Tag: quote

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VCs Are Science Fiction, Not Non-Fiction Writers

science fiction, camera lens, city

With the crazy market we’re in today, VCs are frontloading their diligence. They’re having smarter conversations earlier. Before 2021, most investors would have intro conversations with founders before taking a deeper dive into the market to see if the opportunity is big enough. Nowadays, investors do most, if not all, their homework before they start conversations with founders. And when they’ve gotten a good understanding of the market and a more robust thesis, then:

  1. They go out finding and talking to the founders who are solving the problems and gaps in the market they know exist.
  2. They incubate their own companies that solve these same issues.

Subsequently, they are more exploratory than ever before. In frontloading their diligence, VCs have become more informed, if not better, predictors of not only where the market is today, but where the market is going to be tomorrow. They have a better grasp on the non-obvious. Or at the very minimum, have a much better understanding on the obvious, so that the boundaries of the non-obvious are pushed further. In turn, they can truly invest in the outliers. Outliers that are more than three standard deviations from the mean.

Startup ideas are often pushing the boundaries of our understanding of the world we live in. The team at Floodgate use an incredible breakdown to frame the amount of data that needs to be present to qualify the validity of a team and idea. “[W]e like to say some secrets are plausible, some are possible, and some are preposterous, all different types of insights. It matters what type it is because the type of team you need, the type of people you need to hire, the fundraising strategy, the risk profile, the amount of inflections that have to come together. All of those things vary, depending on the type of secret about future that you’re pursuing,” said Mike Maples Jr. recently on the Invest Like the Best podcast.

Science fiction is, by definition, preposterous. But so are the true outliers. And as any great investor knows, that’s where the greatest alphas are generated.

Preposterous ideas are backed by logic and insight

To quote PG from an essay he wrote earlier this year, “Most implausible-sounding ideas are in fact bad and could be safely dismissed. But not when they’re proposed by reasonable domain experts. If the person proposing the idea is reasonable, then they know how implausible it sounds. And yet they’re proposing it anyway. That suggests they know something you don’t. And if they have deep domain expertise, that’s probably the source of it.

“Such ideas are not merely unsafe to dismiss, but disproportionately likely to be interesting.”

But no matter how implausible your startup idea sounds, there still has to fundamentally be an audience. And while it may not be obvious today, the goal is that it will be obvious one day. Frankly, if it’s forever non-obvious and forever in the non-consensus, you just can’t make any money there. If Airbnb stuck only with the convention industry or Uber only with the black cab, or Shopify only with snowboards, they would never have the ability to be as big as they are today.

Shopify’s Alex Danco has this great line in his essay World Building. “If you can create a world that’s more clear and compelling than the complex, ambiguous real world, then people will be attracted to that story.”

As investors, we have to start from first principle thinking. Investors, in frontloading their diligence, find the answers to “why now” and “why this”. All they’re looking for after is the “why you.” The further down the line towards preposterous science fiction you are, the more you need to sell investors on “why you”.

Idea PlausibilityKey QuestionContext
PlausibleWhy this?Most people can see why this idea should exist. Because of the consensus, you’re competing in a saturated market of similar, if not the same ideas. Therefore, to stand out, you must show traction.
PossibleWhy now?It makes sense that this idea should exist, but it’s unclear whether there’s a market for this. To stand out, you have to convince investors on the market, and subsequently the market timing.
PreposterousWhy you?Hands down, this is just crazy. You’re clearly in the non-consensus. Now the only way you can redeem yourself is if you have incredible insight and foresight. What’s the future you see and why does that make sense given the information we have today? If an investor doesn’t walk out of that meeting having been mind-blown on your lesson from the future, you’ve got no chance.

And when answering the “why you”, it’s not just on your background and years of experience, but your expertise. As Sequoia’s Roelof Botha puts it, “So what was the insight? What is the problem that you’re addressing? And why is your solution compelling and unique in addressing that problem? Even if it’s compelling, if it’s not unique there’re going to be lots of competitors. And then you’re probably going to struggle to build a distinctive business. So it’s that unique and compelling value proposition that I look for.” So before anything else, the best investors, like Roelof, “think of value creation before value capture.”

In order to find that earned secret – that compelling and unique secret sauce – in the first place, you have to love what you’re working. And not just passionate, but obsessive. The problem you’re trying to solve keeps you up at night. You have to be more of a “missionary” than a “mercenary” as Roelof would put it. If you’re truly a missionary, even the most preposterous idea will sound plausible if you can break down why it truly matters.

The Regulatory Dilemma

The most important and arguably the hardest part about writing science fiction – and this is equally true for funders as it is for founders – is that we have to self-regulate. Regulation will always be a lagging indicator of technological development. Regulators won’t move until there’s enough momentum.

But, as we learned in high school physics, with every action, you need an equal and opposite reaction. The hard about momentum, and I imagine this’ll only be more true in a decentralized world, is that it’s second order derivative is positive. In other words, it’ll only get faster and faster. On the other hand, regulation follows the afterimage of innovation. It sees where the puck was or, at best, is at, but not, until much later, where the puck is going. And truth be told, innovation will eventually plateau, as it follows a rather step-wise function, as I’ve written before. And when it does, regulation will catch up.

S-Curves
Source: Tim Urban’s “The AI Revolution: The Road to Superintelligence“

So, in the high school physics example of Newtonian physics, the reaction, in this case, regulation, needs to be equal and opposite force comparative to where the puck will be. But as you’ve guessed, that will stop innovation. And I don’t think the vast majority of the world would want that. Progress fuels the human race.

Science fiction needs rules

Brandon Sanderson, one of my favorite fictional authors, has these three laws that govern great worldbuilding. To which, he coined as Sanderson’s Three Laws. The second of which reads:

Limitations > powers

In fantastical worlds, we are often used to how awesome things can be. Making the impossible possible. But as Brandon explains, “the truth is that it’s virtually impossible to come up with a magical effect that nobody else has thought of. Originality, I’ve seen, doesn’t come so often with the power itself as with the limitation.”

