Category: Life

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v27.0

The Earth has once again gone through another orbit around the only star within four light years from us.

In the past version of David, I’ve published many blogposts. Yet one of the most continual topics that owns real estate in my mind is the idea of the 99 unsolicited, but more importantly, non-googleable (figuratively speaking) pieces of advice. I’ve already published two blogposts on the respective topics of entrepreneurship and VC. And am now compiling more and an additional set of life hacks. I imagine, at some point, I will for other areas of my life I want to spend mind space on. Asking questions. Hosting interviews. Events. LP stuff. Just to name a few.

In other words, I am on a constant search for tactical pieces of insight in the corners of both the internet and safely kept (often unwittingly) in the grey matter in 7.8 billion locations. Or simpler, I want to know what others know.

I was listening to a podcast featuring James Clear earlier this year. And in it, he said something I completely agree with. “Almost every idea you have is downstream from what you consume. When you choose who you follow on Twitter, you’re choosing your future thoughts.”

In an age that offers us a wealth of information and a million topics, posts, comments, videos, and algorithms that will distract us, it becomes ever more prescient to be a great curator. It doesn’t even have to be for others. At the very minimum, for yourself.

The amount of time I’ve scrolled through metaphoric cat videos on YouTube is appalling. And I realize that whenever I do, I face a dry spell of ideas. Luckily only briefly.

As of now, the world’s top social media platforms’ algorithms work against us. It surfaces us content we are likely to enjoy. Content that is high likely to reinforce our confirmation bias, as well as availability bias of the world. And the biggest problem with that is we are fed cousins of the same information rather than new, and possibly dissenting information that would challenge our beliefs. After all, these apps’ goal is to keep us on the platform. Not to close the app and do something meaningful with our lives. I’m excited for the day we get to build our own algorithms for consumption. But for now, it has to be more manual.

James Clear also goes on to say in the same interview when Tim Ferriss asked how he chooses which books to read. “First thing is you got to be willing to quit books fast. If you have baggage around finishing books, then you’re just going to be stuck and you won’t move on quickly enough.”

I’m guilty of the counterfactual. I’ve long prided myself on seeing things through. In fact, I still do. But at least on the consumption part, I’m slowing down my rate of learning. This year, I’m going to start measuring the number of books, articles, and podcasts I fail to complete, as well as the number of long form content media (i.e. books, movies, articles, podcasts, etc.) that have inspired an idea or an output. The goal is to optimize for learning and insight rather than completion.

Since this is the first year I’m measuring it, I won’t be able to measure the delta. But I’ll leave this encased in amber for David v29.0 and future iterations.

Doing things that are unteachable

My sixth grade teacher once told me, “David, you should be proud [she] copied you. That means you have something worth copying.”

I, like many others, spent the first 22 years of my life copying and learning from someone else’s or multiple people’s playbook. And often still do. The four years after I worked on being different. From the words of someone I look up to, “Be interesting and interested.” Where I put more effort into being interesting — doing interesting things, having interesting perspectives, asking interesting questions. I worked to create things worth copying. And when I started this blog, I followed that same ethos. I did and will continue to do my best to share my findings and takeaways. So that others won’t have to fall through the same potholes as I did.

At least, that was my belief until December 8th last year.

I hosted an event. An event I’ve never been more excited to host. An event where I was intentional about as many details as I could. And a byproduct of being in the flow state at least twice a week. While I’ll likely spend another blogpost taking a deeper dive on this topic, it occurred to me that events, just like any other medium of consumption — movies, books, podcasts, shows, and so on — should be stories. And every story has a beginning, a middle, and an end. But more importantly, every great story has:

  • An inciting incident — something that compels the protagonist to leave their current timeline to embark on something spectacular
  • A main plot (with sometimes multiple side plots)
  • Character development — the protagonist, as well as other characters, grow over the arc of the story
  • An ending where the reader (viewer or listener) can imagine no other (tipping my hat to Robert McKee)
  • And to use the reader (et al’s) time in a way that is not wasted (tipping my hat to Kurt Vonnegut)

To my joy, it was as great if not greater than expected. The feedback was phenomenal. In my excitement and post-event high, I shared with many friends, colleagues, and family about how I thought about the event.

And to my dismay, while most were happy for me, a friend told me:

“You’re built different. I could never do what you do.”

In subsequent days, two other friends told me the same.

And it reminded me of something John Fiorentino once said. “The things that are going to be valuable are the things you can’t teach or copy.” While I was initially dismissive of this corollary, I now realize there might be some truth to it.

So, how does that change the stories I’ll share here or anywhere? In the past few years, every time I do something new, there ‘s usually a voice in the back of my head that asks me, “How would you catalog this adventure on your blog? What would be the title of the blogpost? What kind of title works best for SEO?”

Going forward, I’m going to ask that voice to hush. Not to say I won’t share my learnings, but I’ll preface now that my future writings may not be written for search engine optimization. It’ll be raw. And from title to body, a truer expression of what I want to share.

So where do I go from here?

I’ve hedged to be fair my entire professional career. I’ve done tons, which on paper, seems like a lot, but I’ve never fully spent time immersing myself in only one thing. And nothing but one thing. I’m context switching all the time, which probably means I live 20-30% less of a day than a focused person.

So I’m going to have to take more risks. ‘Cause I’m starting to believe that in order to do something that cannot be copied, I’m gonna need to focus more.

Photo by Mike Lewis HeadSmart Media on Unsplash

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.

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Why Investors Talk about Grit

exercise, grit, persistence

“Magic is just spending more time on a trick that anyone would ever expect to be worth it.” — Penn & Teller

Five years ago, back in 2018, I would have never guessed. But I fell in love with the soles of another person’s feet. And I knew this was going to be one of the most tenacious people I’d ever meet.

I was introduced to “Ben” by a dear friend with one line, “No one can outhustle him.” “Ben” grew up with an insatiable appetite to learn, in a village located on the outskirts of Cairo. He would spend many days and nights in conversation with village experts and the village library, until one day he noticed he learned all he could have.

It just so happens that there’s a two-hour bus to Cairo that comes once a week. And that was how he found the libraries in Cairo, where he realized his interest in AI. But due to the bus’ odd schedules, instead of riding it, Ben chose to instead walk ten hours to Cairo every week. He’d then download, read, and print (to bring back to his village) as many Stanford PhD research papers on AI as possible. Sleep overnight at the bus stop. Then the next day, walk ten hours back to his village, where he’d continue with his reading for the week with all the loose leaf papers he had.

Needless to say, he had the feet to show for it.

I shared that story with a friend two days ago at the perennially-packed Superhot. We were chatting about the traits we look for in founders we back and the questions we ask to get there. The latter of which I’ve written about before. And at the early stages, the chief thing we look for is grit. There’s a tweet I stumbled on this week summarizes that rather nicely:

The problem is it’s so hard to see if a founder has the qualities of a “white belt who never quit” in just one meeting, even a few meetings. So, instead of sharing what questions we ask founders — most of which I know are designed to be reveal tells of grit, and are at least to my friend and his team, proprietary to some degree — I’ll share why grit matters, not just as a founder trait, but as a variable in the fundraising process, and a story that I hope will inspire you.

Candy versus the meal

One of the frameworks I love thinking about is the difference between how people think and what people talk about. This is by no means original. I actually stumbled across this when watching Malcolm Gladwell on Masterclass. For instance, when people watched the most recent Avatar movie, they didn’t say “Here’s the plot of the movie.” They talk about their favorite scenes or how great the performance capture was for underwater sequences. Neither is all-encompassing of the movie, but it gets people excited. That’s what word of mouth is.

