Category: People/Team/HR

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2020 Year in Review

I’ve written 102 essays on this blog in the past year, plus some change, spending an average of 1-2 hours per piece and a range from 30 minutes to 2 weeks. An average of 1,200 words per post. While not mutually exclusive, over half of which were on startup topics. One in three described the venture capital landscape. 36 (excluding #0) #unfiltered blog posts, where I share my raw, unfiltered thoughts about anything and everything. 16 on mental health. A surprising 13 on cold emails and its respective ecosystem. And my first public book review. Some didn’t age well, like The Marketplace of Startups. Some will stay evergreen.

25% of my blog posts I started writing at least 48 hours before the publish date. 1 in every 3 (-ish) of the afore-mentioned, I rewrote because I didn’t like the flow. For every 2 essays I wrote, 1 of which I had to wrestle deeply with the thought of imperfection. In effect, half of my essays were a practice to overcome my own mental stigma of “writer’s block.” Yet after over a year of writing, I realize that I’ve become prouder of my writing than when I started.

So, as the year is transitioning into the next, I thought I’d take some time to reflect on my growth 100 (+2) posts after starting this blog. Let’s call them superlatives.

Top 10 most popular

Ranked by total views per post, the 10 posts readers visit the most.

  1. #unfiltered #30 Inspiration and Frustration – The Honest Answers From Some of the Most Resilient People Going through a World of Uncertainty – I asked 31 people I deeply respect to share some of their greatest drivers and darkest moments in life and how they got through them. You can find part 2 here with 10 more thoughts.
  2. My Cold Email “Template” – My friends have asked me for years what I write in my cold emails, and now, what and how I write my cold outreaches are available for your toolkit.
  3. Fantastic Unicorns and Where to Find Them – An essay on the parameters and the mental models investors use to find “unicorn” startup ideas.
  4. When Investor Goodwill Backfires – What It Means to be Founder-Friendly and Founder-Investor Fit – How founders can do investor diligence before signing the term sheet and also how to best manage founder-investor dynamics
  5. #unfiltered #24 How long do you take to prepare for a talk? – A Study about Time Allocation
  6. How to Build Fast and Not Break (As Many) Things – A Startup GTM Playbook
  7. 10 Letters of Thanks to 10 People who Changed my Life – Every holiday season I write thank you letters to the people I deeply respect. It’s one of the best times of the year to reconnect. These are the letters I wrote in 2019. Here are also some I wrote this year for more context.
  8. #unfiltered #18 Naivety vs Curiosity – Asking Questions, How to Preface ‘Dumb’ Questions, Tactics from People Smarter than Me, The Questions during Founder-Investor Pitch
  9. #unfiltered #11 What I Learned About Building Communities through Social Experiments – Touching Jellyfish, Types of Social Experiments, The Thesis, Psychological Safety and Fairness
  10. The Marketplace of Startups – While many of the remarks on this blog post are now obsolete, largely incited by the 2020 Black Swan event – COVID, the two questions at the end of the blog post are the two I still like to ask founders today.

Personal favorites

While not every one of these got the limelight I had hoped, each of these are ones I felt great pride in being able to write on.

Most challenging to write

I had been wrestling with how vulnerable I can allow myself to be in the public space. Writing this post was frightening, but I’m glad I did. It cascaded into deeper conversations with my friends, colleagues and readers, but also inspired more blog posts after this about mental health.

#unfiltered #26 Am I At My Best Right Now?

In closing

I first started this blog with the intention of chronicling my own learnings in the amazing world of venture. While I couldn’t guarantee it would be helpful to every individual reading my humble meandering, I could, at least, guarantee what I write has been or continues to be instructive for me.

Within the first month it had evolved into an FAQ and a means to provide value to as many founders as I can when one day the number of people I want to help exceed my available bandwidth. Wishful thinking at the time, but a cause that inspired me forward. After the first six months, with the introduction of the #unfiltered series, I began to write to think – a way to flush out simple, unrefined ideas to more robust concepts. While I’ll forever be a work in progress, I began to make new dendrite connections that never existed before. In a way, I was and am still chronicling my own journey in hopes that it will continue to guide people beyond my immediate sphere of influence.

