Tag: writing

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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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#unfiltered #67 How To Make Writing Easy For Those Struggling

writing

A founder looking to write more long-form recently asked me, “What does your writing process look like?” As I was sharing my long answer to her short question, I realized, “Holy f**k, my writing process sure has evolved over the past few years.” In an effort to encase my current thoughts in amber, I find myself transcribing thoughts from gray matter to illegible scribblings. And from a 180-grams-per-meter-squared canvas to a two-dimensional electronic screen once again.

A trip down memory lane

I remember when my friend first asked me, “How are you able to commit to a weekly writing schedule? Aren’t you busy enough?” And I shared a secret with him. Something that one of my mentors shared with me.

Before officially starting my blog, I wrote 10 essays – a Plan B in case I ever went through a dry spell. Knowing I had the comfort of a cheat week and still having content to put out gave me the courage to continue writing every week. Almost three years later, of those 10 initial pieces, I’ve only two of the afore-mentioned. In the world of content creation, there’s a massive graveyard of creators who never make it past 10 pieces of content – be it blogposts, podcast episodes, YouTube videos, and so on. I would know. I started 3 blogs before this one. For each of the three prior to this one, I have an epitaph that made it to five or less posts.

The evolution of process

In my first year, I usually spent time conceiving a blogpost at night when I found myself to be the most creative, and editing the same one in the morning before the rooster cried to the awakening sun, when I found myself free of distraction and in peak efficiency. Yet despite a greatly industrialized process, one consistent theme throughout 2019 and 2020 was regret from publishing an essay too soon. There were multiple cases where I’d stumble on new, yet relevant information often within hours of publishing. In fact, this gnawing yarn of remorse reached such a level of prowess that I was re-editing blogposts by the paragraph on a monthly basis. Sorry to all of my early subscribers. Good news is you have your very own limited edition copies of David-jumped-the gun-again.

And so I started delaying my publishing schedules – to account for this sense of continual regret. In my current phase, I break down writing into three phases:

  1. Time to create
  2. Time to ruminate
  3. Time to edit

Time to create

One of my friends once told me the secret to creativity is to “give your brain time to be bored.” DJ, one of the most creative people I know, having worked to create some of the most iconic animations we know today during his time at Cartoon Network and Lucasfilm, and now a YouTuber with over half a million subscribed, once shared with me, “Creativity is a residue of time wasted.”

When I asked him to unpack that statement, 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.”

And he’s right. The more time you spend moving or doing, the less bandwidth your brain has to explore new possibilities. The nuance here is not to block some amount of time every day to ideate. In fact, if you’ll allow me to be brutally honest, while it is giving yourself time to be bored, it’s too structured. And by definition, creativity, like DJ mentioned, is unstructured thinking. Subsequently, blocked time often creates unnecessary stress and anxiety to create. Especially when your mind is drawing blanks and you’re on a clock.

Instead, allocate time immediately after your brain has been given 10 or more minutes to be bored. For example, after you take a shower. Or go on a 30-minute run. Or a 20-minute power nap. Simply, even going on a 20+ minute walk helps your brain re-center and refresh. And always, always write down your ideas. No matter how awesome or lame you think it is. The more you practice the art of ideating, the more consistently better your ideas will be. Not saying that I’m the most creative person out there, but I still have “trash” ideas every so often, but at a far less frequency than when I started.

Time to ruminate

If you’ve ever bought a new car – for the sake of this essay, a black Toyota Camry – as soon as you buy it, you start noticing more black Toyota Camry’s on the street. In fact, you’ll start being able to identify the 2022 versions versus the 2021 or the 2016 ones. A combination of recency bias and confirmation bias. The same holds if you go to a new restaurant, you’ll start noticing that it pops up more in conversations with friends or as you’re scrolling through Instagram.

On the same side of the token, once you seed an idea in your brain (or better, on paper), you start realizing, there is more content and discourse in the world about said idea than you once thought. In the time I spend between creating and editing, I stumble upon or (re)discover articles, podcasts, conversations, experts in my network, just to name a few, when I give my brain time to ruminate.

I like to visualize the scene from Ratatouille when Remy is savoring the individual and collective flavors of the strawberry and cheese, unlike his brother Emile who gorges food down without a second thought. Whereas Emile loses the magic of culinary world, Remy sees what no rat has been able to enjoy prior. Simply put, be Remy! Savor your thoughts.

