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Part-time vs. Full-time Founders

Over the weekend, my friend and I were chatting about the next steps in her career. After spending quite some time ironing out a startup idea she wants to pursue, she was at a crossroads. Should she leave her 9-to-5 and pursue this idea full-time, or should she continue to test out her idea and keep her full-time job?

Due to my involvement with the 1517 Fund and since some of my good friends happen to be college dropouts, I spend quite a bit of time with folks who have or are thinking about pursuing their startup business after dropping out. This is no less true with 9-to-5ers. And some who are still the sole breadwinner of their family. Don’t get me wrong. I love the attention, social passion, literature and discourse around entrepreneurship. But I think many people are jumping the gun.

Ten years back, admittedly off of the 2008 crisis, the conversations were entirely different. When I ask my younger cousins or my friends’ younger siblings, “what do you want to be when you grow up?” They say things like “run my own business”, “be a YouTuber”, and most surprisingly, “be a freelancer”. From 12-yr olds, it’s impressive that freelancing is already part of their vocabulary. It’s an astounding heuristic for how far the gig economy has come.

Moreover, media has also built this narrative championing the college dropout. Steve Jobs and Apple. Bill Gates and Microsoft. And, Mark Zuckerberg and Facebook. There’s nothing wrong in leaving your former occupation or education to start something new. But not before you have a solid proof of concept, or at least external validation beyond your friends, family and co-workers. After all, Mark Zuckerberg left Harvard not to start Facebook, but because Facebook was already taking off.

Honing the Idea

The inherent nature of entrepreneurship is risk. As an entrepreneur (and as an investor), the goal should always be to de-risk your venture – to make calculated bets. To cap your downside.

Marc Benioff started his idea of a platform-as-a-service in March 1999. Before Marc Benioff took his idea of SaaS full-time, he spent time at Oracle with his mentor, Larry Ellison, honing this thesis and business idea. When he was finally ready 4 months later, he left on good terms. Those terms were put to the test, when in Salesforce’s early days, VCs were shy to put in their dollar on the cap table. But, his relationship he had built with Larry ended up giving him the runway he needed to build his team and product.

Something that’s, unfortunately, rarely talked about in Silicon Valley and the world of startups is patience. We’ve gotten used to hearing “move fast and break things”. Many founders are taught to give themselves a 10-20% margin of error. What started off as a valuable heuristic grew into an increase in quantity of experiments, but decrease in quality of experiments. Founders were throwing a barrage of punches, where many carried no weight behind them. No time spent contemplating why the punch didn’t hit its mark. And subsequently, founders building on the frontlines of revolution fight to be the first to market, but not first to product-market fit. Founders fight hell or high water to launch their MVP, but not an MLP, as Jiaona Zhang of WeWork puts it.

In the words of the one who pioneered the idea of platform-as-a-service,

The more transformative your idea is, the more patience you’ll need to make it happen.”

– Marc Benioff

As one who sits on the other side of the table, our job is to help founders ask more precise questions – and often, the tough questions. We act more as godmothers and godfathers of you and your babies, but we can’t do the job for you.

The “Tough” Questions

To early founders, aspiring founders, and my friends at the crossroads, here is my playbook:

  • What partnerships can/will make it easier for you to go-to-market? To product-market fit? To scalability?
  • What questions can you ask to better test product feasibility?
  • How can you partner with people to ask (and test) better questions?
  • What is your calculus that’ll help you systematically test your assumptions?
  • Do you have enough cash flow to sustain you (and your dependents) for the next 2 years to test these assumptions?

Simultaneously, it’s also to important to consider the flip side:

  • What partnerships (or lack thereof) make your bets more risky?
  • How can you limit them? Eliminate them?

And in sum, these questions will help you map out:

At this point in your career, does part-time or full-time help you better optimize yourself for reaching my next milestone?

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What Does Personal Progress Look Like?

In the past two weeks, through conversations on my birthday resolution and what my success metrics are, my friends inspired me to write this post . That’s when you know I’m in Silicon Valley! Or startup Disneyland.

So, how do I measure my progress? This is by no means proprietary or original. In an annual email exchange, my mentor had me ask myself one question:

How ashamed do I feel about myself one year prior?

Although not comprehensive, I find it to be a great litmus test for evaluating personal development. If I don’t scoff at my former self for being dumb, I’ll know I haven’t progressed. At the same time, I put myself in the shoes of my future self, abstracting myself from my status quo, and ask two questions:

  1. What aspects of my past self am I embarrassed to see?
  2. What strengths of my past self would I find extremely unimpressive to show off?

This acts as an ego check and helps me look at myself more objectively.

I started this practice two years ago where I keep a checklist (on Google Keep) of wins I keep track of throughout the year. It included any magnitude of achievement, like:

  • A successful deal close;
  • Joining as a guest on a podcast;
  • An art piece I’m proud of drawing;
  • Cooking a meal that pleased my parents;
  • And, sleeping 8 hours a night.

Then one week prior to my birthday, Google Calendar reminds me to go through that checklist and review what I still feel proud of and what I find to be ‘normal’. I check all the ones I no longer gain contentment from. All that’s left are “My Proudest Moments at Age XX”. Then my goal for the following year is to make those moments feel ‘normal’. I’ll get to this step eventually. But I plan to review the annual lists every 5 years to see if I still feel the same.

