Not too long ago, I published a blogpost walking through my top 9 founder questions that deserve more attention. In it, I detailed:
The questions
My rationale for asking each of them
Surprisingly, it did really well. A few folks reached out to me before that post, which inspired its due subsequence, asking if I had a repository of questions to share. And after, asking me to do more of such calculi.
Just got asked by a friend on how I come up with questions.
1st thought, idk it just happens.
2nd thought, naw, I know I spend too much time swimming in my head.
So here's a thread 🧵. Hope it's useful to someone out there (Or an excuse to say I worked today):
While I’m compiling something of the like on the backend, with no real deadline, as it’ll grow over time, I thought I’d dedicate a series on this blog to new and old questions that come into my purview. Each paired with:
Why I ask it the way I do
In what circumstances do I find myself asking it
And if applicable, how I build up to asking that question
And as bowtie to wrap everything up nicely together, I’m calling it the DGQ series. Or Damn Good Questions. Or it’s counterpart, Dumb and Garbled Questions. I’ll let you decide what each question stands for. But I’m really not the best with naming conventions, so if anyone has a better one, I’m all ears.
As the rocket takes off, I thought I’d begin by sharing the question that inspired me to start this new series.
What would [20+age] year old [name] say about the [name] that sits before me today?
For instance, what would 45-year old David say about the David that sits before me today?
I’ve heard many variations of this question, but the wording of this question in particular is an ode to my buddy, Matt, founder of nomofomo and UCLA’s President of Thought Lounge. After all, many of the best ideas I have in my noggin’ right now are not my own. This question is no exception.
There’s this great line from the song A Million Dreams, which I’m going to spare you my sad excuse for a karaoke singer, that goes like: “I don’t care, I don’t care, so call me crazy. We can live in a world that we design.” As luck would have it, I found it when I read Mike Maples Jr‘s piece from last year on backcasting. Which, if you have a spare 10 minutes, I highly recommend checking out as well. And speaking of quotable lines, he wrote, “The future doesn’t happen to us; it happens because of us. The future is not like the weather. It doesn’t just happen. People make the future. It’s not a destiny or hope; it’s a decision.”
He goes on to say, “Breakthrough builders are visitors from the future, telling us what’s coming. They seem crazy in the present but they are right about the future. Legendary builders, therefore, must stand in the future and pull the present from the current reality to the future of their design.”
Similarly, not only the greatest founders, but I also found that the greatest life athletes live in a similar mantra. It takes real courage to stand where no one is standing and decide that is the direction you want to pursue. You might be right; you might be wrong. But there’s something to be said about the clarity you will have when you live life under the assumption that you’ve already done it.
For example, I suffer from stage fright. But I find great comfort in visualizing myself doing what scares me the most again and again, until I get comfortable standing on stage. Imagining myself giving the same talk in front of one friend, 10 friends, 50 people and even 5,000 people. Each time I level up, I imagine the fear as well as the excitement that comes with it. Embracing both the former and the latter.
In a similar way, the way the future me looks at the naïve me of today helps me find the elusive confidence I need when I’m in doubt. Would future me look at today me and shake his head in disappointment or pride? What would he tell me to do if he sees I’m struggling? And when I myself cannot manifest the courage to take a step forward, my wiser and more resilient self will manifest the destiny I am meant to walk.
As Suleika Jaouad, author of the memoir Between Two Kingdoms, once said, “[The] act of writing a future dream in the present tense has really kind of helped assuage that fear.”
So ask yourself, What would the Future You say about the You that sits before me today?
I imagine even if you don’t find powerful answers, you’ll find powerful questions that will serve as guiding principles in your own life.
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For today’s blogpost I’m going to try something new. It was requested by a reader of this blog, which for anonymity’s sake, I’ll call P. For those who live a busy life, prefer audio over text, or just find my font choice appalling, I thought I’d record myself reading the below text. Think of it like the audiobook version of this essay.
If you love or hate this format, I’d love to hear what you think. Feel free to comment below, or DM me across any of my channels. Any and all feedback welcome with open arms.
Over the years, I’ve used many different versions of the question: What would you do if you knew you would fail? Or, What would you do regardless of the outcome of the endeavor? And as long as the reason for doing so contains any combination of:
Skill acquisition
Invaluable experience
Or relationship/friendship that I value more than the project itself
… it’s a “Yes” for me. The “Yes” becomes an exploration of depth. An optimization strategy for my strengths. My superpowers. It’s something I learned from quite a few of my mentors over the years – both in an official and unofficial capacity.
Subsequently, I’ve had this belief for a long time, which will probably cause some uproar somewhere, that we shouldn’t optimize our life around reducing our weaknesses. But rather, focus our time on maximizing our strengths. That doesn’t mean we shouldn’t ever work to ameliorate our incompetencies. But:
Just enough that we meaningfully reduce our risk of ruin. Any more, there are diminishing returns over time. Forgiving my esoteric economic jargon, we should only work on our weaknesses so that we don’t lose our ability to survive. For example, if you don’t know how to cook, you shouldn’t aim to be the best Michelin-starred chef in the world, but just enough so that you don’t starve to death. Assuming your goal in life isn’t in the culinary world.
