DGQ 11: Was the David from a month ago laughably stupid?

laugh fox smile

Was the David from a month ago laughably stupid?

I’m a big fan of self-deprecating humor, but this isn’t one of those moments. Rather it’s a learning moment. While the above question is a lagging indicator for personal growth, it nevertheless deserves to be measured. After all, as the great Peter Drucker would say, you cannot manage what you cannot measure.

The timeframe of evaluation

Why a month? Why not a week? Or not a year?

In the business world, there’s a concept called the rule of 72. Effectively, 72 divided by the growth rate is the time it takes to double. For instance, if you’re growing 30% month-over-month, 72 divided by 30 is 2.4. So, if you’re growing revenue at 30% every month, you’re going to double your revenue in roughly two and a half months.

It is equally as analogous for personal growth.

time it takes to shock yourself = 72 / rate of learning

Let’s say you’re a first-time founder, and you only knew 10 things about how to start a business. But every day, you learn one more thing – via podcasts, articles, blogs, classes, you name it. Give or take a 10% growth rate. You will double your knowledge in about a week. Hopefully enough to shock the you from a week prior. Or take another example, many self-help books ask you to commit to getting 1% better every day. Assuming you consistently do that, you would have doubled your experience in about 2.5 months.

That goes to say, the faster you want to grow, the shorter the timeframe should be for you to look back and reflect on your “stupidity.” For me, it is in my nature to be hungry for knowledge, and I really love learning about things I thought I knew and what I didn’t know. For now, as learning is a top priority for me, a month sounds like a reasonable timeframe to shock myself. I also use the term “stupidity” lightly and with notes of self-deprecating love.

The shock factor

But how do you measure personal growth? Something rather intangible. It isn’t a number like revenue or user acquisition. Some people might have a set of resolutions or goals that is tangible and quantitative – say read two books a month or exercise an hour four days a week. Great goals, but they are often based on the assumption that movement is progress. The two aren’t mutually exclusive, but neither are they synonymous. The former – movement – lacks retrospection.

There were, are, and will be days, weeks, and months, we may just be busy. Our schedule is packed. We’re a duck paddling furiously underwater. And we’re gasping for air. And while our body and mind are exhausted, our body and mind have not expanded. I know I’m not alone when I think to myself, “Wow, I did a lot, but I still feel like I’m not moving anywhere.”

Our brains are unfortunately also poor predictors of the future. We use past progress as indicators of future progress. But while history often rhymes, it does not repeat. Our predictions end up being guesstimates at best.

So I look into the past. I measure my own personal growth emotionally – by shock, very similar to how Tim Urban measures progress of the human race (which I included at the end of a previous essay). I don’t know what the future will hold and neither will I make many predictions of what the future will hold for me. If I knew, I’d have made a fortune on the stock market already, in startups, or on crypto already. What I can commit to is my relentless pursuit of taking risks, making mistakes, and trying things that scare the bejesus out of me. Since only by making new mistakes will I grow as a person. What I am equipped with now can be mapped out by the scar tissue I’ve accumulated.

Coming full circle, what’ll make me realize and appreciate my mistakes and failures more is knowing that as a greenhorn I was laughably stupid.

But if, in retrospect, David from a month ago sounds like quite the sensible person, my growth will have gone from exponential to linear. Or worse, flatlined.

For founders

And now that I’m thinking aloud – or rather, writing aloud (which may deserve its indictment into the #unfiltered series), this might be a great line of questions to ask founders as well.

As a founder, what was the last dumb thing you did? When was that?

And before that, what was the second most recent dumb thing you did?

And the third most recent?

There’s the commonly repeated saying in the venture world. Investors invest in lines, not dots. Two’s a line. Three’s a curve. I want to see how fast you’ve been growing and learning.

Why such a question?

  1. If we’re in it for the long run, I wanna assess how candid and self-aware you are. Pitch meetings often depict a portrait of perfection. But founders, like all humans, aren’t perfect. For that matter, neither are investors.
  2. Venture capital is impatient capital. We demand aggressive timelines, and honestly, quite toxic to most people in the world. Given that, if you’re going to learn how to hustle after investors invest, you’re going to have a tough time convincing investors. But if the hustle is already in your DNA, that bias to action lends much better to the venture model.

Photo by Peter Lloyd on Unsplash


Thank you to V. who inspired this blogpost.


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.

DGQ 10: Questions Should Not Be Perfect

perfect questions, reflection

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.

Photo by Faye Cornish on Unsplash


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


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

DGQ 9: 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?

christmas, gift, present

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.

Photo by Joshua Lam on Unsplash


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


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

DGQ 8: What challenges are you facing right now?

tree, hand, help

How can I help you?

