Category: Ideas/Creativity

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2022 Year in Review

rollercoaster, sunset

This year I learned a lot. From the fact that most of my readers love to read my blogposts on Wednesday 2PM Pacific to how I could get general partners — some of the smartest people in VC — to be vulnerable and candid to how to set up an SPV from scratch (without the help of any platform). It’s been a rollercoaster. And I loved every second of it.

My blog grew modestly. No hockey-stick curve. And that’s okay. I enjoyed inking each word. To me, that’s what makes this blog worth it.

I’ve written 87,000 words, with over a third fewer posts than last year. I want to say I was busy. And I was. But another equally true reason was that I was scared to disappoint. I wasn’t content publishing half-baked ideas. And it sucks when I know I wanted to write more. How? Because as of today, I have 53 drafts just sitting in my WordPress folder. With 245 total published essays, that’s a sixth of my thoughts I withheld or postponed because I thought: “They’re not good enough.”

Comfort is powerful. And earlier this year I found myself resigning to habitual cycles I had developed in the year prior. A fear manifested into reality. So I made a promise to myself to escape the clutches of complacency.

But while I hesitated on the writing front, I chose to take risk elsewhere. I took big bets. For one-way door decisions, bets I didn’t wait for a 100% conviction on. And just jumped when I got to 70%. As a function, I had many firsts.

It’s the first economic downturn I’m living and working through (2008 and the dot com era don’t really count as I was still in grade school).

For the first-time I broke my streak of writing weekly since the inception of this blog. While I can blame servers and bugs, the reason was simple. I just wasn’t prepared enough.

I set up my first SPV (special purpose vehicle) from scratch. With a s**tload of help, but yes, from incorporating to legal docs to setting up bank accounts, and so on.

I started interviewing LPs in fireside chats — something I never imagined I would end up love doing or be capable of doing.

I hosted my first social experiment-like event paid for and sponsored by investors for investors, rather than my usual audience of thrill seekers. Based on the feedback, I’d say it was a success. Many learnings and an indispensable village helping behind the scenes. A handful of things that could have been better. But a night of surprises. And I learned — something I hope to share more in the future (as I have larger sample sizes) — events, just like books, movies, shows, podcasts, and so on, are stories. And stories have settings, character developments, plots, a climax, and an end where the audience can imagine no other (to steal a line from Robert McKee).

Additionally, I…

  • Took my first vacation, not touching any work at all, in six years;
  • Went to my first traditional Vietnamese wedding; hell, travelled to Southeast Asia for the first time;
  • Successfully made fruit chips en masse;
  • Realized my favorite photo mode is portrait mode;
  • Built my first PC;
  • Put together my first career manifesto — my professional raison d’être.

And it’s still not enough.

But I digress. While I wrote far fewer posts, 2022 was the year I wanted to make things count. As Muhammad Ali once said, “Don’t count the days; make the days count.” The below, while I wish I had a longer list, are the blogposts that counted.

2022’s Most Popular

The below are the essays that I published during 2022, and generated the most views, ranked from most to 5th most:

  1. The Emerging LP Playbook – I never expected this one to take the top spot this year. Borne out of a personal curiosity and an attempt to better understand the black box industry of LP investing, ever since Andrew Gluck put “emerging” and “LP” back-to-back on a Zoom call, I had to learn more about it. The truth is I only knew a handful of known LPs at the time, but I’m happy this piece has expanded the horizon for not only myself, but everyone else out there who’s read this curious piece. It answers just one nexus question: For a first-time LP, where do you start?
  2. 99 Pieces of Unsolicited, (Possibly) Ungoogleable Startup Advice – I’m a collector. And have been so for a while. Specifically, a collector of quotes. I have journals dedicated to them. When the pandemic hit, I had a thought, what if I collected 99 soundbites (some albeit my own) about being a founder? All tactical. And each will share an actionable lesson. And I shared them. I didn’t know how long it’d take, but I knew that 99 sounded like a good number.
  3. How to Get Investors to Just Ask One Question: “How Can I Invest?” – I had the chance sit down with Siqi Chen, one of the best storytellers I know. And he broke down just what a founder needs to do to secure the bag. The caveat is it usually doesn’t happen after your first fundraising pitch.
  4. What Does Signal Mean For An Early-Stage Investor? – The word ‘signal’ has been thrown around quite a bit in the last two years — 2020 and 2021, if you’re a time traveler and reading this in the future. For instance, an investor would look for ‘signal’ before investing in a deal. In the above blogpost, I break down exactly what ‘signal’ means. And I imagine, in whatever time period governed by FOMO (fear of missing out), ‘signal’ will rhyme.
  5. 99 Pieces of Unsolicited, (Possibly) Ungoogleable Advice For Investors – Just like the one I wrote for founders, soon after, I thought I’d put a list of 99 soundbites for investors. And as I jumped at the opportunity to work with the brilliant team at On Deck Angels, I was living and breathing everything about investors — from angel investing to fund investing. Of course, you can sense my heavy bias towards to latter.

All-Time Most Popular

The funny, yet in hindsight, unsurprising, thing, is that the below are perfect examples of the power law, collectively generating 90% of the views ever on my blog. The below ranked in view count popularity:

