Month: December 2019

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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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Pre-gaming Cold Emails

It’s the holiday season again – my favorite time of the year! From Glühwein to Christmas lights and decorations, it’s the perfect time of year to tackle on many things that bring us cheer. When it comes to the people around us and in our lives, the holiday season is my favorite excuse to catch up with old friends and meet new folks.

‘Tis the Season to Reach Out

Outside the exciting, but tough world of venture capital and entrepreneurship, I enjoy spending time meeting brilliant individuals outside of the technology sphere. To the point, I made a New Year’s resolution half a decade ago that I’m going to meet one new person I’m crazy passionate about every single week. I’ve stuck with that resolution ever since. Obviously, it required me to find a way to get in contact with these amazing folks every week. From cold emails to calls to handwritten letters to knocking on their front door, whether it was going to be a success or not, each week provided me with a new challenge I get excited to embark. And I’ve found that I get the highest positive response rate out of my 52 weeks a year, the five to six weeks starting from Thanksgiving week until the first week of the new year – or in this coming year’s case, the new decade. Over the holidays, it’s true that people don’t check their inboxes as frequently, but it seems that most people who plan to reach out believe that too, and often stall until the new year, at least many of my friends and coworkers do – a sort of New Year’s resolution. Of course, I’m not saying there’s any guarantee in a positive response, but chances do seem higher.

I’d like to start off by saying that in the context of reaching out to individual people that I can imagine becoming friends with, I don’t have any holistic templates for cold emails, outside of a few sentences, which I’ll share in this post. To me, writing a cold email is a labor of love, and it really pays off when I make the content as relevant to the addressee as possible. On the flip side, if the purpose is to spray-and-pray or to gain leads in a funnel, this post may not be entirely pertinent, though there may be sprinkles of fortune scattered below in how I explore the mental maze in sending a cold email.

The Warm Up

Having spent almost a decade in competitive swimming, the first, and probably the most rewarding, yet most underappreciated, exercise I learned was visualization. Visualization comes in two parts: 1) Seeing myself win the race and get my desired time, and 2) Being prepared for any possible resistance or friction to winning. Don’t get me wrong; the race itself is important, but about a year into my swimming career, I started competing increasingly with athletes that were of a similar caliber as I was, where the margin between our best times existed in the milliseconds. And arguably, what makes or breaks the race is how mentally prepared you are before your race even begins – what all the 30-40 hour training weeks will amount to.

It’s the same when I send cold emails. I used to think I was special, having gotten into an amazing university, some of the most competitive and “elite” organizations on campus, and so on. Truth is it was all bullcrap! And sending those cold emails was one element that grounded me. A cold email is nothing but another tick in their inbox – nothing more, nothing less. I’m not allocated more real estate on the virtual battlefield. In fact, in some ways, you could even say I can’t even pay-to-win. If I’m punching above my weight class, then I was and am another competitor, competing for a limited, finite resource: attention.

Jeff Bezos once said:

“If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people, because very few companies are willing to do that.

“At Amazon we like things to work in five to seven years. We’re willing to plant seeds, let them grow and we’re very stubborn. We say we’re stubborn on vision and flexible on details.”

Although he said this in relation to building a company, it’s equally true in the competitive landscape of sending a cold email. You have to be willing to push your time horizon beyond any of your competitors. Or in other words, be prepared to go the distance – to play the long game.

What does that mean? Any permutation of creativity juices, like letters sent via messenger pigeon (or turtle doves for this time of year), and recurring emails works. The most important thing to keep in mind, when playing the long game, is cadence and commitment. My default is usually one email a week, usually Monday or Tuesday morning, up to three weeks, with each one showing the positive delta in knowledge acquisition compared to the past week, but still need help in their respective expertise on a particular topic.

Some of my friends and founders I met have tried more extreme versions of what I do. For example, one persistent founder I know once sent the same email every day at 9AM for three months to finally get a meeting with an executive at a major entertainment studio. Another sent the same pitch email to a well-renowned investor every week for a year, and now they’re best buds and play pick-up games every month. The disclaimer is that these may be edge cases, but do be cognizant to never overstay your welcome. If you’re asked to stop, stop.

When should I send a cold email?

On a macro scale, two overarching themes that run in my head are my personal resource availability and timing.

Personal Resource Availability

Outside of the obvious answer of trying to get in touch with someone outside of my immediate network, the question would be better phrased as: When can I not get a solid warm intro? I used to think all warm intros were the same, and that a warm intro is always better than a cold email. Truth is: it’s not always. There’s a huge spectrum to how great (or not) a warm intro can be.

