Category: Life

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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.

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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.

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An Innovator’s Inspiration

Photo by Skye Studios on Unsplash

Creativity.

I have a love-hate relationship with that word. On one hand, I love and seek to learn from creative souls. It’s a trait that I seriously respect in individuals, regardless of industry, profession, or background. On the other hand, it’s rather amorphous. What’s creative to me may not be creative to you. We are bounded by the parameters of our experiences and what we, as individuals, are exposed to.

So, where do innovators draw inspiration?

Over the years, I’ve seen inspiration stem from three main frameworks:

  • The flow from art;
  • Margins;
  • And, what people dislike.

The Flow from Art

I seem to find that the data largely (with a few outliers) points towards the following:

Art precedes science. Science precedes tech. Tech precedes business. Business precedes law.

Art is bounded only by one’s imagination. Science, which draws inspiration from art, is limited by our physical universe and the fundamental laws. And, tech rides on the coattails of science, restricted by the patterns recognized in our universe by scientists before them. Similarly, business can only optimize existing technology. Following suit, regulations and legal practice can only debate and prevent ramifications that have turned from hypothesis to reality.

On one end of the spectrum, fiction has driven innovation on the fundamental, scientific front. Scientists have tried to make the impossible – fiction, superstition, assumptions, and imagination – possible. On the other end, the legal and regulatory space has empirically lagged behind business innovation. From autonomous driving to the shared economy to video games, a regulatory emphasis came only after incidents occurred. I’m a huge proponent of founders becoming self-regulatory. But that is a discussion for another day.

Margins

As Jeff Bezos famously said:

“Your margin is my opportunity.”

In the lens of a businessperson, profits exist on the margins. In a fully saturated market, as we learned in economics class, perfect competition will squeeze out profits. That margin can be delta between human perfection and imperfection. It can be the difference between a naive and sophisticated individual. It can also be the blind spots between a self-awareness and ignorance.

The good news (and bad news?) is that humans aren’t rational. As much as we try to be, we’re not. We repeat the same mistakes. After all, that’s where our favorite stories come from – the fact that we’re imperfect. If we were rational, our friendly neighborhood kid from Queens wouldn’t have to struggle with identity. Or, Skinner, the head chef at Auguste Gusteau’s restaurant, wouldn’t be out to exterminate my favorite rat chef.

From a nonfictional front, if we were rational, gambling, the lottery, therapy, and more wouldn’t exist. In fact, there’s a whole industry that capitalizes on human imperfection – insurance. We choose to reach for that last cookie when we know a healthier diet with less sugar is better for us (I’m guilty as well). We set New Year’s resolutions to work out more, but regress to our couch norm after the first month. Walter Mischel famously conducted The Marshmallow Experiment. When given the option to wait 15 minutes to double their treats, many children opted for immediate gratification.

There would be way fewer founders if they were rational. I mean, come on, the numbers work against them. 90% of startups fail. So, from a VC’s perspective, we have to ask ourselves:

What’s is the underlying notion that makes this product work?

What is that innate theme in human or societal development that won’t disappear anytime soon? What factors produce such a trend? And what margin is it taking advantage of? Uber was made possible with the evolution of smartphone and faster data. As more data were archived online, Google became a reality because of the internet and browser. Two current examples of underlying notions include:

  • Audio, including, but not limited to, podcasts and audiobooks, is the new form of content consumption. Not only does it free up consumers’ hands and eyes up, audio content is often easier to digest. The spoken word has been around millennia, whereas print is fairly new invention. Emotions and sarcasm is often easier to relay via audio than via print. So, what else is possible?
  • With growing consumer sentiment against traditional social media, like Facebook, Twitter, and Instagram, there is a shift to social experiences surrounding active participation. Sarah Tavel writes a great piece on this. Examples include Discord, Medium, TikTok, and user-generated content (UGC) in video games, like mods and in-game skins. Many of the traditional social media platforms leave users with a more negative passive experience, where they feel a sense of FOMO (fear of missing out). Through active participation, users can be a part of the conversation, rather than watch from the sidelines.

What do you dislike?

Speaking of negative experiences, aversion is a strong motivating emotion humans have. Like prospect theory illustrates, loss invokes a stronger response than gains. It also happens to be one of the reasons why I probe how obsessed a founder is about a certain problem.

In a recent interview with Andrew “Kappy” Kaplan, host of the podcast, Beyond the Plate, Grant Achatz, legendary chef, talks briefly about how he drew inspiration from his daughter’s dislike of cheese, yet she still ate pizza and grilled cheese sandwiches. Similarly, when his guests at Alinea didn’t like sea urchin, he thought about the ‘why’ and if he could circumvent their aversion by playing with various variables, including iodine concentration.

So, what do you dislike (with a passion)? What about the people around you? And can you figure out a way to change or eliminate that frustration? Take some time through the idea maze.

In closing

Ideas come in all shapes and sizes. Some may be more obvious than others. Some may snowball into a best-selling one. Although I’ve shared the three most common frameworks that I’ve personally generated and seen others find inspiration, it is, of course, not the only ways to exercise your creative muscle. In fact, the first step into being more “creative” is being cognizant about everything around you.

Two years ago, one of my former professors recommended I start ‘idea-journaling’ every day. Since I’ve started, I began noticing more and more stimuli from my surroundings, conversations and frustrations.

It may be a start, but it’s by no means an end. Stay curious.

Photo Credit: Ariel Zhang @yuzhu.zhang
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Three Types of Mentors

Photo by Rohan Makhecha on Unsplash

Christmas 2019 has finally turned its page, and Santa has granted with us with either presents or coal. Then again, coal may not be so bad. In /r/ShowerThoughts (where I regrettably spend maybe a wee bit too much time in), a Redditor shared that with a little pressure, naughty kids can turn their coals into diamonds.

Possibly deserving coal myself, every year, between Christmas and the new year, I regress to a husk of myself and binge the eight Harry Potter movies. Inspired by the Triwizard tournament, Cedric Diggory’s valiant sacrifice, and in a beautiful Socratic debate with some of my friends on Harry’s most impactful mentor, an unlikely hero came up – Mad-Eye Moody.

The Three Types of Witches/Wizards

As a nerd about mentorship, I believe mentorship is equal parts art and science. Every mentor-mentee relationship is unique like the stripes of a zebra or the folds in a human fingerprint. Along your life journey,you’ll have the fortune of being with many different mentors and mentees. Some are fleeting; some are life-long. Yet, there are still general themes among these relationships. More specifically, I’ve observed three kinds of mentorships:

  • Peer,
  • Tactical,
  • And, Veteran.

Peer mentorship comes from someone who is facing a similar problem to you or has as much experience in a respective field as you do. A peer mentor will be down in the dirt with you, rolling in the mud. Together, you aim to learn how to navigate the complexity of the landscape.

