Not too long ago, I published a blogpost walking through my top 9 founder questions that deserve more attention. In it, I detailed:
The questions
My rationale for asking each of them
Surprisingly, it did really well. A few folks reached out to me before that post, which inspired its due subsequence, asking if I had a repository of questions to share. And after, asking me to do more of such calculi.
Just got asked by a friend on how I come up with questions.
1st thought, idk it just happens.
2nd thought, naw, I know I spend too much time swimming in my head.
So here's a thread 🧵. Hope it's useful to someone out there (Or an excuse to say I worked today):
While I’m compiling something of the like on the backend, with no real deadline, as it’ll grow over time, I thought I’d dedicate a series on this blog to new and old questions that come into my purview. Each paired with:
Why I ask it the way I do
In what circumstances do I find myself asking it
And if applicable, how I build up to asking that question
And as bowtie to wrap everything up nicely together, I’m calling it the DGQ series. Or Damn Good Questions. Or it’s counterpart, Dumb and Garbled Questions. I’ll let you decide what each question stands for. But I’m really not the best with naming conventions, so if anyone has a better one, I’m all ears.
As the rocket takes off, I thought I’d begin by sharing the question that inspired me to start this new series.
What would [20+age] year old [name] say about the [name] that sits before me today?
For instance, what would 45-year old David say about the David that sits before me today?
I’ve heard many variations of this question, but the wording of this question in particular is an ode to my buddy, Matt, founder of nomofomo and UCLA’s President of Thought Lounge. After all, many of the best ideas I have in my noggin’ right now are not my own. This question is no exception.
There’s this great line from the song A Million Dreams, which I’m going to spare you my sad excuse for a karaoke singer, that goes like: “I don’t care, I don’t care, so call me crazy. We can live in a world that we design.” As luck would have it, I found it when I read Mike Maples Jr‘s piece from last year on backcasting. Which, if you have a spare 10 minutes, I highly recommend checking out as well. And speaking of quotable lines, he wrote, “The future doesn’t happen to us; it happens because of us. The future is not like the weather. It doesn’t just happen. People make the future. It’s not a destiny or hope; it’s a decision.”
He goes on to say, “Breakthrough builders are visitors from the future, telling us what’s coming. They seem crazy in the present but they are right about the future. Legendary builders, therefore, must stand in the future and pull the present from the current reality to the future of their design.”
Similarly, not only the greatest founders, but I also found that the greatest life athletes live in a similar mantra. It takes real courage to stand where no one is standing and decide that is the direction you want to pursue. You might be right; you might be wrong. But there’s something to be said about the clarity you will have when you live life under the assumption that you’ve already done it.
For example, I suffer from stage fright. But I find great comfort in visualizing myself doing what scares me the most again and again, until I get comfortable standing on stage. Imagining myself giving the same talk in front of one friend, 10 friends, 50 people and even 5,000 people. Each time I level up, I imagine the fear as well as the excitement that comes with it. Embracing both the former and the latter.
In a similar way, the way the future me looks at the naïve me of today helps me find the elusive confidence I need when I’m in doubt. Would future me look at today me and shake his head in disappointment or pride? What would he tell me to do if he sees I’m struggling? And when I myself cannot manifest the courage to take a step forward, my wiser and more resilient self will manifest the destiny I am meant to walk.
As Suleika Jaouad, author of the memoir Between Two Kingdoms, once said, “[The] act of writing a future dream in the present tense has really kind of helped assuage that fear.”
So ask yourself, What would the Future You say about the You that sits before me today?
I imagine even if you don’t find powerful answers, you’ll find powerful questions that will serve as guiding principles in your own life.
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For today’s blogpost I’m going to try something new. It was requested by a reader of this blog, which for anonymity’s sake, I’ll call P. For those who live a busy life, prefer audio over text, or just find my font choice appalling, I thought I’d record myself reading the below text. Think of it like the audiobook version of this essay.
If you love or hate this format, I’d love to hear what you think. Feel free to comment below, or DM me across any of my channels. Any and all feedback welcome with open arms.
Over the years, I’ve used many different versions of the question: What would you do if you knew you would fail? Or, What would you do regardless of the outcome of the endeavor? And as long as the reason for doing so contains any combination of:
Skill acquisition
Invaluable experience
Or relationship/friendship that I value more than the project itself
… it’s a “Yes” for me. The “Yes” becomes an exploration of depth. An optimization strategy for my strengths. My superpowers. It’s something I learned from quite a few of my mentors over the years – both in an official and unofficial capacity.
Subsequently, I’ve had this belief for a long time, which will probably cause some uproar somewhere, that we shouldn’t optimize our life around reducing our weaknesses. But rather, focus our time on maximizing our strengths. That doesn’t mean we shouldn’t ever work to ameliorate our incompetencies. But:
Just enough that we meaningfully reduce our risk of ruin. Any more, there are diminishing returns over time. Forgiving my esoteric economic jargon, we should only work on our weaknesses so that we don’t lose our ability to survive. For example, if you don’t know how to cook, you shouldn’t aim to be the best Michelin-starred chef in the world, but just enough so that you don’t starve to death. Assuming your goal in life isn’t in the culinary world.
Mitigate our weaknesses that are the most adjacent to our core strengths. For instance, in my opinion, one of my greatest relative strengths is my ability to ask questions. I am by no means the best, but compared to the rest of my skills, this is one I find myself shining in a bit more than my peers. Which effectively meant I was always interested in what others were up to and how they thought. A mentor figure told me years ago that it didn’t matter how interested I was in others, no one had a reason to be interested in me. Which meant that one of my greatest and most adjacent weaknesses was to be interesting.
People who have superpowers often carry super-weaknesses. The greater their superpower, usually the greater their weakness. Humans aren’t great multitaskers. We were never designed to be. If you’re saying yes to one thing, you’re saying no to a hundred other things. Are you willing to shoulder that opportunity cost? Sometimes you are, but be very deliberate about it.