  1. The Emerging LP Playbook – I wrote this piece for myself and other investors looking to be LPs. Unsuspectingly so (at least in foresight), this piece generated a huge amount of excitement not only with my initial intended audience — who, I thought, was a niche audience — but also among many VCs and angels out there. I rarely write in hopes to change people’s minds. I’m not much of a persuasive writer, but rather I hope my words offer oases for people searching for answers in a desolate desert. But of the feedback I’ve gotten, it has surprisingly changed a number of people’s minds about LPs, as well as about different asset classes to invest in.
  2. 99 Pieces of Unsolicited, (Possibly) Ungoogleable Startup Advice – Same as the above.
  3. 10 Letters of Thanks to 10 People who Changed my Life – To this day, it still baffles me how this is the most perennially popular essay I’ve written. The SEO keywords I’ve optimized for here are all related to Thanksgiving, yet the fact that search engines bring me new readers every single week without fail is an enigma I’m still unravelling. That said, I am thankful to everyone who’s given me and the 10 people I am deeply thankful for that year the attention and time out of your busy schedule.
  4. How to Pitch VCs Without Ever Having to Send the Pitch Deck – Teach them something new. Many founders who’ve worked with me can attest that that’s been my favorite line to lead with when they ask for fundraising advice. This blogpost and the person behind it (who’ll stay anonymous for now) is the reason for that.
  5. #unfiltered #30 Inspiration and Frustration – The Honest Answers From Some of the Most Resilient People Going through a World of Uncertainty – (Part two of which you can find here.) Interestingly enough, I knew this one would stand the test of time. Something we learn in Econ 101 is that business cycles come in booms and busts. And they oscillate between great times and bad times. The human emotion, our daily lives, and our careers are no exception. Collectively, I queried 42 world-class professionals about their greatest motivators. What keeps them going? I ask them two questions, but the catch is they’re only allowed to answer one of them. These pieces are a gentle reminder that bad times, like good times, never last.

Most Memorable Pieces in 2022

In writing each of the below, I felt the needle move forward. Not for the world or for the people immediately around me. But for me. That I myself took one small essay forward, but a disproportionately giant leap in the way I thought about the world around me. Each is the culmination of not just a few hours of writing, but of many things more. Provocative conversations. Research deep dives. And generous people.

In no particular order, if I were to hide pieces of my 2022 soul and mind in Horcruxes, they would be in the below:

  • The Emerging LP Playbook – You’ll realize that this blogpost appears in all three lists. The first two are outside of my control. But the reason it appears here is this piece catalyzed a spark that’ll come more into fruition in 2023. A spark that emerged from realizing the massive information asymmetry between LPs and GPs. Hell, even between LPs.
  • How to Develop Intuition as a Rookie Startup Investor – This dates as far back as 2017, when I first inked the thought in my notebook. The thesis was simple. Intuition — one’s sixth sense was a subconscious function of the mastery of the other five senses. But then, I felt ill-equipped to explicitly describe what other investors were feeling, and over time, what I was feeling as a function of what I was thinking. In it, I share each of the questions I consider and their respective answers that inform each of my senses (sight, hearing, taste, etc.).
  • How do You Know if You Should Professionalize as an Investor? – I love asking questions. To the point, and I don’t mean this in a tongue-in-cheek way, that often the best way to answer a question is with another question. I’ve gotten the above question many a time this past year, and this piece is a permutation of what helps me get to first-principles thinking when it comes to: Should you raise a fund… or stay an angel?
  • Five Tactical Lessons After Hosting 100+ Fireside Chats – I love hosting interviews. I really do. Part of it is due to the fact I love asking questions. The other half is… well… the average coffee chat is 30 minutes long. Half of it disappears after exchanging pleasantries. So, the big question is: How do you get more time with people you respect? One answer among many is by giving them a stage. That said, as I was doing my homework to be a better MC, the information out there is either paltry or too generic. So I made a promise to myself that as I do more myself I’ll share all the non-obvious lessons I learn. So that others can do better than me. And I hopefully, get to learn from them as they get better.
  • When Should You Sell Your Shares As An Investor? – Selling is really an art more than science. Like investing, often obvious in hindsight, but painfully scary in foresight. And to be a great investor, you have to distribute your earnings. And in order to earn, you have to turn something illiquid into something liquid. This piece was one of my first explorations behind what makes selling hard and how some of the best do it.
  • Quirks That Just Make Sense – Maybe there’s a bit of recency bias here, but this is something a few of my friends have known about me for a while. I just never had a good excuse to talk about it publicly. (Weird that I thought I ever needed an excuse to). But my good buddy Matt brought me out of my shell a few weeks back. And together we put together a piece about the quirks we carry and the origin story of each. Coincidentally enough, just watched Garry Tan’s video yesterday about a similar topic.

In closing

Cheers to a year of life lessons, friendships, skills and experiences acquired that were well worth the ride! And many more to come! If there’s ever any topic you would like me to write about in the future, don’t hesitate to let me know. I have two nominations already.

To peruse one of Kurt Vonnegut‘s lessons, I hope to continue to use your time in a way that you feel is not wasted.

Thank you. And stay tuned.

Photo by iStrfry , Marcus 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!

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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Quirks That Just Make Sense

different, quirky, weird

“Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules, and they have no respect for the status quo… You can quote them, disagree with them, glorify or vilify them, but the only thing you can’t do is ignore them because they change things… They push the human race forward, and while some may see them as the crazy ones, we see genius, because the people who are crazy enough to think that they can change the world, are the ones who do.”
— Steve Jobs

We live in a world where everyone is seeking validation from some kind of audience — large or small. And I’ve come to realize over the years that as long as we’re chasing what most people want, we will eventually be like most people. And truth be told, forgettable. Speaking for myself, I will just be a number in a sea of sameness, rather than THE number.

I realized later than I would have liked that I didn’t want to be like everyone else, after being inspired by a rejection email from someone I deeply respect when she replied with four words “Be interested and interesting.” And I count myself lucky to be surrounded by people who think different, to borrow a phrase Steve Jobs loves. For some, that means going where no human has gone before. For others, it’s a means to live their most fulfilling life.

So, I can only thank my good buddy Matt — one of the most outlier and honest-to-goodness thinkers I know — for the alchemical jazz that birthed this blogpost. Our only ask is that you suspend judgment until you reach the end. What may seem eccentric at first glance may prove to be the kernel of inspiration you didn’t know you needed today.

Below is only a snippet of quirks — seven to be exact — that make the two of us us, but hoping this inspires a larger conversation of people being unapologetically themselves.

