Tag: unfiltered

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#unfiltered #12 Spilling the Beans – Sharing Insights

idea maze, spilling the beans, sharing secrets

Yesterday, having read my most recent blog post on social experiments, one of my friends asked me why I decided to finally start the blog. My simple answer was “to make myself obsolete”. The question that inevitably followed was:

“Why?”

Although not incredibly common, I’ve had a very small handful of friends and family ask me similar questions. All of which either directly ask or border “Why share all my secrets?”. Admittedly, all is subjective in this case, as I’m not keen on posting my social security or my social media log-in information on here.

  1. Wouldn’t I be more competitive in this saturated (although I argue otherwise) market if I kept them to myself?
  2. On a startup front, wouldn’t sharing the rationale of others and my own enable founders to “game the system?”

In response to (1), your competitive edge in the 21st century isn’t how many ideas you’ve hoarded, but how many you’ve executed on. And frankly, if we can cooperate to build a better world, why not?

For (2), if founders can “game the system” just by reading my blog, which requires them to have concrete evidence for growth and the questions fellow investors and I pose, well then, it’d be a great example of “faking it till they make it”. My blog merely provides a framework, plus a few stories, to how some of the smartest people around have overcome their obstacles. By the time the system tests them, I hope they’ll conquer the adversity in front of them and have the discipline to push forward.

What’s inside the black box?

I’m extremely happy to share “my” secrets. And I use the term secrets loosely, much like Peter Thiel does in his book Zero to One. In fact, the only reason I have any insight into life is that experienced experts were generous enough to share theirs with me. In other words, none of my insights are truly original. All are borrowed from the best, until I create a version that I resonate with more.

Simply put, if my ‘secrets’ and insights help even just one person out there to live a better life, then I’m a happy camper. My goal is to make the future a better place to live in. Oddly enough, it also happens to be one of the reasons I’m in venture capital. Only by sharing what I believe to be right and morally right am I able to help move the needle, if only by a little bit. As I’ve mentioned before, I’m a huge fan of people going through the idea maze and spending time and effort on insight development. If I can help catalyze those motions in my readers through my blog, then I’ll toast to that.

The Flip Side

However, I should mention there are secrets that I will carry to the grave with me. For instance, outside of the obvious, like SSN and credit card info, ones that…

  • My friends/colleagues tell me in confidence,
  • Cause more harm than good in the world,
  • Cause more harm than good to the people around me,
  • Carry malicious intentions,
  • And/or reveal why I put OJ in my breakfast cereal.

Stay curious!

Photo by Tijana Drndarski on Unsplash

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

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

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Drawing Inspiration

drawing inspiration, ideas, eclipse, writer's block

On Tuesday, I had the great honor to jump on a call with someone who is both a brilliant composer and an acclaimed orchestral conductor. Though he was classically trained, he found fame in the world of video games. And I couldn’t help but ask where he draws his inspiration when composing musicality to pair with various mediums of entertainment, even outside of games. He answered simply:

“Everywhere.”

He followed up that to help him frame his ideas around the subject of his piece: “I watch a little bit, not too much to have the show or game dominate in his mind, but enough to start off.” Just a small spark to start the fire. What he said echoed in mind, reminding me of a conversation I had with another friend – entrepreneur, author, and podcaster – prior to self-quarantining ourselves. He told me: “There’s no such thing as writer’s block. It’s that desire for perfection that holds us back from putting our pen on paper. But once we let go of trying to be perfect, we can find inspiration from everything around us.”

In all honesty, when he first told me this, I thought he was being quite presumptive. Especially it was at a point in time I was struggling to find content to put out weekly. But he was right. And, as you may have guessed, that became the kindling for the #unfiltered series.

Similarly, a few weeks back, a college buddy asked me where I find my inspiration for pieces on this blog. Though I am echelons shy of the musical talent I spoke with two days ago, I offered him the path I took to get me here:

  • Practice ideating daily.
  • Talk to people.
  • Meditate and/or write in a gratitude journal.
  • Write an audience of one.

