Straight off the bat, you might have realized that the 10th issue of the DGQ series – damn good questions – starts off with a non-question. And it is intentional by design. I often waste a number of calories constructing the perfect question. And in many ways, I get very, very close to what I deem as perfection. Exhibit A, B, and C.
But over the course of constructing the perfect question and its subsequent research, I often uncover the answer I am seeking… before I even ask it to the intended designee. I don’t mean for the odd question here and there amidst spontaneous conversation. But the predestined ones to be asked in:
Fireside chats
Intro conversations
Coffee chats with individuals where I’m punching above my weight class
Podcast interviews
Social experiments
First dates (possibly self-incriminating)
Accompanied by the excuse of creating conversation, I ask it despite the since-acquired knowledge. Sometimes to the wonder and amazement of the recipient, but more often than not to the boredom of myself. While the words that flutter out of my mouth may sound like a question, it ends up merely being a statement rearranged on a NY Times crossword puzzle.
In reframing questions for myself, I realized… If I knew all the answers to the questions I would ask, that’d make for quite a boring life. While boredom only surfaced a minority of the time, it occurred noticeably enough times. If I had a mirror to myself every time I asked a question, I imagine I would find myself asking the ones I have the answers to already with a furrowed brow.
Last year, in the relentless pursuit of being a better host for structured conversations, I over-optimized for shock and delightful surprise. Shock became my unfortunate currency for my personal delight. Rather than enlightenment, education, and inspiration. In the construction of the “perfect question,” while protecting my downside – in terms of embarrassment, I capped my upside.
So, this essay is a reminder to myself. Ask dumb questions. It’s okay. It’s only by reinventing yourself again and again through the ashes of unintentional ignorance can you rise like a phoenix.
I’m reminded of a quote by quite a contrarian philosopher, Karl Popper, but nevertheless quite appropriate here. “Good tests kill flawed theories; we remain alive to guess again.”
If you’re reading this essay, be prepared for a lot more dumb questions from me. Dumb, not garbled. Dumb and simple. I’ll continue to do my homework before conversations. But if I’ve found the answer already, I’m going to keep myself accountable to either find new questions or cancel the meeting. Cheers to the motif of exploration! And I’ll see you where I cannot foresee.
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.
Back in my sophomore year of college, I was running to be the vice president of a business organization. Part of the requirement to run as one was to shadow at least two executives from previous generations who held the same role. Brownie points if you shadowed the broader executive team as well. The goal was to better prepare yourself by increasing the context you had about a new role.
I checked off those boxes with flying colors. In fact I ended up talking to more than 20 other executives and other key campus constituents we would be interfacing with. Along the way, I shared what I would do, not do, and do differently compared to previous roles. I also told them how I would forever change the organization and its impact on campus and students. Frankly, I felt like I was a on a roll. I was on top of the world.
Yet one winter night (it’s always the winter nights that get you), when I was on my haughty high horse, one person stopped me in my tracks. With one simple question. “What is your selfish motivation?”
“I’m going to change…”
“No, David… what is your selfish motivation?“
Flash-forward
Last week, one of my favorite hustlers reached out to me. She was planning to start a newsletter soon and wanted some advice from a fellow writer. After a few exchanges asynchronously, it became apparent that her biggest obstacle was keeping to a schedule. If you’re a frequenter here, you’ll have noticed I’ve already lost all semblance of a schedule other than publishing weekly. Some weeks I publish on Mondays. Others on Tuesdays. Some weeks see two essays. Others only one. But I have yet to lose my streak of publishing weekly. But I digress.
There’s a large graveyard filled with content creators who post ten or less times. Off the cuff, I dare say 90%. Prior to this blog, two of my other blogs were also no stranger to the obituary.
So, I posed the same question that stumped me all those years back. What is your selfish motivation?
What is your selfish motivation?
Most people, especially in the realm of entrepreneurship, job interviews, politics, and PR stunts, share their selfless motivations. Everyone’s a Samaritan. While there is some truth to it, everyone needs a really good selfish motivation.
