Tag: vulnerability

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#unfiltered #62 What I Learned From Hosting Vulnerability Circles

As you know from this blog, I spend a lot of time writing from my head. Startup, this. Venture capital, that. But comparatively little from my heart. This blog, Cup of Zhou, is not going to be the next Stratechery. Or a 20-minute VC. Or a Not Boring. For each one of the afore-mentioned, I have a tremendous respect for. Ben at Stratechery, Harry at 20VC, and Packy at Not Boring all do something I can not. And they do it really, really well. This blog is just nothing more and nothing less than me. It’s not a publicity stunt. And sure as hell, a terrible branding platform. In fact, I’m willing to shoot myself in the foot again and again, as long as I can be true to myself here.

Four people last week reached out to me. Two founders. A friend from college. And another from high school. They told me that life was tough. Things weren’t working out. And rejection sucks. They’re right. Whether your goal is to change the world or have an enduring marriage, life is rarely easy. You’re going to get that left hook more often than you’d like. And rejection fucking sucks. To those who said it gets better over time, it doesn’t. At least for me. You may get desensitized to each blow, but there will always be jabs and uppercuts that will sting more than the rest.

While I find comfort in writing my thoughts here, most people don’t have a safe space to be candid. As COVID is slowing its pace, at least in the Bay where we’ve reached a level of herd immunity, a while back, I decided to start a new series of in-person dinners where people will feel safe being vulnerable.

In hopes that this will help those hosting such circles outside of the Bay, here’s what I learned.

With both online and offline, I played around with a combination of social experiments and social observations. The former, I would lead and guide conversation through centering exercises and intentional “stage time.” The latter of which I would bring everyone together, but spend less time steering the conversation. Both were structured and all attendees were informed of the ground rules, theme for the night, and homework, oftentimes a personal story to share with the group, necessary to bring thoughtful conversation to the table.

Eyes are the windows to the soul

In group settings, shyer attendees would allocate more of their eye contact when speaking towards people they were familiar with. And given that I bring strangers (to each other) together, shyer attendees make eye contact with me – the one person they do know – more often than with others. But as they find more comfort in their fellow attendees, they slowly allocate more attention to them.

I often found that the best remedy for this was in two parts:

  1. Make eye contact with them while speaking,
  2. Mention their name intentionally a few more times than I do with other more confident guests, and
  3. Once they sustain eye contact with you when you’re openly speaking to them, redirect their attention to another attendee by then mentioning an adjacent topic that the other attendee brought up, and making eye contact with the other attendee.

Give people a path to retreat for them to stay.

Vulnerability and true authenticity is tough. For some people, it’s easier to do with strangers. For others, it’s much harder to open up to people who you’ve never met before. Nevertheless, I like to err on the side of caution. Even after I send out personal invites to each person via DM or text, where I give them the context of what they’re about to embark on, I still preface the email that includes all the details, specifically the ground rules of authenticity, open-mindedness, and candor, with: Are you willing to be vulnerable?

Then right below that question:

If your answer is “no“, I completely understand, and I won’t force you to come. Just let me know if you’re opting out, as I need an updated headcount for our reservation.

But if it’s “yes“, … [read on]

And in that same email, everyone is BCC’ed. The guest list on the calendar invite is also not visible to each guest.

Guests have multiple opportunities to opt-out. And they should if they’re uncomfortable with the setting, since the people who do come are the ones who will truly find value in having a vulnerability circle.

Being time sensitive doesn’t matter

I initially thought that people really cared that each session was going to last 2 hours and everyone only had 15 minutes of “stage time”. And the implicit promise that I would be cognizant of everyone’s times mattered. And while it still does to a reasonable degree, it hasn’t seemed to be a priority for folks especially in my social observations. The only times it does matter are:

  1. The energy in the conversation is waning and people start noticing hot silence, as opposed to cold silence.
    • Borrowing the terminology of “hot” and “cold” from Jerry Colonna, hot silence is what most people deem as awkward silence. A silence where people intentionally seek to fill the void. On the other hand, cold silence is where people are comfortable with or seek comfort in the absence of speech. Either that it lets ideas and thoughts ruminate or there is a space for tranquility that one might find calming.
  2. Someone has another commitment right after the event.
  3. People who don’t enjoy the conversations, topics, or people.
    • Luckily, this last one has yet to happen since I curate each person who comes to these circles myself. But, given how many more circles I will host in the future, it’s something I’m aware might happen.