Fairly recently, I was presenting to an amazing cast of board members in a board meeting. There was a general consensus around the fact that we lacked focus as an organization, yet we were sitting on a wealth of talent. To which, one of our board members redirected us to Steve Jobs’ infamous speech when we returned to Apple in 1997. One line in particular stood out to me: “Apple is executing wonderfully on many of the wrong things.“
He follows up to say: “The ability of the organization to execute is really high though. I mean, I’ve met some extraordinary people at Apple. There’s a lot of great people at Apple. They’re doing some of the wrong things because the plan has been wrong.”
Taking a step back, as humans, as working professionals, as entrepreneurs in each and every one of our own rights, we often “execute wonderfully on many of the wrong things.” Often times, that’s on our own weaknesses, rather than our strengths.
Living in a simulation
Imagine that we live in a simulation – an MMORPG. Or, massively multiplayer online role-playing game. We start off with a finite number of stat points. The starting number of stat points varies from person to person, depending on your socio-economic class and your given genetic code. You can allocate those stat points however you want.
You can spread them all out evenly, where you’ll never have any true weakness, but neither any true strength. You’ve hedged your risk of ruin. It’s going to be really hard for you to lose, but you can never really win.
On the flip side of the token, you can minmax your build, using gaming terminology. Double down on a stat, to achieve the equivalent of a superpower, compared to your peers. But often times, if you are maximizing on a superpower, you’ve minimized your proficiency in another area. Luckily, as in any game, and as in reality, you can pick up tools and make friendships along the way that will supplement your weaknesses with their strengths.
Of course, as all analogies go, there are exceptions. But as far as I know, there are far fewer exceptions than those that fit into this analogy. And, technically, our ability to level up is infinite. The only upper limit is that, like everyone else, we have 24 hours in a day and a finite number of years to live.
So, where am I going with this?
Super-tools for (super)weaknesses
What do you not want or don’t care to have a superpower in? For the skills and tasks you use everyday, but don’t care to be the best in the world for, leverage software and tools to automate your work, so you only need to spend the minimal amount of time or energy to make sure it doesn’t become a stressor for your day. In the above gaming analogy, you use items to compensate for specific stat deficiencies. The more efficient the “item”/tool, the less energy you need to expend to make up for a super-weakness.
Here are the tools I use to supercharge my day, so I can spend more time enhancing my superpowers and less time mitigating my super-weaknesses.
Descript
Descript makes me feel like a god. As much as I love Adobe Premiere Pro, it had an incredibly high learning curve. But once you got it, they have some of the most robust tools on the market. On Descript, I love how I can edit an audio or video clip just by deleting words in the transcript. And if I mess up, and I do quite a bit, I can always voiceover in the editing process to make myself sound smarter than I actually am. Even better, I can drag and drop music, video and sound effects. If you’re listening to the audio version of this essay, you might have noticed I don’t have any of the afore-mentioned effects. The goal here was just to get you my thoughts as quickly as possible, without trapping myself in audio perfectionism.
If the Adobe Creative Suite is the endgame, Descript is the early game. And it helps you ace it remarkably well.
Notion
Notion is a dark horse (for me). I’ve seen startup data rooms, personal blogs, internal wikis, and even VC investment theses and fund strategies being produced on Notion. It always seemed like a nice-to-have. In all fairness, I didn’t give it the benefit of the doubt it deserved until late last year. Its greatest ability isn’t the ability to create a robust website or the prettiest blog. Its greatest ability is that it gets people to put ideas and thoughts on paper as quickly as possible. The barrier to entry is so low that its greatest competitors are note-taking apps, like Evernote or Google Keep, for early users. Then, you can go from notes to fully functional site in minutes.
And ever since, I’ve been a geek over it. There’s this great thread on Twitter by @empirepowder about all the applications you can build using Notion extremely quickly – from creating a blog from scratch to publishing a course to tracking analytics on your page to the ultimate tweet tracking tool.
For many of us, the hardest part about doing anything is starting. Notion solves that.
Undock
Take scheduling as another example. I know very few people, if at all, who want to be the best scheduler in the world. I know I don’t. But I find myself spending an undeserving amount of time trying to schedule meetings, rather than actually having meetings or being productive. Enter Undock. “The fastest way to find time to meet with anyone.” That’s from their website. And it’s true. When I’m in my Gmail scheduling calls/meetings with founders or investors, I never leave my email tab nor do I ever touch my mouse. No matter how many people are on the email thread, I can find time for a meeting, on average, in two seconds. That’s no joke. I timed myself.
Meetings are about communication, connection and collaboration. But maybe you’re just exhausted from scheduling them. Look, Undock is actually not “just another scheduling app”. We’re a super calendar and we come in peace.
Having and empowering others to have superpowers is literally in their DNA.
Superhuman
I’ve heard many great things about Superhuman, and about a quarter as many bad things about the platform. Superhuman’s claim to fame is being able to get you to inbox zero via one of the most seamless and fastest email experiences ever – through shortcut keys, follow-up reminders, and social media insights just to name a few. Their user interface makes it incredibly easy to respond from one email to the next, even when you’re offline. They have this 100ms rule, where every interaction should be faster than 100ms to make communication feel instantaneous. And they do deliver.
Many of its customers include investors and founders. Busy people who have more unread emails in their inbox than they care to count. Most of the bad reviews I hear from friends and colleagues are that $30/month is just too expensive.
There are many ways to look at the $30 price tag. It’s $12 more than Netflix’s premium plan, and Netflix serves you new content you might not have access to otherwise. Superhuman serves you the same content that would have been yours anyway, just in a new light. On the flip side, $30/month is $1/day. Less than a cup of coffee a day, assuming you buy your coffee every day. But even if you only bought $3 coffee twice a week, $30/month would still be cheaper.
Or in a different lens, Superhuman’s core audience – founders, investors, busy people who have hundreds of emails a week, if not a day – their time is worth at or more than $30/hour. So, if on a 160-work month, Superhuman collectively saves their customers more than an hour of time every month, then it’s worth it to them.
The way I look at it, it’s a bargain. But I don’t use it. Why? It’s not because it’s too expensive. Neither because I don’t have enough emails to go through. But rather, I happened to optimize my email workflow before I even heard of Superhuman. I’ll save that topic for a later blogpost. But if you don’t have a way to get to inbox zero (unless you don’t care. I have a number of friends who have tens of thousands of unread in their inbox. That scares me)… but if you do care about the piling mound of emails, Superhuman’s really got it in the bag.