On your best days, if your project is doing really well and you’re absolutely crushing it, your selfless motivation will be what you tell the latest press release, your cousins over the holidays – the story you pitch to others. The story you also tell yourself to give your job meaning. But on your worst days, when you want to give up, your selfish motivation is what’ll keep you going. When you’re at your worst, you won’t want to care for others. You care about yourself. What’ll keep you sane? If your selfish North Star isn’t strong enough, it’s easy to give up.
You need both. Your selfless motivation will help you reach for the stars. Your selfish motivation will prevent you from hitting rock bottom.
For example, for this blog, my selfless motivations are:
Democratizing access to resources and education to help people move the world’s economy forward,
Empowering founders to not fall through the same potholes I or other founders fell through – to make new mistakes not old, and
Empowering and inspiring others to live more enriching lives.
It’s what I tell others. My lofty goal that’ll make writing this blog meaningful to me.
On the other hand, my selfish motivations are:
I write to think. My thoughts are so much clearer on paper than if I just speak them. If I don’t write things down, I’m a mess.
I forget things easily. Short term memory loss. And my blog is a way for me to catalogue my own learnings.
I feel much more comfortable being vulnerable with strangers than with friends. So my blog helps me relieve much of my stress and anxiety.
I am neither as good as people say I am nor as bad as people say I am. This blog keeps me honest.
In closing
That same winter night was the day of the winter equinox. I don’t mean to dramatize my little anecdote, but I nevertheless I do find it provides a little flavor to the story.
“No, David… what is your selfish motivation?”
“I don’t follow.”
“I ask every officer candidate this question. There will be days that you will hate the job more than you will love it. And I need to know if you have it in you to weather those days.”
I don’t remember what I told him that night. I don’t think it was a particularly honest answer. Or maybe I was honest. But it wasn’t enough. I didn’t get his vote of confidence, but I did enough legwork to get the approval of others.
In the end, I got the position. And he was right. Times got tough. There were days I hated the job. And on those days, in particular, I didn’t do anything remotely close to “changing the organization and its impact on campus.”
#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!
The Japanese art of finding beauty in imperfection. More specifically, the art of mending broken pottery. Kintsugi finds an object’s value and beauty is a result of its imperfections, rather than the lack thereof.
Much like the year prior, and like for most, 2021 was a year of imperfections. What could have gone wrong went wrong. And what could have been weighed heavily on many people’s minds. It’s been a trying year for almost everyone. From Delta to Omicron, from the insurrection in January to military withdrawal from Afghanistan, from forest fires to the increase in crime in the Bay Area. Despite still wrestling with the constraints imposed by the pandemic and the broader socio-political-economic world, 2021 was the worst and best year I could have ever hoped for. The beauty was not that these events happened, but that these events led us to form deeper relationships, greater awareness for macro issues, and a general movement forward to change what hasn’t and will not work in tomorrow’s world. Simply put, I’ve never been more bullish on being human.
This year was the year of saying “Yes.” In contrast to my track record of regressing to “No.” And so far, I’m on a roll. That also means that I’m busier than ever. Nevertheless, because of my intentionality behind finding serendipitous moments in my life, I’ve had the pleasure of finding myself in a constant state of inspiration. To quote one of my good friends, who’ll appear in a blogpost soon enough: “Inspiration is the disciplined pursuit of unrelated [and unexpected] inputs.”
I wrote almost 90,000 words this year, excluding this blogpost, which for better or for worse, means I wrote just enough to fill the average nonfiction book and a half. In terms of the number of blogposts and words I’ve written, I’ve slipped in comparison to last year. Last year, I minted over 100 essays. And this year, I’m 20% shyer in quantity on both fronts. Yet, while recency bias may play a role, I’ve never been prouder of the content I’ve put out. Fundamentally, what I learned is that I have to take longer per blogpost.
My writing journey pre-2021
In 2019 and 2020, I took pride in minting a blogpost in under 24 hours at best. 48 hours at worst. I would start writing each piece during the night, right after my shower. Go to sleep. And finish editing the next morning before publishing.
