Category: Life

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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

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

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#unfiltered #39 Five Lessons from Trying to Engineer Serendipity in a Virtual Environment

startups, spark, how to engineer serendipity, social experiments

Over the past few months, I’ve been slowly experimenting with how I can take Hidden Questions online, while not sacrificing the intimacy of the relationships it builds as well.

Hidden Questions started as a question game I played with friends and colleagues, which eventually expanded to other strangers. The goal of which was to deepen our friendship within minutes rather than weeks, months, or even years. In sum, a game where each person has to answer the question truthfully, but is not required to reveal what the question is. The catch is that if the person decides to conceal the question, they have to take a “punishment” (i.e. crazy hot sauce, disgusting foods, durian, Beanboozled jelly beans, etc.). Before they decide to or not, other participants can ask clarifying questions, as long as it’s not “Is X the question?”, and bet additional units of “punishment” if the answeree chooses to conceal the question. Of course, if the answeree does reveal, the people who bet will take the “punishment” instead.

Some references:

What’s changed?

After over 30 sessions in the past 3 months, a few things have been hotfixed since the in-person game:

  • One-time perishable links – While not the be all end all, vua.sh lets us create a “secret messages” where only the people with the link can access the question – and only once. Once the link is opened once, it’s dead. So, this gives folks a peace of mind knowing that no one can go back and find out what the questions are. The people who create these questions are the last group/individuals who play.
  • One-slide Powerpoint presentations, reminiscent of Jeopardy, with increasing risk/depth factor of questions, scaling punishments with question difficulty/depth.
  • Mailing the “punishments” to the people I’m playing with, like Sean Evans and his team does for their show, Hot Ones, where they mail their 10 hot sauces to their guest before the interview. This way, I can keep people accountable to the punishments
  • Zoom, or an equivalent web conferencing tool – Social distancing at its best. Even better now, ’cause I get to play with people outside the Bay Area as well.

The five lessons I learned

  1. Total conversation time virtually = 100%. Total conversation time in-person > 100%.
  2. First answer makes a difference.
  3. For group calls, preface with introspective intros.
  4. The “extroverts” take over.
  5. Take the bio break.
Continue reading “#unfiltered #39 Five Lessons from Trying to Engineer Serendipity in a Virtual Environment”
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Predictions Are Popular

Predictions are in season. It started back during the holidays. A number of my friends, colleagues and folks online have been making predictions of what is going to happen this year. And I’m sure some are sure to hit. Many to miss. Since I’ve been reasonably active on Quora and given my role in the startup community, many people have asked me: “What are some of the best startup ideas to start in 2021? In 2022?”

Over the past year, the pandemic became a forcing function for late majorities and laggards of the adoption curve to pick up newer social and technological trends. Subsequently, accelerating many timelines. Timelines that would have otherwise been realized two, three, maybe even five years out.

  • Social is back.
    • Consumer social has been back. The pandemic has saved on average 2-3 hours of travel time per day for the average worker, job-permitting. At the same time, quarantining has reduced, if not eliminated, many in-person interactions with friends. More time means people seek to find more places to place their attention.
    • Enterprise social is here. The pandemic has forced many businesses to go remote. Similarly, there’s been a migration away from metropolitan/urban areas to save on rent, as well as an opportunity to not be shackled by geography in the past few months. Now, as well as “post-pandemic”, businesses, as well as individuals, are looking for new ways to improve efficacy, communication, and culture at work. In efforts to both retain and attract talent.
  • Impact-driven and socially-responsible businesses are hot.
  • Diversity in the board room is gaining traction. And it’s created ripple effects in the financial world. LPs are demanding venture funds to invest in diverse founders. At the same time, when diverse founders consider which investors to bring on, they look at if the checkwriters at the firm are diverse. Some investors have acted proactively; some reactively. Nevertheless, the cogs are moving.
  • E-commerce, entertainment, streaming, gaming, remote tools, edtech are all up.
  • SPACs and 2020’s string of IPOs have created many “overnight” millionaires.
  • Investing in the stock market, in alternative assets, in syndicates, and more mean more capital is being recycled back into the economy at various stages.
  • There is more capital available at the early stages. New angels. More startups. Just like pre-seed/seed is the Series A from a decade ago, more institutional investors will move upstream. Who knows, there may be a pre-pre-pre-seed round one day.
  • Innovation around the home office space is building momentum.
  • Unsurprisingly, Zoom fatigue is real, which will only led a hand in hybrid work-life models post-pandemic. Equally so, innovation around virtual meetings is only a matter of time.
  • Oculus brought down the price of a VR headset to be as much as a video game console, which means more people can and will adopt VR. Leading to larger markets and more diverse consumers for VR/AR. More startups.
  • Mental health has taken center stage, where it had previously been overlooked or disregarded.

