An old college friend reached out to me not too long ago and asked me if I had any tips to share on getting a mentor. And the first thing I responded with is: “Don’t ask people to be your mentor. In fact, don’t even mention the word mentorship.”
You see, mentorship is a loaded word. It comes with baggage. Centuries of it. Hell, millennia of it. And apparently, dating as far back as 3,000 years ago to Homer’s Odyssey. Mentorship comes with an expectation of commitment. While that amount of commitment differs per person, a mentorship ask from a stranger is an amorphous expectation of time and energy from a busy person who likely has a laundry list of other priorities. Without any precedence or context, it’s hard to make that decision with asymmetric information.
The best pairs of mentorship have always been a two-way street. It takes two to tango. If we were to take the equation of a line:
y = mx + b
… a mentee wants a mentor whose current b, or position and experience level in time, is greater than their own. A mentor wants a mentee whose m (rate of learning, iteration, and hustle) is as great or greater than their own. The bet is that at some point in the future, at least in my experience, mentors would like to learn from their mentees as well, and/or see it paid forward.
Yet, I see so many mentees out there who discount their own value in the relationship. One of my mentors shared with me a few years ago that the older you are, the younger your mentors should be. And I’ve carried that in my heart ever since. More recently, I found that line in the form of a tweet from Samir Kaji.
Was at a VC quarterly meeting today and the topic of aging out in VC/tech came up (which I think is BS)
Their response on how they stay fresh in mental models was around the thinking of "the older you get, the younger your mentors should be".
I can’t claim to have mentored tons of folks, but I also realize both from anecdotal experience and talking with my mentors that the best thing about mentorship is the feedback. That the mentors learn about the result of their advice as an opportunity to finetune their own learnings.
Take for example, my office hours. Of the hundred or so people I’ve met through open office hours, I’ve probably shared the same piece of advice at most five times. It gets even more interesting when you consider that the vast majority of people I’ve met via office hours come for fundraising advice. Somewhere in the ballpark of 80% of people. While there are similar thematic questions I ask people to consider, the best advice is tailored to every unique situation. That said, my advice, like any others’, starts as a product of my own anecdotal experience. A sample size of one. And as we learned in Stats 1 in high school or college, that’s a poor sample size. So, one of the best ways for me to refine my own learnings is either:
Act on it again and again. But there are some things in life I can’t do again. For instance, high school or freshman year of college or my first job. Those are experiences entombed in amber that unless I had a time machine, they’re one and done.
Learn how other people execute on that advice and what resulted of it.
One of the many joys of writing this blog is that every so often a kind reader reaches out to me and shares the results of them implementing the thoughts I’ve shared here. Then they let me know I’m either full of s**t or I drastically helped them grow. And I love both forms of feedback equally as much. After all, it’s the rate of compounded learning that helps me mature — even if it’s outside of my own anecdotal experience. Feedback and learning of others’ results gives me a sample size greater than one. The same is true for other mentors, advisors, and investors out there.
So, what does that mean tactically?
Start with the ask.
There’s a metaphorical saying in the world of venture that investors invest in lines, not dots. They want to see progression rather than stagnation. So in reaching out to anyone you’d want to learn from, don’t lead with “Can I have 30 minutes of your time?” Instead, lead with a question. Why are you reaching out? What question can only they answer?
So, that means, “should I get an MBA?” is not a good question to ask. It’s generic, doesn’t contextualize the question, and you can figure out how to do so on the internet. On the flip side, a better question would be: “I saw that you graduated from Wharton before breaking into VC. So I’m curious, did you always know you wanted to be in VC, or was that something you discovered in B-school? And what experiences did you gain in B-school that set you up for VC?”
Moreover, show you’ve spent time in the idea maze before proposing the question to the person you want to learn from. “I’ve read about X and Y, and have thought about or tried A and B already with these results. But the question still gnaws at me.”
Why does this contextualization matter? One, it gives that person context to better answer your question. Two, the last thing any person giving advice wants is for their advice to dissipate into the cosmos. For their advice to go to naught. And if you show that you’ve spend blood, sweat and tears already pondering the problem, then you’re more likely to take their advice seriously. In effect, their advice will be a lot more meaningful. And, chances are you’re going to be a lot less whimsical than the average person asking for their time. Use someone’s time in a way that won’t feel wasted.
Follow up even if they ghost you.
