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.


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v25.0

Life is not measured by the number of breaths you take but by the moments that take your breath away. – Maya Angelou

Year 24 was a mediocre year. I was too ambitious, having made my birthday resolution public for the first time the year before. Not in the sense I tried to bite off more than I could chew. But in the sense, I lost focus. In trying to focus on everything, I focused on nothing. In my pursuit of hitting all the marks, I became mediocre at all of them.

Don’t get me wrong. Despite the pandemic, which may have hindered some of my goals, namely:

  • Getting two startups from 0 to 1 in a year,
  • And sleeping earlier,

… I did “succeed” in all of my other endeavors. Frankly, some hit, some missed. Nevertheless, I didn’t become stellar in any one of them. Looking back, I’m almost embarrassed to say any of my resolutions were defining of my 24th year being alive on this planet.

So, no concrete compartmentalized goals this year. I will be living day-to-day with one goal in mind: I have to seriously impress myself at least twice this year. While I may not have “actionable” goals to head towards this year, in order to impress myself, I have to, what some might call, “risk it for the biscuit.” I have to take leaps of faith. I have to be willing to try and fail and try and fail. Because without trying and taking risks, I know for a fact, I can and will never impress myself.

Of course this goal is subject to change, although I imagine not by much. The past year has taught me how unpredictable our future is. Who am I to predict what I will do the rest of this year when even the best fortune tellers and professional investors cannot forecast with certainty what will happen next week. Be it $GME or the pandemic, I’m sure life will constantly throw us curveballs we will never be able to forecast. But that’s exactly why living is fun. The future is not the present we are gifted, but one we chase not knowing what’ll come of it. And the gift is in the adventure.

I quoted James Stockdale – for which the Stockdale paradox is named after – in a post last year, “You must never confuse faith that you will prevail in the end – which you can never afford to lose – with the discipline to confront the most brutal facts of your current reality, whatever they may be.”

To confront myself and the most brutal facts of today, I will take the risks that will mold who I am tomorrow. The discipline of saying yes. It’s not about my batting average, but about the magnitude of the home runs I can get.

I’m confident that this year, I will continue many of the habits I picked up in the past year – writing weekly, exploring creative projects regularly, etc. But I won’t hold myself to promises that’ll lead me to mediocre, or at best, good, results. But rather, like in venture, I have to be willing to pass on the ‘good’ to make way for the ‘great’.

Photo by Luca Bravo on Unsplash


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#unfiltered #28 The Little Things

morning, the little things

Over the past few weeks, California has been plagued with wildfire after wildfire. It got me really thinking about what I miss.

I had a birthday resolution to run more to achieve a sub-5 mile by running in my neighborhood regularly. I used to manually water the plants in our backyard, especially my kumquat blossoms that finally bloomed after 2 years. And, I used to keep my windows open so that fresh air could fill the house.

The smell of dew and the brush of chill in the morning. The smell of freshly-cut grass in the afternoon. And the evening dinner aromas that pervaded our cute suburbia.

Then, everything changed when the Fire Nation attacked. When the smog came to our neighborhood, I no longer had that luxury. Rather, I spent my time indoors, and a few days back I wrote this in my journal.

The Little Things

Silence of the jay,
Crimson ochre dyed the sky,
Tumbleweed astray.

New kumquat blossoms
Birthed from labor, yet scorched by
Ashen canopy.

A resolve to run,
Yet I am basking under
A bright midnight sun.

Taken for granted,
A life I thought I knew well
And now much better.

Inspired by the lost
Cherished more when found, come forth
Will the little things.

Appreciating life

What else do I take for granted? What else will I deeply miss when I no longer have but aren’t fully appreciating now?

The first answer that comes into my head – the people around me. My family and my friends.

Photo by Dawid Zawiła on Unsplash


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


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Self-Assessment (VC Scout) circa April 2020

vc scout reflection
Photo by Marc-Olivier Jodoin on Unsplash

This year in my resolution, I aim to be more vulnerable by “opening up about the potholes ahead, not just the ones in the rearview mirror”, to quote Jeff Wald. So I’m going to take a step closer to doing so.