Malcolm Gladwell calls it the meal and the candy, respectively. The meal is how people think — what people take home. They sit down with it and take time to process. The candy is what people talk about. The parts of the narrative that are easiest to share and remember.

From a go-to-market presentation I did earlier this year

Candy without the meal is clickbait. A meal without the candy means no one will talk about the good work you do. So you need both.

Similarly, in the world of venture, when I, like most other investors get excited about a deal, assuming it’s a good one, don’t talk about the whole pitch deck. Neither do I get super excited about sharing the one-liner unless it’s actually something unique. Like when a bike-sharing company pitched their one-liner as “We make walking fun.”

What I talk about is what’s cool and what stands out. That’s the investor’s word of mouth. And that’s how you fill a round. Or get people excited to help you find investors who will. Things I shared before include:

  • “That startup that hit 130% net retention.”
  • “Customers literally write love letters to the founders.”
  • “That founder cold emailed a Disney exec for 300 days straight to inevitably close their first enterprise deal.”
  • “This founder started a podcast as a growth engine to 1/ secure his first 10 customers, 2/ bring on one of the best advisory board I’ve seen to date.”

As you might notice, it’s almost impossible to guess what each company does above with just what I shared. And it sure as hell doesn’t get investors to conviction with just that. But they’re powerful enough for investors to take a second look at and talk about. Among the above, the absolute favorite thing investors love to talk about with each other is a founder’s ability to hustle. And subsequently, their Herculean efforts that demonstrate grit.

Years later, my friend on Wednesday was still talking about a founder he backed who waited in the cold outside an exec’s office until he got a meeting. Then found unique ways to turn 20 minutes into 30 minutes into hours into their first enterprise client.

The thing is it’s rare to see this. Most people promise that they will, but the best founders have demonstrated this grit time and time again before, against seemingly impossible odds. And they’re only “impossible” if you’ve set lofty goals in the past and you did nothing short of your best to try and achieve it. I’ll give another example. One that I knew if he was to start another business, you knew he was going to make it happen.

Spoiler alert: He did.

From losing everything to acquisition

I first met Anthony at 1517 Fund’s quincentennial “anniversary” summit back in 2017, designed to bring together the world’s most divergent thinkers.

The first thing you notice about Anthony is that he had a small frame. A demeanor that belied his life experiences and the courage it took for him to share them. Yet, he has a way to command the attention of his audience.

He started his business back in freshman year of college delivering food to his fellow classmates at USC. It started off as a side hustle to earn some spare change. Something he didn’t expect would become something greater, until one day Mark Cuban came to USC to give a talk.

As the fireside chat ended sooner than expected, Mark polled the audience, “What if we did a live Shark Tank?” Anthony explained that while unsure if it’ll work, but not wanting to let a once-in-a-lifetime opportunity go, he decided to pitch this idea he’d been working on — which at that point, was not even an app, but just a series of text messages between friends who ordered food and friends who were willing to deliver them.

To his surprise, Mark loved it. Soon that snowballed into Anthony dropping out of school to focus on the business full-time. They got into 500, and he became a Thiel fellow. But one spring later, amidst the hype of a party in Vegas, he miscalculated a dive into the pool. Fractured his spine. And became paralyzed from the neck down.

In the ensuing months, his top priority was not to grow what became EnvoyNow, but to breathe, to drink water — to survive. His co-founders had promised him they would look after the business and that he should focus on recovery. So he did. Months passed. And while Anthony still sat in the occasional company meeting, he was focused on mobility and feeding himself.

A few more months passed by, and one day, his co-founders decided to visit him while he was still focused on recovering. And they broke the news. The business was stalling. Investors had lost faith. Moreover, both his co-founders had already lined up new opportunities and wanted to close the business down.

As I sat listening, I couldn’t help but wonder what I’d do in that situation. Anthony instead decided to go back full-time to the business and win back his remaining team and investors. He said, “I went back to our investors. I shared where we were at, which wasn’t good. And asked them to believe in me once more. They did once before, and as long as I showed I was still passionate about the business, I was banking on the hope that some will still continue to support us.” Luckily, a small handful did.

With renewed drive and determination, and a tough situation to get out of, within the year, they expanded to 16 schools and employed 1500 students around the nation. The rest is history. They sold to JoyRun. And Anthony went on to found more companies, including his current one, Vinovest, which he started 2019 and raised an A in 2021.

If you’re curious about the additional details to the story, there’s also a great 2017 Fortune piece cataloging his journey. I love the line Blake Masters, President of the Thiel Foundation, shared in that piece, “Good luck finding something that will hold [Anthony] back.”

In closing

There’s a fun little thought exercise a couple investors I know used to do (maybe still do). They first posed the question to me when I first jumped into venture, which is:

If you had two young founders… One went to MIT, graduated with a 4.0 GPA in computer science, and was summa cum laude. The other is a high school graduate, and instead of paying over $200,000 over 4 years, took every single MIT computer science course on Coursera in one year. All else held equal, who would you invest in?

Naturally, the answer biases towards the latter. Yet, in the past few years, or at least since I’ve been in the world of VC, there’s been a bunch of logo shopping and chasing the idea of “signal.” While no one says is explicitly, logos have become more important than the hustle.

Today, we’re in a tough market. One where we haven’t seen the light at the end of the tunnel. Hell, we don’t even know when we’re at the trough yet. Or at least, the lagging indicator that we are is a massive slowdown or lack of layoffs. Yet, we recently saw Google, as well as Microsoft and Amazon, go through cuts.

And so, it no longer matters who you’re backed by or where you’ve come from. As Engineering Capital’s Ashmeet Sidana said, “A company’s success makes a VC’s reputation; a VC’s success does not make a company’s reputation. In other words to take a concrete example, Google is a great company. Google is not a great company because Sequoia invested in them. Sequoia is a great venture firm because they invested in Google.”

What matters is that you can make it out the other side. What matters is that you’re inventive and creative, that you can tighten your belt and put the pedal to the metal, and do what looks in retrospect as superhuman.

And that requires perseverance and the ability to learn. That requires spending more time on something than anyone would ever expect to be worth it. As you do so, you embark on what VCs call — insight development.

Photo by Karsten Winegeart on Unsplash

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.

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2022 Year in Review

rollercoaster, sunset

This year I learned a lot. From the fact that most of my readers love to read my blogposts on Wednesday 2PM Pacific to how I could get general partners — some of the smartest people in VC — to be vulnerable and candid to how to set up an SPV from scratch (without the help of any platform). It’s been a rollercoaster. And I loved every second of it.

My blog grew modestly. No hockey-stick curve. And that’s okay. I enjoyed inking each word. To me, that’s what makes this blog worth it.

I’ve written 87,000 words, with over a third fewer posts than last year. I want to say I was busy. And I was. But another equally true reason was that I was scared to disappoint. I wasn’t content publishing half-baked ideas. And it sucks when I know I wanted to write more. How? Because as of today, I have 53 drafts just sitting in my WordPress folder. With 245 total published essays, that’s a sixth of my thoughts I withheld or postponed because I thought: “They’re not good enough.”

Comfort is powerful. And earlier this year I found myself resigning to habitual cycles I had developed in the year prior. A fear manifested into reality. So I made a promise to myself to escape the clutches of complacency.

But while I hesitated on the writing front, I chose to take risk elsewhere. I took big bets. For one-way door decisions, bets I didn’t wait for a 100% conviction on. And just jumped when I got to 70%. As a function, I had many firsts.