In a way, this blog is also designed for me to reflect on earlier iterations of myself through my writing. As much as this one question has enlightened me, I hope it may act as your heuristic for your growth.

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v24.0

Photo by Ian Schneider on Unsplash

My parents have always conditioned me to plan each of my ages out. When I was younger, every year I ranked up they would ask me what I want to get done. At the same time, I never felt a strong commitment to New Year’s resolutions. Maybe it was ’cause of the gingerbread cookies. Or the Christmas presents. Or the fireworks and the ball drop. But that lull between the holidays wasn’t conducive to me setting meaningful goals. The “promises” I made carried no weight behind them.

Three years back, after reading Brad Feld’s birthday resolution, I decided to start setting my own birthday resolutions. Outside of a mere date shift, there were 3 reasons I chose to do so:

  1. I had time to recover from the holidays – to get my head straight.
  2. I was motivated watching my friends, family, and coworkers tackle their New Year’s resolutions in the month prior. (Admittedly, more often than not, they lose their initial trajectory, but I only saw the beginning of many of their inverse parabolas.) Motivation is one side of the coin; FOMO is another.
  3. In that motivating January, assuming I haven’t yet completed my previous year’s resolution(s), it motivates me to finish strong – the “last mile” sprint.

That said, this is my first year posting my resolutions publicly. Why? One, it’s to keep me accountable. Two, as Jeff Wald once said, “practice true vulnerability by opening up about the potholes ahead, not just the ones in the rearview mirror.” And one of my resolutions from v23.0 was to become more comfortable being vulnerable. So, what will the new update look like?

Here are the patch notes:

Build ideas from 0 to 1.

This year, I plan to actively help 2 startups go from idea to product-market fit. After 3 years on the venture side of the cap table, the one thing I’ve noticed more and more is that I miss getting my hands dirty, especially in the early stages. I miss the ups and downs. I miss the freaky moments (and the big wins). It may sound a bit weird. But I may have emotionally removed myself from being entrepreneurial and trapped myself in a bird’s-eye perspective only. And I hate it.

More artistically creative outputs.

Two years ago, I started idea-journaling by inspiration from my former college professor. After going through 9.5 idea journals, I realized I’ve spent less than 10% of my ideation space on artistic pursuits. 40% on VC and startups. 40% on personal projects and experiments. 10% everything else. There’s clearly a lack of diversity in my creative space. So, this year, I’m committing to producing one new art piece every week – be it a new drawing, music composition, culinary permutation, or something that’ll surprise myself. My deepest gratitude to my friends who gave me new canvases to explore my creative white space. You can track my progress on my Instagram.

Balancing Social Media.

In the year when many of my peers are unplugging, I’m going to be more active on social media, fine print included. I’m going to explore more by contributing content on this blog, my Instagram (for artistic pursuits), LinkedIn, Medium, Quora, Reddit, and Discord.

I’ve always shied away from social media – not because of some grandiose sense of self-discipline, but rather since I’ve never been able to fully conquer my shell of introversion. After all, my Facebook profile picture and lack of presence is my form of psychological armor.

That said, I still won’t be scrolling through my news feed on social media. But I will aim to respond to every comment and DM that comes my way. I’m a firm believer in responding to the commitment and time people take to write a thoughtful message. Luckily, I’m also at a stage in my life and career when I don’t have more messages/emails than I can manage.

Reconnecting.

Over the past half decade, I’ve grown a lot from reaching out to, learning from, and helping new folks in my network. And, I’m grateful for each and every experience. I wouldn’t be here today if it weren’t for them. But as a result of constant pursuits of new experiences and expanding my network, I haven’t been able to reconnect with friends, mentors, teachers, and acquaintances I’ve had in the past, outside of my annual holiday greetings and thanks. In this new update, I’m committing 10 minutes every day to meaningfully rekindle old flames that I haven’t caught up with in the past 6 months.

Read more.

By virtue of reconnecting with friends from my past, it’s useful to have content and inspiration when reconnecting, but also as a means to widen my own knowledge horizon. Outside of work and my one-book-a-month of reading, I’ll be indulging in a minimum of an hour of diverse reading every day via the ‘Discover’ tab on Pocket.

Sleep and wake earlier.

Ever since college, I’ve been a night owl. It’s weird ’cause in college, students apparently have this ego contest of how many ‘all-nighters’ one can pull and still be ‘alive’. Being young and naive, I joined in the chorus, but I never won. In fact, in my entire college career, I pulled only 2 all-nighters, not even back-to-back, and I was already dead. But it ended up ruining my sleep schedule. I would go to sleep between 12 and 3AM. Sometimes for no reason at all.

After I came back from my holiday Europe trip, mostly due to jet lag, I started sleeping at 9PM every night for the first week. I felt so much more refreshed in the morning and through most of the day than when I didn’t. But also, there’s so much less noise in the morning between 4:30 and 6:30AM – both on social media and in the neighborhood. And I could much of my creative work done. This year, I’m going to sleep at 10PM latest and wake at 4:30AM.

Goal-oriented exercise.

