A few weeks ago, around the time I published Am I At My Best Right Now?, I started noticing more and more that my friends, colleagues, and people that I’ve met since were going through tough times. Two lost a family member. Some were laid off. Two were forced to leave this land I call home. Four broke up. Three burned out. Countless more told me they were stressed and/or depressed, and didn’t know how to escape this limbo. After I published that post, another handful of people also reached out and courageously shared the troubles they are going through now. How it’s been so hard to share with others. And yesterday, while editing this blog post, I found out that one of my high school friends had passed.
Inspiration and Frustration
During this time, I had a thought: Frustration is the absence of inspiration. There were many times in my own life when I was beating myself up because I couldn’t think of a solution. And a small percent of those times, I didn’t even bother to think of a solution since I was so engrossed in my frustration with myself.
In these unprecedented times and inspired by the conversations around me, I decided to show that we’re not alone. So, I asked people who I deeply respect and who could shed light as to what it means to be human. I asked just two questions, but they were only allowed to answer one of them:
What is the one thing that inspires you so much that it makes everything else in life much easier to bear?
What is stressing/frustrating you so much right now that it seems to invalidate everything else you’re doing?
In turn, they responded via email, text, or on a phone call. Of the 49 I asked, so far, 31 responded with their answers. 4 politely turned me down due to their busy schedules. Another one turned me down because she didn’t feel like she could offer value in her answer.
26 responded with what inspires them. 5 with what frustrates them. All of whom I know has been through adversity and back.
Admittedly, the hardest part about this study was how I was going to organize all these responses. Unlike the one about time allocation I did over a month ago, where I knew exactly how to organize the data before I even got all the responses, this one, I really didn’t know how to best illustrate the candor everyone shared. In fact, I would be doing a disservice to them, if reduced their honesty and courage to be vulnerable to mere numbers. So, in the end, below, I let everyone speak for themselves. Sometimes, simplicity is the best.
Thank you to everyone who contributed to making this blog post happen, including Brad Feld, Mars Aguirre, Shayan Mehdi, Thomas Owen, Chris Lyons, Mark Leon, Jamarr Lampart, Christen Nino De Guzman, Louis Q Tran, Sam Marelich, Dr. Kris Marsh, Quincy Huynh, DJ Welch, Jimmy Yue, and many, many more heroes who helped me and the world around us behind the curtains.
Last week, I started building a Quora presence. Admittedly, I’ve been a long-time lurker, and only recent answer-er on the platform. Partly to practice sharing thoughts. Partly to answer more specific queries. And partly to have fun. Yes, fun.
It just so happened that I came across a curious question then.
As an entrepreneur, have you found that the cognitive biases (i.e., systematic deviations from rationality that affect human decision-making) described in this article affect the decisions you make for your business?
The question cited this article. And the article itself detailed on 3 of the many cognitive biases entrepreneurs (well, people in general) come across.
Confirmation bias – anything we see or hear that supports our own beliefs reinforces our beliefs, whereas the opposite sparks disagreement
Sunk cost fallacy – our tendency to continue to hold onto hope for bad investments
And, overconfidence – overestimating yourself and underestimating everyone else.
My answer
Simply, yes.
In fact, not just entrepreneurs, but most people are affected by the mentioned cognitive biases – confirmation bias, sunk cost fallacy/loss aversion, and overconfidence. It’s just that many people aren’t aware they have them, which can be detrimental to business, relationships, mental health, and more. I think the article even ranks the 3 from least noticeable to most noticeable from a self-assessment point of view. I’ll give an example of each – all of which I’ve seen before:
Confirmation bias – Stanford engineers are smart. → I will continue hiring Stanford engineers. The flip side is that you’ll be looking less into other populations of engineers who could also be amazing, like folks who are underrepresented and underestimated. Therefore, creating this self-perpetuating loop.
