Month: November 2020

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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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When Investor Goodwill Backfires – What It Means to be Founder-Friendly and Founder-Investor Fit

A few Fridays ago, I had the fortune of reconnecting with a founder, backed by some of the most recognizable names in the Valley and exited his business last year to a juggernaut in the data space. Now working on his second startup. And he brought something extremely curious to my attention. “Investors shouldn’t be too founder-friendly.”

I’ve talked to hundreds of founders and seen thousands of pitch decks in my short 4 years in venture capital. Yet, that Friday was the first time I’d ever heard that. And it was too bizarre for me not to double-click on. The fact that the sentence also came out of a founder’s mouth and not an investor’s bewildered me even more.

Continue reading “When Investor Goodwill Backfires – What It Means to be Founder-Friendly and Founder-Investor Fit”
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#unfiltered #34 The Impetus to Cup of Zhou

It was a warm autumn 7pm. The golden ball had just found its home beyond the rolling hills of San Francisco. The sky above, dyed violet melting into a soft pink. I was walking up to Liholiho Yacht Club. According to my pal, the best spot in town for Hawaiian food. A 7:30 reservation for our quarterly mentor-mentee dinner.

As I was walking up from SOMA, I was running through the conversation I just had with a founder. He closed the conversation off with: “You should really share this advice publicly.” He was right. ‘Cause in my 3 years in venture capital, I’ve shared that same piece of advice I gave him more than 50 times at that point. I’d been meaning to. I had 11 blog posts written already, just not published. All written in an FAQ format. Yet, the only thing I was still wrestling with was the name of the blog.

It seems trivial in the grander scheme of things. But the perfectionist, inspired by my younger career in art, kept nagging me.

Reality on Ice (ROI). Nah, that wasn’t it. Sounds like a Disney ice show.

Irrogueular. Nah, too eccentric.

David’s blog. Mhmm, talk about uninspired.

Curiosity. Oooh, I like this one, but (1) it’s taken, and (2) doesn’t feel deep enough.

And 80 more where those came from. But none clicked.

Anxious, once again, I began ideating as I bobbed and weaved between the evening crowds. Yet to no avail by the time I reached Liholiho.

Dinner was great as per the usual. My mentor had just joined a new startup, leading a new initiative. We talked work. Life. Athletic endeavors. Romance. And of course, food. It came to no surprise when we two hungry bears needed more to satiate our appetite despite a wonderful meal. After we were “Yelping” places to go to, which we probably flipped through a dozen or two, we gave up.

“David, let’s just grab a cup o’ Joe, and call it a night. Wanna go to-“

“Wait. That’s it!”

“What’s ‘it’?”

“Coffee.”

“That’s what I said.”

“No, no, no… for my blog. The name. My job is to grab coffee with folks. And at the same time, just like caffeine kickstarting all of our days, hopefully my blog can help founders kickstart their startup.”

I ended up scrapping 10 of my 11 blog posts. The only one I kept was my thesis. And I started anew. I spent 3 months ideating a name. 3 years, if you count all the random other WordPress blogs I started. But all it took for me was a moment – a spark. The closest thing I could analogize, at that point, to gut feeling.

Afterword

Oddly enough, this past week, three people independently asked me why this blog is called Cup of Zhou. One pronounced it “cup of zow” (like cow). Another pronounced it “cup of zoo”. The last was over text. I don’t blame them. They’re not the first, and they’re definitely not the last. I respond to them all. They’re all part of my American-born Chinese identity’s memoir. And this blog is just another chapter in my memoir.

Cup of Zhou. /cup uh Joe/

Photo by Demi DeHerrera 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 #33 Inspiration and Frustration Pt. 2 – What Drives Some of the Most Resilient People Forward

A few weeks ago, I published Part 1 of this post on inspiration and frustration. In that time, its reception has been uplifting. Easily my most popular and well-received blog post to date. It also happens to be one of my favorite posts to have published so far. So, I thought I’d continue to ask people about their cocktail of emotions now, the below two questions:

  1. What is the one thing that inspires you so much that it makes everything else in life much easier to bear?
  2. What is stressing/frustrating you so much right now that it seems to invalidate everything else you’re doing?

