I gotta say I love it! Memes. GIFS. YouTube vids. TikTok clips. The whole nine yards.
As a testament to how much I love satirical memes and GIFs, six years ago, when I was testing out “best” cold email methods, as a semi-random A/B test, I emailed half of the folks I reached out to, leading or ending with either a meme or GIF. The list ranged from authors to musicians to researchers to Fortune 500 executives to founders to professional stone skippers. And the results weren’t half bad. Out of 150 odd emails, about a 70% response rate. Half of which resulted in a follow-up exchange by email, call, or in-person. The other half were gracious enough to say time was not on their side.
I just finished episode 5, where they share a snapshot of comedic ideas and pitches – from lipid fuel technology to an Airbnb marketplace for prisoners. And not gonna lie, I had a good chuckle. But when the episode wrapped up and I finally had a chance to think in retrospect, those ideas could have been real pitches in some world out there. When I first started in venture, I met with my share of cancer cures predicated off of a happiness matrix and feces fuel and African gold brokers. In case you’re wondering, yes, I did get pitched those. The last one admittedly should have come through my spam folder.
In these next few weeks, while you’re WFH (work from home), if you’re curious about tech from the ironic perspective of those who live and breathe it every day, check the series out. Only 10 episodes. 7-15 minutes per. (And while you do that, maybe I’ll finally get around to watching Silicon Valley. But no promises.)
As a footnote, Bessemer also has a track record for being forthcoming and intellectually honest. I would highly recommend checking out their anti portfolio, that lists and explains not their biggest wins or losses, but their biggest ‘shoulda-coulda-woulda’s’.
#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!
One of my buds asked me over the weekend why I often don’t namedrop, mostly in respect to this blog. Well, other than the quotes I use that already exist somewhere on the Interweb. It’s not the first time I’ve been asked about namedropping. And I usually my TL;DR response is that I want to respect their privacy and time.
My longer answer is a bit more nuanced. Here are my reasons to why:
If I’m true to my emotions, I would love to namedrop at every opportunity I get. Given that some of the folks that inspire me to write specific pieces are echelons above me, it would help me get exponentially more traffic. And for a minute, I can convince myself that people come to my site for the content. Yet, in reality, there are confounding variables, part of which is whom I’m rubbing my shoulders with.
Although I tell them during our conversation, I send my pieces to the people who inspire me retroactively. In receiving feedback, if existent, after I publish my thoughts, I can truly give a play-by-play cross section of my thoughts at any given time. If I believe the feedback/advice is pertinent, I will compound upon the advice in a future post. After I publish the pieces, if they want to be associated with it, they can, which leads to my third point.
Fame is a fickle thing – a double-edged sword. I’m not saying my blog currently has millions of views every month, nor am I projecting that it’ll ever. Would be nice, but not a priority. But since I do write on a public blog which can be found via various search engines and browsers out there, I am cautious and respectful of people’s comfort levels in the face of the public eye. So, before they decide to have their names on my blog, I send them this incredibly intricate piece Tim Ferriss wrote about fame. On the bright side, social recognition, the opportunity to take on bigger projects, the ability to mingle with people of a similar or greater popularity, and more. On the flip side, stalkers, harassment, extortion, death threats and so on. In understanding the “disclaimers”, then I retroactively put their name up.
Because of these reasons, I’m also, to my friend’s credit, testing the question: Are these people real? The supposed elephant in the room. No matter how much I plead my case, there’s little I can do to convince you these individuals are real. I don’t host a podcast (although I may in the future), nor do I ask them to post on their social media about my content. If you don’t believe they are, they aren’t. If you do, I thank you for your confidence in me. And that’s all I can really say to that question.
Outside of the blog, I try not to namedrop, unless it becomes impossible to explain a conversation topic without using their name. I’ve had such cases before that upon using X person’s name, friends, family, coworkers, and/or acquaintances implore an introduction. After all, as my job entails, I live off of introductions. I live and breathe in a relationship-based industry. And because I do, I’d like to say I have a deep understanding with the value, as well as the risks, a person needs to take:
to make an introduction (which I brief in this piece),
but also, to receive an introduction.