Practice ideating daily.

My brain, like your brain, is a muscle. The more I practice using it, the better it gets. The same is true for ideas. The more ideas I write, the better I’ll get. It can be one sentence. Or, it can be 5 pages. But make sure to dedicate at least a full page to each day, even if 95% of it may be blank. The point is to deliberately do so every day, with no cheat days. Personally, I spent the first 2 weeks, writing one sentence entries.

So, I invested in an idea journal. In fact, probably my best investment I made in the past 3 years. And, I didn’t bother buying a cheap one. It was a Moleskine art sketchbook. At the time, a $17 purchase plus tax. And for a broke college student, that was a sizable amount – two good meals worth. A good alternative and the one I use now is a Leuchtturm1917 sketchbook. Why? Because it forced me to use it. I realized for me, the better the notebook is, the more I’m inclined to not let it go to waste.

Although I wish this was my original idea, my professor at Cal taught me this simple, but effective strategy.

Talk to people.

When I found myself unable to grasp at any ideas (that I thought were good), I talked to people. The more obsessive they were about their passion, the better. The more (positive and negative) emotion they channel into their work, the more insight they’ll have. And, frankly, excitement is contagious.

Talk to at least one of them from this cohort a week. Take notes, follow up, and ask more questions. The last part usually more independently, depending on their bandwidth.

Meditate and/or write in a gratitude journal.

Be thankful. It’s a useful frame of mind to be in. Positive thinking helps with more expansive creativity. Negative thoughts and stress, depending on its severity, narrows down the scope of your creativity.

Write for an audience of one.

Many professional writers are taught to find a target audience and write for them. Focus on a specific segment, before broadening, if ever. My mentors taught me to take this one step further. Instead one specific segment, just one person. It’s much better to write for 1 person who I know will always love my content than to write for a hypothetical many who may or may not even like it. For me, it’s myself. When I’m writing here, I’m merely a hobbyist. I don’t have any grand goal of reaching one million subscribers (not that I’m opposed to it). I’m just here to immerse myself in the joy of writing. And if I am lucky to have affected someone else’s life in a meaningful way, that’s my cherry on top.

Photo by Jongsun Lee on Unsplash

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#unfiltered #9 Living to Eat – Supporting the Service Industry, Fine Dining Musings, Restaurant Selection Criteria, Tipping, and the Notebook

living to eat, fine dining

I had originally planned to write this post back in February, but when the coronavirus came crashing in 6th gear, I thought it would have been unwise to urge you, friends and family to venture beyond your doorstep. So this post fell into the depths of despair, hoping to find its way to center stage after we were on the road to recovery and when restaurants reopened.

But yesterday, over a Zoom call, in catching up with a fellow foodie and college buddy, he suggested that I still post this. Not to urge people to eat out. But as a voice to support the many struggling restaurants, cafés and bars out there – many of which include our personal favorites. Before I dive into this post, I want to explicitly note 2 disclaimers:

Disclaimer 1: As I mentioned above, this post is not written to incentivize you to go eat out now, but rather just illustrate my musings as someone who loves food. And as many other businesses are feeling the brunt of the impact in the status quo, the culinary industry is no exception. Your favorite restaurant yesterday may not exist tomorrow. And you won’t even be able to experiment with any of the below musings if we don’t put a hand out now and support them when they need us most.

Disclaimer 2: I am neither a professional chef/cook nor is my trade being a food critic. So take what I say with a grain of salt, as with anything I write. Below is merely my observations in one of my most expensive hobbies as a foodie.

