One of my favorite frameworks of thinking about building and breaking habits comes in the words of Elliot Berkman, whom I’ve cited before. He notes that there are three factors to breaking a habit.
The availability of an alternative habit
Strength of motivation to change
Mental and physical ability to break the habit
Of particular note is the second one. The strength of motivation to change. Change is inevitable. But real change is always compelling. There must be a strong enough desire to relieve yourself of the status quo. John C. Maxwell once said, “People change in four different seasons… People change when they hurt enough they have to, when they see enough they’re inspired to, when they learn enough that they want to, and when they receive enough that they’re able to.”
In each of those seasons, the person is compelled to do something outside of their ordinary flow of time. But there’s another interesting way to think about change. One where you have no choice but to.
CIA veteran Richards Heueronce wrote, “When faced with a major paradigm shift, analysts who know the most about a subject have the most to unlearn.” If there’s anything we can gather from historical records, major paradigm shifts are happening every decade (and less) whether we want to or not. On a macro scale, new technologies, like generative AI, the smartphone, and the internet, as well as political and financial eras, like the GFC, the dot com burst, and wars that affect the increasingly interconnected world. On a micro scale, when we go to college, get our first job, start our first company, raise a family, or buy your first house.
At each stage, the more entrenched you are in the behavioral patterns of the status quo, the harder it is to adjust with the next shift. For instance, as a founder, anchoring yourself on 2020-2021 multiples and valuations won’t help you in the world forward. As an investor, anchoring on the past 3-4 years of markups without fully accounting for the current climate won’t help you with your next raise. Anecdotally, I’ve heard great multi-fund managers mark their portfolio down by 25% already before the market verdict comes in. Moreover, jobs are going to look very different in an age of AGI (artificial general intelligence). Just like with the industrial revolution, new jobs will be created. And I can go on on and on. But I digress.
There’s a hero’s arc in each inflection point. Every time the second derivative goes from negative to positive. The way Viola Davis puts it that that at the end of every hero’s journey, you come face-to-face with not a god, but yourself. And that is when the magic happens.
“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”
#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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
This past Wednesday, I was having lunch with an artist-turned-VC. And as you might imagine, we had to cover every topic at the intersection of art and startup investing. But of all the ground we covered, one stood out — content creation.
She’s on the Gram, LinkedIn, and everything in between. (Although surprisingly not on Twitter.) But to help her focus, she uninstalls those apps on her phone. Otherwise, she says she’ll end up “doomscrolling.” I get it. In fact, many of my friends and colleagues have shared similar things as well. But…
I’m weird. At least among my friend group, I’m really weird. I’m terrible at social media. I’m an 80-year old stuck in a 27-year old body. At least on the social media front. I find it so hard to keep my attention on social. In fact, I schedule ten minutes three times a week to hold myself accountable to be on LinkedIn and Twitter.
So, when it came to sharing my thoughts and learnings publicly, it was a pretty easy decision. Of course, I eventually came to self-rationalize it as the ability to own my own piece of virtual real estate, but there are three more reasons I chose blogging rather than tweeting or social posting.
1. I write to think
I’ve written about this before so I won’t elaborate in length on my own rationale here, but share a few examples of others also holding it in high regard.
There’s only so much you can flush out in just 280 characters, or over any short post. And while some of my thoughts fully flushed out may only be that long or less, not having that restriction gives me peace of mind to not hold back.
One of my favorite George Orwell lines happens to be: “If people cannot write well, they cannot think well. And if they cannot think well, others will do their thinking for them.”
On that same wavelength on writing, Jeff Bezos makes Amazon execs write six-page memos. In most companies, team members often resort to PowerPoint presentations. Take anywhere between five and ten slides. Maybe less, maybe more. It’s much less thought out than a six-page dissertation. As Bezos says, “The reason writing a ‘good’ four page memo is harder than ‘writing’ a 20-page PowerPoint is because the narrative structure of a good memo forces better thought and better understanding of what’s more important than what.”
Equally so, it’s the same reason the best investors write memos for their investment decisions. My favorite public ones are Bessemer’s, which encapsulates much of their thinking at the time in amber. Turner Novak also turned his ability to write great memos to eventually raising his fund, Banana Capital. And the great Brian Rumao writes memos not just pre-investment, but also in his post-mortems where he gathers his learnings.
While I won’t go as far as to comparing myself to the afore-mentioned, I do find great pleasure and great learning from putting words on paper.
2. Longer feedback loop
My writing is more often a form of self-expression, self-curiosity, and self-discovery. So, unlike a product manager or founder who’s relentlessly testing and iterating on feedback, I enjoy longer feedback loops. I may start another content engine at some point that is for a particular audience, focused on feedback and iteration. But this humble piece of virtual estate will stay me. With no algorithm conditioning my attention span and yearn for external validation. That’s not to say I won’t ever (or have not ever) written things that you my awesome readers want, but it is only at the intersection of what you want and the what I enjoy writing about and asking others about that mint content here.
I also spend a lot of time thinking about audience capture, a term Gurwinder brought to my attention in an essay he wrote about Nikocado Avocado, which I also touched on in an essay I wrote near the end of last year.
I’m reminded by something Gurwinderwrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:
“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”
3. The impermanence of social media
Most things on social media are ephemeral in nature. It’s designed to capture the moment, but not chronicle the moments. On Twitter, you can only pin one tweet. On Instagram, you can pin three. And on LinkedIn, only three are visible on the featured carousel, and include, five max before it takes you down another layer of friction to discover more.