The person making it is risking social capital, or in other words, their reputation. The person receiving it is risking time (and effort) allocation. And when you’re punching above your weight class, the person receiving it has to weigh the opportunity cost of taking an intro versus the projects they’re currently undertaking, as well as prioritizing a new contact over their existing network. If I do make an intro, I always shoot for a double opt-in, where both sides agree to it.
Early last year, I heard something I don’t know why it didn’t click sooner. As part of the Crazy Gremlin (CG) (long-story short, we couldn’t think of a better name) event series which I help co-host, we get in-person feedback with each and every attendee. Why? We can dig deeper than we can with survey forms, like:
Understand the deeper emotional spectrum,
Ask pertinent follow-up questions,
And, notice macro- and micro-gestures that’ll supplement how forthcoming their answers are (i.e. Does a “9” on the NPS question really mean a “9”?).
For context, the thesis behind CG events is helping strangers become life-long friends overnight.
In that feedback process, one of our attendees told me: “I’m never going to come to your events again.”
I asked, “Why do you say that?”, assuming that we did something terribly wrong.
“You guys didn’t do anything wrong. In fact, you held a better event than I imagined. But in coming to the last event, I realized I would rather prioritize my current close friends than spend time meeting new people, whom I don’t know if I’ll catch up with later.”
He made me realize that:
We failed at bringing people closer together, fundamentally being comfortable with being vulnerable, at that event.
There’s a giant population of folks out there who say they want a social life and to meet new people. But what they really mean is that they’re still looking for that friend or group of friends with whom they can really truly be themselves with.
To this day, I don’t think namedropping or making intros when only one party could benefit is conducive to lasting friendships. So, although it makes me giddy, and you can argue, in a myopically-beneficial sense, I proceed cautiously.
#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!
I woke up today with a thought that’s been gnawing at me for years now. Why do we have backup plans – Plan Bs, Plan Cs, etc? Does it inhibit our drive? Or readily prepare us for the worst? At what point are we sacrificing our commitment for safety?
When I started this blog, my writing mentor recommended that I have 10 pieces written and ready before I launch my blog. And I did exactly that. All cards out, I still have 8 of my pieces saved in my backlogs, which as you have already deducted, I’ve used 2 of my pieces already. Why? My mentor told me that, in my commitment to publish content weekly, I will indubitably have dry spells – dry weeks. And I did… twice. So, I regressed to my lowest common denominator and pulled something out of my archives. But during those two weeks, it helped me stay in my comfort zone. That instead of fighting writer’s block (if such a thing exists), I chose to run from it.
Part of the reason I started this #unfiltered series is to help me be content with content. I am guilty of 8/10 times second-guessing my way out of doing something. If I contemplate over something long enough, I’ll realize fears that I never thought possible, and opt for the safer option – not doing it at all.
From when we were young, we’re taught to always prepare backup options. When applying to colleges, we’re told to apply to our 2-3 reach schools, and 10-15 other schools we’re confident about getting into. When applying to jobs, one of my hometown neighbors, 2 years my senior, advised me to apply to 200 jobs, expect 10-20 interviews, another 3-5 for final rounds, and 1-2 offers to choose from. Effectively, asking me to apply to 198 backup alternatives.
I get it. As the saying goes, beggars can’t be choosers. Both high school and my early years of college have drilled that saying into me – by my peers and by my teachers.
A part of me hates it, but a part of me realizes the truth in there. I saw that circumstances played an even larger role for my friends and peers who:
are going through tough times in this pandemic and economic downturn,
(whose) parents came from a lower income bracket,
are POC (people of color),
are female,
are/were open about their different sexual orientations,
didn’t graduate from a 4-year college,
lost limbs or appendages due to accidents or conflict,
are/were in debt,
and much more.