Thank you, each and every one of you, for accompanying me on this journey we took yesterday and the one we’ll take tomorrow. And I hope this cognitive passport will continue to serve as your cup o’ Zhou (/joe/) weekly.

Cheers, and I’m excited for the adventure ahead!

Photo by Ray Hennessy on Unsplash

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How Do We Welcome the Founder Narratives Behind the Curtains

Being a founder is one of the toughest jobs in the world. Resilience and grit are two (or one) of the indispensable traits of a 5-star entrepreneur. And most, if not all, investors establish grit as the baseline in founder selection, as opposed to the topline in various other careers. While I don’t mean to discount other career paths, all of which I have incredible admiration for, I can only speak in the world of venture where I spend most of my time in.

Yet that same persistence could very much be the same double-edged sword that makes or breaks you. In October, Ryan Caldbeck wrote about his decision to step down as CEO of CircleUp. It was and is one of the most candid pieces I’ve read about the founder journey to date. In it, one section particularly stood out. “Persistence was my superpower. But now I’ve now come to understand that persistence is a double-edged sword, and my decision not to take a break, to not take more off my plate, hurt me, my family and the company. That was the biggest mistake of my career.”

In the founder journey, there exist many moments a founder’s resilience is stress-tested. To get their first customer. To scale to a team of 10. 30. 100. To get their first investor. To raise their first institutional round. But the last thing a founding team needs is for some of their greatest evangelists – their investors – to create counterproductive friction. While it’s presumptuous of me to say that all friction is counterproductive, some friction and additional perspective is necessary to help founders make better, more informed decisions.

In his same essay, Ryan shares a feedback email he wrote to his former board member, as that member’s participation in the company had become “counterproductive”, “vindictive”, and even “destructive”. Unfortunately, these stories happen more often than I would like. It is why many founders believe investors are the gatekeepers to their startup’s success. But we’re not. We don’t have the right to be. On the same token, that’s exactly why it’s so important for founders to deeply consider founder-investor fit.

Michael Freeman found in 2017 that entrepreneurs are 50% more likely to report a mental health condition. Being a founder is lonely. But it doesn’t have to be.

Anton Ego’s words

A few weekends back, my friend and I re-watched my favorite movie. And as the movie faded into music, Anton Ego’s words echoed in my head. While it’s not the first time this quote has appeared in the venture world, it certainly won’t be the last:

“In many ways, the work of a critic is easy. We risk very little, yet enjoy a position over those who offer up their work and their selves to our judgment. We thrive on negative criticism, which is fun to write and to read. But the bitter truth we critics must face is that, in the grand scheme of things, the average piece of junk is probably more meaningful than our criticism designating it so. But there are times when a critic truly risks something, and that is in the discovery and defense of the new. The world is often unkind to new talent, new creations. The new needs friends.

“Last night, I experienced something new, an extra-ordinary meal from a singularly unexpected source. To say that both the meal and its maker have challenged my preconceptions about fine cooking is a gross understatement. They have rocked me to my core. In the past, I have made no secret of my disdain for Chef Gusteau’s famous motto: ‘Anyone can cook.’ But I realize, only now do I truly understand what he meant. Not everyone can become a great artist, but a great artist can come from anywhere. It is difficult to imagine more humble origins than those of the genius now cooking at Gusteau’s, who is, in this critic’s opinion, nothing less than the finest chef in France. I will be returning to Gusteau’s soon, hungry for more.”

For VCs

One of my favorite investors often says, “stay positive, test negative.” While the greatest strength an entrepreneur can have may be grit, the greatest strength an investor can have is optimism.

Optimism in the world. In markets. In startups. But especially people. That even if one venture doesn’t work out, for the people I’ve had the opportunity to stand behind, I know one of their pursuits eventually will. It’s only a matter of time and luck.

That same optimism is a leading indicator for open-mindedness. As people who build our careers at the top of the funnel, it is our obligation to cast our net outside of what is most familiar to us. There will be a number of ideas and belief systems entrepreneurs have that challenge our own. And in many ways they should, as founders are on the frontlines of innovation, they are aiming to be “right on the non-consensus“, to quote Andy Rachleff. When I first got into VC, that same investor who said “stay positive, test negative”, shared another word of advice, “Some of the best ideas seem crazy at first.“

George Bernard Shaw once said something similar as well, “The reasonable man adapts himself to the world; the unreasonable one persists in trying to adapt the world to himself. Therefore, all progress depends on the unreasonable man.”