There’s a level of impermanence which makes thoughts feel whimsical rather than evergreen. To use a phrase I recently heard Tim Ferriss use, the “durability of the signal seems to wane so quickly.” And that made my thoughts feel cheap.
That’s not to say every post I write has their weight in gold, but the searchability and the evergreen nature of my favorite blogposts (saved in my “About” tab) are the reasons I keep most of my thoughts here.
#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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”
In the world post-pandemic, people crave connection. A desire to go from URL to IRL. Everyone lost those years. Something everyone from a first grader to a college student to a young professional entering the workforce to a retiree could relate to. And in 2021, there was a re-emergence of events. Well-intentioned and well-founded. We had conferences, coffee chats, happy hours, fireside chats, oh, so many happy hours, panels, tech weeks, and… did I mention happy hours?
Most events out there are a time and a place for a collection of people. They’re static points in time. Not even counting the full spectrum of event planners, many of the best event planners spend tons of times on what makes events special, but change more about the small bells and whistles of an event than the overall flow. There are very few who take leaps of faith. Even less true for the vast majority of events, where events feel more of an afterthought than something that is designed to start or end a chapter in your life.
As such, everyone found themselves left with a goodie bag including a surplus of events, a lack of focus and attention, and a lollipop of exhaustion.
So, I had a thought last year, greatly inspired by my team at On Deck Angels. Instead of trying to host an event a month, what would need to change if we could only do one event a year? What would we have to do? Hell, extrapolating further, what if we only did one event every two years? Three years? Every Olympic arc? Which led to the thinking around, what do we need to do to make this the most memorable event that anyone has ever been to.
You see, I’ve hosted and co-hosted small and large-scale social experiments, but it was always for an audience who proactively and voluntarily signed up for. They were willing to do things outside the ordinary. But could I apply the same learnings to events for really, busy people who crave intellectual challenges, and who have been to so many events, they might be jaded?
So, below was and continues to be my collection of governing thoughts around answering that question, which will only grow and refine this year. In the theme of my blogpost last week, the below may be messy. Disorganized. Chaotic, even. Hope not, but possible. You’ve been warned. But I do hope that you might find at least one of the below frameworks useful.
Metrics for success
Every event needs a North Star. When planning the Angel Forum, as well as future events, below are mine.
Attendees go on a hero’s journey, revisiting Viola Davis’ words above. In other words, character development. The event should create opportunities for growth within the event itself.
Every attendee continues to and is motivated to build friendships (as opposed to networking and purely transactional connection) after the event. If the event itself is the only reason for people to connect, but it does not give people incentive to after, it’s a failure (in my books).
For now, that means, not only the speakers and the presenters need to be curated, but also each and every person on the guest list. I have yet to figure out how to customize such experiences at scale, where each person has wildly different goals.
Narrative frameworks I use for events
To dig a level deeper, here are my frameworks for execution:
Surprise and suspense — Surprise is when you relay information that the audience does not expect. Suspense is when you relay information that the audience is expecting, but does not know when it’ll drop. Suspense is how you keep attention. It raises expectation, but knowing when to deliver the news helps with creating a reality that meets or beats expectation. Surprise is, on the other hand, purely for creating alphas in this expectation-versus-reality model. It’s the main driver for overdelivering on a seemingly smaller, but still powerful promise. To do so, I find George Loewenstein’s 1994 paper on the psychology of curiosity super helpful. More on how the five triggers to curiosity influenced my thinking here.
Candy versus the meal — A Malcolm Gladwell framework. Effectively, how people think and what people actually talk about are quite different. Candy is what people talk about. For example, if I were to talk about the recent Avatar movie, I’d talk about how amazing the motion capture and the CGI was. And in doing so, I’ve spoiled nothing. It tells you nothing about the plot, but it’s exciting to talk about. On the other hand, the meal is how people think. It’s the whole package, the whole story. The meal has to be well-worth the visit, but the candy is what gets people excited. More on that in a previous essay I wrote here.
The audience must understand the rules of magic — This is a combination of the thoughts of Malcolm Gladwell‘s framework around tools and Brandon Sanderson’s three laws of magical systems. Give the audience tools to use at the very beginning of the event. It could be a framework for how to think about the event and every activity in between. It could be physical tools that they will employ throughout the event. And once you do, make sure your audience knows how to use those tools. Test them. Give them small, but easy case studies and questions. Make it easy. Don’t put them on the spot. And by completing that test, that satisfaction and joy will help motivate them to use it more later. As Sanderson’s first law of magic goes, “your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” More on my thoughts on Sanderson’s laws here.
Plots — Like any good story, the narrative is governed by plots. The plot must thicken and build towards a climax. And it must be resolved by the end of the event. Leave little in the main plot to chance, but leave room for each guest to discover something extraordinary. Maintaining a minor amount of stress and uncertainty, while sharing examples and reminders of being open-minded to new experiences, goes a long way. Only after stepping outside one’s comfort zone can one grow.
Always use the audience’s time in a way that does not feel wasted — Inspired by one of the greatest writers of all time, Kurt Vonnegut. I forget which lecture he did that I learned this from. But it’s always been a governing theme for what I do.
End on an ending where the reader can imagine no other — No loose ends. Everything that is teased (whether the audience realizes it or not) needs to be resolved by the end. This might be a semi-controversial opinion among storytellers and creative professionals. But I’m biased. I like my stories to end with a bowtie.
In closing
As you might imagine, much of this is still incomplete. And I hope to share more as I continue down this path of exploration and discovery.
