Tag: art

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#unfiltered #72 The Purpose of My Writing

hug, console

“Art is to console those who are broken by life.” — Van Gogh

An investor I deeply respect recently told me, I am “really good” at long-form writing. Admittedly, even writing the sentence just before leaves me just as squirmy as when he first said it. I am of course genuinely grateful for the compliment. But my childhood prevents from fully appreciating and accepting a kind compliment.

Rather than having a practiced eye for structure and prose — which I’m sure the real linguists and writers will have much to critique on my lack thereof… for me, I can’t imagine a world where I can boil down distinct and nuanced thoughts from multiple sources in one tweet. Which could mean three things:

  1. I was never great at writing college apps.
  2. I am terrible at Twitter.
  3. I have trouble saying No to people and options.

Don’t get me wrong. There are many things out there are best expressed simply — that need no further elaboration. My blogposts on 99 pieces of unsolicited advice are examples of such. One for investors. One for founders.

Nevertheless, longer form writing helps me think. My mind is often a mess, and sometimes I wonder how I make it by with a mind that looks like the inside of an average college boy’s dorm room. It is most evidenced when I speak, but least explicit when I write. I have time to mull over thoughts. I have time to realize that not every thought, idea, Eureka! moment is a productive one.

I apologize if I seem smarter than I am. I’m not. I’m just another person looking to learn my way through life. Curious enough to know I am lacking, but confident enough knowing I can get there. When confidence in my self-worth wanes, I find solace and therapy in the letters that I ink on a page.

I’ve shared this analogy a few times with friends. That there are artists. And there are designers. The latter fulfills a need their audience has. The latter creates where the audience is someone other than themselves (while that doesn’t have to be mutually exclusive to building for oneself). For the former, the audience is themselves. It is a form of expression unforgiving to the remarks and views of others. While others may appreciate it, you create for yourself. In a way, the best entrepreneurs start as an artist but end up as a designer. For me, this humble piece of virtual real estate is my art gallery. And a small part of me fears becoming a designer through this blog. I save the design work for other parts of my life.

I’ve been fortunate to have sponsors reach out to support this virtual acreage in the wider, increasingly saturated market of content. As you might have noticed, I’ve turned down everyone so far. Partly because of alignment, but mostly, I’m not yet sure if I want to turn writing into a job. To me, writing is comforting. It’s a sanctuary where I can isolate, even briefly, from the equivalent of noisy San Franciscan streets filled with sirens and honks every minute. And upon receiving payment, I would find myself in debt to someone or some entity. That’s fine if it was an essay or a piece of content I wanted to write anyway. But so far, it hasn’t been. And if it’s not, I find myself enjoying this therapeutic process just a little less.

I’m reminded by something Gurwinder wrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:

“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”

I know many of you came to this blog via the content I write about startups and venture. At least that’s what WordPress tells me. If you came here expecting only that kind of content, I will have to disappoint. And I’m happy to send you recommendations of what I read in that arena. If you came here for that and a little more, I’m excited to share more of my takeaways as I traverse this blue planet. Who knows? Maybe one day beyond.

Nevertheless, I appreciate every one of you for giving me time in your day. Stay tuned!

Photo by Cathy Mü 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!

Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

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v24.0

Photo by Ian Schneider on Unsplash

My parents have always conditioned me to plan each of my ages out. When I was younger, every year I ranked up they would ask me what I want to get done. At the same time, I never felt a strong commitment to New Year’s resolutions. Maybe it was ’cause of the gingerbread cookies. Or the Christmas presents. Or the fireworks and the ball drop. But that lull between the holidays wasn’t conducive to me setting meaningful goals. The “promises” I made carried no weight behind them.

Three years back, after reading Brad Feld’s birthday resolution, I decided to start setting my own birthday resolutions. Outside of a mere date shift, there were 3 reasons I chose to do so:

  1. I had time to recover from the holidays – to get my head straight.
  2. I was motivated watching my friends, family, and coworkers tackle their New Year’s resolutions in the month prior. (Admittedly, more often than not, they lose their initial trajectory, but I only saw the beginning of many of their inverse parabolas.) Motivation is one side of the coin; FOMO is another.
  3. In that motivating January, assuming I haven’t yet completed my previous year’s resolution(s), it motivates me to finish strong – the “last mile” sprint.