Under those circumstances, while there were a number of pieces that I am still proud to have written to this date, there were many that would have been orders of magnitude better if I just let it sit for a few days longer. If I just let the content marinate a bit longer.
… In 2021
This year, unintentionally, I did just that. It started with a steep ramp up in my day-to-day schedule, rendering me unable to commit large chunks of time to sit down, write and edit. On average, each piece took 5-7 days before it went from conception to presentation. Of course, a small handful took 2-4 weeks. Equally so, there were a few on the other end of the spectrum that took less than 24 hours. But the more time I gave myself to think about each piece, the more robust each piece became. So, my process evolved as a function of my schedule.
Today, at least twice a week, I still allocate two hours to sit down, write and edit. I still find my creativity at its height right before I hit the haystack. And I still make the bulk of my edits in the morning. But I also give myself time to be bored. Time to just think with no intended purpose or goal, when I take long drives or in the shower or during a morning exercise routine. And as long as there seems to be a strong correlation between time to be bored and my creative output, I’ll continue this process in the foreseeable future.
Rolling Funds and the Emerging Fund Manager – A deeper dive to AngelList’s Rolling Funds and what that means for the emerging manager. Since then, I have learned some new insights on that front, which I’ll include in a future blogpost. That said, as an addendum to this blogpost, while much easier to raise capital from accredited investors, do beware of vintage quarters, especially for LPs. If you miss out on a quarter where the GP makes an incredible investment, you miss out on the carry there.
Should you get an MBA as a founder? – Admittedly, this one’s ranking came as a surprise to me, but in hindsight, I know many founders, and professionals in general, wrestle with the pros and cons of advancement education as a means of career development.
#unfiltered #57 True Vulnerability Is Messy – I’ve hosted a number of social experiments as well as vulnerability circles, but it wasn’t till my conversation with my good friend, Sam, that I realized what true vulnerability meant. Not the kind that’s been romanticized by Silicon Valley and the wider media.
My Top Founder Interview Questions That Fly Under The Radar – Investors rarely share their rolodex of questions with founders. And understandably with good reason. But I’ve never been one to optimize for ‘gotcha’ moments. If you’re building a business that the world needs, the last thing you should be worried about is what kind of curveball questions investors can ask you. In this piece, I share my top 9 questions (outside of the usual few every investor asks) and my rationale behind each.
How to Find Product-Market Fit From Your Pricing Strategy – The broader business world has always found PMF through some cousin of the NPS score and/or usage metrics. While those are still extremely pertinent, I find it illuminating to view PMF through leading indicators like pricing, rather than lagging indicators, like usage.
14 Reasons For Me Not to Source This Deal – One of my more tongue-in-cheek posts about founder red flags. I imagine a large contributor to its current ranking is due to the fact that my buddy, DC, reposted this on his blog as well.
#unfiltered #56 How Thirteen Technology and Thought Leaders Break Down Self-Doubt – One of my favorite blogposts I wrote this year, written during one of my most emotionally-turmoiled times. These 13 were my North Stars, when I found it hard to see the night sky. Hopefully, they might serve as yours in some capacity as well.
All-Time Most Popular
All the essays I’ve ever written, ranked by most views:
10 Letters of Thanks to 10 People who Changed my Life – Every year, during the holiday season, I write a plethora of letters of thanks to the people who changed my life in my short years of being alive so far. I wrote this piece back in 2019 sharing what I wrote word-for-word publicly for the first time. I never expected this essay alone to account for a plurality of your views. This is the only one of my now 200 blogposts that draws in readership almost every day since its inception. In 2021 alone, this one blogpost accounts for over a third of this blog’s viewership. The power law is truly incredible.
My Cold Email “Template” – I’ve had the fortune of meeting some of the most respectable people in the world and in their respective industries. Many of whom I met through a cold email. In this essay, I share my playbook as to how I did and do so.