As the infamous line goes, “with great power comes great responsibility.” If you end up having access to every single person on this planet’s data, what makes you a company worth betting on isn’t your power, but how you use that power. How you self-regulate in using that power. Take, Open AI’s GPT-3. Instead of sharing the entire AI with the world, they limited that power to prevent malicious actors through an API.

What does self-regulation mean? Simply, aligning incentives so that all stakeholders win. When you have two people, you have a 2×2 matrix to account for four possible outcomes. There’s a situation where both people win, two situations where one wins, one loses, and another where both lose. Needless to say, we want to be maximizing for win-win situations.

As Balaji Srinivasan said on the Tim Ferriss Show recently, “When you have three people, it’s a 2x2x2, because there’s eight outcomes, win/lose times win/lose times win/lose. It’s a Cartesian product.. […] When you have N people, it’s two by two by two to the Nth power. It’s like this hypercube it as it gets very complicated.” Subsequently, the greater the organization, the more stakeholders there, and the harder it is to account for the “win” to the Nth power outcome. Nevertheless, it’s important for founder and funders at the frontier of technological and economic development to consider such outcomes. And at what point is there a divergence of incentives.

There’s usually a strict alignment in the value creation days. But as the business grows and evolves to worry more about value capture, there needs to be a recalibration of growth and an ownership of responsibility as the architects who willed a seemingly preposterous idea into existence.

In closing

We live in a day in age that is crazier than ever before. To use Tim Urban’s analogy, if you brought someone from 1750 to today and had them just observe the world we live in, that person will not only be mind-blown, but literally, die of shock. To get the same effect of having someone die of shock in 1750, you can’t just bring someone from 1500, but you’d have to go further back till 12,000 BC. The world is changing exponentially. And new technologies further that. Who knows? In 50 years, we in 2021, might die of shock from what the world will have become.

And rightly because of such velocity, innovators – founders and investors – will have to lead the charge not only technically and economically, but also morally.

Photo by Octavian Rosca on Unsplash

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DGQ 8: What challenges are you facing right now?

tree, hand, help

How can I help you?

For those who spend a meaningful amount of time giving and helping others, that won’t be the first time you’ve heard that question. And it won’t be the last. On the flip side, if you’ve ever asked anyone else for help or advice, you most likely asked the above question yourself.

While it originates from positive intent, that question often falls short in execution.

  1. It is an open search query. Most busy people are context switching all the time. While we love spending time helping others, we don’t often think about how others can help us. I was asked this a total of 6 times over the past week, and I didn’t have an immediate answer for any of them.
  2. We force ourselves to think of an answer that isn’t always what we actually need.
  3. It shows you haven’t done your homework. I admit some people are more explicit with things they need help with publicly than others. Sometimes you’ll be able to pick up by inference, based on job title and time in their career.

Nevertheless, when you’re unable to find the answer to “How can I help you?” yourself, I default to figuring out what obstacles and challenges they’re currently facing. The question “What challenges are you facing right now?” is less of a question that is explicitly asked, but one of my main questions I need to get answered by the end of the conversation – no matter how long or short the conversation is. That said, there are fewer times than I can count where I felt compelled to explicitly ask someone I’m reaching out to help, “What challenges are you facing right now?”. I will admit I ask this quite often when catching up with friends.

So, what do I ask instead to find out what challenges the other is facing?

  1. Draw assumptions based on appearance and energy. “You look like you haven’t been able to sleep well for the past two weeks.” Then following up with, “What have you been losing sleep over?”
  2. Be willing to step up to the plate first. “I’ve been struggling with X this past week… Have you been struggling with anything recently?”
  3. Sometimes the best answers and insights you’ll get into a person’s life isn’t through just a single question. But rather, through just the flow of conversation. And subsequently, I don’t have any one-size-fit-all template to gauge that.

While I admit I’m still working on being able to close conversations well myself, being able to close a conversation is sometimes more important than the conversation itself. As Maya Angelou once said, “At the end of the day people won’t remember what you said or did, they will remember how you made them feel.” On the same token, the end of a conversation will determine the aftertaste you leave in another’s mouth.

Quite often, I find myself closing off with: “You’ve been incredibly helpful. We’ve completely run out of time before we ran out of topics, but I want to be cognizant of your time. I’d be remiss if I didn’t at least try to be the same for you.” And depending on the conversation, I’d subsequently follow up with either:

  1. “You mentioned X earlier in our conversation, and I would love to send you some amazing resources on that before the end of the day today.”
  2. “I noticed that you recently tweeted about Y, so to thank you for your time, I compiled a list of Y that would hopefully save you some time.”

Photo by Neil Thomas on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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#unfiltered #60 There’s No Such Thing As Writer’s Block

writer, inspiration, ideas, creativity

Years ago, I remember reading somewhere, “Writer’s block is not that you don’t have any ideas. It’s when you don’t have ‘good enough’ ideas.” In my opinion, one of the greatest fatalities of the 2020s is not that people lack ideas. But people have a poor way of capturing ideas when ideas do come to them.

And in the theme of ideating in the busy world we live in today, I wrote a short thread earlier this week on the seven ways I capture ideas.

