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!
“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.
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.
There’s a comical number of debates around where the team slide goes in a pitch deck. In fact, this blogpost may end being more of a meme than have any substantive value. Nevertheless, here’s to hoping that by the end of this essay, there’s some semblance of a call-to-action for you. The “too-long-don’t read” answer for the order of your team slide is… it depends.
Why “why you” is important
First, let’s start from the “facts”.
The earlier your company is, the more your team matters to an investor. The more mature your company is, the less it matters.
If your investor doesn’t understand your answer to the “why you” question, you’re not winning any gold medals, much less a check.
Investors have, effectively, three questions they want answered in the intro meeting.
Why now?
Why this?
And, why you?
“Why now” tells an investor why they should look into the space. “Why this” tells an investor why they should look at the solution. But if we’re being completely honest, if an investor is a specialist and not a generalist, and even if they were the latter, you’re not the first person who’s brought up the exact same “why now” and “why this”. Even if you answer the first two questions perfectly, there’s still no reason as to why you should be the one to take this product to market. Investors, if they were more blunt, would just thank you for your market research.
On the other hand, if you can answer the “why you” question, you give them a reason to have a second conversation with you. And the whole goal of the intro meeting is to have the second meeting. Not to get the check. Don’t skip steps. As a footnote, your mileage will vary with angel investors and micro funds. For them, speed is their competitive advantage, not their check size nor possibly their network or resources. While they will try to be helpful, they’re not a platform – yet. If you answer the “why you”, in the worst case scenario, your investors won’t regret backing the startup. You just weren’t lucky. But they’d probably be willing to back you again if you started another business.
The reason why so many VCs regress back to metrics and traction is because you’ve failed to answer the “why you” question.
Founders haven't sold them on the "why you" so they regress to finding answers for "why this" and "why now", which typically come in the form of lagging indicators like rev and traction
Based on the above “facts”, the younger your startup is, the earlier you should put the team slide. To give investors context as to who you are. This matters a bit more for partnership meetings, as well as if this is a (relatively) cold pitch. That is, to say, if you AND your co-founders don’t have a prior relationship with the people you are pitching to, move the team slide to the beginning.
Eniac Ventures, an incredible seed-stage firm, recently wrote, “We believe that it should probably be slide 1 or 2. That’s because investors want to become familiar with the people behind the product early on, whether we’re flipping through the deck or you’re pitching us directly. When the team slide is second, it also gives you a great opportunity to walk investors through your background and impress upon them why your unique set of experiences makes you and your team the best one to build and scale the product.”
In closing
But, that might not be the case for you. The investors you pitch might have a different set of priorities. I always go back to the question: When going into the meeting, if the investor could only ask one question, what is the one question they need the answer for to give them enough of a reason to take the second meeting?
Then your pitch deck should be in that order of priority.
If you’re tackling a problem most people care little about or where it’s non-obvious, talk about the problem first.
If it’s not a revolutionary product and it already makes sense, talk about why you and your team are the best equipped to tackle this problem.
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!
One of the greatest blessings I have today is that friends often introduce me to their incredible friends. Two weeks ago, one of my good college friends introduced me to a friend he made down in LA. Sam. A brilliant aspiring fund manager. Cut her teeth with driving impact at non-profits. But above all else, her ability to host dinners with strangers caught my eye and ear. Since I’m a big fan of sharing my learnings from hosting brunches with strangers and socialexperiments. In a short span of a week, we became fast friends. Expectedly, I had to ask Sam how she brought strangers closer together at her dinners.
Last week we jumped on another call where she walked me through her process. “David, it’s easier to show you than to tell you. Are you open to being vulnerable?”
“Yes.”
“Tell me about your life philosophy.” She asked me what influenced the life purpose I have today. Over the next half an hour, we dove into the depths.
The first third was populated by a politician’s answer. I wasted zero calories jumping into my upbringing and why that has influenced the person I am today. Unwittingly then, but in hindsight clarity now, they were all narratives I’ve rehearsed before – intentionally and unintentionally. After all, they were the cookie cutter responses I’d give to cookie cutter questions most people asked.
Yet, after each of my narratives, there would be a brief pause. What lasted only mere seconds felt like eternity for me. In those moments, she was a woman of few words. Comfortable with silence, she would occasionally beckon, “Tell me more.” On the other hand, I was impatient to fill the void. The emptiness was unsettling. I felt like a circus monkey forced to perform and that the audience’s claps and laughs was the only representation of my self-worth. But that was all in my head.
“Tell me more.”
I filled the next third with stories I’ve told before but not in a while. A reminder to myself that I am more than the person who existed in just the last two years. That I’ve had 23 other years than I somehow left in the attic collecting dust. That I am not a function of my job title or the people I surround myself with currently. But rather the accretion of everything before as well. Where the first third was sharing the mold I now fit in, the second third of our conversation was sharing why seemingly disparate events and relationships in the past fit the mold I had just shared. In sum, I was still making sense of things.
“Tell me more.”
I was ill-equipped to deal with the last third. I was no longer armed with the stories I had rehearsed throughout the 25 years I’ve been alive. Analogously, I was someone who just learned what exponents and derivatives were. When my 5-year old cousin asked the fifth “why”, I didn’t have an answer for her. Not like I did with the first four.