I haven’t necessarily been unfit, but my daily routines seem to drone by without any personal achievement or goal in mind. I have no plans to reach my past physical prowess where I spent 30-40 hours a week spent on exercise. But this year, I’ll stick to 2 goals for health and exercise: sub-5:30 mile and 20 pull-ups. (I’m at a 7:15 and 7 pull-ups at the time of writing this post.)

–

It’s going to be an exciting year, and I plan to have plenty of hotfixes before I reach v25.0, hopefully daily. Thank you to my friends for all the birthday wishes, support, and feedback.

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An Innovator’s Inspiration

Photo by Skye Studios on Unsplash

Creativity.

I have a love-hate relationship with that word. On one hand, I love and seek to learn from creative souls. It’s a trait that I seriously respect in individuals, regardless of industry, profession, or background. On the other hand, it’s rather amorphous. What’s creative to me may not be creative to you. We are bounded by the parameters of our experiences and what we, as individuals, are exposed to.

So, where do innovators draw inspiration?

Over the years, I’ve seen inspiration stem from three main frameworks:

  • The flow from art;
  • Margins;
  • And, what people dislike.

The Flow from Art

I seem to find that the data largely (with a few outliers) points towards the following:

Art precedes science. Science precedes tech. Tech precedes business. Business precedes law.

Art is bounded only by one’s imagination. Science, which draws inspiration from art, is limited by our physical universe and the fundamental laws. And, tech rides on the coattails of science, restricted by the patterns recognized in our universe by scientists before them. Similarly, business can only optimize existing technology. Following suit, regulations and legal practice can only debate and prevent ramifications that have turned from hypothesis to reality.

On one end of the spectrum, fiction has driven innovation on the fundamental, scientific front. Scientists have tried to make the impossible – fiction, superstition, assumptions, and imagination – possible. On the other end, the legal and regulatory space has empirically lagged behind business innovation. From autonomous driving to the shared economy to video games, a regulatory emphasis came only after incidents occurred. I’m a huge proponent of founders becoming self-regulatory. But that is a discussion for another day.

Margins

As Jeff Bezos famously said:

“Your margin is my opportunity.”

In the lens of a businessperson, profits exist on the margins. In a fully saturated market, as we learned in economics class, perfect competition will squeeze out profits. That margin can be delta between human perfection and imperfection. It can be the difference between a naive and sophisticated individual. It can also be the blind spots between a self-awareness and ignorance.

The good news (and bad news?) is that humans aren’t rational. As much as we try to be, we’re not. We repeat the same mistakes. After all, that’s where our favorite stories come from – the fact that we’re imperfect. If we were rational, our friendly neighborhood kid from Queens wouldn’t have to struggle with identity. Or, Skinner, the head chef at Auguste Gusteau’s restaurant, wouldn’t be out to exterminate my favorite rat chef.

From a nonfictional front, if we were rational, gambling, the lottery, therapy, and more wouldn’t exist. In fact, there’s a whole industry that capitalizes on human imperfection – insurance. We choose to reach for that last cookie when we know a healthier diet with less sugar is better for us (I’m guilty as well). We set New Year’s resolutions to work out more, but regress to our couch norm after the first month. Walter Mischel famously conducted The Marshmallow Experiment. When given the option to wait 15 minutes to double their treats, many children opted for immediate gratification.

There would be way fewer founders if they were rational. I mean, come on, the numbers work against them. 90% of startups fail. So, from a VC’s perspective, we have to ask ourselves:

What’s is the underlying notion that makes this product work?

What is that innate theme in human or societal development that won’t disappear anytime soon? What factors produce such a trend? And what margin is it taking advantage of? Uber was made possible with the evolution of smartphone and faster data. As more data were archived online, Google became a reality because of the internet and browser. Two current examples of underlying notions include:

  • Audio, including, but not limited to, podcasts and audiobooks, is the new form of content consumption. Not only does it free up consumers’ hands and eyes up, audio content is often easier to digest. The spoken word has been around millennia, whereas print is fairly new invention. Emotions and sarcasm is often easier to relay via audio than via print. So, what else is possible?
  • With growing consumer sentiment against traditional social media, like Facebook, Twitter, and Instagram, there is a shift to social experiences surrounding active participation. Sarah Tavel writes a great piece on this. Examples include Discord, Medium, TikTok, and user-generated content (UGC) in video games, like mods and in-game skins. Many of the traditional social media platforms leave users with a more negative passive experience, where they feel a sense of FOMO (fear of missing out). Through active participation, users can be a part of the conversation, rather than watch from the sidelines.

What do you dislike?

Speaking of negative experiences, aversion is a strong motivating emotion humans have. Like prospect theory illustrates, loss invokes a stronger response than gains. It also happens to be one of the reasons why I probe how obsessed a founder is about a certain problem.

In a recent interview with Andrew “Kappy” Kaplan, host of the podcast, Beyond the Plate, Grant Achatz, legendary chef, talks briefly about how he drew inspiration from his daughter’s dislike of cheese, yet she still ate pizza and grilled cheese sandwiches. Similarly, when his guests at Alinea didn’t like sea urchin, he thought about the ‘why’ and if he could circumvent their aversion by playing with various variables, including iodine concentration.

So, what do you dislike (with a passion)? What about the people around you? And can you figure out a way to change or eliminate that frustration? Take some time through the idea maze.