Tactical mentorship comes from someone who has two to five years more experience than you in a field you want to grow in. He/she is someone who is able to able to see around the corner before you do. A tactical mentor can provide the nitty-gritty tactics to conquer many of your challenges. Most startup investors, who see a breadth of deals, but only experience some depth, tend to fall under this category.

Veteran mentorship comes from someone who has already attained the level of success that you hope to one day achieve in a given field. Veteran mentors can help you define your true north, providing both vision and scope. Unfortunately, because it’s been a few since they’ve tackled a similar scope of a problem, they won’t be able to provide the ABCs for you.

Magic and Mentorship

Like the Triwizard Maze, the world around us is always changing, posing new obstacles and surprising us with new challenges. Though not frequently, the variables and parameters for our success will always be changing. Our peer mentors, like Cedric Diggory, Fleur Delacour, and Viktor Krum, are our companions to conquer the seemingly impossible. Our tactical mentors, like those who have been chosen by the Goblet before, help us to make the right judgment at each crossroads. Our veteran mentors, like Mad-Eye and Dumbledore, are our lumos to see a bigger picture. All of them will help us find the signal in the noise. More importantly, are the supporting force that have, is, and will be pushing us forward towards our own Triwizard Cup.

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Five Lessons from “Brunches with Strangers”

Photo by Jay Wennington on Unsplash

One of the biggest aspects I lost when I graduated from college was the social life. All my social interactions these days range from driving distance to the need to cross the Pacific or Atlantic, compared to a simpler time when my friends were within walking distance. So, earlier this year, I started a little passion project: Brunch with Strangers (BWS).

BWS began as an effort for me to:

  • Help overcome my deep fear of public speaking;
  • Have an excuse to bring fascinating souls to the same table;
  • And, help make the San Francisco Bay Area feel just a little smaller and just a little more human.

It’s a Saturday brunch I hold every fortnight between six to eight thrill-seekers, hustlers, crafts(wo)men, entrepreneurs, engineers, and curiously-curious individuals. They are working on interesting projects, have captivating stories, and/or possess an infectious drive for their passion. The key element is that I have to be reasonably confident that they don’t know more than one other person who will be at BWS before the meal, which is, admittedly, harder than I initially thought for folks in the Bay Area. After 20 brunches, with a little over 100 guests and circling back in with 90% of them in the post-mortem, here are the five main takeaways from these enthralling conversations, ordered from the most to least intuitive for me:

  1. Structured conversations work better than unstructured conversations.
  2. Cap it.
  3. The culinary experience doesn’t matter.
  4. Embrace “awkward” silences.
  5. Don’t introduce the guests before the day of the brunch.

Structured conversations work better than unstructured conversations.

But what does “better” mean? I measure “better” by the guests’ answer, a month after the brunch, to the question:

Were you able to catch up with another BWS guest (whom you did not know beforehand) in person?

In the context of startups, that question is how I measure my product-market fit, which I share more context to in a separate post. Guests of a structured BWS are 30% more likely to catch up in person within a month of the brunch than guests who join me in an unstructured BWS. Between structured and unstructured brunches, a structured brunch is when I have at least one activity or topic planned for during the brunch, whereas unstructured brunch, my “control variable”, happens when the guests get to decide how and where the conversation goes, and discussion is more free-flowing.

Over the score of brunches I’ve hosted, the two most well-received activities were 1) a game I call Hidden Questions, and 2) where each guest brings two asks.

Hidden Questions, inspired by Jimmy Fallon’s Pour It Out, is a game where each person has to answer truthfully two to three questions, written by the previous group of people who played the game, but is not required to reveal what the question is. The deck of questions the previous group writes, which even I’m not privy to look through, can cover any topic and ask any range of questions – from favorite books to deepest fears to NSFW ones. Some of my personal favorite are “When was the last time you uncontrollably cried?” and “When was the last time you said ‘I love you’?”. If the person answering the question does not reveal the question itself, he/she has to eat a Beanboozled bean or take a spoonful of one of the spicier hot sauces found on the show Hot Ones. The catch is before the person answering the question decides to reveal question or not, the other guests can ask clarifying questions and bet additional beans or spoonfuls of hot sauce for the person to eat if he/she doesn’t reveal. So, if he/she does, then the other guests eat what they bet. It’s a fascinating game that creates a safe space where people have the excuse to be vulnerable, as well as revealing each person’s level of risk aversion.

On the flip side, to help guests mentally prepare and pick the dilemma of the highest priority, I ask guests at least 48 hours, up to a week, in advance to bring two asks to the brunch:

  1. One that they’d feel comfortable sharing with most of their friends;
  2. And, one that’s either deeply troubling them and require them to be vulnerable, or one that shows a very different side of them that most people they know might not recognize.

The asks themselves are structured by answering two questions: ‘What are you currently working on?’ and ‘What do you need help with?’, which can range from work to personal life to new projects and hobbies to relationships. When the time comes to share the guests’ asks, usually about 20 minutes in, I ask them to share the one they’re more comfortable in sharing. Based on what they share, I can gauge how comfortable they are with the other guests, as well as indicate how well I’m doing my job.

The asks also incentivize mentorship from folks who have had wildly different experiences in different industries at different ages. For example, an autonomous driving product manager provided advice on building systems to streamline communication to a remote workforce to a newly-minted landlord and property manager by predicting actions and that may need to be taken by the landlord’s employees and working to preempt them. In another brunch, an indie film producer taught us all how to hustle, be scrappy, and run effective crowdfunding campaigns by going back to the roots of meeting people face-to-face rather than over the Interwebs. And more recently, a digital nomad shared his $0.02 on how to build a network and community in a new geography and culture from scratch by being willing to do manual labor and noticing when people needed help, to build trust.

Cap it.

One of the best conversationalists I know, Bobby, once told me:

“A great conversation is like flirting with a girl you really like.”

Share enough to make him/her interested, but close the conversation sooner than you’d like to suggest a sense of scarcity, as well as a reason to go on a second date. If you reveal everything too soon, your audience will most likely lose interest as soon as they have no more questions, like how many of my friends have spoiled the whole plot of Game of Thrones (and now it’s The Mandalorian) before I even began Episode 1 of Season 1.

The same seems to be true for the BWS conversations. I found a moderately strong negative correlation between the length of the meal and the number of in-person catch-ups within a month of the meal, after the first one-and-a-half hours (and a moderately weak negative correlation of meal length and number of in-person catch-ups, if the meal length lasted between an hour and an hour and a half).

Both to be respectful to others’ schedules and to motivate them to catch up after, I cap the brunches to 1.5 hours. To be fair, I am still testing out the optimal length of time, since I don’t have a big enough sample size to decide from.

The culinary experience doesn’t matter.

I initially thought that more interesting meals and/or great eats, which at times, fell on the more expensive side at two to three dollar signs, would give folks, in the worst possible scenario, the culinary experience to talk about when they have no other topic or background of each other. It turns out the culinary experience doesn’t have a strong correlation to the reduction of the number of awkward silences, which I assumed would serve as a leading indicator for how likely guests were to catch up in-person after.

