Tag: vc

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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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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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The Secret Sauce

Photo by Aarón Blanco Tejedor on Unsplash

I was chatting with a founder yesterday about why she was getting so many “maybe’s”, a few “no’s”, but no “yes’s”, where a “yes” needs to come along with a term sheet, or else it’s as good as a “maybe.” Her product was hitting most of the check boxes for a startup ripe for the seed round, but she just wasn’t getting any traction from investors. There were a few KPIs she was missing here and there, but most startups don’t fit in the cookie cutter rubric anyway. So why?

It was and is the secret sauce. Others might call it the X-factor. It’s what uniquely sets you, as a founder, and your team and product apart from the rest of the competition. Like I mentioned in my thesis, what did you catch that makes money, which everyone else underestimating or missing entirely? It could be an insight; it could be a business model; it could be a specific money-generating collective customer insight. And how will this secret sauce continue to help you gain traction, at the minimum, for next few years. Moreover, at an early stage, pre-product-market fit (pre-PMF), it really only has to be one thing. It doesn’t have to be a list of the five ‘unfair advantages,’ like they teach in B-school. It’s not the chart with you having all the check boxes checked and everyone else having less checks than you do. It’s more often than not, not the up and to the right graph that you have in your slide deck. Because let’s be honest, every startup’s graph is up and to the right. Left side – antiquated. Right side – revolutionary. Bottom side – slow. Top side – fast. Or some cousin of that. Not that any of these advantages, charts and graphs are wrong, but what they represent most likely isn’t as unique as a founder might think. VCs see thousands of pitches in their inbox, pitches at events, and pitches in person. What you think is unique may be the 50th time a VC sees the exact same value proposition. As one of my 6th grade teachers once put it into perspective for me, “Think of a hundred really, really creative ideas. Throw them all away because all of them are unoriginal. Now think of your next hundred, and you are finally entering where no one has tread before.”

Just one thing. One thing I, as a scout, or another as partner, can bring to a partner meeting and say: This one thing is why we should invest. The more intuitive, yet exclusive to you, the better. Investors only have so much bandwidth to entertain ideas. There is a huge sum of okay ideas. Many good ideas. A few crazy ideas. And an even smaller handful of crazy good ideas. And the secret sauce is to prove to anyone exactly why you are one of the crazy good ones.

Now the secret sauce gets more nuanced here. You and your startup not only need that secret sauce, but you need to make sure the investor that you’re talking to is the “best dollar on your cap table,” as Roy Bahat of Bloomberg Beta (yes, the link redirects to a Github link, and they might be the only investors out there that does that) puts it. Why is it the perfect fit for the investor you’re chatting with (or going to chat with)? And why is that investor, and no one else, uniquely suited to help your business flourish at this stage? For example, I can cook up the meanest mushroom dish ever, slather it with my widely-accepted secret sauce (which has white pepper in it), and give it to my brother. No matter how good it actually is, he will without a doubt throw it in the trash or flush it down the toilet. Because he’s just not into mushrooms. The same can be said with investors. If they can’t or don’t know how to appreciate, savor and help you build on that delicious mushroom recipe, you’d just be wasting time barking on the wrong tree.

All in all, the secret sauce is just when your unique recipe for success meets someone with the means and experience to love it.

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Why I jumped into VC

I’ve always had a life goal of meeting, learning, and helping the craziest, most creative, and most inspiring people in the world (and maybe one day, outside of it). So, half a decade ago, I made that dream-like goal my mission. Every week I reached out to one new person I was insanely excited about, which sounded great in theory, but scared the hell out of my introverted self. I would find the person of the week (POTW, as I would abbreviate it in my journal) from anything that would spark my interest: articles, podcasts, books, friends (and our online and offline conversations), memes, or YouTube videos. I then forced myself to find every way possible, and over time, figure out the best way possible, to meet these brilliant folks. It was a trial-and-error game of email, call, warm intro, Instagram or LinkedIn DMs, hand-written letters, and even attempting to show up at their office and ask for a meeting unannounced. Most were in vain, but those that I did succeed in, always had me jumping with joy, which was quickly followed by nervous adrenaline, as if I had overloaded on caffeine.