Sunk cost fallacy – I’ve hired this VP Sales that came highly recommended from multiple sources. But over the course of 6 months, I realized that this VP (1) couldn’t meet, much less beat, quota each quarter, and (2) has been unable to hire other great candidates to fulfill quota each quarter. But she will change. She’ll get better. She’ll grow into the role. While it’s okay to hire for passion, make sure candidates have at least a baseline of skills required for the role. And in a VP hire, a good proportion of the job description is hiring. The sunk cost here is the VP hire. While I don’t have to fire her, unless she’s really not doing her job at all, I need to find someone to top her who can perform in the role as fast as possible.
Overconfidence – My product is amazing; all of our competitors’ products suck. I’ve seen this way too often when founders pitch their startup. And while it’s great to be confident in your own product/team/yourself, it should never eclipse your perspective to value the work and commitment and results of others. A question I love asking founders who say “my product is amazing, everyone else is bad” is: What are your competitors doing right? If you were them, what would you say about your own product?
In closing
While these 3 are only a few among the myriad that plague our cognition (i.e. left digit bias, hindsight bias, anchoring bias, fundamental attribution error, etc.), hopefully, this post will shed a little light into the world of our own psychology. Sometimes before we can fix something, we have to first be aware of it.
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!
There’s a saying in venture that: “A-players hire A-players; B-players hire C-players.” Your ability to grow a business is often closely correlated with your ability to attract and acquire talent. But what does it mean to attract and hire world-class talent? Especially for functions you, as a founder, yourself may not be an expert in.
“A-players hire A-players; B-players hire C-players.”
How does a first-time founder how to vet a seasoned sales executive? Or on the flip side, how does a non-technical founder learn to differentiate a good AI engineer from a great AI engineer?
While even the best founders, leaders, and managers make hiring mistakes, hopefully this post can act as a reference point as to what to look for. And while I have yet to master the craft, I’ll borrow 5 lessons from some of the best that has served as a guiding principle for me and for some of the founders I’ve worked with.
5 Lessons from 4 of the Greatest
Hire passion; train skill.
Desire/obsession > passion.
And, the ephemeral nature of passion.
Hire VPs who can hire.
Attract and hire intentionally.
On building trust.
On scaling yourself.
To hire your best complements, ask people in your network 2 questions.
People seem to love origin stories – both in theatre and in life.
“How did it all start?”
“How did you get into this career?”
Or…
“How did you meet your wife/husband?”
And well, I can’t say I’m one to push back on that.
There’s something truly magical about “Once upon a time…”. And I’m no stranger to fairy tales. Growing up, I was largely influenced by older female cousins and family friends. As soon as our parents left to their wine-sipping adult gossip around a table of blackjack, my cousins and older female friends would drag us to watch their favorite Disney movies on the VCR, namely princess movies. I’m not exaggerating when I say I’ve seen Beauty and the Beast more than 100 times or Cinderella more than 50 times. In fact, my friends in elementary school would talk about their favorite movies – Transformers, LEGO Bionicles, Peter Pan, and Tarzan. Yet, mine was Disney’s 1998 Mulan.
And they all started with “Once upon a time…”
So, it was no surprise when friends, colleagues, and then strangers started asking me:
“How/when/why did you start hosting social experiments?”
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:
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.
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.”
#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!
One of my favorite thought exercises to do when I meet with founders who have reached the A- and B-stages (or beyond) is:
“What will his/her company look like if he/she is no longer there?”
The Preface
While the question looks like one that’s designed to replace the founder(s), my intention is everything but that. Rather, I ask myself that because I want to put perspective as to how the founder(s) have empowered their team to do more than they could independently. Where the collective whole is greater than the sum of its parts. Have the founders built something that is greater than themselves? And is each team member self-motivated to pursue the mission and vision?
“Well, Mr. President,” the janitor responded, “I’m helping put a man on the moon.”
From the astronaut who was to go into space to the janitor cleaning the halls of NASAs space center, each and every one had the same fulfilling purpose that they were doing something greater than themselves.