It’s the first economic downturn I’m living and working through (2008 and the dot com era don’t really count as I was still in grade school).

For the first-time I broke my streak of writing weekly since the inception of this blog. While I can blame servers and bugs, the reason was simple. I just wasn’t prepared enough.

I set up my first SPV (special purpose vehicle) from scratch. With a s**tload of help, but yes, from incorporating to legal docs to setting up bank accounts, and so on.

I started interviewing LPs in fireside chats — something I never imagined I would end up love doing or be capable of doing.

I hosted my first social experiment-like event paid for and sponsored by investors for investors, rather than my usual audience of thrill seekers. Based on the feedback, I’d say it was a success. Many learnings and an indispensable village helping behind the scenes. A handful of things that could have been better. But a night of surprises. And I learned — something I hope to share more in the future (as I have larger sample sizes) — events, just like books, movies, shows, podcasts, and so on, are stories. And stories have settings, character developments, plots, a climax, and an end where the audience can imagine no other (to steal a line from Robert McKee).

Additionally, I…

  • Took my first vacation, not touching any work at all, in six years;
  • Went to my first traditional Vietnamese wedding; hell, travelled to Southeast Asia for the first time;
  • Successfully made fruit chips en masse;
  • Realized my favorite photo mode is portrait mode;
  • Built my first PC;
  • Put together my first career manifesto — my professional raison d’être.

And it’s still not enough.

But I digress. While I wrote far fewer posts, 2022 was the year I wanted to make things count. As Muhammad Ali once said, “Don’t count the days; make the days count.” The below, while I wish I had a longer list, are the blogposts that counted.

2022’s Most Popular

The below are the essays that I published during 2022, and generated the most views, ranked from most to 5th most:

  1. The Emerging LP Playbook – I never expected this one to take the top spot this year. Borne out of a personal curiosity and an attempt to better understand the black box industry of LP investing, ever since Andrew Gluck put “emerging” and “LP” back-to-back on a Zoom call, I had to learn more about it. The truth is I only knew a handful of known LPs at the time, but I’m happy this piece has expanded the horizon for not only myself, but everyone else out there who’s read this curious piece. It answers just one nexus question: For a first-time LP, where do you start?
  2. 99 Pieces of Unsolicited, (Possibly) Ungoogleable Startup Advice – I’m a collector. And have been so for a while. Specifically, a collector of quotes. I have journals dedicated to them. When the pandemic hit, I had a thought, what if I collected 99 soundbites (some albeit my own) about being a founder? All tactical. And each will share an actionable lesson. And I shared them. I didn’t know how long it’d take, but I knew that 99 sounded like a good number.
  3. How to Get Investors to Just Ask One Question: “How Can I Invest?” – I had the chance sit down with Siqi Chen, one of the best storytellers I know. And he broke down just what a founder needs to do to secure the bag. The caveat is it usually doesn’t happen after your first fundraising pitch.
  4. What Does Signal Mean For An Early-Stage Investor? – The word ‘signal’ has been thrown around quite a bit in the last two years — 2020 and 2021, if you’re a time traveler and reading this in the future. For instance, an investor would look for ‘signal’ before investing in a deal. In the above blogpost, I break down exactly what ‘signal’ means. And I imagine, in whatever time period governed by FOMO (fear of missing out), ‘signal’ will rhyme.
  5. 99 Pieces of Unsolicited, (Possibly) Ungoogleable Advice For Investors – Just like the one I wrote for founders, soon after, I thought I’d put a list of 99 soundbites for investors. And as I jumped at the opportunity to work with the brilliant team at On Deck Angels, I was living and breathing everything about investors — from angel investing to fund investing. Of course, you can sense my heavy bias towards to latter.

All-Time Most Popular

The funny, yet in hindsight, unsurprising, thing, is that the below are perfect examples of the power law, collectively generating 90% of the views ever on my blog. The below ranked in view count popularity:

  1. The Emerging LP Playbook – I wrote this piece for myself and other investors looking to be LPs. Unsuspectingly so (at least in foresight), this piece generated a huge amount of excitement not only with my initial intended audience — who, I thought, was a niche audience — but also among many VCs and angels out there. I rarely write in hopes to change people’s minds. I’m not much of a persuasive writer, but rather I hope my words offer oases for people searching for answers in a desolate desert. But of the feedback I’ve gotten, it has surprisingly changed a number of people’s minds about LPs, as well as about different asset classes to invest in.
  2. 99 Pieces of Unsolicited, (Possibly) Ungoogleable Startup Advice – Same as the above.
  3. 10 Letters of Thanks to 10 People who Changed my Life – To this day, it still baffles me how this is the most perennially popular essay I’ve written. The SEO keywords I’ve optimized for here are all related to Thanksgiving, yet the fact that search engines bring me new readers every single week without fail is an enigma I’m still unravelling. That said, I am thankful to everyone who’s given me and the 10 people I am deeply thankful for that year the attention and time out of your busy schedule.
  4. How to Pitch VCs Without Ever Having to Send the Pitch Deck – Teach them something new. Many founders who’ve worked with me can attest that that’s been my favorite line to lead with when they ask for fundraising advice. This blogpost and the person behind it (who’ll stay anonymous for now) is the reason for that.
  5. #unfiltered #30 Inspiration and Frustration – The Honest Answers From Some of the Most Resilient People Going through a World of Uncertainty – (Part two of which you can find here.) Interestingly enough, I knew this one would stand the test of time. Something we learn in Econ 101 is that business cycles come in booms and busts. And they oscillate between great times and bad times. The human emotion, our daily lives, and our careers are no exception. Collectively, I queried 42 world-class professionals about their greatest motivators. What keeps them going? I ask them two questions, but the catch is they’re only allowed to answer one of them. These pieces are a gentle reminder that bad times, like good times, never last.

Most Memorable Pieces in 2022

In writing each of the below, I felt the needle move forward. Not for the world or for the people immediately around me. But for me. That I myself took one small essay forward, but a disproportionately giant leap in the way I thought about the world around me. Each is the culmination of not just a few hours of writing, but of many things more. Provocative conversations. Research deep dives. And generous people.

In no particular order, if I were to hide pieces of my 2022 soul and mind in Horcruxes, they would be in the below:

  • The Emerging LP Playbook – You’ll realize that this blogpost appears in all three lists. The first two are outside of my control. But the reason it appears here is this piece catalyzed a spark that’ll come more into fruition in 2023. A spark that emerged from realizing the massive information asymmetry between LPs and GPs. Hell, even between LPs.
  • How to Develop Intuition as a Rookie Startup Investor – This dates as far back as 2017, when I first inked the thought in my notebook. The thesis was simple. Intuition — one’s sixth sense was a subconscious function of the mastery of the other five senses. But then, I felt ill-equipped to explicitly describe what other investors were feeling, and over time, what I was feeling as a function of what I was thinking. In it, I share each of the questions I consider and their respective answers that inform each of my senses (sight, hearing, taste, etc.).
  • How do You Know if You Should Professionalize as an Investor? – I love asking questions. To the point, and I don’t mean this in a tongue-in-cheek way, that often the best way to answer a question is with another question. I’ve gotten the above question many a time this past year, and this piece is a permutation of what helps me get to first-principles thinking when it comes to: Should you raise a fund… or stay an angel?
  • Five Tactical Lessons After Hosting 100+ Fireside Chats – I love hosting interviews. I really do. Part of it is due to the fact I love asking questions. The other half is… well… the average coffee chat is 30 minutes long. Half of it disappears after exchanging pleasantries. So, the big question is: How do you get more time with people you respect? One answer among many is by giving them a stage. That said, as I was doing my homework to be a better MC, the information out there is either paltry or too generic. So I made a promise to myself that as I do more myself I’ll share all the non-obvious lessons I learn. So that others can do better than me. And I hopefully, get to learn from them as they get better.
  • When Should You Sell Your Shares As An Investor? – Selling is really an art more than science. Like investing, often obvious in hindsight, but painfully scary in foresight. And to be a great investor, you have to distribute your earnings. And in order to earn, you have to turn something illiquid into something liquid. This piece was one of my first explorations behind what makes selling hard and how some of the best do it.
  • Quirks That Just Make Sense – Maybe there’s a bit of recency bias here, but this is something a few of my friends have known about me for a while. I just never had a good excuse to talk about it publicly. (Weird that I thought I ever needed an excuse to). But my good buddy Matt brought me out of my shell a few weeks back. And together we put together a piece about the quirks we carry and the origin story of each. Coincidentally enough, just watched Garry Tan’s video yesterday about a similar topic.