If they respond the first time, great. And if not, don’t give up until you’ve sent at least three emails. If they don’t respond the first time, they just might not have seen it. If they don’t respond after the ninth email, they’re just not interested.
And with each email follow up, tell them when you plan to follow up since you assume they’re busy. “If you’re too busy, I completely understand and I’ll follow up in two weeks.” On the last email if no response, thank them for their time and wish them well.
Don’t set recurring meetings (initially).
First of all, it’s a heavy ask to anyone — stranger or not. Second of all, there’s no promise that their time (and your time) won’t be wasted. Third, do you even have that much to ask about? Most of the time, you don’t. What you think you want and what you actually need are usually very different. It’s an iterative process.
Instead, start with a single question. Ask it. If they’re free for a meeting, set 20 minutes (here‘s why I like 20, instead of 30). If not, get their thoughts asynchronously. Get advice. Act on the advice (or not, but be intentional if not). The most important part is to share your results with the origin of that advice.
So, when you close out that initial meeting, ask if you can reach out to them 24 or 48 hours later after you’ve had time to mull on it or act on it. Timeframe will vary. And if you do follow up shortly after without results, limit any additional ask to 1-2 questions, max. Ideally it should take them 2-3 minutes to respond to. For any advice that takes a longer feedback loop, set a time in the future (two weeks, a month, 2 months, etc.) later to reach back out to share your learnings. And sometimes, that means you didn’t implement their advice. Why not? What did you learn from doing the counterfactual?
When you reach back out to share your learnings, see if you can jump on another 20 minute call, or shorter. And get their thoughts on the facts. Possibly get more advice. And do that again and again. Until at some point — my litmus test is usually 3-4 of these discrete exchanges, in no particular frequency —, I ask if we can get something recurring on the calendar. Nothing long. Stick to 20 minutes. And set an end date for the recurring nature. I usually do 4-5 times as the first run through.
At the end of those recurring meetings, be honest and mutually evaluate: Was it a good use of everyone’s time? If not, end it, but reach back out periodically to share your thanks, especially around the holiday season. If it does work, set another set of recurring meetings and reevaluate again in X time. And voila, you have yourself a mentor (in the traditional sense).
One more note on this… if that person is extremely busy and you know they are, sometimes a more personal touch to the email is recording a Loom and asking your question in front of a camera to that person in particular. For any Loom video, I wouldn’t go over a minute of recording time. Keep it concise, and use text to describe everything else.
Build a platform where they can share their advice with others.
Either start a podcast or a blog. Or help them find an audience that is outside of yourself —a fireside chat, a club, a non-profit, posting a Twitter thread or LinkedIn post, and so on. Their time is limited, and if they’re likely to give that same piece of advice to many others, help them find the tribe of people who are willing to listen to their advice. So instead of their advice being one-to-one, it’s one-to-many. In sum, a larger impact radius.
Of course, the caveat here is if the advice you seek is personal experience that isn’t suited for a stage, then don’t do it.
In closing
Some of the mentors I have today are folks I’ve known for years, but neither of us remember the discrete date in which it all started. Simply put, “it just happened.” There are others where we’ve never explicitly said we were mentor and mentee. Yet, I learn just as much if not more than if I had explicitly asked for mentorship. The same is true for some of the “mentees” I have.
At the same time, I wouldn’t discount the fact that you can truly find mentors everywhere in your life. Too many people focus on only finding strategic mentors, but fail to see the value in tactical and peer mentors, which I wrote more about three years back.
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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
There’s this distinct memory I have from when I was 11. It was the second to last day of sixth grade – somewhere in the middle in the sweltering ’08 June heat. Despite efforts to hold them back, it was the first time in a long, long time that I cried in public. On a day when everyone was obsessed with signing yearbooks and bragging about summer vacation plans, my core teacher, Mr. S called one of my classmates and I up to his desk.
As soon as I realized his usual smiling demeanor was nowhere to be found, I knew something was very wrong. It turned out that my classmate had submitted the exact same final project as I did – one that I had painstakingly created over two months to be what I believed to be the most ingenious final project my sixth grade teacher would have ever seen. I don’t remember who that classmate was. Hell, I don’t even remember if they were boy or girl.
Between salty tears and choked hiccups, “She… she cop-… copied me,” I stuttered to Mr. S.
All I remembered was that the next few minutes flew by in a watery blur trapped above the floodgates beneath my eyes. I failed to hear a single word he said. I just stood standing facing the beige walls behind Mr. S’s desk. He pulled my classmate to the side to a conversation I was not privy to.