In this case, she asked the third “why”. And I was already at a loss for words. I was lost between doubt and anxiety, between shock and curiosity. But it was in the last ten minutes when I finally dropped my guard. My guard where everything had to make sense. My guard against the fear of uncertainty, not just for the future, but for my past.
A few moments of silence passed. Once again, long, but not nearly as uncomfortable as in the beginning.
At the end of our conversation, she left me to wrestle with my own uncertainty. But with the offer to dive even deeper the next time. And I was left with my own turmoiled mind, unable to find the words outside of sweeping generalizations to express what I felt and how I felt it. While I was grasping for the Merriam-Webster to make sense of my inner entropy, she sent me the below wheel. Something she relies on, to this day, to keep her emotional vocabulary from atrophying. In being able to identify her emotions, she is better set to understand them.
As I’m writing this blogpost, her words “true vulnerability is messy” still ring in my head. And it’s in those moments we build trust and bond with each other. And also with ourselves.
The purpose of this exercise and with vulnerability is not to have more answers than questions. Bur rather more questions than answers. And the ability to ask 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!
I recently read Fable‘s Padmasree Warrior‘s breakdown of leadership lessons. Prior to Fable, she held executive positions at Motorola, Cisco, and NIO and currently serves on Microsoft and Spotify’s board. Out of all the insights she shared, I couldn’t help but reach out on one intriguing point she brought up: “Hire for expertise, not experience.”
Expertise ≠ Experience
Before reading the blogpost on her, I had never thought of expertise and experience as two separate wheelhouses of knowledge. While there is definitely some overlap, as Holly Liu, founder of Kabam, says:
Expertise and experience are similar, but not the same. It is to no surprise most people often conflate the two, myself included. Experience is a record of past events. Expertise is your ability to leverage experience to positively influence the outcome of future events.
I’m reminded of something Henry Ford once said. “If I had asked people what they wanted, they would have said faster horses.” Experience would have dictated faster horses. Expertise would have dictated why we once chose horses over other modes of transportation. And the framework to think about transportation in the next century.
Hiring for expertise
When I asked Padma, “What kinds of questions do you ask potential hires to measure on expertise rather than experience?”
She responded: “I usually as ‘if X happened what would you do?’ ‘If there is nothing here… how would you start a product?'”
I followed up with a David classic: “If I can be completely selfish one more time, and I understand if you don’t have the time, for the question, ‘if there is nothing here, how would you start a product?’ or similar ones, what differentiates between a good answer and a great answer?”
Padma added: “If someone says ‘I did this at such and such’ – wrong answer. I look for ‘I would start with … then do… then grow’.”
Everyone’s guilty of a bit of revisionist’s history when looking in hindsight. It’s in our DNA. We are the only species that create narratives from seemingly disparate data points. After talking with multiple recruiters, executives, and CEOs on the topic, I realized there is often a tendency for people connect their past achievements together and sound like they knew exactly what they were doing all along. But in foresight, that often isn’t true. There’s a lot of guesswork and uncertainty when looking through the windshield, compared to images that often seem closer in the rearview mirror.
To follow up on Padma’s thoughts, I had to ask my former professor, Janet Brady, the former Head of Marketing and Head of Human Resources for Clorox, about hiring for expertise. “I’m a big fan of situational interviewing, where I ask ‘What would you do if…?’ In the process, I am looking for (a) how would this come up, and (b) how would they approach the problem. It’s easy to make the puzzle pieces fit and make up narratives in the past, but much harder when given a situation to deal with on the spot.”
As with any matter, things are not as binary as they first seem to be. She concedes that there is validity in asking about experience as well. But the context around experience is often more insightful than the experience itself. Brady shared, “You never do something alone. If you see a turtle on top of a fence post, you don’t know how it got there, but you know it had help.” How many people were on your team? What was your role on the team? What problems did you run into? And how did you deal with those problems?
But one of her interview questions in particular stood above the crowd for me. “What did you do in this role that no one else in this role has done?” While past achievements aren’t always predictors of future progress, in this case, what you’re looking for aren’t anecdotes but general themes in life, specifically, the ability to question the status quo and act on it.
Echoing Brady’s questions on problems a hire has faced, what might be more interesting is what didn’t work out in the past. The scar tissue someone’s accumulated over the years. Marco Zappacosta of Thumbtack loves the question: “What’s your biggest professional regret?”. And he elaborates, “I’m under no illusions that I’m hiring perfect people, but I want to make sure I’m hiring people who are self-aware of being imperfect.”
Put into practice
SaaStr’s Jason Lemkin shared a great example in his blogpost. How the expertise of VPs of Marketing differ depending on what stage of a company’s maturity they earned their stripes. A corporate marketer’s experience might translate poorly to running marketing at a startup. Equally so, a seed-stage startup marketer’s job might carry much less significance in a Fortune 500 role.
Corporates focus on corporate marketing and brand marketing. A form of marketing that’s “all about protecting and reinforcing the brand once you are way past scale.” It’s less about getting your brand recognized since customers have already heard of your brand. It’s about getting potential customers over the activation energy required before making a buying decision. As Jason puts it, “the brand creates so many leads and customers all on its own.”
Startups, on the other hand, are all about demand generation. In other words, generating leads. It’s a numbers game. Spend X dollars to get Y leads, that generate five times of $X of revenue. The equivalent of an LTV-to-CAC ratio of 5x. At the same time, he notes that “brand marketing is very expensive in the early days – and frustratingly, generates zero leads.”