Given the extravagant length of this post, here’s a TL;DR:

  • Why I don’t resort to Yelp/Google when picking a new dinner destination
    • And a couple of my favorite restaurants in the Bay Area
  • My calculus for tipping – and why there are times I choose to not tip
  • Why a notebook may be your best friend in your culinary adventures
Continue reading “#unfiltered #9 Living to Eat – Supporting the Service Industry, Fine Dining Musings, Restaurant Selection Criteria, Tipping, and the Notebook”
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#unfiltered #8 The Oasis – Fiction, Books I’ve Recommended/Gifted the Most, How I’ve Kept Myself Busy Outside of Work

book, fiction, reading

Lately, I’ve picked up a few fiction books – 2, to be specific – The Three Body Problem by Liu Cixin and Mistborn: The Final Empire by Brandon Sanderson, by recommendation of a friend and founder, respectively. And damn, they’ve rekindled my love for worldly escapes. Prior to high school, I used to be the biggest fanatic of fiction books. Although proportionally smaller, my fictional “library” at home still includes:

  • every single book in the Magic Tree House series by Mary Pope Osborne
  • the entire Redwall series by Brian Jacques,
  • every single one in the LEGO Bionicle series,
  • the Alex Rider series by Anthony Horowitz,
  • Dune by Frank Herbert,
  • The Steel Wave by Jeff Shaara,
  • and much more.

And to further how much I nerded out over fiction, I knew our local librarians by their first name and memorized by library card number by heart (to this day) – all for the sake of fiction. But as I grew older and entered my teens, I was told that I should have outgrown fiction. That it should stay as a remnant – a fond memory – of my “youth”. So, I slowly acquired the taste for non-fiction, biographies/autobiographies, business books and documentaries.

Yet, in some ways, in this serendipitous situation, when now I have more free time, and by fervent inspiration from the two aforementioned angels, I found sanctuary in other worlds. I saw with my imagination and heard with my eyes. For lack of better words, it was magical.

From non-fiction, I’ve been able to walk alongside the greats who have once or now inhabit the reality on this small blue pearl amidst a sea of unknown. From fiction, I’ve been able to walk alongside the greats who have never lived in this reality, maybe never will, but somewhere out there, they hold the keys to our dreams. Each hold a proud seat in my heart, but the latter has been dormant for over a decade.

Books I’ve Recommended/Gifted the Most

I should preface that I’m not the most voracious reader out there – although that’s been changing over the past 4-5 weeks. But here are my favorites which I’ve recommended/gifted the most:

  • 2018 fav – The Messy Middle by Scott Belsky
    • Short (1-3 pages, on average), but incredibly insightful chapters of product/design/leadership lessons from a founder/investor/product leader, especially during messy times post-honeymoon stage of being an entrepreneur. My favorite pages… 232-234. A set of three questions to create a lovable product.
  • 2019 fav – The Trillion Dollar Coach by Eric Schmidt, Jonathan Rosenberg, and Alan Eagle
    • A dedication to the most well-known least famous person in Silicon Valley. From the book title, you might be able to guess what he did – all of which he took zero compensation for. Having been suggested and subsequently read too many leadership books earlier in my career, when I first suggested this one, I was quite skeptical. I thought it was just another one of those, until I heard the name, Bill Campbell. A name which I’ve heard more than once from various people who attributed their success to him, since 2016. And I’m so glad I didn’t dismiss this one. I only wish I could have gotten to know the amazing person this book is dedicated to.
  • Startup fav – The Hard Thing About Hard Things by Ben Horowitz
    • A book that doesn’t sugarcoat the tough decisions in building a company – a set of decisions illustrating on how he dealt with situations when things just wasn’t going his way. Rather than being prescriptive, it gave me a framework for understanding the various struggles a founder will encounter – most of which I had yet to see when I was recommended to read this book. Quite pertinent in today’s landscape, ironically.
  • Most nostalgic/impactful on personal growth – The Art of War by Sun Tzu
    • I was first given this book when I graduated from elementary school, as the problem child, though not in the traditional sense. I had a knack for blaming others when problems arose, but this book helped me understand people better and where people were coming from. In all honesty, I don’t know why it clicked when I was only 10, but it did. Apart from my childhood bias, though specific to leadership in a military regime, you can draw several parallels between the art of war and business and life.
  • Fiction fav – Salamandastron by Brian Jacques
    • Brian Jacques throughout the entire Redwall series just has such a way to weave suspense and an emotional attachment to the various characters. Admittedly, it was the first fictional book I cried to while reading, so it holds a special place in my heart.