  1. I carry a physical journal almost everywhere I go. Personally opt for a nice, weighty journal that I can’t wait to write in (none of that spiral bound, thin page notebooks, but that’s personal preference).
    My favorite brands: Leuchtturm1917/ Moleskine
    Page density: >150 g/m2
  2. While I’m at it, a good pen. I prefer felt tip or fountain pen.
    Psychologists do say you tend to remember thoughts more if you physically write them out, over typing them out.
    For felt tip: Staedtler fineliners
    Fountain pen: LAMY
  3. Reserve a full page for every idea. Even if your idea is only one sentence, give it space so that in the future you can come back to it and flush it out. As the wise Ron Swanson once said, “Never half-ass two things. Whole-ass one thing.”
  4. Allocate at least 10 minutes to generate ideas. Even if you can’t think of anything for 10 minutes, sit through the whole 10. A few months ago, amidst a catch-up, a founder friend of mine – for lack of better words, a serial builder, having created more apps that I can count – shared with another friend and I something incredibly insightful about finding inspiration. “Not enough people give themselves bored time. To produce ideas, you have to give yourself time to be bored.” These days, I try to allocate 30 minutes of bored time.
  5. I have a whiteboard in my shower. Yes, I take shower thoughts seriously. In fact, this blogpost originated from a shower whiteboarding session earlier this week. I’m not really picky on brand here, since it’s just to get thoughts on a board as quickly as I can, but get rain-proof markers.
  6. Handwritten notes are notoriously hard to track. So, I have a 3-step process for this.
    1. I have a table of contents at the back of every notebook. Usually reserve 4 pages for that. In there, I write down, page #, title of each journal entry, and key/most thought-provoking content.
    2. By the time I finish each journal, I revisit the now-completed table of contents to highlight/circle what resonates with me the most from that table.
    3. A few months later or 1-2 journals later, I revisit the same table of contents, browse through what I highlighted/circled, and for those that STILL resonate, I port over to my Notion, which becomes more or less my evergreen knowledge/idea hub.
  7. When I’m completely lost or need inspiration, I find that the best way to generate ideas is to ask great questions. For questions on people and passions, I’m a big fan of Tim Ferriss and Sean Evans. For startup or VC questions, I love Harry Stebbings and Samir Kaji.
  8. As a bonus eighth tip which I didn’t include in the Twitter thread, if you are still stuck, I find the question “What is the most important question I should be asking myself today?” quite useful.

Some examples of things I write in my idea journal:

  • Startup ideas
  • New things I learned in the venture capital space
  • Blogpost ideas
  • Introspective thoughts
  • Phrases and vernacular that other people say or write that I really like
  • Great questions to ask myself or others
  • Recipes I come up with
  • Dreams
  • Riddles or puzzles
  • Short stories
  • Concept art

In sum, anything is fair game. The more I allow my mind to expand without constraints, the more I’m able to draw parallels between seemingly disparate data points and create new meaning. At least for myself.

In closing

I passed by another quote over the years, and the attribution escapes me. “If you have don’t have any ideas, read more. If you have ideas, write more.” I’d extend it even further by saying, when you have a deficit of inspiration, consume. Read and listen more. There is a plethora of content out there today. And they are all more accessible than ever – from books to podcasts to articles to videos. When you have a surplus of inspiration, produce. Write and do more.

Photo by Brad Neathery on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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We’re More Similar Than You Think: The Founder and the Funder

Last weekend, I tuned into Samir Kaji’s recent episode with LPs (limited partners). Not once, but twice. And as you might’ve guessed, was damn inspired by their conversation. The more I listened to it, the more synonymous the paths of a founder and an emerging manager (EM) seemed to be. Or what I call the entrepreneur and the entrepreneurial VC. If you’re a regular here, you’ll know I love writing about the intellectual horsepower of both sides of the table. But in this post, rather than delineating the two, I’d love to share how similar founders and funders actually are.

Surprises suck, but pivots are okay

On Samir’s podcast, Guy Perelmuter of GRIDS Capital voiced: “There’s only one thing that LPs hate more than losing money. It’s surprises.”

Be transparent. Be clear on your expectations, and steer clear of left hooks. As a fund, something I’ve heard a number of GPs and LPs say is don’t deviate on your thesis. LPs invest in you for your strategy. But as soon as you deviate from that initial strategy, you become increasingly unpredictable.

Take, for example, you go to a steakhouse and order steak. But they serve you sushi instead. If it’s not good sushi, obviously you’re not coming back. Not only did they surprise you, but it was also a poorly executed one. This goes in the column of one-star Yelp reviews.

But, say it was great sushi. You had one great dining experience and you’re a happy customer. Some time in the future, you think of getting sushi again. And you remember what a great experience you had at the steakhouse. So you go back to the steakhouse, only to realize it was a fluke and the sushi wasn’t like the last time you’ve had it. Your inability to replicate surprises scares LPs, which limits your ability to raise a subsequent fund.

Nevertheless, these days markets are changing quickly. And sometimes your initial thesis may not serve you as well in today’s market as it did yesterday. As John Maynard Keynes, father of Keynesian economics, once said, “When the facts change, I change my mind.” But, if you do need to deviate, communicate it clearly, formulate a new strategy, and preemptively tell your LPs. Then at that point, it’s no longer a surprise, but a strategy. Great examples include:

  • Accelerators making discovery checks part of their core business
    • Note: LPs historically dislike GPs (general partners) writing discovery checks because they’re:
      1. Not investing via their fund strategy (i.e. typically ad hoc),
      2. Require less diligence and therefore less conviction,
      3. Send negative signals to other investors if the GP doesn’t do a follow-on check at the next round, and
      4. Because of (2) and (3) are usually cash sinks.
  • The On Deck Accelerator (ODX) – Backing founders at the earliest stages (i.e. pre-product, pre-revenue) as long as they have deep conviction in their own business.
  • The recent announcement of The Sequoia Fund – a systematic and predictable strategy to invest in not just startups, but venture funds backing incredible founders as well.

The same holds for founders. Don’t get me wrong. Startups pivot. And they should. Mike Maples Jr., founder of one of the best performing seed stage venture firms, recently shared: “Most investors are going to look at what the company does and evaluate the business for what it is, but 90% of our exit profits have come from pivots.” And just like fund managers, clearly convey why, how, and what you’re pivoting to to your shareholders. It’s always better to preempt these conversations than leave these as surprises. Often times, you’ll find your investors, having seen as many pivots as they have and knowing that is the name of the game, can offer you much more feedback and insight than you imagined for your pivot.

Optimize for the “Oh shit! moment*

In every conversation, your goal should just be to teach your investors something. An earned secret. A unique insight. What do you know that other people don’t, overlook, or underestimate? What do you know that other people would find it very hard to learn organically? This is especially true for consensus ideas – or obvious ideas. The best obvious products may seem obvious at first glance, but usually have non-obvious insights to back them up.

