Tag: swimming

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#unfiltered #55 Short Spurts of Motivation

motivation, walk

Over the past two weeks, I’ve been working on a new blogpost about self-doubt, which I expect will come out soon. Or rather, soonTM. At the same time, after watching a week’s worth of incredible aquatic talent, I saw as the era of the swimming greats I grew up with came to a close. Michael Phelps. Natalie Coughlin. Nathan Adrian. Allison Schmitt. Anthony Ervin. Jason Lezak. Cullen Jones. Kosuke Kitajima. Dara Torres. And much more.

They were part of the defining score of years that brought the sport into the limelight. To most, most of the above names carry little gravity, outside of Phelps. But to me, they were the names that had me huddled around the TV. Watching the prelims. The semis. And of course the finals. They were the names that inspired me to be better.

As Ervin said, “We are the oldest of the fastest and the fastest of the oldest. We are men between worlds.”

But as they came back for one last curtain call this Olympic Trials, I couldn’t help but recall their influence on me in some of my most formative years. Whether I need that extra push for the most challenging project in my life to date or that shoulder to lean on when I am at my worst, there’s one race I cannot help but think about.

Just like when a Yahoo! exec told the Reddit co-founders that they were a “rounding error” and the team subsequently decided to frame it on their office wall as motivation, in 2008, the US Olympic 4×100 freestyle relay team faced a similar dilemma. Despite having Phelps on the relay team, they weren’t the crowd favorites. The French were. They – the American team – were the underdogs.

In fact, that 2008, French team boasted some of the fastest sprinters in the history of the sport. Alain Bernard who had just won his gold in the 100 meter freestyle. And Amaury Leveaux who had taken the silver in the 50 meter freestyle. And besides Lezak who tied for bronze in the 100 meter freestyle, none of the others on the US team had medaled for a short-distance freestyle event that Olympics.

Pound for pound, the US relay team had to deliver not only their best, but beat their best. To have a chance at beating the French team. So for motivation, they read Bernard’s comment in the papers over and over. “The Americans? We’re going to smash them. That’s what we came here for.”

Phelps leads the race, giving his team a slight lead over France. Weber-Gale holds that lead for the Americans. Jones, the slowest and the third leg of the team, yet still punching every inch of his worth, gives the lead back to France. And Bernard, the world champion in the 100 free, against Lezak for the US, gets a strong lead for a race and a length he is already the best in the world at. Lezak trails behind by over half a body length at the flip. 50% done of the last leg of the race.

I remember sitting in front of the television screen, screaming and hoping my voice would reach the Water Cube in Beijing. “C’mon… c’mon! C’mon!!” Lezak, at 32, one of the oldest competitors in the pool that year, pulled together what could only be described as sheer willpower. Those last 50 meters… seemed to have been the longest 23 seconds of my life. A breath for every second that passed. A breath for every second Lezak pulled closer to Bernard. And in the last ten seconds, minus the sound of the TV, the room was silent. As some people might say, you could hear the sound of a pin drop. It did. With a margin of eight hundredths of a second.

One of the tightest and most inspiring races in all of history. If you ask me, the greatest. And the race I watch time and time again when I am at my worst.

You have to see it for yourself to really believe the excitement.

Top photo by Tegan Mierle on Unsplash

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

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

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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 #43 Do I Like to Write?

writing, how to start a blog

An investor I had recently been put in touch with asked me this past Monday if I like to write. I thought it was a peculiar question at first. But it strangely kept gnawing at me as the week went on. While I can’t say for certain that it was that investor’s intention, it became a forcing function for me to reflect on my motivations.

If you’ll believe it, I used to hate writing. With a capital H. I used to dread when a teacher or professor would assign us essay prompts for homework. Many of my college and high school friends can probably attest to that fact. More so, I was the world’s best procrastinator. Ok, “best” might be overselling myself. But I had a track record for deferring my 10-/20-page essay until the night before it’s due. It was the antithesis of fun. I knew exactly what my professors sought. All I had to do was put the puzzle pieces together. Frankly, writing was a necessity to survive my academic career, not one I’d seek out as a passion.