When will the pandemic end? I don’t know.

When will we get vaccines? While experts have given us an expected date, I also don’t know.

When will “normal” return? I’m willing to bet it’s on the magnitude of years rather than months. Then again, will “normal” ever return? I might be completely wrong, but I’m willing to bet the “normal” we knew will never return. But instead, we’ll have a normal 2.0.

In truth, I can only answer what I see in my very narrow periphery. And by definition, there are a hundred-fold more that are in my blind side. And the thing is, what I’ve thought of I guarantee many other founders have already seen, tried, or are trying. What I’m looking for this year, and every year, is what I haven’t thought of yet. But when I hear and see it, it’ll click. Everything I know will make sense.

Investors are lagging indicators of innovation.

Founders are the leading indicators. Listen to them.

Photo by Nathan Anderson on Unsplash

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#unfiltered #38 Warren Zevon, Hockey, and Ambition

Having lived under the proverbial rock for most of my adult life from music, I recently learned of the late Warren Zevon. Particularly in his last appearance on his friend David Letterman’s show in 2002. He had been diagnosed with terminal mesothelioma. In other words, lung cancer, with about a year to live.

Letterman asked him one rather profound question, “From your perspective now, do you know something about life and death that maybe I don’t know now?”

And Zevon responds back with an equally, if not more profound answer, “Not unless I know how much-… how much you’re supposed to enjoy every sandwich.”

Needless to say, I was quite intrigued, which I wasn’t shy about sharing with my friends. One of such conversations was with my mentor. Someone who had followed Zevon’s career with a higher-powered magnifying glass than I did. And, he said, if I were to truly appreciate Zevon’s craft, I had to listen to his song Hit Somebody!.

Hit Somebody!

The song is about Buddy, a Canadian farm boy, scouted to be a goon, whose role on the hockey team is to defend the the top scorers of the team. Needless to say, dirty and violent play is part of the job description. While Buddy greatly distinguishes himself in his role, even to be hailed as the “king of the goons”, he wishes to be someone greater.

“Coach,” he’d say, “I wanna score goals”
The coach said, “Buddy, remember your role
The fast guys get paid, they shoot, they score
Protect them, Buddy, that’s what you’re here for

[…]

He never lost a fight on his icy patrol
But deep inside, Buddy only dreamed of a goal
He just wanted one damn goal

After “twenty years of waiting”, one game, he finally gets the chance. He shoots. And he scores, after getting dropped to the ice by a Finnish goon. And in his dying breath, in a poetic sense of wordplay.

‘Cause the last thing he saw
was the flashing red light
He saw that heavenly light

My thoughts

We often identify ourselves by our job title. In college by our major. In grade school by our grades and extracurriculars. By our past accomplishments, and not enough on those to come. We’re so often trapped in our own microcosm of “rules” and labels. Rules either society has reinforced or rules that we have capped our own potential with.

But that is exactly why I bet on people who live in the future. Because those ambitious enough to dream are the ones who are most likely going to turn those dreams into reality.

That is exactly why I bet on founders. Founders who are like Buddy. Those who don’t let conventional wisdom sway their ability to dream. Those who don’t let titles and labels parameterize their ability to act on dreams.

I, admittedly, don’t follow hockey closely. And some of the jargon in Zevon’s song, I had to do a double take with my mentor and Google. But I can’t help but appreciate the clever choice of words as well as the emotional impact in the lyrics. Which makes sense for Hit Somebody! and Warren Zevon to have a cult following in the international hockey community.

