I use this question quite often as a discovery tool. My job as an early-stage investor is to find crazy, interesting people building interesting things. By the time things look less crazy (at least at face value, without digging), I’m likely too late.
To founders who are fundraising, I often ask this question with respect to VCs. Most VCs default to the usual.
Tell me about your company.
How much revenue do you have? Growth rate?
Tell me about your 2-year plan. Your financial projections.
Tell me about your competitors.
How much are you raising?
Who else is investing?
And I’ve probably missed a plethora of usual suspects when it comes to questions VCs ask founders. But I love people who ask different sets of questions. People who think different, see different, and as such ask different. How are they slicing the cake differently? What might these people be seeing that most others are not? And then, I go back and reflect… is there alpha in that way of thinking.
But first, it’s about the questions. Some examples of such… here, here, here, and here, and also here and here.
So when I ask, “What’s the most interesting question you’ve been asked so far?” to founders, they can help me uncover new VCs I may not have noticed before. Probably investing in ways the industry has not seen before. And probably also investing in companies uncorrelated with most others. At least in the early stages. When I ask it to GPs, I can find LPs whose portfolios may look different from others. Or at the very least, will have arrived at their conclusion differently than their peers.
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
But I’m so glad I did. In it, Harry shared a question he likes asking “If we were hiring someone underneath me to support him, what skills would they have?” In many ways, it’s the same as another question Doug Leone shared on his podcast as well. What three adjectives would you use to describe your sibling?
It comes down to simple purpose of trying to ask about someone’s weakness without asking them “what’s your weakness?” Why does it matter? When you’re too forward with your question, say the weakness one, recipients always end up finding ways to explain their “weakness” as a byproduct of their strength, or not really sharing a true weakness. “I’m too honest.” “I work too hard.” And so on.
While the above set of questions may not work for everyone, and probably even less so now that Harry and Doug shared it in a public arena, I can’t help but appreciate the linguistic gymnastics to find the right combination of words that gets one the answer they want. Nevertheless, I’m sure there are many more on this planet who still have yet to be exposed to those questions.
Similarly, I find it to be a damn good question to ask when doing references on potential investments. The truth is every founder or GP one invests in will have weaknesses. And that’s okay. Everyone’s a human. But in reference calls, there are two hurdles that one most overcome in their diligence:
Getting the reference to share an honest assessment of the person they know. This is especially hard when these are on-list references. In other words, references that the person being diligenced is providing themselves. Naturally, this list is full of people who are almost guaranteed to say positive things about said individual. Besides, there is absolutely no incentive to badmouth another person. Neither do most people aim to do so.
How high on the priority list is this person’s weakness? Can I get conviction on this deal even if I were to accept this weakness? Does it matter as much in a Fund I? Fund II? Fund III? If they need to hire someone to fundraise for them, is that a question of ability or network? And how crucial is it not only to the firm’s survival, but also their outperformance? If they need to hire someone to manage their calendar, that may be lower on the priority list of risks for most LPs.
Nevertheless, I find Harry’s question a great one to ask former colleagues, occasionally portfolio or anti-portfolio founders.
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
This one was inspired by Harry Stebbings’ episode with Dan Siroker that I tuned into earlier this week. In it, Dan describes his most memorable VC meeting, which happened to be with Peter Fenton at Benchmark. Where Peter asks Dan, “Dan, what’s gonna get you excited to be at this business in five years?”
In sum, what are your future motivations going to look like? Nine out of ten times, it’s likely not going to be exactly the same as the one today. And given that it will look differently, can you still stay true to the North Star of this business as you do today? What’s gonna change? What’s gonna stay the same?
For the most part, the people and the problem space are likely to stay the same. The product may look quite different though. And it’s highly likely that in five years, you would have found product-market fit. So, that’s Act I. Is it the advent of the next chapter of what your company could look like that gets you excited? Hell it might be. You can then tackle a bigger problem. A larger market. An adjacent market. Or what Bangaly Kaba calls the adjacent users. For some founders, it’s the market they always wanted to tackle, but couldn’t when they realized their beachhead market must be something else.
While I can’t speak for everyone, here are some of the answers I’ve personally come to like over the years. From either founders or fund managers:
There is no other industry that offers the same velocity of learning that this one provides.
I want my company’s legacy to outlive my own. And I want to empower the next generation of builders with the resources and the power to solve the greatest needs of our generation.