Half a decade back when I set out to meet one new person that drew my insatiable curiosity a week, I realized I’m a goddamn privileged person living in the 21st century. I’m a perfectly healthy, heterosexual Asian male who graduated from a 4-year university. If all hell breaks loose and my net worth goes to absolute zero, I have my parents’ home to go back to and a room and bed to call my own. And as a full disclaimer, the fact I’m contemplating this question in the first place means I’m privileged enough to do so.
And because I’ve had the liberty to do so, I realized that my greatest personal achievements came from when I didn’t give myself the option of a Plan B. For the people I reached out to and am in touch with above my weight class, I either have given it my all or was prepared to do so. For swimming, I treated each competition as my last, meaning I either gave it my all or nothing. And during more nights than I can count, I beat myself up over my inability to reach a milestone.
Yet, now in the land of venture, we learn to hedge our bets and come up with contingency plans. We learn once again to diversify our portfolio, and not put all eggs in one basket. Does that lead to why many investors fundamentally don’t have the conviction to lead deals?
On the founding side, you have it almost flipped. When you are trying to make ends meet, there will be times you have to take that one option and go all in. And you can’t let go until you do everything you can to make it a reality. When you sit in a position of privilege, you can have several contingency plans to hedge your bets. Ben Horowitz, author, founder, and investor, illustrated the dichotomy in his piece (and one of my favorites) about peacetime and wartime CEOs. There’s a part of me that strives to find that sense of urgency, like a wartime CEO. And go all in. Maybe this pandemic is the test where I can find where my values really lie.
To be frank, I haven’t come up with a conclusion to the dilemma. For now, I can only hypothesis-test and keep good track of the data that comes my way. But, so far, I can say that one’s tolerance for risk is positively correlated with one’s free cash flow.
#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 a result of my love for food, and eating out, honestly, a bit too much, what started as engaging conversations with chefs at some of my restaurants, and eventually chefs from across the country turned into a passion for cooking. Uhh, well, although I can’t call myself a cook or chef, I have categorized myself as a flavor mad scientist.
Cook– someone who can prepare food
Chef– someone who can create recipes appreciated by a wider audience (personally, don’t care if they’re a professional or not)
Flavor mad scientist – someone who attempts to be innovative and likes experimenting with permutations of flavors and textures (80-90% ‘failure’ rate), aka me
So, I chatted/learned from chefs/cooks, ranging from some of the most prestigious kitchens to my favorite home kitchens. Here are some tips and hacks I got from some of the best:
For the carbs:
You can tell if a risotto (or rice in general) is cooked by smearing a rice grain on a flat surface. If it smears without noticeable lumps, you’re good.
Add a teaspoon of olive oil in the pasta dough to give it a bit of shine.
Flour matters. Don’t just use all-purpose. 00 (double zero) for silkier flour and pasta chewiness. Durum for coarser grinds, longer cook times, and for making flatbreads; some use it for pasta too, depending on the chef. And so on.
For the proteins:
Score the fat of a (ribeye) steak before searing, so it’s easier to render the fat. Score is a cross-hatch pattern. More surface area to render.
Use tongs to cook steak and a spoon to butter-baste (I swear I used to think it was spelled “butter-basing”)
Don’t cook cold proteins (meats/seafood). Let it rest till room temperature before cooking.
Allow for meats to rest for as long as you’ve had it in the pan to better absorb the flavors.
Before searing proteins, dry with a paper towel or season generously with salt to reduce moisture and splatter once you put it into the pan.
Hot pan/hot oil, quick sear and won’t stick to the pan.
Brush fish with mayonnaise to prevent them from sticking to the grill. And a great browning too.
Use cuts of meat that are rich in marrow and collagen (cartilage) to make stock, like wings, chicken feet, chicken carcass, pork knuckle, etc.