Someone with Z years of marketing experience might have a lot of scar tissue, but might not be able to solve the marketing problem for your startup. Demand gen folks can’t hide anywhere if they don’t get results, but corporate marketing folks can hide behind a brand. Focus on finding the expertise you need rather than the years of experience that might look sexy on a resume or on a pitch deck. As always they’re not mutually exclusive, but it’s important to know the difference.
Who knows? Maybe the next generation of lead gen is all about Twitter presence and memes, as a16z’s Andrew Chen recently tweeted.
Bottoms up SaaS founder to Enterprise sales founder:
On a bigger picture, the process of sales and marketing is a form of free education for a customer base. The better you can get your users to understand what you’re building, the more likely they will buy. Memes are just another medium of analogy and education. Better yet, of storytelling.
The better you can weave together seemingly disparate data points to create a compelling narrative without confounding extraneous variables, the greater your level of expertise. As Packy McCormick, one of my favorite writers, wrote on an a16z blogpost on expertise, “We live in a world where expertise can be justly claimed by anyone who can continue to prove it. Synthesis and storytelling are the keys to navigating that world. In a world with so much information available and fewer unquestioned experts, the ability to let large amounts of information wash over you, figure out where to dive deep, pull out the most compelling bits, and tie them all together is key.”
In closing
Hiring great talent across all levels breaks down to less of how many years of experience, but more so how you can leverage those experiences to understand and use unique and seemingly disparate data points going forward. Fall forward; don’t fall backward. An expert hire might not have all the answers to your problems, but will have built stress-tested mental models that’ll help in finding the answers for the questions you have.
Back when I was at SkyDeck, Caroline taught me that great entrepreneurs follow the “scientific method of entrepreneurship.” If I were to analogize her idea to expertise, an expert is a champion of the “scientific method of application.”
Of all the experts I’ve met – a title which is often one that society has deemed rather than being self-prescribed – they’ve almost always had an answer or multiple to a certain question. What proof would it take for you to change your mind?
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!
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?
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.
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.
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.
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.
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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Founders often ask me what makes a VC say yes. Or what they need to do for a VC to say yes. Or what they need to do for me to say yes. TL;DR: it depends. On firm, partner, thesis, active conversations, stealth investments, next fund fundraising schedules, reserve ratios, implicit biases, and more. In sum, a million reasons. And even if I knew all the above, I still can’t guarantee a term sheet.
So I can’t say what’ll guarantee a VC yes. A term sheet. If I could, I’d be the one writing them. Nevertheless I do my best to help brilliant founders get funded. On the flip side, here’s what aren’t educated guesses, but guarantees. Or as close as one can get to a guarantee. A guaranteed no. An anti-playbook, if I might call it that. If it doesn’t help, I hope, at the very minimum, it provides you a few minutes of entertainment.
Not treating me as a human. This is less of a reason for me to get myself worked up. There are discriminatory, dismissive, bigoted people in the world. I get it. This is more of a problem for the founder when they’re looking to scale the team. Being a dick limits your ability to grow and/or empathize with the market. If you’re fine with treating me this way, then you’re definitely going to not bat an eyelid with other future hires, team members, investors, and customers. Equally true for any VCs/angels/investors out there.
Badmouthing others. This is more of a personal turnoff. We’re all intellectuals here. And it’s okay to have differing opinions of the world. But it’s not okay to talk behind others back. If you’re gonna badmouth others, I imagine the exact same for anyone else who gets on your bad side for whatever reason, including myself. Practice good social hygiene.
Complaining about your team/product. Complaining is a bit more nuanced. It’s fine from time to time, we’re human. I don’t expect you to be the perfect human, but a first meeting with me, as with any investor, is a first date. I want to hear about the bigger picture, the vision, the dream. Impress me. If you have time to complain during a 30-minute meeting, you’re probably not spending your time wisely. And if this is an intro meeting, you have yet to build up your social rapport with me to complain. Being frustrated about the market is fine. Being honest, introspective, and vulnerable is also fine. Your mileage may differ for the last part, but I love candid founders.
Lying. That goes without saying, if you’re lying about numbers or if I somehow find out that you are, then no. If you don’t know, you don’t know. If your numbers aren’t pretty, admit it. While I might not be able to help you get funded, I’ll do my best to help. If you don’t know something, admit it as well. And find out after. Going back to the earlier point, I love candid founders who have a bias to action.
Having an exit strategy slide. This is more true for larger $100M+ funds I send deals to. Having an exit makes sense for angels, and smaller funds, but larger funds need to look for fund returners and outsized winners, and an exit of XX/XXX million is not sexy at all.
Crazy, but not crazy and reasonable. This one is a new one, inspired by PG. It’s fairly rare, since I try to avoid putting myself in situations with crazy, especially cantankerous people. But it happens. If by any chance, you know your idea might err on the side of crazy, walk me through the logic of how you got there. Don’t just tell me “It makes sense to me” or “I know the industry better than you do.”
Lack of focus. It’s great if you want to do a million things, but saying you want to focus on everything means you’ll end up focusing on nothing. A lack of focus shows a lack of priorities. Focus and be able to back up why are you focusing on this at this point in time. I love Phil Libin‘s 4-year plan defined by one word for each year forward. You can find that plan here and here.