It wasn’t always that way. In elementary school, I loved writing poetry. An exploration of my inner creativity, unrestrained by the educator’s whip. I also took part in school poetry competitions. As time went on, writing lost its sparkle, between book reports and persuasive essays.

Before this one, I started two other blogs. Neither of which lasted past three months. Both of which I started back in college. Looking back no one asked me to start a blog, much less three blogs. But looking back, I attribute each time I started a blog to the professors I had. Particularly by their rare ability to make learning fun and contagious. It was much less the content of each class, but rather, the fact that we graduated each class armed not with just answers, but with two other faculties I found indispensable over the years:

  • The ability to ask nuanced questions,
  • And the ability to find answers and questions to answer those questions.

My senior year in college I had a third catalyst for writing. As you guessed, also inspired by my professor for a class I didn’t have many expectations for when I signed up, despite hearing glowing reviews from my friends. That year I began writing in journals every day. There is no catch. There are no cheat days. We just had to ideate at least once every day. No matter how long or how short it took, once a day keeps the demons away. At the same time, outside of a promise of commitment, there were no rules. There were no rubrics. No one would grade us on how and what we wrote. Full, uncontrolled creative liberty.

It took me about three months. Slowly, but surely, the spark returned. Over time, journaling evolved into blogging. The best part is I don’t even know what the next stage of my Pokemon evolution will look like. I won’t go in depth here on how I journal these days, but if you’re curious…

Over the past year, I’ve had an increasing number of friends and readers reach out to me and ask me how writing comes so easily to me. It sure didn’t in the larger arch of my life. And not, it doesn’t… not always at least. Some days it takes longer than others. But just like how I wake up and exercise first thing in the morning, journaling is a muscle I am training every day, if not multiple times a day. Whether it’s in my journal or on my Google Keep app or on a Notion page.

That said, I think I’m far less coherent as a speaker than as a writer. I’ve had friends and mentors tell me over the years in conversation, “David, you’re not making any sense.” Unfortunately, in more occasions than I would like, I have a feeling of cognitive dissonance when speaking, which I am actively working to mend. After all, I can only hide behind the veil of asynchronicity for so long. Ironically, I’ve been engaging in more and deeper synchronous conversations than asynchronous over the course of the pandemic.

Luckily, I also haven’t gotten writer’s block yet ever since I began this blog. But there have been certain weeks where I’ve been frustrated at the quality of my journal entries. Enough so, that it never makes it onto this blog. So it goes to say, I never run out of ideas; I just sometimes run out of ideas I think are nuanced enough to share. After all, it’s why I started the #unfiltered series. George Orwell once said, “If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.”

In closing

I never started this blog with the intention of tracking viewership growth. But I’d by lying if I said I wasn’t grateful and elated to see the reception of some of my essays. On days when readers reach out and say thank you, I really believe the sky’s the limit. When I reach out to people I look up to and they mention in our conversation that they enjoy the content I write, I struggle to contain my smile.

My swim coach once asked me semi-rhetorically, “David, why d’ya like to swim?” To which he followed up and said, “You like to swim because you’ve won.” While in terms of numbers I’m still far from “winning”, this modest scope of reception so far only compounds upon my creative joy.

When I pursue any endeavor in my life, I always ask myself: Are there skills, relationships, and/or enjoyment I build that transcend the pure outcome of this endeavor? (Or two cousins of this question here and here.) For this blog, yes. And it boils down to three reasons:

  1. I write to think. It’s a process of self-discovery. On the flip side of the same token, it’s to prevent my prefrontal cortex from atrophying.
  2. Creative joy. There’s something just so satisfying when a blank canvas turns into a cohesive illustration of my mind’s entropy.
  3. And knowing that, no matter how miniscule, it’s inflected a handful of people’s lives upwards. That, and knowing that every so often, somebody out there will smile as they read this.

