Tag: mentors

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Mentors and Investors

There is an incredible wealth of people in this world who self-proclaim to have insights or secrets to unlocking insights. From parents to teachers to the wise soul who lives down the street. From coaches to gurus to your friendly YouTube ad. To mentors. To investors. While there are a handful who do have incredibly insightful anecdotes, their stories should serve as reference points rather than edicts of the future. Another tool in the toolkit. No advice is unconditionally right nor unconditionally wrong. All are circumstantial.

After all, a friend once told me: All advice is autobiographical.

The same is true for anything I’ve ever written. Including this blogpost in itself.

Over the past two weeks, as a first-time mentor, I’ve had the incredible fortune of working alongside and talking to some amazing founders at Techstars LA. At the same time, I was able to observe some incredible mentors at work. And in this short span of time so far, I’ve gotten to understand something very acutely. The dichotomy between mentors and investors. For the purpose of this blogpost, I’m going to focus on startup mentors, rather than other kinds of mentors (i.e. personal mentors). Although I imagine the two cohorts of mentors are quite synonymous.

While the two categories aren’t mutually exclusive, there are differences. A great mentor can be a great investor, and vice versa. But they start from two fundamentally different mindsets.

Investors/mentors

An investor tries to fit a startup in the mold they’ve prescribed. A mentor fits themselves into the mold a startup prescribes.

An investor thinks “Will this succeed?” A mentor thinks “Assuming this will succeed, how do we get there?”

An investor starts with “Why you?” A mentor starts with “Why not you?”

An investor evaluates how your past will help you get to your future. A mentor helps you in the present to get to your future.

An investor has a fiduciary responsibility to their investors (i.e. LPs). A mentor doesn’t. Or a mentor, at least, has a temporal responsibility to their significant other. Then again, everyone does to the people close to them.

An investor will be on your tail to hold you accountable because they’ve got skin in the game. A mentor might not.

You can’t fire your investor. You can theoretically “fire” your mentor. More likely, you’re going to switch between multiple mentors over the course of your founding journey.

An investor has a variable check size-to-helpfulness ratio. Who knows if this investor will be multiplicatively more helpful with intros, advice, operational know-how than the size of their check? A mentor has theoretically an infinite CS:H ratio. Check size, zero. Helpfulness, the sky’s the limit.

It’s also much harder to find a mentor than an investor, outside of startup communities, like On Deck and Indie Hackers, and acceleration and incubation programs, like Y Combinator and Techstars. Frankly, being a mentor is effectively doing free consultations over an extended period of time. And if you’re outside of these communities, the best way to bring on mentors is to bring them on as advisors with advisor equity. I would use Founder’s Institute’s FAST as a reference point. And Tim Ferriss‘ litmus test for bringing on advisors: If you could only ask 5-10 very specific questions to this person once every quarter, would they still be worth 0.5% of your company without a vesting schedule?

In closing

As I mentioned above, being a mentor and an investor isn’t mutually exclusive. The best investors are often incredible mentors. And some of the greatest mentors end up being investors into your startup as well. Having been in the venture world for a while, I’ve definitely seen all categories on this Venn diagram. Sometimes you need more of one than the other. Sometimes you need both. It’s a fluid cycle. And for the small minority of venture-scalable startups, it’s worth having both.

Photo by Robert Ruggiero on Unsplash

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Losing is Winning w/ Jeep Kline, General Partner at Translational Partners and Venture Partner at MrPink VC

“I was a swimmer since I was very young and, you know, I never won. I never won.”

You’re probably assuming this is how the opening scene of a movie about a future world-champion swimmer begins. The beginning of the world’s most amazing underdog story. And you’re wrong. Well, not completely wrong. This isn’t a story about the world’s next biggest Olympic swimmer. Although it might be well-timed with the Tokyo Olympics around the corner. This… is a story, in my humble opinion, of one of the world’s next biggest venture capitalists. A story of a young Bangkok girl who became a VC from learning how to lose.

I’ve never been the smartest kid on the block. At least in the IQ department. So I make it my mission to hang out with folks who are smarter and more driven than I am. Jeep is no exception. I met her last month. And as if going from a World Bank economist to Intel leadership to startup advisor and investor to lecturing at UC Berkeley’s Haas School of Business was not enough, in our first conversation, she shared an incredible set of contrarian insights. So earlier this month, I had to jump into another conversation with her.