In closing

Ideas come in all shapes and sizes. Some may be more obvious than others. Some may snowball into a best-selling one. Although I’ve shared the three most common frameworks that I’ve personally generated and seen others find inspiration, it is, of course, not the only ways to exercise your creative muscle. In fact, the first step into being more “creative” is being cognizant about everything around you.

Two years ago, one of my former professors recommended I start ‘idea-journaling’ every day. Since I’ve started, I began noticing more and more stimuli from my surroundings, conversations and frustrations.

It may be a start, but it’s by no means an end. Stay curious.

Photo Credit: Ariel Zhang @yuzhu.zhang
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The Different Types of Risk a VC Evaluates

Photo by trail on Unsplash

Founders take on many different types of risk when creating a business. Subsequently, investors constantly put founders and their businesses under scrutiny using risk as a benchmark. In broad terms, in my experience, they largely fall under two categories: execution risk and market risk.

Finding Product-Market Fit and “Idea-Market Fit”
Where I first introduced the dichotomy of market and execution risk in the frame of idea-market fit.

Some Background

Contrary to popular belief, VCs are some of the most risk-averse people that I know. As an investor, the two goals are to:

  1. Take calculated bets, via an investment thesis and diligence;
  2. And de-risk each investment as much as possible.

From private equity to growth equity to venture capital, more and more investors are writing ‘discovery checks.’ Typically, funds write checks that are 2-4% of their fund size. For example, $100M fund usually write $2-4M initial checks. Yet, more and more investors are writing increasingly smaller check sizes (0.1-0.5% fund size). In the $100M fund example, that’s $100-500K checks. This result is a function of FOMO (fear of missing out), as well as a proving grounds for founders before the fund’s partners put in their core dollar. Admittedly, this upstream effect does lead to:

  • Less diligence before checks are written (closing within 48-72 hours on the extreme end, and inevitably, more buyer’s remorse);
  • Less bandwidth allotted per portfolio startup (even less for startups given discovery checks);
  • And, inflated rounds (and therefore, inflated startup valuations).

The Risks

The risks for a startup investor are fairly obvious, and so are the rewards. Effectively, an early-stage investor is betting millions of dollars on a stranger’s claim. But not all risks are the same.

In the eyes of a VC, an execution risk is categorically less risky than a market risk. Furthermore, even within the category of execution, a product risk is usually less risky than a team risk.

Execution Risk

Why are more and more early-stage investors defaulting to enterprise over consumer startups?

Two reasons.

  1. Enterprise startups often run on a SaaS (software-as-service) subscription business model. There will always be recurring revenue, assuming the product makes sense. For an investor, that’s foreseeable ROI.
  2. It’s an execution risk, not a market risk. Often times, an enterprise tech startup is the culmination of existing frustrations prevalent in the respective industry already. And therefore, have reasonably stable distribution channels and go-to-market strategies.

Eric Feng, formerly at Kleiner Perkins, now at Facebook, used Y Combinator’s data set at the end of last year to illustrate the consumer-to-enterprise shift.

Using discovery checks, and playing pre-core business, VCs can evaluate team risk. Between the discovery check and their usual ‘core checks’, VCs can also test their initial hypotheses on their founders.

As a startup grows, especially after realizing product-market fit, market risk becomes more of a product risk. Best illustrated by market share, product risk is when a product fails to meet the expectations of their (target) customers. It can be evaluated via a permutation of key metrics, like unit economics, NPS, retention and churn rate. There is an element of technological risk early on in the startup lifecycle for deep tech ventures, but admittedly, it’s not a vertical I have my finger on the pulse for and can share insight into.

Given that VCs are either ex-operators or have seen a breadth of startup life-cycles, VCs can best use their experience to mitigate a startup’s execution risk.

Market Risk

Market risk requires a prediction of human/market behavior. And unfortunately, the vast majority of investors can predict about the constant evolution of human behavior as well as a founder can. What does that mean? Founders and VCs are walking hand-in-hand to gain market experience. It, quite excitingly, is an innovator’s Rubrik’s cube to solve.

Market risk is frequently attributed to consumer tech products. In an increasing proliferation of consumer startups, consumers have become more expensive to acquire and harder to retain. Distribution channels change frequently and are determined by political, economic, technological, and social trends.

In Closing

Every VC specializes in tackling a certain kind of risk. But founders must quickly adapt, prioritize, and tackle all the above risks at some point in the founding journey. As Reid Hoffman, co-founder of LinkedIn, famously said:

“An entrepreneur is someone who will jump off a cliff and assemble an airplane on the way down.”

Happy hunting!

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Being Nice vs. Running a Great Business

Photo by Matteo Vistocco on Unsplash

While on my way to see a friend the other day, instead of cancelling, our Uber Pool driver decided to wait for the third rider. After a few exchanges of texts and calls, to the vocally evident dismay of the rider before me, we ended up waiting eight minutes. Therefore, delaying the rest of our arrival times by that same margin. In the ensuing silence that followed, I spent a little time thinking about the fascinating dichotomy between being nice and running a great business.

At the risk of receiving two low-star ratings, our driver opted to be nice and wait for the potential one five-star rating. To his credit, the third rider was incredibly grateful for his patience. In an alternate universe, he would have chosen to cancel the last rider’s request after waiting about two minutes.