Let’s think about it from the perspective of a Net Promoter Score (NPS). We may all be familiar with the question:

One a scale of 1-10, how likely are you to recommend this product to your friend?

We’ve most likely seen it when filling out a survey after you used or bought a product or service. It’s how businesses measure your satisfaction of their product or service. Although one might think that five is average, anything greater than five is above average, and anything less is below average, the truth is most people regress to filling out ‘7’. ‘7’ is a proxy for not offending anyone but at the same time, saying the the product or service was “okay.” Businesses usually measure 7’s and 8’s as okay, where the real breadwinners are the 9’s and 10’s. Similarly, when I seek or decide to give warm intros, it really comes down to: Can I get or give a 9 or 10-score warm intro? In my head, it subsequently creates a binary scale: a solid warm intro (score = 9 or 10) and a weak warm intro (score ≤ 8).

Subsequently, when should I send a cold email is answered by… whenever I can’t get a solid warm intro.

Solid Warm Intro > Cold Email > Weak Warm Intro

Now, it begs: what are the characteristics of a warm intro? This is decided in two parts: content and matchmaker.

I characterize content in three parts: the subject, the introduction, and the ask. The subject is meant to attract and describe the purpose of the email. The introduction is to explain who I am. The ask, and probably the most important bit, which has to be clear from the beginning, is what I want out of the introduction. With the first introduction, and also for the cold email, I keep it simple to one of two things, depending on the other person’s bandwidth:

  • A 20-minute call or in-person chat (Note: If I go with this option, and the person accepts, I follow up with 2-3 questions I plan to ask during the chat)
  • One burning question

To make it easier for the matchmaker, I often send them a short two to three sentences that summarizes the above, and can easily be forwarded along. My goal is to make it as easy and simple for both the matchmaker and the person I want to get in touch with.

The matchmaker, or the person referring me, is any one or a combination of the following:

  • A subject-matter expert (SME) in my respective field, defined by having a track record for success and external validation by other thought leaders;
  • Someone who knows me (and my work) well, capable of succinctly describing what I’m working on and me, and is excited for me;
  • And/or, someone who knows the person I want to get in touch with well, where the matchmaker is either the first 100 names the person receiving the introduction thinks of, or the first five names in that given field.

Timing

Timing is crucial. And to measure it, I ask myself four questions:

  1. Where are they (in life)?
  2. Where am I (in life)?
  3. What is my purpose?
  4. How can they win?

Where are they (in life)? Is the person I want to get in touch with busy tackling a new project? Preparing for a new baby? Switching careers? On a holiday vacation? If the person has a large presence on social media, most of these can be found online. Take special notice of the inflection points and outliers in their life. Some are more obvious than others. Of course, they’ll be willing to talk about the moments in their life when their second derivative was positive, but I think there’s a bigger story behind the moments when second derivative was negative. Of course, it may be something I bring up later in the conversation depending on how openly vulnerable the person I’m reaching out to naturally is. If the person has a limited presence online, it’s best to ask the matchmaker or mutual friends and connections. Sometimes, I just can’t find evidence of his/her bandwidth anywhere, so I preface my cold email ask with:

I know you’re extremely busy as is. If this does surface in your inbox and you have the time to reply, I’m grateful if you could [insert ask]. Otherwise, I’ll reconnect in one month.

Leaving room for people to not feel bad to say no, and making sure to follow up have been the two hallmarks for me to potentially get a “yes” in the future. A “no” now isn’t a “no” forever.

Where am I (in life)? Have I done all the diligence I could possibly do before I reach out? Anything that is “Google-able” is not worth asking another individual, especially if I’m looking to punch above my weight class.

What is my purpose? Why am I reaching out? What makes this person special? Why might this person be the only one in the entire world who can answer my ask? If I’m reaching out in the networking sense, can I be this person’s friend for at least the next decade?

How can they win? Always give before taking. There’s plenty of literature online, explicitly and implicitly – on social media, in the news, in their public appearances – that would help arrive at what they might need. If I have to ask him/her how I can help him/her, then I’m already wasting that person’s time.

In closing

In a saturated market of information, product-market fit is defined by attention. So keep it personal. Keep it direct. And have some fun.

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Finding Product-Market Fit and “Idea-Market Fit”

Photo by Loic Leray on Unsplash

I was recently inspired by a fascinating conversation between Mike Maples Jr., co-founder and partner at Floodgate, and Andy Rachleff, co-founder of Benchmark Capital and Wealthfront, but more interestingly, the founder of the term, product-market fit, or PMF – a term that signifies when a product is recognized by a strong demand in the market. Over the years, there have been various ways entrepreneurs, go-to-market strategists, and investors have defined when an idea reaches product-market fit. But before I dive into the PMF, let’s take a look at market definitions first, which admittedly is a step off the beaten path.