Something about going long

If you’re a long-time fan of this blog, you know one of my favorite Bezos-isms is, “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.”

Jeep is that same kind of superhuman.

“I started as a competitive swimmer since I was seven, and I swam so much and so hard, like three kilometers a day. It’s just a lot of practicing. I never even won a medal. And I kept doing it. And that was hard.

“Because other kids they got medals in different styles. So I learned early on in life what losing actually meant. And I think that’s very important because a lot of smart kids, they never learn how to fail early on in their life. And it’s kind of like a winner’s curse because you know, when they’re the best at everything, since they were young, throughout college , once they come out, and they realize that the world is hard, they are doing things or want to pursue a career that their parents cannot help them, they become risk averse. Meaning they don’t want to try new things.

“So I never won in [any] swimming competitions. Until I got into college. When I got into college, at the time I already quit swimming. I quit in high school. So, I didn’t swim competitively anymore since I didn’t have time to practice. I picked up other activities like piano, which I came to love. In college, one of my friends asked me, ‘Hey Jeep, why don’t you come back to the competition?’ And she knew I never won. We were in the same race at so many events. And I said, ‘I don’t know. Let me try.’ So I tried again.

“So I got back to the practice routine. Adjust my strokes a little bit. And then I won. I got gold and silver medals for a college swimming competition. And I was like, ‘This is a joke. How could I win?’

I never won ever, like for ten some years. And I joke with my friend, ‘You know why, because everybody else quit!’ They quit about the same age in high school.

I just went for it. And that was one of the moments in life that I realized that it’s all about grit. You do what you love and you don’t quit. There will be a moment that you win.”

The analogy extends further

“Failure is the mother of success.” It’s an ancient Chinese proverb that my mom used to tell me again and again growing up. Every time I “failed.” Scored low on a test. Embarrassed myself on stage for a school musical. Placed fourth, right off the podium for multiple competitions. It’s funny thinking about it in retrospect since she turned out to be the exact antithesis of a stereotypical Asian parent. And I love it!

Take tbh, an app where you send your friends anonymous compliments, as an example. It launched back in late 2017. 73 days after its launch, it went from zero to 2.5 million daily active users, which subsequently led to a $100M acquisition by Facebook. To many, tbh looked like an overnight success. But it wasn’t. Nikita Bier, co-founder of tbh, and his team spent seven years with 15 failed products before they arrived at tbh. And with each iteration, they learned and compounded their lessons from their previous failure.

Clubhouse’s Paul Davison and Rohan Seth is another example of a seemingly overnight success. From Talkshow to Highlight (acq. Pinterest), the pair went through at least nine failed apps before they arrive at Clubhouse – last reported to have passed 10 million users. And valued at $4 billion. Their lead investor, Andrew Chen at a16z, spent eight years getting to know Paul.

One of my junior swim teammates told me years ago when I was at my prime, “David, I don’t think I can beat you as you are now. But I promise you I will beat you one day, even if that means after you retire.” At the time, I dismissed it as just another snarky comment, which athletes are prone to make from time to time. But now that I’m a bit wiser than I was in high school, I find that same comment incredibly prescient. It just so happened that a few years ago, we raced each other again. Both of us had long exited the competitive arena, and he won.

In closing

Near the end of our conversation, Jeep cited something Soichiro Honda, the namesake for the Honda Motor Company, once said. “Success can be achieved only through repeated failure and introspection. In fact, success represents 1% of your work which results only from the 99% that is called failure. Many people dream of success. To me success can be achieved only through repeated failure and introspection. In fact, success represents 1% of your work which results only from the 99% that is called failure.”

She further elaborated, “For people who grew up in a society, in a culture that does not easily accept failure, I want them to know that it’s actually not a bad thing to try and hear rejection. But along the way, they have to make sure that they learn.

“It’s the same thing when I teach UC-Berkeley students. I told my brilliant graduate MBA students that there is, for me – and it’s true – there is no stupid question. If other people think your question is stupid, but at least you learn. If you learn, there’s no stupid question. Do not ask good questions, if it means you don’t learn anything.”

In a way, I’m reminded of a peculiar quote by Karl Popper, “Good tests kill flawed theories; we remain alive to guess again.” While Popper was known to be quite the contrarian thinker of his day, the same seems to hold for questions. Good questions kill flawed theories. We remain alive to learn again. After all, speaking from personal experience, I often find myself burning the midnight oil to ask the perfect question. But in the pursuit of asking the “perfect question”, I’ve forgone the adventures I would have had to arrive at the answer I thought I sought.