In closing

Cheers to a year of life lessons, friendships, skills and experiences acquired that were well worth the ride! And many more to come! If there’s ever any topic you would like me to write about in the future, don’t hesitate to let me know. I have two nominations already.

To peruse one of Kurt Vonnegut‘s lessons, I hope to continue to use your time in a way that you feel is not wasted.

Thank you. And stay tuned.

Photo by iStrfry , Marcus on Unsplash

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.

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Quirks That Just Make Sense

different, quirky, weird

“Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently — they’re not fond of rules, and they have no respect for the status quo… You can quote them, disagree with them, glorify or vilify them, but the only thing you can’t do is ignore them because they change things… They push the human race forward, and while some may see them as the crazy ones, we see genius, because the people who are crazy enough to think that they can change the world, are the ones who do.”
— Steve Jobs

We live in a world where everyone is seeking validation from some kind of audience — large or small. And I’ve come to realize over the years that as long as we’re chasing what most people want, we will eventually be like most people. And truth be told, forgettable. Speaking for myself, I will just be a number in a sea of sameness, rather than THE number.

I realized later than I would have liked that I didn’t want to be like everyone else, after being inspired by a rejection email from someone I deeply respect when she replied with four words “Be interested and interesting.” And I count myself lucky to be surrounded by people who think different, to borrow a phrase Steve Jobs loves. For some, that means going where no human has gone before. For others, it’s a means to live their most fulfilling life.

So, I can only thank my good buddy Matt — one of the most outlier and honest-to-goodness thinkers I know — for the alchemical jazz that birthed this blogpost. Our only ask is that you suspend judgment until you reach the end. What may seem eccentric at first glance may prove to be the kernel of inspiration you didn’t know you needed today.

Below is only a snippet of quirks — seven to be exact — that make the two of us us, but hoping this inspires a larger conversation of people being unapologetically themselves.

  1. The whiteboard in the shower: Leaving no shower thought unturned
  2. Dream journaling: Better access to conscious and subconscious memory
  3. High-quality notebooks: Evergreen homes to high-quality ideas
  4. The Emotional Catalog: The vending machine of emotions
  5. The Excite-o-Meter: Matt’s personal Stoke Diary
  6. Marriage counseling: A recipe for strong co-founder relationships
  7. Restaurant recipes: It never hurts to ask

1. The whiteboard in the shower: Leaving no shower thought unturned

There are only two kinds of reactions I get when I tell people this. Utter bewilderment. And, what I call, sparkle-eyes.

Many of my best ideas happen in the shower. In fact, about 60-70% of the topics I write about on this blogpost found its origin in the shower. But, forget myself for a second. There’s a whole movement in the world called shower thoughts. There’s also some great academic literature on the subject — that hot showers open your pores, helps your blood circulate, and put you in dopamine-high, yet relaxed states, just to name a few. But whether the science matters or not here, one of my biggest frustrations in life is losing access to great ideas just because I couldn’t commit it to memory or document them. Many of mine merely happen to start in the shower.

So, with a small purchase of a $10 whiteboard and $15-20 rainproof markers, you’ll be set.

2. Dream journaling: Better access to conscious and subconscious memory

I’ve been fascinated by dreams ever since I was a kid. Luckily, blessed by vivid imagination, I was able to synthesize the art, movies, and stories I was consuming into interactive experiences in the amphitheater of my mind. To me, dreams were the ever-evolving playground that very few tangible experiences could rival. I’m gonna be hated for saying this, but I remember the day I was let down by the Disneyland promise. I was only seven. And I told myself that day, I would start trying to remember my dreams.

You see, as fantastically awesome as dreams are, the only downside is I forget the vast majority of them within seconds of waking up.

So, for a long, long time, I’ve been dream journaling. I have a notebook by my bedside. And every time, I remember a dream, I write it down and/or draw it out. Even if all I remember is a single word or a single image. Over time, I get better at it. The better I get at capturing my dreams, the more intentional I get.

There’s now a whole slew of literature on the topic, but for me, it’s fun. And an interesting byproduct of it all is I seem to have better memory than most of my peers.

3. High-quality notebooks: Evergreen homes to high-quality ideas

This is truly a prime example that while we all come from different backgrounds, curious minds can reach the same conclusion from different angles. That’s exactly what happened when Matt and I were ideating for this blogpost when we realized we both graduated from ten-cent back-to-school-sale spiral-bound notebooks.

The more expensive the notebook, the more respect you treat it with, and the higher quality of thoughts you will entrust it to house. Think of it like sunk cost fallacy. After all, it’d be a pity to leave the sacred halls between the two leather covers unadorned with ideas that would complement the quality of the frame.

To Matt and I, our weapon of choice is Leuchtturm1917. For myself, undeniably, paper that boasts the density of 150 g/m2.

4. The Emotional Catalog: The vending machine of emotions

The human emotional spectrum is fascinating, yet quite volatile and unreliable when you most need it. For instance, I know I’m not alone in this, but I used to always find myself feeling anger and aggression upon hearing constructive feedback, rather than curiosity. That I felt anxiety and overwhelmed when on stage rather than excitement and confidence. That I felt frustrated and discouraged when writing blogposts when I want to feel inspired.

So when I committed to this blog in 2019, I started keeping tabs on when I feel strong emotions, hoping to preserve these emotions in cryogenic slumber and awakening them when I needed them most. I keep a Google Doc that has a glossary of emotions in it — from joy to anger, from optimism to jealousy, from compassion to sadness, just to name a few. And each time I consume a medium that inspires a certain emotion, I include it in that doc. They become my shots of espresso when I’m just on the wrong side of the bed.

For example, I find inspiration from Ratatouille. Or Avatar. Or Admiral William McRaven’s UT Austin commencement speech. I feel grateful after watching The Blind Side. Yet, if I want to feel sad, I watch Thai life insurance commercials (here’s an example of one). Envy, from select friends’ Facebook/LinkedIn posts. Direction, from Kurt Vonnegut or Brandon Sanderson’s lectures. And the list goes on.

5. The Excite-o-Meter: Matt’s personal Stoke Diary

Matt: I’m a big believer that energy is palpable, but ephemeral. Like a wisp of smoke, energy is beautiful and can dazzle and inspire, but it fades… eventually. The buzz dies down, and it saddens me. That’s why I’ve developed a practice to immortalize positive energy – by keeping a running list labeled “Excite-o-Meter.” It’s my personal Stoke Diary.

Here’s how it works.