Optimism isn’t only isolated to ideas, but also to the people – the “unreasonable” women and men – behind those ideas and the decisions they make. These innovators aren’t perfect, yet somehow many of us expect them to be. And that dichotomy has created this unfair dynamic that stunts innovation more than we think. I have so much respect for the funds that have set aside capital to invest in founders’ wellbeing, like Felicis Ventures, Freestyle, Crosscut, and more. And I hope many more will follow.

The stories we tell

Over the past few months, I’ve had a number of conversations with founders, friends, and readers about “mental fitness” and “emotional hygiene”. If I could borrow two of my friends’ vernacular. And I’ve learned that we humans are such amazing storytellers.

These powerful narratives has kept the human race alive all these millennia. Before the written word, it was the art of the spoken word, passed down from generation to generation, that held tales of ancestral origins of where to hunt and where to migrate to each season. The same stories have started and ended wars. They have helped us conquer impossible odds. Some narratives today are compelling enough for us to buy a new product or to end a conglomerate.

Yet these exact stories, especially the ones we tell ourselves, can cause stress, anxiety, and depression. The ones that the people we care about and respect tell us can carry even more weight. From role models, parents, managers, friends, mentors, teachers, peers, and more.

In closing

I realized, in conversation, these past few autumn months, more than ever, the power of sharing those stories. To share that we’re not alone and that together, we may learn more than the sum of our individual parts. I understand that it’s no easy task. Even for myself, I debated for the longest time whether to share that I’m not at my best right now. But I’m glad I did. The feedback from the people around me I’ve gotten since brought forth clarity and solace. Similarly, six of my friends, who publicly shared how they get through their toughest times (Pt 1, Pt 2), told me after how grateful they were to have an enormous weight lifted off their shoulders.

Top photo by Nong Vang on Unsplash

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The Biases Entrepreneurs can Carry

backlit beach clouds dark

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.

Photo by Pixabay on Pexels.com

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A Startup Hiring Philosophy

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

  1. Hire passion; train skill.
  2. Desire/obsession > passion.
    • And, the ephemeral nature of passion.
  3. Hire VPs who can hire.
  4. Attract and hire intentionally.
    • On building trust.
    • On scaling yourself.
  5. To hire your best complements, ask people in your network 2 questions.
    • Who to ask? And what’s next?
Continue reading “A Startup Hiring Philosophy”
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On Scale – Lessons on Culture, Hiring, Operating, and Growth

flower, scale

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?

It reminds me of the story of a NASA janitor’s reply when President Kennedy asked: “Hi, I’m Jack Kennedy. What are you doing?”

“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

  1. Build a (controversial) shocking culture.
  2. Hire intentionally.
  3. Retaining talent requires trust.
  4. Build and follow an operating philosophy.
    • Create, hold, and share excitement.
    • Align calendars.
  5. Upgrade adjacent users as your next beachhead.
  6. Capture adoption by changing only 1 variable per user segment.
Continue reading “On Scale – Lessons on Culture, Hiring, Operating, and Growth”
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#unfiltered #13 The Unlikely Marriage of Cuisine and Team-Building – Flavor Maps, Food Pairings and Bridgings, and How it Relates to Systems Thinking

broccoli, flavor mad science, recipes, team building tips

I met a founder (let’s call him Stan) recently who was about to close on his first big executive hire into a team less than 10 strong. Naturally, I asked what the rest of his team thought of that person. Stan replied, “I haven’t asked them yet.”

So, I subsequently followed up, “Were they able to meet him?”

“He’s been by our office, and I’m sure he’s had the chance to chat with them already.”

When he said that, two things stuck out to me:

  1. Stan’s use of “I’m sure…” implied neither that he was sure nor that he took care to verify.
  2. He seemed to have skipped a fundamental step in building a team. And by transitive property, how it would define his team’s culture.