In fact, even when guests had the disposable income to afford the meal, when a meal is expected to exceed $50 per person, it is more likely that the culinary experience detracts from how vulnerable a person can be.

The culinary experience will always come second to the guests and the conversation they bring.

Embrace “awkward” silences.

Speaking of awkward silences, my initial goal was to reduce the number of “awkward” silences in a conversation. Maybe it was my anxiety speaking, but I realized two things:

  • What’s awkward to me may not be awkward to another;
  • And, silences are diamonds yet to form (under pressure).

Some people need time to digest everything they have heard up to that point in the conversation. Some people need a break to eat the food they ordered. Some people need time to formulate the next question they want to ask. But for me, silence offers an opportunity to allow guests to dig deeper.

In relation to silence, fours years ago, one of my dearest mentor figures, Robin, shared two rather insightful tips with me:

  1. “Listening is the most important of conversation, and silence, too is one of the sounds a conversation emits.”
  2. “People like to talk about themselves. Give them the opportunity to.”

Silence is that opportunity for people to share more about their life stories. And with the right prompt, it can become a safe space for them to be more vulnerable. And there are two ways I help them continue, with the addendum that I, myself, am vulnerable with them first, earlier in the brunch:

  1. Lean in. Ideally, with an open inquisitive look. I don’t have to say anything, but it will eventually prompt them to continue. It might feel a bit awkward at first.
  2. Ask them to rewind to a point they brought up that I find fascinating, curious, or needs more explanation.

Late night talk show hosts, like Conan O’Brien and Stephen Colbert, and podcast hosts, like Tim Ferriss and Cal Fussman, are really acute at catching these moments and serve as great case studies.

Don’t introduce the guests before the day of the brunch.

At first glance, this seems a bit counter-intuitive. Of course, I want the guests of each BWS to be excited for people who are going to be present at the brunch. I would absolutely love to show off the wicked roster of brilliant individuals each time. What ended up happening is when I did initially release the guest list, many guests did some diligence of the other attendees, and a few came to the brunch with predisposed assumptions of who the others were.

Though most tend to be relatively accurate assumptions, the brunch lost its air of mystery and curiosity which affected the guests in two noticeable ways.

  1. The guests who did their research were less curious on what they thought they knew about another guest and rarely ended up discovering the thought and emotional complexity behind social media posts, titles, and press releases.
  2. Over half of the guests who had been researched felt they couldn’t be as vulnerable as they would have liked, in efforts to “live up” to the expectations of the guests who did their research.

So, going against the grain, I decided, after the first five brunches, to no longer release the guest list prior to the meal.

In closing

With many more to follow, the lessons learned now is only the tip of the iceberg, as I continue my adventure learning from the craziest, the most curious, the most creative, and the most inspiring people out there.

À l’année prochaine!

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Pre-gaming Cold Emails

It’s the holiday season again – my favorite time of the year! From Glühwein to Christmas lights and decorations, it’s the perfect time of year to tackle on many things that bring us cheer. When it comes to the people around us and in our lives, the holiday season is my favorite excuse to catch up with old friends and meet new folks.

‘Tis the Season to Reach Out

Outside the exciting, but tough world of venture capital and entrepreneurship, I enjoy spending time meeting brilliant individuals outside of the technology sphere. To the point, I made a New Year’s resolution half a decade ago that I’m going to meet one new person I’m crazy passionate about every single week. I’ve stuck with that resolution ever since. Obviously, it required me to find a way to get in contact with these amazing folks every week. From cold emails to calls to handwritten letters to knocking on their front door, whether it was going to be a success or not, each week provided me with a new challenge I get excited to embark. And I’ve found that I get the highest positive response rate out of my 52 weeks a year, the five to six weeks starting from Thanksgiving week until the first week of the new year – or in this coming year’s case, the new decade. Over the holidays, it’s true that people don’t check their inboxes as frequently, but it seems that most people who plan to reach out believe that too, and often stall until the new year, at least many of my friends and coworkers do – a sort of New Year’s resolution. Of course, I’m not saying there’s any guarantee in a positive response, but chances do seem higher.

I’d like to start off by saying that in the context of reaching out to individual people that I can imagine becoming friends with, I don’t have any holistic templates for cold emails, outside of a few sentences, which I’ll share in this post. To me, writing a cold email is a labor of love, and it really pays off when I make the content as relevant to the addressee as possible. On the flip side, if the purpose is to spray-and-pray or to gain leads in a funnel, this post may not be entirely pertinent, though there may be sprinkles of fortune scattered below in how I explore the mental maze in sending a cold email.

The Warm Up

Having spent almost a decade in competitive swimming, the first, and probably the most rewarding, yet most underappreciated, exercise I learned was visualization. Visualization comes in two parts: 1) Seeing myself win the race and get my desired time, and 2) Being prepared for any possible resistance or friction to winning. Don’t get me wrong; the race itself is important, but about a year into my swimming career, I started competing increasingly with athletes that were of a similar caliber as I was, where the margin between our best times existed in the milliseconds. And arguably, what makes or breaks the race is how mentally prepared you are before your race even begins – what all the 30-40 hour training weeks will amount to.

It’s the same when I send cold emails. I used to think I was special, having gotten into an amazing university, some of the most competitive and “elite” organizations on campus, and so on. Truth is it was all bullcrap! And sending those cold emails was one element that grounded me. A cold email is nothing but another tick in their inbox – nothing more, nothing less. I’m not allocated more real estate on the virtual battlefield. In fact, in some ways, you could even say I can’t even pay-to-win. If I’m punching above my weight class, then I was and am another competitor, competing for a limited, finite resource: attention.

Jeff Bezos once said:

“If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few companies are willing to do that.

“At Amazon we like things to work in five to seven years. We’re willing to plant seeds, let them grow and we’re very stubborn. We say we’re stubborn on vision and flexible on details.”

Although he said this in relation to building a company, it’s equally true in the competitive landscape of sending a cold email. You have to be willing to push your time horizon beyond any of your competitors. Or in other words, be prepared to go the distance – to play the long game.

What does that mean? Any permutation of creativity juices, like letters sent via messenger pigeon (or turtle doves for this time of year), and recurring emails works. The most important thing to keep in mind, when playing the long game, is cadence and commitment. My default is usually one email a week, usually Monday or Tuesday morning, up to three weeks, with each one showing the positive delta in knowledge acquisition compared to the past week, but still need help in their respective expertise on a particular topic.

Some of my friends and founders I met have tried more extreme versions of what I do. For example, one persistent founder I know once sent the same email every day at 9AM for three months to finally get a meeting with an executive at a major entertainment studio. Another sent the same pitch email to a well-renowned investor every week for a year, and now they’re best buds and play pick-up games every month. The disclaimer is that these may be edge cases, but do be cognizant to never overstay your welcome. If you’re asked to stop, stop.

When should I send a cold email?

On a macro scale, two overarching themes that run in my head are my personal resource availability and timing.