Photo by Aliane Schwartzhaupt 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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The Four Traits of World-Class Startup Founders

Proportionally speaking, I rarely make referrals and intros. Numerically speaking, I set up more intros than the average person. Frankly, if I made every intro that people have asked of me, I’d be out of social capital. It’s not to say I’m never willing to spend or risk my social capital. And I do so more frequently than most people might find comfortable. In fact, the baseline requirement for my job is to be able to put my neck on the line for the startups I’m recommending. The other side of the coin is that I’ve made more than a few poor calls in my career so far. That is to say, I’m not perfect.

I only set up intros if I can see a win-win scenario. A win for the person who wants to get introduced. And a win for the person they will be introduced to. The clearer I can see it, the easier the intro is to make. The less I can, the more I look for proxies of what could be one.

This largely has been my framework for introducing founders to investors, as well as potential hires, partners, and clients. Over the years, I realized that I’ve also been using the same for people who would like an intro to someone above their weight class.

Below I’ll share the 4 traits – not mutually exclusive – of what I look for in world-class founders.

  1. Insatiable curiosity
  2. Bias to action
  3. Empathy
  4. Promise fulfillment
Continue reading “The Four Traits of World-Class Startup Founders”
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The Frequency of the 3 Types of Mentors

I wrote an essay about the three types of mentors exactly a year ago. Peer. Tactical. Strategic.

  • Peer mentor – Someone who has a similar level of experience as you do in a given field.
  • Tactical mentor – Someone who is 2-5 years ahead in experience, and someone who can check your blind side. Because they have gone through similar situations as you are currently going through not too long ago, they can provide context as to the variables (core and confounding) involved.
  • Strategic mentor (which I formerly called veteran mentor) – Someone who has attained success in a particular field as you would define it. While they won’t be able to help you in the play-by-play, they can provide the bigger picture – the macroscopic view. Assessing and reassessing your long-term goals – your true north.

Rocks, pebbles, sand

Many of you might be no stranger to the rocks, pebbles, sand analogy. As the metaphor goes, if your life were a jar, you’d want to fill it with rocks first, then pebbles, then sand. If you start off filling your life with sand, you will have no more space for rocks and pebbles. Similarly, if you start filling it with pebbles, you will only have space left for sand, but not rocks. Analogized, rocks are your life and career’s most important projects and milestones. Pebbles are the smaller projects that lend itself to the whole, some of which you could do without. Sand represents the day-to-day, week-to-week ups and downs.

Rocks

Strategic mentors are most useful once a year (or at best 2-3 times/year) to see if you’re aligned with your goals. They help you set the large milestones you want to accomplish in your life.

  • What matters?
  • What doesn’t?

Pebbles

Tactical mentors, you seek after you come up with a few solutions/hypotheses that you would like to test. You don’t seek them as often, but they can help provide context to what you’re going through now, largely from their own experience having gone through it recently.

  • What variables am I overlooking or underestimating their effects on the outcome? Or simply put, what could go wrong?

Sand

You seek peer mentors before you come up with your solution and in problem-solving mode. These are the mentors you’re going to be spending the most time with. And most likely, the most abundant category of your mentors.

  • How would you attempt to resolve this dilemma? What would you do if you were in my shoes?
  • What are new, innovative ways I can use to tackle this problem?

While they vary in their sizes, each rock, pebble and sand is necessary to live your most fulfilling life.

In closing

Over the years, I’ve had the great fortune of having some amazing mentors and mentor figures that have shone me the proverbial light when alone, I may have struggled to find. Yet equally so, I’ve met their antithesis. Luckily very few, but nevertheless. People who don the mantle of being a mentor, but cannot tolerate your success when you surpass them. The latter I met years ago when I indiscriminately and naively sought out mentors, for the pure sake of just having “mentors”. Arguably, as a foolhardy contest of ego and pride, specifically to compensate my feelings of ineptitude.

A mentor like a friend is someone who is happier and wishes for your success than sometimes you do for yourself. Often, independent of their own escape velocity. Simply put, they invest in your success. And of course with that pretext, they are a scarcity. Even of those are willing and free enough to be mentors, given the volume of their inbound, understandably, their response rate is exceedingly low.