  1. The whiteboard in the shower: Leaving no shower thought unturned
  2. Dream journaling: Better access to conscious and subconscious memory
  3. High-quality notebooks: Evergreen homes to high-quality ideas
  4. The Emotional Catalog: The vending machine of emotions
  5. The Excite-o-Meter: Matt’s personal Stoke Diary
  6. Marriage counseling: A recipe for strong co-founder relationships
  7. Restaurant recipes: It never hurts to ask

1. The whiteboard in the shower: Leaving no shower thought unturned

There are only two kinds of reactions I get when I tell people this. Utter bewilderment. And, what I call, sparkle-eyes.

Many of my best ideas happen in the shower. In fact, about 60-70% of the topics I write about on this blogpost found its origin in the shower. But, forget myself for a second. There’s a whole movement in the world called shower thoughts. There’s also some great academic literature on the subject — that hot showers open your pores, helps your blood circulate, and put you in dopamine-high, yet relaxed states, just to name a few. But whether the science matters or not here, one of my biggest frustrations in life is losing access to great ideas just because I couldn’t commit it to memory or document them. Many of mine merely happen to start in the shower.

So, with a small purchase of a $10 whiteboard and $15-20 rainproof markers, you’ll be set.

2. Dream journaling: Better access to conscious and subconscious memory

I’ve been fascinated by dreams ever since I was a kid. Luckily, blessed by vivid imagination, I was able to synthesize the art, movies, and stories I was consuming into interactive experiences in the amphitheater of my mind. To me, dreams were the ever-evolving playground that very few tangible experiences could rival. I’m gonna be hated for saying this, but I remember the day I was let down by the Disneyland promise. I was only seven. And I told myself that day, I would start trying to remember my dreams.

You see, as fantastically awesome as dreams are, the only downside is I forget the vast majority of them within seconds of waking up.

So, for a long, long time, I’ve been dream journaling. I have a notebook by my bedside. And every time, I remember a dream, I write it down and/or draw it out. Even if all I remember is a single word or a single image. Over time, I get better at it. The better I get at capturing my dreams, the more intentional I get.

There’s now a whole slew of literature on the topic, but for me, it’s fun. And an interesting byproduct of it all is I seem to have better memory than most of my peers.

3. High-quality notebooks: Evergreen homes to high-quality ideas

This is truly a prime example that while we all come from different backgrounds, curious minds can reach the same conclusion from different angles. That’s exactly what happened when Matt and I were ideating for this blogpost when we realized we both graduated from ten-cent back-to-school-sale spiral-bound notebooks.

The more expensive the notebook, the more respect you treat it with, and the higher quality of thoughts you will entrust it to house. Think of it like sunk cost fallacy. After all, it’d be a pity to leave the sacred halls between the two leather covers unadorned with ideas that would complement the quality of the frame.

To Matt and I, our weapon of choice is Leuchtturm1917. For myself, undeniably, paper that boasts the density of 150 g/m2.

4. The Emotional Catalog: The vending machine of emotions

The human emotional spectrum is fascinating, yet quite volatile and unreliable when you most need it. For instance, I know I’m not alone in this, but I used to always find myself feeling anger and aggression upon hearing constructive feedback, rather than curiosity. That I felt anxiety and overwhelmed when on stage rather than excitement and confidence. That I felt frustrated and discouraged when writing blogposts when I want to feel inspired.

So when I committed to this blog in 2019, I started keeping tabs on when I feel strong emotions, hoping to preserve these emotions in cryogenic slumber and awakening them when I needed them most. I keep a Google Doc that has a glossary of emotions in it — from joy to anger, from optimism to jealousy, from compassion to sadness, just to name a few. And each time I consume a medium that inspires a certain emotion, I include it in that doc. They become my shots of espresso when I’m just on the wrong side of the bed.

For example, I find inspiration from Ratatouille. Or Avatar. Or Admiral William McRaven’s UT Austin commencement speech. I feel grateful after watching The Blind Side. Yet, if I want to feel sad, I watch Thai life insurance commercials (here’s an example of one). Envy, from select friends’ Facebook/LinkedIn posts. Direction, from Kurt Vonnegut or Brandon Sanderson’s lectures. And the list goes on.

5. The Excite-o-Meter: Matt’s personal Stoke Diary

Matt: I’m a big believer that energy is palpable, but ephemeral. Like a wisp of smoke, energy is beautiful and can dazzle and inspire, but it fades… eventually. The buzz dies down, and it saddens me. That’s why I’ve developed a practice to immortalize positive energy – by keeping a running list labeled “Excite-o-Meter.” It’s my personal Stoke Diary.

Here’s how it works.

At the beginning of every week, I create a “dashboard” in a specific notebook I have for work –- a two-page canvas that I reference back to throughout the week. Page one contains items that I detail at the beginning of the week, like my “Big Rocks” (priorities for the week) and “Principles to Uphold” (personal growth tenets I aspire to embody). 

Page two is more dynamic. It contains running logs of moments that captivated me in the present, that I choose to immortalize.

I allocate 25% of page two to the “Key Learnings” of the week. But the real magic happens with the other 75% of the page. I label this section “Excite-o-Meter.”

My rule is that anytime my excitement exceeds a very scientifically-defined 7/10, I jot it down immediately. 

Reached alignment on a cross-functional project that was birthed out of a chaotic primordial soup of conflicting objectives? Jotted. 

Overcame a once-limiting belief, reminding myself that I hold the paintbrush against the canvas of my life? Jotted. 

My SQL query finally ran after debugging it for 24 minutes? Jotted.

At the individual level, it helps me memorialize the moment, etching it down onto my notebook and simultaneously, my mind. But when I read the log in periods of reflection, when I browse weeks worth of “Excite-o-Meter” entries – it reminds me of who I am. Of what gets me to tick. Of what makes me experience pure exuberance. It’s my Stoke Diary, and it’s my ever-growing source of inspiration.