But, each person can only choose one of the above two questions to answer.

Three of the below candid responses are people I asked from the first cohort, while the other eight are people I thought would add a new degree of freedom on perspective. All of which were drawn more to their inspiration than their frustration.

And as such…

  1. It takes a lot of things to inspire and motivate… rather than one individual thing. – Model, writer, founder
  2. I’m inspired to have a hand in making the world better for everyone through technological progress! – Venture capitalist
  3. I’ve made friends with a girl from my neighborhood grocery store and a stranger opened a door wide for me so I could run towards the train and not miss it. – Founding partner/CEO, investor, community manager
  4. When you start to understand that life is bigger than just you and me, there’s a shift in perspective that brings meaning and purpose to our lives. – Zynara Ng, public speaking coach, video producer, TED speaker
  5. We have the means to weather our current circumstances. – Business professor, consultant
  6. We have struggled to find an extremely valuable and painful problem to start with. Nevertheless, someone will figure it out. Why not me? – Startup founder
  7. We just got a new addition to our family. […] I look forward to future conversations about life and deep topics with him, just like this one! – Startup founder, podcast host
  8. We just tend to judge ourselves more harshly because we have our entire past and lived traumas that we judge ourselves by. – Senior policy aide
  9. Their thank you letters, pictures, and stories of how Vinder has changed or saved their business/life solidifies to me that I’m on the right path. – Sam Lillie, startup founder, hiker
  10. Since this goal is so long term and grand, it’s easy to realize that small things don’t matter. – Sohum Thakkar, engineer
  11. In a world that falls short of showing us unconditional love, I can live my life in such a way that I can be that source of acceptance that others need. – Engineer, writer
Continue reading “#unfiltered #33 Inspiration and Frustration Pt. 2 – What Drives Some of the Most Resilient People Forward”
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#unfiltered #32 How to Win Even When You Lose

Two and a half weeks ago, I wrote about my mental model for confronting fear – the art of running into walls. Inevitably, I’ve had more conversations about fears and how to overcome them since then. And in those moments, I was reminded of a question Seth Godin posed on his recent appearance on The Tim Ferriss Show. Most people ask the question: “What would you do if you could not fail?” And subsequent answers led to wild dreams, achieving the impossible, and often times, still not a step closer to achieving that dream, myself included. I wanted to be an astronaut, a pilot, an Olympic medalist, and more. Instead, Seth posed the counter: “What would you do if you knew you would fail?“

Knowing that I’d fail

Seth cites that most marathoners competing in the Boston Marathon do not aim to win, yet they still do it. Similarly, I work with founders knowing that most will fall short of their dreams. If we’re talking about expected value – the sum of all the dollar size outcomes of each possibility, multiplied with their respective probability of occurring, then:

E(Vstartup success) << E(Vmost other career paths)

Rationally speaking, the career of a founder is not designed for success. But hell, it’s the irrational founders who do find it. Against impossible odds.

But why?

Why still pursue a career when the odds aren’t ever stacked in your favor?

On the same token, why participate in any contest if you know you’re most likely going to fail? And, I mean contest in the most liberal sense here. Just like a marathon is a contest of endurance and physical prowess, building a startup is a contest of capital, time, and social impact. Confessing to your crush is a contest of love. Sending a cold email is a contest of attention. The more saturated the market – the contest – the more likely you are to fail.

How to Win

In winning, I focus on only one question: What will I gain in this pursuit that’s independent of the result of the contest?

Running a marathon proves that I can push my body beyond its limits.

Confessing to my crush gives me resolution to move on in my life.

Sending a cold email hones my communication and research skills.