Mitigate our weaknesses that are the most adjacent to our core strengths. For instance, in my opinion, one of my greatest relative strengths is my ability to ask questions. I am by no means the best, but compared to the rest of my skills, this is one I find myself shining in a bit more than my peers. Which effectively meant I was always interested in what others were up to and how they thought. A mentor figure told me years ago that it didn’t matter how interested I was in others, no one had a reason to be interested in me. Which meant that one of my greatest and most adjacent weaknesses was to be interesting.
People who have superpowers often carry super-weaknesses. The greater their superpower, usually the greater their weakness. Humans aren’t great multitaskers. We were never designed to be. If you’re saying yes to one thing, you’re saying no to a hundred other things. Are you willing to shoulder that opportunity cost? Sometimes you are, but be very deliberate about it.
Fairly recently, I was presenting to an amazing cast of board members in a board meeting. There was a general consensus around the fact that we lacked focus as an organization, yet we were sitting on a wealth of talent. To which, one of our board members redirected us to Steve Jobs’ infamous speech when we returned to Apple in 1997. One line in particular stood out to me: “Apple is executing wonderfully on many of the wrong things.“
He follows up to say: “The ability of the organization to execute is really high though. I mean, I’ve met some extraordinary people at Apple. There’s a lot of great people at Apple. They’re doing some of the wrong things because the plan has been wrong.”
Taking a step back, as humans, as working professionals, as entrepreneurs in each and every one of our own rights, we often “execute wonderfully on many of the wrong things.” Often times, that’s on our own weaknesses, rather than our strengths.
Living in a simulation
Imagine that we live in a simulation – an MMORPG. Or, massively multiplayer online role-playing game. We start off with a finite number of stat points. The starting number of stat points varies from person to person, depending on your socio-economic class and your given genetic code. You can allocate those stat points however you want.
You can spread them all out evenly, where you’ll never have any true weakness, but neither any true strength. You’ve hedged your risk of ruin. It’s going to be really hard for you to lose, but you can never really win.
On the flip side of the token, you can minmax your build, using gaming terminology. Double down on a stat, to achieve the equivalent of a superpower, compared to your peers. But often times, if you are maximizing on a superpower, you’ve minimized your proficiency in another area. Luckily, as in any game, and as in reality, you can pick up tools and make friendships along the way that will supplement your weaknesses with their strengths.
Of course, as all analogies go, there are exceptions. But as far as I know, there are far fewer exceptions than those that fit into this analogy. And, technically, our ability to level up is infinite. The only upper limit is that, like everyone else, we have 24 hours in a day and a finite number of years to live.
So, where am I going with this?
Super-tools for (super)weaknesses
What do you not want or don’t care to have a superpower in? For the skills and tasks you use everyday, but don’t care to be the best in the world for, leverage software and tools to automate your work, so you only need to spend the minimal amount of time or energy to make sure it doesn’t become a stressor for your day. In the above gaming analogy, you use items to compensate for specific stat deficiencies. The more efficient the “item”/tool, the less energy you need to expend to make up for a super-weakness.
Here are the tools I use to supercharge my day, so I can spend more time enhancing my superpowers and less time mitigating my super-weaknesses.
Descript
Descript makes me feel like a god. As much as I love Adobe Premiere Pro, it had an incredibly high learning curve. But once you got it, they have some of the most robust tools on the market. On Descript, I love how I can edit an audio or video clip just by deleting words in the transcript. And if I mess up, and I do quite a bit, I can always voiceover in the editing process to make myself sound smarter than I actually am. Even better, I can drag and drop music, video and sound effects. If you’re listening to the audio version of this essay, you might have noticed I don’t have any of the afore-mentioned effects. The goal here was just to get you my thoughts as quickly as possible, without trapping myself in audio perfectionism.
If the Adobe Creative Suite is the endgame, Descript is the early game. And it helps you ace it remarkably well.
Notion
Notion is a dark horse (for me). I’ve seen startup data rooms, personal blogs, internal wikis, and even VC investment theses and fund strategies being produced on Notion. It always seemed like a nice-to-have. In all fairness, I didn’t give it the benefit of the doubt it deserved until late last year. Its greatest ability isn’t the ability to create a robust website or the prettiest blog. Its greatest ability is that it gets people to put ideas and thoughts on paper as quickly as possible. The barrier to entry is so low that its greatest competitors are note-taking apps, like Evernote or Google Keep, for early users. Then, you can go from notes to fully functional site in minutes.
And ever since, I’ve been a geek over it. There’s this great thread on Twitter by @empirepowder about all the applications you can build using Notion extremely quickly – from creating a blog from scratch to publishing a course to tracking analytics on your page to the ultimate tweet tracking tool.
For many of us, the hardest part about doing anything is starting. Notion solves that.
