Tag: tim ferriss

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#unfiltered #25 Meeting the Curiously Passionate and the Passionately Curious – The Why and The Where

travel, meeting people, rabbi sacks

“It’s the people not like us who make us grow.”

– Rabbi Lord Jonathan Sacks on The Tim Ferriss Show Ep. #455

I recently tuned into, at the time of writing this post, Tim Ferriss’ third most recent podcast episode, interviewing Rabbi Sacks. Although I’m a regular listener to the show, I wasn’t expecting much. I neither have a history of being religious nor spiritual – merely peripheral curiosity. Yet, I don’t hesitate for one second to say: It is, by far, one of the most insightful and enlightening podcast episodes I’ve heard in 2020. So, if you have a spare 1.5 hours, I highly recommend it, especially if you’re looking for a perspective shift on:

  • Leadership,
  • Seeking peer approval,
  • What a single cold “call”/visit could get you,
  • And the need for “cultural climate change” in the understanding between the balance of “I” and “we”.

And Rabbi Sacks masterfully weaves these concepts together. While my reaction will never do his insights justice, two other thoughts, each paired with their own story, I had to double click on:

“Good leaders create followers, great leaders create leaders.”

“What happens when you’re in a situation in which you have done something that has generated widespread disapproval? How do you deal with that?

“Win the respect of the people you respect.”

And I digress.

The Bubble

I’ve lived my entire life so far in the Bay Area, barring a few vacations and excursions here and there. I was born here. I went through 12 years of grade school here. 13 if you count kindergarten. And though I had the option of leaving the Bay for college, I ended up choosing a school here as well. Truth be told, I might as well have “Made in the Bay” stamped on my forehead.

I live in a bubble. But I know I breathe in one. Not just geographically, but educationally, racially, sexually, socioeconomically, and so on.

Being a shy introvert pre-adulthood didn’t help with broadening my perspective on life either. I still remember the days in high school when I dreaded the teacher calling on me. Clammy palms, cold sweat, rigid spine. I would never vocally question disagreement. Equally, I would rather be a people pleaser than cause what I deemed to be unnecessary friction. I was a seafood hors d’ouevres of perturbation.

So, by inspiration from a mentor, I took actionable steps to conquer my own demons. Meet one new person you’re extremely excited to meet every single week for a year.

While I still carry the artifacts of myself yesterday, learning to balance myself between the person I thought and think I needed to become and the person I was, I began my journey 6 years ago.

The Pop in the Bubble

I’d be fronting if I said I wasn’t scared shitless when I began. Though I don’t think everyone in the world has this dilemma, I’m confident I am not alone. I had and have all these scenarios playing in my head. A bunch of ‘what-ifs’. What if they think I’m too nosy? What if they don’t have time to respond? Or what if they hate me for bothering them?

They say it gets better over time. And they’re not wrong. But I still have that lingering, gnawing feeling whenever I click send or put myself out there. While, over the years, the fears never fully dissipated, I’ve learned to tango with discomfort. In the words of my mentor who inspired my journey:

“You’re never as good as they say you are, but you’re also not as bad as they say you are. And hell, you can’t even be bad if they don’t even know who you are.”

… which I believe he drew inspiration from Lou Holtz. Shortly after, I clicked the “Send” button at the bottom of my first ‘curiosity’ email. After all, like he said, what’s the worst that can happen? Getting ignored. And as such, I would be no better nor worse off than I was and am in that cross section in time. With that assurance, it eventually led me to find my cold email “template” and hosting social experiments, like Brunches with Strangers.

The Where

Over the past few weeks, a few new people asked me: “Where do you find these people to reach out to?” Although it’s not the first and I assume certainly not the last, I thought I’d share in the form of this post as a possible inspiration for how we can grow, if I were to paraphrase Rabbi Sacks.