I work with startups to build friendships and acquire skills that will transcend the dollar value of the venture. People who are ambitious typically learn fast, and will try again and again until something works. If not this idea, then the next. If not today, then tomorrow. And, if not tomorrow, then the day after. It’ll only be a matter of time before preparation meets opportunity. It’s why we call startups 10-year overnight successes.

So when I take on a new endeavor even outside the exciting world of venture, I look for where there will be a net positive in my life and the world around me, on 3 fronts:

  1. The relationships/friendships I will build along the way,
  2. The skillset I will develop and/or hone,
  3. And the impact the process will have in the lives of other people, particularly my friends and family.

If the above function has a positive first and second derivative, then I know I will win even if I lose.

Photo by Johann Walter Bantz 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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How Entrepreneurship and Networking Are Synonymous With Each Other

A few days ago, I came across a question on Quora that sparked my interest. “What [is] the best network for developing entrepreneurship skills?” And I couldn’t help but backcast, as Mike Maples Jr. at Floodgate would call it, which I shared a bit more here. Looking at the entrepreneurs I know who have achieved some modicum of success, how did they build their entrepreneurial skills?

Taking it a bit further, what is one skill that they have that made all their other skills much easier to acquire and/or hone? And I could only come up with one answer, which is understood in various nominations. Resourcefulness. Scrappiness. Creativity under pressure. Staying lean. Frankly, their ability to hustle.

“The best network”

What is the best network for developing entrepreneurial skills?

The simple answer: One you build yourself.

The longer answer…

Entrepreneurship is a career that requires you to hustle. Likewise, a network you build yourself from reaching out and cold emailing has the potential to be stronger than even the best of networks out there. But entrepreneurship can come in two flavors: a hobby and a lifestyle.

A hobby or a lifestyle?

If entrepreneurship is a hobby, there are amazing collaborative:

  • Slack groups,
  • Subreddits,
  • Facebook groups,
  • Quora spaces,
  • Meetup groups,
  • Conferences/trade shows/expos,
  • You name it, it’s out there.

But it will be akin to sitting in a classroom and learning the theory and conceptualizations.

If entrepreneurship is a lifestyle, you need to learn by application. And unfortunately, you’ll need to develop scar tissue from making real mistakes outside the classroom. You need to hustle and find what works and doesn’t work for you. Two of my favorite venture firms, 1517 Fund and Hustle Fund, invest in founders who do exactly that. Unlike many other venture funds, it’s in their thesis. Learn by doing. Learn by hustling. While there is merit in literature and academic institutions, you are learning at the pace of the system. And when you’re a founder, often times, time is not on your side.

In a parallel, an entrepreneur once described the bifurcation as a “lean-back” versus a “lean-in” activity. A “lean-back” activity would be watching a sitcom, picking strawberries, or typing a simple response to an email chain. Whereas a “lean-in” would be playing football, playing a competitive first-person shooter game, or fixing a bug in the code 2 hours before a product launch. Entrepreneurship, as you might guess, is a “lean-in” sport. So is networking.

There are two French words I often allude to – savoir and connaître. Both mean to understand. Savoir means to understand on a superficial, factual level. Connaître means to know on a deeper, emotional level – to be deeply familiar with. As an entrepreneur, the lifestyle you choose is often not passive, but an active one, or some might argue, an aggressive one. One where the clock started ticking before you started. Sometimes, before you were even born. Ben Horowitz makes a brilliant comparison between a peacetime and a wartime CEO. From his piece, I’ll quote two of his juxtapositions:

“Peacetime CEO knows that proper protocol leads to winning. Wartime CEO violates protocol in order to win.”

“Peacetime CEO has rules like ‘we’re going to exit all businesses where we’re not number 1 or 2.’  Wartime CEO often has no businesses that are number 1 or 2 and therefore does not have the luxury of following that rule.”