If you’re a fund, what is your insight – your access point – that’ll win you an asymmetric upside?

I’ve talked to too many founders and EMs that claim to be experts with X years of experience in a particular field. Yet after 30 minutes, I realized I learned nothing from them. I realize that for half an hour straight I ended up with a prep book full of buzzwords and vague jargon that would rival the SAT vocab section. But let’s be real. The SAT doesn’t get me excited to want to retake the test.

The best founders and funders out there are able to break down deep, technical, esoteric, and sometimes crazy concepts into simple bitesize ideas. The equivalent of taking the whole universe and simplifying it to its origin. A single point. The Big Bang.

I’ve also realized over the years that the world’s smartest teachers – and when you’re trying to convince people to join you in a non-obvious vision, you are teaching – lead with analogies. And the best analogies lead investors to that “Oh Shit! moment.”

COVID made capital cheaper

Equally true for startups and funds. Capital is digital. If you think about capital in the frame of investor acquisition cost, you no longer have to travel to your investors to pitch to them. This means you can take far more meetings than before. Less travel and more meetings mean your investor acquisition cost goes down.

Founders no longer have to book a week to Sand Hill Road or South Park to have introductory conversations with investors. Only to have 80-90% turn down a second conversation. This becomes even more costly the earlier you are in your startup journey. You have to have a lot more first conversations as a pre-seed founder than you do as a founder raising an A. At the same time, you have many more options for raising capital today: accelerators, syndicates, equity crowdfunding, and roll-up vehicles (RUVs). While it’s not that these resources didn’t exist before COVID, the pandemic made it much more apparent that VC money didn’t have to be the only way to raise capital. And that you can also leverage speed and your community to help you grow.

Similarly, EMs no longer have to travel across the states to talk to institutional capital. Even more so, as an EM, you’re most likely raising from individual investors. Raising a rolling fund or a 506c lets you generally solicit investments, where you couldn’t with a 506b. Subsequently, Twitter and having a community became your superpower. Mac at Rarebreed, Packy’s Not Boring Fund I, and Harry at 20VC all raised during the time of COVID, leveraging the power of their following and community to do so.

Keep it simple

“There’s no favorable wind for the sailor who doesn’t know where to go.” – Seneca

Two Saturdays ago, I caught up with my ridiculously smart engineer friend from college – “Fred”. We were reminiscing about the “good ol’ days” when we first started punching above our weight class. Particularly in regards to cold outreaches to individuals we really admired. While I was an operator at two startups that shaped my entrepreneurial career, I spent many a night struggling on how to best position our products in the market. Many hours of copy and rephrasing and reframing. In both we were competing against the existing saturation of information and solutions on the market. How do we tell our customers and investors the reason we’re awesome is because of A and B and C, and also D?

Most people, friends, customers, and investors didn’t understand the value we thought we were obviously conveying. And subsequently, we were rejected more often than I would have liked to admit. In the early days, we didn’t lose on price nor on quality, but on brand and messaging. And while we thought and strove to prove we were better in areas that mattered, both startups eventually ended up having exceedingly simple one-liners.

On the other hand, “Fred” was working on something related to liquid fuel and cold fires. Something extremely technical. But he was able to win proportionally more yes’s than I was able to. When I asked him how, he said it was simple. “We’re putting a rocket into space. That’s it. And that’s really exciting.”

I made something extraordinarily simple into something extraordinarily complex. In all honesty, I sounded really, really smart. And I felt like I was the shit. Except no one else did. “Fred” took something extraordinarily complex and made it extraordinarily simple. He didn’t sound as smart. But celebrities, sponsors, companies – people just got it.

The true value of a product is usually exceedingly simple. The fallacy of including a Rolodex of esoteric jargon comes in two-fold. Either you’re trying to sound smarter than you actually are. Or you’re trying to cram too many things in too little space. As economist Herbert A. Simon said, “A wealth of information creates of poverty of attention.”

In closing

Whether you’re an entrepreneur or an emerging manager, you’re swinging for the fences. I was chatting with an investor yesterday who had an incredible analogy. “It’s like a pinball machine. The ball goes up, and you never know how it’ll fall down. You don’t know how many bounce pads and flippers it will hit. You don’t know how many points you’re going to get. But no matter how many points you’ll get, the ball has to go up first.” Similarly, whether you start a company or a fund, you have to step up to the plate to bat. You don’t know what the upside will be. You don’t know if you’re going to return your investors 2x, 5x or a 100x.

You’re taking an asymmetric bet on the compelling future you bring. Your valuation as a startup is not how much your startups is worth, which is why the 409a valuation is always different from the valuation your investors set for you. Your valuation is a bet your investors made that you will be as big as the major players in the market. If you’re valued at $10M today, your investors are saying you are 10 in 1000, or a 1% chance, to be a unicorn. And a 0.1% chance to be a decacorn.

Valuations might seem crazy today. VC firms are also raising larger and larger funds, which lead many to be skeptical on their ability to return capital. In fairness, most funds will return a modest 2-3x over their lifetime, if at all. Most startups are and will be overvalued. On the same token, the best ones, despite their crazy price, are still undervalued. Imagine if you were an investor who could invest in Facebook’s then-unicorn valuation. You’d have made a lot of money. But we’re in an optimistic market.

At the end of the day, both parties are just managing someone else’s capital. And as such, through a fiduciary responsibility, in that regard, both are cut from the same cloth.

Photo by Luke Leung on Unsplash

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DGQ 7: If You Had To Live Your Life Over Again, What Problem Would You Have Sought Help For And Whom Would You Have Gone To?

After an investor’s recommendation recently, I stumbled on this question in an article in The Atlantic about the Grant Study. An incredible 80-year long longitudinal study following 268 Harvard-educated men and how they developed as adults. While most of the Grant Study men remain anonymous, some have publicly identified themselves, like Ben Bradlee and President John F. Kennedy. Simply put, it was history’s longest study on happiness. There were some fascinating discoveries in that study so far, like the six factors that acted leading indicators to healthy aging:

  1. Physical activity,
  2. A mature adaptive lifestyle to cope with ups and downs,
  3. Little use of alcohol,
  4. No smoking,
  5. Stable marriage, and
  6. Maintaining a normal weight.