6. Marriage counseling: A recipe for strong co-founder relationships

Two and a half years ago, after a conversation with one of my favorite founders, I stumbled across the parallels of marriages and co-founder relationships. Ever since, while I don’t do so with any element of regularity, I’ve found couple counseling to be a huge unlock to demystifying sticky co-founder dynamics, hell, even how to make amends with friends.

7. Restaurant recipes: It never hurts to ask

I stumbled across this one quite accidentally. So, one of the things I’m quite known for among my group of friends is that I like bringing a notebook with me almost everywhere. And there have been multiple times that for a party of two, I’ve been the first to arrive. In hopes to capture my thoughts and ideas before they dissipate into the cosmos, as soon as I am seated at the restaurant, I immediately start to take notes. Additionally, when I ponder, I tend to look around as if my eyes were bees just hovering above sunflowers in a prairie without any intent to rest on any particular nectary.

That, in effect, without even noticing it myself, makes me look like a food critic — to which I’ve been offered complimentary drinks and appetizers while waiting for my dinner guest. On occasion, they serve me something I wouldn’t have ordered myself and I love it. And well, being a curious home cook I am, I had to ask how they make it, in hopes of replicating the flavor and/or texture profile at home. And I remember the first time I worked up my courage to ask, the chef de cuisine hand-wrote out her full recipe and gave it to me at the end of the meal.

Ever since, every time I like a dish at a restaurant, I give my compliments to the chef and politely ask for the recipe. Most times I get a thank you but no, but surprisingly and anecdotally, about 40-50% of the time, I actually get the recipe. And in a small, small handful of times, the chef shows me how to make the dish live.

In closing

Most people don’t self-describe themselves as quirky. Neither do they seek to find a quirk that best describes them. Quirks are products of self-discovery and unadulterated problem-solving at its purest. Bespoke solutions to ones’ problems, unabated from society’s judgmental eye, birthed by the crazy ones. And that is something Matt and I find magical.

In fact, when Matt brought up this topic with his bud, Rebecca, recently, she described it best, “Quirks are an evolutionary adaptation. They stand out and persist because they survive. Because they are a survival mechanism. Everyone has a bunch of systems. I have a way of organizing my notes, packing my suitcase, curating my notes, and a bunch more.”

While the purpose of this blogpost isn’t for you to pick what quirks you like and copy them (while we won’t stop you if you do), rather, we hope this helps you better understand where quirks come from. And just maybe, this will help you build the blueprint schematics to what makes you you.

Photo by Mulyadi 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!

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 #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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Five Tactical Lessons After Hosting 100+ Fireside Chats

microphone, podcast, fireside chat

Over the past 12 months, I’ve done over 100 interviews and fireside chats. While there are the more popular lessons out there, like asking follow-up questions and breaking the ice with your guest with a pre-interview chat or having rapid-fire questions at the end, for the purpose of this blogpost, I’ll be sharing some non-obvious lessons I picked up in the past year.

  1. Never start with a question on career.
  2. Ask your guest three questions before the interview.
  3. Do enough research to be literate in the subject you’re interviewing for.
  4. Prep the audience for questions.
  5. Ask Yes / No questions.

Never start with a question on career.

The first question always sets the stage for the rest of the conversation, especially how vulnerable and candid the guest would be.

The best question in my experience to start with is always a surprise to the guest, as my goal for every interview is to get to know the guest better than they know themselves at that moment in time.

For how you measure success… if that respond with, “How did you know that?”

In practice, it looks a little something like… “I want to start this chat a little off-center. In the process of doing homework for this conversation, I came across the name: Bootstrapping Bill*. Could you share what that name means to you?”

*Footnote: This can be a high school or college nickname or an activity that they were heavily involved in that’s not related to their current career. Or a role model they had when they were younger. Other starter questions can be about quirks they used to have or still have that are:

  1. Not embarrassing
  2. Something that only they have.

For example, for some of my interviewees, I found out:

  • That someone used to write code on a notepad
  • A longtime fandom around Gary Keller
  • A nickname the guest used back in his street dancing days
  • A class they really enjoyed taking in college and an art professor who inspired her to pursue entrepreneurship
  • Someone who used to walk by foot 15 hours one-way just to go to a library in Cairo to download PDFs of Stanford research papers to take home and study

Of course eventually it all has to tie back to the topic at hand, which is usually through a trait they developed early on that created the person they are today. Grit. Creativity. Rebelliousness. Kindness. And so on.

Ask your guest three questions before the interview

To piggyback on the above lesson, don’t touch things that are highly personal and risqué, like their social security number or their divorce. The latter without their explicit permission. You never want to be in the situation where you make the guest feel bad. As such, in my email to them a week in advance with the questions I plan to ask, I ask an additional three questions to help give me parameters for the conversation:

  1. What would make this interview the most memorable one you’ve been a guest for even two years from now?
  2. Are there any topics you don’t want to talk about? Or are sick of talking about?
  3. Are there any questions you have yet to be asked, but wish someone were to ask you?

Of course, also share the questions that you plan to ask before the interview. Leave it up to them whether they want to prepare for them or not. And if you do so, they’re likely to bring more robust and less generic answers for your audience. Unfortunately, not always true depending on the individual you invite and how busy they are.

Do enough research to be literate in the subject you’re interviewing for.

Unfortunately, not every A-lister will bring their A-game. Some have been busy. Others are distracted. And a handful of others frankly just don’t care. For them, this is just another talk they’ve done a million times. Not THE talk of the year. Even if it might be for you.

Luckily, it doesn’t happen too often. But it does happen. And as such, you can’t just ask a question. Instead, I like to give the speaker enough time to think of an answer. I call it the QCQ sandwich.

  1. Start with a QUESTION.
  2. Follow up with CONTEXT.
  3. And close with the initial QUESTION.

I’ll give an example.