Photo by Aaron Burden on Unsplash

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

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

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Being the Only > Being the Best

crown, being the only, startup, marketing

This week I revisited David Sacks’ essay Your Startup Is a Movement. It was first brought to my attention during my conversation with Yin Wu, founder of Pulley. And again, with a friend who recently jumped into venture after an operating career, particularly around the topic of our investment theses. Our conversation underscored his fourth point in his Movement Marketing playbook.

david sacks, craft ventures, your startup is a movement, category leader
* Excerpt from David Sacks’ Your Startup Is a Movement

It’s much easier to compete in the market of one – the only one – than in a market to be the best one. As some VCs call it, companies that are “allergic to competition.”

Why?

The goal for any startup is to achieve product-market fit before your competitors, especially your incumbents, notice the market opportunity. Frankly, the incumbents have more cash, more talent, more resources, more in every regard except one… problem obsession. Insatiable desire to fundamentally change the way we live. And with that desire comes speed.

It reminds me of a time over a decade ago, right after the spectacular Olympics which put the greatest Olympian of all time on center stage. Our swim coach asked the team, “How do you beat Michael Phelps?”

A few of my teammates suggested we work longer and harder. Another suggested that we should’ve started younger. And another suggested we wait till he retired. But my coach responded, “Just don’t race against him in butterfly. Race him in breaststroke.” While Michael Phelps is by no means slow in breaststroke, still faster than 95% of swimmers out there in it, the theory holds. It’s the stroke one would have the best chance to beat him in. But what stood out to me most was what the wisecrack on the swim team shouted out as an answer.

“He can swim while I run.”

And he was right.

Another fascinating aspect I realized in hindsight was that no one suggested the question was impossible.

Photo by Ashton Mullins on Unsplash

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How to Identify Market Opportunity and Recognize Market Inefficiencies

round gold colored pocket watch

I was raised a swimmer. From 4 years old, my parents sent me to take swimming classes for 2 primary reasons:

  1. Learn how to not drown.
  2. If we (my parents) are ever going to drown, you’re going to save us.*

*Note: I’d like to point out the irony is that both of parents know how to swim themselves. Not at a competitive stage, but enough to survive from drowning.

Oddly enough, I learned how to swim by drowning. Over the years, like many other children around me, on top of swimming, I also played ball in its various sizes and ran. And I learned that swimming and running are of the 2 purest forms of athleticism and exercise out there. There’s very little margin for error, if any. A tenth of a second is the difference between Olympic gold and not even qualifying for the semifinals. Because of that, in swimming, we’re taught to be efficient. We learned to maximize for our distance per stroke (DPS). And I believe in running, it’s distance per stride.

Efficiency. The ability to do more with less.

The market of efficiency

These days, getting from point A to B isn’t as difficult as it used to be. Cars made travelling miles easier. Planes, for hundreds to thousands of miles. Bikes and scooters, for last mile transportation – distances too close to drive, but take twice as long to walk. Outside of transportation, career development, information and skill acquisition have all seen massive developments not only in the last hundred years, but especially in the last 10 years. Online platforms, like Coursera, Masterclass, Google, and Wikipedia, helped us all shave off months, years, even generations of legwork and information acquisition. They made so many things more accessible.

Accessibility

Accessibility is platformitizing and democratizing information. What Yellow Pages did for services. Reddit for knowledge acquisition. Amazon for shopping. Google for information. And Food Network and food media did for cooks. The average person today is more knowledgeable about the culinary process and its accessories than someone two decades back. Laughable now, but 8 years ago, it’s how I learned not to burn frozen pizza. I could go on and on.

But, in the next ten years, accessibility may not be enough. Though there are many populations in this world who still have yet to access the knowledge I can readily find on my laptop, accessibility provides people with the tools, but not the means to use those tools effectively.

Ease

Ease does. Lower the barriers to entry and bundle the entire knowledge acquisition, or otherwise, what I would call onboarding, in an intuitive manner. Like what WordPress did for websites. Instagram for photos. Opendoor for home-buying/selling. TurboTax for, well, tax.