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
“If you look at all big human achievements, like flying to the moon, for instance, it’s all based on large scale cooperation. How did humans get to the moon? It wasn’t Neil Armstrong flying there by himself. There were millions of people cooperating to build the spaceship, to do the math, to provide the food, to provide the special clothing, and the funding.
“The big question becomes: why are we capable of cooperating on such a large scale when chimpanzees or elephants or pigs can’t?
“It’s the ability to invent and believe fictional stories.”
For any big achievement, and I’m specifically reminded of the recent news with FTX — for FTX to get as large as it did at its peak — it was a monumental achievement. It was the work of many, rather than a single individual. It was the result of many buying into this narrative that Sam Bankman-Fried shared. That includes his team. His customers. His investors, from Sequoia to Tiger to Softbank to Coinbase. Many of whom are smart people who gave into the velocity of the market the last two years.
Source: Sequoia article on FTX While I’m not sure how I feel about founders playing games during the meeting, I can’t deny the vision isn’t compelling.
To be fair, and this is not to condone the wrongdoings of the FTX team, every founder’s job is to distort reality. To put the human race on a fast track towards a future that is non-fiction to the founder, but fiction to everyone else. A world that isn’t false, but has yet to come. As author William Gibson once said, “The future is already here — it’s just not evenly distributed.”
I also love the thesis of Alexia‘s fund, Dream Machine. We make science fiction non-fiction.
Founders pitch their answer to: What will the world look like? Investors, customers, and talent then make bets with their time and money on which future they would like to see happen and the likelihood of it happening.
FTX is no exception. The fine line is when a founder does get creative, it is imperative for them to have a moral compass, which seems like SBF didn’t have. And of the million and one things they’ve done wrong (no board, giving loans using customer money, fraud, etc. and some more that are more questionable in nature, like political donations, etc. — none of which from what little I know are things I would ever endorse), I have to say they nailed their marketing and messaging. They got a lot of people excited about it fast. It’s easier to get people excited about the future of money than the future of fintech or the future of crypto.
The past week has been an insane week for crypto, namely when FTX filed for bankruptcy. And while there are many different angles to it, I took it upon myself to revisit a podcast episode from two months back where Nathaniel Whittemore, FTX’s former Head of Marketing, shared his marketing insights. Namely, around their 2021 Super Bowl ad.
A Super Bowl ad two years since its founding date. If nothing else, that’s impressive. Moreover, they got Larry David who has been known to never appear on ads to do it for them.
But what I found to be very powerful is Nathaniel breaks down why they chose to do a Super Bowl ad in the first place:
“People always focus on how much [an ad] costs. ‘This ad costs X.’ Which in a vacuum seems so high. […] What I think that analysis doesn’t take into consideration:
“The number of people actually watching those ads. If you’re gonna get X people with an ad that costs a $100,000, but then, 50x that with an ad that costs $5 million, that’s the same ratio.
“But the more important piece is that at least in America, the Super Bowl is the literal one moment each year that people not only are not annoyed with ads, but it is an active part of the experience that they’re having and they’re excited.”
He also does caveat that it doesn’t mean a Super Bowl is good for every kind of marketing campaign. But more so for brand-building, as opposed to product marketing or lead gen.
To echo that, David Sacks wrote a great piece on the importance of having an operating philosophy which I’ve referenced on this blog before. In it, he finds it incredibly powerful for companies to aggregate product updates and marketing campaigns in four big “lightning strikes” (each quarter) rather than have tidbits of information floating around every week.
Of course, companies like Twitch, Salesforce, Apple, and Google have taken it a step further by having a large launch event once a year. As Sacks mentions, “It’s not just about the external marketing value. There’s a huge internal benefit from setting dates and deadlines in order to hit a public launch.” It drives excitement and a narrative that both customers and future customers, as well as team members can get behind. The world is waiting. Your team is shooting to meet and beat expectations. And that’s incredibly motivating.
What does this mean for the crypto narrative?
A friend who took a hit from the recent series of events asked me at dinner last night, “What does this mean for crypto?”
Of which I think Yuval does a better job explaining it than I could. In the same podcast episode, he explains, “Not everybody believes in the same god or in any god. But everybody believes in money. And if you think about it, it’s strange because no other animal even knows that money exists. If you give a pig an apple in one hand and a pile of a million dollars in the other hand, the pig would obviously choose the apple. And the chimpanzee the same. And the elephant.
“Nobody, besides us, knows something like money exists in the world. The value of money doesn’t come from the paper. Most of the money in today’s world is not even paper; it’s just electronic data moving between computers. So where’s the value from? It’s from stories we believe.
“We are at risk of the whole thing collapsing. It happens from time to time in history. Inflation to some extent is that. The value of money is not what we were told it is. And inflation can sometimes hit thousands of persons and millions of persons. Eventually, the money becomes worthless.”
I don’t personally believe crypto will become worthless at any predictable point in the future. In fact, I think it has a great future ahead. Just a little early for its time from an infrastructure perspective. But, it is a non-zero possibility. That said, the more institutions, especially larger ones like FTX, that use crypto as the currency of faith, collapses, the more the faith behind the story of crypto will waver. And with repeated bad players, it is a race between mass adoption and the rate faith deteriorates.
For as long as the exchange currency is in dollars, crypto has still yet to be widely adopted. For instance, the value of crypto is pegged as a function of the dollar. As of the day I’m writing this on November 16th, 2022, if you type in bitcoin in Google search, the first search result is that Bitcoin is worth 16,768 US Dollars. In other words, as long as crypto is measured in dollars, the story of the dollar is stronger than that of crypto.