We learn when we fail. We learn, to one day succeed. The greatest are the greatest because they have a higher propensity to fail than the average person. As the great Winston Churchill said, “Success consists of going from failure to failure without loss of enthusiasm.”

And as Jeep said, “Winning is actually losing, but learning along the way.”

Thanks Jeep for helping with earlier draft edits!

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#unfiltered #15 “You’re Only Here Because You’ve Won” – Thoughts on Systems, their Flaws, and Better System Design through Diversity at the Table

swimming pool, diversity and inclusion

It was late that summer Friday evening. The sun had just crossed the horizon, changing the sky from blood orange red to a deeper indigo. Having put in 9000 yards, half of which were back-to-back sprints, we finally wrapped up our 2-hour practice, exhausted and slightly bewildered.

‘Twas our new coach’s first day on the job. We were expecting a chill practice, but this stranger made us work for it. And he did not beat around the bush. Relentless. In sum, he was the Gordon Ramsay of swimming.

Needless to say, he didn’t make the best impression on the team. And it was fair to say that some of my teammates were not his biggest fans. As they all shuffled out, and I had to wait for my parents to come pick me up from practice, I helped Coach with pulling the tarp covers over the pool.

Breaking the silence, he asks, “David, d’ya like to swim?”

“Of course,” I reflexively reply.

“Why d’ya like it?”

“It’s fun. I made friends. It helps me de-stress.”

“No.” And his next few words changed my perspective forever – both in swimming and in life. “You like to swim because you’ve won.”

Showing Gratitude

Obviously, in my prepubescent self, I took my coach’s comment for its face value. I like to swim because I’m good at it. Or at least, relatively speaking among my peers at that point in time. But as I grew older, that comment resonated with me on a different wavelength.

And a conversation with world-class hustler and founder of Fleeting (a company changing the landscape of trucking), Pierre*, last Friday reminded me exactly why. What I said then about why I liked to swim wasn’t completely wrong. I was able to achieve a moderate amount of success in the sport because my parents, coaches, teammates, and other friends supported and cheered for me. But I also forgot to thank one more for my accomplishments. The system itself.

*You can catch a glimpse of Pierre’s amazing story on Gimlet Media’s The Pitch.

The System

The system itself, included:

  • Rules,
  • Privilege of having access to swimming pools,
  • Privilege of having access to coaches and supportive and ambitious teammates,
  • And, the seemingly minor technicalities,
    • My lane’s timers had faster reaction times compared to my competitor’s lane’s timers. For context, in regional meets, each lane would always have 3 timers each to record when you touched the wall on your finish, and they would take the median time as the final result.
    • My lane’s touchpad was working, but my competitor(s) may have had to rely on manual timers since their touchpad didn’t work. So, when it came down to close races and who touched the wall first, I would win.

Of course, there were moments I was a victim to said system as well. And I remember those moments far better than when I won as a result of the system.

So what?

The thing is, when everything is going my way, I often take it all for granted. One of the only times I realize and realized that there might be any flaws to the system are when I am left out. I have been and am a member of society that has profited from the systems – in swimming, in higher education, in work opportunities, just to name a few. And I’m sure there are even more I have yet to realize that I have benefited from.

The past few weeks have been a wake-up call to America, to the world, and to myself for what we have all let pass without questioning. And admittedly, it may be difficult to assess what explicit and implicit biases we have when we, in the words of Coach, are “winning”.

Diversity at the Table

So, it comes down to two fronts: internally and externally.

Internally, introspectively, let’s ask ourselves:

  • What have we won as a result of? And, what are we still winning in?
  • What have we benefited or profited from?

And just as there are winners, there exist still who have yet to win. Or win in a more consistent manner.

Externally, we need to bring into the fold those who have yet to win to help us assess what systemic flaws exist in our status quo. Frankly, it’s incredibly difficult to find our implicit biases alone. I know that I’ve been reminded multiple times in my life by those who are more cognizant in those arenas than I was and have been. And, those underrepresented and underestimated by the system can use all the help they can get.

Together, I’m confident we can find a better solution.

Photo by Marcelo Uva on Unsplash

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

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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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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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