In closing
And maybe this post might serve helpful in reframing on how you can live your most optimal life. Supercharge your strengths. And find the best tools and mental models you can to protect your downside. It’s okay if you’re not the best at the latter; you don’t have to be.
I mentioned a few of the tools I use, but your mileage may and probably should vary.
While there are tools out there that supercharge your ability to execute and perform, equally so, you’ll find there are amazing people out there that complement your weaknesses. Friends, colleagues, co-founders, life partners. In the words of Steve Jobs, find and meet “extraordinary people.” To do so, as my mentor told me, you’ll have to be interested and interesting.
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I was reading Sammy Abdullah of Blossom Street Ventures‘ Medium post not too long ago about the value of auto-price increases in a context I’ve never really thought about. Quoting one of his portfolio companies’ founders:
“We started including auto-price increases in our renewals at the start of this year and it’s been surprisingly effective. Our starting point is 10% and we get it more often than not; some customers negotiate us down to the 3–5% range.
“The automatic price increases are a beautiful thing because they give us leverage:
we can trade an automatic price increase for an earlier renewal, longer contract period, or upselling to more features; and
when we do waive price increases, the customer walks away satisfied. They feel like they’re winning.”
It’s a great way to win on net retention. But as I’ve written about before, the net retention equation is comprised of the upgrades, downgrades, and churn variables.
Or convert more users into customers, if you’re running a freemium model
Reduce the number of customers downgrading to lower tiers
Reduce churn – customers leaving your platform
Some permutation of the above variables
Leveling up upgrades
Shivani Berry, founder of Ascend’s Leadership Program, once wrote: “Buy-in is the result of showing your team why your idea achieves their goals.” In a similar sense, buy-in is the result of showing your customers why your product achieves their goals. The best thing is that their goals will change over time. As so, your product must contain increasingly more value to your customers as they level up in their lifecycle. As they grow, you have product offerings that grow with their needs.
Take, for example, one of my favorite startups these days, Pulley, a cap table management tool for startups. Don’t worry, this isn’t a sponsored blogpost. Although it’d be nice if it was. I have no chips in the bag; I just like them. They have three tiers of pricing. The lowest for startups with 25 stakeholders. The middle for startups with 40. And the highest is for larger businesses.
Why 25? The average seed-stage startup has about 25 stakeholders. Subsequently, top of mind for them is what SAFEs and convertible notes look like on their cap table and how to structure early equity pools.
As a startup levels up to 40 stakeholders, they’re probably jumping into their first priced round. As such, they’ll need a 409A valuation to appraise their fair market value, as well as finally putting together their first official board.
Every time founders raise another round of funding, the more complicated their cap table becomes. The more they need Pulley’s software. And it so happens, the less price sensitive they become. For Pulley, that means they can charge more as their customers have greater purchasing power.
You also always want an enterprise pricing tier, where pricing is custom. Don’t be afraid to charge more. As I mentioned in a previous essay, when Intercom was only charging IBM $49, an IBM exec once told the Intercom team, “You know, I go on a coffee run for the team that costs a lot more than your product. That’s why we’re wary of investing too much more in you. We just don’t see how you’re going to survive.” If it helps as a reference point, the median ACV (annual contract value) for public SaaS companies is $27,000.
Do note that the more you charge, the longer the sales cycle will be. For ACVs over $20K, expect 4-6 months of a sales cycle. For contracts over $100K, expect 6-9 months. Of course, the contrapositive would be that the lower the price point, the easier and faster it takes to make a decision.
Reducing downgrades and churn
I’ve been in love with Clayton Christensen’s “jobs-to-be-done” (JTBD) framework ever since I learned of it a few years ago. At the end of the day, you’re delivering value. Value in the form of doing a job. As Christensen says, “when we buy a product, we essentially ‘hire’ it to help us do a job. If it does the job well, the next time we’re confronted with the same job, we tend to hire that product again. And if it does a crummy job, we ‘fire’ it and look for an alternative.”
The better it can do the job your customer needs to get done, the more you can optimize for the variables in the net retention equation. Sunita Mohanty, Product Lead at Facebook, shared an amazing JTBD framework they use back at Facebook and Instagram:
When I… (context) But… (barrier) Help me… (goal) So I… (outcome)
Here’s another way to look at it:
What features should we have that would make our product great?
What features should this product have that would make it a no-brainer purchase for our customers?
The “no-brainer” part especially matters. And to be a “no-brainer”, you have to deliver the best-in-class. Your features have to solve a fundamental job that your customer is trying to solve. The difference between a “great product” and a “no-brainer” is the difference between a 5 out of 5-star rating and a 6-star out of a 5-star rating. Effectively, the outcome in Facebook’s JTBD framework exceeds the goal, which makes the barrier irrelevant. As David Rubin, CMO of The New York Times and former Head of Global Brand at Pinterest once said: “Your service shouldn’t lead with ‘saving money’. You must create an offering that is so compelling, it stands by itself in the consumer’s mind.”
In closing
At the end of the day, in the words of Alex Rampell, building a startup is “a race where the startup is trying to get distribution before the incumbent gets innovation.”
You’re in a race against time. You’re trying to reach critical mass and growth before your incumbents realize your space is a money-making machine. And growth comes in two parts: acquisition and retention. While many founders seemed to have over-indexed on acquisition over the last couple of years, the pandemic has reawakened many that retention is often times much more difficult to attain than acquisition. While it may not be true for every type of business, hopefully, the above is another tool in your toolkit.
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They were part of the defining score of years that brought the sport into the limelight. To most, most of the above names carry little gravity, outside of Phelps. But to me, they were the names that had me huddled around the TV. Watching the prelims. The semis. And of course the finals. They were the names that inspired me to be better.
As Ervin said, “We are the oldest of the fastest and the fastest of the oldest. We are men between worlds.”
But as they came back for one last curtain call this Olympic Trials, I couldn’t help but recall their influence on me in some of my most formative years. Whether I need that extra push for the most challenging project in my life to date or that shoulder to lean on when I am at my worst, there’s one race I cannot help but think about.