That said, this is my first year posting my resolutions publicly. Why? One, it’s to keep me accountable. Two, as Jeff Wald once said, “practice true vulnerability by opening up about the potholes ahead, not just the ones in the rearview mirror.” And one of my resolutions from v23.0 was to become more comfortable being vulnerable. So, what will the new update look like?

Here are the patch notes:

Build ideas from 0 to 1.

This year, I plan to actively help 2 startups go from idea to product-market fit. After 3 years on the venture side of the cap table, the one thing I’ve noticed more and more is that I miss getting my hands dirty, especially in the early stages. I miss the ups and downs. I miss the freaky moments (and the big wins). It may sound a bit weird. But I may have emotionally removed myself from being entrepreneurial and trapped myself in a bird’s-eye perspective only. And I hate it.

More artistically creative outputs.

Two years ago, I started idea-journaling by inspiration from my former college professor. After going through 9.5 idea journals, I realized I’ve spent less than 10% of my ideation space on artistic pursuits. 40% on VC and startups. 40% on personal projects and experiments. 10% everything else. There’s clearly a lack of diversity in my creative space. So, this year, I’m committing to producing one new art piece every week – be it a new drawing, music composition, culinary permutation, or something that’ll surprise myself. My deepest gratitude to my friends who gave me new canvases to explore my creative white space. You can track my progress on my Instagram.

Balancing Social Media.

In the year when many of my peers are unplugging, I’m going to be more active on social media, fine print included. I’m going to explore more by contributing content on this blog, my Instagram (for artistic pursuits), LinkedIn, Medium, Quora, Reddit, and Discord.

I’ve always shied away from social media – not because of some grandiose sense of self-discipline, but rather since I’ve never been able to fully conquer my shell of introversion. After all, my Facebook profile picture and lack of presence is my form of psychological armor.

That said, I still won’t be scrolling through my news feed on social media. But I will aim to respond to every comment and DM that comes my way. I’m a firm believer in responding to the commitment and time people take to write a thoughtful message. Luckily, I’m also at a stage in my life and career when I don’t have more messages/emails than I can manage.

Reconnecting.

Over the past half decade, I’ve grown a lot from reaching out to, learning from, and helping new folks in my network. And, I’m grateful for each and every experience. I wouldn’t be here today if it weren’t for them. But as a result of constant pursuits of new experiences and expanding my network, I haven’t been able to reconnect with friends, mentors, teachers, and acquaintances I’ve had in the past, outside of my annual holiday greetings and thanks. In this new update, I’m committing 10 minutes every day to meaningfully rekindle old flames that I haven’t caught up with in the past 6 months.

Read more.

By virtue of reconnecting with friends from my past, it’s useful to have content and inspiration when reconnecting, but also as a means to widen my own knowledge horizon. Outside of work and my one-book-a-month of reading, I’ll be indulging in a minimum of an hour of diverse reading every day via the ‘Discover’ tab on Pocket.

Sleep and wake earlier.

Ever since college, I’ve been a night owl. It’s weird ’cause in college, students apparently have this ego contest of how many ‘all-nighters’ one can pull and still be ‘alive’. Being young and naive, I joined in the chorus, but I never won. In fact, in my entire college career, I pulled only 2 all-nighters, not even back-to-back, and I was already dead. But it ended up ruining my sleep schedule. I would go to sleep between 12 and 3AM. Sometimes for no reason at all.

After I came back from my holiday Europe trip, mostly due to jet lag, I started sleeping at 9PM every night for the first week. I felt so much more refreshed in the morning and through most of the day than when I didn’t. But also, there’s so much less noise in the morning between 4:30 and 6:30AM – both on social media and in the neighborhood. And I could much of my creative work done. This year, I’m going to sleep at 10PM latest and wake at 4:30AM.

Goal-oriented exercise.