Asking for an intro without any context. “I saw you were connected with X on LinkedIn. Can you introduce us?” If that line pops up in the first 30 seconds of our first conversation, I’m running away. I need to know who you are, what you’re building, why it matters, and hell, why would this person you want to get introduced to is a good use of yours and their time. Build a relationship first. Don’t lead with the transaction. I am not an ATM machine. Neither are other people – investors or not.
Asking me to sign an NDA. Early on in my career, I admittedly signed a number of NDAs sent to me by founders. I love connecting brilliant people together, but if I have to get your permission each time I pass it to an investor or a potential advisor, it’s too much work for me. Frankly, I have other priorities. I get it; I’m a stranger. But I hope you can at least trust that I won’t run away with your idea or give it to a competitor. You have my word. If that isn’t enough for you, that’s fine. I’m just not your guy.
Asking the VC to do their work. “When we raise X dollars, we will do Y tasks.” I usually follow up on that statement with “What have you done so far to accomplish Y?” My least favorite founders are the ones who say something along the lines of, “We’ll worry about that when we get there.” Or “We were hoping our future investors will find someone for us.” We don’t expect you to know everything and everyone, nor do everything right, but we expect you to do some legwork to show you are learning. Show us that you’ve been scrappy, resourceful, and used what you had available to you.
Lack of self-awareness. “Where are you weak at?” If your answer is “Nothing” or “I’m good at everything”, that sends alarm bells to any investor. Which might also lead to a secondary question of “What do you need me for then?” A close cousin is one of my favorites: “What is your competition doing right?” If your answer is also “Nothing”, then you might need to do some market research and reconnaissance again. There’s a reason other customers are using your competitors’ and incumbents’ products. Find it out. On top of what they’re weak at. There’s a romanticized concept in Silicon Valley that every founder needs to be like Jobs with his reality distortion field. While it’s true you need to be able to help others see the future you’re seeing, you also have to deeply understand the realities of today of what’s stopping you from getting there.
Nothing’s changed since the last time we spoke. Investors invest on potential. A bet we make in a company is a bet that it has a chance to be as big as X tech giant in your space. Your ability to meet the demand in the market scales with the number of investment dollars in your company. That said, we expect movement. We expect deltas. And if your product really is inevitable in the market, you should be making progress with or without injections of capital. The latter, just at a slower pace. Venture capital is impatient capital. Also understand, 99% of businesses in the world don’t need VC dollars and operate incredibly well without venture investors.
You’re not obsessed about the product and the market. Building a scalable startup requires obsession. It requires you to lose sleep. You can’t just check out at 5 or 6pm. While I can’t measure that in the first meeting, a close proxy is how well you know the table stakes metrics of your business – net retention, CAC, LTV, growth, revenue, engagement rates – and more. In fact, obsessed founders usually tell me that they’ve already thought of and tried out the first 10 ideas I think of. Moreover they bring me back the results of their discovery. Obsession is contagious.
I have no idea what your product is or does. This is simple. If I walk out of our meeting and I still have no idea how to describe your product to others and why we need it in the world now, there’s no way I can confidently pitch your startup to the partners. Piggybacking off of the #14, if you’re obsessed about the product, you’ve told your story a million times and a million ways already. A few of which should have already resonated with select audiences. And even if it wasn’t to investors, you must’ve already told that same story to your customers. As a CEO/founder, you are the first and most important salesperson. In many ways, it means you have to push the sale. You have to get your customers to take action. I, admittedly, am a potential customer. A recipient of your sales strategy. And if I don’t get your pitch, it’s likely others might not as well. That said, for certain industries, like deep tech or biotech, I’m really, really dumb. So take my thoughts with a grain of salt.
This post was inspired by Jason Lemkin‘s blogpost, which I highly recommend checking out.
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In writing this blog, one of the greatest illusions I seemingly end up creating is that I know a lot. At least that’s what a handful of readers and friends have told me over the years. Truth is I don’t. And more often than not, I am learning and/or refining my thoughts as I am writing.
I’m gonna be honest. The script for this essay was going to be entirely different. In fact, I had exactly six hundred and eleven words written on another introduction to this piece. But in the past few weeks, I hit another seemingly insurmountable roadblock. Catalyzed by a conversation with a mentor who said: “David, you’ve confused movement with progress.” And she was right. The more I thought about it, the clearer it became. Snowballing upon itself until I realized how far I’ve gone when I mistook a compliment for an insult.
The more I read my previous intro, the more it sounded like total BS. Something someone would write never having experienced true self-doubt. I was my own harshest critic.
The irony of it all was that as I was interviewing other incredible individuals for the purpose of this blogpost, I felt I needed their advice below more than anyone else. In a way, I’m glad that some friends needed more time to collect and share their thoughts. In sum, this piece took me two months to put together. And every day, every minute, and every second was worth it.
As I’m writing this piece, I’m somehow reminded of a line Elizabeth Gilbert, author of Eat Pray Love, said in a 2016 interview with On Being, “Creative living is choosing the path of curiosity over the path of fear.”