Undock
Take scheduling as another example. I know very few people, if at all, who want to be the best scheduler in the world. I know I don’t. But I find myself spending an undeserving amount of time trying to schedule meetings, rather than actually having meetings or being productive. Enter Undock. “The fastest way to find time to meet with anyone.” That’s from their website. And it’s true. When I’m in my Gmail scheduling calls/meetings with founders or investors, I never leave my email tab nor do I ever touch my mouse. No matter how many people are on the email thread, I can find time for a meeting, on average, in two seconds. That’s no joke. I timed myself.
Meetings are about communication, connection and collaboration. But maybe you’re just exhausted from scheduling them. Look, Undock is actually not “just another scheduling app”. We’re a super calendar and we come in peace.
Having and empowering others to have superpowers is literally in their DNA.
Superhuman
I’ve heard many great things about Superhuman, and about a quarter as many bad things about the platform. Superhuman’s claim to fame is being able to get you to inbox zero via one of the most seamless and fastest email experiences ever – through shortcut keys, follow-up reminders, and social media insights just to name a few. Their user interface makes it incredibly easy to respond from one email to the next, even when you’re offline. They have this 100ms rule, where every interaction should be faster than 100ms to make communication feel instantaneous. And they do deliver.
Many of its customers include investors and founders. Busy people who have more unread emails in their inbox than they care to count. Most of the bad reviews I hear from friends and colleagues are that $30/month is just too expensive.
There are many ways to look at the $30 price tag. It’s $12 more than Netflix’s premium plan, and Netflix serves you new content you might not have access to otherwise. Superhuman serves you the same content that would have been yours anyway, just in a new light. On the flip side, $30/month is $1/day. Less than a cup of coffee a day, assuming you buy your coffee every day. But even if you only bought $3 coffee twice a week, $30/month would still be cheaper.
Or in a different lens, Superhuman’s core audience – founders, investors, busy people who have hundreds of emails a week, if not a day – their time is worth at or more than $30/hour. So, if on a 160-work month, Superhuman collectively saves their customers more than an hour of time every month, then it’s worth it to them.
The way I look at it, it’s a bargain. But I don’t use it. Why? It’s not because it’s too expensive. Neither because I don’t have enough emails to go through. But rather, I happened to optimize my email workflow before I even heard of Superhuman. I’ll save that topic for a later blogpost. But if you don’t have a way to get to inbox zero (unless you don’t care. I have a number of friends who have tens of thousands of unread in their inbox. That scares me)… but if you do care about the piling mound of emails, Superhuman’s really got it in the bag.
In closing
And maybe this post might serve helpful in reframing on how you can live your most optimal life. Supercharge your strengths. And find the best tools and mental models you can to protect your downside. It’s okay if you’re not the best at the latter; you don’t have to be.
I mentioned a few of the tools I use, but your mileage may and probably should vary.
While there are tools out there that supercharge your ability to execute and perform, equally so, you’ll find there are amazing people out there that complement your weaknesses. Friends, colleagues, co-founders, life partners. In the words of Steve Jobs, find and meet “extraordinary people.” To do so, as my mentor told me, you’ll have to be interested and interesting.
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!
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.
#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!
I’ve alluded to my ability to say “No” in many previous blogposts, like this one. But as this concept has crawled around in my subconscious for as long as it did, I believe it now deserves a blogpost in its own right.
As a kid, I learned from my parents to say “No” to strangers. The “uncle” who’d say my dad told him to pick me up. Or the “auntie” who’d offer a lollipop to me and ask me where my parents were. To the point it became muscle memory to say “No” to gifts, as well as compliments, even from friends and family. Over time, that notion became more prevalent as it infected other parts of my life.
I learned to discriminate my time before I had a chance to fill in my calendar. Even worse, when I ever hesitated, it became a no-brainer to say no. And subsequently, I missed out on more opportunities I can count. “Whenever there is any doubt, there is no doubt.” It’s a line from De Niro’s character in the 1998 movie Ronin. In essence, if you ever hesitate, some part of your body is telling you “No” while other parts are telling you “Yes”. And there’s a good chance that that “No” is right. Or if you do say “Yes” and things go awry, the voice in the back of your head that said “No” will only exacerbate into full denial. And you may end up hating the reasons you said “Yes” to before.
But it wasn’t from that movie, when that line became immortalized in my mind. I heard it uttered by Tim Ferriss on one of his regular episodes. Or maybe it was from one of his books, like Tribe of Mentors. But I wouldn’t sweat the details.
The thing is, he’s completely right. Both De Niro’s character, Sam. And Tim. But I learned there’s a caveat. Earlier on in your life and career, it’s about taking in more experience since your 24-hour day has yet to fill up. You have to say “Yes” before you know how to say “No”. I overvalued on advice and undervalued experience. Both Sam and Tim were right. But they were right in their own lives, or rather they were right when I would one day have enough things to say “No” to. All advice is, after all, autobiographical.
100 minus your age
I don’t remember where, but I once heard this amazing heuristic for picking up new books. 100 pages minus your age. It equals the number of pages you should read before you decide whether to put down the book or not. The younger you are, the more pages you should read to understand if this book is worth your time or not. Why? Because you simply don’t have large enough of a sample size to recognize the patterns of good versus not-so-good literature. As you grow older, the fewer pages you need to read before you decide if the book is worth your time. Over time, you have a better grasp as to what quality looks like.