As time went on, my eyes drifted further up, hoping gravity would be kind to my waterworks today, until I was staring right where the west wall and ceiling met. And right on that horizon, I saw the words he hung against that beige wall since the beginning of the school year. A meme. Borderline, a dad joke.
Opportunity is now here.
But the ‘w’ and ‘h’ were so close together, when I first walked into Mr. S’s classroom, I thought it read: Opportunity is nowhere. When I asked, he once told me, “You know there’s a fine line between opportunity and lack thereof.” In a chuckle befitting of a dad, he continued, “The only difference is that you have to give yourself some space.”
And for the briefest moment, I remembering smiling just a little then.
After chatting with my classmate for a few minutes, they solemnly walked back to their seat and sat down. He beckoned me over, and waited a few seconds so that my sniffles wouldn’t drown out his soft, but firm voice.
“David, you should be proud [she] copied you. That means you have something worth copying.”
To this day, that line stays in my head rent-free.
Interest is a two-way street.
Eight years later, after crafting the perfect cold outreach email to someone I really respected, I received the most meaningful rejection email to date from her. Just four words. “Be interesting and interested.”
In fairness, it took me a few weeks before those words clicked, which I wrote about here. I was definitely interested in her background, but I hadn’t given her any reason to be interested in me. I wasn’t interesting. Or at least, I hadn’t painted myself to be an interesting person.
Interest comes in many forms. The ability to be useful. Being a host of exciting or inspiring stories. Strategic value. Bragging rights. Simply put, you need to have something that people want. They either want something from you, or they want to be like you. In Mr. S’s words, “something worth copying.”
Of course, maybe there’s a world where you don’t want people to know. For instance, Max Levchin once shared in Founders at Work. “If you patent [software], you make it public. Even if you don’t know someone’s infringing, they will still be getting the benefit. Instead, we just chose to keep it a trade secret and not show it to anyone.”
Or you might make your VCs sign NDAs. Which most of us aren’t a fan of.
In closing
If there’s anything you take away from this essay, it’s that:
I used to be crybaby, and
Have something worth people’s time and interest.
It doesn’t matter if you’re copied. Hell, it’s good that you’re being copied, or that there are similar ideas in the market.
At the end of the day, it’s not about the idea; it’s about execution. No one can beat you at being you. Do things that excite you. Do things that, if you were someone else, you would want to hang out with you.
Don’t ever have someone you meet with feel like they’ve wasted their time. Rather, make them feel like they got time back from meeting with you. That’s when you feel the magnetic pull of the people around you. And that’s when the people you want to meet and learn from will want to learn from you.
I’m once again reminded of two quotes. One of my recent favorites.
“Magic is just spending more time on a trick than anyone would ever expect to be worth it.” – Penn & Teller
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!
Any views expressed on this blog are mine and mine alone. They are not a representation of values held by On Deck, DECODE, or any other entity I am or have been associated with. They are for informational and entertainment purposes only. None of this is legal, investment, business, or tax advice. Please do your own diligence before investing in startups and consult your own adviser before making any investments.
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!
One of the most common questions I get from first-time founders, as well as those outside the Bay Area, is: “Who is/How do I find the best investor for our startup?” Often underscored by circumstances of:
Raising their first round of funding
Finding the best angel investors
Doesn’t have a network in the Bay Area or with investors
While I try to be as helpful as I can in providing names and introductions, more often than not, I don’t know. I usually don’t know who’s the best final denominator, but I do know where and how to start. In other words, how to build a network, when you don’t think you have one. I emphasize “think” because the world is so connected these days. And you’re at most a 2nd or 3rd degree connection from anyone you might wanna meet. Plus, so many early-stage investors spend time on brand-building via Medium, Quora, Twitter, Substack, podcasting, blogging, and maybe even YouTube. It’s not hard to do a quick Google search to find them.
“Googling” efficiency
While I do recommend starting your research independently first, if you really are stumped, DM me on my socials or drop me a line via this blog. Of course, this is not a blog post to tell you to just “Google it”. After all, that would be me being insensitive. Here’s how I’d start.
One of the greatest tools I picked up from my high school debate days was learning to use Google search operators. Like:
“[word]” – Quotes around a word or words enforces that keyword, meaning it has to exist in the search items
site: – Limits your search query to results with this domain
intitle: – Webpages with that keyword in its title
inurl: – URLs containing that keyword
Say you’re looking for investors. I would start with a search query of:
Feel free to refine the above searches to “angel investors” or “pre-seed funds”.