At the beginning of every week, I create a “dashboard” in a specific notebook I have for work –- a two-page canvas that I reference back to throughout the week. Page one contains items that I detail at the beginning of the week, like my “Big Rocks” (priorities for the week) and “Principles to Uphold” (personal growth tenets I aspire to embody). 

Page two is more dynamic. It contains running logs of moments that captivated me in the present, that I choose to immortalize.

I allocate 25% of page two to the “Key Learnings” of the week. But the real magic happens with the other 75% of the page. I label this section “Excite-o-Meter.”

My rule is that anytime my excitement exceeds a very scientifically-defined 7/10, I jot it down immediately. 

Reached alignment on a cross-functional project that was birthed out of a chaotic primordial soup of conflicting objectives? Jotted. 

Overcame a once-limiting belief, reminding myself that I hold the paintbrush against the canvas of my life? Jotted. 

My SQL query finally ran after debugging it for 24 minutes? Jotted.

At the individual level, it helps me memorialize the moment, etching it down onto my notebook and simultaneously, my mind. But when I read the log in periods of reflection, when I browse weeks worth of “Excite-o-Meter” entries – it reminds me of who I am. Of what gets me to tick. Of what makes me experience pure exuberance. It’s my Stoke Diary, and it’s my ever-growing source of inspiration.

6. Marriage counseling: A recipe for strong co-founder relationships

Two and a half years ago, after a conversation with one of my favorite founders, I stumbled across the parallels of marriages and co-founder relationships. Ever since, while I don’t do so with any element of regularity, I’ve found couple counseling to be a huge unlock to demystifying sticky co-founder dynamics, hell, even how to make amends with friends.

7. Restaurant recipes: It never hurts to ask

I stumbled across this one quite accidentally. So, one of the things I’m quite known for among my group of friends is that I like bringing a notebook with me almost everywhere. And there have been multiple times that for a party of two, I’ve been the first to arrive. In hopes to capture my thoughts and ideas before they dissipate into the cosmos, as soon as I am seated at the restaurant, I immediately start to take notes. Additionally, when I ponder, I tend to look around as if my eyes were bees just hovering above sunflowers in a prairie without any intent to rest on any particular nectary.

That, in effect, without even noticing it myself, makes me look like a food critic — to which I’ve been offered complimentary drinks and appetizers while waiting for my dinner guest. On occasion, they serve me something I wouldn’t have ordered myself and I love it. And well, being a curious home cook I am, I had to ask how they make it, in hopes of replicating the flavor and/or texture profile at home. And I remember the first time I worked up my courage to ask, the chef de cuisine hand-wrote out her full recipe and gave it to me at the end of the meal.

Ever since, every time I like a dish at a restaurant, I give my compliments to the chef and politely ask for the recipe. Most times I get a thank you but no, but surprisingly and anecdotally, about 40-50% of the time, I actually get the recipe. And in a small, small handful of times, the chef shows me how to make the dish live.

In closing

Most people don’t self-describe themselves as quirky. Neither do they seek to find a quirk that best describes them. Quirks are products of self-discovery and unadulterated problem-solving at its purest. Bespoke solutions to ones’ problems, unabated from society’s judgmental eye, birthed by the crazy ones. And that is something Matt and I find magical.

In fact, when Matt brought up this topic with his bud, Rebecca, recently, she described it best, “Quirks are an evolutionary adaptation. They stand out and persist because they survive. Because they are a survival mechanism. Everyone has a bunch of systems. I have a way of organizing my notes, packing my suitcase, curating my notes, and a bunch more.”

While the purpose of this blogpost isn’t for you to pick what quirks you like and copy them (while we won’t stop you if you do), rather, we hope this helps you better understand where quirks come from. And just maybe, this will help you build the blueprint schematics to what makes you you.

Photo by Mulyadi on Unsplash

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.

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How to Find Your Mentor

how to find your mentor, child

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.

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:

  1. 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.
  2. 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.

Photo by Ben White on Unsplash

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.

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How do You Know if You Should Professionalize as an Investor?

climb, grow, elevation

Last Friday, one of the greatest operators and super-connectors I know, who also moonlights as an angel investor, asked me: How do I know if I should professionalize as an investor?

Undeniably, a great question. But before I share my answer to her question, I thought it’d be best if I first elaborated on what “professionalize” means in this context. It’s a term we have used more than once here at On Deck Angels. And as a result, it has spilled over into the vocabulary I use even outside of venture. But in the context of investing, professionalize is where one would go from an amateur, part-time investor to a full-time investor. Either working at a fund, starting their own syndicate or fund, or as a full-time angel.

The thing is, to be a career startup investor, you have to be lucky. The capital required to have a seat at the poker table is high. While there are many platforms — from Republic to Wefunder to Titan Invest — that are working to democratize access, the truth, for now, still is that to access the best deals, you’re either lucky as a network leader or as a capital allocator. In other words, do you know the best and most entrepreneurial talent? And do you have a frick-ton of money?

And given that some element of luck on top of skill is table stakes, I felt the best response I could give wasn’t in the form of a statement or opinion, but in the form of five questions.

  1. Why do you invest? What compels you to continue investing?
  2. What are two positive adjectives you would use to describe your sibling*? What are two negative adjectives you would use to describe your sibling*?
    • *Or life partner, or someone you know really really well.
  3. Have you ever laid someone off and regretted it? Why did you regret it? And at point after the event did you notice your regret?
    • If not… as an investor, have you ever said no to a founder and regretted it? Why did you regret it? And at point after the event did you notice your regret?
  4. Of the five people you hang out with most, what are common traits that at least two of them have? List as many as you can.
  5. If you were to start a fund or syndicate tomorrow, what would you call it?

So before you keep reading, I would recommend pausing. And to pull out a notepad and jot your own answers down to the questions above. It’s a useful exercise I ask myself, and evidently others as well, if you’re looking to professionalize as an investor.

When you’re ready, keep reading beyond the below image, as I’ll share my rationale behind the above questions.

*Author’s Note: Effectively, I was trying to space out the questions from the rationale of why I ask them below as much as I could, so that the below text wouldn’t influence your thinking (if you plan on doing this exercise).

windy road, path, goal
Photo by Adelin Grigorescu on Unsplash

So, why the five questions?

  1. Motivation – Why are you an investor? The underlying motivation matters. Are you in it for money? To pay it forward? To prove someone or some notion wrong? How fleeting is your motivation? Raising a fund is a decade-long relationship. Raising three is two-decades long of a relationship. So, the question is how deep is your motivation. Can it last multiple decades?
  2. Strengths/weaknesses – This question is adapted from Doug Leone’s. People often describe others in comparison to themselves. For example, if I say Joanna is funny, by transitive property, I believe Joanna is funnier than I am. If I say Kai is smart, I believe Kai is smarter than I am. I often find this question to be much more useful in understanding a person than just asking for their strengths and weaknesses. After all, adjectives are, by definition, comparative words.
  3. Standards – This question is a riff on Matt Mochary’s. If your answer to the question is no, then you don’t know your bar for excellence. Why does your bar matter? There’s a saying that A-players hire other A-players because they know just much it takes to win. B-players, on the other hand, know they’re not as good as A-players, but on average, still want to feel superior, so they hire C-players. A-players can stand B-players, but can’t stand C-players. So eventually, the A-players leave your company. Why does this matter for an investor? You need to be able to differentiate between an A-player and a B-player. The difference between a great founder and a good founder is a fine line, and most people miss it. If you want to have a chance at being a top decile investor, you need to know. After all, people often learn more from loss than from gain. For the second part of the question, being a great investor — or to be fair, a great anything — is all about the velocity in which you learn. Speed and direction.
  4. Deal flow – This question is a proxy of where you’re going to the majority of your early deal flow, and likely who and where you’re connected the most with. The follow up would be do you get enough quality deal flow from people with these traits. In other words, if you had the capital, are you confident you could put at least $250K to use every quarter? If not, stay a scout or raise a syndicate instead of a fund. Until you can build up to this.
  5. Legacy – Building a fund is multi-generational. Just three funds would be a 20-year relationship. And the best funds often outlive the founder(s) themselves. So the biggest question here is what kind of legacy are you trying to build? Or are you trying to build one? This legacy, founded upon your values, determines how you plan for succession and who you raise to be your firm’s next leaders.