I want to go home and tell my my wife/husband/kids that I lived my fullest life today. And this is what gives me endless joy.
Act I was solving a problem I faced. Act II is solving a problem others face in our space.
Getting on the phone with a customer and hearing how much our product changed their lives makes me really happy.
If I’m not regularly putting the firm’s reputation on the line, we’re not trying hard enough. And I live for that challenge.
I want to build a world where people don’t settle for “It is what it is.”
No one else is solving the problem I want to solve in the way that I believe it should be solved.
I want to continue to be a superhero, a role model, for my daughter/son.
In many ways, it’s quite similar to the question I ask first-time GPs or aspiring GPs about their motivation.
Things in venture exist on long time horizons. For founders, it’s at least 7-9 years before an exit. For fund managers, it’s 10-15 years per fund. And that’s just a single fund. Anything more is longer. So in order to compete against the very best, you need to have long time horizons. You must have the resolve to stay the course. As Kevin Kelly says, “The main thing is to keep the main thing the main thing.”
Along the same vein, there’s also a Jeff Bezos quote I really like: “If everything you do needs to work on a three-year time horizon, then you’re competing against a lot of people. But if you’re willing to invest on a seven-year time horizon, you’re now competing against a fraction of those people… Just by lengthening the time horizon, you can engage in endeavors that you could never otherwise pursue.”
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Last week, Youngrok and I finally launched our episode together on Superclusters. In the midst of it all, we wrestle with the balance between the complexity and simplicity of questions to get our desired answer. Of course, we made many an allusion to the DGQ series. One of which, you’ll find below.
In many ways, I started the DGQ series as a promise to myself to uncover the questions that yield the most fascinating answers. Questions that unearth answers “hidden in plain sight”. Those that help us read between the lines.
Superclusters, in many ways, is my conduit to not only interview some of my favorite people in the LP landscape, but also the opportunity to ask the perfect question to each guest. Which you’ll see in some of the below examples.
Asking Abe Finkelstein about being a Pitfall Explorer and how it relates to patience (1:04:56 in S2E1)
What Ben Choi’s childhood was like (2:44 in S1E6) and how proposing to his wife affects how he thinks about pitching (1:05:47 in S1E6)
How selling baseball cards as a kid helped Samir Kaji get better at sales (45:05 in S1E8)
In doing so, I sometimes lose myself in the nuance. And in those times, which happen more often than I’d like to admit, the questions that yield the best answers are the simplest ones. No added flare. No research-flexing moments. Where I don’t lead the witness. And I just ask the question. In its simplest form.
For the purpose of this essay, to make this more concrete, let’s focus on a question LPs often ask GPs.
“Tell me about this investment you made.“
In my mind, ridiculously simple question. Younger me would call that a lazy question. In all fairness, it would be if one was not intentionally aware about the kind of answer they were looking to hear OR not hear.
The laziness comes from regressing to the template, the model, the ‘what.’ But not the ‘why’ the question is being asked, and ‘how’ it should be interpreted. For those who struggle to understand the first principles of actions and questions, I’d highly recommend reading Simon Sinek’s Start with Why, but I digress.
Circling back, every GP talks about their portfolio founders differently. If two independent thinkers have both invested Company A, they might have different answers. Won’t always be true, but if you look at two portfolios that are relatively correlated in their underlying assets AND they arrive at those answers in the same way, one does wonder if it’s worth diversifying to other managers with different theses and/or approaches.
But that’s exactly what makes this simple question (but if you want to debate semantics, statement) special. When all else is equal, VCs are left to their own devices unbounded from artificial parameters.
Then take that answer and compare and contrast it to how other GPs you know well or have invested in already. How do they answer the same question for the exact same investment? How much are those answers correlated?
It matters less that the facts are the same. Albeit, useful to know how each investor does their own homework pre- and post-investment. But more so, it’s a question on thoughtfulness. How well does each investor really know their investments? How does it compare to the answer of a GP I admire for their thoughtfulness and intentionality?
(Part of the big reason I don’t like investing in syndicates because most outsource their decision-making to larger logos in VCs. On top of that, most syndicate memos are rather paltry when it comes to information.)
The question itself is also a test of observation and self-awareness. How well do you really know the founder? Were you intentional with how you built that relationship with the founder? How does it compare to the founder’s own self-reflection? It’s also the same reason I love Doug Leone’s question, which highlights how aware one is of the people around them. What three adjectives would you use to describe your sibling?