It’s a messy web of information out there. As economist Herbert A. Simon puts it:

“A wealth of information creates a poverty of attention.”

Here’s an easy way to tell which industries and processes lack ease. Find where people have created hacks to solve a problem.

  • Using multiple tools/software to solve a single problem;
  • Using a “temporary” solution to solve a repetitive problem. Like a basin to catch the rainwater that leaks through the roof;
  • A public forum, like Reddit or a Facebook group or multiple similar questions on Quora, where people share their “life hacks”.
  • A How-to YouTube video that has tens/hundreds of thousands, if not millions, of views.

And to know if you hit the nail on the head, you’ve got crazy pull. Product-market fit. PMF. When you don’t even have the luxury of time to worry if you have PMF ’cause your customer success inbox/sales inbox is filled to the brim. Or you’re getting so many new users that you’re figuring out how to upgrade your servers before your servers go blank. For more on PMF, I highly recommend checking out Lenny Rachitsky‘s recent post surveying 25 of the most successful companies on when they realized they had PMF.

In closing

Tools and platforms that make it easier for an individual to go the distance, to be more efficient, carry 2 traits: accessibility and ease. With each stroke, with each action one takes, they can go further. They can do more. With less. Technology, in the incoming years, will further do so.

And as a VC scout, I look for, what I call – distance per action. Or DPA, for short. So, if you’re working on something that will enable people to have higher and greater DPAs, I wanna talk.

Photo by David Bartus on Pexels.com

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The Punchline

comedy, the punchline, fundraising, vc

“Hey, y’all wanna hear a joke?” one of my teammates in my lane asks during warm-up. If there was the equivalent of a class clown in the pool, that’d be him.

“Why not?” the rest of us answer, hoping to spice up the impending 2-hour practice.

“So, there’s this guy who’s about to ask this girl out to the school dance. But to do so, he’s gotta ask her out on Valentine’s Day. So the day before, he goes to buy a Valentine’s gram during lunch. Turns out – there’s a long, long line.”

Our coach blows the whistle, and we sprint off. When we touch again, he goes on, “And there’s a separate line to buy the roses. So, he heads over, and turns out – there’s a long, long line.”

Again, the whistle goes off, and upon return, “So, he finishes buying his gram and roses. On the fateful day, she gets it all and says yes. Super excited, the guy prepares for the school dance. First he goes to buy his tux. When he arrives at the tailor-“. He pauses, beckoning us to finish his sentence.

“There’s a long, long line,” we chime in. In the distance we hear, “Lane 1. Stop talking!” Whistle blows, and we go…

And return. “He gets his suit tailored. Now he goes to Office Depot to buy his cue cards and markers to ask her out. But when he gets to the cash register…”

“There’s a long, long line.” And a kickboard comes flying in and smacks two of us in the face. “Quiet!” a distant shout.

“Day of the ask, he assembles all his friends, lines them up for a dramatic prom ask. And what do you know?”

“There’s a long, long line.” Another one of us feels the sting of hard foam across our face.

“The girl says yes. And now, finally the day of the prom arrives, and he picks her up. Together, they take pictures with everyone else, in a-“

“Long, long line.”

“Then they all drive to the destination of prom. But turns out they’re not the first ones there. Ahead-“

“There’s a long, long line.” At this point we were too vested in the joke. Each of us with bruises across our face – just short of our coach dragging us out of the water to discipline us.

“So the boy and girl finally make it into the dance hall, and while they’re waiting for the dance floor to open up, the boy asks us the girl, ‘Can I get you something to drink?’ And she says, ‘Sure.’ So, he goes over to where the fruit punch is. And, turns out…”

“There’s a long, long-“

“Nope, there’s no punch line.”

The bigger picture

I hear so many founders tell me they’re pursuing this billion dollar market. Or even a trillion dollar one with a capital T. And how they plan to capture 10% of this huge market in 5 years. I mean, c’mon, how awesome would 10% of this billion dollar market sound for our returns?