Where you’re required to make decisions in difficult times, and if you don’t understand a concept or a skill to the level where it’s engrained in your bone, you will fumble more often than you run touchdowns. Part of the reason why second-time, third-time entrepreneurs usually perform better than first-time entrepreneurs.

I graduated from a stellar university, UC Berkeley, located at one of the epicenters of Silicon Valley/Bay Area, where I got my economics degree and a certification in entrepreneurship and technology. I took a number of classes that allowed me “to learn and hone” my entrepreneurship skills. While there were a handful, I came out feeling I was equipped with the knowledge to take on the world. When I put them to the test, I realized I knew nothing. When faced with reality, I didn’t know how to deal with edge cases since edge cases are rarely taught in the classroom.

Most communities and classes teach entrepreneurship skills in abstractions, making it easier to understand. Even this blog post is, in many ways, an abstraction. They rarely teach the edge cases ’cause frankly, there are too many “what if’s”. But as an entrepreneur, you need to be ready for the “what if’s”. For anything and everything. And over time, what transcends the individual skills you have is having a mental model to hedge yourself from future edge cases.

I once asked someone what being an expert meant. And I really liked his answer, as it stuck with me all these years. He said, “An expert is someone who has made all the mistakes in a very narrow field.”

Photo by Jed Villejo 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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How to Build Fast and Not Break (As Many) Things – A Startup GTM Playbook

The tech world, particularly Silicon Valley, in the past 2 decades, has accelerated its growth ’cause of one mantra: “Move fast and break things.” Some of the most valuable products we know today were built because of that. Facebook, whose founder coined the phrase. Google. Amazon. LinkedIn. Uber. The list goes on. In sum, be “agile”. Simultaneously, I see founders, on the regular, take this mental model too far. They move fast, but they rarely give enough time to test their hypotheses.

Equally so, some companies cannot afford to “break things”. Take Dropbox, for example. Ruchi Sanghvi, founder of the South Park Commons Fund, former VP of Operations at Dropbox, and Facebook’s earliest female engineer, told VentureBeat in 2015, “Quality is really, really important to Dropbox, and as a result we needed to move slower — not slowly, but slower than Facebook.” Ruth Reader, who wrote for VentureBeat at the time, further extrapolated, “What was right for Facebook — fast-paced iteration and fixing bugs in real time — didn’t work for DropBox, an application people entrusted with personal documents like wedding photos or the first draft of a novel. What was valuable to DropBox was the details.”

On the other extreme, there are founders who spend day after day, week after week, and sometimes year after year, pursuing the “perfect” product before launching. If they were right on the money before, by the time they launch 6 months later, they might be 6 months off the money. Take the situation we’re all in today for example – the pandemic. No one could have predicted it. In fact, I had many a few predictions before the pandemic, which all proved to be unfortunately wrong.

  • The Marketplace of Startups, written on February 24, 2020 – I alluded to an opinion I held that consumer social was almost dead. The consumer app market had become so saturated that it was hard for new players to play in.
  • Myths around Startups and Business Ideas, written on October 12, 2020 – Pre-COVID, I was more bullish on Slack than Zoom as a public stock investment. History proved otherwise.

… and more to come. Mistakes are inevitable. And “the rear view mirror is always clearer than the windshield”, as Warren Buffett would describe. Seth Godin said in his recent interview on The Tim Ferriss Show: “Reassurance is futile because you never have enough of it.”

At the end of the day, as a startup founder, your raison d’être is creating value in the world where there wasn’t before. As Bill Gates puts it: “A platform is when the economic value of everybody that uses it, exceeds the value of the company that creates it.” Analogized, your startup is that platform.

So, in this post, using the lessons from other subject-matter experts (SMEs), I’ll share how startup teams can balance speed with intentionality in their go-to-market (GTM) strategy.

Continue reading “How to Build Fast and Not Break (As Many) Things – A Startup GTM Playbook”
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