While I don’t characterize myself as a voracious reader, I allot time every day and have found many of my Senseis in the form of literature and discourse – online and offline, printed and taped, and in-person and remote. Including:

  • Books
  • Online articles/press releases
  • Newsletters
  • YouTube videos
  • Movies
  • Podcasts
  • Webinars/fireside chats
  • Textbooks
  • And, other people

One level deeper

To look beyond my own horizon, I tune into Pocket‘s Discover tab, or a platform I’ve recently fallen in love with, Readocracy. You can check out what online reading I’ve been up to lately on my Readocracy profile. And I can’t wait, when I can start tracking the books I read and the podcasts I listen to on there. I’m also fortunate enough to have friends who read, write, listen, and socialize with different social and professional circles than I do and am in. And as I meet more people, the spectrum of topics and interests snowball upon each other, as we help each other see new perspectives – some of which we never thought were possible.

Admittedly, where I find who to reach out to is, by no means, special or esoteric. In topics, I look into ones I’m genuinely interested in, in that moment and predictably beyond, even if it’s only a month or two, as promiscuous as I might be for many. In my short phases of promiscuity, I nevertheless take deep dives. Deep, yet often, not long. At the same time, I have a small handful of evergreen interests, like:

  • The art and science of building relationships,
  • The art of creating irreplaceable memories,
  • Psychology and mental models,
  • Swimming and intense athleticism,
  • Art as a multi-faceted definition,
  • Startups,
  • Technology and what lies at its frontier,
  • The final frontier – outer space and its cosmological inhabitants,
  • And the future.

In people, I look for two things:

  1. Inflection points in their life. Oxymorons/ironies. Overt and covert contradictions.
    • If I were to make assumptions given their initial attributes (i.e. education, age, gender, geography, career, life choices/circumstances, etc.), would I have been able to predict where they are now?
    • Of course, in making these assumptions, it is also my responsibility to be aware and to tread carefully where I should. Unfortunately, ignorance is not an excuse. If I’m unsure, I err on the side of caution.
  2. Deep intellectual curiosity and passion. Whom I call the passionately curious and the curiously passionate.

In closing

While I’m prone to talking too much at times, during these moments, it is my duty and the highest form of respect I can offer, to listen. If I were to take it from a selfish note, I learn so much more when I listen. And in actively listening, and actively checking my biases, to respond with thoughtful questions.

So, I’ll close on more thing Rabbi Sacks said in his recent interview with Tim Ferriss:

“Safe space means that courteous discipline of respectful listening.”

Photo by Mantas Hesthaven on Unsplash

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

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

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#unfiltered #23 Twenty-Four Frames per Second – Jerry Colonna, The Illusion of Motion, Mental Health, and Radical Self-Inquiry

24 fps, film, questions about mental health

What appears fluid is twenty-four frames per second. Twenty-four precious moments per second, lived second after second after second. And each of those still moments is imbued with feelings and memories. The rapid fluidity of each of those moments defines the patterns and beliefs that, in turn, define our lives.

Our lives are twenty-four frames per second, with each frame a set piece of feeling, belief, obsession about the past, and anxiety about the future. Neither good nor bad, these frames form us. They become the stories we tell ourselves again and again to make sense of who we’re becoming, who we’ve been, and who we want to be.

Ghosts of our pasts – our grandparents and their grandparents as well as the ghosts of their lives – inhabit the frames. They and their beliefs, interpretations of scenes, words, and feelings haunt the frames of lives as surely as the roses, figs, and lemon drops of our present daily lives do.

Slowing down the movie of our lives, seeing the frames and how they are constructed, reveals a different way to live, a way to break old patterns, to see experiences anew through radical self-inquiry.

– Jerry Colonna in Reboot: Leadership and the Art of Growing Up Chapter 1: Passing GO

Who is Jerry Colonna?

I recently had the fortune of having an email exchange with one of the greatest household names in the space of startups and venture capital, especially known for his empathy and candor. A name synonymous with mental health, accelerators and being radically honesty about his journey – professional and personal. In our chat on mental health, he highly recommended Jerry Colonna‘s book, where the above passage comes from. So I just had to get it.