Time to edit

For me, editing has become the easiest, yet hardest part of writing. All I have to do is string together words and thoughts. I have all the biggest pieces on paper already, but formatting, grammar, punctuation, you name it, feels just like busy work, especially where there are so many more productive things I could be doing.

So, time to edit is akin to time to be inspired. As such, there are two takeaways I’ve learned about myself over the past three years:

  1. I edit in the early morning or late at night. No one will ping me (usually). There is no urgency to respond. Simply, no distractions.
  2. I have a Google doc (which I might share one day, but as of now, it’s a hot mess) that includes all the pieces of content that has, in the past, inspired me to feel a distinct emotion. I use this library of emotions when the content I am creating (blogpost, email, pitch deck feedback, replying to a friend who’s in a rut) requires empathy. For example…
    1. If I want to feel sad, Thai life insurance commercials are my go-to 5-minute sadness augmenters. Here’s one of my favorites.
    2. For insecurity, I like to revisit Neil Gaiman’s short blogpost on imposter syndrome.
    3. For pure inspiration and drive, Remember the Name or any of Eminem’s songs.

In closing

While I don’t timebox myself in this 3-step process, on average, writing a blogpost takes me about two to three weeks. In case your curious, any blogpost where I lead with a sentence that includes “recently” instead of a set time probably took a few weeks to come to fruition.

In effect, writing never feels like a chore. Rather, it’s inspired. Inspiring. Uplifting. And de-stressing.

Photo by John Jennings 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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#unfiltered #63 How To Be Selfish To Be Selfless

Back in my sophomore year of college, I was running to be the vice president of a business organization. Part of the requirement to run as one was to shadow at least two executives from previous generations who held the same role. Brownie points if you shadowed the broader executive team as well. The goal was to better prepare yourself by increasing the context you had about a new role.

I checked off those boxes with flying colors. In fact I ended up talking to more than 20 other executives and other key campus constituents we would be interfacing with. Along the way, I shared what I would do, not do, and do differently compared to previous roles. I also told them how I would forever change the organization and its impact on campus and students. Frankly, I felt like I was a on a roll. I was on top of the world.

Yet one winter night (it’s always the winter nights that get you), when I was on my haughty high horse, one person stopped me in my tracks. With one simple question. “What is your selfish motivation?”

“I’m going to change…”

“No, David… what is your selfish motivation?“

Flash-forward

Last week, one of my favorite hustlers reached out to me. She was planning to start a newsletter soon and wanted some advice from a fellow writer. After a few exchanges asynchronously, it became apparent that her biggest obstacle was keeping to a schedule. If you’re a frequenter here, you’ll have noticed I’ve already lost all semblance of a schedule other than publishing weekly. Some weeks I publish on Mondays. Others on Tuesdays. Some weeks see two essays. Others only one. But I have yet to lose my streak of publishing weekly. But I digress.

There’s a large graveyard filled with content creators who post ten or less times. Off the cuff, I dare say 90%. Prior to this blog, two of my other blogs were also no stranger to the obituary.

So, I posed the same question that stumped me all those years back. What is your selfish motivation?

What is your selfish motivation?

Most people, especially in the realm of entrepreneurship, job interviews, politics, and PR stunts, share their selfless motivations. Everyone’s a Samaritan. While there is some truth to it, everyone needs a really good selfish motivation.

On your best days, if your project is doing really well and you’re absolutely crushing it, your selfless motivation will be what you tell the latest press release, your cousins over the holidays – the story you pitch to others. The story you also tell yourself to give your job meaning. But on your worst days, when you want to give up, your selfish motivation is what’ll keep you going. When you’re at your worst, you won’t want to care for others. You care about yourself. What’ll keep you sane? If your selfish North Star isn’t strong enough, it’s easy to give up.

You need both. Your selfless motivation will help you reach for the stars. Your selfish motivation will prevent you from hitting rock bottom.

For example, for this blog, my selfless motivations are:

  1. Democratizing access to resources and education to help people move the world’s economy forward,
  2. Empowering founders to not fall through the same potholes I or other founders fell through – to make new mistakes not old, and
  3. Empowering and inspiring others to live more enriching lives.