A similar notion seems to apply to your life. 100 points minus your age. That’s the margin of error you have when making decisions. The younger you are, the more prone you are to making wild mistakes. The older and more experienced you get, the better you can tell good from bad decisions.
In closing
I’m reminded of something Henry Ford once said. “Whether you think you can, or you think you can’t – you’re right.”
I lost out on many opportunities. The thing is no opportunity will ever be perfect. But in thinking each opportunity I take had to be perfect, I thought I couldn’t – shouldn’t – take it. But frankly, I just wouldn’t. I became a professional brat. There will always be something or somethings that just don’t make the opportunity click. But in saying “No”, you are saying “Yes” to the status quo. That’s something I have to remember.
As Eric Schmidt of Google fame once said, “Yes is how you get your first job, and your next job, and your spouse, and even your kids. Even if it’s a bit edgy, a bit out of your comfort zone, saying yes means that you will do something new, meet someone new, and make a difference. Yes lets you stand out in a crowd, be the optimist, see the glass full, be the one everyone comes to. Yes is what keeps us all young.”
#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!
I have this conception of a personal Hall of Fame. For every piece of content, individual, and or experience in my life that has drastically changed the way I live or the way I think about life. Upon entrance, I find myself facing three large corridors – each adorned with text in Garamond font, framed in the corpse of a giant oak tree. In the corridor to the left, it’s the “Content Hall”. Arguably, the most competitive of the three halls to get into.
I only meet so many individuals in my life. I would say somewhere on the magnitude of tens of thousands. To pick tens of individuals among 10,000 is a 0.1-0.2% chance of induction.
The same is true for experiences. Excluding my daily habits of sleeping, eating, and others that have become second nature, there are very few extraordinary experiences among the ordinary. And in pursuing something extraordinary over a prolonged duration, that something extraordinary becomes ordinary to you. So, over time, you end up regressing into a step-wise function of finding the extraordinary in the extraordinary. To choose from a select few of these extraordinary in the extraordinary experiences at various learning curve spurts leaves an even smaller sample size.
Yet the same can’t be said for content. We consume a plethora of content on a daily basis. From obvious content drops, like YouTube, books, shows, and podcasts, to the non-obvious, such as emails, conversations, street signs, and opportunities that make you pause in the buzz of daily life. With tons of constant inputs from multi-directional sources, picking the handful that has altered your life’s course has a far lower acceptance rate than being struck by lightning.
For me, one of the greatest pieces that exists in my “Content Hall” is The Tail End by Tim Urban. There are a multitude of great anecdotes in it, but my favorite of which is, by the time we turn 18 years old, we’d already have spent at least 90% of our time with our parents.
Presidents
Say I live to 90 years old. In my lifetime, I get to see 22 US presidential terms. 22 presidents max, but many presidents hold office for two terms rather than just one term. There’ve been 46 presidents in the history of the United States so far. 21 of which served two terms. For ease of calculation, there’s about a 50% chance that any president will hold office for two terms. That’s 16 presidents, give or take, throughout my entire life. I’ve lived through Bill Clinton, George W. Bush, Barack Obama, Donald Trump, and now Joe Biden. That’s 5, and only 11 more to go. Of course there’s the chance of early impeachment. But let’s assume everyone serves their full term.
I’m 25 now. So, I’ve already seen almost a third of the presidents I will see in my lifetime.
Summer vacations
If I live till 90, I have another 65 summers to go. 65 summer vacations left.
If I settle down by 35, I have 10 more summer vacations left – entirely free from constraints and in my prime. I can go skydiving and play extreme sports, without having to worry about seeing the chiropractor. And I imagine, like many others out there, I have more than 10 summer vacation spots I want to hit, excluding the ones I want to have repeat visits to. I already wish I had more time.
Times I’m wrong
In preparing for this essay, for the past week, I tracked the number of times I realized I was wrong. Racking the numbers up each day for seven days. From getting the weather wrong to forgetting what I thought we had for leftovers to being one digit off on my recollection of industry metrics during a meeting, I make on average two small mistakes a day. Extrapolating that to the rest of my life, I have almost 47,500 more small mistakes left to make. I’ve never felt more human than I do now.
Of course, the above number doesn’t include all the times I’ve realized I was wrong after the fact, which I imagine accounts for a mountain of imperfections in its own right. Enough to rival the Great Pacific Garbage Patch.
Idea journals
Many of you reading this blog are no stranger to my idea journals. I go through a journal every four months. I have almost 200 more idea journals to go through, assuming I keep at the pace I’m going at now. 195, to be exact. Oh wow, I really need to invest in some shelf space in my future homes. Enough for over 20,000 pages and all hardcover leather-bound journals.
Breakdowns
Each time I conquer a mental breakdown I think I’d be more resilient. In many ways, I am right. In many more, I am still unprepared for what is to come. Just as the sun rises, I too will cognitively readjust to my stress levels. While I wouldn’t describe my breakdowns to be on regular intervals, on average, it seems to happen once every five years. At least a major one, discounting all the smaller frustrating moments I come across. That’s 18 total, and 13 more mental shifts I won’t be ready for no matter how much I prepare.