Just like when a Yahoo! exec told the Reddit co-founders that they were a “rounding error” and the team subsequently decided to frame it on their office wall as motivation, in 2008, the US Olympic 4×100 freestyle relay team faced a similar dilemma. Despite having Phelps on the relay team, they weren’t the crowd favorites. The French were. They – the American team – were the underdogs.
In fact, that 2008, French team boasted some of the fastest sprinters in the history of the sport. Alain Bernard who had just won his gold in the 100 meter freestyle. And Amaury Leveaux who had taken the silver in the 50 meter freestyle. And besides Lezak who tied for bronze in the 100 meter freestyle, none of the others on the US team had medaled for a short-distance freestyle event that Olympics.
Pound for pound, the US relay team had to deliver not only their best, but beat their best. To have a chance at beating the French team. So for motivation, they read Bernard’s comment in the papers over and over. “The Americans? We’re going to smash them. That’s what we came here for.”
Phelps leads the race, giving his team a slight lead over France. Weber-Gale holds that lead for the Americans. Jones, the slowest and the third leg of the team, yet still punching every inch of his worth, gives the lead back to France. And Bernard, the world champion in the 100 free, against Lezak for the US, gets a strong lead for a race and a length he is already the best in the world at. Lezak trails behind by over half a body length at the flip. 50% done of the last leg of the race.
I remember sitting in front of the television screen, screaming and hoping my voice would reach the Water Cube in Beijing. “C’mon… c’mon! C’mon!!” Lezak, at 32, one of the oldest competitors in the pool that year, pulled together what could only be described as sheer willpower. Those last 50 meters… seemed to have been the longest 23 seconds of my life. A breath for every second that passed. A breath for every second Lezak pulled closer to Bernard. And in the last ten seconds, minus the sound of the TV, the room was silent. As some people might say, you could hear the sound of a pin drop. It did. With a margin of eight hundredths of a second.
One of the tightest and most inspiring races in all of history. If you ask me, the greatest. And the race I watch time and time again when I am at my worst.
You have to see it for yourself to really believe the excitement.
#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!
I’ve alluded to my ability to say “No” in many previous blogposts, like this one. But as this concept has crawled around in my subconscious for as long as it did, I believe it now deserves a blogpost in its own right.
As a kid, I learned from my parents to say “No” to strangers. The “uncle” who’d say my dad told him to pick me up. Or the “auntie” who’d offer a lollipop to me and ask me where my parents were. To the point it became muscle memory to say “No” to gifts, as well as compliments, even from friends and family. Over time, that notion became more prevalent as it infected other parts of my life.
I learned to discriminate my time before I had a chance to fill in my calendar. Even worse, when I ever hesitated, it became a no-brainer to say no. And subsequently, I missed out on more opportunities I can count. “Whenever there is any doubt, there is no doubt.” It’s a line from De Niro’s character in the 1998 movie Ronin. In essence, if you ever hesitate, some part of your body is telling you “No” while other parts are telling you “Yes”. And there’s a good chance that that “No” is right. Or if you do say “Yes” and things go awry, the voice in the back of your head that said “No” will only exacerbate into full denial. And you may end up hating the reasons you said “Yes” to before.
But it wasn’t from that movie, when that line became immortalized in my mind. I heard it uttered by Tim Ferriss on one of his regular episodes. Or maybe it was from one of his books, like Tribe of Mentors. But I wouldn’t sweat the details.
The thing is, he’s completely right. Both De Niro’s character, Sam. And Tim. But I learned there’s a caveat. Earlier on in your life and career, it’s about taking in more experience since your 24-hour day has yet to fill up. You have to say “Yes” before you know how to say “No”. I overvalued on advice and undervalued experience. Both Sam and Tim were right. But they were right in their own lives, or rather they were right when I would one day have enough things to say “No” to. All advice is, after all, autobiographical.
100 minus your age
I don’t remember where, but I once heard this amazing heuristic for picking up new books. 100 pages minus your age. It equals the number of pages you should read before you decide whether to put down the book or not. The younger you are, the more pages you should read to understand if this book is worth your time or not. Why? Because you simply don’t have large enough of a sample size to recognize the patterns of good versus not-so-good literature. As you grow older, the fewer pages you need to read before you decide if the book is worth your time. Over time, you have a better grasp as to what quality looks like.
A similar notion seems to apply to your life. 100 points minus your age. That’s the margin of error you have when making decisions. The younger you are, the more prone you are to making wild mistakes. The older and more experienced you get, the better you can tell good from bad decisions.
In closing
I’m reminded of something Henry Ford once said. “Whether you think you can, or you think you can’t – you’re right.”
I lost out on many opportunities. The thing is no opportunity will ever be perfect. But in thinking each opportunity I take had to be perfect, I thought I couldn’t – shouldn’t – take it. But frankly, I just wouldn’t. I became a professional brat. There will always be something or somethings that just don’t make the opportunity click. But in saying “No”, you are saying “Yes” to the status quo. That’s something I have to remember.
As Eric Schmidt of Google fame once said, “Yes is how you get your first job, and your next job, and your spouse, and even your kids. Even if it’s a bit edgy, a bit out of your comfort zone, saying yes means that you will do something new, meet someone new, and make a difference. Yes lets you stand out in a crowd, be the optimist, see the glass full, be the one everyone comes to. Yes is what keeps us all young.”
#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!
As I am co-leading a VC fellowship with DECODE (and here’s another shameless plug), a few fellows asked me if I had a repository of questions to ask founders. Unfortunately, I didn’t. But it got me thinking.
There’s a certain element of “Gotcha!” when an investor asks a founder a question they don’t expect. A question out of left field that tests how well the founders know their product, team or market. In a way, that’s the sadist inside of me. But it’s not my job, nor the job of any investor, to force founders to stumble. It’s my job to help founders change the world for the better. By reducing friction and barriers to entry where I can, but still preparing them as best as I can for the challenges to come.
I’m going to spare you the usual questions you can find via a quick Google search, like:
What is your product? And who is your target audience?
How big is your market? What is your CAGR?