Personal Resource Availability

Outside of the obvious answer of trying to get in touch with someone outside of my immediate network, the question would be better phrased as: When can I not get a solid warm intro? I used to think all warm intros were the same, and that a warm intro is always better than a cold email. Truth is: it’s not always. There’s a huge spectrum to how great (or not) a warm intro can be.

Let’s think about it from the perspective of a Net Promoter Score (NPS). We may all be familiar with the question:

One a scale of 1-10, how likely are you to recommend this product to your friend?

We’ve most likely seen it when filling out a survey after you used or bought a product or service. It’s how businesses measure your satisfaction of their product or service. Although one might think that five is average, anything greater than five is above average, and anything less is below average, the truth is most people regress to filling out ‘7’. ‘7’ is a proxy for not offending anyone but at the same time, saying the the product or service was “okay.” Businesses usually measure 7’s and 8’s as okay, where the real breadwinners are the 9’s and 10’s. Similarly, when I seek or decide to give warm intros, it really comes down to: Can I get or give a 9 or 10-score warm intro? In my head, it subsequently creates a binary scale: a solid warm intro (score = 9 or 10) and a weak warm intro (score ≤ 8).

Subsequently, when should I send a cold email is answered by… whenever I can’t get a solid warm intro.

Solid Warm Intro > Cold Email > Weak Warm Intro

Now, it begs: what are the characteristics of a warm intro? This is decided in two parts: content and matchmaker.

I characterize content in three parts: the subject, the introduction, and the ask. The subject is meant to attract and describe the purpose of the email. The introduction is to explain who I am. The ask, and probably the most important bit, which has to be clear from the beginning, is what I want out of the introduction. With the first introduction, and also for the cold email, I keep it simple to one of two things, depending on the other person’s bandwidth:

  • A 20-minute call or in-person chat (Note: If I go with this option, and the person accepts, I follow up with 2-3 questions I plan to ask during the chat)
  • One burning question

To make it easier for the matchmaker, I often send them a short two to three sentences that summarizes the above, and can easily be forwarded along. My goal is to make it as easy and simple for both the matchmaker and the person I want to get in touch with.

The matchmaker, or the person referring me, is any one or a combination of the following:

  • A subject-matter expert (SME) in my respective field, defined by having a track record for success and external validation by other thought leaders;
  • Someone who knows me (and my work) well, capable of succinctly describing what I’m working on and me, and is excited for me;
  • And/or, someone who knows the person I want to get in touch with well, where the matchmaker is either the first 100 names the person receiving the introduction thinks of, or the first five names in that given field.

Timing

Timing is crucial. And to measure it, I ask myself four questions:

  1. Where are they (in life)?
  2. Where am I (in life)?
  3. What is my purpose?
  4. How can they win?

Where are they (in life)? Is the person I want to get in touch with busy tackling a new project? Preparing for a new baby? Switching careers? On a holiday vacation? If the person has a large presence on social media, most of these can be found online. Take special notice of the inflection points and outliers in their life. Some are more obvious than others. Of course, they’ll be willing to talk about the moments in their life when their second derivative was positive, but I think there’s a bigger story behind the moments when second derivative was negative. Of course, it may be something I bring up later in the conversation depending on how openly vulnerable the person I’m reaching out to naturally is. If the person has a limited presence online, it’s best to ask the matchmaker or mutual friends and connections. Sometimes, I just can’t find evidence of his/her bandwidth anywhere, so I preface my cold email ask with:

I know you’re extremely busy as is. If this does surface in your inbox and you have the time to reply, I’m grateful if you could [insert ask]. Otherwise, I’ll reconnect in one month.

Leaving room for people to not feel bad to say no, and making sure to follow up have been the two hallmarks for me to potentially get a “yes” in the future. A “no” now isn’t a “no” forever.

Where am I (in life)? Have I done all the diligence I could possibly do before I reach out? Anything that is “Google-able” is not worth asking another individual, especially if I’m looking to punch above my weight class.

What is my purpose? Why am I reaching out? What makes this person special? Why might this person be the only one in the entire world who can answer my ask? If I’m reaching out in the networking sense, can I be this person’s friend for at least the next decade?

How can they win? Always give before taking. There’s plenty of literature online, explicitly and implicitly – on social media, in the news, in their public appearances – that would help arrive at what they might need. If I have to ask him/her how I can help him/her, then I’m already wasting that person’s time.

In closing

In a saturated market of information, product-market fit is defined by attention. So keep it personal. Keep it direct. And have some fun.

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Finding Product-Market Fit and “Idea-Market Fit”

Photo by Loic Leray on Unsplash

I was recently inspired by a fascinating conversation between Mike Maples Jr., co-founder and partner at Floodgate, and Andy Rachleff, co-founder of Benchmark Capital and Wealthfront, but more interestingly, the founder of the term, product-market fit, or PMF – a term that signifies when a product is recognized by a strong demand in the market. Over the years, there have been various ways entrepreneurs, go-to-market strategists, and investors have defined when an idea reaches product-market fit. But before I dive into the PMF, let’s take a look at market definitions first, which admittedly is a step off the beaten path.

The Markets

How I Like to Think about Market Sizes. *Not drawn to scale

Traditionally, the total addressable market (TAM), serviceable addressable market (SAM), and the serviceable obtainable market (SOM) are defined according to the geographic location of your market. It makes sense – your market is as big as where you can offer the service. But now, in an increasingly connected world, technologies are less and less inhibited by the geographical boundaries that plagued the decades before. That said, there are still cultural, social and economic differences when accessing new demographics, which is why I like to characterize the TAM, SAM, and SOM by psychological resistances to new ideas. The TAM is still defined by the total upside potential of a product, where it still excludes laggards, or folks who would most likely never (seek to) use your product. The SAM is construed of people who would use the product after three to five friends in their network recommend and are using the product themselves. And finally, the SOM consists of customers who are desperate, as Andy Rachleff called it, for your product. They have spent sweat, blood, and tears finding or building their own solution. They have already traversed the idea maze themselves and put the dollar (or the euro, peso, krone, pound, yen, RMB, BTC, ETH… you get my point) here their mouth is at. And here, in the SOM, is where you find your product-market fit.

Product-Market Fit

PMF is most noticeable on the hockey stick curve. Before PMF, traction is slow and looks very much like the blade of a hockey stick. And after PMF, traction skyrockets and exemplifies exponential growth.

The Hockey Stick Curve

While there are many heuristics to assess PMF across different verticals, I’m the most fluent in consumer tech where I’ve spent most of my time in. And in consumer tech, I’d like to underscore the notion of ‘exponential organic growth’, and subsequently, a short analysis on each word of that phrase.

Exponential is probably the most straight-forward, where at the early stages of a business, we’re looking for rapidly compounding growth.

Organic growth, as opposed to paid growth, is a measurement for word-of-mouth. Investors tend to measure the effectiveness of a product by its virality from its initial customers to its nth customer – growth that is achieved without directly spending (ad) dollars on acquiring the new customers.

