because a lot of smart kids, they never learn how to fail early on in their life. And it’s kind of like a winner’s curse because you know, when they’re the best at everything, since they were young, throughout college , once they come out, and they realize that the world is hard, they are doing things or want to pursue a career that their parents cannot help them, they become risk averse. Meaning they don’t want to try new things.

“So I never won in [any] swimming competitions. Until I got into college. When I got into college, at the time I already quit swimming. I quit in high school. So, I didn’t swim competitively anymore since I didn’t have time to practice. I picked up other activities like piano, which I came to love. In college, one of my friends asked me, ‘Hey Jeep, why don’t you come back to the competition?’ And she knew I never won. We were in the same race at so many events. And I said, ‘I don’t know. Let me try.’ So I tried again.

“So I got back to the practice routine. Adjust my strokes a little bit. And then I won. I got gold and silver medals for a college swimming competition. And I was like, ‘This is a joke. How could I win?’

I never won ever, like for ten some years. And I joke with my friend, ‘You know why, because everybody else quit!’ They quit about the same age in high school.

I just went for it. And that was one of the moments in life that I realized that it’s all about grit. You do what you love and you don’t quit. There will be a moment that you win.”

The analogy extends further

“Failure is the mother of success.” It’s an ancient Chinese proverb that my mom used to tell me again and again growing up. Every time I “failed.” Scored low on a test. Embarrassed myself on stage for a school musical. Placed fourth, right off the podium for multiple competitions. It’s funny thinking about it in retrospect since she turned out to be the exact antithesis of a stereotypical Asian parent. And I love it!

Take tbh, an app where you send your friends anonymous compliments, as an example. It launched back in late 2017. 73 days after its launch, it went from zero to 2.5 million daily active users, which subsequently led to a $100M acquisition by Facebook. To many, tbh looked like an overnight success. But it wasn’t. Nikita Bier, co-founder of tbh, and his team spent seven years with 15 failed products before they arrived at tbh. And with each iteration, they learned and compounded their lessons from their previous failure.

Clubhouse’s Paul Davison and Rohan Seth is another example of a seemingly overnight success. From Talkshow to Highlight (acq. Pinterest), the pair went through at least nine failed apps before they arrive at Clubhouse – last reported to have passed 10 million users. And valued at $4 billion. Their lead investor, Andrew Chen at a16z, spent eight years getting to know Paul.

One of my junior swim teammates told me years ago when I was at my prime, “David, I don’t think I can beat you as you are now. But I promise you I will beat you one day, even if that means after you retire.” At the time, I dismissed it as just another snarky comment, which athletes are prone to make from time to time. But now that I’m a bit wiser than I was in high school, I find that same comment incredibly prescient. It just so happened that a few years ago, we raced each other again. Both of us had long exited the competitive arena, and he won.

In closing

Near the end of our conversation, Jeep cited something Soichiro Honda, the namesake for the Honda Motor Company, once said. “Success can be achieved only through repeated failure and introspection. In fact, success represents 1% of your work which results only from the 99% that is called failure. Many people dream of success. To me success can be achieved only through repeated failure and introspection. In fact, success represents 1% of your work which results only from the 99% that is called failure.”

She further elaborated, “For people who grew up in a society, in a culture that does not easily accept failure, I want them to know that it’s actually not a bad thing to try and hear rejection. But along the way, they have to make sure that they learn.

“It’s the same thing when I teach UC-Berkeley students. I told my brilliant graduate MBA students that there is, for me – and it’s true – there is no stupid question. If other people think your question is stupid, but at least you learn. If you learn, there’s no stupid question. Do not ask good questions, if it means you don’t learn anything.”

In a way, I’m reminded of a peculiar quote by Karl Popper, “Good tests kill flawed theories; we remain alive to guess again.” While Popper was known to be quite the contrarian thinker of his day, the same seems to hold for questions. Good questions kill flawed theories. We remain alive to learn again. After all, speaking from personal experience, I often find myself burning the midnight oil to ask the perfect question. But in the pursuit of asking the “perfect question”, I’ve forgone the adventures I would have had to arrive at the answer I thought I sought.

We learn when we fail. We learn, to one day succeed. The greatest are the greatest because they have a higher propensity to fail than the average person. As the great Winston Churchill said, “Success consists of going from failure to failure without loss of enthusiasm.”

And as Jeep said, “Winning is actually losing, but learning along the way.”

Thanks Jeep for helping with earlier draft edits!

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#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!