Warren Buffett once described Charlie Munger as “the best thirty-second mind in the world. He goes from A to Z in one go. He sees the essence of everything even before you finish the sentence.” Moreover in his 2023 Berkshire annual letter, he wrote one of the most thoughtful homages ever written.
As early-stage investors, as belief checks, as people who bet on the nonobvious before it becomes obvious, we invest in extraordinary companies. I really like the way Chris Paikdescribes what we do. “Invest in companies that can’t be described in a single sentence.”
Invest in companies that can’t be described in a single sentence
And just like there are certain companies that can’t be described in a single sentence — not the Uber for X, or the Google for Y — their founders who are even more complex than a business idea cannot be described by a single sentence either. Many GPs I come across often reduce a founder’s brilliance to the logos on their resume or the diplomas hanging on their walls. But if we bet right, the founders are a lot more than just that.
Of course, the same applies to LPs who describe the GPs they invest in.
In hopes this would be helpful to you, personally some areas I find fascinating in founders and emerging GPs and, hell just in, people in general include:
Their selfish motivations (the less glamorous ones) — Why do this when they can be literally doing anything else? Many of which can help them get rich faster.
What part of their past are they running towards and what are they running away from?
All the product pivots (thesis pivots) to date and why. I love inflection points.
If they were to do a TED talk on a subject that’s not what they’re currently building, what would it be?
Who do they admire? Who are their mentor figures?
What kind of content do they consume? How do they think about their information diet?
What promises have they made to themselves? No matter how small or big. Which have they kept? Which have they not?
How do they think about mentoring/training/upskilling the next generation of talent at their company/firm?
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
“I won’t forget the first time I saw Jason Peters do a one-on-one pass set with Trent Cole, and being amazed at the speed, balance, and power I just witnessed. It reminded me, or looked like, a grizzly bear wrestling a panther. It was so impressive, it made me question if I was good enough to play in this league.”
Much of this DGQ was inspired by Jason Kelce’s retirement speech, delivered with the prose and candor befitting of a legend. Which for those who have yet to read/listen to it, it’s 24 minutes that will be well-spent, whether you’re a sports, football, or Eagles fan or not.
There’s something really special about being the underdog. Whether you feel it or others say it. That slight chip on the shoulder, that measured level of imposter syndrome, is fuel to the fire. There is a distinct advantage for being the dumbest person in the room, knowing that there are mentor figures on the team you can learn voraciously from, even if by osmosis. And if you do have naysayers, you have the greatest privilege to prove them wrong. It means that you have space to grow. That journey ahead, at least for me, is quite exciting.
Although not framed nearly as eloquently as Jason Kelce put it, it’s something I think about a lot. Does the overall level of the team make me question if I’d be a good enough to play in this industry?
Challenge is as scary as it is thrilling.
Similarly in VC, we often say it’s an apprenticeship business. And it’s true. Almost every great investor I know had someone who took them under their wing and showed them the ropes. Sometimes a set of people. And it’s incredibly hard to learn and check your blindside without someone who plans to dedicate a good portion of their time to do so. That said, the next best you can get is to learn by osmosis.
You are the average of the five people you hang out with most. So if you have the chance to live and breathe alongside people who intimidate you with their skill, intellect and the way they execute in a good way, take it.
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
I first heard this question from Morgan Housel quoting a Navalism (for the uninitiated, that means has its source tracing back to the one and only Naval Ravikant). And it makes you think, that in the multiverse, where each version of you lives a different life and makes different choices, what would stay constant?
These are things that are not attributed to luck. And as Morgan mentioned, “those are the things you want to focus on in life.” When predicting the future, many try to predict what will change, but the best bets with long time horizons are on those that don’t change. Things that aren’t attributed to luck. Or chance. In this world we live in, you’d be quite surprised the number of small, accidental decisions we make that lead to life-changing events.
Like you being 10 minutes late to a party meant that you somehow just showed up at the same time as your future spouse. And it was because of that, that led you to have a two-hour long conversation with him/her. Otherwise, you’d have spent the entire party hanging with your college friends.
Or because you forgot to bring your umbrella on a day it rained, it made you run into a hotel for shelter, where you stumbled upon the investor who led your Series A round. Because he/she too forgot to bring an umbrella.
Of course, I could play hypotheticals forever. Although I find it’d be a fun exercise to really examine how much of your most life-changing moments were due to serendipity.