Growth is something I break down into – retention and adoption. Increasing adoption is great as measured by the growth of total users on consumer platform or for a consumer product, but focusing only on adoption leads to a leaky funnel, or in my case, trying to hold too many groceries in my hand without a shopping cart. Every time I grab another item on the shopping list, I drop some other item I was already trying to balance and hold. Of course, focusing only on retention means there’s no growth, which for keeping your best friend circle is fine (unless you want a thousand BFFs), but not for growing a startup.

Below are some growth signs to pay attention to signify that your product is near/at PMF:

RetentionAdoption
> 25% DAU/MAU 100s of organic signups/day
40% are active day after signup> 30% MoM growth
Usage 3 days out of every week

“Idea-Market Fit”

As a founder with an ambitious idea, reaching product-market fit is a great goal to have, but the truth is PMF is a mystical beast – a chimera – in and of itself. Market demands change; what satisfied the definition of PMF a decade ago may not satisfy it now and will most likely not satisfy it ten years from now. Many studies have shown that most startups don’t fail from technological risk, but rather the inability to reach PMF, which ends up leading to lack of investor interest, demotivation, and the founding team falling apart. And quite obviously, before you reach PMF, the hardest part about starting a business is reaching PMF, or what Peter Thiel and many call the Zero to One. I’ll dive into the lessons I learned about the journey to “1” in future posts, but for the purpose of this post, I’m going to focus on the “0” – or what I like to call, “idea-market fit“, or IMF.

What differentiates a good idea from a great money-making idea? I’m going to borrow Andy’s thought calculus exercise. In a 2×2 matrix with right/wrong on one axis and consensus and non-consensus on the other, “you want to be right on the non-consensus.”

Andy Rachleff’s 2×2 Startup Idea Matrix

Why? Discounting the situations where you’re wrong (because you don’t make much, if any money), if you’re right on consensus, it means the market’s already mature, and perfect competition in a capitalistic market squeezes you out of your profit margins. If you do pursue this option as a founder, you’re more or less tackling an execution risk. On the other hand, if you’re right on the non-consensus, the market is still nascent, and you have the potential for monopolistic control of the market. In other words, you’re taking a market risk.

It definitely isn’t intuitive. At the very least, it wasn’t to me when I was on the operating side of the table. I wanted validation. When I was at Localwise helping build a community of local talent, I wanted people to say “I totally agree” or “You’re onto something.” But often times, I just received friction and resistance, with the toughest to receive from some of my friends.

“No one would ever buy that.”

“You’re wasting your time.”

“When are you going to get a real job?”

And at some points in time, I did think, “Maybe they’re right.” Until I started meeting a few people who thought a hiring destination for local mom-and-pop shops wasn’t a bad idea, and especially when small business owners started opening up about their frustrations. Hiring platforms, at that time, focused on the sexier brands and companies to get more demand side traction – the Googles, the Big Four’s, or the Bains, but had seemingly completely underrepresented the population of local businesses. Even if these SMBs were on these other platforms, they were overshadowed by the presence of bigger brands.

When validating startup ideas, you don’t want consensus. If your idea is truly revolutionary, people have yet to be conditioned to accept the idea. Take Uber or Airbnb, for example. If you asked the average person if they would use such a product, most would have thought that you’d be crazy to have a stranger sharing a car ride or home with them. These days, take e-sports or streaming. If someone told me in my pre-teen days that I could make a living off of playing video games, I’d most likely think I was dreaming. After all, I grew up playing Snake on my dad’s Motorola Razr, which admittedly seems to have made a return to the markets.

IMF is about challenging convention and the status quo. That’s what makes an idea revolutionary, or as people in Silicon Valley like to call it, disruptive. A crazy good idea challenges the explicit and implicit biases we have about society and ourselves. In other words, we have to detect the deception we bestow onto ourselves to find the gems in the rough, which Josh Wolfe of Lux Capital explains in his 2019 Lux Annual Dinner Talk – one of the best VC thesis-driven thought pieces I’ve ever seen.

In closing

As a geeky quote collector, I’d like to close this piece not in my own words, but in the words of three brilliant investors who have a few more patches of scar tissue on their back than I do now.

“Some of the best ideas seem crazy at first.”

– Curiosity, in my Thanksgiving blogpost

“Most of the big breakthrough technologies/companies seem crazy at first: PCs, the internet, Bitcoin, Airbnb, Uber, 140 characters…you are investing in things that look like they are just nuts… it has to be something where, when people look at it, at first they say, ‘I don’t get it, I don’t understand it. I think it’s too weird, I think it’s too unusual. “

– Marc Andreessen

“Breakthrough ideas have the traditionally been difficult to manage for two reasons: 1) innovative ideas fail far more than they succeed, and 2) innovative ideas are always controversial before they succeed. If everyone could instantly understand them, they wouldn’t be innovative.”

– Ben Horowitz, in his new book What You Do Is Who You Are
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A Little Perspective on Intuition

I was chatting with an artistic buddy of mine about the parallels between craftsmanship and early-stage investing, and the more we dove into it, the more fascinating it became. Very similarly, Ash Fontana of Zetta Venture Partners provides a fresh perspective in an episode, specifically, at the 28:45 mark, on The Twenty Minute VC. But one thing, in our conversation, stood out to me in particular – where, somehow, I never put two and two together – intuition.

As you might’ve noticed on this blog already, I’m obsessed with intuition. I’ve asked many an investor to try to break down their intuition, or unconscious competence, hoping to learn from them in tandem with entrepreneurs I have met over these days. I’ve also asked experts from various fields – music, cinematography, culinary, sports, politics, and more – about their various forms of muscle memory. And my conversation with my buddy reminded me of a short journal entry I wrote over a decade ago, about the first person who described intuition to me:

It was late that summer night. The sun had already set, and the crickets had come out center stage in tonight’s feature performance. The slow chorus of whirring was accompanied by the occasional electrical spasms of the 20th century street lamps right outside the studio.

I was helping my teacher pack up the last of his art supplies and move it to the rusty, old shed in his backyard. As I put all the brushes and paints in their respective shelves, I couldn’t help, but notice an array of canvases lying in the left corner. As my curiosity ended up getting the better of me, it turned out to be a series of beautiful and complex surreal, abstract, and Chinese watercolors – quite the contrast to his usual realistic style.

“What do you think?”

“It’s beautiful,” I replied, as if on autopilot.

He paused for a second.

“David, do you know what the toughest thing to draw is?”

“Maybe this,” gesturing at the canvases I was flipping through like a Rolodex. “Oh! And monsters.”

“I don’t think so,” shaking his head, “it’s humans.”

I couldn’t help but pop my favorite question, as a 9-year old, “Why?”

” ‘Cause we see them every day – on the streets and at home, angry and calm, wrinkled and not, and from the day we’re born till the day we die. So, the smallest of deviations from what we’re familiar with is recognizable, not just to an artist, but any person. The average person may not always know why and how it doesn’t look like the people they’re used to seeing, but they will always be able to tell the difference, before you have a chance to blink.”