It’s what I tell others. My lofty goal that’ll make writing this blog meaningful to me.

On the other hand, my selfish motivations are:

  1. I write to think. My thoughts are so much clearer on paper than if I just speak them. If I don’t write things down, I’m a mess.
  2. I forget things easily. Short term memory loss. And my blog is a way for me to catalogue my own learnings.
  3. I feel much more comfortable being vulnerable with strangers than with friends. So my blog helps me relieve much of my stress and anxiety.
  4. I am neither as good as people say I am nor as bad as people say I am. This blog keeps me honest.

In closing

That same winter night was the day of the winter equinox. I don’t mean to dramatize my little anecdote, but I nevertheless I do find it provides a little flavor to the story.

“No, David… what is your selfish motivation?”

“I don’t follow.”

“I ask every officer candidate this question. There will be days that you will hate the job more than you will love it. And I need to know if you have it in you to weather those days.”

I don’t remember what I told him that night. I don’t think it was a particularly honest answer. Or maybe I was honest. But it wasn’t enough. I didn’t get his vote of confidence, but I did enough legwork to get the approval of others.

In the end, I got the position. And he was right. Times got tough. There were days I hated the job. And on those days, in particular, I didn’t do anything remotely close to “changing the organization and its impact on campus.”

In his words, I wasn’t selfish enough.

Photo by Ian Chen 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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2021 Year in Review

Kintsugi.

The Japanese art of finding beauty in imperfection. More specifically, the art of mending broken pottery. Kintsugi finds an object’s value and beauty is a result of its imperfections, rather than the lack thereof.

Much like the year prior, and like for most, 2021 was a year of imperfections. What could have gone wrong went wrong. And what could have been weighed heavily on many people’s minds. It’s been a trying year for almost everyone. From Delta to Omicron, from the insurrection in January to military withdrawal from Afghanistan, from forest fires to the increase in crime in the Bay Area. Despite still wrestling with the constraints imposed by the pandemic and the broader socio-political-economic world, 2021 was the worst and best year I could have ever hoped for. The beauty was not that these events happened, but that these events led us to form deeper relationships, greater awareness for macro issues, and a general movement forward to change what hasn’t and will not work in tomorrow’s world. Simply put, I’ve never been more bullish on being human.

This year was the year of saying “Yes.” In contrast to my track record of regressing to “No.” And so far, I’m on a roll. That also means that I’m busier than ever. Nevertheless, because of my intentionality behind finding serendipitous moments in my life, I’ve had the pleasure of finding myself in a constant state of inspiration. To quote one of my good friends, who’ll appear in a blogpost soon enough: “Inspiration is the disciplined pursuit of unrelated [and unexpected] inputs.”

I wrote almost 90,000 words this year, excluding this blogpost, which for better or for worse, means I wrote just enough to fill the average nonfiction book and a half. In terms of the number of blogposts and words I’ve written, I’ve slipped in comparison to last year. Last year, I minted over 100 essays. And this year, I’m 20% shyer in quantity on both fronts. Yet, while recency bias may play a role, I’ve never been prouder of the content I’ve put out. Fundamentally, what I learned is that I have to take longer per blogpost.

My writing journey pre-2021

In 2019 and 2020, I took pride in minting a blogpost in under 24 hours at best. 48 hours at worst. I would start writing each piece during the night, right after my shower. Go to sleep. And finish editing the next morning before publishing.

Under those circumstances, while there were a number of pieces that I am still proud to have written to this date, there were many that would have been orders of magnitude better if I just let it sit for a few days longer. If I just let the content marinate a bit longer.

… In 2021

This year, unintentionally, I did just that. It started with a steep ramp up in my day-to-day schedule, rendering me unable to commit large chunks of time to sit down, write and edit. On average, each piece took 5-7 days before it went from conception to presentation. Of course, a small handful took 2-4 weeks. Equally so, there were a few on the other end of the spectrum that took less than 24 hours. But the more time I gave myself to think about each piece, the more robust each piece became. So, my process evolved as a function of my schedule.