What is your traction so far?
How are you making money? What is your revenue model?
And many more where those come from.
Below are the nine questions I find the most insightful answers to. As well as my rationale behind each. Some are tried and true. Others reframe the perspective, but better help me reach a conclusion. I do want to note that the below questions are described in compartmentalized incidents, so your mileage may vary.
Here’s to forcing myself into obsolescence, but hopefully, empowering the founders reading this humble blog of mine to go further and faster.
The questions
I categorize each of the below questions into three categories:
The market (Why Now)
The product (Why This)
And, the team (Why You)
Together, they form my NTY thesis. The three letters ordered in such a way that it helps me recall my own thesis, in an unfortunate case of Alzheimer’s.
Why Now
What are your competitors doing right?
This is the lesser-known cousin of “What are your product’s differentiators?” and “Why and how do you offer a better solution than your competitors?”. Founders are usually prepared to answer both of the above questions. I love this question because it tests for market awareness. Too often are founders trapped in the narratives they create from their reality distortion fields. If you really understand your market, you’ll know where your weaknesses are, as well as where your competitors’ strengths are.
There have been a few times I’ve asked this question to founders, and they’d have an “A-ha!” moment when replying. “My competitors are killing it in X and Y-… Oh wait, Y is our value proposition. Maybe I should be prioritizing our company’s resources for Z.”
Why is now the perfect time for your product to enter the market?
As great as some ideas are, if the market isn’t ripe for disruption, there’s really no business to be made here… at least, not yet. What are the underlying political, technological, socio-economical trends that can catapult this idea into mass adoption?
For Uber, it was the smartphone and GPS. For WordPress and Squarespace, it was the dotcom boom. And, for Shopify, it was the gig economy. For many others, it could be user habits coming out of this pandemic that may have started during this black swan event, but will only proliferate in the future. As Winston Churchill once said, “Never let a good crisis go to waste.”
A great way to show this is with numbers. Especially your own product’s adoption and retention metrics. Numbers don’t lie.
What did your customers do/use before your product?
What are the incumbent solutions? Have those solutions become habitual practices already? How much time did/do they spend on such problems? What are your incumbents’ NPS scores? In answering the above questions, you’re measuring indirectly how willing they are to pay for such a product. If at all. Is it a need or a nice-to-have? A 10x better solution on a hypothetical problem won’t motivate anyone to pay for it. A 10x on an existing solution means there’s money to be made.
Before we can paint the picture of a Hawaiian paradise, there must have been several formative volcanic eruptions. It’s rare for companies to create new habits where there weren’t any before, or at least a breadcrumb trail that might lead to “new” habits. As Mark Twain says, “History doesn’t repeat itself, but it often rhymes.”
Why This
What does product-market fit look like to you?
Most founders I talk to are pre-product-market fit (PMF). The funny thing about PMF is that when you don’t have it, you know. People aren’t sticking around, and retention falls. Deals fall through. You feel you’re constantly trying to force the product into your users’ hands. It feels as if you’re the only person/team in the world who believes in your vision.
On the flip side, when you do have PMF, you also know it. Users are downloading your product left and right. People can’t stop using and talking about you. Reporters are calling in. Bigger players want to acquire you. The market pulls you. As Marc Andreessen, the namesake for a16z, wrote, “the market pulls product out of the startup.”
The problem is it’s often hard to define that cliff when pre- becomes post-PMF. While PMF is an art, it is also a science. Through this question, I try to figure out what metrics they are using to track their growth, and inevitably what could be the pull that draws customers in. What metric(s) are you optimizing for? I wouldn’t go for anything more than 2-3 metrics. If you’re focusing on everything, you’re focusing on nothing. And of these 1-3 metrics, what benchmark are you looking at that will illustrate PMF to you?
For example, Rahul Vohra of Superhuman defines PMF with a fresh take on the NPS score, which he borrows from Sean Ellis. In feedback forms, his team asks: “How would you feel if you could no longer use the product?” Users would have three choices: “very disappointed”, “somewhat disappointed”, and “not disappointed”. If 40% or more of the users said “very disappointed”, then you’ve got your PMF.
Founders don’t have to be 100% accurate in their forecasts. But you have to be able to explain why and how you are measuring these metrics. As well as how fluctuations in these metrics describe user habits. If founders are starting from first principles and measuring their value metric(s), they’ll have their priorities down for execution. Can you connect quantitative and qualitative data to tell a compelling narrative? How does your ability to recognize patterns rank against the best founders I’ve met?
If in 18 months, this product fails. What is the most likely reason why?
This isn’t exactly an original one. I don’t remember exactly where I stumbled across this question, but I remember it clicking right away. There are a million and one risks in starting a business. But as a founder, your greatest weakness is your distraction – a line in which the attribution goes to Tim Ferriss. Knowing how to prioritize your time and your resources is one of the greatest superpowers you can have. Not all risks are made equal.
As Alex Soktold me a while back, “You can’t win in the first quarter, but you can lose in the first quarter.” The inability to prioritize has been and will continue to be one of the key reasons a startup folds. Sometimes, I also walk down the second and third most likely reason as well, just to build some context and see if there are direct parallels as to what the potential investment will be used for.
On the flip side, one of my favorite follow-ups is: If in 18 months, this product wildly succeeds. What were its greatest contributing factors?
Similar to the former assessing the biggest threats to the business, the latter assesses the greatest strengths and opportunities of this business. Is there something here that I missed from just reading the pitch deck?
What has been some of the customer feedback? And when did you last iterate on them?
I’m zeroing in on two world-class traits:
Open-mindedness and a willingness to iterate based on your market’s feedback. As I mentioned earlier with Marc Andreessen’s line, “the market pulls product out of the startup.” Your product is rarely ever perfect from the get-go, but is an evolving beast that becomes more robust the better you can address your customer’s needs.
Product velocity. How fast are your iteration cycles? The shorter and faster the feedback loop the better. One of the greatest strengths to any startup is its speed. Your incumbents are juggernauts. They’ll need a massive push for them to even get the ball rolling. And almost all will be quite risk-averse. They won’t jump until they see where they can land. Use that to your advantage. Can you reach critical mass and product love before your incumbents double down with their seemingly endless supply of resources?