If you don’t have a meat thermometer, stick a metal rod (or a cake tester) into the center of the meat. Then place the rod on your lower lip. If it’s cold, more time. Hot, it’s done. If you’ve burnt your lips, well… in gamer terms, GG.
For everything else:
If your meats or onions ain’t sizzling in the oil, the oil in your pan isn’t hot enough.
To not bruise your herbs when chopping (or chiffonading if you want to be fancy), you need a sharp knife and cut once per cross-section. You can tell if you bruised your herbs by the residue they leave on the chopping block.
Lemon juice, ideally fresh, helps fruits from oxidizing (after being cut), so it retains its fresh color.
Flavor extra virgin olive oil (EVOO) with herbs (i.e. bay leaves, basil, rosemary, thyme, oregano, etc.) for the “secret” zing to your recipes. You can do the same with white wine that’s used for deglazing the pot/pan.
Zest citrus in once in one fluid motion with a zester to prevent mixing in the bitter rind.
Use fine grinds for salt and pepper to season pre-cook, and coarse grinds for post-cook/presentation.
Buy whole spices and a spice grinder (or pestle and mortar), instead of ground spices. You’ll get fresher and richer flavor that way.
Toast spices for more flavor.
Under-seasoning is a rookie mistake. (Admittedly, after this tip, I fell under the category of over-seasoning.)
Keep your work station clean. Mise en place.
Wear short sleeves while cooking, or roll up your sleeves.
If you’re a 4-eyes, like me, invest in contacts. Glasses can fog up from the steam, and possibly blur your vision in critical moments.
Don’t skimp on costs. Quality cookware and ingredients lead to quality food. (Not saying you can’t otherwise get a good meal, but you’ll notice the difference.)
You may notice that I just transcribed what I wrote on paper to this blog, with some extra sprinkles on top.
#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.
Yesterday, I grabbed a coffee with a friend – now a newly-minted manager. Between congratulations and hearing what she’s been up to, we dove into a rabbit hole about performance reviews. And out of everything she shared, there was one question that caught my attention:
What do you say “No” to now that you didn’t say “No” to when you started?
People are inherently loss-averse. We react stronger to losses than gains. Economic prospect theory has taught us that much. Essentialism, probably best popularized by author Greg McKeown, or a methodology that helps us differentiate between external noise and our internal signal, takes it a step further. For example, the questions:
How much do you value an opportunity?
And, How much would you sacrifice to obtain an opportunity?
… carry two different emotions. We take many aspects of our lives for granted. But when we lose any aspect of it – be it a body part, a friend or family member, or a habit – where we once lacked appreciation, we now find true value.
What we say “No” to carries layers of scar tissue – of our past we don’t want to relive. The French language has an incredibly apt way of describing knowledge. Savoir denotes simple knowledge acquisition. Connaître implies a familiarity with knowledge that is deeper and carved into one’s heart. When my friend decided to ask that question, she is looking for what her team members connaissent.
I love it! And I’m gonna steal it (well, with her permission)! For each time frame, we have a new set challenges to ‘pattern-recognize’. Founders have it cut out for them. And just by the nature of their work, they need to learn – fast.
“When I studied Tai Chi for a year, I thought I knew what I was doing. And I thought I was really started to understand it. But after 2 years, I realized everything I thought after a year was wrong. It was just wrong. But now I understood.
And then after 4 years, I realized everything I thought after 2 years was wrong. And he went on with this story and this pattern, but now I understood. And after 8 years, everything I thought after 4 years was wrong. And now I’ve been training for 16 years; everything I thought after 8 years was wrong. And now, I finally understand…
It’s easy to think we’re in the dark yesterday, but in the light today. But we’re in the dark today too.”
So, in foresight and honest vulnerability, I will take my friend’s question a step further:
What will you say “No” to tomorrow that you aren’t saying “No” to today?
Coronavirus. Candidate primaries. Market crashes. And what motivates us to get shit done. During a bite with one of my buddies from college, we ended up chatting about a myriad of topics. From crying when we scared as a baby to eating when we’re hungry, humans inherently act reactively than proactively.