Today, at least twice a week, I still allocate two hours to sit down, write and edit. I still find my creativity at its height right before I hit the haystack. And I still make the bulk of my edits in the morning. But I also give myself time to be bored. Time to just think with no intended purpose or goal, when I take long drives or in the shower or during a morning exercise routine. And as long as there seems to be a strong correlation between time to be bored and my creative output, I’ll continue this process in the foreseeable future.

2021’s Most Popular

Essays published in 2021, ranked by most views:

  1. How to Pitch VCs Without Ever Having to Send the Pitch Deck – One of the most insightful lessons I learned this year from an incredible serial founder. And especially useful for founders who don’t have a pre-existing investor network.
  2. Rolling Funds and the Emerging Fund Manager – A deeper dive to AngelList’s Rolling Funds and what that means for the emerging manager. Since then, I have learned some new insights on that front, which I’ll include in a future blogpost. That said, as an addendum to this blogpost, while much easier to raise capital from accredited investors, do beware of vintage quarters, especially for LPs. If you miss out on a quarter where the GP makes an incredible investment, you miss out on the carry there.
  3. Should you get an MBA as a founder? – Admittedly, this one’s ranking came as a surprise to me, but in hindsight, I know many founders, and professionals in general, wrestle with the pros and cons of advancement education as a means of career development.
  4. #unfiltered #57 True Vulnerability Is Messy – I’ve hosted a number of social experiments as well as vulnerability circles, but it wasn’t till my conversation with my good friend, Sam, that I realized what true vulnerability meant. Not the kind that’s been romanticized by Silicon Valley and the wider media.
  5. My Top Founder Interview Questions That Fly Under The Radar – Investors rarely share their rolodex of questions with founders. And understandably with good reason. But I’ve never been one to optimize for ‘gotcha’ moments. If you’re building a business that the world needs, the last thing you should be worried about is what kind of curveball questions investors can ask you. In this piece, I share my top 9 questions (outside of the usual few every investor asks) and my rationale behind each.
  6. The Smoke Signals of a Great Startup From the Lens of the Pitch Deck – From the perspective of an investor, I break down the foci points on the pitch deck depending on what stage your startup is fundraising at.
  7. Losing is Winning w/ Jeep Kline, General Partner at Translational Partners and Venture Partner at MrPink VC – One of my more contrarian posts from the insights of Jeep. What makes seemingly no sense at first glance carries a lot more depth than meets the eye.
  8. How to Find Product-Market Fit From Your Pricing Strategy – The broader business world has always found PMF through some cousin of the NPS score and/or usage metrics. While those are still extremely pertinent, I find it illuminating to view PMF through leading indicators like pricing, rather than lagging indicators, like usage.
  9. 14 Reasons For Me Not to Source This Deal – One of my more tongue-in-cheek posts about founder red flags. I imagine a large contributor to its current ranking is due to the fact that my buddy, DC, reposted this on his blog as well.
  10. #unfiltered #56 How Thirteen Technology and Thought Leaders Break Down Self-Doubt – One of my favorite blogposts I wrote this year, written during one of my most emotionally-turmoiled times. These 13 were my North Stars, when I found it hard to see the night sky. Hopefully, they might serve as yours in some capacity as well.

All-Time Most Popular

All the essays I’ve ever written, ranked by most views:

  1. 10 Letters of Thanks to 10 People who Changed my Life – Every year, during the holiday season, I write a plethora of letters of thanks to the people who changed my life in my short years of being alive so far. I wrote this piece back in 2019 sharing what I wrote word-for-word publicly for the first time. I never expected this essay alone to account for a plurality of your views. This is the only one of my now 200 blogposts that draws in readership almost every day since its inception. In 2021 alone, this one blogpost accounts for over a third of this blog’s viewership. The power law is truly incredible.
  2. #unfiltered #30 Inspiration and Frustration – The Honest Answers From Some of the Most Resilient People Going through a World of Uncertainty – Part one of two, where I ask 42 world-class professionals about their greatest motivators. I ask them two questions, but the catch is they’re only allowed to answer one of them.
  3. How to Pitch VCs Without Ever Having to Send the Pitch Deck – I imagine this one will be a repeat offender on this list. Time will tell.
  4. My Cold Email “Template” – I’ve had the fortune of meeting some of the most respectable people in the world and in their respective industries. Many of whom I met through a cold email. In this essay, I share my playbook as to how I did and do so.
  5. The Third Leg of the Race – An oldie, but a goodie. This notion is as true now as it was when I wrote it last year. The third leg of the race is always the hardest, but it’s the one that’ll decide if you win or lose.