Why You
What do you know that everyone else doesn’t know, is underestimating, or is overlooking?
Are you a critical thinker? Do you have contrarian viewpoints that make sense? Here, I’m betting on the non-consensus – the non-obvious. While it’s usually too early to tell if it’s right or not, I love founders who break down how they arrived at that conclusion. But if it’s already commonly accepted wisdom, while they may be right, it may be too late to make a meaningful financial return from that insight.
But if you do have something contrarian, how did you learn that? I’m not looking for X years of experience, while that would be nice, but not necessary. What I’m looking for is how deep founders have gone into the idea maze and what goodies they’ve emerged with.
Why did you start this business?
Here, unsurprisingly, I’m looking for two traits:
Your motivation. I’m measuring not just for passion, but for obsession and the likelihood of long-term grit. In other words, if there is founder-market fit. Do you have a chip on your shoulder? What are you trying to prove? And to whom? Do you have any regrets that you’re looking to undo?
Most people underestimate how bad it’s going to get, while overestimating the upside. The latter is fine since you are manifesting the upside that the wider population does not see yet. But when the going gets tough, you need something to that’ll still give you a line of sight to the light at the end of the tunnel. Selfless motivations keep you going on your best days. Selfish motivations keep you going on your worst days.
Your ability to tell stories. Before I even attempt to be sold by your product or your market, I want to be sold on you. I want to be your biggest champion, but I need a reason to believe in the product of you. You are the product I’m investing in. You’re constantly going to be selling – to customers, to potential hires, and to investors. As the leader of a business, you’re going to be the first and most important salesperson of the business.
What do you and your co-founders fundamentally disagree on?
No matter how similar you and your co-founders are, you all aren’t the same person. While many of your priorities will align, not all will. My greatest fear is when founders say they’ve never disagreed (because they agree on everything). To me, that sounds like a fragile relationship. Or a ticking time bomb. You might not have disagreed yet, but having a mental calculus of how you’ll reach a conclusion is important for your sanity, as well as the that of your team members. Do you default on the pecking order? Does the largest stakeholder in the project get the final say after listening to everyone’s thoughts?
Co-founder and CEO of Twilio, Jeff Lawson, once said: “If your exec team isn’t arguing, you’re not prioritizing.”
I find First Round’s recent interview with Dennis Yu, Chime’s VP of Program Management, useful. While his advice centers around high-impact managers, it’s equally as prescient for founding teams. Provide an onboarding guide to your co-founders as to what kind of person are you, as well as what kind of manager/leader you are. What does your work style look like? What motivates you? As well as, what are your values and expectations for the company? What feedback are you working through right now?
In closing
Whether you’re a founder or investor, I hope these questions and their respective rationale serve as insightful for you as they did for me. Godspeed!
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I have this conception of a personal Hall of Fame. For every piece of content, individual, and or experience in my life that has drastically changed the way I live or the way I think about life. Upon entrance, I find myself facing three large corridors – each adorned with text in Garamond font, framed in the corpse of a giant oak tree. In the corridor to the left, it’s the “Content Hall”. Arguably, the most competitive of the three halls to get into.
I only meet so many individuals in my life. I would say somewhere on the magnitude of tens of thousands. To pick tens of individuals among 10,000 is a 0.1-0.2% chance of induction.
The same is true for experiences. Excluding my daily habits of sleeping, eating, and others that have become second nature, there are very few extraordinary experiences among the ordinary. And in pursuing something extraordinary over a prolonged duration, that something extraordinary becomes ordinary to you. So, over time, you end up regressing into a step-wise function of finding the extraordinary in the extraordinary. To choose from a select few of these extraordinary in the extraordinary experiences at various learning curve spurts leaves an even smaller sample size.
Yet the same can’t be said for content. We consume a plethora of content on a daily basis. From obvious content drops, like YouTube, books, shows, and podcasts, to the non-obvious, such as emails, conversations, street signs, and opportunities that make you pause in the buzz of daily life. With tons of constant inputs from multi-directional sources, picking the handful that has altered your life’s course has a far lower acceptance rate than being struck by lightning.
For me, one of the greatest pieces that exists in my “Content Hall” is The Tail End by Tim Urban. There are a multitude of great anecdotes in it, but my favorite of which is, by the time we turn 18 years old, we’d already have spent at least 90% of our time with our parents.
Presidents
Say I live to 90 years old. In my lifetime, I get to see 22 US presidential terms. 22 presidents max, but many presidents hold office for two terms rather than just one term. There’ve been 46 presidents in the history of the United States so far. 21 of which served two terms. For ease of calculation, there’s about a 50% chance that any president will hold office for two terms. That’s 16 presidents, give or take, throughout my entire life. I’ve lived through Bill Clinton, George W. Bush, Barack Obama, Donald Trump, and now Joe Biden. That’s 5, and only 11 more to go. Of course there’s the chance of early impeachment. But let’s assume everyone serves their full term.
I’m 25 now. So, I’ve already seen almost a third of the presidents I will see in my lifetime.
Summer vacations
If I live till 90, I have another 65 summers to go. 65 summer vacations left.
If I settle down by 35, I have 10 more summer vacations left – entirely free from constraints and in my prime. I can go skydiving and play extreme sports, without having to worry about seeing the chiropractor. And I imagine, like many others out there, I have more than 10 summer vacation spots I want to hit, excluding the ones I want to have repeat visits to. I already wish I had more time.
Times I’m wrong
In preparing for this essay, for the past week, I tracked the number of times I realized I was wrong. Racking the numbers up each day for seven days. From getting the weather wrong to forgetting what I thought we had for leftovers to being one digit off on my recollection of industry metrics during a meeting, I make on average two small mistakes a day. Extrapolating that to the rest of my life, I have almost 47,500 more small mistakes left to make. I’ve never felt more human than I do now.
Of course, the above number doesn’t include all the times I’ve realized I was wrong after the fact, which I imagine accounts for a mountain of imperfections in its own right. Enough to rival the Great Pacific Garbage Patch.