Let’s put it into perspective:
Wildfires in Australia and previously in California brought nature preservation front and center.
Because of the coronavirus, China set up a hospital in 10 days. Whereas in SF, it takes years to extend our public metro, BART, to just one more station.
In startup land, look how much innovation is being done on the SaaS front. Competition drives progress. A need to be better than your competitors, or perish. On the flip side, innovation at the frontiers of technology are happening at a much slower pace. You’re right in thinking part of it is due to an element of technological risk and mystery. But a large part is also due to funding, awareness, and urgency. I was catching up with another friend, not too long ago, who’s working on the frontiers of AI research. He told me that he’s just not motivated to meet any deadlines. If he misses it, “Oh well.” And if he does reach any milestone, there’s barely a pat on the back.
Neil deGrasse Tyson, and I’m paraphrasing here, once said (in one of his StarTalk Radio episodes): we think if we reach commercial viability of space travel or tourism in 50 years, that it’ll be really impressive. But it’s really not. Why? If, hypothetically, aliens from another galaxy contacted us today and said, “We’re going to invade your planet in 50 years”, we will have a different sense of progress. And if in 50 years, we can only just start to commercialize space travel, we’d be sitting ducks.
If you have a final in the morning tomorrow and you happen to be a procrastinator (or not), you’re going to be burning the midnight oil. Otherwise, realistically, would you be studying day and night every day?
Tim Ferriss asks himself this one question: If in 2 years, you’re set to die. In perfect health, and a perfectly natural death. What do you have to do before you die? What will you regret no having done? So, what really matters? (I lied; it’s not really one question.)
So, how do I induce a sense of urgency? How do I motivate myselfwhen I don’t have any impending time horizons?
One, accountability partners. Friends who keep me (and me them) accountable to my goals, like my birthday resolution. Where in 6 months, upon failure, I lose $100. Or upon success, I get treated to a really nice meal.
Two, something I took from my good friend. I once asked him about how he continues to push himself towards new experiences every month. After all, he’s the kind of person who lives a life that makes me feel as if I’ve done nothing. In response, he said:
“Fall in love.”
“I don’t get it,” I replied perplexed.
“Because it’ll make you want to impress your crush. And when you go on that date every week or every two weeks, you’ll want to show off. And the only way you can show off is if you have something to show off. So, I don’t let my dreams sit. I get shit done.”
#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.
Today, I read a 2017 piece on Nylon about advice from black writers to black writers. And there was one particular quote that caught my eye.
“Don’t edit while writing a draft or else you never finish.” – Terry McMillan
I can’t speak for the writing industry as a whole; I can’t even speak for my friends who are writers. Didn’t ask. But I can speak for myself. For this blog. Admittedly, 70% of all pieces I start writing, I don’t finish. And quite honestly, I almost hate that about myself. Writing for eyes that are more than my own has turned me into a perfectionist. The very thing I once swore to not become.
So, I’m going to try an experiment. More so for myself, in hopes of reducing the friction for me to write more. Every so often, I will post something I will title as “#unfiltered”. It’ll be less of a well-constructed thesis or methodical breakdown, but more of a writing to help me think. In sum, it’ll be a brain barf. 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. Don’t feel obligated to read it. In fact, if you don’t like brain barfs, don’t click on any of them, prefaced by its own #spoileralert. But if you do like unfiltered commentary and my rough thoughts, stay tuned. 😀
In the past two weeks, through conversations on my birthday resolution and what my success metrics are, my friends inspired me to write this post . That’s when you know I’m in Silicon Valley! Or startup Disneyland.
So, how do I measure my progress? This is by no means proprietary or original. In an annual email exchange, my mentor had me ask myself one question:
How ashamed do I feel about myself one year prior?