The Markets

How I Like to Think about Market Sizes. *Not drawn to scale

Traditionally, the total addressable market (TAM), serviceable addressable market (SAM), and the serviceable obtainable market (SOM) are defined according to the geographic location of your market. It makes sense – your market is as big as where you can offer the service. But now, in an increasingly connected world, technologies are less and less inhibited by the geographical boundaries that plagued the decades before. That said, there are still cultural, social and economic differences when accessing new demographics, which is why I like to characterize the TAM, SAM, and SOM by psychological resistances to new ideas. The TAM is still defined by the total upside potential of a product, where it still excludes laggards, or folks who would most likely never (seek to) use your product. The SAM is construed of people who would use the product after three to five friends in their network recommend and are using the product themselves. And finally, the SOM consists of customers who are desperate, as Andy Rachleff called it, for your product. They have spent sweat, blood, and tears finding or building their own solution. They have already traversed the idea maze themselves and put the dollar (or the euro, peso, krone, pound, yen, RMB, BTC, ETH… you get my point) here their mouth is at. And here, in the SOM, is where you find your product-market fit.

Product-Market Fit

PMF is most noticeable on the hockey stick curve. Before PMF, traction is slow and looks very much like the blade of a hockey stick. And after PMF, traction skyrockets and exemplifies exponential growth.

The Hockey Stick Curve

While there are many heuristics to assess PMF across different verticals, I’m the most fluent in consumer tech where I’ve spent most of my time in. And in consumer tech, I’d like to underscore the notion of ‘exponential organic growth’, and subsequently, a short analysis on each word of that phrase.

Exponential is probably the most straight-forward, where at the early stages of a business, we’re looking for rapidly compounding growth.

Organic growth, as opposed to paid growth, is a measurement for word-of-mouth. Investors tend to measure the effectiveness of a product by its virality from its initial customers to its nth customer – growth that is achieved without directly spending (ad) dollars on acquiring the new customers.

Growth is something I break down into – retention and adoption. Increasing adoption is great as measured by the growth of total users on consumer platform or for a consumer product, but focusing only on adoption leads to a leaky funnel, or in my case, trying to hold too many groceries in my hand without a shopping cart. Every time I grab another item on the shopping list, I drop some other item I was already trying to balance and hold. Of course, focusing only on retention means there’s no growth, which for keeping your best friend circle is fine (unless you want a thousand BFFs), but not for growing a startup.

Below are some growth signs to pay attention to signify that your product is near/at PMF:

RetentionAdoption
> 25% DAU/MAU 100s of organic signups/day
40% are active day after signup> 30% MoM growth
Usage 3 days out of every week

“Idea-Market Fit”

As a founder with an ambitious idea, reaching product-market fit is a great goal to have, but the truth is PMF is a mystical beast – a chimera – in and of itself. Market demands change; what satisfied the definition of PMF a decade ago may not satisfy it now and will most likely not satisfy it ten years from now. Many studies have shown that most startups don’t fail from technological risk, but rather the inability to reach PMF, which ends up leading to lack of investor interest, demotivation, and the founding team falling apart. And quite obviously, before you reach PMF, the hardest part about starting a business is reaching PMF, or what Peter Thiel and many call the Zero to One. I’ll dive into the lessons I learned about the journey to “1” in future posts, but for the purpose of this post, I’m going to focus on the “0” – or what I like to call, “idea-market fit“, or IMF.

What differentiates a good idea from a great money-making idea? I’m going to borrow Andy’s thought calculus exercise. In a 2×2 matrix with right/wrong on one axis and consensus and non-consensus on the other, “you want to be right on the non-consensus.”

Andy Rachleff’s 2×2 Startup Idea Matrix

Why? Discounting the situations where you’re wrong (because you don’t make much, if any money), if you’re right on consensus, it means the market’s already mature, and perfect competition in a capitalistic market squeezes you out of your profit margins. If you do pursue this option as a founder, you’re more or less tackling an execution risk. On the other hand, if you’re right on the non-consensus, the market is still nascent, and you have the potential for monopolistic control of the market. In other words, you’re taking a market risk.

It definitely isn’t intuitive. At the very least, it wasn’t to me when I was on the operating side of the table. I wanted validation. When I was at Localwise helping build a community of local talent, I wanted people to say “I totally agree” or “You’re onto something.” But often times, I just received friction and resistance, with the toughest to receive from some of my friends.

“No one would ever buy that.”