For the sake of not overwhelming you with too much, I’ve only included the ones I’ve statistically recommended/given the most, as well as gotten the most positive reactions from folks I’ve offered these to. If you’re interested in a more exhaustive list, feel free to DM me – either through this blog or social media.

Keeping Body and Mind Busy

For many of my other friends and colleagues, they have found similar solace in books. Many in the kitchen. Some with instruments and a camera. A handful with a mic and Twitch or Anchor.

Because I have saved 2-3 hours of travel time every day now, I’ve been:

  • Doodling at least thrice a week in my Leuchtturm notebook, specifically their medium sketchbook (180g/sqm, so on the thicker end of pages);
  • Jumping on game sessions with friends over the weekends, like on Skribbl.io or recently, Songversations (Discord is definitely my favorite medium of social interaction, especially with all the bots they have. My favorite of which is the Groovy music bot where I can tune into music alongside my friends);
  • Reaching out to 1 new person I’m insanely curious about every week;
  • Idea-journaling every day;
  • Trying new recipes and methods in the kitchen;
  • Trying new home workout routines;
  • Reading fiction and non-fiction;
  • Writing for this blog 😀 ;
  • And, a new social experiment between friends, family, and colleagues, in hopes of making this world feel a little smaller, just a little closer, and a whole lot more interesting.

So, if you have the time and privilege to, explore new/’new’ genres and mediums of storytelling, creativity, and activity. Some may very well surprise you!

Photo by Ksenia Makagonova on Unsplash

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

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups!

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#unfiltered #7 Words are Food – Having Empathy, Job Resources Now, Letting Staff Go, and Perspective Shifts

words are food, empathy

I jumped on a call with my good buddy, incredible founder and one of the most magnanimous people that I know, Mike, not too long ago. And no, he did not pay me to say that. As always, we nerded about everything on the face of this planet, but one thing in particular stood out to me. And inevitably manifested into the foundation of this #unfiltered post. He said, just 3 words:

“Words are food.”

The more we delved into this rabbit hole, the more robust the metaphor began. But for the sake of not running your ear off, I’ll cover just one facet of our parallel.

Compliments are sweets. They’re great in moderation, but too many give you cavities. They wrap up a great meal, but you cannot live your life only indulging in compliments. On the other hand, constructive criticism are your vegetables. They may not taste the best, but they’re healthy for you. And a healthy diet should consist of mostly fruits and veggies. Yes, brussel sprouts and eggplants too. Of course, it’s important to note that blatant criticism, like “You suck” or “You’re dumb” is garbage. They neither taste good nor are they healthy for you. You can smell it from miles away. So just steer clear.

After all, you are what you eat. 😀

Empathy in Words

In the past 4 months, we are all going through a transitory stage in our lives – some more drastic than others. Some of us have experienced the deaths of loved ones. Some, a test of relationship integrity. Others, career shifts and a change in household income. For those of you who have been affected by the job market, my friend passed me this resource which I hope you’ll find use in honing your job search. Anecdotally, it seems pretty accurate.

And almost everyone, a dietary change and restriction, due to the market’s supply and demand. And it’s more important a time than any (not that you shouldn’t when the curve flattens and the markets recover), be empathetic.

Be kind – with your actions and your words. In these times, it’s so easy to be caught up in what’s not going right in your life, but you’re not alone. You never are.

Empathy in Business Now

Although this applies to so many different aspects of our lives, I’ve found its pertinence on the business front recently. When the focus of businesses now is on cash preservation rather than growth, which I’ve alluded to in previous posts (1. cash in private markets, 2. heeding advice , 3. brand as a moat), aggressive decisions can be tough. As the saying goes, measure twice, cut once.