As someone who makes their living on attempting to predict the future, that means we have to go back to first principles. For instance, human nature. Reid Hoffman’s framework that all great consumer products tap into one of the seven deadly sins. Something that despite innovation is timeless. Anecdotally, I do find some of the greatest investors — LPs and GPs alike — to be avid students of history, philosophy or psychology.
“Email is a wonderful thing for people whose role in life is to be on top of things. But not for me; my role is to be on the bottom of things.”
In life, while catchy and interesting and the talk of the town for that brief moment, sometimes it’s better to get to the bottom of things than to stay on top of things. After all, you only have so many letters on your tombstone.
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
A while back, I stumbled across this question by Siqi Chen while doomscrolling through Twitter, and I couldn’t help but do a double take on it. It’s something I often worry that I miss when founders or GPs pitch me, but also when I hostfireside chats. I worry in my myopia with hitting an agenda of questions, I may miss the most important part about the person sitting across from me. In any interview setting, interviewers always have a pre-destination in mind. And often it’s the onus of the interviewee to alter that flow if a dam is restricting the power of the torrent. In other words, your strength. It’s why I ask, “Are there any questions you have yet to be asked, but wish someone were to ask you?” But I like Siqi’s way of asking it a lot more.
After 20 years of interviewing candidates, I've found this to be the single most useful interview question:
"What is your greatest strength … that you are most worried about not coming across in an interview setting?"
Take ambition as a strength, for example. Really hard to tell by just looking at a resume, especially one who says they are and someone who actually is.
At the same time, there’s a beautiful line that the late Ingvar Kamprad, best known for founding IKEA, once wrote. “Making mistakes is the privilege of the active — of those who can correct their mistakes and put them right.” And that’s okay, in fact heavily encouraged for anyone who has ambitions. Because in order to achieve the extraordinary, you cannot pursue the ordinary. You have to tread where no one has treaded before. And a lagging indicator of that is the number of mistakes and scar tissue you’ve collected over the years. So, in an interview, to best illustrate your ambition, you have to talk about the lessons you’ve learned to get here. The greater the mistake, the more risk you took. And often times, the greater the ambition.
Kevin Kellyalso said recently, “I’d like to give a little story of a car, and you need to have brakes on the car to steer the car. But the engine is actually the more important element, and so there are people and there are organizations, and there are methods that are going to be doing the braking, and I think they’re essential. I want brakes in the car, but I just feel that the brake can overwhelm and cause stagnation, and that we also wanted to remember to focus on making the engine even stronger, and so I emphasized the engine.”
In an interview, it’s the difference between promotion and prevention questions. As Dana Kanzeonce shared, ““A promotion focus is concerned with gains and emphasizes hopes, accomplishments, and advancement needs, while a prevention focus is concern with losses and emphasizes safety, responsibility, and security needs.” As such, in an interview, you want to channel your energy to being asked at least one promotion question that highlights your strength.
Conversely, as I’m writing this right after reading Chris Neumann‘s most recent post on fake FOMO, creating a fake sense of urgency is one of the best ways to ensure your greatest strength won’t come out during the interview.
Today’s just a short blogpost. Just to say I’m a fan of Siqi, one of the greatest masters of storytelling, and this question. In case, you’re looking for more Siqi content, check out here and here.
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.
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 views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Whenever I host fireside chats, I always ask three questions before the talk begins, usually a week in advance.
What would make this interview the most memorable one you’ve been a guest for even two years from now?
Are there any topics you don’t want to talk about? Or are sick of talking about?
Are there any questions you have yet to be asked, but wish someone were to ask you?
On top of the above three questions , occasionally, I ask a fourth. Do you have a home run story that has gotten you a standing ovation in the past — privately or publicly?
The goal is simple. Despite hours of research and asking mutuals, sometimes I still can’t find anything that’s humanizing about my guest. And I know for a fact that all humans are imperfect. And that imperfection makes each person relatable. Just like when Neil Gaiman met Neil Armstrong. But recently, I’ve fallen in love with a new way to phrase the fourth question.
What is a story that you’ve told or have yet to tell where you either fight to hold back tears or fight to hold back giggles?