The Examples

Social stereotypes might suggest that being nice and running a great business are two polar opposites. The portrayals of Mark Zuckerberg, in The Social Network, and Steve Jobs, in every biographical movie of him, only further perpetuate this motif. But, the truth is they’re not mutually exclusive. Many of the best businesses out there, like TOMS and Salesforce, are purpose-driven and spread positive impact. In the past few years, it should and has been, for many, a priority for building a brand.

Driving positive social impact is beginning to gain traction among a class of notoriously financially-driven individuals: venture investors. Although impact investing is one way, prominent VCs, like Felicis Ventures and Brad Feld, have also committed to founder’s mental health.

The marriage of being nice and running a great business comes in two parts:

  • Transparent and honest communication with your customers,
  • And, follow-through on promises and feedback implementation.

After all, it’s a collaborative effort.

One of my favorite examples is Digital Extremes – the developer for one of the most popular games on Steam, Warframe. Like many other businesses, they donate regularly to charities – from leukemia awareness to children’s health to most recently, the Australian wildfire. But, unlike many others, they engage their users every week through their stellar community management team. In fact, their community director, Rebecca Ford, was recognized in the 30 Under 30 Forbes list this year. Through a weekly permutation of developer streams, forum posts/polls, and social media content, they listen and engage with feedback. And through weekly hotfixes and content updates, which already speaks volumes in the game industry, they incorporate that feedback.

Don’t just take my word for it. Their subreddit serves as an example of one of the most positive and honest communities I’ve ever seen.

In Closing

Of course, no business is perfect. And the business may not always agree with the consumer’s thoughts. But, through transparent communication, radically candor (thank you to the brilliant Kim Scott), and following through, you can be nice and run a great business.

Instead of staying silent, if our Uber driver had asked us if we were in a hurry and agreed on a time limit to how long we’d wait (maybe even offered us a snack during the wait, but that might be stretching it), he might have gotten three five-star reviews.

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Setting Culture

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I just started my second read of Ben Horowitz‘s new book, What You Do is Who You Are: How to Create your Business Culture. It’s a brilliant deep dive on what culture and virtues mean for a growing company or team. From the most successful slave revolution in history to prison culture to the samurai bushido, Ben draws parallels between those and startup culture, where you can get a snapshot here.

On page 31, Ben wrote “Create Shocking Rules.” Why “shocking”? So people will ask why. So people will pause, think, and remember them. What is “shocking”? In a time when raping and pillaging was the norm, Toussaint Louverture, the man who led the Haitian Revolution, forbade officers from having concubines. And he kept to that promise. When “shocking” isn’t the only game changer, you need uncompromising commitment to those rules. Weak follow-through is another fallacy in creating the culture you want. What you let slide will define the new culture, with or without your approval.

Sun Tzu and the Concubines

Rereading about Toussaint Louverture reminded me of a story my dad used to tell me by my bedside. About another brilliant general, who lived 2000 years prior to Toussaint during the Spring and Autumn Period, and best known for authoring The Art of War, Sun Tzu.

Through his thirteen chapters, dubbed The Art of War, he eventually earned an audience with the king of the State of Wu. Hoping to test Sun Tzu’s strategies to its extremes, possibly expecting to see Sun fail, the king asked Sun to test it on his harem of concubines.

After accepting the task at hand and separating the concubines into two companies, Sun had them all take a spear in hand and said, “I presume you know the difference between front and back, right hand and left hand?”

The women answered, “Yes.”

After explicitly explaining what “Eyes front”, “Left turn”, “Right turn”, and “About turn” meant, he issued his first order at the sound of the drums, “Right turn.” But, the concubines responded with fits of laughter. Sun Tzu proclaimed, “If words of command are not clear and distinct, if orders are not thoroughly understood, then the general is to blame.”

In another attempt, he called out, “Left turn.” His words met the same fate as the ones he uttered just prior – with laughter. This time, he said, “If words of command are not clear and distinct, if orders are not thoroughly understood, the general is to blame. But if his orders are clear, and the soldiers still disobey, then it is the fault of their officers.”

Subsequently, he ordered the heads of the two companies beheaded, whom happened to be king’s favorite two concubines. Seeing what had unfolded from his pavilion, the king sent a messenger to plead with Sun to keep his two favorite alive. But Sun did not relent.

After their execution, he immediately installed two new officers, and from then on, the concubines followed every order that Sun issued to the T.

Using the principles he shared and taught in The Art of War, Sun Tzu won many battles for the State of Wu, most notably, when Sun Tzu led an army of 30,000 to defeat an enemy numbering ten times more than the troops from Wu. As Jon Stewart, former The Daily Show host, once said:

“If you don’t stick to your values when they’re being tested, they’re not values: they’re hobbies.”

In Closing

In his book, Ben shares quite a bit how some of the best leaders in the world shaped their organizational culture. It wasn’t from catered lunches or having dogs in the office every Friday. Culture comes down to setting “shocking” rules, paired with a set of priorities, and more importantly, keeping them. Culture is what your team members remember about your organization and how it made and makes them feel 20 years down the road.

Though not perfect, my former swim coach instilled the same virtues in us. He was never a fan of tardiness. To him, it demonstrated a lack of character and commitment. And to enforce that, if we were late, by even a minute, to get into the water (not arrive at the pool), the offenders had to swim the entire warm-up in butterfly – the whole 2000 yards. And not one person escaped that law, not even him – not that I ever saw him late.