Landing and expanding your investor/advisor network
I was chatting with a friend, first-time founder, recently who’s gearing up for her fundraising frenzy leading up to Demo Day. She asked me, “Who should I be talking to?” While I could only name a few names since I wasn’t super familiar with the fashion industry, I thought my “subject-matter expert network expansion” system would be more useful. SMENE. Yes, I made that name up on the spot. If you have a better nomination, please do let me know. But I digress.
First, while you might not think you have the network you want, leverage who you know to get a beachhead into the SMEN (SME network) you want. Yes I also made up that acronym just now. But don’t just ask anyone, ask your friends who are founders, relative experts/enthusiasts, and investors. Ideally with experience/knowledge in the same/similar vertical or business model.
Second, if you feel like you don’t have those, just reach out to people who are founders, relative experts/enthusiasts, and investors. Via Twitter, Quora, LinkedIn, Clubhouse. Or maybe something more esoteric. I know Li Jin and Justin Kan are on TikTok and Garry Tan and Allie Miller are on Instagram. You’d be surprised at how far a cold email/message go. If it helps, here’s my template for doing so.
Then you ask them three questions:
Who is/would your dream investor be? And two names at most.
Or similarly, who is the first (or top 2) people they think of when I say [insert your industry/business model]?
Who, of their existing investors, if they were to build a new business tomorrow in a similar sector, is the one person who would be a “no brainer” to bring back on their cap table?
Who did they pitch to that turned them down for investment, but still was very helpful?
For each of the above questions, why two names at most? Two names because any more means people are scraping their minds for “leftovers”. And there’s a huge discrepancy between the A-players in their mind and the B-players. Then you reach out/get intro’ed to those people they suggested. Ask them the exact same question at the end of the conversation (whether they invest or not). And you do it over and over again, until you find the investor with the right fit.
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!
If you’re a regular on this blog, you’re probably no stranger to my essays on cold emails – whether it’s my cold outreach mental model or lessons from replying to spam emails or how I write longer cold emails as opposed to shorter. Yet, I recently realized I’ve shared my thoughts on the pre-game and the game itself, but I’ve yet to write on the post-game. So this essay is dedicated to exactly that. What do you do after you send that initial cold email?
The short answer: If you want to stand out, always follow up. To quote my good friend, Christen on her TikTok, where she shares amazing soundbites of career advice and networking.
The longer answer
I met a founder once who emailed an executive at Disney every business day for almost one year, minus ten days. The caveat is at the top of every daily email he wrote, “If you want me to stop, I will.” Almost a year after he began, the executive took the meeting. And Disney is now one of this startup’s biggest customers.
I met another founder a few years ago, who retweeted tweets from a Forbes’ Midas 100 VC every week for three months, while including his own constructive commentary each time. So, when this founder began his fundraise three months later, this VC set up a meeting with that founder within two hours of the cold email, first thanking the founder for his thoughts over the past few months.
Garry Tan and Apoorva Mehta have bothshared this story publicly. Apoorva, founder of Instacart, back in 2012, wanted to apply to Y Combinator. Unfortunately, he was applying two months late. So he reached out to all the YC alum he knew to get intros to the YC partners. He just needed one to be interested. But after every single one said no, Garry, then a partner at YC, wrote: “You could submit a late application, but it will be nearly impossible to get you in now.”
For Apoorva, that meant “it was possible.” He sent an application and a video in, but Garry responded with another “no” several days later. But instead of pushing with another email and another application, Apoorva decided to send Garry a 6-pack of beer delivered by Instacart. So that Garry could try out the product firsthand. 21st Amendment’s Back in Black, to be specific. In the end, without any precedent, Instacart was accepted. And the rest is history.
So, what is the common thread here?
As my friend once told me, “It’s not hard to be persistent. Most people can easily be. But most people aren’t persistent AND considerate.” Persistence is keeping your promises to yourself. Being considerate is respecting and keeping your promises to others – explicit and implicit. Explicitly, if you say you’re going to do something, do it. Implicitly, understand the social context, their schedule, their cognitive load. One of the lines I always add at the bottom (or sometimes at the top) of my cold outreaches:
“I know you get a hundred emails a day, and if you don’t have any time to respond, I completely understand.”