In closing
All the above calculations were in the scope of 90 years old. But the awesome part is if I live past 90, every day will be icing on the cake. It’ll be better bang for my buck!
The point of this mental shift isn’t to be 100% accurate (’cause I know I’ve made quite a few generalizations). But rather reframe how we choose to live our lives.
In comparison with the hundreds of thousands of years the human species has lived, we are mere century inhabitants. And in the whole history of Earth, if we were to count on a 24-hour clock where the formation of Earth began at time 00:00:00, humans have lived just over a minute. We have short lives. Maybe that’ll change some time in our lifetime, with technology, CRISPR, or some sci-fi derivation.
But that doesn’t mean we can’t live fulfilling lives. Or as Garry Tanputs it, most people are “short term optimists” and “long term pessimists” and end up picking smaller problems to tackle. Rather, we gotta be “short term pessimists” and “long term optimists.” We have short lives, but let’s live a life where our impact lasts beyond our physical lifespan.
#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!
For any content creator, like myself, it’s incredibly easy to bifurcate ourselves along two paths.
Everything you create is going to change the world. I am important.
Nothing you create has any impact on the world around you. I carry no value.
Some voices over time have profound power on society. They hold the capacity to elicit widespread mimetic behavior. And many an author have snowballed down this thesis – for better or worse. There’s a saying that goes: You’re never as good as they say you are; you’re also never as bad as they say you are. Or maybe that was just a paraphrase of Lou Holtz‘s line: “You’re never as good as everyone tells you when you win, and you’re never as bad as they say when you lose.”
So, the flip side, the rise of citizen journalism has led more and more people to share transient perspectives of themselves or of the world in the form of social content. With the occasional goal of turning such fleeting outlooks into enduring memorabilia. Be it through Medium or TikTok, Substack or Instagram, YouTube or Clubhouse. A blog like this or a podcast. Yet when zooming out, we see the incremental impact of each additional voice is often drowned in the noise that populates the 21st century internet.
The truth, really, is somewhere in the middle. Where exactly? I don’t know. And frankly, it’s different for each genre and speaker out there.
Yet that doesn’t mean we should stop. At least for me, in knowing that I have positively impacted just one person’s life in a meaningful way is enough of a reason to continue. And if there’s a ripple effect beyond myself, then I am steps closer to having a life worth beyond a single century.
Brian Armstrong of Coinbase recently wrote via a blogpost. “The tools for distribution have become democratized, and every company can become a source of truth.” In a similar way, each individual – a company of one, a solopreneur in her/his own right – can become a source of truth. Each individual is a platform for the story we ourselves want to tell that isn’t misinformed or misaligned with post-production and traditional media incentives. Of course, it’s still up to us to have a head above two shoulders. Every individual can become a source of truth. But that doesn’t mean every individual is a source of truth. It’s up to our own judgment to think critically and act accordingly.
But let’s be honest. What I write isn’t journalism. It’s just a formulation of opinions and anecdotal observations over the course of time. While I try to approach my content from as much of an unbiased and informed perspective as possible, reality is I’m still missing something. In many ways, each of you is learning how I learn as I learn. Or maybe you’re already two steps ahead.
#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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Many of my friends are no stranger to the ephemeral nature of my creative outbursts. Some of these ideas are whimsical in nature. Where, from the start, they carried no real weight behind their punch. A deplorable few collected dust in the attic, as a product of giving myself the time to think twice. To second-guess myself. In fact, partly due to being in VC, I became quite proficient at saying “No.” I was so good at saying “No” that I forgot how to say “Yes”. And as I wrote before, the theme of this year is to say “Yes” to more opportunities to experience growing pains. So, when my friend brought up something she used to track things she repeatedly says “Yes”, then “No” to, I was intrigued. She called it her fickle jar. And of course, I had to ask.
Both she and I share common ground. In the sense, that we happen to be promiscuous when it comes to ideas. We mint and host a multitude of ideas. But often don’t give most of our thoughts a double take before we abandon them. They retire from our lips before they have an opportunity to marinate in our minds.
So both of us needed this fickle jar. The fickle jar is a jar chronicling everything you might be fickle on. Soft commitments of “I should do X.” Or “It’d be cool to do Y”. It’s a visualization of the loose promises you make to yourself. Every time you think of a something you want to or should do, write it down. Draw it in its own bubble. Each idea isolated from the next – though some might be related. And each time you follow through and act on the idea, you color your bubble in. When you finish a jar, make another one. Over time, you can visually see what your creativity to commitment ratio is.
Over the next few months to years, I know I’ll accumulate enough fickle jars to have my own fermentation station in my basement. The goal of all of this is to visually track my partiality between creativity and commitment. But moreover, to emphasize intentionality. In the event I propose an idea – which is inevitable – it’s not a fleeting thought. And those of a less ephemeral nature, I take it and give it a go, regardless of the outcome. Hesitation has always been the enemy of my progress. Ideally, over time, I commit to most ideas that spring up. But realistically, I know it isn’t possible. Neither should it be a priority.