The Third Leg of the Race – An oldie, but a goodie. This notion is as true now as it was when I wrote it last year. The third leg of the race is always the hardest, but it’s the one that’ll decide if you win or lose.
My most memorable pieces in 2021
Because of this blog, I’ve had the chance to share my voice and thoughts, yet also pick the brains of some of the most brilliant people in the world. So I hesitate to even rank my favorites ’cause almost every blogpost I write has a special place in my heart. Nevertheless, if I had to pick and if I’m being honest, there are a handful that would go on my personal Mount Rushmore this year. In no particular order…
The Investor Purity Test – People in venture capital often take themselves as well as their work too seriously. And not that they shouldn’t, but everyone deserves a little satire about their job. Ours is no exception. So I created a mini quiz to see how pure you are from the woes of early-stage capitalism. Have fun!
#unfiltered #61 How To Host A Fireside Chat 101 – After hosting a series of fireside chats, panels, and podcast episodes (the latter yet to released), I share what I’ve learned in this essay. It includes not only how I think about asking questions during the chat, but also how I prepare for the conversation.
Startup Growth Metrics that will Hocus Pocus an Investor Term Sheet – I always tell founders to lead with the metric that will “wow” an investor in every cold email and/or warm intro. Earlier this year, I broke down just what kinds of metrics and their respective benchmarks that will wow an investor.
Creativity is a Luxury – Back in May, I sat down with one of the most creative people I know – DJ Welch. And asked him how he regularly found inspiration. To this day, I still re-read this blogpost to help me out of a writer’s block when I’m in one.
#unfiltered #53 A Different Way To Count – Most people count their lives by the years that pass. But, what if our unit of measurement wasn’t years, but the number of presidents we live to see or the number of vacations we get to have with our significant other? You might see life quite differently.
#unfiltered #51 The Fickle Jar – I have a lot of ideas. Most of which are either completely silly, ludicrous or require time I am willing to prioritize. I’ve known anecdotally that very few actually make it past the Mendoza line. Nevertheless, thanks to my friend, I now have a visual way of tracking my promiscuity between ideas.
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!
This isn’t a new question. I’m sure most of you have heard of this question before. But recently, I realized how powerful this question is when you need an answer or answers for this time of the year.
You guessed it. It’s the season of giving. And holy frick, finding gifts to give during Secret Santa and to your loved ones is often much more of a dilemma than it should be. I know I’m not alone in that sentiment since the above question transpired as a result of the shared camaraderie my friends and I felt in choosing gifts. The more gifts you are expected to give, the more anxiety you exponentially feel.
So without giving away too much and to keep the element of surprise, I found this question immensely useful.
If your house were burning down right now, minus your phone and laptop, if you could only carry just one more item, what would be that item you would save from the fire?
You can always increase the quantity of items someone can save from the fire.
Some people give practical answers, which ends up being a rough proxy that they will appreciate more functional gifts.
Some people give answers with sentimental value. These individuals will enjoy gifts that have a backstory to them. The gifts don’t have to be expensive, but they carry significant value if they:
They come from the heart. Or…
They cost you an arm and a leg to get. Your gifts were the product of a journey where you went above and beyond.
Either way, the gift needs to be accompanied with a heartfelt card.
Hopefully, if you’re stuck without ideas this holiday season, this short blogpost might offer some inspiration.
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.
As you know from this blog, I spend a lot of time writing from my head. Startup, this. Venture capital, that. But comparatively little from my heart. This blog, Cup of Zhou, is not going to be the next Stratechery. Or a 20-minute VC. Or a Not Boring. For each one of the afore-mentioned, I have a tremendous respect for. Ben at Stratechery, Harry at 20VC, and Packy at Not Boring all do something I can not. And they do it really, really well. This blog is just nothing more and nothing less than me. It’s not a publicity stunt. And sure as hell, a terrible branding platform. In fact, I’m willing to shoot myself in the foot again and again, as long as I can be true to myself here.