Although not comprehensive, I find it to be a great litmus test for evaluating personal development. If I don’t scoff at my former self for being dumb, I’ll know I haven’t progressed. At the same time, I put myself in the shoes of my future self, abstracting myself from my status quo, and ask two questions:
What aspects of my past self am I embarrassed to see?
What strengths of my past self would I find extremely unimpressive to show off?
This acts as an ego check and helps me look at myself more objectively.
I started this practice two years ago where I keep a checklist (on Google Keep) of wins I keep track of throughout the year. It included any magnitude of achievement, like:
A successful deal close;
Joining as a guest on a podcast;
An art piece I’m proud of drawing;
Cooking a meal that pleased my parents;
And, sleeping 8 hours a night.
Then one week prior to my birthday, Google Calendar reminds me to go through that checklist and review what I still feel proud of and what I find to be ‘normal’. I check all the ones I no longer gain contentment from. All that’s left are “My Proudest Moments at Age XX”. Then my goal for the following year is to make those moments feel ‘normal’. I’ll get to this step eventually. But I plan to review the annual lists every 5 years to see if I still feel the same.
In a way, this blog is also designed for me to reflect on earlier iterations of myself through my writing. As much as this one question has enlightened me, I hope it may act as your heuristic for your growth.
My parents have always conditioned me to plan each of my ages out. When I was younger, every year I ranked up they would ask me what I want to get done. At the same time, I never felt a strong commitment to New Year’s resolutions. Maybe it was ’cause of the gingerbread cookies. Or the Christmas presents. Or the fireworks and the ball drop. But that lull between the holidays wasn’t conducive to me setting meaningful goals. The “promises” I made carried no weight behind them.
Three years back, after reading Brad Feld’s birthday resolution, I decided to start setting my own birthday resolutions. Outside of a mere date shift, there were 3 reasons I chose to do so:
I had time to recover from the holidays – to get my head straight.
I was motivated watching my friends, family, and coworkers tackle their New Year’s resolutions in the month prior. (Admittedly, more often than not, they lose their initial trajectory, but I only saw the beginning of many of their inverse parabolas.) Motivation is one side of the coin; FOMO is another.
In that motivating January, assuming I haven’t yet completed my previous year’s resolution(s), it motivates me to finish strong – the “last mile” sprint.
That said, this is my first year posting my resolutions publicly. Why? One, it’s to keep me accountable. Two, as Jeff Wald once said, “practice true vulnerability by opening up about the potholes ahead, not just the ones in the rearview mirror.” And one of my resolutions from v23.0 was to become more comfortable being vulnerable. So, what will the new update look like?
Here are the patch notes:
Build ideas from 0 to 1.
This year, I plan to actively help 2 startups go from idea to product-market fit. After 3 years on the venture side of the cap table, the one thing I’ve noticed more and more is that I miss getting my hands dirty, especially in the early stages. I miss the ups and downs. I miss the freaky moments (and the big wins). It may sound a bit weird. But I may have emotionally removed myself from being entrepreneurial and trapped myself in a bird’s-eye perspective only. And I hate it.
More artistically creative outputs.
Two years ago, I started idea-journaling by inspiration from my former college professor. After going through 9.5 idea journals, I realized I’ve spent less than 10% of my ideation space on artistic pursuits. 40% on VC and startups. 40% on personal projects and experiments. 10% everything else. There’s clearly a lack of diversity in my creative space. So, this year, I’m committing to producing one new art piece every week – be it a new drawing, music composition, culinary permutation, or something that’ll surprise myself. My deepest gratitude to my friends who gave me new canvases to explore my creative white space. You can track my progress on my Instagram.
Balancing Social Media.
In the year when many of my peers are unplugging, I’m going to be more active on social media, fine print included. I’m going to explore more by contributing content on this blog, my Instagram (for artistic pursuits), LinkedIn, Medium, Quora, Reddit, and Discord.
I’ve always shied away from social media – not because of some grandiose sense of self-discipline, but rather since I’ve never been able to fully conquer my shell of introversion. After all, my Facebook profile picture and lack of presence is my form of psychological armor.