Yesterday morning, I was reading First Round’s interview with Irving Fain, co-founder of Bowery Farming, who recently announced their $300M Series C round. While not your first-time founder, having built CrowdTwist (acq. Oracle) and iHeartRadio, with Bowery, he, nevertheless, jumped into an industry he knew little about.
“I could sit on a chair and think my way around this problem for another decade, but when building a company, you never avoid that moment where you have to jump off the cliff. In some respects, what you want to try to make the cliff-to-ground ratio as small as you can. But there is no amount of work and research that avoids the fact that at some point you’re jumping off into the abyss.” So like Irving, I need to have the nerve to jump into the abyss – at least more so than the status quo. I just have to say “yes” to the genre of ideas that have historically left me in decision paralysis.
Fain goes on to say, “Before I started my first company, I spent enormous amounts of time evaluating, evaluating, evaluating, saying no, and evaluating, evaluating, evaluating, and saying no. And in hindsight, I look back and say, ‘Wow, I said no to some great ideas.’ I spent way too much time getting to the wrong answer, arguably.”
I recently realized that some of the biggest risks I ended up taking is spending undue time amidst inaction. The risk is the opportunity cost of the time I could be spending elsewhere. Yet I choose indecision – an infertile stalemate. Crops won’t grow if the soil hasn’t been tilled.
She also noted, “Fickle also rhymes with pickle.”
Ironically, this essay almost became a fickle pickle ’cause I was too lazy to transcribe my fickle jar.
#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!
The amazing Paul “PG” Graham came out with an essay this month on crazy new ideas. And the thing I’ve learned over the years, being in Silicon Valley, is if PG writes, you read. In it, one section in particular stood out:
“Most implausible-sounding ideas are in fact bad and could be safely dismissed. But not when they’re proposed by reasonable domain experts. If the person proposing the idea is reasonable, then they know how implausible it sounds. And yet they’re proposing it anyway. That suggests they know something you don’t. And if they have deep domain expertise, that’s probably the source of it.
“Such ideas are not merely unsafe to dismiss, but disproportionately likely to be interesting.”
I’ve written a number of essays about crazy ideas. Here. Also here. The last of which you’ll need to Ctrl F “crazy”, if you don’t want to read through all of it. And also, most recently, here. But that’s besides the point. The common theme between all of these is that crazy ideas are not hard to come by. Crazy good ideas are. Good implies that you’re right when everyone else thinks you’re crazy. When you’re in the minority. And the smaller of the minority you are in, the greater the margin on the upside. Potential upside, to be fair.
As investors, we hear crazy pitches every so often. David Cowan at Bessemer even wrote a satire on it all. For the crazy pitches, go to episode five. The question is: How do we differentiate the crazy ideas from the crazy good ideas? But as PG says, if it’s coming from someone we know is a subject-matter expert (SME) and they’re usually grounded on logic and reasoning, then we spend time listening. Asking questions. And listening. ‘Cause they most likely know something we don’t.
That was true for Brian Armstrong, who recently brought his company, Coinbase, public. He worked on fraud detection for Airbnb in its early days prior. And he knew he was getting into the deep end with crypto back in 2012. But he realized how unscalable crypto transactions were and how frustrated he was. Garry Tan, then at YC and part-time at Initialized, saw exactly that in him. A reasonable SME with a crazy idea. Garry just released an amazing interview between him and Brian too, if you want to tune into the full story.
What if some of the variables in the equation are missing?
But most of the time the founders you’re talking to aren’t subject-matter experts with deep domain expertise. Or at least, they haven’t left an online breadcrumb trail of whether they’re a thought leader or if they’re reasonable human beings. So subsequently, in the little time I have with founders in a first or second meeting, I look for proxies.
For proxies on domain expertise, I go back to first principles. What are the underlying assumptions you are making? Why are they true? How did you arrive at them? What are the growing trends (i.e. market, economic, social, tech, etc.) that have primed your startup to succeed in the market? Does timing work out?
To see if they’re “reasonable” under PG’s definition, I seek creative conflict. How do you disagree with people? If I brought in a contrarian opinion you don’t agree with, how do you enlighten me? How do you disagree with your co-founders?
In closing
To be fair, we’re not always right. In fact, we’re rarely right. On average, in a hypothetical portfolio of 10 startups, five to six go to zero. One to two break even. Another one to two make a 2-3x on investment. That is to say, they return to the investor $2-3 for every $1 invested. And hopefully, one, just one, kills it, and becomes that fund returner. Fund returner – what we call an investment that returns the whole fund and maybe more. Of course, every time a VC invests, they’re aiming for the fences every time. As a VC once told me, “it’s not about the batting average but the magnitude of the home runs you hit.” And even in those 10 investments, it’s a stretch to say that all of them are “crazy” ideas.
But the hope is that even if we’re wrong on the idea, we’re right on the people.
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I recently came across the above quote – the attribution to Einstein. And I found it extremely prescient. In the world last year. And in the years ahead.