I highly recommend reading George Vaillant’s Aging Well. If you’re short on time, Robert Waldinger’s TED talk. But I digress.

Despite always preaching to others that they should ask for help when they need it, I’m a terrible practitioner of my own advice. Sometimes I find it incredibly hard to ask for help from others. In situations I should be the expert in. In moments when I don’t think my problems are as big as others’. And in times when I don’t know what I want. While I hate to admit it, it’s often a problem attributed to my ego. And sometimes, unwittingly.

If you had to live your life over again, what problem would you have sought help for and whom would you have gone to?

The reason I love this question so much is that in asking it, we suspend our ego. It’s often easier to open up about the “[potholes] in the rearview mirror” than “[open] up about the potholes ahead” to use the words of Jeff Wald. It’s easier to answer What were you scared of as a child? than What are you scared of today?. I find it easier to:

  1. Reflect on what I should have asked for help in.
  2. Understand why I should have asked for help sooner in an empirical situation.
  3. Then use those first principles to inform me when I should ask for help now.

Your mileage may very much vary. But nevertheless, over the past week, I found it to be an interesting thought exercise to go through. At the very minimum, something to journal on.

Photo by J W on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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#unfiltered #59 I Am The Worst Marketer Out There

billboard, marketing

Last week, after a lovely conversation with a startup operator, he asked if there was anything he could help me with. I defaulted to my usual. As I’m working on being a better writer, I asked him if time permitted, could he give me some feedback on my writing. For the sake of this blogpost, let’s call him “Alex.”

While I expected just general feedback on my style of content delivery, Alex gave me a full audit of this blog. He told me I should focus, until I’ve built up an audience. He also said that I should find my top 20 blogposts, figure which category they fall under and narrow down by writing more of those. On the same token, he recommended I reference Hubspot’s “topic clusters.” Which is an amazing piece about how to nail SEO in 2021, if I say so myself. Incredibly prescient. And incredibly true.

He also recommended I use Medium or Substack over my antiquated design of a website. And forgo the header image. Which you might have noticed I haven’t (yet).

The thing is… he’s 100% right. I’ve done little right, in the sense of marketing and branding. In fact, in the Google search engines, I probably am a mess to categorize, which means I exist in no category. Even in my own words, focusing on everything means focusing on nothing. While at the time of writing this post, a good majority of my content is based in startups and venture capital. If I focused on better branding, I would have doubled down on fundraising, or marketing. Or social experiments. But I haven’t.

Truth be told, I’ve stunted my growth, or my brand’s growth, by intentionally choosing otherwise. In turn, there are only two questions I optimize for in this blog.

  1. Will this make David from yesterday smarter?
  2. Is this still fun?

I started this blog writing for an audience of one. For the person I was yesterday. And if I know the me from yesterday would love it, then I have at least one happy customer.

I don’t write this blog for profit. This blog is my de-stressor. It is my entertainer, yet also my coach. It is my confidant. And it is just fun. The process of learning and thinking through writing – refining my thoughts – gets me really excited. I don’t want to end up dragging my feet through mud. Funnily enough, despite being an extremely, and I stress the former word, small blogger, I’ve had the occasional brand reach out to sponsor content. As you might have guessed, I said “no” to everyone so far. Either I didn’t believe that the product would make the world a better place or that I just didn’t get their product. This is not to say I won’t ever take on sponsors, but I just want to be really excited about it.

I’ve also had a number of folks reach out wanting to guest post on this blog, to which I’ve also said “no” to everyone so far. Because (a) it makes me lazy and defeats the purpose of me writing to think, and (b) I haven’t learned anything from them yet.

And because I write from a motivation of “psychic gratification,” borrowing the phrasing Tim Ferriss used in his recent episode, my writing is “very me,” to borrow the phrasing of readers and friends who’ve talked to me face-to-face before. I feel I can be genuine. And I can be unapologetically curious. I can learn what I want when I want how I want. I love each topic I write about, at least in the moment my pen touches paper. It excites me. It inspires me. And it pulls me with a force I want more of.

As a product of me being me, every so often, a random essay sees a momentary breath of fame. On average, it happens every 7th or 8th blogpost. I have these random spikes of several hundred views within 24 hours every so often. And don’t get me wrong. I would be lying if I said that wasn’t gratifying as well. Other times, some essays are far more perennial and see anywhere between two and ten views a day – almost every day. There are the ones that never make it onto the stage. And live somewhere in a virtual public graveyard.

I’m publicly logging my thought process here as a bookmark for future reference. And so that my future self can’t go back in time and write off my thought processes now in a grand motion of revisionist’s history.

I also know that this won’t be the last time I revisit this topic. My future mental model might differ greatly from what it is now. As John Maynard Keynes, father of Keynesian economics, once said, “When the facts change, I change my mind.” But it might stay the same. Who knows?

I’ll keep you updated.

Photo by Bram Naus on Unsplash

#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.

Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!

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Speed As A Competitive Advantage

race car

Last week, I had an incredible fireside chat with GC’s Niko Bonatsos, who has played a key role in some incredible investments, from Livongo Health to Snap to Wag! and most recently, Saturn. In all honesty, I took much of that experience to scratch my own itch. As always, we ran out of time before we ran out of topics. But I was lucky enough to ask one of which I happened to be losing sleep over. “How do you balance speed and diligence in the increasingly competitive market of venture?”

COVID changed us

In the midst of the pandemic, COVID became a forcing function for investors to deploy capital without ever meeting founders in-person. Frankly, they couldn’t meet anyone in-person. Even if they wanted to, investors, like everyone else, was subject to a series of lockdowns, curfews, and eventually the vaccine.