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The Fastest Way to Test a Startup Idea

Last week, I reconnected with Shuo, founding partner of IOVC, and one of the first people I reached out to when I began my career in venture. That day, I asked her a pretty stupid question, “Given the rise of solo capitalists, rolling funds, equity crowdfunding, and the democratization of capital, do you think now’s a good time to raise a fund?“

She replied, “I don’t know. It could be a good time now. It could be a good time five years from now. If you’re set on sticking around for the long term, it really doesn’t matter. ‘Cause whether it’s a good time or not, you’re going to be raising a fund regardless. So just do it.”

Not gonna lie, it was serious wake-up call. While I was initially looking for her perspective on the changing venture market, what she said was right. If you’re set on doing something, say starting a fund or a business, the “right time” to start is irrelevant. The world around us changes so much so frequently. We only know when’s the right time in hindsight. So focus on what we can control. Which is starting and doing.

So as an aspiring founder, which idea do you start with? And how do you test it?

Starting a business is scary

Starting a business is scary for most people. And well, the government doesn’t always make it easy to do so. Just like what WordPress and Squarespace did for websites, you have companies, like Stripe (and their Stripe Atlas), Square, Shopify, Kickstarter, just to name a few, streamlining the whole process for entrepreneurship. For an aspiring entrepreneur, not only is it taking that leap of faith, before you begin, there’s a slew of things you have to worry about:

  • Figure out how to incorporate your business (C-corp, LLC, or S-corp),
  • Assign directors and officers to your business,
  • Buy the stock, so you actually own your stock,
  • Learn to file your taxes (multiple forms, including your 83(b) election),
  • When you raise funding, get a 409A valuation,
  • And that’s just the beginning.

Of course for the above, do consult with your professional lawyer and accountant. It’s two of the few startup expenses I really recommend not skimping on. While the purpose of this post isn’t designed to solve all the documents you’ll have to go through in starting a business, hopefully, this will help with one front – taking that leap of faith. Specifically finding early validation for your idea.

The superpower of writing

I stumbled on Max Nussenbaum‘s, who’s leading On Deck‘s Writing Fellowship, provocative tweetstorm:

He boils it down to, effectively, four reasons:

  1. You can test the validity of an idea faster by writing than with code.
  2. Writing well trains your ability to sell.
  3. Publishing regularly gets you comfortable with shipping early and often.
    • To which he cited one of my favorite Reid-isms: “If you’re not embarrassed by the first version of your product, you’ve launched too late.” – Reid Hoffman
  4. Writing is easier for most people to pick up than coding.

There’s a “5th reason” as well, but I’ll let you uncover that yourself. Talk about creativity. Side note. Max created one of my favorite personal websites to date.

Much like Max, I write to think. And in sharing my raw thoughts outside of the world of startups via the #unfiltered series, often far from perfect, as well as my take in this fast-changing universe, my cadence of writing twice a week has forced my brain to be accustomed to the velocity of growth. In the sense, I better be learning and fact-checking my growth week over week. Over time, I’ve developed my own mental model of finding idea and content catalysts.

Of course, if you know me, I just had to reach out. Particularly around the third point in his tweetstorm.

What mental models or practices did he use to help him wrestle with his embarrassment from his own writing? And he replied with two loci that provided so much more context:

  1. “Reading other writers who open up way more than I do, which makes what I’m doing feel easy by comparison. Two favorites I’d recommend are Haley Nahman and Ava from Bookbear Express.”
    • And another I binged for an hour last night. Talk about counterintuitive lessons. My favorites so far are Stephen’s 12th and 16th issue. You might not agree with everything, but he really does challenge your thinking. Thank you Max for the rec.
  2. “Publicly committing to writing weekly and finding that the embarrassment of publishing was outweighed by the embarrassment I’d feel if I missed a week. Also, like all things, I’ve found it very much gets easier with practice.”

Why not both?

Then again, why not both? I go back to Guillaume‘s, founder of lemlist, recent LinkedIn post. He says:

And he’s completely right. If I were to analogize…

Writer = common
Writer + coder = uncommon
And… writer + coder + X = holy grail

You don’t have to own one unique skill. And in this day in age, there aren’t that many individually unique skills out there that haven’t been ‘discovered’ yet. Rather than search for the singularly unique skill that you can acquire, I’d place a larger bet on a combination of skill sets that can make you unique. As a founder, test your ideas early with writing. If there’s evidence of it sticking, build it with code. And it doesn’t just to be just writing and code, whatever set of skills you can acquire more quickly and deeper with the circumstances and experiences you have. Even better if there’s a positive flywheel effect between your skills.

In closing

There’s a Chinese proverb that goes something along the lines of, “The best time to plant a tree was 20 years ago. The second best time is now.” And it circles back to Reid’s quote that Max cited, “If you’re not embarrassed by the first version of your product, you’ve launched too late.” As an entrepreneur, or as an emerging fund manager, it’s a given you’re going to mess things up. But all the time fretting around at the starting line is time better spent stumbling and standing back up.