Conversely, many of the ongoing conversations former attendees are still having with each other have come from circles that have gone overtime. This is something I’ll continue to have my pulse on to see if anything deviates from this thesis.

In closing

These vulnerability circles are only the first of many more to come. And of course, future circles will come in different variations. The ones I have planned for early next year thematically revolve around the absence and the dulling of particular senses, in order to heighten other ones. And you betcha I’ll have much more to write about then.

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!

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#unfiltered #57 True Vulnerability Is Messy

art, vulnerability

One of the greatest blessings I have today is that friends often introduce me to their incredible friends. Two weeks ago, one of my good college friends introduced me to a friend he made down in LA. Sam. A brilliant aspiring fund manager. Cut her teeth with driving impact at non-profits. But above all else, her ability to host dinners with strangers caught my eye and ear. Since I’m a big fan of sharing my learnings from hosting brunches with strangers and social experiments. In a short span of a week, we became fast friends. Expectedly, I had to ask Sam how she brought strangers closer together at her dinners.

Last week we jumped on another call where she walked me through her process. “David, it’s easier to show you than to tell you. Are you open to being vulnerable?”

“Yes.”

“Tell me about your life philosophy.” She asked me what influenced the life purpose I have today. Over the next half an hour, we dove into the depths.

The first third was populated by a politician’s answer. I wasted zero calories jumping into my upbringing and why that has influenced the person I am today. Unwittingly then, but in hindsight clarity now, they were all narratives I’ve rehearsed before – intentionally and unintentionally. After all, they were the cookie cutter responses I’d give to cookie cutter questions most people asked.

Yet, after each of my narratives, there would be a brief pause. What lasted only mere seconds felt like eternity for me. In those moments, she was a woman of few words. Comfortable with silence, she would occasionally beckon, “Tell me more.” On the other hand, I was impatient to fill the void. The emptiness was unsettling. I felt like a circus monkey forced to perform and that the audience’s claps and laughs was the only representation of my self-worth. But that was all in my head.

“Tell me more.”

I filled the next third with stories I’ve told before but not in a while. A reminder to myself that I am more than the person who existed in just the last two years. That I’ve had 23 other years than I somehow left in the attic collecting dust. That I am not a function of my job title or the people I surround myself with currently. But rather the accretion of everything before as well. Where the first third was sharing the mold I now fit in, the second third of our conversation was sharing why seemingly disparate events and relationships in the past fit the mold I had just shared. In sum, I was still making sense of things.

“Tell me more.”

I was ill-equipped to deal with the last third. I was no longer armed with the stories I had rehearsed throughout the 25 years I’ve been alive. Analogously, I was someone who just learned what exponents and derivatives were. When my 5-year old cousin asked the fifth “why”, I didn’t have an answer for her. Not like I did with the first four.

In this case, she asked the third “why”. And I was already at a loss for words. I was lost between doubt and anxiety, between shock and curiosity. But it was in the last ten minutes when I finally dropped my guard. My guard where everything had to make sense. My guard against the fear of uncertainty, not just for the future, but for my past.

A few moments of silence passed. Once again, long, but not nearly as uncomfortable as in the beginning.

At the end of our conversation, she left me to wrestle with my own uncertainty. But with the offer to dive even deeper the next time. And I was left with my own turmoiled mind, unable to find the words outside of sweeping generalizations to express what I felt and how I felt it. While I was grasping for the Merriam-Webster to make sense of my inner entropy, she sent me the below wheel. Something she relies on, to this day, to keep her emotional vocabulary from atrophying. In being able to identify her emotions, she is better set to understand them.

As I’m writing this blogpost, her words “true vulnerability is messy” still ring in my head. And it’s in those moments we build trust and bond with each other. And also with ourselves.

The purpose of this exercise and with vulnerability is not to have more answers than questions. Bur rather more questions than answers. And the ability to ask more.