Yet, as life returns to a sense of normality, many investors have gotten comfortable investing virtually. And for a handful, only virtually. At the same time, in today’s increasingly competitive venture market, capital’s become more of a commodity. And I’ve heard a number of LPs find speed to be a competitive advantage. As a product of speed, investors compete on shortened timelines. It’s a given for angels and super angels out there who have to have conviction on a fairly limited set of data. But how do top-tier funds compete in that same market yet maintain the same discipline as before?

I got my answer from Niko.

“We try to pre-empt the stuff we really care about. It basically translates to us being prepared, having frontloaded a lot of the diligence for the companies and opportunities we care about. We have a more educated conversation with the founders, and are the first ones to get to a term sheet than anyone else. That’s something we do a lot more often. And we’ve leaned into seed, which is the new series A.”

Moreover, with all the diligence they do prior to sourcing, funds, like General Catalyst and Founders Fund, have started to incubate startups where they couldn’t find solutions to problems they found.

Slowing things down

Earlier this week, over a lunch, I posed the same question to Fort Ross‘ Ratan Singh, from whom I got a slightly different variation. “VCs are doing their homework before every meeting and going in with a thesis so that they can deploy fast. VCs used to play catcher and do all their homework after the meeting. But now it’s changed, so they can say yes faster.

“While speed is a differentiator, things are moving too fast today. I met every founder I’ve invested in in-person. Even during the pandemic, I invested in seven founders, and every single one I’ve met in-person.”

To which, I had to ask, “What do you find out from meeting a founder in-person that a virtual meeting lacks in?”

Without missing a beat, Ratan said, “It’s in the small things. The way they interact with their teammates. The way they treat each other. As we finish our chat and walk back to the car, are they still an intelligent being outside of the script? A Zoom call is a 30-minute scripted call. There’s a deck. There’s the presentation they prepared. An in-person interaction is more than that.”

Ratan’s comment reminded me of something Sequoia’s Doug Leone said in his interview with Harry Stebbings recently. “It takes about thirty minutes for someone to relax, which is why I refuse to interview someone for thirty minutes.” Similarly, while a 30-minute coffee chat may just be 30 minutes, the time it takes to shake hands, order your cup of coffee, have the conversation, finish it, and walk back to your car or wait for your Uber helps anyone, not just a VC, understand so much more depth to your character.

In closing

In the words of my friend Ruben:

As if he didn’t drop enough mics in our lunch, Ratan left me with one last hot take, “In VC, you’re either asked to stay, or you’re asked to leave.” In today’s ever-changing climate, having deep domain expertise and pre-empting diligence keeps you if not ahead, at least on the curve of evolution. And for many investors, it’s one of their best bets to be asked to stay – either by the firm’s senior partners or your LPs.

Photo by toine G on Unsplash

Thank you Niko and Ratan for looking over earlier drafts.

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Why Product-Market Fit Is Found In Strategically Boring Markets

streets, ordinary, boring

In the past decade or two, there have been a surplus of talent coming into Silicon Valley. In large part, due to the opportunities that the Bay had to offer. If you wanted to work in tech, the SF Bay Area was the number one destination. If you wanted to raise venture money, being next door neighbors to your investors on Sand Hill Road yielded astounding benefits. Barring the past few months where there have been massive exoduses leaving the Bay to Miami or NYC, there’ve been this common thread that if you want to be in:

  • Entertainment, go to LA
  • Finance and fashion, go to NYC
  • Tech/startup ecosystem, go to the Valley.

While great, your early audience – the innovators on your product adoption curve – should not be overly concentrated there. All these markets carry anomalous traits and aren’t often representative of the wider population. Instead, your beachhead markets should be representative of the distribution of demographics and customer habits in your TAM (total addressable market).

While Keith Rabois could have very much built Opendoor in Silicon Valley, where more and more people were buying homes to be close to technological hubs, he led the early team to test their assumptions in Phoenix, Arizona. On the same token, Nikita Bier started tbh, not in the attention-hungry markets of LA, but in high schools in Georgia.

“Boring” virtual real estate

Strategically boring markets aren’t limited to just physical geographies. They’re equally applicable to underestimated virtual real estate. You don’t have to build a mansion on a new plot of land. Rent an Airbnb and see if you like the weather and people there first.

As Rupa Health‘s Tara Viswanathan said in a First Round interview, “Stripping the product down to the bare bones and getting it out in front of people for their reactions is critical. It’s rare for a product not to work because it was too minimal of an MVP — it’s because the idea wasn’t strong to begin with.”

As she goes on, “If you have to ask if you’re in love, you’re probably not in love. The same goes with product/market fit — if you have to ask if you have it, you probably don’t.”

Test your market first with the minimum lovable product, as Jiaona Zhang says. You don’t have to build the sexiest app out there. It could be a blog or a spreadsheet. For example, here are a few incredible companies that started as nothing more than a…

BlogsSpreadsheets
HubSpotNerdWallet
GlossierSkyscanner
GrouponStitch Fix
MattermarkFlexiple
Ghost

The greatest incumbents to most businesses out there really happen to be some of the simplest things. Spreadsheets. Blogs. Facebook groups. And now probably, Discord and Slack groups. There are a wealth of no-code tools out there today – Notion, Airtable, Webflow, Zapier, just to name a few. So building something quick without coding experience just to test the market has been easier than ever. Use that to your advantage.

Patrick Campbell once wrote, quoting Brian Balfour, CEO of Reforge, “It’s much easier to evolve with the market if your product is shaped to fit the market. That’s why you’ll achieve much better fit between these two components if you think market first, product second.”

Think like a designer, not like an artist

The biggest alphas are generated in non-obvious markets. Markets that are overlooked and underestimated. At the end of the day, in a market teeming with information and capital and starved of attention, think like a designer, not like an artist. Start from your audience, rather than from yourself. Start from what your audience needs, rather than what you want.