“You’re wasting your time.”

“When are you going to get a real job?”

And at some points in time, I did think, “Maybe they’re right.” Until I started meeting a few people who thought a hiring destination for local mom-and-pop shops wasn’t a bad idea, and especially when small business owners started opening up about their frustrations. Hiring platforms, at that time, focused on the sexier brands and companies to get more demand side traction – the Googles, the Big Four’s, or the Bains, but had seemingly completely underrepresented the population of local businesses. Even if these SMBs were on these other platforms, they were overshadowed by the presence of bigger brands.

When validating startup ideas, you don’t want consensus. If your idea is truly revolutionary, people have yet to be conditioned to accept the idea. Take Uber or Airbnb, for example. If you asked the average person if they would use such a product, most would have thought that you’d be crazy to have a stranger sharing a car ride or home with them. These days, take e-sports or streaming. If someone told me in my pre-teen days that I could make a living off of playing video games, I’d most likely think I was dreaming. After all, I grew up playing Snake on my dad’s Motorola Razr, which admittedly seems to have made a return to the markets.

IMF is about challenging convention and the status quo. That’s what makes an idea revolutionary, or as people in Silicon Valley like to call it, disruptive. A crazy good idea challenges the explicit and implicit biases we have about society and ourselves. In other words, we have to detect the deception we bestow onto ourselves to find the gems in the rough, which Josh Wolfe of Lux Capital explains in his 2019 Lux Annual Dinner Talk – one of the best VC thesis-driven thought pieces I’ve ever seen.

In closing

As a geeky quote collector, I’d like to close this piece not in my own words, but in the words of three brilliant investors who have a few more patches of scar tissue on their back than I do now.

“Some of the best ideas seem crazy at first.”

– Curiosity, in my Thanksgiving blogpost

“Most of the big breakthrough technologies/companies seem crazy at first: PCs, the internet, Bitcoin, Airbnb, Uber, 140 characters…you are investing in things that look like they are just nuts… it has to be something where, when people look at it, at first they say, ‘I don’t get it, I don’t understand it. I think it’s too weird, I think it’s too unusual. “

– Marc Andreessen

“Breakthrough ideas have the traditionally been difficult to manage for two reasons: 1) innovative ideas fail far more than they succeed, and 2) innovative ideas are always controversial before they succeed. If everyone could instantly understand them, they wouldn’t be innovative.”

– Ben Horowitz, in his new book What You Do Is Who You Are
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A Little Perspective on Intuition

I was chatting with an artistic buddy of mine about the parallels between craftsmanship and early-stage investing, and the more we dove into it, the more fascinating it became. Very similarly, Ash Fontana of Zetta Venture Partners provides a fresh perspective in an episode, specifically, at the 28:45 mark, on The Twenty Minute VC. But one thing, in our conversation, stood out to me in particular – where, somehow, I never put two and two together – intuition.

As you might’ve noticed on this blog already, I’m obsessed with intuition. I’ve asked many an investor to try to break down their intuition, or unconscious competence, hoping to learn from them in tandem with entrepreneurs I have met over these days. I’ve also asked experts from various fields – music, cinematography, culinary, sports, politics, and more – about their various forms of muscle memory. And my conversation with my buddy reminded me of a short journal entry I wrote over a decade ago, about the first person who described intuition to me:

It was late that summer night. The sun had already set, and the crickets had come out center stage in tonight’s feature performance. The slow chorus of whirring was accompanied by the occasional electrical spasms of the 20th century street lamps right outside the studio.

I was helping my teacher pack up the last of his art supplies and move it to the rusty, old shed in his backyard. As I put all the brushes and paints in their respective shelves, I couldn’t help, but notice an array of canvases lying in the left corner. As my curiosity ended up getting the better of me, it turned out to be a series of beautiful and complex surreal, abstract, and Chinese watercolors – quite the contrast to his usual realistic style.

“What do you think?”

“It’s beautiful,” I replied, as if on autopilot.

He paused for a second.

“David, do you know what the toughest thing to draw is?”

“Maybe this,” gesturing at the canvases I was flipping through like a Rolodex. “Oh! And monsters.”

“I don’t think so,” shaking his head, “it’s humans.”

I couldn’t help but pop my favorite question, as a 9-year old, “Why?”

” ‘Cause we see them every day – on the streets and at home, angry and calm, wrinkled and not, and from the day we’re born till the day we die. So, the smallest of deviations from what we’re familiar with is recognizable, not just to an artist, but any person. The average person may not always know why and how it doesn’t look like the people they’re used to seeing, but they will always be able to tell the difference, before you have a chance to blink.”

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