The Culinary Parallel

Synonymously, a day later, my friend asked me, “How do you come up with your ideas for flavor mad science?”

You’re probably here thinking: “What the hell does this have to do with team-building and culture?” But bear with me here. I swear there’s a parallel.

Although, like all of my ideas and insights, I can’t say any of my flavor experiments are truly original, I always start off at the drawing board with flavor maps. And, you guessed it! Not even the concept of flavor maps is original. A few years ago, an amazing chef taught me this very trick of how he concepts new recipes every season at his critically acclaimed restaurant.

So, what’s a flavor map?

The idea of a flavor map is to start with a core ingredient – the star of your dish. And then slowly add other flavors and elements onto your diagram one by one. The catch is that every new flavor you add has to pair well with every single other flavor on that diagram.

Two flavor maps where I used green tea as the (co-)core ingredient.

Personally, I just try to think of a dish that I enjoyed, or know many other people enjoy, as the basis for a drawing a line between a pair. The reason I do so is that many generations of experts before me have already done the legwork to make these flavors work. And I’m just iterating off of their discoveries.

The more scientific approach is through flavor networks – specifically food-pairing and food-bridging. In summary, food-pairings are when you combine two ingredients with the same flavor molecules, like cheese/bacon or asparagus/butter. The most bizarre one in a 2011 Harvard study is probably blue cheese/chocolate, which share 73 flavors. On the other hand, food-bridging is when you take two ingredients that don’t share any flavors, like apricots/whiskey, and bridge them with an ingredient that shares commonalities with both, like tomatoes.

Yong-yeol Ahn and his colleagues explore the nuances of flavors and recipes in their 2011 research, which you can find here. But if you want the abridged summary, there’s a great one on Frontiers. Yet, as one of the co-owners of a critically-acclaimed molecular gastronomic restaurant told me not too long ago, take the research with a grain of salt. Food science is still extremely nascent and lacks consistent data points, especially across cultures.

Looping Back

Just like a complete flavor map has all of its ingredients working in cohesion with one another, a strong team needs to hold the same level of trust and respect. I’m not advocating that you need to agree with everyone on your team. In fact, disagreement on warranted grounds is better. But to be a well-oiled machine, a team can only be agile if you reduce the unnecessary friction that may exist now or arise in the future.

Although it is important that every team member can ‘food-pair’ with every other member, what I believe is more important is to have a fair mitigation system to ‘food-bridge’ all current and future disagreements. A system to resolve disputes and to prioritize tasks at hand. To have not only trust in each other, but also in the system design.

The cherry on top

Of course, I don’t know if Stan just forgot to set up times for his team to meet with the potential hire between his various tasks of running a business. Or if he had something he wanted to hide from his team. Regardless, his decision, or I guess, lack thereof to do so, would be detrimental to the delicate string of trust that connected his team to him.

To his and every other founders’ credit, there are often matters that seem obvious to an observer, but less so, when one has skin in the game – some degree of emotional attachment. And the deeper one is in the weeds, the harder it may be to follow rational behavior. Loosely analogized to the boiling frog problem. That said, some actions are excusable. These can often be caught by either a mentor or a close friend/family member. But there are a handful that aren’t. The same can be said on a macroscopic perspective as well. Between friendships. Lovers. Coworkers. You name it.

And, luckily for Stan, this falls under the former.

Top Photo by Hessam Hojati 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 #11 What I Learned About Building Communities through Social Experiments – Touching Jellyfish, Types of Social Experiments, The Thesis, Psychological Safety and Fairness

jellyfish, social experiment, psychological safety, how to build a community
Are these jellyfish friendly or not? Will they “bite”?

As colorful and as beautiful jellyfish are, we are still scared of the possible danger that each possess. So, most of us only admire them from afar. And for many of us who have seen some, we’ve watched them float gracefully in dark blue aqueous solutions across a sometimes distorted film of glass. These beautiful mysteries of the deep blue.

To Touch the Jellyfish

Much like my fascination every time my parents brought me to the aquarium as a kid, I’ve been fascinated with the people around me. Especially about the thin, sometimes distorted, film between these exceptionally fascinating souls and me. The distortion created as a function of society’s, as well as their own, efforts.