Four people last week reached out to me. Two founders. A friend from college. And another from high school. They told me that life was tough. Things weren’t working out. And rejection sucks. They’re right. Whether your goal is to change the world or have an enduring marriage, life is rarely easy. You’re going to get that left hook more often than you’d like. And rejection fucking sucks. To those who said it gets better over time, it doesn’t. At least for me. You may get desensitized to each blow, but there will always be jabs and uppercuts that will sting more than the rest.
While I find comfort in writing my thoughts here, most people don’t have a safe space to be candid. As COVID is slowing its pace, at least in the Bay where we’ve reached a level of herd immunity, a while back, I decided to start a new series of in-person dinners where people will feel safe being vulnerable.
In hopes that this will help those hosting such circles outside of the Bay, here’s what I learned.
With both online and offline, I played around with a combination of social experiments and social observations. The former, I would lead and guide conversation through centering exercises and intentional “stage time.” The latter of which I would bring everyone together, but spend less time steering the conversation. Both were structured and all attendees were informed of the ground rules, theme for the night, and homework, oftentimes a personal story to share with the group, necessary to bring thoughtful conversation to the table.
Eyes are the windows to the soul
In group settings, shyer attendees would allocate more of their eye contact when speaking towards people they were familiar with. And given that I bring strangers (to each other) together, shyer attendees make eye contact with me – the one person they do know – more often than with others. But as they find more comfort in their fellow attendees, they slowly allocate more attention to them.
I often found that the best remedy for this was in two parts:
Make eye contact with them while speaking,
Mention their name intentionally a few more times than I do with other more confident guests, and
Once they sustain eye contact with you when you’re openly speaking to them, redirect their attention to another attendee by then mentioning an adjacent topic that the other attendee brought up, and making eye contact with the other attendee.
Give people a path to retreat for them to stay.
Vulnerability and true authenticity is tough. For some people, it’s easier to do with strangers. For others, it’s much harder to open up to people who you’ve never met before. Nevertheless, I like to err on the side of caution. Even after I send out personal invites to each person via DM or text, where I give them the context of what they’re about to embark on, I still preface the email that includes all the details, specifically the ground rules of authenticity, open-mindedness, and candor, with: Are you willing to be vulnerable?
Then right below that question:
If your answer is “no“, I completely understand, and I won’t force you to come. Just let me know if you’re opting out, as I need an updated headcount for our reservation.
But if it’s “yes“, … [read on]
And in that same email, everyone is BCC’ed. The guest list on the calendar invite is also not visible to each guest.
Guests have multiple opportunities to opt-out. And they should if they’re uncomfortable with the setting, since the people who do come are the ones who will truly find value in having a vulnerability circle.
Being time sensitive doesn’t matter
I initially thought that people really cared that each session was going to last 2 hours and everyone only had 15 minutes of “stage time”. And the implicit promise that I would be cognizant of everyone’s times mattered. And while it still does to a reasonable degree, it hasn’t seemed to be a priority for folks especially in my social observations. The only times it does matter are:
The energy in the conversation is waning and people start noticing hot silence, as opposed to cold silence.
Borrowing the terminology of “hot” and “cold” from Jerry Colonna, hot silence is what most people deem as awkward silence. A silence where people intentionally seek to fill the void. On the other hand, cold silence is where people are comfortable with or seek comfort in the absence of speech. Either that it lets ideas and thoughts ruminate or there is a space for tranquility that one might find calming.
Someone has another commitment right after the event.
People who don’t enjoy the conversations, topics, or people.
Luckily, this last one has yet to happen since I curate each person who comes to these circles myself. But, given how many more circles I will host in the future, it’s something I’m aware might happen.
Conversely, many of the ongoing conversations former attendees are still having with each other have come from circles that have gone overtime. This is something I’ll continue to have my pulse on to see if anything deviates from this thesis.
In closing
These vulnerability circles are only the first of many more to come. And of course, future circles will come in different variations. The ones I have planned for early next year thematically revolve around the absence and the dulling of particular senses, in order to heighten other ones. And you betcha I’ll have much more to write about then.
#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!