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A Reason to Stay

Photo by Hayden Scott on Unsplash

In the first startup I joined, we messed up our initial business model by not providing a reason for small- and medium-sized business (SMB) owners to stay. We created a marketplace between SMBs to transact with each other. But, after the first one to three transactions, they had no need for our platform. The scary thing about marketplaces isn’t that you’re connecting suppliers to their demand network, but not providing any bonuses after onboarding – a reason to stay.

Some of the stickiest companies are marketplaces because they provide that reason to stay. More often than not, providing a lovable product so convenient, it’s much easier to use the marketplace platform than to do the transaction themselves, and an easy, passive way to be discovered by future clients/customers that would be much more difficult on their own.

Why Multiplayer Video Games Work

In his book The Messy Middle, Scott Belsky, Chief Product Officer at Adobe and founder of Behance (acq. by Adobe), a discovery platform where creatives can showcase their portfolios and engage with others’, shares that when crafting the ‘first mile’ experience, you need to optimize for three questions:

  1. Why are your customers here?
  2. What can they accomplish?
  3. What can they do next?

Arguably, I believe that founders should always have these three questions hovering above their product strategies, beyond the ‘first mile’, only embedded more implicitly. Video games do an amazing job in this regard, especially massively multiplayer online role-playing games, or MMORPGs for short.

Why play the game? Find escape and sanctuary to be someone players want to be but can’t in the confines of reality.

What can they accomplish? Achieve that endgame that players see in the trailers and in the tutorial (the onboarding for an MMORPG user). The endgame is self-defined as well. Of course, the game optimizes for the power creep meta endgame. Yet, players can always opt for a ‘destiny’, a story, they find compelling, like becoming a fashionista, a wealthy merchant, a mentor, a content creator, and with faster computing systems and more robust infrastructure, a contributor to the game itself, through user-generated content (UGC). The Steam Workshop is an excellent example of UGC.

What can they do next? Level up their character and gear. Tackle the next quest – main or side – towards something larger than themselves. There’s always a defined goal, as well as actionable steps and additional incentives laid out for the players. This creates high retention value – a reason to stay.

The same is true for many other types of genres of multiplayer games – multiplayer online battle arenas (MOBA), battle royale (BR), first-person shooters (FPS), and more. It’s just the narrative of the endgame may change a little towards leaderboard domination. E-sports, content creation, and live streaming then offers a new tier of recognition and endgame for many veteran players.

Back to Marketplaces

I’ve always argued that as a founder, you want to focus on unscalable wins before thinking of scale pre-product-market fit. Focus on the individual experiences. As Li Jin, partner at the reputable a16z, wrote in a post about the passion economy, “[great founders] view individuality as a feature, not a bug.” The best marketplaces, like Uber, Airbnb, and Medium, started off focusing on the unscalable wins for a small individual subset of their potential users. These products offered their early users a reason to stay:

  • (Additional) Incentives and tools, to make their stay worthwhile;
  • Discovery platform to help them grow their brand and customer base, actively and passively;
  • And, subsequent community and network effects.

Early adopters jump on a new product, as fast as they jump off one. They’re finicky. They’re window shoppers, but at the same time, the most willing and likely to try out your product. Luckily and unluckily, the San Francisco Bay Area has no shortage of these folks, and being a tech startup, with its initial user base here, often inflates your early metrics. In short, the goal of your product is to make these technological butterflies fall madly in love with you and your product. That’s the tough part, but it’ll also mean you’ve found product-market fit (PMF).

Where do we find ‘love’?

Instead of a minimum viable product, or MVP, Jiaona Zhang, Senior Director of Product at WeWork, in her First Round Review piece, chases the “pixie dust”, or what I like to call the secret sauce – a truly unique, money-making insight. This magic is found through diligent iteration on consumer feedback, especially in the beta stages of a product. During the beta, users have the serendipity to discover “that magical moment in the user journey where the user realizes that this product is different from anything else they’ve ever experienced”. Her framework, designed from the perspective of the consumer:

Wouldn’t it be cool if users could [a process/action that would 10X their lives]?

What We Learned

The same was true for us at Localwise. Of course, we were motivated by poor retention metrics. But, we learned what businesses truly needed by asking each of them in person, as well as flyering (and getting rejected, or worse, ignored) to college students and to shops. So, still deeply in love with the community we built, we found that need when connecting local talent to SMBs. For businesses with high churn rate with temporary employees and a need to build a brand, that was their reason to stay.

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Three Types of Mentors

Photo by Rohan Makhecha on Unsplash

Christmas 2019 has finally turned its page, and Santa has granted with us with either presents or coal. Then again, coal may not be so bad. In /r/ShowerThoughts (where I regrettably spend maybe a wee bit too much time in), a Redditor shared that with a little pressure, naughty kids can turn their coals into diamonds.

Possibly deserving coal myself, every year, between Christmas and the new year, I regress to a husk of myself and binge the eight Harry Potter movies. Inspired by the Triwizard tournament, Cedric Diggory’s valiant sacrifice, and in a beautiful Socratic debate with some of my friends on Harry’s most impactful mentor, an unlikely hero came up – Mad-Eye Moody.