Yesterday, my buddy asked me a question that didn’t sit well with me. Not because he was rude, nor because he meant to offend me. In fact, for all intensive purposes, it was entirely innocuous. But it was a question that got me to really question my beliefs and do an impromptu performance review of myself. He asked:

“Out of all the startups you’ve met with and had the chance to source, how many do you regret passing on? Which one or two stands out to you the most?”

I paused for a second. But when words arose to my mouth, my reply was simple. “I don’t think I have any regrets.” As soon as I said that, I immediately felt this gnawing feeling that something was wrong. I’ve always chosen to live life without regrets. And though this may seem to run parallel to my mantra, I knew deep down it wasn’t meant to be.

Luckily, I have had more time to introspect than otherwise during this pandemic. There are 3 possibilities as to why I have no regrets:

  1. It’s too early to tell which ones will be home runs.
  2. I’m not being selective enough, aka I have a flawed investment thesis.
  3. I don’t have the kind of quality deal flow I would like.

While optimistically, I hope it’s the first possibility. After all, it’s only been 3 years since I embarked on this journey. And there probably is a small proportion of startups that will go on to prove me wrong. Realistically, it’s a permutation of the latter two.

Currently, I pick about 40-50% of my inbound (referrals/intros, cold pitch emails/messages, various networking apps) and 100% of my outbound (assuming they get back to me) to have a conversation with. Of those, I usually find 1 out of every 10-15 that I continue the conversation with from an investment standpoint. And out that pool of founders, I usually end up referring 50% of them. Meanwhile, I still try to be helpful in some capacity to everyone else, but only spend about 20% of my time to do so. From a high level, I couldn’t see anything wrong with this funnel. At least, not until my buddy asked me that question.

Sourcing is one of those things that’s easy to pick up, but difficult to master. And now, I feel, not just conceptualize, how steep this learning curve is. There’s a saying in the industry that “luck only gets better with success.” But I have yet to pay the admission fee for my luck to start compounding. So there’s 3 things I have to do:

  1. Reevaluate my current deal flow by analyzing inbound sources and the empirical quality from each (# of startup I’ve introed/total # of startups received from X source).
  2. Hit up the investors I know to help me create a more robust thesis.
  3. Double down on helping my existing deal flow reach their aggressive milestones, until hopefully, the first can hit the ground running.

On the brighter side, it’s great that I’m iterating on this now before I become a checkwriter.


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What Does Personal Progress Look Like?

In the past two weeks, through conversations on my birthday resolution and what my success metrics are, my friends inspired me to write this post . That’s when you know I’m in Silicon Valley! Or startup Disneyland.

So, how do I measure my progress? This is by no means proprietary or original. In an annual email exchange, my mentor had me ask myself one question:

How ashamed do I feel about myself one year prior?

Although not comprehensive, I find it to be a great litmus test for evaluating personal development. If I don’t scoff at my former self for being dumb, I’ll know I haven’t progressed. At the same time, I put myself in the shoes of my future self, abstracting myself from my status quo, and ask two questions:

  1. What aspects of my past self am I embarrassed to see?
  2. What strengths of my past self would I find extremely unimpressive to show off?

This acts as an ego check and helps me look at myself more objectively.

I started this practice two years ago where I keep a checklist (on Google Keep) of wins I keep track of throughout the year. It included any magnitude of achievement, like:

  • A successful deal close;
  • Joining as a guest on a podcast;
  • An art piece I’m proud of drawing;
  • Cooking a meal that pleased my parents;
  • And, sleeping 8 hours a night.

Then one week prior to my birthday, Google Calendar reminds me to go through that checklist and review what I still feel proud of and what I find to be ‘normal’. I check all the ones I no longer gain contentment from. All that’s left are “My Proudest Moments at Age XX”. Then my goal for the following year is to make those moments feel ‘normal’. I’ll get to this step eventually. But I plan to review the annual lists every 5 years to see if I still feel the same.

In a way, this blog is also designed for me to reflect on earlier iterations of myself through my writing. As much as this one question has enlightened me, I hope it may act as your heuristic for your growth.

v24.0

Photo by Ian Schneider on Unsplash

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

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

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

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

Here are the patch notes:

Build ideas from 0 to 1.

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

More artistically creative outputs.

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

Balancing Social Media.

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

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

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

Reconnecting.

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

Read more.

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

Sleep and wake earlier.

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

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

Goal-oriented exercise.

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

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