My most memorable pieces in 2021

Because of this blog, I’ve had the chance to share my voice and thoughts, yet also pick the brains of some of the most brilliant people in the world. So I hesitate to even rank my favorites ’cause almost every blogpost I write has a special place in my heart. Nevertheless, if I had to pick and if I’m being honest, there are a handful that would go on my personal Mount Rushmore this year. In no particular order…

  • #unfiltered #56 How Thirteen Technology and Thought Leaders Break Down Self-Doubt – Same as above.
  • #unfiltered #57 True Vulnerability Is Messy – Same as above.
  • The Investor Purity Test – People in venture capital often take themselves as well as their work too seriously. And not that they shouldn’t, but everyone deserves a little satire about their job. Ours is no exception. So I created a mini quiz to see how pure you are from the woes of early-stage capitalism. Have fun!
  • #unfiltered #61 How To Host A Fireside Chat 101 – After hosting a series of fireside chats, panels, and podcast episodes (the latter yet to released), I share what I’ve learned in this essay. It includes not only how I think about asking questions during the chat, but also how I prepare for the conversation.
  • The Hype Rorschach Test: How To Interpret Startup Hype When Everything’s Hyped – In a market of noise, I break down how I think about finding the signal above it all.
  • Startup Growth Metrics that will Hocus Pocus an Investor Term Sheet – I always tell founders to lead with the metric that will “wow” an investor in every cold email and/or warm intro. Earlier this year, I broke down just what kinds of metrics and their respective benchmarks that will wow an investor.
  • Creativity is a Luxury – Back in May, I sat down with one of the most creative people I know – DJ Welch. And asked him how he regularly found inspiration. To this day, I still re-read this blogpost to help me out of a writer’s block when I’m in one.
  • #unfiltered #53 A Different Way To Count – Most people count their lives by the years that pass. But, what if our unit of measurement wasn’t years, but the number of presidents we live to see or the number of vacations we get to have with our significant other? You might see life quite differently.
  • #unfiltered #51 The Fickle Jar – I have a lot of ideas. Most of which are either completely silly, ludicrous or require time I am willing to prioritize. I’ve known anecdotally that very few actually make it past the Mendoza line. Nevertheless, thanks to my friend, I now have a visual way of tracking my promiscuity between ideas.

Photo by Riho Kitagawa 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!

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#unfiltered #59 I Am The Worst Marketer Out There

billboard, marketing

Last week, after a lovely conversation with a startup operator, he asked if there was anything he could help me with. I defaulted to my usual. As I’m working on being a better writer, I asked him if time permitted, could he give me some feedback on my writing. For the sake of this blogpost, let’s call him “Alex.”

While I expected just general feedback on my style of content delivery, Alex gave me a full audit of this blog. He told me I should focus, until I’ve built up an audience. He also said that I should find my top 20 blogposts, figure which category they fall under and narrow down by writing more of those. On the same token, he recommended I reference Hubspot’s “topic clusters.” Which is an amazing piece about how to nail SEO in 2021, if I say so myself. Incredibly prescient. And incredibly true.

He also recommended I use Medium or Substack over my antiquated design of a website. And forgo the header image. Which you might have noticed I haven’t (yet).

The thing is… he’s 100% right. I’ve done little right, in the sense of marketing and branding. In fact, in the Google search engines, I probably am a mess to categorize, which means I exist in no category. Even in my own words, focusing on everything means focusing on nothing. While at the time of writing this post, a good majority of my content is based in startups and venture capital. If I focused on better branding, I would have doubled down on fundraising, or marketing. Or social experiments. But I haven’t.

Truth be told, I’ve stunted my growth, or my brand’s growth, by intentionally choosing otherwise. In turn, there are only two questions I optimize for in this blog.

  1. Will this make David from yesterday smarter?
  2. Is this still fun?

I started this blog writing for an audience of one. For the person I was yesterday. And if I know the me from yesterday would love it, then I have at least one happy customer.