In closing
I’m not here to share my latest scoop or an update on the current situation about FTX. Twitter is filled with these already. Plenty of smart individuals have already covered all the ground I would ever even think about covering. I don’t keep my finger on the pulse of crypto and FTX nearly as much as my friends and colleagues.
Really, the purpose of this blogpost is really my curiosity that in order for FTX to get the notoriety that it has today, the team must have done something really well. And in my eyes, it’s not the product or the business, but the narrative in which they built. So, if someone at HBS or GSB isn’t writing a case study on this, they should.
P.S. Had to pass this to two friends at 6AM this morning to see if this blogpost was even worth publishing. Bless their hearts for their support so early in the morning.
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
“Art is to console those who are broken by life.” — Van Gogh
An investor I deeply respect recently told me, I am “really good” at long-form writing. Admittedly, even writing the sentence just before leaves me just as squirmy as when he first said it. I am of course genuinely grateful for the compliment. But my childhood prevents from fully appreciating and accepting a kind compliment.
Rather than having a practiced eye for structure and prose — which I’m sure the real linguists and writers will have much to critique on my lack thereof… for me, I can’t imagine a world where I can boil down distinct and nuanced thoughts from multiple sources in one tweet. Which could mean three things:
I was never great at writing college apps.
I am terrible at Twitter.
I have trouble saying No to people and options.
Don’t get me wrong. There are many things out there are best expressed simply — that need no further elaboration. My blogposts on 99 pieces of unsolicited advice are examples of such. One for investors. One for founders.
Nevertheless, longer form writing helps me think. My mind is often a mess, and sometimes I wonder how I make it by with a mind that looks like the inside of an average college boy’s dorm room. It is most evidenced when I speak, but least explicit when I write. I have time to mull over thoughts. I have time to realize that not every thought, idea, Eureka! moment is a productive one.
I apologize if I seem smarter than I am. I’m not. I’m just another person looking to learn my way through life. Curious enough to know I am lacking, but confident enough knowing I can get there. When confidence in my self-worth wanes, I find solace and therapy in the letters that I ink on a page.
I’ve shared this analogy a few times with friends. That there are artists. And there are designers. The latter fulfills a need their audience has. The latter creates where the audience is someone other than themselves (while that doesn’t have to be mutually exclusive to building for oneself). For the former, the audience is themselves. It is a form of expression unforgiving to the remarks and views of others. While others may appreciate it, you create for yourself. In a way, the best entrepreneurs start as an artist but end up as a designer. For me, this humble piece of virtual real estate is my art gallery. And a small part of me fears becoming a designer through this blog. I save the design work for other parts of my life.
I’ve been fortunate to have sponsors reach out to support this virtual acreage in the wider, increasingly saturated market of content. As you might have noticed, I’ve turned down everyone so far. Partly because of alignment, but mostly, I’m not yet sure if I want to turn writing into a job. To me, writing is comforting. It’s a sanctuary where I can isolate, even briefly, from the equivalent of noisy San Franciscan streets filled with sirens and honks every minute. And upon receiving payment, I would find myself in debt to someone or some entity. That’s fine if it was an essay or a piece of content I wanted to write anyway. But so far, it hasn’t been. And if it’s not, I find myself enjoying this therapeutic process just a little less.
I’m reminded by something Gurwinderwrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:
“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”
I know many of you came to this blog via the content I write about startups and venture. At least that’s what WordPress tells me. If you came here expecting only that kind of content, I will have to disappoint. And I’m happy to send you recommendations of what I read in that arena. If you came here for that and a little more, I’m excited to share more of my takeaways as I traverse this blue planet. Who knows? Maybe one day beyond.
Nevertheless, I appreciate every one of you for giving me time in your day. Stay tuned!
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
My friends who know me well know I have this concept I call work-work balance. And in sharing it with someone new, it’s usually met with a light chuckle. I never mean it as a joke. But nevertheless, people take it as my attempt to be snarky and witty.
I believe most of you, my readers, are familiar with work-life balance. A lifestyle that balances work and your life outside of work, often one that spends the capital earned though work. When I hear most people say it aloud, its most frequent use case is in avoidance of doing more work. But the underlying principle is that most people don’t enjoy the work they do. Rather, they find their joy and fulfillment in pursuing hobbies and passions outside of the confines of a 9-to-5.
Just like having a work-life balance is a privilege, having a work-work balance is, in my humble opinion, even more so one. Speaking of privilege, earlier this week, I had the fortune of hearing a rather profound line:
“If you do one thing in life that fuels and motivates you, then you should yourself lucky.”
So, in even talking about work-work balance, I admit I came from a position of privilege, but one I do not think is unattainable for those who also have the privilege of debating the technicalities of work-life balance.
Work-work balance is the balance of doing what you love doing with work that you need to do to continue doing what you love doing. To me, work that I enjoy doing — interesting projects — fulfills me. It gives me meaning and purpose in life. To best illustrate this concept, I’m going to have to steal Elizabeth Gilbert‘s line in a 2016 interview with On Being. It’s not the first, and it won’t be the last time I quote her here:
“Everything that is interesting is 90 percent boring.”
When you’re proud to have work be your identity
Starting something — anything that is going to be core to your identity, even if it is only briefly — is going to be unhealthy.