As ed-tech investor John Danner of Dunce Capital and board member at Lambda School, once wrote, “[the founders’] job is to find the absolute maximum demand in the space they are exploring. The best cadence is to run a new uncorrelated experiment every day. While demanding, the likelihood that you miss the point of highest demand with this approach is quite small. It is incredibly easy to abandon this kind of rigor and delayed gratification, eat the marshmallow and take a good idea and execute on it. Great founders resist that, and great investors do too.”

Spend more time researching and talking to your potential market, rather than focusing on where, how, and what you want your platform to look like. Obsess over split testing. Be scrappy.

Don’t fail the marshmallow test

We’re in a hype cycle now. Speed is the name of the game. And it’s become harder to differentiate signal from noise. Many founders instantly jump to geographically sexy markets. Anomalous markets like Silicon Valley and LA. But I believe what’ll set the winners from the losers in the long run is founder discipline. Discipline to spend time discovering signs of early virality, rather than scale.

For instance, if you’re operating a marketplace, your startup is more likely than not supply-constrained. To cite Brian Rothenberg, former VP of Growth at Eventbrite, focus on early growth loops where demand converts to supply. Ask your supply, “How did you hear about our product?” And watch for references of them being on the demand side before.

Don’t spend money to increase the rate of conversion until you see early signs of this growth dynamic. It doesn’t matter if it’s 5% or even 0.5%. Have the discipline to wait for organic conversion. It’s far easier to spend money to grow than to discover. Which is why startup life cycles are often broken down into two phases:

  • Zero to one, and
  • One to infinity

Nail the zero to one.

In an increasingly competitive world of ideas, many founders have failed the marshmallow test to rush to scale. As Patrick Campbell shared in the same afore-mentioned essay, “Product first, market second mentality meant that they had a solution, and then they were searching for the problem. This made it much, much more difficult to identify the market that really needed a solution and was willing to pay for the product.”

The more time you spend finding maximum demand for a big problem, the greater your TAM will be. The greater your market, the greater the value your company can provide. So, while building in anomalous markets with sexy apps will help you achieve quick early growth, it’s, unfortunately, unsustainable as you reach the early majority and the late majority of the adoption curve.

Photo by rawkkim on Unsplash

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DGQ 6: What three adjectives would you use to describe your sibling?

ocean, sibling

“Use three adjectives to describe your sibling. And describe yourself in comparison.”

I heard this question weeks ago from Doug Leone, Sequoia Capital‘s Global Managing Partner, on Harry Stebbings’ 20VC podcast. Known for having some of the best questions in venture and having led incredible investments into Meraki, Nubank, ServiceNow, and more, Doug loves to ask this question to founders he’s meeting for the first time. My initial response was “this doesn’t make any sense.” But in the podcast, he reveals why he loves the afore-mentioned question.

Before writing a check, an early-stage investor’s job is to answer three questions. Why now? Why this? And why you? The ‘why you’ question is admittedly one of the hardest questions to answer. Even for myself, I struggle from time to time to understand why I should scout a one founder over another over the same idea.

In a short 30 minute conversation, there’s only so much an investor can understand about a founder. There’s fundamentally a level of information asymmetry. Founders want to convince investors to take a bet on them. Yet, investors need more information to be comfortable making an asymmetric bet on them. We see echoes of a similar dilemma when recruiters interview applicants for jobs. Or when a property manager interviews a potential tenant.

Generally, recruiters, like most others, regress to questions like: “What are three of your strengths? Three weaknesses?” Having been asked so bluntly, interviewees, on the other hand, often have their guards up. They pick three strengths that would make them look the best. Equally so, they pick three weaknesses that show just enough honesty and vulnerability where they don’t get disqualified from the candidate pool. All of which exemplify pre-scripted answers.

Conversely, Doug found a way to do so without arming the interviewee’s, in this case, the founder’s, defenses. What three adjectives would you use to describe your sibling?

As Doug shares, “In a law of diversity, two siblings are less likely to be alike than two strangers. And so, how they usually describe their siblings is usually opposite of how they describe themselves. It’s a self-awareness question.”

You might realize the same principle holds when you describe a friend or a colleague or your spouse. The way you describe them often contrasts with your own disposition. “My friend is really curious.” Implicitly, you’re saying you’re not as curious.

So, the next time you talk about someone else, it’d be an interesting thought experiment to see how those same words relate or contrast with you.

Photo by Limor Zellermayer on Unsplash

The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.

Subscribe to more of my shenaniganery. Warning: Not all of it will be worth the subscription. But hey, it’s free. But even if you don’t, you can always come back at your own pace.

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Bigger Funds, Larger Spotlight, Bigger Mistakes

spotlight, bigger mistakes

I was doomscrolling through Twitter when I stumbled on Samir Kaji‘s recent tweet:

I’ve written before that the difference between an emerged fund manager and an emerging manager is one’s raised a Fund III and the other hasn’t.

In Fund I, you’re selling a promise – a dream – to your LPs. That promise is often for angels, founders, and other GPs who write smaller checks. You’re split testing among various investments, trying to see what works and what doesn’t. More likely than not, you’re taking low to no management fees, and only carry. No reserve ratio either. And any follow-on checks you do via an SPV, with preference to your existing LPs. You’re focused on refining your thesis.

In Fund II, you’re pitching a strategy – the beginnings of pattern recognition of what works and what doesn’t. You’re thesis-driven.

Fund III, as Braughm Ricke says, “you’re selling the returns on Fund I.” On Fund III and up, many fund managers start deviating from their initial thesis – minimally at first. Each subsequent fundraise, which often scales in zeros, is a lagging indicator of your thesis and strategy. And across funds, the thesis becomes more of a guiding principle than the end all, be all of a fund. There are only a few firms out there that continue to exercise extreme fundraising discipline in. Which, to their credit, is often hard to do. ‘Cause if it’s working, your LPs want to put more money into you. And as your fund size scales, so does your strategy.

Subsequently, it becomes a race between the scalability of a fund’s strategy and fund size.