For years, I’ve given myself the lazy excuse. “I’m an introvert, so it’s okay if I’m bad at group conversations.” Empirically, the larger the group, the more I regress to being a wallflower. I was much more proficient at one-on-one and small group conversations than larger conversations. To be exact, to quote my friend, I was the “most David-like” in groups of 4 or less. I began to struggle in groups of 5-8. 9+ were the bane of my existence, at least on the front of contributing meaningfully to the conversation. And for the longest time, I never thought to look into that notion more, other than put myself in situations with larger groups and force myself to talk. I merely attributed my inadequacy to introversion and shyness.
For luck to stick
Yet, luck always has a way of finding its way to you. And if you’re curious, the best way to increase the surface area for luck to stick comes in two parts:
Say yes meaningfully to more things.
Have a bias to action.
What does saying yes meaningfully mean? This isn’t about saying yes to everyone and everything. This also isn’t about saying no to almost everything. I used to have a mantra, which I took from De Niro’s character in Ronin, “Whenever there is any doubt, there is no doubt.” Effectively, if I ever find myself in doubt, I shouldn’t hesitate to say no. But if you’re like me, I have the ability to second-guess everything. What can I say? I have a wild imagination. Eventually, that mantra led me to say no to almost everything in pre-2021. Subsequently, I cannot even imagine the number of opportunities I let slip through my fingers.
Saying yes meaningfully, on the other hand, meant my “yes” framework only needed to rely on a yes to at least one of two questions:
Does this make me jump out of my chair right now?
If I pursue this project, will I obtain skills, knowledge and relationships that will transcend the outcome of the project itself?
On the other hand, having a bias to action merely means to follow through with whatever you say you will do. Actions should always follow your words. If you say it, mean it.
Responsibility and accountability
A few months ago, a few of yes’s started to snowball. I began hosting fireside chats and panels, with an audience many times larger than the upper limit of my extroversion.
Unlike when I’m interviewing people for this blog or for a small podcast project I’m doing on the side with a friend, fireside chats are live by design. And because of that fact, backspace is not my friend.
Yet, despite it all, I didn’t succumb to the pressures of “extroversion”. Paired with a comparatively lower level of apprehension, I was and am more often looking forward to rising to the occasion in these conversations than in any other large group conversations. One might argue fireside chats and panel discussions are still small group conversations. It is… until you try to include audience participation during these conversations.
But why? Why did it feel more natural to host these fireside chats, panels, and group social experiments yet still struggle in ordinary group conversations?
I thrive on responsibility. The greater my sense of responsibility, the better I do in a conversation. Often times, the roles of each participant in a conversation aren’t clear. Who’s asking the questions? Who’s moderating the conversation? Should there even be someone leading the conversation? If things turn awkward, is it any one person’s fault?
At large, we also see this in group conversations – online and offline. On average, the larger the group, the less each individual feels accountable to contribute meaningfully to the group.
In 1:1 conversations, the responsibility for a great conversation is split 50-50. There’s nowhere to hide. In 3-person groups, it’s 33-33-33. In 4, it’s 25-25-25-25. And so on. At some point, often starting around the 4-person mark, people start feeling that the conversation can go on with or without them. In these fireside chats, it was very clear that it was host and guest’s responsibility for a great conversation. So despite boasting a larger headcount, the responsibility was largely split 50-50.
The lessons
While my goal is to be competitive in the top 0.1% of hosts, it’d be crass to say I started with any level of proficiency. Merely a passion. A passion to learn and help guests be their best selves. And when both guests and the audience walk away from the conversation, both will have felt that was an hour well-spent. As the theme of this blog is building in public, I’d love to share the start of this journey with you.
As such, here are a few lessons I’ve internalized so far:
Do your homework. My goal is always to know my guest(s) better than they know themselves at that point in time – specifically, in my rabbit hole research, finding things that warrant the “How did you know that” response from my guest. I start this process 4 weeks in advance. On average, I spend about 5-10 hours of research per guest, covering:
Socials,
Content they’ve created (if any),
PR/media articles,
Podcasts/interviews, and
Cross-referencing with mutual friends. Most of the above I find across 7-10 pages of Google search results.