Here are some examples of said (preemptive) decisions I’ve seen from founders so far:

  • Reallocating 30% of the company budget to the core business from expansion and venture bets (70-20-10 rule of thumb to 100-0-0)
  • 50% cut to CEO salary, 10% cut to management, 5% from everyone else, to try to minimize layoffs
  • 100% cut to founder(s)’ salary, 35% cut to management, everyone else keeps theirs the same, while offering healthcare benefits for temporary workers/contractors

The conclusion for some founders may reach the point of laying off people who followed you believing in your dream. You can check out Mark Suster‘s, Managing Partner at Upfront Ventures, rubric for questions you need to consider in empathetic moments of business decisiveness.

Empathy won’t change decisions. The tough, but true remarks are your vegetables. People will still have to eat them, but be understanding of where the people eating the food you cooked up are coming from. Rather than boil your brussel sprouts, offer crispy ones with a soy glaze, a little heat, and a layer of bonito flakes.

Perspectives Forward

Recently, I had the fortune of connecting with a founder whose parents were refugee who found sanctuary in the states. She put things wonderfully into perspective, when comparing the current situation to the one she was familiar with as a child.

“There are 2 camps of refugees: (1) those who want things to go back to the way they were before, and (2) those who move forward knowing that life will never return to the ‘normal’ they once knew.

“And those who progress forward are those who believe in the latter.”

When the dust settles after all of this, life won’t ever be the same as it was 4 months ago. The hospitality, transportation, travel, and service industries, just to name a few, will irrevocably change. You friends and family may have lost dear ones.

Alas, I’m an optimist. And I know that we’re going to come out stronger than we were when we went in. We’re going to have to get used to a new diet. I dare say, even a new vernacular.

#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!

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#unfiltered #6 The Quantum State of Advice – The Marriage of the Schrödinger Equation and Cold Emails

quantum, schrodinger's cat, advice
Photo by Danilo Raphael Reyes on Unsplash

“The rearview mirror is always clearer than the windshield.”

– Warren Buffett

Although Mr. Buffett said that in relation to business, I find it equally true everywhere else. Just like the rearview mirror and the windshield, I want to denote the dichotomy between feedback and advice.

  • Feedback – given post-mortem, after-the-fact, help after peering into the rearview mirror
  • Advice – given “pre-mortem” or in an ad-hoc sense, help offered proactively, looking through the windshield.

As this title suggests, for this post, I’ll just be focusing on advice. And well, that may be as profound as this post will get, the rest is just a trip down my nerdy shower thoughts after watching this video about parallel worlds my equally nerdy friend sent me.

You have been warned…

The world right now

Well, you see, I work in an industry that thrives off of giving advice. Especially in these trying times when businesses are not only trying not to lay off their staff, many are working around how to stay afloat. My friends in culinary projected a 50% decline in occupancy rate, but at this point, have shifted entirely to to-go options and lowered their own salaries anywhere from 35% to 100%. My pals in D2C (direct-to-consumer), transportation, or travel have been punched in the gut. And, my entrepreneurial buddies are doubling down on cash preservation, rather than growth. The rule of thumb we’re telling founders to have at least as much runway to weather the next 18 months. So if that requires pushing up your fundraising schedule, then time to re-prioritize.

The nerd comes out

But after decades worth of receiving advice and years worth of giving advice, I learned something that seems like a no-brainer now. You see, the thing is advice is both right and wrong simultaneously. You can say it’s in a superposition of being right and wrong… at least until that advice is observed by its subsequent application and result.

Let’s take it a step further. Can we predict the probabilistic effect of advice on a given situation? Sure. So, let’s take a look at the Schrödinger equation.

Image result for schrodinger equation

There’s a few elements that stand out. |Ψ(t)> denotes a time-dependent function. And, H(t) denotes the sum of the kinetic and potential energies for all the particles in the system. In relevance with advice, the timeliness ( |Ψ(t)> ) of the advice matters – in relation to both where you are now and where you’re heading. The eigenvector of you. At the same time, it’s important to factor in your velocity now and everyone and everything else’s involved in the situation.