I don’t write this blog for profit. This blog is my de-stressor. It is my entertainer, yet also my coach. It is my confidant. And it is just fun. The process of learning and thinking through writing – refining my thoughts – gets me really excited. I don’t want to end up dragging my feet through mud. Funnily enough, despite being an extremely, and I stress the former word, small blogger, I’ve had the occasional brand reach out to sponsor content. As you might have guessed, I said “no” to everyone so far. Either I didn’t believe that the product would make the world a better place or that I just didn’t get their product. This is not to say I won’t ever take on sponsors, but I just want to be really excited about it.

I’ve also had a number of folks reach out wanting to guest post on this blog, to which I’ve also said “no” to everyone so far. Because (a) it makes me lazy and defeats the purpose of me writing to think, and (b) I haven’t learned anything from them yet.

And because I write from a motivation of “psychic gratification,” borrowing the phrasing Tim Ferriss used in his recent episode, my writing is “very me,” to borrow the phrasing of readers and friends who’ve talked to me face-to-face before. I feel I can be genuine. And I can be unapologetically curious. I can learn what I want when I want how I want. I love each topic I write about, at least in the moment my pen touches paper. It excites me. It inspires me. And it pulls me with a force I want more of.

As a product of me being me, every so often, a random essay sees a momentary breath of fame. On average, it happens every 7th or 8th blogpost. I have these random spikes of several hundred views within 24 hours every so often. And don’t get me wrong. I would be lying if I said that wasn’t gratifying as well. Other times, some essays are far more perennial and see anywhere between two and ten views a day – almost every day. There are the ones that never make it onto the stage. And live somewhere in a virtual public graveyard.

I’m publicly logging my thought process here as a bookmark for future reference. And so that my future self can’t go back in time and write off my thought processes now in a grand motion of revisionist’s history.

I also know that this won’t be the last time I revisit this topic. My future mental model might differ greatly from what it is now. As John Maynard Keynes, father of Keynesian economics, once said, “When the facts change, I change my mind.” But it might stay the same. Who knows?

I’ll keep you updated.

Photo by Bram Naus 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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My Thoughts on Audio Recordings Going Forward

You may have noticed that after only two essays including an audio reading, I’ve stopped. Initially, I wanted to pair audio with every essay as an alternative to reading the essay. But over the past few weeks, partly due to an increase in workload, recording my audio became a seemingly arduous task for me. A frictional step. A barrier to entry. Not that it takes long to record, but editing my own speaking quirks and breaths (oh boy, if you only knew how great this mic was at picking up every breath. I sound like I have sinus problems.) in each clip accounted for an additional half-hour usually. And that same frictional step left me with a backlog of recordings that I had to do, even though the content was ready. Which:

  1. Slowed down my production schedule (at the time of writing this blog post, I have five fully written blog posts I’ve been meaning to put out, but held back due to recording procrastination)
  2. Became an excuse to myself of why I couldn’t produce content on the same schedule as I used to

Going forward, I’m not going to give myself that excuse. I will record audio to accompany an essay, on two conditions:

  1. For essays I personally really like and have time to record for
  2. Retroactively, if you, my readers, reach out and want an “audiobook” version of your favorite pieces on this blog. I won’t be able to fulfill every single request, although I’ll do my best to, but I’ll prioritize the ones with more requests.

So, please bear with me. The goal is still for me to read every blogpost. I’m working on being able to do all the above more efficiently. I’m testing out new formats as time allows. A couple things I’ve tried so far:

  • Getting a pop filter to filter out high-pitched consonant sounds
  • Finish writing before I head to bed and waking up earlier and recording at 6am

None has fully resonated just yet. And it really makes me admire the work of audio engineers and voice actors and actresses each passing day.

Stay tuned!

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#unfiltered #52 Is This Citizen Journalism?

For any content creator, like myself, it’s incredibly easy to bifurcate ourselves along two paths.

  1. Everything you create is going to change the world. I am important.
  2. Nothing you create has any impact on the world around you. I carry no value.

Some voices over time have profound power on society. They hold the capacity to elicit widespread mimetic behavior. And many an author have snowballed down this thesis – for better or worse. There’s a saying that goes: You’re never as good as they say you are; you’re also never as bad as they say you are. Or maybe that was just a paraphrase of Lou Holtz‘s line: “You’re never as good as everyone tells you when you win, and you’re never as bad as they say when you lose.”