On my flight to New York recently, I watched a movie starring one of my favorite actors in the world, Tom Hanks, which inspired this question. And, subsequently this blogpost. A Man Called Otto. Inspired by Fredrick Backman’s A Man Called Ove. And I’m not ashamed to say, I cried during that movie. While Rotten Tomatoes may not give it the score I think it deserves, it was well-written and well-produced. Through it, I realized that powerful stories are powerful not because of how awesome the protagonist is. But by how relatable their weaknesses are. Their limitations. I’ll give an example… to avoid spoiling the afore-mentioned movie.
Spiderman isn’t awesome because he has mutant powers. He’s awesome because he’s prone to all the emotions and struggles, be it love, bullies at school, a horrible boss, and how he acts out against all of that. Spiderman’s much more relatable than a super billionaire who owns all the gadgets in the world or an alien from another planet. He’s just a kid from Brooklyn. Or Queens, depending on which Spiderman suits your fancy. And as Brandon Sandersononce said, limitations are more interesting than powers. Limitations make us human. And characters who exhibit humanness and still somehow overcome impossible odds are stories that are passed from generation to generation.
That said, storytelling, outside the realm of superpowers, is equally as true. In a world where appearance and social capital goes a long way, trying to be perfect, to look perfect, and to act perfect is a fallacy in the modern era. While we know we’re not perfect, as a society, we continue to strive for perfection.
After watching a lot of movies, and in my free time, watching acting lessons (FYI, would fail as an actor, but still find the craft fascinating.), I’ve learned we don’t cry when watching movies because the characters cry easily. We cry because the character is trying to hold back their tears. And we don’t laugh during a show or a movie because the comedian laughs easily. We laugh even more because they’re trying to hold back their own laughter. The narrators and characters we see are a reflection of who we truly are.
In many ways, if someone cries easily, it relieves the audience of the ability, some artists may call it responsibility, to cry. Someone, the actor or actress or character has diffused the tension already. But if they fight to hold back their tears, holding back the floodgates, we as the audience are more likely to cry in their stead.
Now I say all of this because I find most fireside chats and interviews unrelatable. Now it’s a product of many things. And I genuinely believe a plethora of individuals do have something powerful and insightful to share, but the stage needs to be ready for them. It’s rare for guests to drop some head-turning advice in the first 10 minutes. Which means… it’s up to both the host and the guest to hold the audience’s attention long enough, as well as create enough opportunities for the guest to shine. The above question, in my opinion, does both.
So all in all, going forward, rather than asking for a home run story, I will ask for stories where people are just people. And for stories that mean a tremendous amount to the people telling them. That they have no choice but to let even a little bit of themselves out emotionally.
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.
The views expressed on this blogpost are for informational purposes only. None of the views expressed herein constitute legal, investment, business, or tax advice. Any allusions or references to funds or companies are for illustrative purposes only, and should not be relied upon as investment recommendations. Consult a professional investment advisor prior to making any investment decisions.
Over the past 12 months, I’ve done over 100 interviews and fireside chats. While there are the more popular lessons out there, like asking follow-up questions and breaking the ice with your guest with a pre-interview chat or having rapid-fire questions at the end, for the purpose of this blogpost, I’ll be sharing some non-obvious lessons I picked up in the past year.
Never start with a question on career.
Ask your guest three questions before the interview.
Do enough research to be literate in the subject you’re interviewing for.
Prep the audience for questions.
Ask Yes / No questions.
Never start with a question on career.
The first question always sets the stage for the rest of the conversation, especially how vulnerable and candid the guest would be.
The best question in my experience to start with is always a surprise to the guest, as my goal for every interview is to get to know the guest better than they know themselves at that moment in time.
For how you measure success… if that respond with, “How did you know that?”
In practice, it looks a little something like… “I want to start this chat a little off-center. In the process of doing homework for this conversation, I came across the name: Bootstrapping Bill*. Could you share what that name means to you?”
*Footnote: This can be a high school or college nickname or an activity that they were heavily involved in that’s not related to their current career. Or a role model they had when they were younger. Other starter questions can be about quirks they used to have or still have that are:
Not embarrassing
Something that only they have.
For example, for some of my interviewees, I found out:
That someone used to write code on a notepad
A longtime fandom around Gary Keller
A nickname the guest used back in his street dancing days
A class they really enjoyed taking in college and an art professor who inspired her to pursue entrepreneurship
Someone who used to walk by foot 15 hours one-way just to go to a library in Cairo to download PDFs of Stanford research papers to take home and study
Of course eventually it all has to tie back to the topic at hand, which is usually through a trait they developed early on that created the person they are today. Grit. Creativity. Rebelliousness. Kindness. And so on.