For an investment of anywhere between $1 and $10 million, let’s say $1 million (’cause this is usually something people raising a pre-seed/seed say), 10% of $100B market is $10B. And for the ease of calculation, let’s say by the time the founders exit, we still have 10%, 10% of $10B is $1B. For only $1M invested, $1B is a 1000x return. Wowza!

The true let-down happens when they finally share what their solution is. And it turns out to only address a small fraction of their total addressable market (TAM). Here’s a hypothetical example. A team is tackling a TAM for events of $1.1 trillion (2018 number). They talk about how awesome a CAGR of over 10% is. And how virtual events are the new trend and might accelerate that number even more. I’m thinking, “Hell ya, this’ll be epic.”

Then their product – the punchline… an app that streamlines coffee service at events in 2020. While this may or may not be an exaggeration, many startups find their pitches in a similar format. On one end, as a founder, you want to tackle the biggest market you can – to attract investors hoping to make large returns. On the other end, you want to be realistic with your expectations, as well as your investors’. Often times, it’s a fine line. I get it, which is why I suggest approaching market-sizing from the angle of pragmatic optimism.

The GTM strategy

After you share such a lofty goal, the inevitable question comes along: “What is your go-to-market (GTM) strategy?” The usual answer is some permutation of the below:

  • Google/Facebook/other ads,
  • Get it on the App Store (and/or Play Store),
  • (Pay for) SEO,
  • Hire a C_O (fill in the blank)
  • Hire a growth hacker,
  • Or more engineers, or for that matter, anyone,
  • We were hoping you (the investor) could help us with that, once you fund us. 🙁

But who are we kidding? No one. While none of the above answers are unilaterally incorrect, all the above show characteristics of someone who isn’t a hustler, who isn’t scrappy, and who probably isn’t one to scale a business. A pitch deck is designed to be short. I get it. There’s a lot you can’t fit on to it. But I’m not alone when I say this, we want to see the why and the how behind the what. A bit of Simon Sinek‘s two cents – start with why.

  • Why are you hiring more people? To do what?
  • Why did you choose Google over Facebook ads? Over Reddit, Instagram, Tiktok, you-name-it ads? Over traditional billboards?
  • What is the end goal?
  • What is the core metric you’re optimizing for? In the near term? In the long term? Before your next fundraise?

Just to be clear, just because a founder approaches market analysis from a top-down approach doesn’t instantly disqualify him/her. But it is a red flag. That’s why I’m a huge proponent of bottoms-up market-sizing.

Bottoms-up… and Cheers!

How many customers do you plan to have by the end of this year? By the end of next year? The year after?

How much do you plan to sell your product/service for? How will customer acquisition cost (CAC) get cheaper over the next few years? What will you need to do for CAC to get cheaper?

Eventually, you build out this road map of what the next few quarters and years will look like. You, effectively, plot out, here are the next few milestones we need to hit as a team. And those milestones are quantifiable and actionable – a clear sense of direction for your team and for your investors. Of course, as any road map goes, all subject to change depending on the situation.

In closing

Just like a great joke, you, the founder, need to be capable of delivering the punchline in your pitch deck. The build-up is the problem in the market and the world-class team you’ve assembled, as well as why it means so much to you. The punchline is the solution you’re building. Always, make sure your punchline delivers.

  1. It’s relevant to the rest of the (comedic) routine.
  2. When it hits , it’s at the minimum, satisfying, as a climax. At the maximum, like a world-class punch, it knocks the wind out of your audience.

In the words of Robert McKee, a Fullbright Scholar who’s coached over 60 Academy Award winners, 170 Emmy recipients, among numerous others,

“At story climax, you must deliver a scene beyond which the audience can imagine no other.”

Your punchline, your product, by the time you deliver your pitch’s climax, must deliver a utopia beyond which your investors can imagine no other.

Photo by Ben White on Unsplash

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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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The Third Leg of the Race

swimming, the third leg

I dedicated three-quarters of my life before I turned 18 to swimming. More than half of which I spent competitively. Although I never amounted to a Michael Phelps or Katie Ledecky, the years I spent swimming were some of the happiest, yet character-building times of my life.