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10 Letters of Thanks to 10 People who Changed my Life

Photo by Matt on Unsplash

Every Thanksgiving, I send thank you emails and letters to the people who’ve changed my life to date – from elementary school teachers to career mentors, from friends to family – each one unique to the person who has changed my life. I don’t really have a template for any of these emails or letters. And yes, as the years go on, I will only have more and more people to send these thank you notes to. The time I spend writing each one of these is worth the lifetime each of them gave me. Whether it was just one exchange that opened doors for me or years of guidance, each one of them have my utmost respect and gratitude. In this post, I will share ten letters to the ten people (and their respective lessons and quote) who have changed and continue to change my life, shaping me into the person I am today. To respect their privacy, I’ve abstracted everyone’s names, but that doesn’t change the gravity of my thanks or their lessons.

A little of what to expect:

  1. The One who Taught Me Creativity
  2. The One who Taught Me Curiosity
  3. The One who Taught Me Self-Worth
  4. The One who Taught Me Open-mindedness
  5. The One who Taught Me Empathy
  6. The One who Taught Me Hope
  7. The One who Taught Me Integrity
  8. The One who Taught Me Perspective
  9. The One who Taught Me How to Fail
  10. The Two who Taught Me Education

The One who Taught Me Creativity

“A good student can solve five different problems one way. A great student can solve one problem five different ways.”

Dear Voyager,

I still remember the day, more than a decade ago, when you assigned the class homework over Christmas break. Although I chimed in with the class, complaining before I even saw the assignment, I remember grabbing a bag of Doritos and sitting down to read the assignment as soon as I got home that Friday ’cause, hell, I wasn’t planning to spend the whole break dreading doing the homework on the last day before school started. To my surprise, there was only one problem – a simple one – in the entire assignment, with the footnote: “A good student can solve five different problems one way. A great student can solve one problem five different ways.”

I didn’t realize it that sunny, but cold afternoon, but it was my first exposure to the contrarian view, where breadth was more important than depth. But that enlightenment, admittedly, lay dormant for another decade. It seems most of the people around me readily offered up the statement “depth over breadth”, which I took for granted. I was told it’s much better to be amazing at one thing than really good at many things – to not be a “jack of all trades, but master of none.” And it makes sense. In fact, it’s quite applicable in many careers, where the sole purpose is to dig really deep into one subject.

The day I realized it was three months into my venture capital career, when quite literally, hell broke loose. Five days before the day all of our portfolio startups had to present to an audience of investors, the power in our building went out. Many of the software startups only had to restart their servers, but some others didn’t have luck on their side, namely a hydroponics venture. With the power outage, their water system stopped running, and their plants had wilted over the weekend. Unlike some of the other startups who didn’t need cash as urgently, this one had to raise funds on Demo Day. We tried many different ideas – from placing them under direct sunlight to fertilizing. In the chaos, we were just throwing around ideas, and I remembered what one flower shop owner told me three days before Valentine’s Day. Although I was in a dedicated relationship at the time, I just didn’t have time to buy flowers right before our date, so I asked him, “How can I keep these roses looking just like they do now, but in three days?”

He winked at me, “Cut these stems diagonally, put it in a vase of water. Then add in two bags of sugar from that coffee shop over there and a teaspoon of white vinegar. I promise they’ll look better than they do today.” And that was the same advice I offered that startup. In two days, the herbs came back to life. And on Demo Day, I think they tasted a little sweeter than when I tried them last, but maybe it was just placebo.

Thank you, Mr. V, for your lessons challenging convention, to always question the world around us, and to “unbias” our own perspectives. I wish you and your family the best over this holiday season!

With deep gratitude,

David

The One who Taught Me Curiosity

“Be interested and interesting!”

Hi Opportunity,

You probably don’t remember me in our short email interaction over two years ago in September of 2016. I understand you get hundreds of emails a day, so don’t feel pressured to respond, I just want to thank you.

That said, you said something that has impacted my life in the two years that ensued: Be interested and interesting!

When I was still a student at Berkeley, admittedly, I didn’t really get it. What did you mean: be interested? Was I not interested enough when I was was reaching out to people already?

But now I get it. Quite embarrassing, I used to see networking as a means to an ends – a job, a referral, a means to elevate myself; but over the years I realized that each person are ends in and of themselves. I was interested to be interesting, and it was all wrong! It clicked one day when I was on BART when I saw a middle school friend I hadn’t connected with in a long time. He had fallen, by his words, from grace. He had been kicked out from college, was diagnosed with a medical condition he never thought he had, and at a point in time, when all his friends shunned him for his past mistakes he made in high school. It was a 30 minute BART ride, but I couldn’t help but want to help him no matter what. I couldn’t bear to see him like that. And for the first time, consciously, I cared for someone else outside of family and super close friends without a hope of reaping a benefit. And in the months that followed, they were some of the most fulfilling months that I’ve ever had.

And what you said, clicked. Thank you.

Happy Holidays! I wish you and your family the best of holidays! Stay frosty and stay awesome!

Holiday Cheerios,

David

Personal Note: Funny how I end up taking things to the extremes. I sent this thank you email last year, and I ended up fascinated by various facets of people’s lives, past, and ambitions, but I forgot the the second part of the fundamental equation for developing relationships – be interesting. Over the past year, of the “No’s” I’ve gotten, I’m grateful to the people who tell me I’m just not interesting enough or that I don’t have anything they’re interested in. In the past year, that’s exactly what I’ve been working on (Stay tuned for posts about them.). Relationships exist as a two-way street; you need to be as curious in them as they are in you. From personal experience, most people are fascinating enough, fascinated in ideas, projects, and topics, but not always in people.

The One who Taught Me Self-Worth

“Be proud someone is copying you; that means you have something worth copying.”

Dear InSight,

I hated being copied. I thought my ideas were proprietary to myself. They were mine, mine, and mine. I spent good time on those ideas, trying to come up with the most creative and unprecedented idea for each homework and project you assigned us. Yet, I remember being shamed by people who could make my school life a living hell for not letting them copy off my homework. I wasn’t strong enough to stand up to them. And I kept it all bottled up. Then one day I let it loose when you brought a classmate and me to the side of the class. I didn’t care who was looking or who heard; I just cared about justice. I don’t remember if I held back my sobs or let the tears flow, but I do remember what you said as clear as day. Your next words changed me ever since then. Calmly and surely, you said, “Be proud someone is copying you; that means you have something worth copying.“

I’ve graduated from multiple schools since then. I made many new friends. I’ve tackled a few careers, which you’ve had the play by play every year. And, haha, you’re always more excited about my developments than I am myself. I’ve come to realize that it’s the same in the land of business and startups. If it’s a good idea, the market will crowd around, replicate, and iterate it in the blink of an eye. We saw it with real estate. We saw it with subscription-based models. We saw it with cryptocurrency. It’s social proof that an idea works. As Marc Andreessen, a juggernaut in my industry, once said, “The difference between a vision and a hallucination is that other people can see the vision.”