To take that one step further, sometimes you’re reasonably confident they won’t have time to respond. Big life or career events may make it hard for them to respond, like:
New baby/paternity/maternity leave
New publication
Recently did a (podcast) interview
Released some version of viral content (i.e. YouTube video, TikTok, Clubhouse, Twitter, etc.)
Founder raising a new round
Upcoming product launch they’re a key player in
VC raising a new fund
Shit hit the fan
Anything else the press is actively writing about
If that is your assumption, I add in one more line:
“If you don’t have time to respond, I’ll follow up one week [or whatever other timeframe] from today.”
And once you’ve said it, do it. To save you the time to draft up a follow up email a week later, a hack I use is to just write that follow up email as soon as you send the first email. Then schedule it to send a week from the day you sent the first. Make sure that each follow-up email isn’t the exact same. Show updates on what you learned, found, or thought about, as well as additional value to the person you’re reaching out to. While this hack is the bare minimum of what you can do to follow up, this should never be the ceiling. 9 out of 10 times I find myself going back, cancelling the send, updating the email with my learnings, then re-scheduling it.
Follow up at least twice after you send the initial cold email. But be understanding of their circumstances. And of course, never overstay your welcome. Understand the difference between a soft “no” and a hard “no”. In the circumstances of a soft “no”, recognize the variables that led to it. And reach back out when those variables are not in play, or to your best guess.
In closing
I met a brilliant founder years ago who, at the time, scaled his business to 100 employees, and he told me something that resonates with me till this day. “You can only learn from experience, but it doesn’t necessarily have to be yours.” Though I learned of his saying a few years after, it summarizes why I started my 6-year at least once a week cold outreach streak. To learn vicariously through others’ experiences. And if that was and is the impetus, it’d be a shame if I didn’t see it through to the best of my ability. ‘Cause if I was gonna give up after just sending one email, why start?
As Ron Swanson once said, “Never half-ass two things; whole-ass one thing.” So if you’re gonna start with the first email, you might as well send the next two. If the first shot doesn’t swish, catch the rebound and shoot again. Persistence. And ideally rebound thoughtfully.
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!
Proportionally speaking, I rarely make referrals and intros. Numerically speaking, I set up more intros than the average person. Frankly, if I made every intro that people have asked of me, I’d be out of social capital. It’s not to say I’m never willing to spend or risk my social capital. And I do so more frequently than most people might find comfortable. In fact, the baseline requirement for my job is to be able to put my neck on the line for the startups I’m recommending. The other side of the coin is that I’ve made more than a few poor calls in my career so far. That is to say, I’m not perfect.
I only set up intros if I can see a win-win scenario. A win for the person who wants to get introduced. And a win for the person they will be introduced to. The clearer I can see it, the easier the intro is to make. The less I can, the more I look for proxies of what could be one.
This largely has been my framework for introducing founders to investors, as well as potential hires, partners, and clients. Over the years, I realized that I’ve also been using the same for people who would like an intro to someone above their weight class.
Below I’ll share the 4 traits – not mutually exclusive – of what I look for in world-class founders.
Two and a half weeks ago, I wrote about my mental model for confronting fear – the art of running into walls. Inevitably, I’ve had more conversations about fears and how to overcome them since then. And in those moments, I was reminded of a question Seth Godin posed on his recent appearance on The Tim Ferriss Show. Most people ask the question: “What would you do if you could not fail?” And subsequent answers led to wild dreams, achieving the impossible, and often times, still not a step closer to achieving that dream, myself included. I wanted to be an astronaut, a pilot, an Olympic medalist, and more. Instead, Seth posed the counter: “What would you do if you knew you would fail?“
Knowing that I’d fail
Seth cites that most marathoners competing in the Boston Marathon do not aim to win, yet they still do it. Similarly, I work with founders knowing that most will fall short of their dreams. If we’re talking about expected value – the sum of all the dollar size outcomes of each possibility, multiplied with their respective probability of occurring, then:
E(Vstartup success) << E(Vmost other career paths)
Rationally speaking, the career of a founder is not designed for success. But hell, it’s the irrational founders who do find it. Against impossible odds.
But why?
Why still pursue a career when the odds aren’t ever stacked in your favor?
On the same token, why participate in any contest if you know you’re most likely going to fail? And, I mean contest in the most liberal sense here. Just like a marathon is a contest of endurance and physical prowess, building a startup is a contest of capital, time, and social impact. Confessing to your crush is a contest of love. Sending a cold email is a contest of attention. The more saturated the market – the contest – the more likely you are to fail.