Idea journals
Many of you reading this blog are no stranger to my idea journals. I go through a journal every four months. I have almost 200 more idea journals to go through, assuming I keep at the pace I’m going at now. 195, to be exact. Oh wow, I really need to invest in some shelf space in my future homes. Enough for over 20,000 pages and all hardcover leather-bound journals.
Breakdowns
Each time I conquer a mental breakdown I think I’d be more resilient. In many ways, I am right. In many more, I am still unprepared for what is to come. Just as the sun rises, I too will cognitively readjust to my stress levels. While I wouldn’t describe my breakdowns to be on regular intervals, on average, it seems to happen once every five years. At least a major one, discounting all the smaller frustrating moments I come across. That’s 18 total, and 13 more mental shifts I won’t be ready for no matter how much I prepare.
In closing
All the above calculations were in the scope of 90 years old. But the awesome part is if I live past 90, every day will be icing on the cake. It’ll be better bang for my buck!
The point of this mental shift isn’t to be 100% accurate (’cause I know I’ve made quite a few generalizations). But rather reframe how we choose to live our lives.
In comparison with the hundreds of thousands of years the human species has lived, we are mere century inhabitants. And in the whole history of Earth, if we were to count on a 24-hour clock where the formation of Earth began at time 00:00:00, humans have lived just over a minute. We have short lives. Maybe that’ll change some time in our lifetime, with technology, CRISPR, or some sci-fi derivation.
But that doesn’t mean we can’t live fulfilling lives. Or as Garry Tanputs it, most people are “short term optimists” and “long term pessimists” and end up picking smaller problems to tackle. Rather, we gotta be “short term pessimists” and “long term optimists.” We have short lives, but let’s live a life where our impact lasts beyond our physical lifespan.
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost). Who knows? The possibilities are endless.
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In the first decade of my life, my parents used to buy me different kinds of puzzles – from the Rubik’s cube to beautifully intricate LEGO sets to Luban locks. One of my favorites has always been these thousand-piece puzzles. Every time I poured those pieces out of the box, they scattered across our carpet like tiny ants scrambling to find meaning. I loved putting the puzzle together having only seen the completed image once – when I opened the box. That probably, at most, left a three-second impression in my mind. How awesome would photographic memory be. But alas, it wasn’t something I’d been blessed with. I only found out years later from friends that it wasn’t normal. That said, I imagine I took much longer than most people to piece together the whole puzzle.
Fresh out of the box, I start off knolling the various incongruous shapes. Like most others, I’m looking for similar designs, colors, lines, images – anything. Trying to make sense of disparate pieces. Frankly, I was drawing parallels wherever and whenever I found them. A more mature me would call it – pattern recognition.
As I progress, I spy colonies of color form in different areas on the living room floor. And therefore, try to see if any colonies, together, would tell a more robust, vibrant story. Sometimes I was right. Sometimes I was wrong.
As I near the end of the puzzle, I see everything come together. I’m not gonna lie. It’s extremely gratifying to see the rough picture in my head come to life. Often times, the final image has minor deviations from the loosely-defined vision I had when I started.
You probably caught on
You’re smart, and you probably guessed what I was trying to get at before you even finished reading my anecdote. And you’re right. In many ways, this puzzle journey is very similar to building a company. You start off with an idea, constructed upon anecdotal patterns you’ve seen in the world you know. And as you build the idea and talk to customers – other nearby pattern aggregations – you start to piece together a larger and more concrete goal. By the time you reach scale, you’re filling in the little details – the extra puzzle pieces – you missed when focusing on the more holistic vision. The little details of debugging, solving edge cases, and improving the user experience.
Listen to the silence
The initial idea comes from recognizing the patterns around you. Both what is being said, and what isn’t. Both what is there and what could be there.
One of my favorite stories on pattern recognition is about Abraham Wald, a Hungarian-Jewish mathematician and statistician, who’s credited with saving the lives of numerous pilots and airmen during WWII. Tasked with aircraft armor repair, Wald, then a faculty at Columbia University, was given a number of data points on bullet holes in the fighter planes that returned to base. Most were around the fuselage and a few around the motors.
As one would expect, the military anticipated to double down armor around areas with the most damage – the fuselage. But Wald took a different angle. Reinforce the plate metal around the motors, rather than the fuselage. Because the planes that didn’t make it back most likely had bullet holes where the planes that did make it back didn’t.
Listen to the sound
Sometimes you’re right. Sometimes you’re wrong. And if you’re wrong, follow the breadcrumbs of your market. Notice what their use cases are and how they’re spending their time. Even better if they’re developing hacks to circumvent the early inefficiencies of your product. What features or problems are getting a lot of attention?
For instance, Stewart Butterfield didn’t start off with the idea for Slack. After selling Flickr to Yahoo! and working at Yahoo! for three years after, he started with Tiny Speck, a gaming startup that raised $17M in venture funding to build Glitch. Unfortunately, it didn’t take off, outside of its cult following. But what did stick was the tool Stewart and his team had been using to chat in real-time with each other. Less than a year after it officially launched, it hit a $1B in valuation. Six years later, it became Salesforce’s biggest acquisitions at over $27B. And history is still being written.
Similarly, Kevin Systrom didn’t start off with Instagram. But rather Burbn – a location-based check-in app. Users would check-in, plan future meetups with friends, share pictures of their meetups, and earn points in the process. Unfortunately, the app was too complicated for the average user to use. After bringing on Mike Kreiger and analyzing how their users were using the app, they realized most of their traffic happened around posting and sharing photos. Scrapping everything else, they focused on their biggest use case – photo-sharing. And well, they were right on the pivot. In 2012, right before Facebook’s IPO, Facebook acquired Instagram for $1B. It was big then, but as we all know now, it’s even bigger now.
Back in 2012, Kevin once said, “It’s about going through false starts… Brbn was a false start. The best companies in the world have all had predecessors. YouTube was a dating site. You always have to evolve into something else.”
In closing
I love people who binge. It’s a sign that they capable of going all in and more on something they’re passionate about. I, myself, have binged time and time again on puzzles, shows, books, passion projects, and more. For Stewart, it was games. For Kevin, it was whiskey and bourbon. On the other hand, for Abraham, I can’t quite say. I have no idea if he was into plate armor or planes, but whether he liked it or not, he probably spent sleepless nights on it.