Exactly a year and two months ago, I embarked on a journey to host small-scale social experiments, like:

  • Hidden Questions. A game where no one else knows the question, except for the person answering it. And where the person answering has the choice of sharing the question that inspired the answer or taking it to the grave by taking a shot of hot sauce (about a 700,000 on the Scoville scale, for reference) or a variable number of Beanboozled beans.
  • Brunches with Strangers. Quite literally, Saturday brunches with strangers. Hosting a cast of people from all walks of life. Like founders, street artists, astrophysicists, concept artists, athletes, criminal investigators, filmmakers, college drop-outs, and much more.
  • The Curious Case of Aliases. Where players (strangers to each other) under aliases guess each other’s hobbies, occupations, deepest fears, etc. after only playing in a 30-minute game session. For instance, skribbl.io. Cards Against Humanity. Codenames. And Mafia.
  • And, the most recent addition to my small Rolodex of social experiments, Improv Presentations. A TED talk-like night where people present someone else’s creatively esoteric slide decks, with no context as to what’s in the deck until they’re on “stage”. To the postmortem dismay of my cheeks and core, we saw everything from how to survive a cat-pocalypse to how to master the art of DM’ing using military tactics to how to be a good plant parent.

The Thesis, The Questions

As COVID would have it, the lack of in-person interaction and self-quarantine inspired the last two. Yet, all of which with the same thesis: helping make the world feel a little smaller, a little closer, and a whole lot more interesting. Starting not with the people who bathe in the limelight, but with the people directly around me.

Why is it so hard to be candid with strangers? And sometimes, even harder with family and friends?

Do we need alcohol, drugs, crazy incidents, violence, a lack of sleep, or stress to truly be ourselves?

Though not all-encompassing, people seem to be naturally curious about things, events, status, money, and gossip. Why aren’t people more curious about people – well, as just themselves? Like me, you’ve probably posed and have gotten the question: “How are you?” or “How are you doing?”. And likely, with more times than one is willing to admit, we didn’t really care about what the answer might be. Often times, since we know we’re just going to get a “Good” or “OK” in response.

If you want to have some fun, I highly recommend the next time someone asks you that, say “Terrible”. And watch the computer chip in their brain malfunction for a quick second.

What did I learn?

I won’t claim I found the universal truth or a holistic answer to any of those questions I posed above. Because I haven’t. After all, someone I really respect once told me:

“50% of what you know is true. 50% is false. The problem is you don’t know which half is which.”

So, in my life, my goals are two-fold:

  1. Build a system to help me discern my two halves of knowledge.
  2. Expand the total capacity of what I know.

I will share more on this blog as I am able to draw more lines of regression myself.

But in the context of this post, through social experiments, I’ve discovered that people yearn for psychological safety. Not only does Google’s Project Aristotle share its effectiveness in the workplace, it’s equally, if not more true, outside of it as well. The reason that it’s sometimes easier to share your thoughts and struggles with strangers is that strangers often won’t judge you to the same extent as friends and family do. Frankly, they don’t have much context to judge you from – implicitly and explicitly.

People want fairness. Not in the sense of you get 1 cookie, so I should get 1 too. But a fair system to be judged by. That I will get the same benefit of doubt as you will give to anyone and everyone else. When we all get drunk together, we will all be drunk and we will all relieve ourselves of any filters we may previously have. And though everyone’s drunk personality is different, and frankly everyone will still be judged… For that moment, that night, everyone’s on the same playing field.

The Applications

Let’s take most recent experiment with improv presentations as an example. The initial idea was that everyone should present their own slide decks. As serious or as silly as they might be. But some of my friends were hesitant. In their words, they felt they needed to “impress” or “have better public speaking skills”. Some simply said that they didn’t think they’d “be as good as others”.

Before our first “TED Talks@Home”, I shifted it altogether where we’d all be presenting each other’s presentation. All of us would have no context as to what we’re presenting until we get on “stage”. Whether we were experts on a specific topic or in comedy or deck-making, we’re all jumping into a bottomless pool together. After our second virtual improv night, this past weekend, between muted giggles and visual laughs, one of the presenters told me that it wasn’t as bad as she thought it would be, and that she’d want to do it again.