“Since you just mentioned LP-manager fit / I want to switch gears for a second… I’d be remiss not to ask you about how you think about it. In your experience, how have you seen the best fund managers think about LP construction when they begin fundraising versus when they’re about to close the fund? To shed some extra color, I’ve recently chatted with a number of emerging GPs. And there seems to be a concentration of thought leadership around… [additional context] So, I’m curious, are you seeing the same? Or have my observations departed from the median?”

Most people either only ask the question or lead with context before asking the question (I’m guilty of the latter myself from time to time).

To be fair, you may not need to use this structure all the time. But for people whose answers are typically less structured and may need some time to formulate a robust answer, this is the play. A proxy for this is if their answers only get better the more they talk or if they haven’t had a chance to look through the questions you sent them beforehand, but they typically like to.

Then there’s the exact opposite. Even if the guest speaker is well-intentioned, in efforts to cram as much info into an answer as possible, their talk becomes overly informational. I forget which world-class podcast host once told me this, but he said that that every episode he does is 20% informational and 80% entertainment. The footnote is that the 20% has to be so insightful that it can carry the episode just by itself. The sign of a good episode is if the listener walks away with at least one thing they didn’t know before.

I go back to Kurt Vonnegut‘s #1 rule on writing. Use the time of a total stranger in such a way that he or she will not feel the time was wasted.

As the MC, your goal is to be the steward for insights. The spotlight is never on you, but the question is how do you support your guest in a way that they’re able to put the best foot forward.

Prep the audience for questions

There are two angles I usually tackle from when prepping the audience for questions.

  1. I tell them exactly what they can ask at the beginning and stay away from those topics so that the audience can ask during Q&A if they have no other questions in mind.
  2. Give the audience time to ramp up questions by alternating between live questions and my prepared questions even in open Q&A.

“We’re going to cover a lot of ground today from [topic 1] to [topic 2] to [topic 3]. But if I don’t get to all of them, and you’re still curious about them, please keep us accountable during the open Q&A after.”

And I usually don’t get to all of the above topics, which leaves room for the audience to ask them. Before I ask my “last” question for the interview, I also tell the audience to the effect of: “This is going to be my last question, before I turn it over to everyone present today. So for anyone who would like to ask X something, in about 3 minutes, it’ll be your time to shine.”

The big takeaway is that it always takes a bit of time for the audience to ramp up to ask their questions. And this helps seed some possible topics not covered in the interview so far, so the guest also feels like they’re not repeating themselves.

Since almost every interview and fireside chat I’ve done has been virtual in the past year, this second tactic is designed when you a Zoom chat but I find is still useful when you have a shy live in-person audience. I always tell the audience to leave questions in the Zoom chat at the beginning of the interview. That I’ll call on them when we get to open Q&A. More often than not, the Zoom chat is less alive than I would like. And when it is (and I admit this has only been a more recent discovery of mine), I say:

“We’re going to try something new. During the open Q&A, I’m going to alternate between questions I’ve gotten before this chat to live questions from the audience. So feel free to pop your questions into chat, as I start with the first pre-submitted question.”

I know some MCs seed audience members to ask questions at the beginning of live Q&A for it to not seem awkward. I’ve seen it work, but sometimes I’ve also seen those 1-2 people take control of the Q&A, where the rest of the audience doesn’t feel like they have the opportunity to ask their own question, so they turn passive. With open Q&A, I try to give my audience agency to determine the flow of conversation. Sometimes, they just need an inspirational nudge.

Ask Yes / No questions

For a long time, I had this fear of asking yes/no questions during fireside chats. The main reason was that I believed it would lead to a lackluster interview. The guest would give a one-word response and that we would have radio silence after.

But, contrary to my initial belief, I realized over the past year that yes/no questions are insanely powerful, specifically in the context of public interviews and fireside chats. I do want to note that they don’t hold the same weight in mediums that are known or sought for their brevity. For instance, emails and instant messaging. Where speed is the name of the game.

It’s specifically under the circumstance where there’s an allotted time and an expectation to fill the void with content that this tactic shines. The guest would more often than not feel an urge to fill the empty void with additional thoughts and context. In that moment, sometimes they share something that is more off-the-record than they initially planned. Of course, in realizing that it is, and since most of my fireside chats are recorded, I follow up with the guest after to make sure they’re okay with the recording.

As an interviewer, at the same time, I’ve learned to hold myself back. There’s an equal if not more powerful urge in me to fill the void with questions. After all, oftentimes, this is the audience in which I had invited, and feel my reputation is on the line. If you could see below the camera, I have a sheet of paper in front of me where I write “Shut up” to myself at least twice before I jump in.

In closing

While I share all the above, just like being a founder, you could do everything right and the interview may still fall short of being ideal. And when some interviews do fall on either deaf ears or I feel I was just unable to bring out the best in people, like many others, I wonder… do I just suck at being at asking questions? Or being an MC?

It’s an iterative process. And the fun part of it all is that it makes me a better investor. I ask founders better questions. The answers I get when diligencing are more valuable.

The above isn’t the end-all-be-all. I’ve written on this topic before, and I will continue to work to be a better interviewer. But hopefully the above serves to bolster your arsenal of tactics.

Photo by Keagan Henman on Unsplash

Edit: Added in a fifth lesson that’s too short for a full blogpost, but longer than a tweet.

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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The Eight Rules of Great Pitches

Over the week, I was revisiting some of the Instagram posts that I had saved over the years, and I re-discovered one of my favorites by Christoph Niemann sharing his kudos to the late Kurt Vonnegut.

Most of all, Vonnegut’s advice on writing applies just as much to other forms of storytelling. And if you know me, I was immediately reminded of pitching.

  1. Never waste someone else’s time.
  2. Give the listener someone to root for.
  3. Every character should want something, even if it’s a glass of water.
  4. Every sentence must do one of two things — reveal character or advance the action.
  5. Start as close to the end as possible.
  6. Be a sadist. Show awful things that happened to the characters.
  7. Write to please just one person. Don’t get pneumonia.
  8. Give your readers as much information as possible as soon as possible.