The process
In concepting this essay, I spent more time than I’d like to admit beating myself up to get to the “right” phrasing of the question. And each time I thought I got closer to the “right” question, a day later, I would find myself second-guessing if people might even bother responding to a “lazy” question. A low-hanging fruit, so to speak. And the fallacy with a low-hanging fruit is that they’ve most likely been asked the same by others. Probably to the point of fatigue, paired with an eye roll. But the thing is… with the topic of self-doubt, it’s not a topic most people are comfortable sharing, much less in public. And equally so, are rarely asked a question on this topic. The flip side of the coin is that they too are less likely to answer such a question. In the end, I settled with a question I came up with two weeks prior.
Speaking on self-doubt, 25% of the people I reached out to in my existing network didn’t have time to respond. Another 20% refused within 24 hours. And another 20% agreed initially, but ended up refusing some time after the initial exchange.
In reaching out, I used a similar framework as I shared in my cold email template.
TL;DR: I’m writing a blogpost on self-doubt, and you were one of the first people I thought of in having been candid enough to share your life journey. What are some of the personal narratives, questions, or comments you find yourself regressing to when you’re filled with self-doubt?
The longer version: Recently, after sharing my own internal conflict (here and here), I had a number of friends and readers reach out to share their own struggles. With almost half of them mentioning at one point in time that “I wish I were like [insert role model’s name] because s/he seems to have it all down.”
But people, like you, are just as human and as real as the next person over. So, in my effort to use my humble platform to humanize the world around us, I thought you’d be one of the best to answer this question!
What are some of the personal narratives, questions, or comments you find yourself regressing to when you’re filled with self-doubt?
Because I also plan to share your answer in the form of a blog post, similar to a study I did last year, where I asked [names redacted] and some other great folks! By default, I will abstract your name from what you share. In this case, I will cite you as “[title]”. That said, if you’re open to me using your real name or would like a different “title”, please do let me know. If you’re curious as to why my default is not to include your name, this is why.
And I know your candor will help many more, like me, who are going, have gone, and will go through difficult times. So, thank you. I have nothing short of my deepest gratitude for not only your candor, your time, but also your willingness to share your thoughts with the amazing people in this world.
Warmest, David
My only ask
My only ask is that you stay open-minded as you read the below memoirs. For context, this has been the blogpost that I’ve gotten the greatest percentage and number of “No’s” from. In the forms of:
“This is not something I’m ready to share at this point in my life.”
“I’ve been too busy. Sorry.”
“I’m sorry. I don’t think I’ll have time to get to this.”
“I don’t think now is a good time for me to be involved unfortunately.”
It isn’t easy to share what each of my amazing friends have shared below. Some of which stories may never see the light of day without their courage. And I hope you let their authentic voice shine as much as, if not with more respect that you have given me all this time. On behalf of everyone here, thank you. Thank you for giving all of us the platform to share our most vulnerable selves.
Unless otherwise specified with their first and last name, the below names, listed in alphabetical order, are pseudonyms to respect the courage it took each and every one of them to share what they did: Andrei, Annie, Elijah, Harry, Liam, Lucas, Mateo, Mya, Stephanie, Zack
The question
What are some of the personal narratives, questions, or comments you find yourself regressing to when you’re filled with self-doubt?
“I have a rather conversational style of writing. I suspect it’s the product of some natural proclivities and the sheer joy that comes from clacking a keyboard.
“We live in a world where every action has the potential to be a performance. Performances, by their very nature, are meant to be judged—are they memorable? Funny? Heart-wrenching? All of us, whether we like it or not, are constantly on stage and constantly judged. Personally, I get stage fright, and don’t recall being consulted before I signed up for this part.
“My own vintage of self-doubt stems from being judged poorly by someone I need something from. I’m in a position of vulnerability, they’re in a position of power. An old turn of phrase from the Bible, later memorialized forever in A Knight’s Tale, captures what my psyche so desperately tries to avoid: “You have been weighed, you have been measured, and you have been found wanting.” The external “they think I’m lacking” becomes the internal “I’m not good enough,” and by then I’m well stuck in the swamp of self-doubt.
“For me it’s the idea of being rejected, rather than rejection itself, that causes self-doubt to metastasize. As the CEO of a venture-backed startup, this is not ideal.
“Two months back I had a bad panic attack. Wave after wave of self-doubt assailed me for hours after the attack subsided. Just yesterday, I had the minor upwellings of another one. Both were caused by pitches I knew I bombed (ironically, both investors ended up investing). In a perfect world, one in which I am preternaturally confident, the opinion of others shouldn’t stir feelings of self-doubt. In the real world, I care very much what others think of me.
“It’s easy to build stories in our mind to validate self-doubt, especially in the early days of a company when you don’t have a ton of evidence to beat back the self-doubt. I’m still not sure what the evolutionary advantage is to this pattern, to play devil’s advocate against ourselves, but it’s real nonetheless. We all do it. And the cleverer the mind, the more insidious the arguments.
“When this happens, my mind runs to something my dad used to say: ‘What you think about me is none of my business.‘ If I ever get a tattoo, it will be these 10 words. There’s something comforting, almost even glib, that enables me to turn the corner more quickly than I normally would. It’s a well-trodden path that leads me back to positivity, outcome independence, and abundance mentality.
“Self-doubt is inevitable. So rather than trying to avoid it, focus on leaving it behind.”
Of course, I couldn’t help but include Taylor’s afterword as well.