That said, I still won’t be scrolling through my news feed on social media. But I will aim to respond to every comment and DM that comes my way. I’m a firm believer in responding to the commitment and time people take to write a thoughtful message. Luckily, I’m also at a stage in my life and career when I don’t have more messages/emails than I can manage.
Reconnecting.
Over the past half decade, I’ve grown a lot from reaching out to, learning from, and helping new folks in my network. And, I’m grateful for each and every experience. I wouldn’t be here today if it weren’t for them. But as a result of constant pursuits of new experiences and expanding my network, I haven’t been able to reconnect with friends, mentors, teachers, and acquaintances I’ve had in the past, outside of my annual holiday greetings and thanks. In this new update, I’m committing 10 minutes every day to meaningfully rekindle old flames that I haven’t caught up with in the past 6 months.
Read more.
By virtue of reconnecting with friends from my past, it’s useful to have content and inspiration when reconnecting, but also as a means to widen my own knowledge horizon. Outside of work and my one-book-a-month of reading, I’ll be indulging in a minimum of an hour of diverse reading every day via the ‘Discover’ tab on Pocket.
Sleep and wake earlier.
Ever since college, I’ve been a night owl. It’s weird ’cause in college, students apparently have this ego contest of how many ‘all-nighters’ one can pull and still be ‘alive’. Being young and naive, I joined in the chorus, but I never won. In fact, in my entire college career, I pulled only 2 all-nighters, not even back-to-back, and I was already dead. But it ended up ruining my sleep schedule. I would go to sleep between 12 and 3AM. Sometimes for no reason at all.
After I came back from my holiday Europe trip, mostly due to jet lag, I started sleeping at 9PM every night for the first week. I felt so much more refreshed in the morning and through most of the day than when I didn’t. But also, there’s so much less noise in the morning between 4:30 and 6:30AM – both on social media and in the neighborhood. And I could much of my creative work done. This year, I’m going to sleep at 10PM latest and wake at 4:30AM.
Goal-oriented exercise.
I haven’t necessarily been unfit, but my daily routines seem to drone by without any personal achievement or goal in mind. I have no plans to reach my past physical prowess where I spent 30-40 hours a week spent on exercise. But this year, I’ll stick to 2 goals for health and exercise: sub-5:30 mile and 20 pull-ups. (I’m at a 7:15 and 7 pull-ups at the time of writing this post.)
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It’s going to be an exciting year, and I plan to have plenty of hotfixes before I reach v25.0, hopefully daily. Thank you to my friends for all the birthday wishes, support, and feedback.
I have a love-hate relationship with that word. On one hand, I love and seek to learn from creative souls. It’s a trait that I seriously respect in individuals, regardless of industry, profession, or background. On the other hand, it’s rather amorphous. What’s creative to me may not be creative to you. We are bounded by the parameters of our experiences and what we, as individuals, are exposed to.
So, where do innovators draw inspiration?
Over the years, I’ve seen inspiration stem from three main frameworks:
The flow from art;
Margins;
And, what people dislike.
The Flow from Art
I seem to find that the data largely (with a few outliers) points towards the following:
Art precedes science. Science precedes tech. Tech precedes business. Business precedes law.
Art is bounded only by one’s imagination. Science, which draws inspiration from art, is limited by our physical universe and the fundamental laws. And, tech rides on the coattails of science, restricted by the patterns recognized in our universe by scientists before them. Similarly, business can only optimize existing technology. Following suit, regulations and legal practice can only debate and prevent ramifications that have turned from hypothesis to reality.
On one end of the spectrum, fiction has driven innovation on the fundamental, scientific front. Scientists have tried to make the impossible – fiction, superstition, assumptions, and imagination – possible. On the other end, the legal and regulatory space has empirically lagged behind business innovation. From autonomous driving to the shared economy to video games, a regulatory emphasis came only after incidents occurred. I’m a huge proponent of founders becoming self-regulatory. But that is a discussion for another day.