Never waste someone else’s time.

Teach your investor something they didn’t know before.

A lot of investors claim to be experts, and even more are seen as experts. Too often, founders blindly listen to what their investors tell them to do. As Hunter Walk of Homebrew once said, “Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.”

YouTuber Derek Muller just came out with a great video on the ideal variables that manifest expertise. Two of such variables are:

  1. Valid environments – environments that are predictable and have minimal attribution to luck
  2. Quick feedback loops

The problem with venture is that our feedback loops are incredibly long and drawn out. Oftentimes, it takes 7+ years to fully realize any kind of financial outcome, although there are many red herrings of outcomes in between, like new funding, brand-name investors, users (rather than customers, or people who actually pay for your product), mass hirings, and so on. Because our feedback loops are slow and luck plays a huge role in success, it’s hard to differentiate true experts in the field. All that to say, every investor is learning to be better, to have more data, to make better judgments than the next.

And if you can show that you know something worth our time again and again, it’ll be worth paying our tuition money to you.

That said, I don’t want to discount how some investors can be really helpful in particular areas that have valid environments and fast feedback loops. For instance, code, A/B testing distribution strategies, ability to help you raise your next round within a certain timeframe, or get you into Y Combinator. The determinant of success in the afore-mentioned has clear KPIs versus their own financial success in the fund.

Give the listener someone to root for.

Aka you. Why you?

Mike Maples Jr. once said, “We realize, oh no, this team doesn’t have the stuff to bend the arc of the present to that different future. Because I like to say, it’s not enough. […] I’d say that’s the first mistake we’ve made is we were right about the insight, but we were wrong about the team.”

“I’d say the reverse mistake we’ve made is the team just seems awesome, and we just can’t look past the fact that they didn’t articulate good inflections, and they can’t articulate a radically different future. They end up executing to a local maximum, and we have an okay, but not great outcome.”

There’s a category of founders that are going to win no matter if an investor chooses to invest or not. Most typically like riding this train. They have to do little to no work to be recognized as a great investor.

Then, there’s the cohort of founders that may or may not win on their current idea, but their investors really, really, really want these founders to win. These founders are the underdogs. They’re also the ones with often the craziest of ideas. Even more so, they’re the ones that if they win, these founders will redefine the world we live in today.

As a founder, you have two jobs when fundraising:

  1. You need to find the partners who really, really want you to win. As the great Tom Landry says, “A coach is someone who tells you what you don’t want to hear, who has you see what you don’t want to see, so you can be who you have always known you could be.”
  2. You need to give these partners the ‘why.’

And I promise you that ‘why’ is not because of straight facts, but because of a story. Why should people help you get what you deeply want?

Every character should want something, even if it’s a glass of water.

Speaking of what you deeply want, almost every founder I chat with pitches me their raison d’etre. A selfless reason to cure the world of cancer. Metaphorically speaking, of course. That’s cool. You can tell that to the press. It’ll make great PR.

Rather I care about the exact opposite. What is your selfish motivation? This is a question I personally like asking founders. Your selfless motivation keeps you going during the day, during peace-time, when things are going just right. Your selfish motivation keeps you up at night, when s**t gets tough. When no one else believes in you except for yourself.

I want to know that you want that so badly, that you’re able to go the distance. And if that same thing is something that your investor can relate to, then you have a match made in heaven.

Every sentence must do one of two things — reveal character or advance the action.

Let me revise the above. Every slide must do one of two things — reveal character or advance the action. Anything else is superfluous. That means, outside of your core slides — problem, solution, action plan/financial projections, rising conflict (aka competition, blockers and risks), and your team slide, everything else is superfluous. Or at least, save it for your data room.

I’m sure some investors would debate me on this, but every investor has a slightly different framework. The above is my own perspective. That said, every slide should give an investor 10% more conviction towards investing in your business — capping out at 70%. ‘Cause after 70, any additional information (in the first meeting) has diminishing returns.

Start as close to the end as possible.

No investor cares about which hospital you were born in, but they do care about when the fire first started. And they care about your inflection points, even if that’s still ahead of you.

Be a sadist. Show awful things that happened to the characters.

Grit is one of the hardest founder traits to measure over a 30-minute meeting. Even after prolonged and deliberate interaction, most of the time it’s still hard to grasp this amorphous quality. But if you ask most investors what is the number one trait of a great founder, it’s either grit or passion. The latter of which often serves as a proxy to grit.

If you’re regular here, you know one of my favorite quotes of late is Penn and Teller’s. “Magic is just spending more time on a trick than anyone would ever expect to be worth it.“

Past performance is not a predictor of future progress. But it really does help. A lot. In a startup’s lifespan to becoming a leading business, there are 10-15 trials by fire. And for each one of those, the founders are required to pull off nothing short of a miracle. In fact, this next year will be exactly one of those tribulations for 99.9% of companies.

So, show moments in your life where you were able to pull off a miracle. And a miracle, by definition, is when the odds are heavily stacked against you.

Show excellence. Walk your listeners — your investors — through the journey of how you tasted glory. How you were able to achieve the seemingly impossible. Personally, this is why I love backing professional athletes, veterans, and chefs. Three fields (of, I’m sure, many more) that you really need to eat s**t to be one of the greats.

Write to please just one person. Don’t get pneumonia.

Every pitch should be tailored. Why would this investor be the best dollar for your cap table?

No investor (even if it’s true) wants to be just another investor. They want to be THE investor. Make them feel special. When you propose to your partner for marriage, you tell them why they’re the one for you, not why you’re the one for them. You get down on one knee and tell them why they are amazing. Not the other way around.

Give your readers as much information as possible as soon as possible.