I started a blog this year with your words in mind. None of my ideas are proprietary. They’ve all been inspired, directly or indirectly, by the people around me. I hope, one day, people will be able take my ideas and make it their own.

Thank you for always being there, especially when I needed it most. Happy Thanksgiving! I wish you and your family nothing short of the best!

Gratitude with gratuity,

David

The One who Taught Me Open-mindedness

“Some of the best ideas seem crazy at first.”

Hi Curiosity,

No idea is ever bad. Only in execution, can we tell the truly crazy from the crazy good. You taught me not to be so dismissive of people and ideas I find to be bizarre, weird, or crazy, but to turn my aversion into intrigue. You taught me to be an optimist when there are so few in the world we live in now, but also that I needed to be one if I wanted to tackle the VC industry. You taught me to stand in their shoes and think, what if this were true? What could happen if the stars aligned?

By giving founders, as well as the people around us, the benefit of doubt, I’ve realized there are a lot more possibilities and opportunities that I once would have never seen behind a closed door. Though it is easier to be a naysayer than a promoter, thank you for teaching me to stay open-minded.

Happy Thanksgiving! I wish you and your family nothing short of the best!

Warmth in thanks,

David

The One who Taught Me Empathy

“The value of [communication] is measured by how much reaches the other person’s ear, not by how much leaves your mouth.”

Hi Maven,

I remember the first time we were finally able to schedule a call between us. You were sick and were flying below the weather. Even though I kept saying that we should reschedule, you insisted that you wanted to help now and keep your word on a commitment that we both agreed on before. That night, your words and actions deeply moved me and within the first ten seconds, you had my unconditional respect for you, your character, and your values. For a complete stranger, you were willing to sacrifice your time and your health.

Over the years, wanting to climb out of the shell of my former shy self, I thought I had to speak more to be heard. And I did, but dialogues became more and more like monologues. You taught me to not be obsessed with what I have to say, but rather be obsessed with what others have to say. And to embrace the silence. You were right. Sometimes, I come out of a conversation more excited and more educated than I went into it. Thank you.

Happy Thanksgiving! I wish you and your family nothing short of the best!

Listening to silence,

David

The One who Taught Me Hope

“Not there quite yet… but maybe one day.”

Hey Orion,

“Not there quite yet… but maybe one day.“

Although you never explicitly said that to me, it was the subject line of our first email exchange, the theme of most of our email conversations, and the emotional backbone for my endeavors. I’ve relied on it since the summer we met. You were there when I asked for best practices for reaching out to when I had to learn how to deal with rejection after rejection.

You taught me how to get back up and how to best set myself up to bounce back after failures. My favorite, which I’ve since shared with many of the founders I work with, is, outside of the corporate board of advisors, to always have a personal board of advisors – a group of individuals I trust to always have my back and whom I can always be honest with. That group is where I can regress to my lowest denominator and be unforgivingly vulnerable, and they’d still be there with my best interests in mind.

Thank you for being one of my personal board members and for your patience as I made mistakes after mistakes. Happy Thanksgiving! I wish you and your family nothing short of the best!

Thankful and Hopeful,

David

The One who Taught Me Integrity

“Pay it forward.”

Dear Spirit,

When we first met as you wrapped up your workshop on how to find the best talent from our own networks, I remember being the last person in line to try to speak to you. Everyone before me asked questions for you to elaborate on what you shared in the workshop, but I kept thinking of all the questions I wanted to ask you. And I knew you didn’t have time to answer all of them. As I unfurled the scrap of notebook paper with all my questions on there, yet nervous, that I would forget how to word each question, you saw it, smiled, and said something along the lines of, “I don’t think I’ll be able to answer all of that. Here’s my email. Let’s set up a time to chat.”

To be honest, I thought you wouldn’t have time to respond if I did email you. But you did reply. And, we scheduled a lunch six months in advance – at that point, the longest I ever had time to be anxious for. Six months later, after lessons on strategies ranging from go-to-market to ideation to mentorship, I asked you how I could repay you for the time, the advice, and the meal. You looked at me with the same smile and said, “Pay it forward.“

I realized that sometimes, the greatest form of enrichment is to know someone you helped is out there helping someone else who really needs it. It is knowing that as a mentor, you’ve catalyzed a chain reaction of virtue and giving. Thank you for that lesson and the many that followed. I promise that I will continue the cycle which your mentors and their mentors started.

Happy Thanksgiving! I wish you and your family nothing short of the best!

With the utmost gratitude,

David

The One who Taught Me Perspective

“There are always at least two ways to look at any picture.”

Dear Magellan,

Every time we started a drawing or painting lesson, you’d always start pointing out these gems hidden from my sight. “Here’s a monkey. There’s that yellow cartoon game character who eats everything. There’s a man’s face. Here’s the number 3.” My reaction always began with “How… Wha- … Ahhhhh”, as I eventually dawn in realization. I swear you’d be the champion of a cloud-spotting competition if there ever was one. You taught me to always look at a picture from multiple angles, drawing from analogies and parallels in the world that I knew to the world you were trying to open to me. Zooming in from big picture to the granular scale, from the dark spots to the light spots, from the angles to the boxes, any monumental project would seem much simpler when we broke it own to things I knew.

You also taught me that before I put my pen, pencil or brush on the canvas, I have to plan my entire journey before I begin, which seemed counter-intuitive to me, yet to be able to adapt to “happy accidents” on the fly if need be – switching seamlessly between organization and spontaneity.

You taught me art, in itself, is a science. It is purposeful. It is the culmination of all my previous experiences and scar tissue. It is a hypothesis of the mind put on paper. And the more I look into a piece, the more questions and the more complex it becomes. It is a canvas representative of the landscape, depicted by the bumps unique to each and the ephemeral edge or a pencil or brush. And it is the job of the artist to isolate variables to produce the best possible result.

At the same time, what you taught me is also true in life. Life is as much an art as it is a science. Life requires us to use organization and spontaneity interchangeably to capture the best opportunities. But your most important lesson, in art and in life, is the ability to observe, understand and empathize from multiple perspectives, so that we can be more self- and situationally-aware ourselves, as well as make better decisions.

Thank you for your lessons that have persisted across time. Thank you for teaching me to be open to new possibilities, resourceful, focused, and resolved. Happy Thanksgiving! I wish you and your family nothing short of the best!

Still painting my life’s canvas,

David

The One who Taught Me How to Fail

“Don’t fail slowly; fail fast.”

Hi Endeavor,

You taught to put the face of failure in the form of the macro, to help me conceptualize how inconsequential failure is. Twenty years from now, will I still remember? Or will I really care? If so, will I really want to shackle the rest of my life? In the grander scheme, can I afford the downtime between testing hypotheses? 30,000 days to live, not a single one to lose.

Thank you always for cutting the bullshit and for your radical honesty – the wake-up call when delude myself with dreams of grandeur, but sometimes, unwilling to accept the reality.