“Unintentionally mirrored after one of my favorite writers, John Gierach. John muses on life’s richest veins and uses fly fishing as his vessel.”
A blessing in disguise
“Self-doubt may feel painful at first sight… but in essence it’s a real blessing… because it helps balance one’s ego + falling for believing in their own shit! If you are trying to learn new things and explore uncharted territories… it’s inevitable to have self doubt. It’s almost like having a sense of danger when you are venturing in extreme sports let’s say.”
– Andrei, Managing Director at a VC Firm with 10+ Funds
Lily pads
“When I start feeling self-doubt, my mind immediately regresses to ‘lily pads’ or landing places of past memories where I feel like I could have done something better. I start to overthink everything I wish I could have done differently in past roles or interactions, and get paralyzed with fear that I will have the same regrets in the future based on the next choices I make and actions I take.
“Here’s a few questions I regress to:
How did I trick someone into believing I was the right person for this job?
Will I ever be able to match the level of success I had with a previous project or was that the ultimate cap of my success?
Do other people perceive a mistake I made in the past with the same level of intensity? Are they as fixated on it or was it something that barely registered for them?
“The things that have helped:
I think through the advice I would give a friend, and then I try to be as gentle with myself (which is a hard thing to do).
I remember that the best wins in life come from taking risks, and assure myself that if I don’t feel some doubt, then I am not pushing myself to grow.
I keep a folder of compliments and nice feedback I have received, and I go back and read through a few threads to remind myself I have been able to get through things successfully in the past.”
– Annie, Head of PR
I followed up with Annie after, if she could shed some more color on what advice she gives to herself, as well as an example of a compliment she finds herself revisiting when she finds herself wrestling with self-doubt. And here’s what she shared:
On self-advice,
“Look at your success over weeks or months, rather than by the hour. A single day may not feel like you’ve achieved everything you set out to do or landed a milestone, but if you can Zoom out, you are doing it right.”
On compliments,
“In response to a tough email I once sent, an executive privately emailed me to compliment my professionalism and how I had organized my thoughts. That compliment resonated because I had put hours of thought into that response even though it was only a few paragraphs long, and it meant a lot to me to have someone validate my thought process and my output. When I am doubting myself and worried my instincts are off, I go back to that email. I also try to put it into action and go out of my way to compliment people now in similar situations, because I know how much of a difference a one-line compliment can make.”
An old friend
“Self-doubt (SD) is especially bad when I’m starting a new project. My first company was deeply personal and mission-driven but required a lot of upfront capital (like most of my savings). I was always pretty good at hyping myself up to start the project but then the flashbacks would come. I begin to think of my mom and the 14hr shifts she’s worked since 2002. I had been working towards affording her an early retirement at the time and SD reminded me that it could all go away in a second.
“One wrong move and I would revert our family back to poverty.
“It would be on me.
“These thoughts left me sleepless, and also [made me] lose excitement in other parts of my life too. It sucked but having gone through it, I now consider SD a friend. Not a friend I’d want to hang out with all the time but an old friend with good intention and zero sugar coat.
“I can be a reckless person at times and can trust SD to be there to remind me that I have a lot to fucking lose.
“It reminds me to be very careful and to hustle like I have everything to lose.
“Whatever causes SD’s intervention these days, I realize it must be really fucking important to me and worth a second thought.”
– Mya, Forbes 30 Under 30 Founder
When you lose
“Say I lose my biggest client and I start to be overwhelmed with self doubt, my go to thoughts / comments / narratives are:
Am I delusional about my abilities? Maybe I’m actually an idiot with an ego? Imposter
What if I had done this, done that. Every little time I wasn’t perfect becomes a possible moment that will come back to ruin me
I’ve always been unlucky and luck seems to be a big part of success, so maybe I’m doomed no matter what
“But then there’s also a deeper narrative:
Maybe I just don’t ACTUALLY want this. I just think I want this. And my soul just isn’t in it and therefore I will fail. I’m not self aware enough
We all die. Nothing matters… especially me and what I’m doing.
A lot of successful people seem miserable. Is this a rat race? Am i setting myself up to fail on what really matters
Overall inability to identify a reason for why I am doing something and why I am the one that can do it”
– Elijah, Venture-backed founder
Self-compassion
“When I think about narratives, I try to go back to the psychology of ‘self talk’–especially when it comes to reducing ‘negative self talk’. Through time, self awareness and an emphasis on reducing self criticism, has helped me to become less doubtful. The question of ‘Why are you doing this?’, if done with self compassion can be a great way to maintain focus and inspire creativity.
“In terms of negative self talk day to day, I try to look at things through the constructive criticism lens, rather than the self critic. The former allows for more creativity. Life can be a challenge, and patience with the process helps me to embrace more self confidence.”
– Zack, General Partner at Venture Firm/Podcast Host
When Zack shared this, I couldn’t help but recall Jack Kornfield‘s line, “If your compassion does not include yourself, it is incomplete.”
What’s next
“Great question.
“I wish I could be of specific help but I do not do ‘self doubt.’
“I have had many many many challenges and course changes in my life, but each one of them created a new path. There are times when I am disappointed that my path doesn’t go in the direction.
“I had originally predicted or hoped for, but I can’t remember ever feeling self doubt. That’s because I always know I will discover the way forward that does work for me in the moment. I tend to focus more on the ‘what to do next’ rather than the ‘why something happened.’ I tend to be very stoic in my assessment and dealings with challenges. I don’t like feeling bad so I tend to create plans pretty quickly to move through whatever challenges I have.