While that fact shouldn’t deter you from seeking mentorship, it makes me cherish the time, effort, and advice I have been fortunate enough to receive.

In the words of Tom Landry, legendary head coach of the Dallas Cowboys, “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.”

Photo by Anas Belmadani on Unsplash

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2020 Year in Review

I’ve written 102 essays on this blog in the past year, plus some change, spending an average of 1-2 hours per piece and a range from 30 minutes to 2 weeks. An average of 1,200 words per post. While not mutually exclusive, over half of which were on startup topics. One in three described the venture capital landscape. 36 (excluding #0) #unfiltered blog posts, where I share my raw, unfiltered thoughts about anything and everything. 16 on mental health. A surprising 13 on cold emails and its respective ecosystem. And my first public book review. Some didn’t age well, like The Marketplace of Startups. Some will stay evergreen.

25% of my blog posts I started writing at least 48 hours before the publish date. 1 in every 3 (-ish) of the afore-mentioned, I rewrote because I didn’t like the flow. For every 2 essays I wrote, 1 of which I had to wrestle deeply with the thought of imperfection. In effect, half of my essays were a practice to overcome my own mental stigma of “writer’s block.” Yet after over a year of writing, I realize that I’ve become prouder of my writing than when I started.

So, as the year is transitioning into the next, I thought I’d take some time to reflect on my growth 100 (+2) posts after starting this blog. Let’s call them superlatives.

Top 10 most popular

Ranked by total views per post, the 10 posts readers visit the most.

  1. #unfiltered #30 Inspiration and Frustration – The Honest Answers From Some of the Most Resilient People Going through a World of Uncertainty – I asked 31 people I deeply respect to share some of their greatest drivers and darkest moments in life and how they got through them. You can find part 2 here with 10 more thoughts.
  2. My Cold Email “Template” – My friends have asked me for years what I write in my cold emails, and now, what and how I write my cold outreaches are available for your toolkit.
  3. Fantastic Unicorns and Where to Find Them – An essay on the parameters and the mental models investors use to find “unicorn” startup ideas.
  4. When Investor Goodwill Backfires – What It Means to be Founder-Friendly and Founder-Investor Fit – How founders can do investor diligence before signing the term sheet and also how to best manage founder-investor dynamics
  5. #unfiltered #24 How long do you take to prepare for a talk? – A Study about Time Allocation
  6. How to Build Fast and Not Break (As Many) Things – A Startup GTM Playbook
  7. 10 Letters of Thanks to 10 People who Changed my Life – Every holiday season I write thank you letters to the people I deeply respect. It’s one of the best times of the year to reconnect. These are the letters I wrote in 2019. Here are also some I wrote this year for more context.
  8. #unfiltered #18 Naivety vs Curiosity – Asking Questions, How to Preface ‘Dumb’ Questions, Tactics from People Smarter than Me, The Questions during Founder-Investor Pitch
  9. #unfiltered #11 What I Learned About Building Communities through Social Experiments – Touching Jellyfish, Types of Social Experiments, The Thesis, Psychological Safety and Fairness
  10. The Marketplace of Startups – While many of the remarks on this blog post are now obsolete, largely incited by the 2020 Black Swan event – COVID, the two questions at the end of the blog post are the two I still like to ask founders today.

Personal favorites

While not every one of these got the limelight I had hoped, each of these are ones I felt great pride in being able to write on.

Most challenging to write

I had been wrestling with how vulnerable I can allow myself to be in the public space. Writing this post was frightening, but I’m glad I did. It cascaded into deeper conversations with my friends, colleagues and readers, but also inspired more blog posts after this about mental health.

#unfiltered #26 Am I At My Best Right Now?

In closing

I first started this blog with the intention of chronicling my own learnings in the amazing world of venture. While I couldn’t guarantee it would be helpful to every individual reading my humble meandering, I could, at least, guarantee what I write has been or continues to be instructive for me.

Within the first month it had evolved into an FAQ and a means to provide value to as many founders as I can when one day the number of people I want to help exceed my available bandwidth. Wishful thinking at the time, but a cause that inspired me forward. After the first six months, with the introduction of the #unfiltered series, I began to write to think – a way to flush out simple, unrefined ideas to more robust concepts. While I’ll forever be a work in progress, I began to make new dendrite connections that never existed before. In a way, I was and am still chronicling my own journey in hopes that it will continue to guide people beyond my immediate sphere of influence.