Creativity is the ability to find inner peace in a busy world. To weave cacophony into symphony. The ability to recognize and chart patterns between the pixels and decibels around us. A guiding, focusing, and metaphorical – and I mean metaphorical in its truest form – principle that abstracts you from the literal shackles of your current situation. Now before I get to abstract…
I’ve written about where I find my inspiration on numerousoccasions, including while I’m:
Exercising
Driving
Cooking
Showering
Listening to podcasts
Washing the dishes
… just to name a few. In each of the above, I give myself the intellectual bandwidth and the time to ponder. Simply ponder. With no goal or predestination in mind. Frankly, this blog is a product of such intellectual adventures.
And I know I’m not alone. In the world coming out of the pandemic, this may cause a new revolution of creativity.
Our grassroots
Hundreds of thousands of years ago, we transitioned from a nomadic to a more specialized lifestyle. The transition to specialized roles in a hunter-gatherer society allowed hominids to share the responsibility of survival. As we learn in the basics of economics, economies that have comparative advantages who trade can create a larger global supply of goods and services. In this case, it was the cooperation among the citizens of the same society that freed individuals’ bandwidths to explore other interests, including, but not limited to:
Controlled use of fire
Adaptability to colder climates
Specialized hunting tools, like fishhooks, bow and arrows, harpoons and bone and ivory needles
Intricate knowledge of edible plants
While hand-built shelters likely go as far back as 400,000 years ago, and huts made of wood, rock and bone as far back as 50,000 years ago, it wasn’t until the Neolithic Revolution that agricultural culture became a permanent habitual change. In the emergence of an agricultural lifestyle, humans now freed up time they would have otherwise spent on migration or hunting. And with that same free time, they invented more creative means of living, not just survival, like the means to combat disease and increased agricultural knowledge. Economists Douglass North and Robert Paul Thomas call this Neolithic Revolution the “first economic revolution“. The two state this was the result of “a decline in the productivity of labour in hunting, a rise in the productivity of labour in agriculture, or [an] … expansion of the size of the labour-force”.
Maslow’s Hierarchy
If we look at Maslow’s Hierarchy of Needs, the evolution of free time, and therefore creativity, makes complete sense. Psychologist Abraham Maslowwrote in 1943 that humans make decisions motivated five tiers of psychological needs.
Maslow’s Hierarchy of Needs
A person’s most basic, tangible needs are at the bottom, whereas the intangibles reside at the top. And according to Maslow, you cannot begin to fathom the higher echelons of your needs, like esteem and self-actualization, until you’ve fulfilled the tiers underneath. Maslow also calls self-actualization “growth needs” and the lower tiers “deficiency needs”. In a very real sense, when you’re struggling to find food and shelter or job security, you don’t have the mental capacity or free time to entertain how high your potential can go. Time, specifically leisure time, is a luxury for people who have fulfilled all their deficiency needs. And that leisure time is what creatives need.
Asking the best
Of course if I was to write anything on creativity, I had to ask my buddy, DJ Welch (IG, LI) – one of the most creative minds I know. Not only did he grow his YouTube channel to 370,000 subscribers in less than three years, he was also an artist for Lucasfilm, Instagram, Cartoon Network and more. Now, he’s working on a new project – Primoral Descent – one that I’ve been excited for the public to finally see.
“As a child, my parents let me have a lot of free time. They let me make my own choices. They let me be imaginative. That’s when you come up with innovation. Creativity is a river above everyone’s head.”
When I asked him to unpack that, he said, “Good ideas are gifts from the universe – fish that swim in that river. All you have to do is learn how to reach up and fish for them. And just like fishing, if you stick around long enough – if you’re patient enough, you’ll be able to catch a few. But you never know what fish you’ll reel in. Just that you will.”
Toys for adults
We see the same with entrepreneurs and creatives. They have time to think. Time to reach into that river and pull out an idea. They are investors and the medium of investment is their time. In fact, you can argue they’ve dedicated almost every waking hour to optimize themselves to offer a creative solution or perspective into the market. They’ve made it their job to be innovative. After all, innovation, by definition, is a creative solution. Under Einstein’s definition, we could call them professional time wasters.
As Chris Dixonsays, “The next big thing will start out looking like a toy.” Today, we see the rise of NFTs, VR/AR, content creation, e-sports, and much more. Not too long ago, we had the telephone, and eventually the smartphone, as well as the internet. All of which had their origins as toys. And I know I’m only scratching the surface here. In order to have time to create toys, or for that matter, even play with toys, you need leisure time.
With that same time, more and more people are pursuing their interests and passions, creating, what Li Jin at Atelier Ventures dubbed, the “passion economy“. Similarly, more people are dabbling into new hobbies. In the pandemic, the average person saved 28 minutes of time that would have been spent on going to work. An hour on average for the round trip. Some people used that time saved to get more work done. Others used their time saved to discover new passions – be it baking, starting a podcast, hiking, or gaming. For many Americans, that extra time was paired with stimulus checks and communities coming together to cause political and economic shifts – for better or worse.