But that’s what made every single week fun. Every week I had something to look forward to – a mission that I would jump out of the bed every morning to accomplish.

That’s exactly why I didn’t give myself time to blink when I got the chance to jump into venture capital. Venture capitalists have a great track record of finding and investing in brilliant and passionate dreamers. And when I had yet to find my own systematic calculus for finding fascinating humans of the world, the mysterious land of venture capital would help me gain insight and a means to create my own. At the same time, I just couldn’t ignore my former professor’s description of the VC industry:

“A career where you get to see the future from one person’s perspective. And if you piece enough of them together, you’ll be able to help build the future you want you and your children to live in.”

Though I’m still only a meager three years in, and many miles short of having children, I’ve learned VC is a much more complex beast than I initially thought, but it doesn’t change my mission: to meet, learn, and help the craziest, most creative, and most inspiring people in this world. As someone who’s on the more junior side of life, there has been no better industry for me to learn, in breadth and in depth:

  1. How to start and grow a business,
  2. The frontiers of technology,
  3. And the fundamentals of human relationships.
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My Thesis (2019)

I jumped into the fascinating world of venture capital about three years ago. It’s not like I planned it out or had a life-long dream of being in VC. Maybe it was a result of too many bedtime stories from my dad or maybe it was my admiration of Remy from Pixar’s Ratatouille. Either way, I just knew I was enamored innovators and their stories.

Three years in, I don’t claim to know everything, or even anything. After all, a brilliant veteran investor once told me:

“You won’t know if you’re good at it until you’re ten years in.”

And it just so happens that ten years is the average lifetime of a fund. As of now, I’ve accrued quite a bit of unrealized IRR – less so monetarily, but more so in terms of pattern recognition. In this cycle (as I believe, rather than psychology’s four linear stages of competence) of incompetence and competence, I know what I don’t know – my conscious incompetence. But here is what I do know – my (hypo)thesis after reading thousands of pitch decks, meeting 700+ founders and learning from 100+ investors. Granted, a mix of pre-seed, seed, and Series A folks.

Why this?

The first leg of my thesis happens to be the most explicit, and often times, the easiest for founders to answer. Why are you pursuing this problem? What makes your solution appealing to people currently facing this dilemma? And, how are you different from your direct and indirect competitors?

‘Why this?’ is, simultaneously, a question about product and market. How does this product fit in the larger picture of the market? Is the market well-defined, growing, or nascent? How saturated is the market? What is everyone else missing entirely or underestimating?

Why now?

What market forces, technological advancements, and/or social dynamics have made this problem ripe for the taking? Timing is crucial for startups. Too early, the stage has yet to be set. Had Uber or Lyft been founded prior to the smartphone, it would have folded in the blink of an eye against the looming giant of taxis. Same if coding bootcamps came before demand exceeded supply of software engineer roles in technology. Too late, and you’re feeding on scraps, if at all.

Often times, there’s more than one team that realizes the intersection of social, technological, political, and economic trends at the same time. But each might have a unique perspective on why the intersection came to be. The question I ask myself when looking at each potential investment is: What did you catch that makes money, which everyone else underestimating or missing entirely? Of course, it does make it easier when the founder(s) help spell that out for me.

Why you?

Early-stage investing is mostly about the founders, especially when there’s so little numeric evidence the earlier the stage is. Their obsession (similar, but not the same as passion), their grit, their domain expertise, their chemistry, and their ambition.

Obsession. Passion is what keeps you going during the day and when you have free time. It’s what you love. For example, there are many things in this world that I love: swimming, art, travelling, and eating, among many others, but I would never throw away my life to pursue these. After meeting with hundreds of founders, I learned it’s easy to mistake eagerness for passion, especially during the first 30-minute coffee chat. Obsession, on the other hand, is what keeps you going during the night, while burning the midnight oil. It’s what you hate. It’s a personal vendetta, which is catalyzed by a problem that you face first-hand, rather than through market diligence. As one of my good founder buddies, Mike, prompts it:

“How you sleeping?”