“I do my best to recognize progress and change and do my best to adjust to it as fast as possible in order to minimize discomfort. I also tend not to think of things as either good or bad… just events that happen. The only thing I know I have control of is my response to change. I can’t control much… including the tempo of change. I tend to not look backward as to ‘why’ things happen and focus on ‘what’ I may have done to cause them as well as ‘what’ I am going to do next. In essence, I don’t feel like a victim ever… I own the events and challenges I face and do my best to strategize how to move through them.
“One easy example is this past year. My business model of being an in-person speaker got turned off like a light switch. I then just kept moving and building relationships. I believe the choice we have is to either keep up with the tempo of change in the world or not.
“Another example is happening right now. This past year I began walking a great deal and listening to audible books, taking notes and creating content. It was very enjoyable. I injured my hip a few weeks ago and it has totally disrupted my routine. I am working as quickly as possible to create new routines and healthy habits to continue to live what I believe is my purpose. It sucks that things change, but that is inevitable :)”
– Liam, Former FBI, Author
Personal suffering as a proxy
When talking about mental health, Max Nussenbaum, Program Director @OnDeck Writer Fellowship, always comes to mind. When I pinged him for answers, he gave me the opportunity to quote some of his amazingly candid essays.
“I wrote two pieces on this, one about being a startup founder and the other about being a writer.”
Both of the above pieces I highly recommend. But here are a few of Max’s thoughts that resonated with me the most. Even then, this snapshot will not do the nuance he describes justice:
“Since I didn’t know how to prove to myself that I belonged where I was, I turned to the only method I could come up with: treating my personal suffering as a proxy. The rest of my life becoming less and less put together must have meant that I was throwing more and more of myself into the company, and therefore that no one—least of all me—could question my commitment or whether I was cut out for this. And so I partied too much and foreclosed any real connection with the people I was dating and just generally reveled in everything around me being a bit of a mess.”
“A lot of this was fun, but I was stressed and anxious all the time; there was both a euphoria and a terror in feeling like my life was moving so fast that the whole thing threatened to go off the rails at any moment. I would look around and think to myself, this must be what really living is all about. And whenever I felt like an imposter as a founder, I’d use the corresponding messiness of my personal life as proof that I was giving the company my all.
“Of course, none of this made any logical sense, and none of it made us more successful. A stable relationship almost certainly would have been a support system that helped me be a better founder; at the very least, it’s hard to do good work when you were out till 4 a.m. doing drugs with strangers the night before. But that’s the thing: I wasn’t optimizing for actually making my company successful. I was optimizing for assuaging my own insecurities.”
Doing your best
“In short, I have a simple approach for when self-doubt could come in – in that, as long as you believe you are doing the best you can, getting support from others to help get through the situation, and striving to continually improve, then what is meant to be, will be. If it doesn’t happen, then it wasn’t meant to happen and something that’s better suited for you will come along in due time.
“While it might be short term disappointment, either turn it into a driving force to do better and achieve what you were originally trying to do, but knowing limits, putting in a plan for constant improvement and being satisfied with the achievements as long as you can internally reflect and know you did your best.”
– Mateo, Head of International at a post-Series B startup
Your best days are ahead
“I grew up in a poor, uneducated family, and have for a long time felt like I didn’t quite fit in. To them, my curiosity and intellectual pursuits are deemed futile and a pipe dream. It has also been met with ridicule and mockery. As much as I pretend that it doesn’t affect me, ultimately the people in your family have so much influence on our sense of self worth. It wasn’t until moving out here in 2013, that I felt like I found my family and my tribe. That narrative still bounces around in my head from time to time, but I have worked really hard through therapy and conversations with mentors to eradicate a good majority of it.
“I guess imposter syndrome, is the widely used term for this condition. For folks like us, that may be more deeply rooted and takes more effort to overcome. Am I smart enough to do this? Do I know enough? Am I experienced enough? I’m not educated like my colleagues. I didn’t go to Stanford, Cal, or MIT. What am I doing here?
“There’s only so much one can tell oneself to overcome these deeply rooted self doubts, ‘you got this’ ‘you belong here’.
“I have found that working through it is a journey that involves creating new habits and forming new narratives. Turning the negative self talk into, ‘this is part of the process’ ‘your beginner’s mind is an asset’ ‘I’m not my highly educated colleagues, but my game and perspective is unique’.
“Growing up in South Carolina in my family, so many of the things the could have been cultivated weren’t, and that’s fine. I feel like my best days are ahead of me, and I’ll take that.”
– Harry, Senior Design Leader at a Fortune 100 company
The war between results and doubt
“Whenever I go a month or more without a sale, the doubt starts to creep in. The only thing that pushes the doubt away is a successful sale. I am better at dealing with it now because I have been through so many cycles and ups and downs, but I have never truly figured out how to eliminate the doubt (or better channel/repurpose that negative energy) that creeps in whenever I have a little capacity to do more work.”
– Lucas, Managing Director at an Executive Search Firm
Would she say the same for a man?
As if the world gave me the sign to take this leap of faith to write this blogpost, the first person I reached out to was Stephanie. I happened to catch her right at the moment she had been rejected after an interview for a senior position at a firm.