Luckily, it seems more than 60% of my friends, colleagues, and acquaintances come back to participate in more brunches or game sessions or improv nights. 1 in 4 guests have proactively started friendships outside of the experiments. And about 5% have introduced their new friends to their friend circles. A small handful have also been inspired to start their own. So, maybe I’m doing something right.

Building Communities

The same (psychological safety and fair system) holds true for building communities, creating your corporate culture, and finding and keeping your friend group and your significant other. Although in the context of building communities, but applicable elsewhere as well, I forget who told me this once:

“A strong community has both value and values.”

– The person who told me this, please come claim this quote

Value is why people initially come out to join a community and admittedly, reach out to be a friend. Whether it’s because of who you know or what you can offer or how you can help them pass the time, it’s the truth. Values are why they stay. And safety happens to be one of those values.

In closing

As always, my findings aren’t meant to be prescriptive. But merely act as a guide – another tool in your toolkit – so that you are better equipped for future endeavors.

Like with people, when one day I get to touch a jellyfish, I don’t care about being stung. But I do want to know where I can touch where I won’t be stung. And subsequently, where I will touch where I know I will be stung. The difference between going in blind and not is that when I get stung, I am prepared to be.

Photo by Mathilda Khoo 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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Two Ways Investors Measure Founder Coachability

As much as investors love founders with passion (or obsession) and grit, they also want to invest in founders who have the capacity to grow as individuals as much as their startup grows. And that boils down to how curious and open-minded they are. In other words, how coachable are they? In the past 2 weeks, I’ve had the fortuity to talk to 2 brilliant angel investors – each with their own respective formula for measuring founder coachability.

Formula #1: Assessing Peer Coachability

Last year, I shared a post about the importance of all three levels of mentorship – peer, tactical, and veteran. With the most underappreciated one being peer mentorship. For the sake of this post, let’s call the first angel, Marie. Similarly, Marie finds that peer coachability acts as a useful proxy for founder coachability. And she approaches peer coachability in a very unique way:

What do you and you co-founder(s) fundamentally disagree on?

Following that question, usually 1 of 3 scenarios ensue:

  1. The co-founders can state what they disagree on. And by follow-up question, share how they resolved that disagreement, then how that applies to their framework for resolving future disagreements.
  2. They figure it out on the spot. Better sooner than later.
  3. They say, “Nothing.” And quite possibly, the worst answer they could provide. ‘Cause that means they just don’t understand each other well enough. It’s highly unlikely that given how complex human beings are, that there can be two ambitious individuals who have the exact same outlook on life. Even twins have variations in their perspectives.

Knowing what co-founders disagree on assesses not only how well founders know each other, but also, how they’ve learned from each point of friction. Whether intentionally or not, they become each other’s coaches and push each other forward.

Formula #2: Assessing VC-Founder Coachability

Jerry, on the other hand, tests the waters by offering a controversial opinion about building a business or an insight into the industry, but one he has conviction and experience in. Then, he waits to see how the founder responds. The founder(s) can either:

  1. Disagree, and subsequently walk through where the dissent starts and offer a sequence of data and analyses as to why he/she believes in such a way.
  2. Agree, but still offer how he/she reached the same conclusion.

In either case, Jerry is looking for how mentally acute a founder is and how much room for discussion there is between them. On the other hand, the strike-outs regress to 2 categories:

  1. Disagree, and spend time trying to convince Jerry why he is wrong, rather than working to persuade Jerry to possibly see a bigger picture he might not have considered before. And sometimes, this bigger scope includes a marriage of Jerry and the founder(s) insights.
  2. Agree or disagree, but unfortunately, is unable to substantially back up their claim. Becoming a yes-man/woman in the former, or an argumentative troll in the latter.

The Mentorship Parallel

Unsurprisingly, just like how VCs use these methods to assess founder coachability, I’ve seen mentors use similar methods to assess potential mentees. Many aspiring mentees seek mentorship for its namesake – that metaphoric badge of honor. Not too far from the apple tree when people start a business or come to Silicon Valley to be called a CEO or for their company to be ‘venture-backed’. A category of folks we designate as “wantrapreneurs”.