Emotional Feeling Weel
Source: The Junto Institute for Entrepreneurial Leadership

Cover photo by Alice Dietrich on Unsplash

*Retroactively added Sam’s name into the essay

#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!

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The Double-Edged Sword of Transparency, when Fundraising

In the venture world, startups have another alias. 10-year overnight successes.

For the majority of the world, we hear about startups through a Thursday morning TechCrunch article or by way of the Friday Happy Hour gossip stream. Well, okay, I’m not being time sensitive. We’re not going out for Friday night happy hours these days. But we might spy something in our social feeds after a startup hits 5 million users or they just raised $50 million from a top-tier venture firm.

And these TC or Forbes or NY Times articles paint these founding CEOs to almost be perfect individuals. Good news. They’re not. They’re human – just like you and me. Over the years, the more I’ve gotten to know these leaders, the more I realized how similar we are. How similar they were when they were where I am today. And even now, how they still feel the unease in the uncertainty in the world. My study last week on how people are living through the pandemic – what inspires them or what frustrates them – further illustrated our similarities. An animator who’s fought against doubt. An executive who lost his grandpa, broke up, and felt lost in the corporate politics. A founder who was forced to make the tough decision of leaving his team. And much more.

What’s that one analogy people use again – to show that everyone is living a life we know nothing about?

A duck, above the surface, perfectly calm and composed. Underwater, furiously paddling to stay afloat.

The double-edged sword

The good news is that most VCs know that founders aren’t perfect human beings. The bad news is the irony. On one hand, they know that founders aren’t perfect and should be willing to be vulnerable. On the other hand, too much vulnerability means that VC’s say, “I’m out.”

In many cases, investors may seem hypocritical. And arguably, there’s a handful of them who don’t even know what they’re looking for themselves. Yet, in most scenarios, the bargaining chip is on the investors’ end. Not with the founders. It’s frustrating. I know. I’ve talked to founders and will continue to talk with founders who feel that way. So, what is that fine line between the showing “perfection” and embracing imperfection?

Making the blade that works for you

When founders ask, this is what I tell them.

  1. Be upfront with your investors if you’re incompetent on an aspect or aspects of the business.
  2. Show them you’re competent… in finding a way to be competent.

Be upfront with your investors if you’re incompetent on an aspect or aspects of the business.

Address the elephant in the room. If you don’t bring it up, they’re bound to ask. Or worse yet, if they don’t ask, it’s going to be gnawing at them in their minds. And may end up being the main contributing factor to a “No”.

Show them you’re competent… in finding a way to be competent.

Early-stage VCs usually take between 2-4 months before they go from “Hi, my name is Buttercup” to “Take my money”. And here are the steps:

  • Coffee chat, aka “Hi, my name is Buttercup” (If you’re wondering why “Buttercup”, there’s a story behind there, but another day. Or if anyone’s dying to know, DM me or ask me in the comments below.)
  • 2nd meeting with same individual partner (maybe a +1)
  • Full partnership meeting
  • Diligence
  • Term sheet, aka “Take my money”

Lesson 1: Don’t skip steps (for the most part). What do I mean? When you’re having a coffee chat, your goal should not be to get a term sheet there. Your goal is should be to get to meeting 2. Think of it like a sales funnel.

Lesson 2: Learn and grow during the time you get to know an investor. Doers > thinkers. Hustle. Be scrappy, resourceful. At each step, the VC(s) are evaluating if you have the acumen, competency, and what Sequoia Capital calls it – a bias towards action.

Let’s analogize with the equation of a line: y = mx +b. We measure a founder’s competency not just at “b”, but a greater emphasis on “m”. And over the course of the time we get to know each other, if a founder can prove that to us. For me, after the first meeting, I usually give a couple pieces of advice. “Oh, you should really talk with Sarah. She’s really good at sales.” Or. “Have you thought about this UX improvement in the user journey?”

What I’m looking for, by the time we have our second meeting, is what have they done in the mean time. And for a great founder, there are 2 possibilities:

  1. They acted on the advice, and they come back with the results.
  2. They heavily considered the piece of advice. Did something else. Explained to me why they did something else. And also share the results of that decision.