Thank you, each and every one of you, for accompanying me on this journey we took yesterday and the one we’ll take tomorrow. And I hope this cognitive passport will continue to serve as your cup o’ Zhou (/joe/) weekly.

Cheers, and I’m excited for the adventure ahead!

Photo by Ray Hennessy on Unsplash

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How Do We Welcome the Founder Narratives Behind the Curtains

Being a founder is one of the toughest jobs in the world. Resilience and grit are two (or one) of the indispensable traits of a 5-star entrepreneur. And most, if not all, investors establish grit as the baseline in founder selection, as opposed to the topline in various other careers. While I don’t mean to discount other career paths, all of which I have incredible admiration for, I can only speak in the world of venture where I spend most of my time in.

Yet that same persistence could very much be the same double-edged sword that makes or breaks you. In October, Ryan Caldbeck wrote about his decision to step down as CEO of CircleUp. It was and is one of the most candid pieces I’ve read about the founder journey to date. In it, one section particularly stood out. “Persistence was my superpower. But now I’ve now come to understand that persistence is a double-edged sword, and my decision not to take a break, to not take more off my plate, hurt me, my family and the company. That was the biggest mistake of my career.”

In the founder journey, there exist many moments a founder’s resilience is stress-tested. To get their first customer. To scale to a team of 10. 30. 100. To get their first investor. To raise their first institutional round. But the last thing a founding team needs is for some of their greatest evangelists – their investors – to create counterproductive friction. While it’s presumptuous of me to say that all friction is counterproductive, some friction and additional perspective is necessary to help founders make better, more informed decisions.

In his same essay, Ryan shares a feedback email he wrote to his former board member, as that member’s participation in the company had become “counterproductive”, “vindictive”, and even “destructive”. Unfortunately, these stories happen more often than I would like. It is why many founders believe investors are the gatekeepers to their startup’s success. But we’re not. We don’t have the right to be. On the same token, that’s exactly why it’s so important for founders to deeply consider founder-investor fit.

Michael Freeman found in 2017 that entrepreneurs are 50% more likely to report a mental health condition. Being a founder is lonely. But it doesn’t have to be.

Anton Ego’s words

A few weekends back, my friend and I re-watched my favorite movie. And as the movie faded into music, Anton Ego’s words echoed in my head. While it’s not the first time this quote has appeared in the venture world, it certainly won’t be the last:

“In many ways, the work of a critic is easy. We risk very little, yet enjoy a position over those who offer up their work and their selves to our judgment. We thrive on negative criticism, which is fun to write and to read. But the bitter truth we critics must face is that, in the grand scheme of things, the average piece of junk is probably more meaningful than our criticism designating it so. But there are times when a critic truly risks something, and that is in the discovery and defense of the new. The world is often unkind to new talent, new creations. The new needs friends.

“Last night, I experienced something new, an extra-ordinary meal from a singularly unexpected source. To say that both the meal and its maker have challenged my preconceptions about fine cooking is a gross understatement. They have rocked me to my core. In the past, I have made no secret of my disdain for Chef Gusteau’s famous motto: ‘Anyone can cook.’ But I realize, only now do I truly understand what he meant. Not everyone can become a great artist, but a great artist can come from anywhere. It is difficult to imagine more humble origins than those of the genius now cooking at Gusteau’s, who is, in this critic’s opinion, nothing less than the finest chef in France. I will be returning to Gusteau’s soon, hungry for more.”

For VCs

One of my favorite investors often says, “stay positive, test negative.” While the greatest strength an entrepreneur can have may be grit, the greatest strength an investor can have is optimism.

Optimism in the world. In markets. In startups. But especially people. That even if one venture doesn’t work out, for the people I’ve had the opportunity to stand behind, I know one of their pursuits eventually will. It’s only a matter of time and luck.