Softbank’s mistake

In 2017, Softbank’s Vision Fund I (SVF I) of $100B was by far the largest in the venture market. In fact, 50 times larger than the largest venture funds at the time. Yet, every time they made a bad bet, the media swarmed on them, calling them out. The reality is that, proportionally speaking, Softbank made as many successful versus unsuccessful bets as the average venture fund out there. To date, SVF I’s portfolio is valued at $146.5 billion, which doesn’t put it in the top quartile, but still performs better than half of the venture funds out there. But bigger numbers warrant more attention. Softbank has since course-corrected, opting to raise a smaller $40B Fund II (which is still massive by venture standards), with smaller checks.

While there are many interpretations of Softbank’s apparent failure with SVF I (while it could be still too early to tell), my take is it was too early for its time. Just like investors ask founders the “why now” question to determine the timing of the market, Softbank missed its “why now” moment.

Bigger funds make sense

I wrote a little over a month ago that we’re in a hype market right now. Startups are getting funded at greater valuations than ever before. Investors seem to have lost pricing discipline. $5 million rounds pre-product honestly scare me. But as Dell Technologies Capital‘s Frank told me, “VCs have been mispricing companies. We anchor ourselves on historical valuations. But these anchors could be wrong.” Most are vastly overvalued, yet future successes are grossly undervalued.

Allocating $152 billion into VC funds, LPs are excited about the market activity and that the timeline on returns are shorter. Namely:

  • Exits via SPAC,
  • Accelerated timelines because of the pandemic (i.e. healthcare, fintech, delivery, cloud computing, etc.)
  • And secondary markets providing liquidity.

We’ve also seen institutional LPs, like pension funds, foundations, and endowments, invest directly into startups.

Direct Investments by Pension Funds Foundations Endowments
Source: FactSet

Moreover, we’re seeing growth and private equity funds investing directly into early-stage startups. To be specific over 50 of them invested in over $1B into private companies in 2021 so far.

As a result of the market motions, the Q2 2021 hit a quarterly record in the number of unicorns minted. According to CB Insights, 136 unicorns just in Q2. And a 491% YoY increase. As Techcrunch’s Alex Wilhelm and Anna Heim puts it, “Global startups raised either as much, or very nearly as much, in the first two quarters of 2021 as they did in all of 2020.”

Hence, we see top-tier venture funds matching the market’s stride, (a) providing opportunity for their LPs to access their deal flow and (b) meeting the startup market’s needs for greater financing rounds. Andreessen recently raised their $400M seed fund. Greylock with their $500M. And most recently, NFX with their $450M pre-seed and seed Fund III.

In his analysis of a16z, writer Dror Poleg shares that “you are guaranteed to lose purchasing power if you keep your money in so-called safe assets, and a handful of extremely successful investments capture most of the available returns. Investors who try to stay safe or even take risks but miss out on the biggest winners end up far behind.” The a16z’s, the Greylocks and the NFXs are betting on that risk.

Fund returners are increasingly harder to come by

As more money is put into the private markets, with startups on higher and higher valuations, unicorns are no longer the sexiest things on the market. A unicorn exit only warrants Greylock with a 2x fund returner. With the best funds all performing at 5x multiples and up, you need a few more unicorn exits. In due course, the 2021 sexiest exits will be decacorns rather than unicorns. Whereas before the standard for a top performing fund was a 2.5%+ unicorn rate, now it’s a 2.5% decacorn rate.

The truth is that in the ever-evolving game of venture capital, there are really only a small handful of companies that really matter. A top-tier investor once told me last year that number was 20. And the goal is an investor is to get in one or some of those 20 companies. ‘Cause those are the fund returners. Take for example, Garry Tan at Initialized Capital, earlier this year. He invested $300K into Coinbase back in 2012. And when they went public, he returned $2B to the fund. That’s 6000x. For a $7M fund, that’s an incredible return! LPs are popping bottles with you. For a half-billion dollar fund, that’s only a 4x. Still good. But as a GP, you’ll need a few more of such wins to make your LPs really happy.

I also know I’m making a lot of assumptions here. Fees and expenses still to be paid back, which lowers overall return. And the fact that for a half-billion dollar seed fund, check sizes are in the millions rather than hundreds of thousands. But I digress.

There is more capital than ever in the markets, but less startups are getting funded. The second quarter of this year has been the biggest for seed stage activity ever, measured by dollars invested. Yet total deal volume went down.

Source: Crunchbase

Each of these startups will take a larger percentage of the public attention pie. Yet, most startups will still churn out of the market in the longer run. Some will break even. And some will make back 2-5x of investor’s money. Subsequently, there will still be the same distribution of fund returners for the funds that make it out of the hype market.

In closing

As funds scale as a lagging indicator of today’s market, the discipline to balance strategy and scale becomes ever the more prescient. We will see bigger flops. “Startup raises XX million dollars closes down.” They might get more attention in the near future from media. Similarly, venture capitalists who empirically took supporting cast roles will be “celebretized” in the same way.

The world is moving faster and faster. As Balaji Srinivasan tweeted yesterday:

But as the market itself scales over time, the wider public will get desensitized to dollars raised at the early stages. And possibly to the flops as well. Softbank’s investment in Zume Pizza and Brandless turned heads yesterday, but probably won’t five years from now. It’s still early to tell whether a16z, Greylock, NFX, among a few others’ decisions will generate significant alphas. I imagine these funds will have similar portfolio distributions as their smaller counterparts. The only difference, due to their magnitudes, is that they’re subject to greater scrutiny under the magnifying glass. And will continue to stay that way in the foreseeable future.

Nevertheless, I’m thrilled to see speed and fund size as a forcing function for innovation in the market. There’s been fairly little innovation at the top of the funnel in the venture market since the 1970s. VCs meet with X number of founders per week, go through several meetings, diligence, then invest. But during the pandemic, we’ve seen the digitization of venture dollars, regulations, and new fund structures:

Quoting a good friend of mine, “It’s a good time to be alive.” We live in a world where the lines between risk and the status quo are blurring. Where signal and noise are as well. The only difference is an investor’s ability to maintain discipline at scale. A form of discipline never before required in venture.

Photo by Ahmed Hasan on Unsplash

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