Being a great venture-backed founder is unhealthy. Starting a venture fund from scratch is unhealthy. Being a world-class content creator is unhealthy. Being a diligent and serial author is… well, you get it. Hell, even binge-watching the latest and greatest Netflix show is unhealthy.
It is also the difference between passion and obsession. One keeps you daydreaming; the other keeps you from sleeping.
I’m not advocating that everyone live an unhealthy lifestyle, but that the concept of work-life balance is a lifestyle that doesn’t fit everyone, but those who have not or have yet to find deep fulfillment in the professional aspect of their life. For those who have found their life’s work, work-work balance may be a more sought-after lifestyle. In working mainly with founders and emerging fund managers, their life stories seem to corroborate the previous sentence.
In the world of startups, I often tell founders, and have many a time, advised founders not to take venture capital. There is no shame in creating an great and fulfilling lifestyle business. But as soon as you take venture, that’s a different story. After all, another name for venture capital is impatient capital. It is the perfect permutation of not just ambition, but also of expectation. The greater you raise in venture, the greater the expectation.
A $10 million valuation is not a number indicative of your company value. In fact, I think the 409a valuation does a better job of that than what VCs price your company at. Rather, a $10 million valuation on a social media company is a bet that you have a 0.0025% chance — a 1 in 40,000 chance — that you’ll be as big as Meta. At least at the time of writing this blogpost. Equally so, a $1 billion valuation is a bet on the odds that you have a 1 in 400 chance to grow as big as Meta. As Uncle Ben said, “with great power comes great responsibility.”
And as such, the expectation and the will of your new bosses — your investors — is that you can scale a team that can help you capture that opportunity. And for VCs, or die trying. Many, if not most, great VCs would much rather you bat for the home run than walk a base. After all, the success of an investor is not defined by their batting average but the magnitude of home runs she or he hits. But I digress.
As a founder, you must love your work so much that it’s contagious. That it affects your investors, your team, and your customers. Why? Because in the course of building a rocket ship, there are a million and one things that can go wrong, and a million and two things that feel tedious, repetitive, and slow. And the work you enjoy doing must be so powerful that just the thought of being able to do more of it invigorates you through the long troughs between wins.
I say all this to every founder I’ve met who didn’t fall madly in love with their problem space and who expect venture funding. The going will get tough, and I, like many other investors, want to know that you have the grit to make it through this long, windy journey. Having a good pulse on work-work balance is one of a few proxies for that grit.
Of course, I do want to posit that a work-work balance doesn’t mean you should make prolonged sacrifices to your mental health, your sleep schedule, or your time with friends and family.
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
On the second half of a late summer Friday, as I was overlooking the singed blades of the parched grass in our front yard, I found my good friend, Andrew, in my inbox. An inbox that was about to be empty from filing an eclectic collection of investor updates, food science analyses, tech articles, and my weekly subscription of Substack extraordinaires into my Read Later folder.
An email headline in boldface. All it would take would be two clicks. Two clicks to add to my party of internet writers I would be conversing with over a Saturday morning of roasted hojicha tea. Instead, I clicked once. Just once. And I’m glad I did.
Andrew started writing again. Pen to paper. Or rather, finger to keyboard. And that, that was worth celebrating. I, like many of his other friends, had been starved, deprived, relieved of his prose given his busy schedule. In it, he postulated the relationship between commitment and conviction.
“Commitment helps you stay on the path. Conviction is what calls you to the path in the first place.”
In sum, the pre-requisite for commitment is conviction. And so, it got me thinking about the source of conviction…
From inspiration
For decades, athletes have tried to break the 4-minute mile. According to British author John Bryant, since 1886. “It had become as much a psychological barrier as a physical one. And like an unconquerable mountain, the closer it was approached, the more daunting it seemed.”
But it wasn’t till May 6, 1954, did Roger Bannister break it with a time six-tenths under the mark. As soon as Bannister did it, 46 days later, another did. One year later, three runners broke the once elusive 4-minute barrier in one race.
The thing is, nothing technological had changed in the world when all these runners post-Bannister broke the four minutes. Nutrition hadn’t drastically improved. Neither was there drastic evolution in the technology of shoes. Yoram Wind and Colin Crook argues it was a mindset shift. The impossible was possible.
We see the same notion today in the world of emerging markets. In these markets, the first wave of unicorn founders is usually spearheaded by Harvard and Stanford grads building X for Latam or Y for Africa. For instance, both of Grab’s founders are HBS graduates. Gojek’s Nadiem is no exception. Nubank’s David Velez holds a similar Stanford GSB degree. So does Cabify’s Juan de Antonio. Rappi’s founders are also Stanford alumni. And the list goes on. They come with the Silicon Valley mindset in a market underestimated by not only the broader world but by the homegrown talent themselves. I like the way a Midwest founder-turned-investor once put it, “My mind is in Silicon Valley, but my feet are in the Midwest.” The same is true for this first wave.
And once they’ve proven it’s possible to reach unicorn status, the second wave follows quickly after.
Most people follow in the footsteps of our predecessors. Older siblings are the same for their younger siblings. Parents are that for their children. While I’m not a parent yet myself, I do aspire to be that for my children. Equally so, that’s why we need diverse representation in media, in positions of power, and in stories.
For many, conviction comes from examples to disprove the limitations of our own imagination.
From emotion
For a handful of others, conviction comes from a deep desire to prove or disprove.
When Michael Phelps’ eight gold medals in Beijing were on the line, their coach Bob used what the French team was boasting on the papers as motivation in the locker rooms. “The Americans? We’re going to smash them. That’s what we came here for.” And soon after, the world was blessed with one of the greatest races to date. A race of which the Americans — the underdogs — pulled a miraculous spectacle of conviction and resolve.