How to Win
In winning, I focus on only one question: What will I gain in this pursuit that’s independent of the result of the contest?
Running a marathon proves that I can push my body beyond its limits.
Confessing to my crush gives me resolution to move on in my life.
I work with startups to build friendships and acquire skills that will transcend the dollar value of the venture. People who are ambitious typically learn fast, and will try again and again until something works. If not this idea, then the next. If not today, then tomorrow. And, if not tomorrow, then the day after. It’ll only be a matter of time before preparation meets opportunity. It’s why we call startups 10-year overnight successes.
So when I take on a new endeavor even outside the exciting world of venture, I look for where there will be a net positive in my life and the world around me, on 3 fronts:
The relationships/friendships I will build along the way,
The skillset I will develop and/or hone,
And the impact the process will have in the lives of other people, particularly my friends and family.
If the above function has a positive first and second derivative, then I know I will win even if I lose.
#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!
There’s a saying in venture that: “A-players hire A-players; B-players hire C-players.” Your ability to grow a business is often closely correlated with your ability to attract and acquire talent. But what does it mean to attract and hire world-class talent? Especially for functions you, as a founder, yourself may not be an expert in.
“A-players hire A-players; B-players hire C-players.”
How does a first-time founder how to vet a seasoned sales executive? Or on the flip side, how does a non-technical founder learn to differentiate a good AI engineer from a great AI engineer?
While even the best founders, leaders, and managers make hiring mistakes, hopefully this post can act as a reference point as to what to look for. And while I have yet to master the craft, I’ll borrow 5 lessons from some of the best that has served as a guiding principle for me and for some of the founders I’ve worked with.
5 Lessons from 4 of the Greatest
Hire passion; train skill.
Desire/obsession > passion.
And, the ephemeral nature of passion.
Hire VPs who can hire.
Attract and hire intentionally.
On building trust.
On scaling yourself.
To hire your best complements, ask people in your network 2 questions.
I recently tuned into, at the time of writing this post, Tim Ferriss’ third most recent podcast episode, interviewing Rabbi Sacks. Although I’m a regular listener to the show, I wasn’t expecting much. I neither have a history of being religious nor spiritual – merely peripheral curiosity. Yet, I don’t hesitate for one second to say: It is, by far, one of the most insightful and enlightening podcast episodes I’ve heard in 2020. So, if you have a spare 1.5 hours, I highly recommend it, especially if you’re looking for a perspective shift on:
Leadership,
Seeking peer approval,
What a single cold “call”/visit could get you,
And the need for “cultural climate change” in the understanding between the balance of “I” and “we”.
And Rabbi Sacks masterfully weaves these concepts together. While my reaction will never do his insights justice, two other thoughts, each paired with their own story, I had to double click on:
“Good leaders create followers, great leaders create leaders.”
“What happens when you’re in a situation in which you have done something that has generated widespread disapproval? How do you deal with that?
“Win the respect of the people you respect.”
And I digress.
The Bubble
I’ve lived my entire life so far in the Bay Area, barring a few vacations and excursions here and there. I was born here. I went through 12 years of grade school here. 13 if you count kindergarten. And though I had the option of leaving the Bay for college, I ended up choosing a school here as well. Truth be told, I might as well have “Made in the Bay” stamped on my forehead.
I live in a bubble. But I know I breathe in one. Not just geographically, but educationally, racially, sexually, socioeconomically, and so on.
Being a shy introvert pre-adulthood didn’t help with broadening my perspective on life either. I still remember the days in high school when I dreaded the teacher calling on me. Clammy palms, cold sweat, rigid spine. I would never vocally question disagreement. Equally, I would rather be a people pleaser than cause what I deemed to be unnecessary friction. I was a seafood hors d’ouevres of perturbation.
So, by inspiration from a mentor, I took actionable steps to conquer my own demons. Meet one new person you’re extremely excited to meet every single week for a year.
While I still carry the artifacts of myself yesterday, learning to balance myself between the person I thought and think I needed to become and the person I was, I began my journey 6 years ago.
The Pop in the Bubble
I’d be fronting if I said I wasn’t scared shitless when I began. Though I don’t think everyone in the world has this dilemma, I’m confident I am not alone. I had and have all these scenarios playing in my head. A bunch of ‘what-ifs’. What if they think I’m too nosy? What if they don’t have time to respond? Or what if they hate me for bothering them?