So, the flip side, the rise of citizen journalism has led more and more people to share transient perspectives of themselves or of the world in the form of social content. With the occasional goal of turning such fleeting outlooks into enduring memorabilia. Be it through Medium or TikTok, Substack or Instagram, YouTube or Clubhouse. A blog like this or a podcast. Yet when zooming out, we see the incremental impact of each additional voice is often drowned in the noise that populates the 21st century internet.

The truth, really, is somewhere in the middle. Where exactly? I don’t know. And frankly, it’s different for each genre and speaker out there.

Yet that doesn’t mean we should stop. At least for me, in knowing that I have positively impacted just one person’s life in a meaningful way is enough of a reason to continue. And if there’s a ripple effect beyond myself, then I am steps closer to having a life worth beyond a single century.

Brian Armstrong of Coinbase recently wrote via a blogpost. “The tools for distribution have become democratized, and every company can become a source of truth.” In a similar way, each individual – a company of one, a solopreneur in her/his own right – can become a source of truth. Each individual is a platform for the story we ourselves want to tell that isn’t misinformed or misaligned with post-production and traditional media incentives. Of course, it’s still up to us to have a head above two shoulders. Every individual can become a source of truth. But that doesn’t mean every individual is a source of truth. It’s up to our own judgment to think critically and act accordingly.

But let’s be honest. What I write isn’t journalism. It’s just a formulation of opinions and anecdotal observations over the course of time. While I try to approach my content from as much of an unbiased and informed perspective as possible, reality is I’m still missing something. In many ways, each of you is learning how I learn as I learn. Or maybe you’re already two steps ahead.

Photo by Brad Neathery 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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Why User Hacks Are Awesome to Get to Product-Market Fit

user hacks, product-market fit

I was introduced to a founder of an e-commerce marketplace recently trying to figure out what product-market fit looks like. Specifically what might be some early tells of PMF. And I told him, “If your users are sticking around long enough to try to game your system, you have something they want. While it might not be in the most efficient format, you’re close to PMF. Subsequently, solving that frictional point that users are trying to ‘hack’ will delight them.”

Last year, I wrote that one of the tells of a great unicorn idea is frustration with the status quo. And the lagging indicators of frustration are complaints, but even better, “hacks”. Life hacks. Career hacks. Cold email hacks. Any time a forum or community comes together to share best practices is a potential market opportunity. As Jeff Bezos once said, “Your margin is my opportunity.”

Similarly, if some of your users converge around circumventing your platform, they’re hacking their way to find a better solution. But the fact they’re sticking around on your platform means you have something they want. And while it could be more elegant, you’ve solved the rocks of the “rocks, sand, and water” framework. What’s left are the “sand” and the “water”. And they come disguised as a user hack.

Sarah Tavel of Benchmark once wrote: “You must create an offering that is so compelling, it stands by itself in the consumer’s mind.” Solving all the frictional points in the user journey will get you to that compelling offering – a lovable product.

A reader reached out to me last year and said, “Thank you… [But] you have no idea how long I spend reading your blogposts with a dictionary next to me.” While it wasn’t necessarily a hack, to know there was a reader out there willing to weather through my idiosyncratic vocabulary in my earlier essays meant a million to me. But at the same time, it was a sign I was too caught up in my own wordsmithing. So, I dialed it back. While there will still be some esoteric jargon from time to time, I try to make my writing more relatable when editing. And to that reader… if you’re still reading this essay, thank you.

Back in 2007, Marc Andreessen wrote: “The market pulls product out of the startup.” In this case, that pull becomes a race between you and your users’ frustration. Can you release an update that addresses your users’ pain point before they become so frustrated they pack up and go? Either to build their own version or try a competitor’s.

I love Max Nussenbaum of On Deck’s analogy here. “If the market is indeed pulling the product out of you, you sometimes feel less like a creator and more like a mere conduit.” You, as the team behind the product, are a conduit to satisfying your users’ needs. As Mike Maples Jr. says, “Getting storytelling right means the founder is the mentor of the story (ie Yoda), rather than the hero (ie Luke.).” Your customers are the heroes of the story. Of their story. And your story. How they spend their time should offer you brilliant product insights.

Photo by Florian Krumm 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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#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!

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