I first heard of Jerry on Harry Stebbing’s Twenty-Minute VC (his most recent episode with the CEO Whisperer) and The Tim Ferriss Show. And over the years, possibly as a result of confirmation bias, I’ve heard his name pop up over and over again from various founders and VCs. Over the decades, many people know Jerry as:

  • A venture capitalist,
  • An executive coach,
  • Co-founder of New York’s Flatiron Partners,
  • Partner at JP Morgan,
  • Founder of Reboot,
  • And, probably best known now for being the CEO whisperer.

So far, his book has reflected all the above and more.

A short trip down memory lane

Although we’re used to 60 frames per second (fps) for daily use or 120 fps for movies these days, the illusion of motion was first found at the optimal 16 fps. Early silent films, like Charlie Chaplin films, were then sped up to 24 fps, as far back as 1927. Admittedly, part of the reason as to why they seemed so comical. As technology caught up, still, the de facto frame rate was 24 fps.

In 2012, The Hobbit series was shot in 48 fps. In 2016, Bill Lynn’s Long Halftime Walk was shot and projected in 120 fps. Gemini Man, which came to theaters 3 years later, followed suit. James Cameron also plans to shoot Avatar 2 at 60fps, with the goal of maximizing the feel of a 3D-world. But as both filmmakers and animators approach higher and higher frame rates, there have been and will continue to be the effect of the uncanny valley. Uncanny valley, or in other words, the more something artificial looks to be real, the more our minds try to reject its appearance. Subsequently, making certain objects, robots, or animations seem creepy and chilling. Part of the reason, it’s a ‘hell no’ to horror films for me.

After decades of 24 fps films, it’ll take a while before our minds catch up to what we see. But I digress.

Moving Forward

Just like how silent films shot at 12-16 fps were shown at 24 fps, giving its comical effect, many of us, myself included (until 3 years back), live by weaving narratives between cross sections of time – both in our personal lives and in our careers. And we script our biographies in a format where seemingly everything happened for a reason. Maybe some things did.

But on the other hand, maybe you’re like me. Where I don’t know what the hell is going to happen tomorrow. Yes, I tell myself I have these plans and goals in life I’m working on accomplishing. But if you ask me, what pitfalls are up ahead? I haven’t even thought about half of them. Another quarter, and I’m being generous to myself here, I think I have a good grasp on, but knowing myself, I’ve got about 20% of it down, 80% I’m missing some piece of the puzzle.

After all, as Warren Buffett once said,

“The rear view mirror is always clearer than the windshield.”

The last quarter – I’m scared – really scared for. But, what’s life without a bit of risk and adventure?

Moving in the Present

While it’s easy to build that narrative for the trail behind us, it’s hard to forecast the narrative forward. So, I take life play by play – frame by frame. Slowing down to that 16 fps, examining, like Jerry suggests, my life in real time. Savoring and reflecting on every moment – the good and the bad. Reexamine my biases – the overt and the covert, in the words of a brilliant sociology professor I chatted with last week. ‘Cause they will make who I am tomorrow.

So, I’ll end on 2 big questions, inspired by that professor. 2 questions I plan to answer and reexamine every month:

  1. What do your social circles look like?
    • Professional? Personal?
    • How did you meet them? How often do you stay in touch with them?
    • What beliefs – overt and covert- are they reinforcing? Are these beliefs worth reinforcing?
  2. Now that you know, what are you willing to give up to make it happen?
    • Are you willing to take radical measures to do so?
    • What do you say that you don’t mean? Or find it hard to follow through on?

Photo by Kushagra Kevat on Unsplash

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

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

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#unfiltered #18 Naivety vs Curiosity – Asking Questions, How to Preface ‘Dumb’ Questions, Tactics from People Smarter than Me, The Questions during Founder-Investor Pitch

asking questions, naivete vs curiosity, how to ask questions

Friday last week, I jumped on a phone call with a founder who reached out to me after checking out my blog. In my deep fascination on how she found and learns from her mentors, she shed some light as to why she feels safe to ask stupid questions. The TL;DR of her answer – implicit trust, blended with mutual respect and admiration. That her mentors know that when she does ask a question, it’s out of curiosity and not willing ignorance – or naivety.