I followed up with Shuo after our call, and she elaborated a bit more, “In all honesty, you can argue now is a good time (a lot of capital available for good managers) or a bad time (valuations are frothy), but in the long-term, these variables even out and it’s how you add value as an investor that’s most important.”

If I were to liken that same insight to aspiring entrepreneurs… Yes, investors look for timing. And yes, understanding the timing of the market is important, when you’re launching a product that will revolutionize the way we live in a fundamental way. But that boils down to which idea you plan to pursue. But if you’re looking to be a founder, it’s finding that overlap in the 3-way Venn diagram between (1) what the market needs and (2) where you, as the founder, can provide the most value. And (3) where your competitors are not maximizing their potential in.

For many aspiring founders, that first step can be practicing the art of writing. Writing for clarity. Writing to practice selling. Learning to ship early and embracing imperfection. Frankly, it’s also something I need to get better at myself.

Though I’m not a religious fellow, I’m reminded of a quote from Jesus’ teaching, which I first found in Jerry Colonna’s book, Reboot. “If you bring forth what is in you, what is in you will save you. If you do not bring forth what is in you, what is in you will destroy you.” Writing is that act of bringing forth what is in you. And well, if you’re like me, I often find my greatest regrets come from a lack of action rather than in taking action.

If you’re looking for a place to start…

Top photo by Cathryn Lavery on Unsplash

Thank you Shuo and Max for reviewing early drafts of this essay.

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

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#unfiltered #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!

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#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!

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#unfiltered #40 Questions That Hone Your Emotional Fitness

As I’m gearing up for a few projects, I spent the last few weeks pondering on a number of questions. And to stress test those questions, I spent the greater half of that time asking the people around me. But in the process of doing so, I found 10 of the above questions sponsored the most self-inquiry within myself and others.

The Questions

Elad Gil, legendary angel investor, said in an interview late last year that “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.” Was there a defining miracle, when preparation met opportunity, that got you to where you are today?

Similarly: Life is some percent skill and effort and some percent of luck. How much has luck contributed to get you to where you are today?

In 2005, a Yahoo! Exec once told the Alexis Ohanian, founder of Reddit, that they were a “rounding error” which Alexis then framed on the company wall as motivation. Have there been chapters of your life that were defined by strong opposition – externally or internally – and your ambition to prove them wrong?

Pat Riley, Hall of Famer basketball coach, wrote in his book, The Winner Within, “You don’t wanna be the best at what you do; you wanna be the only one who does what you do.” What skills, experience, or mental models do you have where you are the only person – or in extremely rarified air – who can do what you do?

Quoting Jerry Colonna in his book Reboot, how are you complicit in creating the conditions you say you don’t want?

Norman Vincent Peale, author of the bestseller, The Power of Positive Thinking, once said, “Shoot for the moon. Even if you miss, you’ll land among the stars.” Entrepreneurs are people who pursue impossible odds and enjoy the journey of shooting for the moon to become world-class athletes. Telling them no is like telling a 7-year old they can’t become an NBA All-Star. Odds are they’re not going to succeed, but the process of pursuing that goal makes it worthwhile. And in doing so, they become a stronger, more resilient individual than never trying to pursue it in the first place. In your life, what have you done or would you do regardless of the outcome of the pursuit?

Andy Rachleff, founder of Wealthfront and Benchmark, once said in an interview: “If we’re batting a thousand or close to a thousand, we’ve done a really poor job.” If your probability of success is really high, the likelihood of a big win is extremely low. To win and not just focus on not losing, you have to take big risks. And as per the definition of risk, you’re more likely to fail. Have you had a failure in your life that contributed the most to where you are today?

On the same token, have there been alleged setbacks turned out to be a blessings in disguise? Or, were there “misfortunes” that turned out to be fortunes?

Let’s say life is a game blackjack. If the first card you drew represents your journey prior to 2020 – face up – and the second card exemplifies your life from 2020 till now – face down, which two cards did you draw? And would you continue “hitting” knowing the hand you’re dealt?

I saw in a Quora thread once, “When you are happy you enjoy the music, but when you are sad you understand the lyrics.” When you were in your lowest of lows, were there words, phrases, or lessons that had profoundly new meaning to them?

Desmond Tutu, who won the Nobel Peace Prize in 1984, once said, “My humanity is bound up in yours, for we can only be human together.” So, to borrow his words, what are the common themes between moments you’ve given up your humanity, either individually or collectively?

What is the narrative that you find most compelling when your inner weather is the most turbulent?

Photo by Johannes Plenio on Unsplash

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

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

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