You might be wondering how come I didn’t analogize to the classical mechanics version of this equation: F=ma. Excellent observation! The reason is that the classical mechanics version doesn’t account for wave-like probabilistic outcomes. And advice and its relative observation by application doesn’t have a guaranteed outcome. Rather, it plays a hand in either increasing or decreasing the outcome of an event.

Here’s an example

One of the first lessons I learned, if not the very first piece of advice I got, when learning about ‘Cold Emails 101’ was:

“Limit your email to 3-5 sentences.”

Makes sense. I didn’t want to bombard the person I was reaching out to. I want to make it easy for them to read and reply to. But over the years, I learned that the real answer to email length is ‘It depends’. If you’re reaching out to someone who:

  • already has a lot of clutter in his/her inbox,
  • has expressed disdain or annoyance in reading emails,
  • doesn’t check his/her inbox often,
  • has a succinct personality (person-of-few-words),
  • or anything else that suggests they’re not going to bother with a long email,

… then send the 3-5 sentences. But if that person:

  • wants to see that you’ve spent your time doing your diligence (not a generic spray-and-pray email),
  • has a more extreme sense of self-worth,
  • is curious/open to flushed-out new ideas/perspectives,
  • enjoys a tale,
  • is a comedian,
  • or anything to suggest that a longer email may stand out to them,

… then craft a longer message. I was able to get in touch with some of the people I really admire by crafting lengthier emails. That said, there’s always a bit more nuance in all of this. Here’s a piece I wrote last year that may provide some context. And this is only probabilistically higher, holding all other variables constant.

Even so, there’s always more than two options. DM them on their most active social media platform. Get an intro. Send them meaningful content. Send a hand-written note by messenger hawk. Visit them in person, without unwanted trespassing. Go viral by making a lollipop with their face on it. Buy an extrasolar star and name it after them. The list is endless.

In sum, the advice of limiting the verbage of your emails is right and wrong at the same time. It merely depends on where the person you’re reaching out to is at and where they might be headed, as well as your own goals in life. And of course, as with any advice, limiting your sentences may boost or detract from the likelihood of a reply.

The disclaimer

As is the nature of an analogy, it breaks down when you get more granular. I should mention that I’m no astrophysicist (dealing with the macro) nor am I a quantum physicist (the micro). And I’m sure if any relevant occupation were to look into my analogy, there’d be tons of holes. I am merely a peripheral enthusiast.

quantum advice
My scribbles on paper which turned into this post.

#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!

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#unfiltered #5 The Insider “Silicon Valley” TV Show – The Show, plus Thoughts on Eccentric Cold Emails and Crazy Startup Pitches

Tech satire.

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.

So when I learned, from the most recent episode of Angel podcast, about David Cowan’s version, I just had to check it out. And I wish I had only discovered it sooner. Made by Director Martin Sweeney, and co-visionaries, Michael Fertik of Reputation.com and David Cowan of Bessemer Venture Partners, bubbleproof is tech hilarity… made by the folks who have tech day jobs. Though I still haven’t watched the 6 seasons and 53 episodes of the Silicon Valley TV series yet. Sorry, friends who keep recommending it.

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!

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#unfiltered #4 Namedropping and Intros – Why my default is to not to namedrop, Direct/Indirect Consequences, Making/Receiving Intros, and Notes on Friendship

namedropping and intros, fame
Photo by Einar H. Reynis on Unsplash

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:

  1. 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.
  2. 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.
  3. 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:

  1. Understand the deeper emotional spectrum,
  2. Ask pertinent follow-up questions,
  3. 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:

  1. We failed at bringing people closer together, fundamentally being comfortable with being vulnerable, at that event.
  2. 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!

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#unfiltered #3 Plan Bs – Should we have them?

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!

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#unfiltered #1 Urgency – Thoughts on Coronavirus, Innovation, Space Travel, and Love

unfiltered vc urgency

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 myself when 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.

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