But on a wider scope, our conversation got me thinking and reflecting. How can we build psychological safety around questions that may seem dumb at first glace? And sometimes, even unwittingly, may seem foolish to the person answering. The characteristics of which, include:

  • A question whose answer is easily Google-able;
  • A question that the person answering may have heard too many times (and subsequently, may feel fatigue from answering again);
  • And, a question whose answer may seem like common sense. But common sense, arguably, is subjective. Take, for example, selling losses and holding gains in the stock market may be common sense to practiced public market investors, but may feel counter-intuitive to the average amateur trader.

We’re Human

But, if you’re like me, every so often, I ask a ‘dumb’ question. Or I feel the urge to ask it ’cause either I think the person I’m asking would provide a perspective I can’t find elsewhere or, simply, purely by accident. The latter of which happens, though I try not to, when I’m droning through a conversation. When my mind regresses to “How are you doing?” or the like.

To fix the latter, the simple solution is to be more cognizant and aware during conversations. For the former, I play with contextualization and exaggeration. Now, I should note that this isn’t a foolproof strategy and neither is it guaranteed to not make you look like a fool. You may still seem like one. But hopefully, if you’re still dying to know (and for some reason, you haven’t done your homework), you’re more likely to get an answer.

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Candor Comes First – How to Navigate Tough Conversations

relationship, candor, truth, how to navigate tough conversations

The other day, I jumped on a call with a friend who was going through a speed bump in his relationship. Though I’m no behavioral scientist nor expert in all matters regarding relationships, I’ve been privy to cousin cases between other couples, dorm-mates and roommates, as well as startup teams. And like most people out there, I’ve been through my fair share as well.

From my own experience, as well as from being a fly on the wall to others’, a large portion of the drama starts with the time spent dancing around the elephant in the room. And the longer a pair (or more) dances, the worse it gets. At the same time, it’s easier said than done. Rationally, we know that we should start with the truth. But frankly, it’s hard for many of us, myself included, to speak the truth when we need to. And in my hesitation, I usually regress to thinking: “Maybe it’ll get better over time. Maybe he/she will just forget about it. Maybe someone else will solve it in my place.”

Though I’ve gotten better at getting straight to the point, I’ve, by no means, mastered my approach.

Last week, I tuned into Elizabeth Gilbert, #1 New York Times bestselling author of Eat, Pray, Love and Big Magic, on her recent episode with Tim Ferriss. Quoting her late lover, Rayya Elias, at the 13:48 mark of the episode, Elizabeth shares this brilliant comment:

“The truth has legs. It’s the only thing that will be left standing at the end of the day… And since that’s where we’re going to end up, why don’t we just start with it?”

The Boiling Frog Problem

As all drama goes, we end up beating ourselves and others up in the process. Yet, when the dust settles, we still come back to the one left standing. There’s a similar concept that I learned in a college business course called the boiling frog problem.

If you put a frog in boiling water right away, it’ll jump out. But if you put the frog in lukewarm water and slowly heat it up, it won’t notice until it’s too late. And for the sake of the analogy, end up dying in the latter case.

The emotional turmoil we go through in our daily lives is no exception. It’s much easier to address the problem from the get-go, then let it rot you inside out. To put it into perspective, let’s say you address the problem at the beginning. There are only two outcomes possible:

  1. It’s not as bad as you expected, and you’re able to resolve it easily.
  2. It’s just as bad as you thought it’d be (as your mind regresses to the worst case possible). And well, you get burnt, as expected. But you will come out as a stronger person than when you went in. A phoenix reborn.

In closing

In tricky times, many of our relationships have been put on the rocks. The important part isn’t the conflict itself, but how we resolve the conflict. A frame of mind where there is no blame to dish out, but taking mutual responsibility to come out stronger in finding the resolution. Mike Maples Jr, co-founder of Floodgate, one of the most successful VC firms in the Valley, once said:

“Ego is about who’s right. Truth is about what’s right.”