And in the process of binging, if you keep my mind and my senses open to inspiration, you may uncover some patterns in the mix. ‘Cause if you’re going to notice what’s being said and not said between the lines, you’re going to have to be in deep. Deep enough to take your breath away, but not deep enough to take your sight away.
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Many of my friends are no stranger to the ephemeral nature of my creative outbursts. Some of these ideas are whimsical in nature. Where, from the start, they carried no real weight behind their punch. A deplorable few collected dust in the attic, as a product of giving myself the time to think twice. To second-guess myself. In fact, partly due to being in VC, I became quite proficient at saying “No.” I was so good at saying “No” that I forgot how to say “Yes”. And as I wrote before, the theme of this year is to say “Yes” to more opportunities to experience growing pains. So, when my friend brought up something she used to track things she repeatedly says “Yes”, then “No” to, I was intrigued. She called it her fickle jar. And of course, I had to ask.
Both she and I share common ground. In the sense, that we happen to be promiscuous when it comes to ideas. We mint and host a multitude of ideas. But often don’t give most of our thoughts a double take before we abandon them. They retire from our lips before they have an opportunity to marinate in our minds.
So both of us needed this fickle jar. The fickle jar is a jar chronicling everything you might be fickle on. Soft commitments of “I should do X.” Or “It’d be cool to do Y”. It’s a visualization of the loose promises you make to yourself. Every time you think of a something you want to or should do, write it down. Draw it in its own bubble. Each idea isolated from the next – though some might be related. And each time you follow through and act on the idea, you color your bubble in. When you finish a jar, make another one. Over time, you can visually see what your creativity to commitment ratio is.
Over the next few months to years, I know I’ll accumulate enough fickle jars to have my own fermentation station in my basement. The goal of all of this is to visually track my partiality between creativity and commitment. But moreover, to emphasize intentionality. In the event I propose an idea – which is inevitable – it’s not a fleeting thought. And those of a less ephemeral nature, I take it and give it a go, regardless of the outcome. Hesitation has always been the enemy of my progress. Ideally, over time, I commit to most ideas that spring up. But realistically, I know it isn’t possible. Neither should it be a priority.
Yesterday morning, I was reading First Round’s interview with Irving Fain, co-founder of Bowery Farming, who recently announced their $300M Series C round. While not your first-time founder, having built CrowdTwist (acq. Oracle) and iHeartRadio, with Bowery, he, nevertheless, jumped into an industry he knew little about.
“I could sit on a chair and think my way around this problem for another decade, but when building a company, you never avoid that moment where you have to jump off the cliff. In some respects, what you want to try to make the cliff-to-ground ratio as small as you can. But there is no amount of work and research that avoids the fact that at some point you’re jumping off into the abyss.” So like Irving, I need to have the nerve to jump into the abyss – at least more so than the status quo. I just have to say “yes” to the genre of ideas that have historically left me in decision paralysis.
Fain goes on to say, “Before I started my first company, I spent enormous amounts of time evaluating, evaluating, evaluating, saying no, and evaluating, evaluating, evaluating, and saying no. And in hindsight, I look back and say, ‘Wow, I said no to some great ideas.’ I spent way too much time getting to the wrong answer, arguably.”
I recently realized that some of the biggest risks I ended up taking is spending undue time amidst inaction. The risk is the opportunity cost of the time I could be spending elsewhere. Yet I choose indecision – an infertile stalemate. Crops won’t grow if the soil hasn’t been tilled.
She also noted, “Fickle also rhymes with pickle.”
Ironically, this essay almost became a fickle pickle ’cause I was too lazy to transcribe my fickle jar.
#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!
I was introduced to a founder of an e-commerce marketplace recently trying to figure out what product-market fit looks like. Specifically what might be some early tells of PMF. And I told him, “If your users are sticking around long enough to try to game your system, you have something they want. While it might not be in the most efficient format, you’re close to PMF. Subsequently, solving that frictional point that users are trying to ‘hack’ will delight them.”
Last year, I wrote that one of the tells of a great unicorn idea is frustration with the status quo. And the lagging indicators of frustration are complaints, but even better, “hacks”. Life hacks. Career hacks. Cold email hacks. Any time a forum or community comes together to share best practices is a potential market opportunity. As Jeff Bezos once said, “Your margin is my opportunity.”
Similarly, if some of your users converge around circumventing your platform, they’re hacking their way to find a better solution. But the fact they’re sticking around on your platform means you have something they want. And while it could be more elegant, you’ve solved the rocks of the “rocks, sand, and water” framework. What’s left are the “sand” and the “water”. And they come disguised as a user hack.
Sarah Tavel of Benchmark once wrote: “You must create an offering that is so compelling, it stands by itself in the consumer’s mind.” Solving all the frictional points in the user journey will get you to that compelling offering – a lovable product.
A reader reached out to me last year and said, “Thank you… [But] you have no idea how long I spend reading your blogposts with a dictionary next to me.” While it wasn’t necessarily a hack, to know there was a reader out there willing to weather through my idiosyncratic vocabulary in my earlier essays meant a million to me. But at the same time, it was a sign I was too caught up in my own wordsmithing. So, I dialed it back. While there will still be some esoteric jargon from time to time, I try to make my writing more relatable when editing. And to that reader… if you’re still reading this essay, thank you.
Back in 2007, Marc Andreessenwrote: “The market pulls product out of the startup.” In this case, that pull becomes a race between you and your users’ frustration. Can you release an update that addresses your users’ pain point before they become so frustrated they pack up and go? Either to build their own version or try a competitor’s.
I love Max Nussenbaum of On Deck’s analogy here. “If the market is indeed pulling the product out of you, you sometimes feel less like a creator and more like a mere conduit.” You, as the team behind the product, are a conduit to satisfying your users’ needs. As Mike Maples Jr.says, “Getting storytelling right means the founder is the mentor of the story (ie Yoda), rather than the hero (ie Luke.).” Your customers are the heroes of the story. Of their story. And your story. How they spend their time should offer you brilliant product insights.
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!