To the person who always took the shortcut to tell me of my folly, I hope you didn’t take shortcuts on the 24-hour marinade on that turkey. Happy Thanksgiving! I wish you and your family nothing short of the best!

Learning from failure,

David

The Two who Taught Me Education

“A smart person learns from his or her own mistakes. A genius learns from the mistakes of others.”

Hey Discovery and Dawn,

Words cannot describe the fortune I have to have been with you from day one. There are many things I’ve learned from both of you. There are even more things I am thankful for that I’ve been given, directly and indirectly, explicitly and implicitly, from both of you, but the greatest is definitely the ability to learn – to be able to weigh, rationalize, and grow by being a sponge. You always said, “Nothing you learn is ever wasted.“

Knowing how to learn, not just the action of learning itself, has me always hungry for knowledge – in books, projects, podcasts, and people – to live vicariously through mediums that are not native to me. I can only say I am still working on it and that I will continue to figure out not only new depths in knowledge, but also the processes to enhance knowledge acquisition.

This year, I’ve realized that writing has helped my knowledge retention – both in my idea journals every day, as well as through weekly blog posts. And only more to come!

Having both of you is my greatest fortune and my greatest asset.

Happy Thanksgiving!

I love you,

David

Final Thanks

As I mentioned before, these are only some of the many people I’m thankful for – people that I’ve known for years, people who offered me 20 minutes of their time, people who live across the globe, people who are no longer with us, and people who never asked for anything in return. I would love to include them all here, but unfortunately, I don’t have the real estate or time to put them all here. The above are all lessons I learned, sometimes a little later than I would have liked, but I hope my pitfalls won’t be yours and my learnings will. After all, one of my mentors did say, “A smart person learns from his or her own mistakes. A genius learns from the mistakes of others.” And, finally, you, my readers, have my eternal gratitude in reading what I have to say, as I learn to get step by step closer to escape velocity, by learning from those who have a few more miles on the odometer.

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Investing in Mentorship

In theory, there’s nothing wrong with seeking mentorship to gain experience or offering mentorship to give experience. In fact, advice is still something I seek, as I’m still on the green side in the larger landscape. In reality, every person only has 24 hours in a day and limited bandwidth, which inhibit the quantity and quality of mentorship even if the mentor wants to. Providing mentorship, after all, requires mentors to accept the opportunity cost to do something else they could be doing, and prioritize the learning exchange. I characterize mentorship into two categories: passive and active. Passive mentorship is where one purely obtains advice from a mentor, whereas active mentorship is where advice is coupled with hands-on learning experience.

Mentorship is often seen as a huge time commitment, which is why when asked to provide mentorship, many potential mentors, who have yet to commit a large chunk of their schedule to advisorship, turn it down, as soon as they get the request. Having led three mentorship programs across two organizations, as well as hosting founder brunches and brunches with strangers for peer mentorship, here’s why most prospecting mentees are turned down: ensuring value and capping the mentor’s own downside.

Ensuring Value

When mentors are approached, the two most frequent asks are: “Can you be my mentor?” and “What can I help you with?“

The former, “Can you be my mentor?“, often scares many mentors away. Just the word ‘mentor’ or ‘mentorship’ incites the connotation that the mentee is setting a high bar of attention expectation, which in undefined with no clear asymptote or time horizon, in sight. Something I learned over the years, unless I am the one hosting a mentorship program, is that the best mentor-mentee relationships, never mention the word ‘mentorship’, at least not in the first few exchanges. The question itself is nebulous in nature. The nebulosity leaves the mentor needing to expend their creativity to guess what mentees would like to learn. A better approach would be to have a targeted question detailing exactly what you want to learn, with evidence of putting in work to resolve the question beforehand.

Here’s a format I personally use when reaching out for advice, or for passive mentorship:

“I’ve been obsessed about X recently, and have tried out Y and Z, to produce Y’ and Z’ results (where I expected Y* and Z*). As someone I deeply respect in X industry and whose insights I have used in trying out Y and Z, what might I be misunderstanding or should have done differently? If I caught you at a bad time of the year, is there someone or some literature you can point me to, to help me achieve the desired result?”

The latter question, “What can I help with?“, unfortunately, is evidence that the prospecting mentee has not done their diligence. Take for example, helping a VC. There are really only five ways to help:

  • Deal flow – amazing startups that fit the partner/fund’s investment thesis
  • Sales/BD intros – firms that are buying, partnering, or co-investing into the fund’s portfolio
  • Portfolio support – helping the fund’s existing portfolio startups with their various impending dilemmas
  • Follow-ons – downstream investors for the fund’s portfolio
  • LP (limited partner) intros – high net-worth individuals or groups who may fund a VC’s next fund

In knowing one’s specific skill set and network, ideally, a prospecting mentee can help where his/her strengths lie. This is also true on a broader scale, when offering help to friends, acquaintances, and just people who need help, knowing what kind of help they need and when they need it means the world to those in need. After all, a friend in need is a friend indeed.

Capping the Downside

Most mentors, either explicitly or implicitly, want to ensure the experience is valuable and productive to the mentee, leaving the upside to be essentially limitless – for both the mentor and mentee. Having a set of clear measurable goals, one, defines the time horizon, and ,two, helps the mentor understand what is valuable to the mentee. A good reference point are how companies structure KPIs, or key performance indicators. At the same time, clear, measurable goals helps the mentor cap their maximum downside, so the relationship won’t end up becoming a slippery slope. Consider what the mentor has to risk to help the mentee: time, attention, money, reputation, opportunity cost, “knowledge IP”, and so on.

Per the format I use as I mentioned before, it caps the maximum time investment a passive mentor needs to provide to the length of time it takes to answer one question. Or if they’re short on time, I have recognized that they’re busy, and have given them an easier ‘out’ to the question.

In closing

This piece isn’t meant to disincentivize people from seeking help and mentorship, but rather to provide another perspective to those of us, including my younger self, who have yet to figure out their own approach to mentorship or are looking to explore other methods or just to peer into my mental calculus. Mentorship, at the end of the day is an investment – an attention investment. As with all investments, the goal is to lose little, win big – or how we like to say in VC, “de-risk the investment.” The upside, or if I’m continuing on this VC analogy, the return on investment, or ROI, knows no bounds. Even for the mentor, who at first glance, may seem to be losing more than winning, gains the satisfaction and pride of paying it forward, a new friend, and leadership skills, even before what the future may realize.

After all, some of the greatest figures in history and in our world today grew from mentorship: Socrates to Plato, Ralph Waldo Emerson to Henry David Thoreau, Ed Roberts to Bill Gates, Maya Angelou to Oprah Winfrey, Sire Freddie Laker to Richard Branson, Bill Campbell to Steve Jobs, Steve Jobs to Mark Zuckerberg, and the list goes on and on. As many studies have shown, and of course, with a few caveats, happiness can be achieved by spending money on others. In this case, that money is time and attention.

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