Photo by Alex Iby on Unsplash

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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The Best Way I’ve Heard to Ask “What did you learn?”

how to say no, learning

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:

  1. How much do you value an opportunity?
  2. 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.

Taking it a step further

Josh Waitzkin, author, chess champion, and martial arts champion, on Episode #412 of the Tim Ferriss Show, puts it quite elegantly:

“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?

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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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The Marketplace of Startups

books about startups

Over the past decade, stretching its roots to the dot-com boom, there have been more dialogue and literature around entrepreneurship. In a sense, founding a business is easier than it’s ever been. But like all things in life, there’s a bit more nuance to it. So, what’s the state of startups right now?

Lower Barriers to Entry

A number of factors have promoted such a trend:

  • There are an increasing number of resources online and offline. Online courses and ed-tech platforms. Fellowships and acceleration/incubation programs. Investor office hours and founder talks. YouTube videos, online newsletters, and podcasts.
  • The low-code/no-code movement is also helping bridge that knowledge gap for the average person. Moreover, making it easier for non-experts to be experts.
  • The gig economy have created a fascinating space for solopreneurship to be more accessible to more geographies.

Demand (by consumers and investors) fuels supply of startups, through knowledge and resource sharing. Likewise, the supply of startups, especially in nascent markets, fuels demand in new verticals. So, the ecosystem becomes self-perpetuating on a positive feedback loop. As Jim Barksdale, former Netscape CEO, once said:

“There are only two ways I know of to make money – bundling and unbundling.”

BundlingUnbundling
Market MaturityMarket Nascency
HorizontalizationVerticalization
BreadthDepth
Execution Risk
Bias		Market/Tech Risk
Bias

Right now, we’re at a stage of startup market nascency, unbundling the knowledge gap between the great and the average founder. This might seem counter-intuitive. After all, there’s so much discourse on the subject. There’s a good chance that you know someone who is or have thought about starting a business. But, I don’t believe we’re even close to a global maximum in entrepreneurship. Why?

  1. Valuations are continuing to rise.
  2. Great founders are still scarce.
startup growth
Photo by Isaac Smith on Unsplash

Valuations are shooting up

Valuations are still on the rise. Six years back, $250K was enough runway for our business to last until product-market fit. Now, a typical seed round ranges from $500K-$2M. A decade ago, $500M was enough to IPO with; now it only warrants a late-stage funding round. By capitalistic economic theory, when a market reaches saturation, aka perfect competition, profit margins regress to zero. Not only are there still profits to be made, but more people are jumping into the investing side of the business.

Yes, increasing valuations are also a function of FOMO (fear of missing out), discovery checks (<0.5% of VC fund size), super duper low interest rates (causing massive sums of capital to surge in chase yields), and non-traditional venture investors entering as players in the game (PE, hedge funds, other accredited investors, (equity) crowdfunding platforms). It would be one thing if they came and left as a result of a (near) zero sum game. But they’re here to stay. Here’s a mini case study. Even after the 2018 drop in Bitcoin, venture investors are still bullish on its potential. In fact, there are now more and more specialized funds to invest in cryptocurrency and blockchain technology. Last year, a16z, one of the largest and trendsetting VC players, switched from a VC to an RIA (registered investment advisor), to broaden its scope into crypto/blockchain.

Great founders are scarce

“The only uncrowded market is great. There’s always a fucking market for great.”

– Tim Ferriss, podcaster, author, but also notably, an investor and advisor for companies, like Facebook, Uber, Automattic and more

Even if founders now have the tools to do so, it doesn’t mean they’ll hit their ambitious milestones. For VCs, it only gets harder to discern the signal from the noise. Fundamentally, there’s a significant knowledge delta – a permutation of misinformation and resource misallocation – in the market between founders and investors, and between average founders and great founders.

The Culinary Analogy

Here’s an analogy. 30 years prior, food media was still nascent. Food Network had yet to be founded in 1993. The average cook resorted to grandma’s recipe (and maybe also Cory’s from across the street). There was quite a bit of variability into the quality of most home-cooked dishes. And most professional chefs were characteristically male. Fast forward to now, food media has become more prevalent in society. I can jump on to Food Network or YouTube any time to learn recipes and cooking tips. Recipes are easily searchable online. Pro chefs, like Gordon Ramsay, Thomas Keller, and Alice Waters, teach full courses on Masterclass, covering every range of the culinary arts.