The Three Types of Witches/Wizards

As a nerd about mentorship, I believe mentorship is equal parts art and science. Every mentor-mentee relationship is unique like the stripes of a zebra or the folds in a human fingerprint. Along your life journey,you’ll have the fortune of being with many different mentors and mentees. Some are fleeting; some are life-long. Yet, there are still general themes among these relationships. More specifically, I’ve observed three kinds of mentorships:

  • Peer,
  • Tactical,
  • And, Veteran.

Peer mentorship comes from someone who is facing a similar problem to you or has as much experience in a respective field as you do. A peer mentor will be down in the dirt with you, rolling in the mud. Together, you aim to learn how to navigate the complexity of the landscape.

Tactical mentorship comes from someone who has two to five years more experience than you in a field you want to grow in. He/she is someone who is able to able to see around the corner before you do. A tactical mentor can provide the nitty-gritty tactics to conquer many of your challenges. Most startup investors, who see a breadth of deals, but only experience some depth, tend to fall under this category.

Veteran mentorship comes from someone who has already attained the level of success that you hope to one day achieve in a given field. Veteran mentors can help you define your true north, providing both vision and scope. Unfortunately, because it’s been a few since they’ve tackled a similar scope of a problem, they won’t be able to provide the ABCs for you.

Magic and Mentorship

Like the Triwizard Maze, the world around us is always changing, posing new obstacles and surprising us with new challenges. Though not frequently, the variables and parameters for our success will always be changing. Our peer mentors, like Cedric Diggory, Fleur Delacour, and Viktor Krum, are our companions to conquer the seemingly impossible. Our tactical mentors, like those who have been chosen by the Goblet before, help us to make the right judgment at each crossroads. Our veteran mentors, like Mad-Eye and Dumbledore, are our lumos to see a bigger picture. All of them will help us find the signal in the noise. More importantly, are the supporting force that have, is, and will be pushing us forward towards our own Triwizard Cup.

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Five Lessons from “Brunches with Strangers”

Photo by Jay Wennington on Unsplash

One of the biggest aspects I lost when I graduated from college was the social life. All my social interactions these days range from driving distance to the need to cross the Pacific or Atlantic, compared to a simpler time when my friends were within walking distance. So, earlier this year, I started a little passion project: Brunch with Strangers (BWS).

BWS began as an effort for me to:

  • Help overcome my deep fear of public speaking;
  • Have an excuse to bring fascinating souls to the same table;
  • And, help make the San Francisco Bay Area feel just a little smaller and just a little more human.

It’s a Saturday brunch I hold every fortnight between six to eight thrill-seekers, hustlers, crafts(wo)men, entrepreneurs, engineers, and curiously-curious individuals. They are working on interesting projects, have captivating stories, and/or possess an infectious drive for their passion. The key element is that I have to be reasonably confident that they don’t know more than one other person who will be at BWS before the meal, which is, admittedly, harder than I initially thought for folks in the Bay Area. After 20 brunches, with a little over 100 guests and circling back in with 90% of them in the post-mortem, here are the five main takeaways from these enthralling conversations, ordered from the most to least intuitive for me:

  1. Structured conversations work better than unstructured conversations.
  2. Cap it.
  3. The culinary experience doesn’t matter.
  4. Embrace “awkward” silences.
  5. Don’t introduce the guests before the day of the brunch.

Structured conversations work better than unstructured conversations.

But what does “better” mean? I measure “better” by the guests’ answer, a month after the brunch, to the question:

Were you able to catch up with another BWS guest (whom you did not know beforehand) in person?

In the context of startups, that question is how I measure my product-market fit, which I share more context to in a separate post. Guests of a structured BWS are 30% more likely to catch up in person within a month of the brunch than guests who join me in an unstructured BWS. Between structured and unstructured brunches, a structured brunch is when I have at least one activity or topic planned for during the brunch, whereas unstructured brunch, my “control variable”, happens when the guests get to decide how and where the conversation goes, and discussion is more free-flowing.

Over the score of brunches I’ve hosted, the two most well-received activities were 1) a game I call Hidden Questions, and 2) where each guest brings two asks.

Hidden Questions, inspired by Jimmy Fallon’s Pour It Out, is a game where each person has to answer truthfully two to three questions, written by the previous group of people who played the game, but is not required to reveal what the question is. The deck of questions the previous group writes, which even I’m not privy to look through, can cover any topic and ask any range of questions – from favorite books to deepest fears to NSFW ones. Some of my personal favorite are “When was the last time you uncontrollably cried?” and “When was the last time you said ‘I love you’?”. If the person answering the question does not reveal the question itself, he/she has to eat a Beanboozled bean or take a spoonful of one of the spicier hot sauces found on the show Hot Ones. The catch is before the person answering the question decides to reveal question or not, the other guests can ask clarifying questions and bet additional beans or spoonfuls of hot sauce for the person to eat if he/she doesn’t reveal. So, if he/she does, then the other guests eat what they bet. It’s a fascinating game that creates a safe space where people have the excuse to be vulnerable, as well as revealing each person’s level of risk aversion.

On the flip side, to help guests mentally prepare and pick the dilemma of the highest priority, I ask guests at least 48 hours, up to a week, in advance to bring two asks to the brunch:

  1. One that they’d feel comfortable sharing with most of their friends;
  2. And, one that’s either deeply troubling them and require them to be vulnerable, or one that shows a very different side of them that most people they know might not recognize.