On the same token, obsession is contagious and inspiring. It is a key quality I look for, which can reasonably help predict how proficient an entrepreneur is and will be in hiring early team members, as well as onboarding future stakeholders.

Grit is a function of obsession. The more obsessed you are, the easier it is to weather through obstacles during the founding journey. It’s a trait I learned to recognize as a former competitive swimmer. The more obsessed I became with a achieving a certain time, the easier it was for me to overlook the short-term pain for the long-term gain. I could put in 40-hour swim weeks and still be as eager and excited coming out of them. Similarly, I’ve seen obsessed founders be able to pull off cup ramen meals, moving from comfortable houses to stuffy 2-room apartments, and taking rejection after rejection from investors, friends, and family. With limited resources, how much cognitive flexibility does the founding team have? I’m not saying that founders need to live in a garage and have cold pizza to be successful, but I do want to see founders’ ability to be scrappy and resourceful, like Brian Chesky and his team at Airbnb went to each of host’s house to take high-quality pictures for the site or when Michelin created the Michelin Guide for restaurants to help sell their tires.

Domain expertise. One of my favorite questions to ask founders is: “What is each of your competitors doing right?” It’s easy to get bogged down in the thought process of “I’m right, you’re wrong” and many founders that I’ve seen do end up living in a bubble of how “unique” (whether true or not) they are. What separates a good entrepreneur from a great entrepreneur is the ability is to ability to adapt and be open-minded about the changing landscape, which includes getting to know your market, and subsequently, competitors, like the back of your hand. Domain expertise isn’t just understanding the market, the product and the team, but also having accumulated deep, unique insights into all the above and being able to defend each insight. It is one of the few traits that I look for that cannot be static and should grow over time.

Chemistry. Rather than asking how long co-founders have known or worked with each other, I found it more insightful to ask how co-founders would resolve problems between themselves and their first impressions of each other. Both provided me with context on whether pressure and friction can create gems or mashed potatoes.

Ambition. When I first entered the world of venture capital, I thought ambition was a given. I mean, who would want to create a startup if they weren’t ambitious? Over time, I learned there were varying degrees of ambition. Some envisioned transforming an industry, some wanted to be acquired, and some just wanted to be their own boss. None are better or worse than the others, but not all are suited for VC financing. VCs bet big to win big. I’ve watched VCs turn down many great ventures, just because they couldn’t justify their potential ROI to their team, fund, and/or limited partners (LPs for short – the folks who invest in VC funds). Why? VCs take on big, but calculated risks. Because of that philosophy, they expect many misses, but for each investment, they’re hoping that that venture makes back a majority of their fund, if not more. Of course, there are a few other factors that determine VCs return on any investment, but at the very early stages, it’s the first check mark entrepreneurs have to check. You can only catch as much fish as how wide the net you cast.

Conclusion

The uncomfortable truth, especially in the San Francisco Bay Area, where people from around the world come to build a dream, is that not all ventures are meant for the venture capital model. VCs ask founders to tackle aggressive schedules and metrics, whether it’s the Rule of 40 for SaaS startups, or the minimum Month-over-Month growth of 30%, as I was first taught. There are many profitable startups and brilliant builders out there that are excluded from the VC model.

My friends and colleagues call it my NTY thesis – the millennial abbreviation for “No thank you”. When I first started scouting, it was all about finding the best ones out there. It was saying “yes” to each opportunity to each conversation – quantity. But when I reached critical mass, had started developing an investment thesis, in conjunction with learning how other theses came to be, it wasn’t about quantity anymore; it was about quality. It wasn’t about finding; it was about eliminating. The hardest part for me was turning my eager “yes’s” to reluctant, but necessary “no’s.” A good mentor of mine once said:

“If you can’t say no, don’t invest.”

Although I have yet to invest in these startups, the calculus is the same. I really boil it into one final question: Am I willing to risk my political or social capital with my connections for your venture? Is there something about the founder and/or startup I can nerd out about? It could be an extraordinary track record for getting shit done. It could be brilliant traction. It could be a unique insight. What really tips the scale is the secret sauce.

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