In closing

Of course, the five questions aren’t an end-all-be-all. There’s still the ability to think through fund strategy and portfolio construction. There’s fund admin. The back office. Tech stack. Picking strategic markets where you have an unfair advantage. That said, if you can answer the above questions well, you’ll have a compelling narrative to either fundraise from LPs or join a larger fund.

Cover photo by Hu Chen on Unsplash

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.

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#unfiltered #72 The Purpose of My Writing

hug, console

“Art is to console those who are broken by life.” — Van Gogh

An investor I deeply respect recently told me, I am “really good” at long-form writing. Admittedly, even writing the sentence just before leaves me just as squirmy as when he first said it. I am of course genuinely grateful for the compliment. But my childhood prevents from fully appreciating and accepting a kind compliment.

Rather than having a practiced eye for structure and prose — which I’m sure the real linguists and writers will have much to critique on my lack thereof… for me, I can’t imagine a world where I can boil down distinct and nuanced thoughts from multiple sources in one tweet. Which could mean three things:

  1. I was never great at writing college apps.
  2. I am terrible at Twitter.
  3. I have trouble saying No to people and options.

Don’t get me wrong. There are many things out there are best expressed simply — that need no further elaboration. My blogposts on 99 pieces of unsolicited advice are examples of such. One for investors. One for founders.

Nevertheless, longer form writing helps me think. My mind is often a mess, and sometimes I wonder how I make it by with a mind that looks like the inside of an average college boy’s dorm room. It is most evidenced when I speak, but least explicit when I write. I have time to mull over thoughts. I have time to realize that not every thought, idea, Eureka! moment is a productive one.

I apologize if I seem smarter than I am. I’m not. I’m just another person looking to learn my way through life. Curious enough to know I am lacking, but confident enough knowing I can get there. When confidence in my self-worth wanes, I find solace and therapy in the letters that I ink on a page.

I’ve shared this analogy a few times with friends. That there are artists. And there are designers. The latter fulfills a need their audience has. The latter creates where the audience is someone other than themselves (while that doesn’t have to be mutually exclusive to building for oneself). For the former, the audience is themselves. It is a form of expression unforgiving to the remarks and views of others. While others may appreciate it, you create for yourself. In a way, the best entrepreneurs start as an artist but end up as a designer. For me, this humble piece of virtual real estate is my art gallery. And a small part of me fears becoming a designer through this blog. I save the design work for other parts of my life.

I’ve been fortunate to have sponsors reach out to support this virtual acreage in the wider, increasingly saturated market of content. As you might have noticed, I’ve turned down everyone so far. Partly because of alignment, but mostly, I’m not yet sure if I want to turn writing into a job. To me, writing is comforting. It’s a sanctuary where I can isolate, even briefly, from the equivalent of noisy San Franciscan streets filled with sirens and honks every minute. And upon receiving payment, I would find myself in debt to someone or some entity. That’s fine if it was an essay or a piece of content I wanted to write anyway. But so far, it hasn’t been. And if it’s not, I find myself enjoying this therapeutic process just a little less.

I’m reminded by something Gurwinder wrote a few months ago about the perils of audience capture. In it, he shares the story of Nikocado Avocado, who lost himself to his audience, in a section of that essay he calls: The Man Who Ate Himself. He also shares one line that I find quite profound:

“We often talk of ‘captive audiences,’ regarding the performer as hypnotizing their viewers. But just as often, it’s the viewers hypnotizing the performer. This disease, of which Perry is but one victim of many, is known as audience capture, and it’s essential to understanding influencers in particular and the online ecosystem in general.”

I know many of you came to this blog via the content I write about startups and venture. At least that’s what WordPress tells me. If you came here expecting only that kind of content, I will have to disappoint. And I’m happy to send you recommendations of what I read in that arena. If you came here for that and a little more, I’m excited to share more of my takeaways as I traverse this blue planet. Who knows? Maybe one day beyond.

Nevertheless, I appreciate every one of you for giving me time in your day. Stay tuned!

Photo by Cathy Mü on Unsplash

#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!

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.

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Five Tactical Lessons After Hosting 100+ Fireside Chats

microphone, podcast, fireside chat

Over the past 12 months, I’ve done over 100 interviews and fireside chats. While there are the more popular lessons out there, like asking follow-up questions and breaking the ice with your guest with a pre-interview chat or having rapid-fire questions at the end, for the purpose of this blogpost, I’ll be sharing some non-obvious lessons I picked up in the past year.

  1. Never start with a question on career.
  2. Ask your guest three questions before the interview.
  3. Do enough research to be literate in the subject you’re interviewing for.
  4. Prep the audience for questions.
  5. Ask Yes / No questions.

Never start with a question on career.

The first question always sets the stage for the rest of the conversation, especially how vulnerable and candid the guest would be.

The best question in my experience to start with is always a surprise to the guest, as my goal for every interview is to get to know the guest better than they know themselves at that moment in time.

For how you measure success… if that respond with, “How did you know that?”

In practice, it looks a little something like… “I want to start this chat a little off-center. In the process of doing homework for this conversation, I came across the name: Bootstrapping Bill*. Could you share what that name means to you?”

*Footnote: This can be a high school or college nickname or an activity that they were heavily involved in that’s not related to their current career. Or a role model they had when they were younger. Other starter questions can be about quirks they used to have or still have that are:

  1. Not embarrassing
  2. Something that only they have.

For example, for some of my interviewees, I found out:

  • That someone used to write code on a notepad
  • A longtime fandom around Gary Keller
  • A nickname the guest used back in his street dancing days
  • A class they really enjoyed taking in college and an art professor who inspired her to pursue entrepreneurship
  • Someone who used to walk by foot 15 hours one-way just to go to a library in Cairo to download PDFs of Stanford research papers to take home and study

Of course eventually it all has to tie back to the topic at hand, which is usually through a trait they developed early on that created the person they are today. Grit. Creativity. Rebelliousness. Kindness. And so on.

Ask your guest three questions before the interview

To piggyback on the above lesson, don’t touch things that are highly personal and risqué, like their social security number or their divorce. The latter without their explicit permission. You never want to be in the situation where you make the guest feel bad. As such, in my email to them a week in advance with the questions I plan to ask, I ask an additional three questions to help give me parameters for the conversation:

  1. What would make this interview the most memorable one you’ve been a guest for even two years from now?
  2. Are there any topics you don’t want to talk about? Or are sick of talking about?
  3. Are there any questions you have yet to be asked, but wish someone were to ask you?

Of course, also share the questions that you plan to ask before the interview. Leave it up to them whether they want to prepare for them or not. And if you do so, they’re likely to bring more robust and less generic answers for your audience. Unfortunately, not always true depending on the individual you invite and how busy they are.