I haven’t necessarily been unfit, but my daily routines seem to drone by without any personal achievement or goal in mind. I have no plans to reach my past physical prowess where I spent 30-40 hours a week spent on exercise. But this year, I’ll stick to 2 goals for health and exercise: sub-5:30 mile and 20 pull-ups. (I’m at a 7:15 and 7 pull-ups at the time of writing this post.)

–

It’s going to be an exciting year, and I plan to have plenty of hotfixes before I reach v25.0, hopefully daily. Thank you to my friends for all the birthday wishes, support, and feedback.

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An Innovator’s Inspiration

Photo by Skye Studios on Unsplash

Creativity.

I have a love-hate relationship with that word. On one hand, I love and seek to learn from creative souls. It’s a trait that I seriously respect in individuals, regardless of industry, profession, or background. On the other hand, it’s rather amorphous. What’s creative to me may not be creative to you. We are bounded by the parameters of our experiences and what we, as individuals, are exposed to.

So, where do innovators draw inspiration?

Over the years, I’ve seen inspiration stem from three main frameworks:

  • The flow from art;
  • Margins;
  • And, what people dislike.

The Flow from Art

I seem to find that the data largely (with a few outliers) points towards the following:

Art precedes science. Science precedes tech. Tech precedes business. Business precedes law.

Art is bounded only by one’s imagination. Science, which draws inspiration from art, is limited by our physical universe and the fundamental laws. And, tech rides on the coattails of science, restricted by the patterns recognized in our universe by scientists before them. Similarly, business can only optimize existing technology. Following suit, regulations and legal practice can only debate and prevent ramifications that have turned from hypothesis to reality.

On one end of the spectrum, fiction has driven innovation on the fundamental, scientific front. Scientists have tried to make the impossible – fiction, superstition, assumptions, and imagination – possible. On the other end, the legal and regulatory space has empirically lagged behind business innovation. From autonomous driving to the shared economy to video games, a regulatory emphasis came only after incidents occurred. I’m a huge proponent of founders becoming self-regulatory. But that is a discussion for another day.

Margins

As Jeff Bezos famously said:

“Your margin is my opportunity.”

In the lens of a businessperson, profits exist on the margins. In a fully saturated market, as we learned in economics class, perfect competition will squeeze out profits. That margin can be delta between human perfection and imperfection. It can be the difference between a naive and sophisticated individual. It can also be the blind spots between a self-awareness and ignorance.

The good news (and bad news?) is that humans aren’t rational. As much as we try to be, we’re not. We repeat the same mistakes. After all, that’s where our favorite stories come from – the fact that we’re imperfect. If we were rational, our friendly neighborhood kid from Queens wouldn’t have to struggle with identity. Or, Skinner, the head chef at Auguste Gusteau’s restaurant, wouldn’t be out to exterminate my favorite rat chef.

From a nonfictional front, if we were rational, gambling, the lottery, therapy, and more wouldn’t exist. In fact, there’s a whole industry that capitalizes on human imperfection – insurance. We choose to reach for that last cookie when we know a healthier diet with less sugar is better for us (I’m guilty as well). We set New Year’s resolutions to work out more, but regress to our couch norm after the first month. Walter Mischel famously conducted The Marshmallow Experiment. When given the option to wait 15 minutes to double their treats, many children opted for immediate gratification.

There would be way fewer founders if they were rational. I mean, come on, the numbers work against them. 90% of startups fail. So, from a VC’s perspective, we have to ask ourselves:

What’s is the underlying notion that makes this product work?

What is that innate theme in human or societal development that won’t disappear anytime soon? What factors produce such a trend? And what margin is it taking advantage of? Uber was made possible with the evolution of smartphone and faster data. As more data were archived online, Google became a reality because of the internet and browser. Two current examples of underlying notions include:

  • Audio, including, but not limited to, podcasts and audiobooks, is the new form of content consumption. Not only does it free up consumers’ hands and eyes up, audio content is often easier to digest. The spoken word has been around millennia, whereas print is fairly new invention. Emotions and sarcasm is often easier to relay via audio than via print. So, what else is possible?
  • With growing consumer sentiment against traditional social media, like Facebook, Twitter, and Instagram, there is a shift to social experiences surrounding active participation. Sarah Tavel writes a great piece on this. Examples include Discord, Medium, TikTok, and user-generated content (UGC) in video games, like mods and in-game skins. Many of the traditional social media platforms leave users with a more negative passive experience, where they feel a sense of FOMO (fear of missing out). Through active participation, users can be a part of the conversation, rather than watch from the sidelines.