And unfortunately, many aspiring mentees find bragging rights to be the mentee of [insert accomplished individual’s name]. Yet they don’t actually mean to learn anything meaningful, much less accept constructive criticism. Realistically, no mentor wants to go through that mess. “If you want for my advice, you better take it seriously,” as my first mentor once told me.

In closing

A great VC’s goal is to be the best dollar on your cap table, but they can’t be that Washington if you don’t let them be one. And though it doesn’t call for your investors or board members to micromanage, it does mean you are expected to be candid in both receiving and using (or not using) feedback.

Photo by Xuan Nguyen on Unsplash

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How Marriage Counseling Advice Applies to Managing Team Dynamics

marriage, relationship dynamics, team dynamics

Last Friday, I jumped on a call with my wickedly-creative founder friend. Given his cognitive flexibility, our conversations usually span a multitude of topics. And our Friday call was no exception – from product design to community management to de-stressors. Then, finally, marriage counseling and its applications in managing team dynamics.

Empirically, I focused my attention on co-founder dynamics when sharing an exercise I learned in my expedition to find the curiously passionate and the passionately curious. But I realize now that there are so many direct parallels on a broader scale to teams at large. From none other than a marriage counselor.

I want to preface that this exercise isn’t designed to be universal. And there’s a good chance it may not be useful for the situation you’re in or have been in. But nevertheless, hopefully, it can be another tool in your toolkit. So, if ever, when you do feel the need, it’s something that you can pull from your arsenal.

The Exercise

  1. Start every day gauging your individual gross energy level (i.e. motivation, excitement, emotional state) on a percentage scale with your partner(s)*.
    • * Yes, this was shared to me from a perspective that was inclusive of various forms of romantic relationships, including polyamory. Though I find it to be equally useful, when used among multiple co-founders/team members.
    • To put it into perspective, I usually sit around a 60-70%. When I’m inspired, motivated, or feel I can take on the world, I’m at 90-110%. Although extremely rare, when I’m down (i.e. sick, depressed, sad, unmotivated, stressed, in emotional turmoil, burnt out, or when I just want to regress to my shell), I’m usually at a 10-20%.
  2. Assess if you and your partner(s)’ collective energy level add up to 100% or more.
    • If one of you is feeling down, can (the rest of) you make up for that energy deficiency?
    • If I’m feeling 10%, and I just find it hard to get shit done, can my partner make up that 90% and help us as a team champion the day?
    • And let the person hovering 10% take the day off.
  3. If the collective energy just isn’t there, then the team falls on 2 types of contingency plans.
    1. Can you design a system (or if you already have a system in place) where all of you don’t have to put in 100%, but can still get things done?
      • Maybe this is the day to clean your house. Or wash the car.
      • For founding teams, maybe this is the day the whole team just does data entry.
      • For content creators, I hear this is the day to go through fan mail.
    2. Take the day off. Yes, the full day. And, no halfies. As great philosopher, Ron Swanson, once said:

“Never half-ass two things; whole ass one thing.”

  • Go take a day trip into the wilderness. Play video games. Read a fiction book. Draw. People-watch in a cafe (well, after the quarantine). Netflix-binge. Go tackle something on your bucket list.
  • And cap the downside – the potentiality of a slippery slope. I usually cap it at 3 days. Any longer, the counselor recommended seeing a relationship specialist.
    • Relationship counselor, if romantic.
    • Therapist/psychologist, if emotional.
    • Executive coach, if pertinent to co-founders.
    • Organizational therapist/psychologist, if pertinent to team.

What I didn’t realize until the Call

It seems obvious in retrospect, but it didn’t click until my buddy and I were thinking aloud. Subsequently, we realized how pertinent that exercise can be in understanding team workflows, as well as knowing when to double down and when to backpedal. Productivity has taken a sharp decline in this pandemic. For many, they’ve felt busier and working longer than before. The lack of diverse human interactions – for both extroverts and introverts – is really taking a toll. After all, we’re a social species. For managers, co-workers, and lateral teams, this exercise can be a way you can proactively assess your team’s morale and mental health. Assess early and optimize flexibly.

Photo by Sandy Millar on Unsplash

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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.

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