The one-liner matters. It is the first point of interaction with your startup, and oftentimes, may be the last. Don’t shroud it in mystery and jargon. If you’re ever stuck here, remember Brandon Sanderson‘s First Law of Magic:

“Your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.“

Equally so, the subject line of a cold outreach email serves the same purpose. This is especially true, when you’re reaching out to someone who you can reasonably assume has hundreds of emails in their inbox per week. For reference, and for the most part I’m a nobody compared to the partners at a16z of Lightspeed or Benchmark, and I get about 50 cold inbounds per week.

So, in my opinion, your subject line should have no buzzwords (well, because everyone’s using them). Think of it this way. Say you’re an author selling your new self-help book. And say your greatest distribution channel are likely bookstores in airports. If everyone in the self-help section has an orange cover with bold blue words, you want to be the one black and white cover book. And if everyone has black and white sleeves, you bring out the neons.

In the context of email subject lines, instead, you should include numbers. What is the one metric that you are killing it at? Just like what I recommend folks write in their email forwardables. Instead of “Invest in the Leading BNPL Solution in Latam”, use “BNPL startup growing 50% MoM”. Give the exact reason why your investor should be excited to invest in your company. Don’t save it behind eight clicks — Email, Docsend link, and another six clicks to get to the slide of importance.

People can only tell different, not better, unless it’s 10x. Mediocrity is a crowded market, so don’t waste your time there. Taking a quote out of Pat Riley‘s book, “You don’t wanna be the best at what you do; you wanna be the only one who does what you do.”

In closing

Storytelling is an emotional discovery. The facts don’t change, but a great pitch or story weaves seemingly disparate facts into a compelling narrative. One that inspires action and draws curiosity. In a saturated world of attention, you are fighting for minutes if not seconds of someone’s time. Make it valuable.

Photo by Daniel Schludi 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!

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 #64 An Intellectual Renaissance

“Good writing is always about things that are important to you, things that are scary to you, things that eat you up. But the writing is a way of not allowing those things to destroy you.”
— John Edgar Wideman

I go through these sinusoidal episodes where I write about my journey as a person. A world where things just aren’t perfect. And I, like everyone else who graces this planet, am struggling to find where I fit in the world. And when I’m swimming in the depths of self-discovery, I find that for an audience of entrepreneurs and investors, I really haven’t written much about my discoveries and re-discoveries in the wonderful land of innovation. The other half of it is for my fear of knowledge atrophy.

And so, I spend back to back to back weeks writing about the inner workings and the robust mental models of some of the world’s top intellectual athletes. Then in hindsight, once again, I realize that my blog begins to read just like any other business blog – any other startup, VC, tech blog – out there. And I fear that I’ve lost my voice. So, I re-embark on a literary path of introspection and growth.

The great Charlie Kaufman once said about his time on Adam Resnick’s show, Get a Life, “Adam Resnick’s scripts were the best on the show. And we all tried to write in Adam’s voice. That was the job. And I was frustrated with my results. But it occurred to me that there was no solution to this problem as long as my job was to imitate someone else’s voice. I can maybe get close but I was never going to get better at it than Adam.

“The obvious solution was not to throw my hands up but try to find myself in a situation where I was doing me, not someone else. Do you. It isn’t easy, but it’s essential. It’s not easy because there’s a lot in the way. In many cases, a major obstacle is your deeply seated belief that ‘you’ is not interesting. And since convincing yourself that you are interesting is probably not going to happen, take it off the table. Agree.

“Perhaps I’m not interesting, but I am the only thing I have to offer. And I want to offer something. And by offering myself in a true way, I am doing a great service to the world. Because it is rare and it will help. As I move through time, things change. I change. The world changes. The way the world sees me changes.”

As a product of what I can only describe as a game of tug-of-war between my right and left brain, I start many essays and unfortunately, lose interest half-way through writing them. As such, I’ve amassed a far-reaching graveyard of zombie posts. Eclectic, disparate monologues. Neither fully alive nor fully dead. Some may see a phoenixlike revival. Others may forever rest as vestigial drafts until Indiana Jones excavates them.

But nevertheless, the act of writing to think – to express – hones my mind like a whetstone to a kitchen knife. The more I do so, the sharper I get. Yet too much so, without application, renders the act of sharpening useless.

A few days back, I stumbled across a fascinating tweet on atrophy and hypertrophy.

There are many things in life that atrophy over time – knowledge, skills, presence. Yet there are a handful of things that hypertrophy – brain, demand for proof, and space, just to name a few. For me, writing exists in both categories. Like most skills, it is perishable. Yet the more I see, hear, and learn, the more I demand to myself that I need to put pen on paper. A personal intellectual renaissance.

Photo by Ágatha Depiné 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 or investment advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.

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DGQ 12: What is play to you but work to everyone else?

children playing, not work

What is play to you but work to everyone else? Or said differently, what do you love doing that many others would hate or get bored of quickly?

This isn’t an original self-query. I want to say I heard it years ago on one of Tim Ferriss’ episodes, but the exact one escapes me. Yet, recently, my friends and colleagues remind me of this more and more. In the ultimate shortage of labor, more than ever before, people are rethinking what career means to them and what a meaningful career means. I’ve had friends become full-time live streamers, NFT creators, inventors, fiction novelists, artisans… you name it, and I bet you someone that I know – hell someone you know – has dabbled or jumped head-first into it. It truly is the era of the Great Resignation.

Now this question isn’t a call to arms to leave whatever you’re doing. Rather a direction of clarity that may help you live a more enriching life. Something to pursue in your down time. Until you can find a way to get paid to do so – unless you happen to have 20-30 years of runway from previous riches. The same is true if you’re an aspiring founder. Work on your project part-time, until you are ready to take it full-time either with investment capital or revenue.

For me, the answer to the above question is:

  • Writing (to think)
  • Meeting, and more specifically, learning from passionately curious and curiously passionate people (what can I say, I’m a glutton for inspiration)
  • Becoming a world-class questioner (you’ve probably guessed this one from the DGQ series)
  • Collecting quotes and phrasings that resonate (a few of which are repeat offenders on my blog)
  • Helping people realize their dreams (something that was much easier when I only had 20 friends, but much harder when I’m adding zeros to the right)

Many of the above have become synonymous with my job description over the years. Did I predict I would fall into venture capital? No. Frankly, it was a result of serendipity and staying open-minded to suggestions from people I really respect.