I was a mid-to-long-distance swimmer – anything between 200 yards (or meters) to miles-long open-water swims in the SF Bay. By golly, the waters in the latter ‘pool’ were dirty. I couldn’t see my own hand when I reached out underwater. But I digress. As a distance swimmer, the biggest lesson I learned was how to fight the mental battlefield.

The Legs of a Race

Coach taught me to break every race down into 4 quarters. The first leg, the second leg, the third leg, and the last leg.

The first leg is comparatively the easiest. You’re brimming with energy, motivation and (potentially nervous) excitement. As long as you don’t exhaust yourself in this leg, but put in enough effort to break away from the pack, you’re golden. And in doing so, you’re going at 80% of your top speed.

The second leg is when you start engaging in a psychological battle with your competitors. Understand where they are in the race, as well as their racing personas.

  • Are they a front-half or back-half swimmer?
  • Are they a sprinter from the blocks?
  • Do they typically negative split in a race?
  • In an individual medley (IM) race, what’s their best stroke? Their worst stroke?

I typically dial back to 70% speed.

The last leg is probably the second easiest. You burn everything and anything you have in the tank. The goal is in sight – within reach. It comes down to how well you’ve raced the first three legs, and how much you trained. Effectively, it is a battle of strength – a Hail Mary. 110% speed.

Now let’s rewind back to the crucial leg I skipped. The whole reason I started writing this post.

The Third Leg of the Race

Whereas the second leg is based on ‘external warfare’ and the last leg is based on ‘physical warfare’, the third leg, and arguably the most important, is one based on ‘internal warfare’. By this point in the race, you’ve exhausted more than half of your energy, yet you’re expected to output more than when you started. You’re worn and tired. And, you can’t see the goal yet, so you know you have to save some strength for the last leg.

Yet, if you can hold this leg, it can mean the difference between a win and a loss. If you lose this leg and succumb to your thoughts, your chances of winning are slim. Quite frankly, it sucks.

So I made bets with myself.

“If I can finish this lap in 14 strokes, where I’m reaching out and scooping that ice cream just out of my arm’s reach, I’m going to treat myself to some Haagen Dazs after. One scoop for every lap I succeed in.”

“I’m going to flip turn faster than my opponents. And if I can do this thrice in a row, I’m going to get rock-solid abs when I finish this race.”

“I’m going to hold my breath till the other side of the pool, so I can smell and taste the teriyaki chicken.” *At swim meets, they’re always selling teriyaki chicken and rice for lunch. It’s greasy, super salty. But if you add some sriracha, it is a hungry swimmer’s heaven.

As you might notice, some of my bets were outright ludicrous. But it was because they were crazy that I was motivated to keep going. When there were no tangible goals, I made my own.

Why am I sharing this?

Life, seeking employment, running a business, and so much more run in the same way. After your academic career, no one really tells you what your goals are or can be. You have to make your own. When you’re job-seeking and no interviews are coming your way, you have to muster the strength to continue applying – either spraying and praying or finding creative ways to obtain certain opportunities.

In startup land, day 1 till day 365 (or even till day 730) will be a honeymoon. It’ll be the first leg. You’re hacking away by yourself or with pals on something you feel strongly about. For many, your next leg is scoping out the competition and pacing yourself.

  • Should you launch with press releases on TC, NY Times, etc?
  • Should you stay in stealth?
  • Can you continue bootstrapping?
  • Do you need to hire more people to help you out?
  • Which distribution channels are the most effective? Overlooked by competitors, but you think there’s a lucky draw in it.

And then, there’s the third leg. The leg that will decide if your adoption curve forms a hockey stick or a pitcher’s mound. You have a vague idea of where you need to go, but you haven’t hit critical mass. You’re questioning your initial assumptions. You might even be questioning yourself. Did you make the right calls? Is there anything you missed? What went wrong? Should you have just taken the job your friend offered?