For founders, you need obsession, not just passion. Many of the best ones have a personal vendetta — a deep, unquenchable desire borne out of time spent in the idea maze. Every successful founder needs to perform 10-15 miracles in the startup to household name journey. Trials by fire that are meant to deter the fainthearted.
After chatting with a number of limited partners (LPs, folks who invest in venture funds) over the past two months, I’ve realized the thread of founder obsession continues here. That investor-market fit is not just a function of professional experience but also of life experience. Once again, a deep desire to change the world from personal frustrations and the hope that no one will ever have to go through what they went through.
In closing
Earlier this year, Reed Hastingsshared a profound line with the graduating class, “[stories are] about harnessing the human spirit.” Conviction starts from the story we tell ourselves. The story itself is bound by the limitations of our own imagination. And conviction happens to be the belief that we can will our imagination into existence.
Michelangelo once said, “The sculpture is already complete within the marble block, before I start my work. It is already there, I just have to chisel away the superfluous material.” Commitment is the dedication to your conviction. A devotion to say no to distractions and yes to the person you want to be.
We live in a world filled with shiny objects. So, ask yourself, do you want what others want? Or what you truly want? Is your conviction inherited or innate?
I was listening to the latest episode of the All-In podcast, and David Friedberg echoed a similar notion for the greater human race, “What differentiates humans from all other species on Earth is our ability to tell stories. A story is a narrative about something that doesn’t exist. And by telling that narrative, you can create collective belief in something. And then that collective belief drives behavioral change and action in the world.”
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
When I was in New York last week, I had the fortune of catching up with one of my favorite people inside the rustic walls of Il Buco. Needless to say, an hour and a half was not enough to contain months of development and change. So, to continue our tea, the next day, after she met up with the one of the heavyweights in her industry, she asked:
“How do you keep your enthusiasm in check but show it to the extent that shows respect to the person and also have a conversation as equals?”
In sum, how do you fangirl/fanboy without losing your composure?
I don’t. It happens less frequently now, but I still do.
In fact, even when I try not to or attempt to convince my conscious self, this is just another human being doing their best to live the life they want, there’s something that my eyes do without fail every single time. Here’s to hoping it’s not painfully obvious to the other person.
In fairness, I actually don’t know what I look like when it happens. I can just feel and SEE it through my eyes every time. In fact, I don’t even know what this phenomenon is called. Or if there’s a word for it. If I were to describe it, it’d be if the thousand-yard stare and diplopia had a baby.
It’s completely involuntary. All my other senses and cognitions work just fine. And when it happens, I start blinking a lot more which usually recalibrates my gaze.
Physiological response aside, over time, I’ve simmered down my ability to respond into two ways, especially when my brain decides to turn off. One for each situation.
I’m prepared. For instance, this is a scheduled meeting, or I know I will see this person at an upcoming event.
I’m unprepared. The canonical serendipitous elevator ride. For instance, bumping into them at an event. Or true story, we happened to both be helping to carry A/V equipment backstage post-show.
When I’m prepared…
The goal here is to know the other person better than they know themselves at the point in time. This is the same mentality I carry into both conversations in public and private spaces. The former with interviews, fireside chats, and panel discussions. The latter in the form of coffee chats, dinners, happy hours, and the like.
Depending on the timeframe, I come prepared with a different number of questions. But generally, for every 30 minutes, I come with three questions.
The first question is to establish rapport. And it’s always a personal one. I almost never start the conversation with pure “business.” This sets the tone for the rest of the conversation, as well as how candid they will be with you.
You’ll have to do your research. Some may require more digging than others. That said, don’t take it too far by finding their home address or social security number. Here, I usually look for fun facts. Like they did street dancing back in high school or they love going to stand up comedy shows.
If you’re going to take away one thing with this question, it’s to surprise and delight.
For the second one, which is usually the optional question if we’re short on time, I love understanding people’s inflection points. For example, why did they go from consulting to acting? Or from an art gallerist to a VC?
Not just the fact that they went through a massive delta, but I love understanding what they were thinking before, during and after they made the transition. Was it a decision that was supported by their family and/or peers? Was it a difficult decision to make? What got them over the activation energy to commit to this new lifestyle?
The third question is akin to the one I always advise founders to think about when talking to investors. Why would this investor be the best dollar for your cap table? Similarly, even if you’re not raising money, what kind of question can only the person in front of you answer? Or very few others can? It’s usually a function of their work or life experience, where they end up becoming uniquely positioned to talk about that topic.
As a prelude to this last question, I usually preface why this question means a lot to me. Why do I need this answer? Show that you have spent time in the idea maze. Time thinking deeply about the topic already. Naturally, anything that is googleable is off-limits here.
You have one chance to make a great first impression. Don’t waste it.
Cutting it short
Just as it’s important to start the conversation on a high note, in my opinion, it’s even more important to end the conversation on a higher note. As such, I have a three rules of thumb:
Never overstay your welcome. It’s always better to cut the conversation short than to end with awkward silence. Be extremely acute to where the clock is compared to how much time you’ve asked of them.
Have a go-to phrase (or phrases) to end the conversation. One of my favorites is, “As with all great conversations, we ran out of time before we ran out of topics.” (The cat’s out of the bag, so now I need a new one.)