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

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

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

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

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

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

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

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

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

Photo by Neil Thomas on Unsplash


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


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

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

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

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

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

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

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

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

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

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

Photo by J W on Unsplash


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


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

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

ocean, sibling

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

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

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

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

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

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

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

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

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

Photo by Limor Zellermayer on Unsplash


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


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

DGQ 5: What startups would I love to have in my anti-portfolio?

ice cream, mistake, anti portfolio

In the venture world, there’s this concept of the anti-portfolio. A portfolio for incredible startups you had the chance to invest in, but chose to pass on. Usually the startups that qualify to be in this anti-portfolio have already reached mainstream – either having gone public and/or have reached unicorn status. For anti-portfolio references, I highly recommend checking out Bessemer‘s or tuning into Samir Kaji’s Venture Unlocked podcast, where he asks each guest about their anti-portfolio.

But having chatted with a number of incredible investors, what’s more important than names on an excel sheet is the lesson or lessons we take away from passing on the greats. Those lessons are the very answer to one of the most insightful questions an LP (limited partner) can ask. “How does your anti-portfolio advise your current investment thesis?”

In a similar way, life is a mixed bag of engineered serendipity and endured scar tissue. Our past mistakes inform our future decisions. You learn how to handle kitchen cutlery after cutting yourself a few times. You learn to walk after stumbling. And you learn to communicate after making a fool of yourself. We are a product of the scar tissue we’ve accumulated.

I’m in my first inning in the venture world, and admittedly, way too early to have any true hall-of-famers in my anti-portfolio. So rather than looking into the past from the present, I thought I’d look into the “past” from the future. A “past” that has yet to come, but will be defining of my future. Something Mike Maples Jr calls backcasting. Starting from the future and making my way back to today, along the way, figuring out what I need to do to get to that future. If you’ve been following this blog for a while, you know I’m a big fan of his mental model. “The future doesn’t happen to us; it happens because of us. […] Breakthrough builders are visitors from the future, telling us what’s coming.”

Rather than what startups are in my anti-portfolio, what startups would I love to have in my anti-portfolio?

On a similar note, for non-investors: Ten years from now, what are mistakes you’d want to have made that you tell yourself that it was a decade well-spent?

Photo by Sarah Kilian on Unsplash


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


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

DGQ 4: How much would I sacrifice to obtain this opportunity if I no longer had it?

hands, sacrifice

I was chatting with an engineer exploring new opportunities yesterday. He was at an inflection point in his career and had two incredible paths before him. One, join a product or venture studio and get his hands dirty building different products simultaneously. Two, find a co-founder and start his own company. Both had immense appeal to him. And he was unsure what path he should take, in fear he might like the other path more once he committed.

The feeling of regret is often inevitable. Especially when you have the incredible options before you, but without the luxury of time. We often ask ourselves, “How much do I value each opportunity?” Most of the time we do a quick mental calculation. We look at the biggest value of each opportunity and their future potentials. For those who prefer a more nuanced approach, we create two (or more) long lists of the pros and cons of each. Both approaches are extremely rational.

Yet, there’s still something missing. Either something that gnaws at our conscious telling us, maybe there’s something we haven’t considered. Or realizing that in constructing these lists we’ve made the decision way more complicated than it needed to be.

Rather the question I find that offers more clarity is, “How much would I sacrifice to obtain this opportunity if I no longer had it?

Humans are naturally loss-averse. We react more strongly to losses than we do to gains. For instance, we feel the pain of losing our wallet with $100 in it, than we feel the ephemeral joy of winning $100 in the lottery.

At the same time, we tend to take most things for granted until they are taken away. There are a million and one examples. We often don’t appreciate our significant other until they leave us. We take our parents for granted until they are no longer with us. The same is true for friends, homes, personal belongings, and memories.

I also prefer the nomenclature of “I” over “you”. Unlike rational decisions, where it is most insightful to abstract oneself from the situation, irrational decisions require a true introspection of oneself. After all, regrets aren’t usually rational.

While I can’t speak for everyone, my best decisions have often been a permutation of rationality and emotions. When the nuance of each decision leads to an incalculable algorithm and frankly, decision paralysis, I find it useful to channel emotional loss as a tool to make tough choices in life. Pursuing new opportunities, at least for me, is no exception.

Photo by Stormseeker on Unsplash


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


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

DGQ 3: The Alter Ego of “How are you?”

For a while, I’ve been testing a new opening line to a conversation that isn’t “How are you doing” or “How have you been”. Over the years, I realized the “How are you?” family of questions have zero substantive value. Repeat guest answers include “fine”, “okay”, and “good”. This family of questions are often placeholder for “I don’t know how to start the conversation.” And hold as much value as “like” or “umm”.

I will admit that sometimes people do mean it when they ask “How are you?”. Yet, oddly enough, in those moments, the question becomes twice as powerful when asked again in quick succession. “How are you really?”

Don’t get me wrong. Often times, my knee jerk reaction is still “How are you?” for more instances than I’m willing to admit. But I’m working on changing it. After all, I’ve already seen the amazing results of its alter ego.