As Tal Shachar, former Chief Digital Officer at Immortals, said, “The next big thing in 2021 is the YOLO economy. Consumers will be more open to trying new products/services and spending on novel experiences, particularly with friends, as we emerge from the pandemic with pent up demand and few routines.” In the process of trying, you will inevitably uncover more surface area to expand on.
In closing
In 2021 and onwards, as entrepreneurship and solo-preneurship lowers its barriers to entry, we’re lowering the Gini Index equivalent for creativity. More people will have increased access to time – time to self-actualize. Time to challenge our status quo.
I love this line in Kevin Kelly‘s “99 Additional Bits of Unsolicited Advice“: “The greatest rewards come from working on something that nobody has a name for. If you possibly can, work where there are no words for what you do.” If you can succinctly describe what you’re working on, then you’re not really pushing the envelope.
Later in that same essay, Kelly writes, “A multitude of bad ideas is necessary for one good idea.” And to have ideas, you need time. As DJ and I were wrapping up our conversation, I asked, “So, DJ, how do you optimize for creative moments?”
And he responded with some great food for thought. “I nap. Sleeping is how I process information. As I go lay down for a nap, right in that lucid moment, I come up with my ideas. I quickly scribble them down, then go back to sleep. When I finally wake up, I go work on them. The great Winston Churchill’s naps were a non-negotiable part of his day. In fact, during WWII, he had a bed set up in the War Rooms so he could take his daily afternoon naps. Similarly, I often take 20-minute power naps around 2-3PM. And I’ve never pulled all-nighters. Thinking isn’t hard for me. Thinking is the part ‘efficient people’ [who work straight through the day] get stuck on.”
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“Is your opening bid to assume trust – to assume someone is trustworthy – and to grant them the full benefits of that? Or is your opening bid to not trust, but the trust can be earned?”
Over the past weekend, my friend shared this brilliant interview between Jim Collins and Shane Parrish at Farnam Street. The same friend who recommended this podcast that catalyzed my essay on how to think like an LP. So, needless to say, when she sent me this one, I had to tune in. I’ve been a big fan of Jim for a long time, ever since one of my favorite college professors recommended that I read Good to Great. He has an amazing talent with wordsmithing – bringing seemingly incongruous concepts together in analogous harmony. So when Jim uttered the above quote, I took my Staedtler pen and 180 g/m2 paper out.
“Have you ever considered the possibility?”
Jim also shared, “Brutal fact: Not everyone is trustworthy. And the brutal fact is that some people abuse that trust.” Some people will abuse that trust. Some people will really let you down. But that, in my opinion, as well as Bill Lazier’s – Jim Collins’ mentor, is just the cost of living. That shouldn’t change your disposition in the world, but rather illustrate how much more you should cherish the ones that are trustworthy.
Jim furthered that notion with another anecdote from his mentor, Bill. “Have you ever considered the possibility, Jim, that your opening bid affects how people behave? If you trust people, you’re more likely that they will act in a trustworthy way. So it’s a double win. It’s the best people and they’ll behave in a trustworthy way. The flip side is if you have an opening bid of mistrust, the best people will not be attracted to that. If you have an opening sense of you have to earn my trust, […] some of the best people are gonna be like ‘I don’t need to put up with that. I’ll go do something else.'”
Thinking aloud
Coincidentally, a few weekends ago, one of my good friends hosted a thought lounge. The first I’ve participated after hearing about it for a few years. The purpose of which, and I quote, “is meant to be a place where passionate people come together to practice dialogue and have meaningful conversations.” Every person brings in a topic that’s designed to spark kinetic intellectual energy that each lasts for 12 minutes. And where “creative conflict” is encouraged.
It just so happens that one of the four topics that came up that day was the law of attraction. A concept that states that similar people attract each other. And that one’s thoughts can attract similar results. The more you think you will succeed, the more likely you are to succeed. And likewise the same might be true for failing. One of my fellow participants brought up a great Henry Ford quote: “Whether you think you can, or you think you can’t – you’re right.”
And it acutely reminds me of a story I once read in Tim Ferriss’ Tribe of Mentors. Robert Rodriguez, who directed one of my childhood favorite franchises Spy Kids, shared with Tim when asked the question, “If you could have a gigantic billboard anywhere with anything on it, what would it say and why?”
“I like the idea of setting impossible challenges and, with one word, making it sound doable, because then it suddenly is. So I’d choose FÁCIL! for my billboard. It’s a good reminder that anything can be done, with relative ease and less stress, if you have the right mindset. […] Attitude comes first.”
In closing
“Is your opening bid to assume trust – to assume someone is trustworthy – and to grant them the full benefits of that?”
That’s the line I need on my fortune cookie. If one day I unwittingly become a foolhardy skeptic, I want to open up a fortune cookie after a lonely meal I’ve stuffed myself to the brim on. On a quiet late night Uber ride home, thinking I’ve eaten all I can eat… I want to read that line.
My opening bid is trust. It always has been. And I hope it always will be. I know that people have taken advantage of my kindness and trust. And I know there will be more that will in the future. But I hope I never lose the optimism in my eyes.
#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!