Ask your guest three questions before the interview
What would make this interview the most memorable one you’ve been a guest for even two years from now?
Are there any topics you don’t want to talk about? Or are sick of talking about?
Are there any questions you have yet to be asked, but wish someone were to ask you?
Of course, also share the questions that you plan to ask before the interview. Leave it up to them whether they want to prepare for them or not. And if you do so, they’re likely to bring more robust and less generic answers for your audience. Unfortunately, not always true depending on the individual you invite and how busy they are.
Do enough research to be literate in the subject you’re interviewing for.
Unfortunately, not every A-lister will bring their A-game. Some have been busy. Others are distracted. And a handful of others frankly just don’t care. For them, this is just another talk they’ve done a million times. Not THE talk of the year. Even if it might be for you.
Luckily, it doesn’t happen too often. But it does happen. And as such, you can’t just ask a question. Instead, I like to give the speaker enough time to think of an answer. I call it the QCQ sandwich.
Start with a QUESTION.
Follow up with CONTEXT.
And close with the initial QUESTION.
I’ll give an example.
“Since you just mentioned LP-manager fit / I want to switch gears for a second… I’d be remiss not to ask you about how you think about it. In your experience, how have you seen the best fund managers think about LP construction when they begin fundraising versus when they’re about to close the fund? To shed some extra color, I’ve recently chatted with a number of emerging GPs. And there seems to be a concentration of thought leadership around… [additional context] So, I’m curious, are you seeing the same? Or have my observations departed from the median?”
Most people either only ask the question or lead with context before asking the question (I’m guilty of the latter myself from time to time).
To be fair, you may not need to use this structure all the time. But for people whose answers are typically less structured and may need some time to formulate a robust answer, this is the play. A proxy for this is if their answers only get better the more they talk or if they haven’t had a chance to look through the questions you sent them beforehand, but they typically like to.
Then there’s the exact opposite. Even if the guest speaker is well-intentioned, in efforts to cram as much info into an answer as possible, their talk becomes overly informational. I forget which world-class podcast host once told me this, but he said that that every episode he does is 20% informational and 80% entertainment. The footnote is that the 20% has to be so insightful that it can carry the episode just by itself. The sign of a good episode is if the listener walks away with at least one thing they didn’t know before.
I go back to Kurt Vonnegut‘s #1 rule on writing. Use the time of a total stranger in such a way that he or she will not feel the time was wasted.
As the MC, your goal is to be the steward for insights. The spotlight is never on you, but the question is how do you support your guest in a way that they’re able to put the best foot forward.
Prep the audience for questions
There are two angles I usually tackle from when prepping the audience for questions.
I tell them exactly what they can ask at the beginning and stay away from those topics so that the audience can ask during Q&A if they have no other questions in mind.
Give the audience time to ramp up questions by alternating between live questions and my prepared questions even in open Q&A.
“We’re going to cover a lot of ground today from [topic 1] to [topic 2] to [topic 3]. But if I don’t get to all of them, and you’re still curious about them, please keep us accountable during the open Q&A after.”
And I usually don’t get to all of the above topics, which leaves room for the audience to ask them. Before I ask my “last” question for the interview, I also tell the audience to the effect of: “This is going to be my last question, before I turn it over to everyone present today. So for anyone who would like to ask X something, in about 3 minutes, it’ll be your time to shine.”
The big takeaway is that it always takes a bit of time for the audience to ramp up to ask their questions. And this helps seed some possible topics not covered in the interview so far, so the guest also feels like they’re not repeating themselves.
Since almost every interview and fireside chat I’ve done has been virtual in the past year, this second tactic is designed when you a Zoom chat but I find is still useful when you have a shy live in-person audience. I always tell the audience to leave questions in the Zoom chat at the beginning of the interview. That I’ll call on them when we get to open Q&A. More often than not, the Zoom chat is less alive than I would like. And when it is (and I admit this has only been a more recent discovery of mine), I say:
“We’re going to try something new. During the open Q&A, I’m going to alternate between questions I’ve gotten before this chat to live questions from the audience. So feel free to pop your questions into chat, as I start with the first pre-submitted question.”
I know some MCs seed audience members to ask questions at the beginning of live Q&A for it to not seem awkward. I’ve seen it work, but sometimes I’ve also seen those 1-2 people take control of the Q&A, where the rest of the audience doesn’t feel like they have the opportunity to ask their own question, so they turn passive. With open Q&A, I try to give my audience agency to determine the flow of conversation. Sometimes, they just need an inspirational nudge.