That same optimism is a leading indicator for open-mindedness. As people who build our careers at the top of the funnel, it is our obligation to cast our net outside of what is most familiar to us. There will be a number of ideas and belief systems entrepreneurs have that challenge our own. And in many ways they should, as founders are on the frontlines of innovation, they are aiming to be “right on the non-consensus“, to quote Andy Rachleff. When I first got into VC, that same investor who said “stay positive, test negative”, shared another word of advice, “Some of the best ideas seem crazy at first.“

George Bernard Shaw once said something similar as well, “The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore, all progress depends on the unreasonable man.”

Optimism isn’t only isolated to ideas, but also to the people – the “unreasonable” women and men – behind those ideas and the decisions they make. These innovators aren’t perfect, yet somehow many of us expect them to be. And that dichotomy has created this unfair dynamic that stunts innovation more than we think. I have so much respect for the funds that have set aside capital to invest in founders’ wellbeing, like Felicis Ventures, Freestyle, Crosscut, and more. And I hope many more will follow.

The stories we tell

Over the past few months, I’ve had a number of conversations with founders, friends, and readers about “mental fitness” and “emotional hygiene”. If I could borrow two of my friends’ vernacular. And I’ve learned that we humans are such amazing storytellers.

These powerful narratives has kept the human race alive all these millennia. Before the written word, it was the art of the spoken word, passed down from generation to generation, that held tales of ancestral origins of where to hunt and where to migrate to each season. The same stories have started and ended wars. They have helped us conquer impossible odds. Some narratives today are compelling enough for us to buy a new product or to end a conglomerate.

Yet these exact stories, especially the ones we tell ourselves, can cause stress, anxiety, and depression. The ones that the people we care about and respect tell us can carry even more weight. From role models, parents, managers, friends, mentors, teachers, peers, and more.

In closing

I realized, in conversation, these past few autumn months, more than ever, the power of sharing those stories. To share that we’re not alone and that together, we may learn more than the sum of our individual parts. I understand that it’s no easy task. Even for myself, I debated for the longest time whether to share that I’m not at my best right now. But I’m glad I did. The feedback from the people around me I’ve gotten since brought forth clarity and solace. Similarly, six of my friends, who publicly shared how they get through their toughest times (Pt 1, Pt 2), told me after how grateful they were to have an enormous weight lifted off their shoulders.

Top photo by Nong Vang on Unsplash

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#unfiltered #36 Thanksgiving Letters and Holiday Season Thank You’s

Every year, on Thanksgiving, I write a series of emails, letters, and texts to thank the individuals who have helped me become the person I am today – wittingly and unwittingly. Some of whom I may have never met. Some I may never meet again. And a small handful I will meet again on the other side. Nevertheless, the future likelihood our paths crossing does not change the gratitude I have toward each person.

Over time, largely due to the volume of letters I write, this practice has bled into the days between Thanksgiving and Christmas. Last Thanksgiving, I published 10 of the above letters (anonymized) I wrote that year as inspiration for friends, colleagues, and readers who may have been considering or writing their own. This year, I assume, won’t be an exception. And for many others who might need a gentle nudge forward, I share two letters of mine I’ve written this holiday so far to act as a potential anchor for you to start yours.

Dear…

  1. Centaurus – A reminder of self worth
  2. Cassiopeia – A chain reaction

A reminder of self worth

Dear Centaurus,

This year has been incredibly bizarre. On one hand, I’ve had some of my biggest wins in my life so far. On the other, I’ve hit low points I never thought were possible – at least for myself. Actually, especially so for myself. Yet they happened.

While many others might have seen them come and go like the autumn breeze that is blowing against my window sill as I am writing to you, you were there for me in some of my darkest times. I don’t know if it was telepathy or clairvoyance, but earlier this month you sent me one text: “Love you man. Just because.” It came less than 24 hours after a streak of 3 founders independently telling me I was not worth their time. One of which, the call ended 15 minutes into a 30-minute call. That morning I really needed that. And in that moment, I was reminded of another line you sent me last month when I asked you for a favor:

“Beautiful things don’t ask for attention.”

Thank you. I wish you and your family the warmest, the coziest, and the best of holidays. I believe the Danish call it “hyggelig.”