While this may come off as virtue signaling, to me, I’m willing to, did lose, and continue to lose sleep over each and every one of the above activities. And if I know anything about myself, my goalposts are likely to change over time. Not drastically, but fine-tuned over time.

Photo by Robert Collins on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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v26.0

I spent the majority of my 25th year of being alive in 2021. A year of Yes’s. A year of unexpected surprises created by increasing the surface area in which luck can stick. And by transitive property, I intentionally opened myself up for exploration. Some might call them distractions. For me, they were the scenic route. A route that may or may not change the final destination. But I will only know the robust or flawed nature of my initial destination if I take Highway 101.

And quite expectedly, I said “Yes” to projects that would push me past my “limits.” In foresight, scary. Might I say, fearfully challenging, plagued with self-doubt. Yet, just one question kept pushing me forward while I sought the comfort of being a blanket burrito.

What if this were easy?

Synonymously, if I were the world’s leading expert on this topic, how would I approach this? Not only tactically, but also emotionally. Or oftentimes, lack thereof.

In hindsight, I usually realize I had handicapped myself with training wheels all these years. I am nevertheless proud to say I would have surprised the me on the cusp of 25 years young more than twice given this past year.

This year will continue to be a year of Yes. And, I will undoubtedly continue to surprise myself. Shock will continue to be my currency of growth. Not from others, but by myself.

I have spent a lot of time thinking whether annual goals are the best forms of motivation for a myopic human like myself. I have given into short-term gratification more often than I can count. This past year, the near-term “Yes” is closely correlated with fried chicken and hojicha. Sorry, they are my Kryptonite. It’s unfortunate that my mom dipped me into the Styx holding both rather than just one of my heels.

If I hadn’t gone through my birthday resolutions of my 25th year I wouldn’t be here today. And it wouldn’t have led to the v26.0 software update as it stands.

My latest software update

As such, by 27, I will have spent at least twice a week getting into the flow state – inspired and courtesy of my colleague Edgar Brown. What is the flow state? As one of my good buddies describes it, “the flow state is a state you enter when you feel the most alive and creative. You’re 100% immersed in the activity you’re doing. It’s a completely egoless state. You don’t care – and frankly, forget – about what other people say. Yet after going through the flow state, your ego strengthens and becomes part of your identity.”

Of a similar vein, creativity is also very much a luxury I would like to indulge in more, shackled only by my minor, but noticeable discomfort with idle time. An unfortunate byproduct of my occupational hazard, otherwise known as “hustle porn” as Alexis Ohanian of Reddit fame so elegantly describes it. In year 26, I will have found profound solace in cold silence, where one would find comfort in the absence of speech, as opposed to hot silence – silence that is awkward. And in these weekly cold silent flow states, I hope to better identify my own signal amidst the noise.

In closing

Before this essay sounds any more like a wannabe doctorate dissertation, I hope that in writing this for the public eye, I can better hold myself accountable for my goals.

I hope there will be no consecutive offenders to my resolution list. Since it’ll mean that after a year, I still haven’t broken into the habit I want to build for myself. And it’s that delta between promise and reality that’ll have me going back to the drawing board again. And if you ever see that there are, this blog will keep me honest for failing on my promise to myself. While I imagine there will be repeat offenders by product of growth-inspired oscillations, I am at the end of the day a constant work-in-progress.

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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DGQ 10: Questions Should Not Be Perfect

perfect questions, reflection

Straight off the bat, you might have realized that the 10th issue of the DGQ series – damn good questions – starts off with a non-question. And it is intentional by design. I often waste a number of calories constructing the perfect question. And in many ways, I get very, very close to what I deem as perfection. Exhibit A, B, and C.

But over the course of constructing the perfect question and its subsequent research, I often uncover the answer I am seeking… before I even ask it to the intended designee. I don’t mean for the odd question here and there amidst spontaneous conversation. But the predestined ones to be asked in:

  • Fireside chats
  • Intro conversations
  • Coffee chats with individuals where I’m punching above my weight class
  • Podcast interviews
  • Social experiments
  • First dates (possibly self-incriminating)

Accompanied by the excuse of creating conversation, I ask it despite the since-acquired knowledge. Sometimes to the wonder and amazement of the recipient, but more often than not to the boredom of myself. While the words that flutter out of my mouth may sound like a question, it ends up merely being a statement rearranged on a NY Times crossword puzzle.

In reframing questions for myself, I realized… If I knew all the answers to the questions I would ask, that’d make for quite a boring life. While boredom only surfaced a minority of the time, it occurred noticeably enough times. If I had a mirror to myself every time I asked a question, I imagine I would find myself asking the ones I have the answers to already with a furrowed brow.

Last year, in the relentless pursuit of being a better host for structured conversations, I over-optimized for shock and delightful surprise. Shock became my unfortunate currency for my personal delight. Rather than enlightenment, education, and inspiration. In the construction of the “perfect question,” while protecting my downside – in terms of embarrassment, I capped my upside.

So, this essay is a reminder to myself. Ask dumb questions. It’s okay. It’s only by reinventing yourself again and again through the ashes of unintentional ignorance can you rise like a phoenix.

I’m reminded of a quote by quite a contrarian philosopher, Karl Popper, but nevertheless quite appropriate here. “Good tests kill flawed theories; we remain alive to guess again.”

If you’re reading this essay, be prepared for a lot more dumb questions from me. Dumb, not garbled. Dumb and simple. I’ll continue to do my homework before conversations. But if I’ve found the answer already, I’m going to keep myself accountable to either find new questions or cancel the meeting. Cheers to the motif of exploration! And I’ll see you where I cannot foresee.

Photo by Faye Cornish on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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