This is admittedly less of a DGQ (damn good question) and more of a DGT (damn good tactic). Instead of asking a question, make a speculation as the icebreaker. The more detailed the speculation, the more engaged the response. In practice, adding a flare of exaggeration often helps lighten the mood, but too much and it might reflect poorly on your first impression. Metaphors and similes often help a lot.

Here’s are a couple examples that I’ve used in the past:

Instead of…Try…
What did you do over the weekend? If they look worn out, “You look like you fought tooth and claw with your two children over the weekend. Who won?”
If not, “You’re smiling from ear to ear. You look like you just cleaned the table at poker night.”
What do you do for a living?“I’m going to take a wild guess here. You’re an award-winning freelance designer who moonlights as a webtoon artist that just sold 50,000 copies.”
“Don’t tell me what you do. Let me take a stab and tell me if I’m right or right. You’re a recovering investment banker and found that you had a talent for music development
How are you doing?“You look like you’ve shaved 10 years off with that new keto diet.”
“That new dance class is really working out for you, isn’t it?”

Always default on positivity rather than negativity. And if your brain still goes to the negative, try adding in some lightheartedness. If you know the person already, do a bit of light research on their socials to give some credit to your speculation. If you don’t, observe their habits and apparel as a starting point. Comment on what you think they’re really proud of (i.e. physique, fashion).

People love to be heard, and letting people know that they will be heard before they even speak provides them the safety net to engage in thoughtful conversation with you.

There is a caveat. It works far less effectively when you’re in a short call and the other person is focusing on making a transaction than considering the potential of a long-term relationship. That’s not your fault. Some people are just like that, and it’d be a waste of your time to try to convince them otherwise.

As with all great ideas and tactics, this too is not original. Every time someone makes me really feel at home or when a friend tells me someone makes them feel like the most important person in the world in that moment when they converse, I observed their behavior. And many of those individuals, some who ended up being good friends of mine, used the above tactic in one way or another.

Photo by Jeremy Zero on Unsplash


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


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

DGQ 2: How do you differentiate a good founder from a great founder?

typewriter, good vs great

By far, this is one of my favorite and most recurring questions over the years. And not just in the scope of founders, I’ve asked the same question for a multitude of titles:

  • Investors
    • On a similar note, I’ve asked investors: What’s the difference between a great investor and a great board member?
    • And it yielded some insightful answers.
  • Leaders
  • Managers
  • Executive hire
  • Marketers
  • Chefs (both since I was co-hosting a cooking competition in 2019 and 2020, but also for culinary tips to improve my own cooking)
  • Artists
  • Software engineers (when you’re hiring folks who are in a field you don’t have a strong competence in)
  • Auto mechanics (yes, when you drive a 2009 mommy van, it visits the shop more often than you’d like, but also funnily enough, one of the most reliable cars)
  • Friend versus best friend
  • Life partner

… just to name a few.

I love this question since its counterpart is often asked: What is the difference between a bad and a good founder? Unfortunately, the “bad vs good” dichotomy usually ends up being a vanity question. You don’t need a trained eye and years of experience for the average person to differentiate between a bad and a good. If you’re reasonably logical, you can tell the difference between a bad and a good in any industry. There are a few exceptions, like art, especially modern or abstract art. But the case holds for most other cases.

On the flip side, to be able to differentiate:

  • The good – top quartile (25%)
  • The great – top decile (10%)
  • And the epic – top percentile (1%)

… becomes increasingly more and more difficult the higher up you’re going. As the power law and the Pareto principle goes, the top 20% accounts for 80% of the results. In other words, the small top-performing minority account for the vast majority of the returns. For instance, the top 20% of VCs account for 80% of the industry’s returns. And the higher you go up in differentiation – from good to great to epic – the smaller the delta in inputs between the tiers. There is a far smaller difference in inputs between the top 1% and the top 2%, compared to the same percentile difference between the 50th and the 49th percentile.

Having said that, to a layperson, the most insightful answer you can get that will save you years of mistakes and failures and industry know-how is the differential between the top performers. As such, usually, I get answers that would have otherwise required a keener eye, much smarter brain, a more resilient body, and a more differentiated path than I have.

For example, here are some answers I’ve learned over the years that differentiate the good from the great:

  • VP Sales hire. Their ability to hire two rock-star directors from their network within 1-2 months of being hired.
  • Chef. Their morning routine, starting from how they set their palate in the morning to how they build a robust supply network.
  • Founder. Their ability to raise their team members’ potential and how close of a pulse they keep to their operating expenses/burn rate.
  • Manager. How radically candid they can be.

Of course, it’s one thing to know what are the differentiators and another thing to understand the differentiators. The latter requires you to internalize and cut your teeth so that you can understand the true value behind the answers to the above question.

Photo by Glenn Carstens-Peters on Unsplash


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


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