And if the CEO is able to do that, their potential to inspire even more and build a greater company is in sight. Can he/she scale him/herself? And in doing so, scale the company past product-market fit (PMF)?
For the purpose of this post, I’ll take scale from a culture, hiring, operating, and product perspective, though there are much more than just the above when it comes to scale. Answering the questions, as a founder:
How do you expand your audience?
How do you build a team to do so?
And, how do you scale yourself?
And to do so, I’ll borrow the insights of 10 people who have more miles on their odometer than I do.
While many of these lessons are applicable even in the later stages of growth, I want to preface that these insights are largely for founders just starting to scale. When you’ve just gone from zero to one, and are now beginning to look towards infinity.
The TL;DR
Build a (controversial) shocking culture.
Hire intentionally.
Retaining talent requires trust.
Build and follow an operating philosophy.
Create, hold, and share excitement.
Align calendars.
Upgrade adjacent users as your next beachhead.
Capture adoption by changing only 1 variable per user segment.
Last week, my mentor/friend asked me if I knew anyone who’s stellar at storytelling and would be willing to hold a 1-hour workshop about it with his mentorship group. I connected with my buddy who earned his chops podcasting and being a brilliant customer-oriented founder, specifically on the user journey.
And it got me thinking. Hmmmm, I wonder how long people take to prep for a workshop or talk designed to inform and educate. Which eventually led me to the question… How much time allocation might many event hosts underestimate when asking a speaker to speak at their event?
Well, outside of travel, set up, rehearsal time, and of course, the length of the talk/workshop itself.
So, over the last few days, I reached out to 68 friends, mentors, and colleagues who have been on the stage before, including:
VCs – who invest out of vehicles that range from $5M to $1B (sample-specific)
Angels – investing individuals, who have over $1M in net worth
Founders – both venture-backed and bootstrapped
Executives – Fortune 500 and startup
Journalists
Influencers – YouTubers and podcasters
Consultants/Advisors
Professors
And, those who’ve been on public stages with 1000+ in live viewership.
… and asked them 2 questions:
How long, in hours, do you take to prepare for a 1-hour talk?
For the purpose of slightly limiting the scope to this question, let’s say it’s on a topic you’re extremely passionate and well-versed in, and the audience is as, if not more, passionate than you are.
And if I said this was for a high-stakes event, that may change your career trajectory, would your answer change? If so, how long would you spend prepping?
50 responded, with numerical answers, by the time I’m writing this post, with a few results I found to be quite surprising. *pushing my nerd glasses*
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.
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:
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:
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?
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?
#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!
And I’m in complete accordance. I want to specifically underscore 2 of Michael’s sentences.
… and…
The only ‘exception’ to this ‘rule’ would be if investors themselves were the target market for the product. At the same time, I can see how the venture industry has led her and many others to believe otherwise. So I thought I’d elaborate more through this post.
A few days ago, I watched Yes Theory‘s recent heartwarming and inspiring video, Creating a Subscriber’s Viral Job Application. And if you have a spare 20, I highly recommend checking it out. Yesterday, I chatted with a friend about the influx of spam calls these days. So, I thought; now that’s a start of a #unfiltered blogpost.
As a warning, this post is slightly more eccentric than, admittedly, my average #unfiltered blog post.
Prefacing with spam
I used to write this newsletter, Friday Morning Coffee Break, back in college for one of the clubs I helped lead. (Now that I think about it, coffee seems to be the theme for my content drops.) So if any of you subscribers then are reading this post now, this anecdote will be a momentary skip down memory lane.
So, you see, I’m a huge fan of comedy. And 3 years back, when I first learned about James Veitch, I just had to try it out myself. Replying to spam emails. From Nigerian princes. Cold emails from ‘celebrities’. Confirmation emails that require replying to unsubscribe.
If you’re curious as to how he pulls it off, you can check out his Hilarious (yes with a capital ‘H’) TED talks: here, here, and here.
What I did
When I received:
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