But if there’s anything we’ve learned from some of the best entrepreneurs out there. It’s the ones who weather the storm – the ones who have that grit – that often make it. Being able to weather that third leg doesn’t guarantee success. But not being able to weather it is close to a sure-fire for failure.

As a world…

We’re on the third leg now.

And what we do now will decide if we win or lose the race.

Photo by chuttersnap on Unsplash

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Setting Culture

Photo by Aron Visuals on Unsplash

I just started my second read of Ben Horowitz‘s new book, What You Do is Who You Are: How to Create your Business Culture. It’s a brilliant deep dive on what culture and virtues mean for a growing company or team. From the most successful slave revolution in history to prison culture to the samurai bushido, Ben draws parallels between those and startup culture, where you can get a snapshot here.

On page 31, Ben wrote “Create Shocking Rules.” Why “shocking”? So people will ask why. So people will pause, think, and remember them. What is “shocking”? In a time when raping and pillaging was the norm, Toussaint Louverture, the man who led the Haitian Revolution, forbade officers from having concubines. And he kept to that promise. When “shocking” isn’t the only game changer, you need uncompromising commitment to those rules. Weak follow-through is another fallacy in creating the culture you want. What you let slide will define the new culture, with or without your approval.

Sun Tzu and the Concubines

Rereading about Toussaint Louverture reminded me of a story my dad used to tell me by my bedside. About another brilliant general, who lived 2000 years prior to Toussaint during the Spring and Autumn Period, and best known for authoring The Art of War, Sun Tzu.

Through his thirteen chapters, dubbed The Art of War, he eventually earned an audience with the king of the State of Wu. Hoping to test Sun Tzu’s strategies to its extremes, possibly expecting to see Sun fail, the king asked Sun to test it on his harem of concubines.

After accepting the task at hand and separating the concubines into two companies, Sun had them all take a spear in hand and said, “I presume you know the difference between front and back, right hand and left hand?”

The women answered, “Yes.”

After explicitly explaining what “Eyes front”, “Left turn”, “Right turn”, and “About turn” meant, he issued his first order at the sound of the drums, “Right turn.” But, the concubines responded with fits of laughter. Sun Tzu proclaimed, “If words of command are not clear and distinct, if orders are not thoroughly understood, then the general is to blame.”

In another attempt, he called out, “Left turn.” His words met the same fate as the ones he uttered just prior – with laughter. This time, he said, “If words of command are not clear and distinct, if orders are not thoroughly understood, the general is to blame. But if his orders are clear, and the soldiers still disobey, then it is the fault of their officers.”

Subsequently, he ordered the heads of the two companies beheaded, whom happened to be king’s favorite two concubines. Seeing what had unfolded from his pavilion, the king sent a messenger to plead with Sun to keep his two favorite alive. But Sun did not relent.

After their execution, he immediately installed two new officers, and from then on, the concubines followed every order that Sun issued to the T.

Using the principles he shared and taught in The Art of War, Sun Tzu won many battles for the State of Wu, most notably, when Sun Tzu led an army of 30,000 to defeat an enemy numbering ten times more than the troops from Wu. As Jon Stewart, former The Daily Show host, once said:

“If you don’t stick to your values when they’re being tested, they’re not values: they’re hobbies.”

In Closing

In his book, Ben shares quite a bit how some of the best leaders in the world shaped their organizational culture. It wasn’t from catered lunches or having dogs in the office every Friday. Culture comes down to setting “shocking” rules, paired with a set of priorities, and more importantly, keeping them. Culture is what your team members remember about your organization and how it made and makes them feel 20 years down the road.

Though not perfect, my former swim coach instilled the same virtues in us. He was never a fan of tardiness. To him, it demonstrated a lack of character and commitment. And to enforce that, if we were late, by even a minute, to get into the water (not arrive at the pool), the offenders had to swim the entire warm-up in butterfly – the whole 2000 yards. And not one person escaped that law, not even him – not that I ever saw him late.

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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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