They say it gets better over time. And they’re not wrong. But I still have that lingering, gnawing feeling whenever I click send or put myself out there. While, over the years, the fears never fully dissipated, I’ve learned to tango with discomfort. In the words of my mentor who inspired my journey:
“You’re never as good as they say you are, but you’re also not as bad as they say you are. And hell, you can’t even be bad if they don’t even know who you are.”
… which I believe he drew inspiration from Lou Holtz. Shortly after, I clicked the “Send” button at the bottom of my first ‘curiosity’ email. After all, like he said, what’s the worst that can happen? Getting ignored. And as such, I would be no better nor worse off than I was and am in that cross section in time. With that assurance, it eventually led me to find my cold email “template” and hosting social experiments, like Brunches with Strangers.
The Where
Over the past few weeks, a few new people asked me: “Where do you find these people to reach out to?” Although it’s not the first and I assume certainly not the last, I thought I’d share in the form of this post as a possible inspiration for how we can grow, if I were to paraphrase Rabbi Sacks.
While I don’t characterize myself as a voracious reader, I allot time every day and have found many of my Senseis in the form of literature and discourse – online and offline, printed and taped, and in-person and remote. Including:
Books
Online articles/press releases
Newsletters
YouTube videos
Movies
Podcasts
Webinars/fireside chats
Textbooks
And, other people
One level deeper
To look beyond my own horizon, I tune into Pocket‘s Discover tab, or a platform I’ve recently fallen in love with, Readocracy. You can check out what online reading I’ve been up to lately on my Readocracy profile. And I can’t wait, when I can start tracking the books I read and the podcasts I listen to on there. I’m also fortunate enough to have friends who read, write, listen, and socialize with different social and professional circles than I do and am in. And as I meet more people, the spectrum of topics and interests snowball upon each other, as we help each other see new perspectives – some of which we never thought were possible.
Admittedly, where I find who to reach out to is, by no means, special or esoteric. In topics, I look into ones I’m genuinely interested in, in that moment and predictably beyond, even if it’s only a month or two, as promiscuous as I might be for many. In my short phases of promiscuity, I nevertheless take deep dives. Deep, yet often, not long. At the same time, I have a small handful of evergreen interests, like:
The art and science of building relationships,
The art of creating irreplaceable memories,
Psychology and mental models,
Swimming and intense athleticism,
Art as a multi-faceted definition,
Startups,
Technology and what lies at its frontier,
The final frontier – outer space and its cosmological inhabitants,
And the future.
In people, I look for two things:
Inflection points in their life. Oxymorons/ironies. Overt and covert contradictions.
If I were to make assumptions given their initial attributes (i.e. education, age, gender, geography, career, life choices/circumstances, etc.), would I have been able to predict where they are now?
Of course, in making these assumptions, it is also my responsibility to be aware and to tread carefully where I should. Unfortunately, ignorance is not an excuse. If I’m unsure, I err on the side of caution.
Deep intellectual curiosity and passion. Whom I call the passionately curious and the curiously passionate.
In closing
While I’m prone to talking too much at times, during these moments, it is my duty and the highest form of respect I can offer, to listen. If I were to take it from a selfish note, I learn so much more when I listen. And in actively listening, and actively checking my biases, to respond with thoughtful questions.
So, I’ll close on more thing Rabbi Sacks said in his recent interview with Tim Ferriss:
“Safe space means that courteous discipline of respectful listening.”
#unfiltered is a series where I share my raw thoughts and unfiltered commentary about anything and everything. It’s not designed to go down smoothly like the best cup of cappuccino you’ve ever had (although here‘s where I found mine), more like the lonely coffee bean still struggling to find its identity (which also may one day find its way into a more thesis-driven blogpost).Who knows? The possibilities are endless.
Stay up to date with the weekly cup of cognitive adventures inside venture capital and startups, as well as cataloging the history of tomorrow through the bookmarks of yesterday!
I was quite surprised at the unexpectedly positive response I received for my blogpost, My Cold Email “Template”, I wrote a month back. From DMs by you, my curious readers, and my friends. A great question some of you brought up was:
“What if I have to write a longer email to get my point across?”
It happens. As some of you may already know from this post and my Contact page, I don’t believe that all cold emails have to be short. I, myself, am guilty of writing longer messages sometimes just because I can’t figure out a shorter way to express my interest in that person in a cold email. Regardless, if I think they have the time to read it or not.