Do enough research to be literate in the subject you’re interviewing for.

Unfortunately, not every A-lister will bring their A-game. Some have been busy. Others are distracted. And a handful of others frankly just don’t care. For them, this is just another talk they’ve done a million times. Not THE talk of the year. Even if it might be for you.

Luckily, it doesn’t happen too often. But it does happen. And as such, you can’t just ask a question. Instead, I like to give the speaker enough time to think of an answer. I call it the QCQ sandwich.

  1. Start with a QUESTION.
  2. Follow up with CONTEXT.
  3. And close with the initial QUESTION.

I’ll give an example.

“Since you just mentioned LP-manager fit / I want to switch gears for a second… I’d be remiss not to ask you about how you think about it. In your experience, how have you seen the best fund managers think about LP construction when they begin fundraising versus when they’re about to close the fund? To shed some extra color, I’ve recently chatted with a number of emerging GPs. And there seems to be a concentration of thought leadership around… [additional context] So, I’m curious, are you seeing the same? Or have my observations departed from the median?”

Most people either only ask the question or lead with context before asking the question (I’m guilty of the latter myself from time to time).

To be fair, you may not need to use this structure all the time. But for people whose answers are typically less structured and may need some time to formulate a robust answer, this is the play. A proxy for this is if their answers only get better the more they talk or if they haven’t had a chance to look through the questions you sent them beforehand, but they typically like to.

Then there’s the exact opposite. Even if the guest speaker is well-intentioned, in efforts to cram as much info into an answer as possible, their talk becomes overly informational. I forget which world-class podcast host once told me this, but he said that that every episode he does is 20% informational and 80% entertainment. The footnote is that the 20% has to be so insightful that it can carry the episode just by itself. The sign of a good episode is if the listener walks away with at least one thing they didn’t know before.

I go back to Kurt Vonnegut‘s #1 rule on writing. Use the time of a total stranger in such a way that he or she will not feel the time was wasted.

As the MC, your goal is to be the steward for insights. The spotlight is never on you, but the question is how do you support your guest in a way that they’re able to put the best foot forward.

Prep the audience for questions

There are two angles I usually tackle from when prepping the audience for questions.

  1. I tell them exactly what they can ask at the beginning and stay away from those topics so that the audience can ask during Q&A if they have no other questions in mind.
  2. Give the audience time to ramp up questions by alternating between live questions and my prepared questions even in open Q&A.

“We’re going to cover a lot of ground today from [topic 1] to [topic 2] to [topic 3]. But if I don’t get to all of them, and you’re still curious about them, please keep us accountable during the open Q&A after.”

And I usually don’t get to all of the above topics, which leaves room for the audience to ask them. Before I ask my “last” question for the interview, I also tell the audience to the effect of: “This is going to be my last question, before I turn it over to everyone present today. So for anyone who would like to ask X something, in about 3 minutes, it’ll be your time to shine.”

The big takeaway is that it always takes a bit of time for the audience to ramp up to ask their questions. And this helps seed some possible topics not covered in the interview so far, so the guest also feels like they’re not repeating themselves.

Since almost every interview and fireside chat I’ve done has been virtual in the past year, this second tactic is designed when you a Zoom chat but I find is still useful when you have a shy live in-person audience. I always tell the audience to leave questions in the Zoom chat at the beginning of the interview. That I’ll call on them when we get to open Q&A. More often than not, the Zoom chat is less alive than I would like. And when it is (and I admit this has only been a more recent discovery of mine), I say:

“We’re going to try something new. During the open Q&A, I’m going to alternate between questions I’ve gotten before this chat to live questions from the audience. So feel free to pop your questions into chat, as I start with the first pre-submitted question.”

I know some MCs seed audience members to ask questions at the beginning of live Q&A for it to not seem awkward. I’ve seen it work, but sometimes I’ve also seen those 1-2 people take control of the Q&A, where the rest of the audience doesn’t feel like they have the opportunity to ask their own question, so they turn passive. With open Q&A, I try to give my audience agency to determine the flow of conversation. Sometimes, they just need an inspirational nudge.

Ask Yes / No questions

For a long time, I had this fear of asking yes/no questions during fireside chats. The main reason was that I believed it would lead to a lackluster interview. The guest would give a one-word response and that we would have radio silence after.

But, contrary to my initial belief, I realized over the past year that yes/no questions are insanely powerful, specifically in the context of public interviews and fireside chats. I do want to note that they don’t hold the same weight in mediums that are known or sought for their brevity. For instance, emails and instant messaging. Where speed is the name of the game.

It’s specifically under the circumstance where there’s an allotted time and an expectation to fill the void with content that this tactic shines. The guest would more often than not feel an urge to fill the empty void with additional thoughts and context. In that moment, sometimes they share something that is more off-the-record than they initially planned. Of course, in realizing that it is, and since most of my fireside chats are recorded, I follow up with the guest after to make sure they’re okay with the recording.

As an interviewer, at the same time, I’ve learned to hold myself back. There’s an equal if not more powerful urge in me to fill the void with questions. After all, oftentimes, this is the audience in which I had invited, and feel my reputation is on the line. If you could see below the camera, I have a sheet of paper in front of me where I write “Shut up” to myself at least twice before I jump in.

In closing

While I share all the above, just like being a founder, you could do everything right and the interview may still fall short of being ideal. And when some interviews do fall on either deaf ears or I feel I was just unable to bring out the best in people, like many others, I wonder… do I just suck at being at asking questions? Or being an MC?

It’s an iterative process. And the fun part of it all is that it makes me a better investor. I ask founders better questions. The answers I get when diligencing are more valuable.

The above isn’t the end-all-be-all. I’ve written on this topic before, and I will continue to work to be a better interviewer. But hopefully the above serves to bolster your arsenal of tactics.

Photo by Keagan Henman on Unsplash

Edit: Added in a fifth lesson that’s too short for a full blogpost, but longer than a tweet.

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.

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#unfiltered #71 In Search For Work-Work Balance

balance

My friends who know me well know I have this concept I call work-work balance. And in sharing it with someone new, it’s usually met with a light chuckle. I never mean it as a joke. But nevertheless, people take it as my attempt to be snarky and witty.

I believe most of you, my readers, are familiar with work-life balance. A lifestyle that balances work and your life outside of work, often one that spends the capital earned though work. When I hear most people say it aloud, its most frequent use case is in avoidance of doing more work. But the underlying principle is that most people don’t enjoy the work they do. Rather, they find their joy and fulfillment in pursuing hobbies and passions outside of the confines of a 9-to-5.

Just like having a work-life balance is a privilege, having a work-work balance is, in my humble opinion, even more so one. Speaking of privilege, earlier this week, I had the fortune of hearing a rather profound line:

“If you do one thing in life that fuels and motivates you, then you should yourself lucky.”

So, in even talking about work-work balance, I admit I came from a position of privilege, but one I do not think is unattainable for those who also have the privilege of debating the technicalities of work-life balance.

Work-work balance is the balance of doing what you love doing with work that you need to do to continue doing what you love doing. To me, work that I enjoy doing — interesting projects — fulfills me. It gives me meaning and purpose in life. To best illustrate this concept, I’m going to have to steal Elizabeth Gilbert‘s line in a 2016 interview with On Being. It’s not the first, and it won’t be the last time I quote her here:

“Everything that is interesting is 90 percent boring.”

When you’re proud to have work be your identity

Starting something — anything that is going to be core to your identity, even if it is only briefly — is going to be unhealthy.