Follow up within 12 hours of the conversation with notes from the conversation, and action items on your end. For instance, if the other person shared advice with you that you solicited, be sure to act on it. Come back two weeks to a month later and share the results of your findings. As you might suspect, bring a pen and paper for the conversation. People really respect it when you take their thoughts seriously. During, and even more so, after.
If possible, pay it forward, and when that time comes, don’t be afraid to share it with the source of the advice.
When I’m unprepared…
While still worthwhile in the former situation, you need to be able to break the ice quickly and give others a reason to listen to you for just two more minutes. People are naturally busy. And if you disrupt their normal flow of life, their whole goal while you are speaking to them is not how they can talk to you more, but about how they can get back to doing what they were doing.
Just as much as you will be unprepared, they will be too. As such, you need to disrupt their flow even momentarily. Your short 10-second bio needs to generate emotion and curiosity. Oftentimes, that is not your title. For instance, one that I like using with folks who I know to be lighthearted and have no context to the startup world is, “I get paid to be the dumbest person in the room.” Self-deprecating humor really does help for folks who can and have time to take a joke.
Other than your short bio, always have 2-3 questions handy via muscle memory that are good to ask in almost any situation AND would give you immense insight. I’ll share one of mine, and likely many more in the future with my DGQ series on this blog.
In your line of work, what differentiates the great from the good? Not just the good from the bad, but how do I tell the very best from the ones that have yet to get there but are still a cut above the rest?
Practice these again and again. In front of a mirror. In the shower. Or while you’re driving. Until they become second nature.
In closing
The important thing to remember is these people don’t owe you anything. And sometimes, while you can’t give them what they want, you can make that amount of time you have with them amusing. Insight doesn’t just come in the form of answers but also questions that get others to think in ways they didn’t before. Going back to one of my favorite Kurt Vonnegut lines:
“Use the time of a total stranger in such a way that he or she will not feel the time was wasted.“
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
I am by no means the best equipped to talk about this topic, nor have I achieved any modicum of success that I can call my life’s work yet. But the beauty about being insatiably curious is that I’ve gotten to know some incredible individuals, like…
Multi-time New York Times best-selling author
Founder of a household corporate brand
Investors who have consistently returned their investors over 10 times their investment
Individuals who have achieved insane, superhuman feats (i.e. climbing Mt. Everest, Olympic medalist, etc.)
Creator of a popular TV show
Chefs will multiple Michelin stars
A mother who serves as the role model for her children
A war refugee turned serial venture-backed founder
A veteran with multiple Purple Hearts
Unfortunately, while this isn’t true for all world-class performers I’ve met — to borrow one of Tim Ferriss’ phrases, many continue to stay curious, studious, restless, and most of all, humble. For those who continue to stay humble, how do they do it? After all, they have every right down to their bone to exhibit a large ego. To be full of themselves. They’ve made it.
What powers their humility? A question I find fascinating and telling of character.
Admittedly, I wish I could’ve been less obtuse about how I asked the above question.
After a number of conversations over the years, there are four chief themes:
Their greatest achievement is still ahead of them. They know what is possible, and continuously seek the adrenaline of doing the impossible. As long as the impossible is ahead of them, they are fighting a war against antiquated, yet widely-adopted mindsets. And the thing with the impossible is that it’s impossible to do it alone.
They fear they are unable to outdo their last greatest achievement. That fear either slides into depression or a burning fire to prove themselves wrong. That fire continues to keep them on their feet, anxious of the day they disappoint others, but most of all, themselves.
They have friends and family they deeply trust. They value the opinion of their confidants to keep them grounded. Confidants who prevent the hype get to the individual’s head, without discounting his/her achievement.
They themselves meet with exceptional people who show them the world is bigger than their pond. Exceptional people who challenge what they themselves know and what they think they know, helping them realize the limitations of their own world.
Regardless of what stage of life we are at, I believe there are life lessons here for everyone else as well.
Your greatest achievement is ahead of you. Don’t spend too much time on the past, even if you are proud of it.
Find a support group who’ll be with you even when times are tough — when your faith in yourself falters.
And, hopefully that same support group of friends and family will keep you grounded, even when the world tells you, you are a god.
Meet with people who challenge you, who inspire you, and who motivate you to act.
Of all the above, I’d love to double-click that last lesson in particular. There are two kinds of lives that great people live:
A life to envy
Or a life to respect
A life to envy is a life you would love to live instead of your own. It is often easier and more privileged than your own. A life born with a silver spoon in their mouths already. And if not that, a life of fairly few struggles or of extreme luck uncorrelated with their ability to hustle. These individuals often live only briefly in the limelight and find it difficult to repeat the “success” they’ve had. For instance, winning the lottery or being born into a well-off family.
A life to respect is a life where the individual overcomes seemingly impossible odds. One built with sacrifice — blood, sweat, and tears. It wasn’t an easy one. But where they are today is a testament to the scar tissue they’ve built over the course of their life. There are chapters in these lives that could and would rip apart the average person. This life is a life best viewed in a cinematic theater, but not one most people would want to live themselves, even though the status quo may be something they desire for themselves. I often find the world’s best founders in this category. And these lives often stand the test of time.
Most of these people won’t forget the past they came from. They continue to have insatiable curiosity and a bias to action. As such, they continue to learn at an astonishing pace. They continue to inspire us and motivate us to be better. And even before they succeed, many of their peers who don’t join them for the perilous journey merely comment on how they’re “built different.”
These are the same people I love spending time with. And hoping that when I do “make” it, I won’t forget their wisdom.