Prep for more questions than you need. Usually for every half hour, you need 2-3 good questions, but always prepare 6-7 questions for every half hour as backup.
Some guests prefer having the questions beforehand to prepare; some don’t. I always ask when I invite them and respond accordingly. If they want to see the questions, I send that 1-2 weeks before the date of via email and updating the calendar invite with those questions.
Before every interview, in lieu of the pre-chat, I ask two questions. The goal is for your interview to just be another fireside chat, but that it’ll be THE fireside chat.
Fast forward 2-3 years from now, what would make our fireside chat one of the most, if not the most, memorable fireside chat you would have done up to that point? I don’t need an answer immediately, and you can also tell me right before our conversation next week, but would love to use that as a north star for our talk.
If there are any, what do you not want to talk about? Or are sick of talking about?
You’re running a two-sided marketplace. You want it to be THE fireside chat for both your guest AND your audience.
If, for some reason, I can’t find any good stories or anecdotes that need more context, I ask the guest a third question. Do you have one or two stories that when you told them privately or publicly earned you a standing ovation? Subsequently, rather than the full story, I ask for just a small teaser phrase that would help me transition the conversation into it. And well, I like to be surprised too.
If, for some reason, I can’t think of any specific/good questions, I ask the guest in the “pre-chat”:
What’s a question you wish I asked you that’s not in the itinerary? or,
What’s a question you wish you were asked, but never asked in previous interviews?
Make the conversation personal and relatable. Be sure to mix in both advice and story anecdotes. Despite all my fireside chats so far circle around a highly technical subject, what provides color is how much the guest is also a human with a life outside of work. Anecdotally, the more relatable a conversation is for the audience, the more likely they are to:
Internalize the advice, or at least consider it, and
Reach out and connect with the guest.
Depth matters more than breadth. It’s better to ask follow-up questions than to hit every question on your agenda. When sharing my questions with guests, I often tell them that “We’ll get to one, two, or some of the questions below, but I imagine we’ll run out of time before we run out of topics.” Anyone can replicate the same superficial questions as you ask. And if you only stick to the initial prompts, your interview will be like 95% of other interviews your guests would have been on. For your audience, while the strategic context is nice, the best takeaways are tactical – most of which are uncovered by follow-up questions.
Know your audience. In order for the advice and anecdotes to be useful and/or entertaining to them, you have to tailor your jokes, stories, and lessons to what would resonate with them the most. You need to find language-audience fit. Equally so, I found it extremely useful to also share the rough audience demographic with the guest beforehand.
Guests who bring their A-game are more important than guests who are just A-listers. While not mutually exclusive, there are too many potential guests out there that won’t take your interview seriously. Either via a lack of prep or treating it as a schedule write-off. It’ll be temporally relevant, but easily forgettable. And when that’s the case, neither the guest nor the audience takes much away from the conversation. Subsequently, it ends up being a waste of time for everything. When I started off, I only invited people that I knew reasonably well.
In closing
In all fairness, this essay could have been two separate pieces. But on a Friday morning watching the sun rise above the horizon with a cup of hot Pu’er tea next to me, it just felt right to share both my takeaways hosting conversations and the backstory that led me to be in that situation. Cheers. And I hope my takeaways supercharge you as much as they’ve supercharged me.
#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!
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.
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.
We force ourselves to think of an answer that isn’t always what we actually need.
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?
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?”
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?”
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:
“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.”
“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.”
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.
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.
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
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
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.”
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.
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.
Handwritten notes are notoriously hard to track. So, I have a 3-step process for this.
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.
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.
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.
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.
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.
#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!
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:
Physical activity,
A mature adaptive lifestyle to cope with ups and downs,
Little use of alcohol,
No smoking,
Stable marriage, and
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:
Reflect on what I should have asked for help in.
Understand why I should have asked for help sooner in an empirical situation.
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.
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.
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.
Will this make David from yesterday smarter?
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?
#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!