Margins
As Jeff Bezos famously said:
“Your margin is my opportunity.”
In the lens of a businessperson, profits exist on the margins. In a fully saturated market, as we learned in economics class, perfect competition will squeeze out profits. That margin can be delta between human perfection and imperfection. It can be the difference between a naive and sophisticated individual. It can also be the blind spots between a self-awareness and ignorance.
The good news (and bad news?) is that humans aren’t rational. As much as we try to be, we’re not. We repeat the same mistakes. After all, that’s where our favorite stories come from – the fact that we’re imperfect. If we were rational, our friendly neighborhood kid from Queens wouldn’t have to struggle with identity. Or, Skinner, the head chef at Auguste Gusteau’s restaurant, wouldn’t be out to exterminate my favorite rat chef.
From a nonfictional front, if we were rational, gambling, the lottery, therapy, and more wouldn’t exist. In fact, there’s a whole industry that capitalizes on human imperfection – insurance. We choose to reach for that last cookie when we know a healthier diet with less sugar is better for us (I’m guilty as well). We set New Year’s resolutions to work out more, but regress to our couch norm after the first month. Walter Mischel famously conducted The Marshmallow Experiment. When given the option to wait 15 minutes to double their treats, many children opted for immediate gratification.
There would be way fewer founders if they were rational. I mean, come on, the numbers work against them. 90% of startups fail. So, from a VC’s perspective, we have to ask ourselves:
What’s is the underlying notion that makes this product work?
What is that innate theme in human or societal development that won’t disappear anytime soon? What factors produce such a trend? And what margin is it taking advantage of? Uber was made possible with the evolution of smartphone and faster data. As more data were archived online, Google became a reality because of the internet and browser. Two current examples of underlying notions include:
Audio, including, but not limited to, podcasts and audiobooks, is the new form of content consumption. Not only does it free up consumers’ hands and eyes up, audio content is often easier to digest. The spoken word has been around millennia, whereas print is fairly new invention. Emotions and sarcasm is often easier to relay via audio than via print. So, what else is possible?
With growing consumer sentiment against traditional social media, like Facebook, Twitter, and Instagram, there is a shift to social experiences surrounding active participation. Sarah Tavel writes a great piece on this. Examples include Discord, Medium, TikTok, and user-generated content (UGC) in video games, like mods and in-game skins. Many of the traditional social media platforms leave users with a more negative passive experience, where they feel a sense of FOMO (fear of missing out). Through active participation, users can be a part of the conversation, rather than watch from the sidelines.
What do you dislike?
Speaking of negative experiences, aversion is a strong motivating emotion humans have. Like prospect theory illustrates, loss invokes a stronger response than gains. It also happens to be one of the reasons why I probe how obsessed a founder is about a certain problem.
In a recent interview with Andrew “Kappy” Kaplan, host of the podcast, Beyond the Plate, Grant Achatz, legendary chef, talks briefly about how he drew inspiration from his daughter’s dislike of cheese, yet she still ate pizza and grilled cheese sandwiches. Similarly, when his guests at Alinea didn’t like sea urchin, he thought about the ‘why’ and if he could circumvent their aversion by playing with various variables, including iodine concentration.
So, what do you dislike (with a passion)? What about the people around you? And can you figure out a way to change or eliminate that frustration? Take some time through the idea maze.
In closing
Ideas come in all shapes and sizes. Some may be more obvious than others. Some may snowball into a best-selling one. Although I’ve shared the three most common frameworks that I’ve personally generated and seen others find inspiration, it is, of course, not the only ways to exercise your creative muscle. In fact, the first step into being more “creative” is being cognizant about everything around you.
Two years ago, one of my former professors recommended I start ‘idea-journaling’ every day. Since I’ve started, I began noticing more and more stimuli from my surroundings, conversations and frustrations.
It may be a start, but it’s by no means an end. Stay curious.