My deepest gratitude,

David

A chain reaction

Dear Cassiopeia,

I still remember the day I selfishly reached out to you. My internal monologue went something along the lines of: “Nah, she’s going to be way too busy to reply. But you know, what if? Nah! Maybe I should send a follow-up in a week.” 7 minutes later, my phone goes bzzzt, bzzzt. Being the phone addict that I am, I had to check and there in my inbox lied an email from you. Overly excited, I replied quickly. And your following reply, or more accurately, your voice message lit my day up like New Years.

I’m 24-years young, but sometimes, like that day, I still act like a 7-years young. At times, my friends and family tell me I should act my age. But in those moments, I admittedly unforgivably don’t.

Since then, you’ve inspired me to write a post about the psychology of curiosity and reach out to professors, like John List, to write posts like this. A chain reaction of ideas, but more importantly, your advice and feedback emboldened me to reach further. In this world that snowballed from your reply to my selfish message, 1+1 = 3.

Thank you. I wish you and your family the warmest, the coziest, and the best of holidays. I believe the Danish call it “hyggelig.”

My deepest gratitude,

David

In closing

We don’t often thank the people who’ve helped us get to where we are today often enough. I know I, for one, don’t. Thankfully, every year, despite everything else that is going on in my life and in the world, I’m reminded to set time aside to show my appreciation. A few minutes per person for me is asking very little for people who have saved me days, weeks, if not years worth of mistakes and folly.

And, the holiday season also happens to be one of the best, if not the best time to reignite old flames and to spark new ones.

Photo by Johannes Plenio on Unsplash

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

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

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#unfiltered #35 How Do You Know When You Click?

Over the weekend, my friend and I had this fascinating conversation about how we found our other friends. I know, metaphysical, nerdy even. But nevertheless, I thoroughly enjoyed it. She posed the question: “Is it just based on how long you’ve known each other? And how often you see each other?” For most of my life, I would have said yes. Classmates that became friends were people I met and could chat with over lunch or after school. The same is true for colleagues. And strangers. Some happened exceedingly fast – within 24 hours. Others have taken over half a year before we “warmed up” to each other.

Unsurprisingly, it gave birth to the question: At what point does an acquaintance become a friend?

The PMF parallel

To be honest, I didn’t have a good answer then, nor do I have one now. Part of the reason I’m sharing this is to open up dialogue and draw inspiration from you, my readers.

Pushing up my glasses, which I’ve got to get a new pair (open to any recommendations), I couldn’t but analogize it to startups finding product-market fit.

How do founders know when they hit product-market fit? The TL;DR version: when you’re too busy to even ponder if you have product-market fit. Or simply, you’ll know it when you have it. For the longer, less nebulous answer, I recommend checking out Lenny Rachitsky’s piece on it, and some of other essays I’ve written on the topic:

Or as Casey Winters, Chief Product Officer at Eventbrite, says:

“Product-market fit isn’t when your customers stop complaining, it’s when they stop leaving.”

Some more examples include, when:

  • You’re focused on upgrading your servers rather than acquiring customers.
  • There’s so much demand, you’re writing “I’m sorry” and “Not yet” emails to your customers who are asking when can they get off the waitlist.
  • Laggards on the adoption curve start using your product and saying wow. In Airbnb’s case, that was Joe Gebbia‘s mom using the product.
  • There are handwritten love letters in your office mailbox.
  • Customers are asking how they can pay (more) for your product.
  • You’re feeling the pull of the market rather than pushing your product in front of people.

Friends

On a similar note, when the entropy of a relationship and the subsequent conversations break into an impetuous nature that eclipses the inciting reason for the relationship, you might have something going. Or in simpler words, you can’t stop the momentum of the relationship. “What about this?” “Let’s do that!” “Ahhh, not enough time!” Of course, as all relationships go, it takes two to tango. Just like product-market fit, when you don’t have it, it’s not obvious what you need to do make it click. But when you do have person-person fit, everything makes sense. And quite obvious, in retrospect.

While the above was my answer on Sunday, I’m not completely sold it’s the end all, be all. And as I continue to find new sparks and rekindle old flames, I’m sure I will learn more about myself and others. A provocative question that may require a more provocative answer.

Top photo by Tyler Nix on Unsplash

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

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

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