Ask Yes / No questions
For a long time, I had this fear of asking yes/no questions during fireside chats. The main reason was that I believed it would lead to a lackluster interview. The guest would give a one-word response and that we would have radio silence after.
But, contrary to my initial belief, I realized over the past year that yes/no questions are insanely powerful, specifically in the context of public interviews and fireside chats. I do want to note that they don’t hold the same weight in mediums that are known or sought for their brevity. For instance, emails and instant messaging. Where speed is the name of the game.
It’s specifically under the circumstance where there’s an allotted time and an expectation to fill the void with content that this tactic shines. The guest would more often than not feel an urge to fill the empty void with additional thoughts and context. In that moment, sometimes they share something that is more off-the-record than they initially planned. Of course, in realizing that it is, and since most of my fireside chats are recorded, I follow up with the guest after to make sure they’re okay with the recording.
As an interviewer, at the same time, I’ve learned to hold myself back. There’s an equal if not more powerful urge in me to fill the void with questions. After all, oftentimes, this is the audience in which I had invited, and feel my reputation is on the line. If you could see below the camera, I have a sheet of paper in front of me where I write “Shut up” to myself at least twice before I jump in.
In closing
While I share all the above, just like being a founder, you could do everything right and the interview may still fall short of being ideal. And when some interviews do fall on either deaf ears or I feel I was just unable to bring out the best in people, like many others, I wonder… do I just suck at being at asking questions? Or being an MC?
It’s an iterative process. And the fun part of it all is that it makes me a better investor. I ask founders better questions. The answers I get when diligencing are more valuable.
The above isn’t the end-all-be-all. I’ve written on this topic before, and I will continue to work to be a better interviewer. But hopefully the above serves to bolster your arsenal of tactics.
Edit: Added in a fifth lesson that’s too short for a full blogpost, but longer than a tweet.
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Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
I forget where I heard this recently, but I thought it was a great breakdown of how we are all a function of our past.
When I first jumped into the action-packed world of venture, the most daunting part of the job wasn’t the spreadsheets or the modeling or asking great questions to founders or being a thought leader. It was the seemingly sustained extroversion that was necessary to be successful in the field.
Everyone, but especially the best investors, seemed naturally extroverted. And, well… I wasn’t. And neither did I want to be. To me, being an extrovert just seemed so exhausting. That said, it didn’t mean I didn’t enjoy every second chatting with amazing founders and investors. I was just — still am — the person who taps out two hours into a party. Three, max. In fact, I used to be a stereotypically shy introvert back in grade school. Comfort and safety were my best friends.
So, the reason I’m sharing all this in the first place is that we are all a product of our history. In the world of startups and VC, it seems like the best founders and investors were born extroverted and with great charisma. They were daring, rebellious, and ambitious from the start. They have these wild stories of how they broke the rules as kids and how each of those anecdotes made them who they are today. And somehow they turn each of the afore-mentioned into great Twitter threads. But I digress.
I, for one, have not had those same experiences. But when I finally entered college, I let what would have been some of my most formative experiences slip through my fingers – a freshman year crush, the opportunity to invest in a classmate who became a world-class founder, just to name a few. All of the above opportunities I was deeply curious about but didn’t have the courage to speak up. And I beat myself up over it. So today, my spurts of extroversion isn’t a trait I was born with, but motivated by the deep regret I used to and probably still do carry of my past inability to seize the moment. A past I am rebelling against.
And I know I’m not alone. Having chatted with numerous introverted founders and investors I deeply respect, I know I’m in good company. For those reading who fall under the same cohort, you are too. We just don’t speak out much, so it may be hard to tell that we exist. Of course, this is only one example among many in a cosmos of life experiences and characters.
So, as you’re charting your life’s journey and sharing it in an interview, coffee chat, or fundraising pitch:
Which part of your past are you rebelling against? Which part are you running towards?
And be honest. If you can’t be with the world, be so with yourself.
As a result of writing a soon-to-be-published blogpost on how limited partners (LP) think about investing in VC funds, one LP shared a similar line of thinking. For emerging fund managers (equally true for founders), why does this product/space mean so much to you? The answer isn’t just because you worked X number of decades in it, but something more fundamental. If you don’t have one, you might find your founder-market fit elsewhere.
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.
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