Photo by Brooke Lark on Unsplash

Has it made the average cook more knowledgeable? Yes. I have friends who are talking about how long a meat should sous vide for before searing or the ratio of egg whites to egg yolks in pasta. Not gonna lie; I love it! I’ll probably end up posting a post soon on what I learned from culinary mentors, friends, and myself soon.

Is there still a disparity between the average cook and a world-class chef? Hell ya! Realistically I won’t ever amount to Wolfgang Puck or Grant Achatz, but I do know that I shouldn’t deep fry with extra virgin olive oil (EVOO) ’cause of its low smoke point.

Great businesses are scarcer

The same is true for entrepreneurship. There are definitely more startups out there, but there hasn’t been a significant shift in the number of great startups. And the increase in business tools has arguably increased the difficulty to find business/product defensibility. It’s leveled the playing field and, simultaneously, raised the bar. So yes, it’s easier to start a business; it’s much harder to retain and scale a business.

It’s no longer enough to have an open/closed beta with just an MVP. What startups need now is an MLP (minimum lovable product). Let’s take the consumer app market as an example.

The Consumer App Conundrum

Acquiring consumers has gotten comparatively easier. Paid growth, virality, and SEO tactics are scalable with capital. More and more of the population have been conditioned to notice and try new products and trends, partly as a function of the influencer economy. But retaining them is a different story.

So, consumers have become:

  1. More expensive to acquire than ever before. Not only are customer acquisition costs (CAC) increasing, with smaller lifetime values (LTV), but your biggest competitors are often not directly in your sector. Netflix and YouTube has created a culture of binge-watching that previously never existed. And since every person has a finite 24 hours in a day, your startup growth is directly cutting into another business’s market share on a consumer’s time.
  2. And, harder to retain. It’s great that there’s a wide range of consumer apps out there right now. The App Store and Play Store are more populated than they’ve ever been. But churn has also higher now than I’ve seen before. Although adoption curves have been climbing, reactivation and engagement curves often fall short of expectations, while inactive curves in most startups climb sooner than anticipated. Many early stage ventures I see have decent total account numbers (10-30K, depending on the stage), but a mere 10-15% DAU/MAU (assuming this is a core metric). In fact, many consumers don’t even use the app they downloaded on Day 2.

Luckily, this whole startup battlefield works in favor of consumers. More competition, better features, better prices. 🙂

So… what happens now?

It comes down to two main questions for early-stage founders:

  1. Do you have a predictable/sensible plan to your next milestone? To scalability?
    • Are you optimizing for adoption, as well as retention and engagement?
      • With so many tools for acquisition hacks, growth is relatively easy to capture. Retention and engagement aren’t. And in engagement, outside of purely measuring for frequency (i.e. DAU/MAU), are you also measuring on time spent with each product interaction?
    • How are you going to capture network effects? What’s sticky?
      • Viral loops occur when there’s already a baseline of engagement. So how do you meaningfully optimize for engagement?
    • From a bottom-up approach (rather than top-down by taking percentages of the larger market), how are you going to convert your customers?
    • How do you measure product-market fit?
  2. What meaningful metric are you measuring/optimizing?
    • Why is it important?
    • What do you know (that makes money) that everyone else is either overlooking or severely underestimating?
    • What are you optimizing for that others’ (especially your biggest competitors) cannot?
      • Every business optimizes for certain metrics. That have a set budget used to optimize for those metrics. And because of that, they are unable to prioritize optimizing others. So, can you measure it better in a way that’ll hold off competition until you reach network effects/virality?

Building a scalable business is definitely harder. And to become the 10 startups a year that really matter is even more so. By the numbers, less likely than lightning striking you. In my opinion, that just makes trying to find your secret sauce all the more exciting!

If you think you got it or are close to getting it, I’d love to chat!

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