Being a great venture-backed founder is unhealthy. Starting a venture fund from scratch is unhealthy. Being a world-class content creator is unhealthy. Being a diligent and serial author is… well, you get it. Hell, even binge-watching the latest and greatest Netflix show is unhealthy.

It is also the difference between passion and obsession. One keeps you daydreaming; the other keeps you from sleeping.

I’m not advocating that everyone live an unhealthy lifestyle, but that the concept of work-life balance is a lifestyle that doesn’t fit everyone, but those who have not or have yet to find deep fulfillment in the professional aspect of their life. For those who have found their life’s work, work-work balance may be a more sought-after lifestyle. In working mainly with founders and emerging fund managers, their life stories seem to corroborate the previous sentence.

In the world of startups, I often tell founders, and have many a time, advised founders not to take venture capital. There is no shame in creating an great and fulfilling lifestyle business. But as soon as you take venture, that’s a different story. After all, another name for venture capital is impatient capital. It is the perfect permutation of not just ambition, but also of expectation. The greater you raise in venture, the greater the expectation.

A $10 million valuation is not a number indicative of your company value. In fact, I think the 409a valuation does a better job of that than what VCs price your company at. Rather, a $10 million valuation on a social media company is a bet that you have a 0.0025% chance — a 1 in 40,000 chance — that you’ll be as big as Meta. At least at the time of writing this blogpost. Equally so, a $1 billion valuation is a bet on the odds that you have a 1 in 400 chance to grow as big as Meta. As Uncle Ben said, “with great power comes great responsibility.”

And as such, the expectation and the will of your new bosses — your investors — is that you can scale a team that can help you capture that opportunity. And for VCs, or die trying. Many, if not most, great VCs would much rather you bat for the home run than walk a base. After all, the success of an investor is not defined by their batting average but the magnitude of home runs she or he hits. But I digress.

As a founder, you must love your work so much that it’s contagious. That it affects your investors, your team, and your customers. Why? Because in the course of building a rocket ship, there are a million and one things that can go wrong, and a million and two things that feel tedious, repetitive, and slow. And the work you enjoy doing must be so powerful that just the thought of being able to do more of it invigorates you through the long troughs between wins.

I say all this to every founder I’ve met who didn’t fall madly in love with their problem space and who expect venture funding. The going will get tough, and I, like many other investors, want to know that you have the grit to make it through this long, windy journey. Having a good pulse on work-work balance is one of a few proxies for that grit.

Of course, I do want to posit that a work-work balance doesn’t mean you should make prolonged sacrifices to your mental health, your sleep schedule, or your time with friends and family.

Photo by Piret Ilver on Unsplash

#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!

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.

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#unfiltered #70 Conviction Comes From The Stories We Tell Ourselves

focus, conviction, motivation

On the second half of a late summer Friday, as I was overlooking the singed blades of the parched grass in our front yard, I found my good friend, Andrew, in my inbox. An inbox that was about to be empty from filing an eclectic collection of investor updates, food science analyses, tech articles, and my weekly subscription of Substack extraordinaires into my Read Later folder.

An email headline in boldface. All it would take would be two clicks. Two clicks to add to my party of internet writers I would be conversing with over a Saturday morning of roasted hojicha tea. Instead, I clicked once. Just once. And I’m glad I did.

Andrew started writing again. Pen to paper. Or rather, finger to keyboard. And that, that was worth celebrating. I, like many of his other friends, had been starved, deprived, relieved of his prose given his busy schedule. In it, he postulated the relationship between commitment and conviction.

“Commitment helps you stay on the path. Conviction is what calls you to the path in the first place.”

In sum, the pre-requisite for commitment is conviction. And so, it got me thinking about the source of conviction…

From inspiration

For decades, athletes have tried to break the 4-minute mile. According to British author John Bryant, since 1886. “It had become as much a psychological barrier as a physical one. And like an unconquerable mountain, the closer it was approached, the more daunting it seemed.”

But it wasn’t till May 6, 1954, did Roger Bannister break it with a time six-tenths under the mark. As soon as Bannister did it, 46 days later, another did. One year later, three runners broke the once elusive 4-minute barrier in one race.

The thing is, nothing technological had changed in the world when all these runners post-Bannister broke the four minutes. Nutrition hadn’t drastically improved. Neither was there drastic evolution in the technology of shoes. Yoram Wind and Colin Crook argues it was a mindset shift. The impossible was possible.

We see the same notion today in the world of emerging markets. In these markets, the first wave of unicorn founders is usually spearheaded by Harvard and Stanford grads building X for Latam or Y for Africa. For instance, both of Grab’s founders are HBS graduates. Gojek’s Nadiem is no exception. Nubank’s David Velez holds a similar Stanford GSB degree. So does Cabify’s Juan de Antonio. Rappi’s founders are also Stanford alumni. And the list goes on. They come with the Silicon Valley mindset in a market underestimated by not only the broader world but by the homegrown talent themselves. I like the way a Midwest founder-turned-investor once put it, “My mind is in Silicon Valley, but my feet are in the Midwest.” The same is true for this first wave.

And once they’ve proven it’s possible to reach unicorn status, the second wave follows quickly after.

Most people follow in the footsteps of our predecessors. Older siblings are the same for their younger siblings. Parents are that for their children. While I’m not a parent yet myself, I do aspire to be that for my children. Equally so, that’s why we need diverse representation in media, in positions of power, and in stories.

For many, conviction comes from examples to disprove the limitations of our own imagination.

From emotion

For a handful of others, conviction comes from a deep desire to prove or disprove.

There’s a superpower that comes with being underestimated. Reddit’s founders famously hung on the office walls the words of a Yahoo! exec who told them,  they were nothing but a “rounding error.”

When Michael Phelps’ eight gold medals in Beijing were on the line, their coach Bob used what the French team was boasting on the papers as motivation in the locker rooms. “The Americans? We’re going to smash them. That’s what we came here for.” And soon after, the world was blessed with one of the greatest races to date. A race of which the Americans — the underdogs — pulled a miraculous spectacle of conviction and resolve.

For founders, you need obsession, not just passion. Many of the best ones have a personal vendetta — a deep, unquenchable desire borne out of time spent in the idea maze. Every successful founder needs to perform 10-15 miracles in the startup to household name journey. Trials by fire that are meant to deter the fainthearted.

After chatting with a number of limited partners (LPs, folks who invest in venture funds) over the past two months, I’ve realized the thread of founder obsession continues here. That investor-market fit is not just a function of professional experience but also of life experience. Once again, a deep desire to change the world from personal frustrations and the hope that no one will ever have to go through what they went through.

In closing

Earlier this year, Reed Hastings shared a profound line with the graduating class, “[stories are] about harnessing the human spirit.” Conviction starts from the story we tell ourselves. The story itself is bound by the limitations of our own imagination. And conviction happens to be the belief that we can will our imagination into existence.

Michelangelo once said, “The sculpture is already complete within the marble block, before I start my work. It is already there, I just have to chisel away the superfluous material.” Commitment is the dedication to your conviction. A devotion to say no to distractions and yes to the person you want to be.

We live in a world filled with shiny objects. So, ask yourself, do you want what others want? Or what you truly want? Is your conviction inherited or innate?

I was listening to the latest episode of the All-In podcast, and David Friedberg echoed a similar notion for the greater human race, “What differentiates humans from all other species on Earth is our ability to tell stories. A story is a narrative about something that doesn’t exist. And by telling that narrative, you can create collective belief in something. And then that collective belief drives behavioral change and action in the world.”

Photo by Devin Avery on Unsplash

#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!

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.

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