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
A founder looking to write more long-form recently asked me, “What does your writing process look like?” As I was sharing my long answer to her short question, I realized, “Holy f**k, my writing process sure has evolved over thepast few years.” In an effort to encase my current thoughts in amber, I find myself transcribing thoughts from gray matter to illegible scribblings. And from a 180-grams-per-meter-squared canvas to a two-dimensional electronic screen once again.
A trip down memory lane
I remember when my friend first asked me, “How are you able to commit to a weekly writing schedule? Aren’t you busy enough?” And I shared a secret with him. Something that one of my mentors shared with me.
Before officially starting my blog, I wrote 10 essays – a Plan B in case I ever went through a dry spell. Knowing I had the comfort of a cheat week and still having content to put out gave me the courage to continue writing every week. Almost three years later, of those 10 initial pieces, I’ve only two of the afore-mentioned. In the world of content creation, there’s a massive graveyard of creators who never make it past 10 pieces of content – be it blogposts, podcast episodes, YouTube videos, and so on. I would know. I started 3 blogs before this one. For each of the three prior to this one, I have an epitaph that made it to five or less posts.
The evolution of process
In my first year, I usually spent time conceiving a blogpost at night when I found myself to be the most creative, and editing the same one in the morning before the rooster cried to the awakening sun, when I found myself free of distraction and in peak efficiency. Yet despite a greatly industrialized process, one consistent theme throughout 2019 and 2020 was regret from publishing an essay too soon. There were multiple cases where I’d stumble on new, yet relevant information often within hours of publishing. In fact, this gnawing yarn of remorse reached such a level of prowess that I was re-editing blogposts by the paragraph on a monthly basis. Sorry to all of my early subscribers. Good news is you have your very own limited edition copies of David-jumped-the gun-again.
And so I started delaying my publishing schedules – to account for this sense of continual regret. In my current phase, I break down writing into three phases:
Time to create
Time to ruminate
Time to edit
Time to create
One of my friends once told me the secret to creativity is to “give your brain time to be bored.” DJ, one of the most creative people I know, having worked to create some of the most iconic animations we know today during his time at Cartoon Network and Lucasfilm, and now a YouTuber with over half a million subscribed, once shared with me, “Creativity is a residue of time wasted.”
When I asked him to unpack that statement, 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.”
And he’s right. The more time you spend moving or doing, the less bandwidth your brain has to explore new possibilities. The nuance here is not to block some amount of time every day to ideate. In fact, if you’ll allow me to be brutally honest, while it is giving yourself time to be bored, it’s too structured. And by definition, creativity, like DJ mentioned, is unstructured thinking. Subsequently, blocked time often creates unnecessary stress and anxiety to create. Especially when your mind is drawing blanks and you’re on a clock.
Instead, allocate time immediately after your brain has been given 10 or more minutes to be bored. For example, after you take a shower. Or go on a 30-minute run. Or a 20-minute power nap. Simply, even going on a 20+ minute walk helps your brain re-center and refresh. And always, always write down your ideas. No matter how awesome or lame you think it is. The more you practice the art of ideating, the more consistently better your ideas will be. Not saying that I’m the most creative person out there, but I still have “trash” ideas every so often, but at a far less frequency than when I started.
Time to ruminate
If you’ve ever bought a new car – for the sake of this essay, a black Toyota Camry – as soon as you buy it, you start noticing more black Toyota Camry’s on the street. In fact, you’ll start being able to identify the 2022 versions versus the 2021 or the 2016 ones. A combination of recency bias and confirmation bias. The same holds if you go to a new restaurant, you’ll start noticing that it pops up more in conversations with friends or as you’re scrolling through Instagram.
On the same side of the token, once you seed an idea in your brain (or better, on paper), you start realizing, there is more content and discourse in the world about said idea than you once thought. In the time I spend between creating and editing, I stumble upon or (re)discover articles, podcasts, conversations, experts in my network, just to name a few, when I give my brain time to ruminate.
I like to visualize the scene from Ratatouille when Remy is savoring the individual and collective flavors of the strawberry and cheese, unlike his brother Emile who gorges food down without a second thought. Whereas Emile loses the magic of culinary world, Remy sees what no rat has been able to enjoy prior. Simply put, be Remy! Savor your thoughts.
Time to edit
For me, editing has become the easiest, yet hardest part of writing. All I have to do is string together words and thoughts. I have all the biggest pieces on paper already, but formatting, grammar, punctuation, you name it, feels just like busy work, especially where there are so many more productive things I could be doing.
So, time to edit is akin to time to be inspired. As such, there are two takeaways I’ve learned about myself over the past three years:
I edit in the early morning or late at night. No one will ping me (usually). There is no urgency to respond. Simply, no distractions.
I have a Google doc (which I might share one day, but as of now, it’s a hot mess) that includes all the pieces of content that has, in the past, inspired me to feel a distinct emotion. I use this library of emotions when the content I am creating (blogpost, email, pitch deck feedback, replying to a friend who’s in a rut) requires empathy. For example…
If I want to feel sad, Thai life insurance commercials are my go-to 5-minute sadness augmenters. Here’s one of my favorites.
For pure inspiration and drive, Remember the Name or any of Eminem’s songs.
In closing
While I don’t timebox myself in this 3-step process, on average, writing a blogpost takes me about two to three weeks. In case your curious, any blogpost where I lead with a sentence that includes “recently” instead of a set time probably took a few weeks to come to fruition.
In effect, writing never feels like a chore. Rather, it’s inspired. Inspiring. Uplifting. And de-stressing.
#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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