What do you dislike?

Speaking of negative experiences, aversion is a strong motivating emotion humans have. Like prospect theory illustrates, loss invokes a stronger response than gains. It also happens to be one of the reasons why I probe how obsessed a founder is about a certain problem.

In a recent interview with Andrew “Kappy” Kaplan, host of the podcast, Beyond the Plate, Grant Achatz, legendary chef, talks briefly about how he drew inspiration from his daughter’s dislike of cheese, yet she still ate pizza and grilled cheese sandwiches. Similarly, when his guests at Alinea didn’t like sea urchin, he thought about the ‘why’ and if he could circumvent their aversion by playing with various variables, including iodine concentration.

So, what do you dislike (with a passion)? What about the people around you? And can you figure out a way to change or eliminate that frustration? Take some time through the idea maze.

In closing

Ideas come in all shapes and sizes. Some may be more obvious than others. Some may snowball into a best-selling one. Although I’ve shared the three most common frameworks that I’ve personally generated and seen others find inspiration, it is, of course, not the only ways to exercise your creative muscle. In fact, the first step into being more “creative” is being cognizant about everything around you.

Two years ago, one of my former professors recommended I start ‘idea-journaling’ every day. Since I’ve started, I began noticing more and more stimuli from my surroundings, conversations and frustrations.

It may be a start, but it’s by no means an end. Stay curious.

Photo Credit: Ariel Zhang @yuzhu.zhang
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A Little Perspective on Intuition

I was chatting with an artistic buddy of mine about the parallels between craftsmanship and early-stage investing, and the more we dove into it, the more fascinating it became. Very similarly, Ash Fontana of Zetta Venture Partners provides a fresh perspective in an episode, specifically, at the 28:45 mark, on The Twenty Minute VC. But one thing, in our conversation, stood out to me in particular – where, somehow, I never put two and two together – intuition.

As you might’ve noticed on this blog already, I’m obsessed with intuition. I’ve asked many an investor to try to break down their intuition, or unconscious competence, hoping to learn from them in tandem with entrepreneurs I have met over these days. I’ve also asked experts from various fields – music, cinematography, culinary, sports, politics, and more – about their various forms of muscle memory. And my conversation with my buddy reminded me of a short journal entry I wrote over a decade ago, about the first person who described intuition to me:

It was late that summer night. The sun had already set, and the crickets had come out center stage in tonight’s feature performance. The slow chorus of whirring was accompanied by the occasional electrical spasms of the 20th century street lamps right outside the studio.

I was helping my teacher pack up the last of his art supplies and move it to the rusty, old shed in his backyard. As I put all the brushes and paints in their respective shelves, I couldn’t help, but notice an array of canvases lying in the left corner. As my curiosity ended up getting the better of me, it turned out to be a series of beautiful and complex surreal, abstract, and Chinese watercolors – quite the contrast to his usual realistic style.

“What do you think?”

“It’s beautiful,” I replied, as if on autopilot.

He paused for a second.

“David, do you know what the toughest thing to draw is?”

“Maybe this,” gesturing at the canvases I was flipping through like a Rolodex. “Oh! And monsters.”

“I don’t think so,” shaking his head, “it’s humans.”

I couldn’t help but pop my favorite question, as a 9-year old, “Why?”

” ‘Cause we see them every day – on the streets and at home, angry and calm, wrinkled and not, and from the day we’re born till the day we die. So, the smallest of deviations from what we’re familiar with is recognizable, not just to an artist, but any person. The average person may not always know why and how it doesn’t look like the people they’re used to seeing, but they will always be able to tell the difference, before you have a chance to blink.”

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