The asks themselves are structured by answering two questions: ‘What are you currently working on?’ and ‘What do you need help with?’, which can range from work to personal life to new projects and hobbies to relationships. When the time comes to share the guests’ asks, usually about 20 minutes in, I ask them to share the one they’re more comfortable in sharing. Based on what they share, I can gauge how comfortable they are with the other guests, as well as indicate how well I’m doing my job.

The asks also incentivize mentorship from folks who have had wildly different experiences in different industries at different ages. For example, an autonomous driving product manager provided advice on building systems to streamline communication to a remote workforce to a newly-minted landlord and property manager by predicting actions and that may need to be taken by the landlord’s employees and working to preempt them. In another brunch, an indie film producer taught us all how to hustle, be scrappy, and run effective crowdfunding campaigns by going back to the roots of meeting people face-to-face rather than over the Interwebs. And more recently, a digital nomad shared his $0.02 on how to build a network and community in a new geography and culture from scratch by being willing to do manual labor and noticing when people needed help, to build trust.

Cap it.

One of the best conversationalists I know, Bobby, once told me:

“A great conversation is like flirting with a girl you really like.”

Share enough to make him/her interested, but close the conversation sooner than you’d like to suggest a sense of scarcity, as well as a reason to go on a second date. If you reveal everything too soon, your audience will most likely lose interest as soon as they have no more questions, like how many of my friends have spoiled the whole plot of Game of Thrones (and now it’s The Mandalorian) before I even began Episode 1 of Season 1.

The same seems to be true for the BWS conversations. I found a moderately strong negative correlation between the length of the meal and the number of in-person catch-ups within a month of the meal, after the first one-and-a-half hours (and a moderately weak negative correlation of meal length and number of in-person catch-ups, if the meal length lasted between an hour and an hour and a half).

Both to be respectful to others’ schedules and to motivate them to catch up after, I cap the brunches to 1.5 hours. To be fair, I am still testing out the optimal length of time, since I don’t have a big enough sample size to decide from.

The culinary experience doesn’t matter.

I initially thought that more interesting meals and/or great eats, which at times, fell on the more expensive side at two to three dollar signs, would give folks, in the worst possible scenario, the culinary experience to talk about when they have no other topic or background of each other. It turns out the culinary experience doesn’t have a strong correlation to the reduction of the number of awkward silences, which I assumed would serve as a leading indicator for how likely guests were to catch up in-person after.

In fact, even when guests had the disposable income to afford the meal, when a meal is expected to exceed $50 per person, it is more likely that the culinary experience detracts from how vulnerable a person can be.

The culinary experience will always come second to the guests and the conversation they bring.

Embrace “awkward” silences.

Speaking of awkward silences, my initial goal was to reduce the number of “awkward” silences in a conversation. Maybe it was my anxiety speaking, but I realized two things:

  • What’s awkward to me may not be awkward to another;
  • And, silences are diamonds yet to form (under pressure).

Some people need time to digest everything they have heard up to that point in the conversation. Some people need a break to eat the food they ordered. Some people need time to formulate the next question they want to ask. But for me, silence offers an opportunity to allow guests to dig deeper.

In relation to silence, fours years ago, one of my dearest mentor figures, Robin, shared two rather insightful tips with me:

  1. “Listening is the most important of conversation, and silence, too is one of the sounds a conversation emits.”
  2. “People like to talk about themselves. Give them the opportunity to.”

Silence is that opportunity for people to share more about their life stories. And with the right prompt, it can become a safe space for them to be more vulnerable. And there are two ways I help them continue, with the addendum that I, myself, am vulnerable with them first, earlier in the brunch:

  1. Lean in. Ideally, with an open inquisitive look. I don’t have to say anything, but it will eventually prompt them to continue. It might feel a bit awkward at first.
  2. Ask them to rewind to a point they brought up that I find fascinating, curious, or needs more explanation.

Late night talk show hosts, like Conan O’Brien and Stephen Colbert, and podcast hosts, like Tim Ferriss and Cal Fussman, are really acute at catching these moments and serve as great case studies.

Don’t introduce the guests before the day of the brunch.

At first glance, this seems a bit counter-intuitive. Of course, I want the guests of each BWS to be excited for people who are going to be present at the brunch. I would absolutely love to show off the wicked roster of brilliant individuals each time. What ended up happening is when I did initially release the guest list, many guests did some diligence of the other attendees, and a few came to the brunch with predisposed assumptions of who the others were.

Though most tend to be relatively accurate assumptions, the brunch lost its air of mystery and curiosity which affected the guests in two noticeable ways.

  1. The guests who did their research were less curious on what they thought they knew about another guest and rarely ended up discovering the thought and emotional complexity behind social media posts, titles, and press releases.
  2. Over half of the guests who had been researched felt they couldn’t be as vulnerable as they would have liked, in efforts to “live up” to the expectations of the guests who did their research.

So, going against the grain, I decided, after the first five brunches, to no longer release the guest list prior to the meal.

In closing

With many more to follow, the lessons learned now is only the tip of the iceberg, as I continue my adventure learning from the craziest, the most curious, the most creative, and the most inspiring people out there.

À l’année prochaine!

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