“I was honest about my career and life. Next time I could speak differently but I know with my resume and the time off I took that I would get the questions I received.
“I just hated the comment she made. She was very complimentary but then used this word that made me wonder, ‘Hmm would she say this about a man with my same career path?’
“The interviewer commented to my friend that I was smart but ‘too whimsical’ for the role they are hiring for. It made me question my whole career path for a second. By the way, I had never been called ‘whimsical’ before… that’s a word used for fairies.
“I try not to overstress myself and that’s why my personality is more chillax, but I take myself very seriously at work.
“Questions I ask myself and messages I give myself when I have doubt:
‘Am I doing the right thing with my life?’
‘What can I do to help others understand why I am taking this direction?’
‘How can I be my number one fan?’
‘Be compassionate with yourself.’
‘Focus on your mental health during this time of self doubt.’
(when someone rejects me)”
– Stephanie, Female co-founder of a hedge fund and advisor to multiple companies
Dreaming and falling
“From my own experience the question of self-doubt sneaks in way too often in almost any entrepreneurial quest. It can happen that you have self-doubt 101 times a day about some totally banal things such as ‘can I name myself a CEO and put it on my LinkedIn profile if I just founded a business’.
“For me personally, those ‘light’ self-doubt questions are categorized more as decisions. Same as with food, just make up your mind on what you want to have for lunch and stick to your decision whether it tastes or it doesn’t taste good. And of course, if it did not taste well enough, make sure that you have learned the lesson for the next time.
“The real heavy self-doubt comes to surface when:
A. You are selling a dream, a vision or an idea, and B. When things are falling apart.
>> A.
“In situation (a), it can often happen when you don’t have enough pieces of tangible evidence, data points, intelligence, etc. to prove your point of view to yourself and others. People will say – your idea sucks, this is impossible, you don’t have the skillset, your team is not good enough, the market does not exit, etc.
“To ‘survive’ these situations and be able to thrive no matter the negative comments and feedback (which often can come from some of the most influential and successful investors and entrepreneurs), I always make sure that before I go out there selling my vision, I truly believe in my idea/dream and that I have done enough homework to personally assure that there is a decent chance for it to come to life. I bulletproof it for myself first before I take that and test it with the world.
“Moving forward with selling the dream, during the conversations I tend to come back to the narratives of others who did something great in the past and proved others wrong.
“As Nelson Mandela would say, ‘It always seems impossible until it’s done.’
“I read so many inspirational stories of successful innovators, scientists, philosophers, artists, sport athletes, and entrepreneurs. And I don’t hesitate to bring those examples up in a conversation to show that someone has done it before even though at the beginning no one recognized their potential or the potential of their idea.
>> B.
“For situation (b) when your project is failing, sometimes it is totally out of your hands (and that is sort of an easier scenario,) but sometimes you do tend to question yourself if you could have done something differently. You start developing self-doubt in your managerial and entrepreneurial competence. Especially when you read so many headlines about the success of other entrepreneurs that raised 100s of millions or exited their companies at some mind-boggling valuations.
“In those moments, I do two things:
I rationalize by going back in the past and rewinding all the small achievements we made along the way. While doing that, I express deep gratitude for every single small step I made. As an example, we never raised from a Tier 1 VC but we met a lot of them and with some, we had multiple rounds of conversations. I am deeply grateful for even hearing back from them, for every moment they took to review my deck and learn more about our project. Success is the path and the process itself, not the final outcome. And that is what I remind myself of, in case the self-doubt comes to surface.
I ask myself if I did put in my perfect effort because that is all I could have done. As Sam Altman said, one needs a great idea, a great product, a great team, and great execution. Even if you have all four of these you may still fail. The outcome is something like idea x product x execution x team x luck, where luck is a random number between zero and ten thousand. Knowing that at the end of the day we are only in control of our thoughts, intentions, and reactions I end up asking myself – am I a satisfied with my input and work and did I do my best and put in the perfect effort? And the answer to that question brings me to a rationale that is beyond self-doubt and is actually the basic building block of self-confidence. This really helps to turn doubt into a strength!”
I know that not every story will resonate. Some may never resonate. Some will grow on you over time. Others will find meaning into your life when you least expect them to. My purpose for starting this blogpost is to freeze these stories and life lessons in amber for when you find yourself needing them the most. Life’s not easy. Neither is it meant to be. But hopefully, you’ll find comfort knowing you are not alone.
At the end of the day, all advice is autobiographical. Or as Kevin Kelly, co-founder of WIRED magazine, once wrote, “Advice like these are not laws. They are like hats. If one doesn’t fit, try another.” What you’ve read above are the advice, stories, autobiographies. Anecdotes that hopefully shed more light into the elements of humanity many of us, including myself, have been scared to talk about.
A good buddy of mine made me watch a movie recently. It couldn’t have been more timely. He told me nothing more than this one line from that movie:
“We are all the unreliable narrators of each other’s stories.”
So I watched it. I won’t tell you the name of the movie or what it’s about, but if you use the above quote in your search query, you’ll find it. And if you’re like me, and so many others, who struggle with identity and your place in the world – either now or in the past, it’ll change the way you see the world and the people around you.
Thank you Taylor, Max, Janko and everyone else who made this piece possible!
#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!