In both scenarios, they have new results by the time we meet. They don’t have to be “right”, as if I’m even a person who can evaluate what’s right versus wrong. But they do have to learn fast. Hustlers make mistakes. And through the mistakes, they learn. Fast. It’s a preamble to what working with a VC looks like.

If you’re curious, Chris Moody at Foundry Group has a brilliant 3-part series of why you shouldn’t take money from a VC. In his first reason to not, if you want to build a lifestyle business. Otherwise, you’ve got to learn fast and be scrappy.

Here’s an example of scrappiness

When I was an operator, we were strapped for cash and looking for cash, so we didn’t have much of a budget for marketing and advertising. Admittedly, we also didn’t really know how to market the business. Minus a few theoretical classes, we knew nothing.

We used free student printing (for us up to 10,000 pages) to print out flyers we made by ourselves. Given that our audience included both SMBs and millennial/Gen Z’s looking for jobs, as much as we wanted to flyer to college students at the plaza or in front of local businesses, we knew it wouldn’t be smart. ’Cause everyone else was doing so.

So then it came down to the question: where do people have plenty of attention to spend but have not yet been saturated with information. For us, it was the bathroom. Specifically, in the stalls. When you’re locked inside the bathroom, doing your business, you either look at the door in front of you and/or at your cellphone. And the doors were often blank canvases. So we decided to stick our flyers on the backsides of these stall doors – both in the dorms and in public restrooms, which inevitably got our websites 10s of 1000s of views early on.

That said, the janitorial staff tore down our flyers every night at 11pm. So we had to be back on the streets and sticking in flyers in public and dorm bathrooms every morning at 5am. And it so happens, I once talked to one of the university’s janitorial staff members and he actually said thanks. Since he found his new job via a flyer he kept having to rip off.

As the economist Herbert A. Simon says, “a wealth of information creates a poverty of attention.” As an entrepreneur, you’re looking for the margins, where there is a poverty of information and a wealth of attention.

In closing

I can only speak from my perspective and what I seek in founders. But having talked and learned from a number of investors who have a track record for returning >5x MOIC (multiple on invested capital), I know I’m not alone.

It’s okay to be vulnerable of the potholes ahead – to not know how to do certain things. We’re human. It’s okay. But show that you have at least have a hypothesis on how to learn those things.

Photo by Ricardo Cruz 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!

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#unfiltered #26 Am I At My Best Right Now?

I’ve been debating for the longest time whether I should put out this post or not. Not only does it require me to “open up about the potholes“, as Jeff Wald puts it, I’m not sure how I should be feeling. Or maybe I do, but I’m just not willing to admit it to myself.

Last week, I read Brad Feld‘s post, “Are You At Your Best Right Now?“. And it was the final push that gave me the courage to write this. After all, this wouldn’t be a member of the #unfiltered series if I wasn’t sharing my raw thoughts.

Am I at my best right now?

I’ve had the long standing belief that if I’m not making any new mistakes, then I’m not taking risks.

And if I’m not taking risks, I’m not improving.

For the past 6 months of quarantine, I haven’t made any mistakes… neither ones I’m proud of nor severely regret. Half of which I believe most people could do without. Though I don’t set myself up for mistakes that I think are foolhardy from the get-go, I am not learning if I don’t make any mistakes at all. I’m not talking about mistakes that I make without a second thought of regret. Like drinking 7 cups of water today, rather than 8. Or forgetting to put up the toilet seat. Or a grammatical error in my writing.

I’m talking about mistakes that have defined, define, and will define my life’s trajectory. Inflection points that draw our life’s story on a once blank canvas.

My pursuit of ‘the best’ prior

In my first two years of college, I made many mistakes as an operator, as a friend, and to my promises. I over-promised and under-delivered. I let a friend I really respected and cared for down. To the organizations I was lucky to be a part of, I juggled too many things at once, thinking multi-tasking was an attribute of pride and prestige.

In my third year of college, I took networking to a new level. And along the way, burned bridges in my persistence and lack of awareness.

In my fourth year, drained from the relentless ego contest, I took a step back to reflect and be more candid than I gave myself the liberty to previously. In my pursuit of honesty, once again but in a different context, I didn’t consider the impact of my words with a handful of friends.

In graduating, I took a risk to not accept the offers I had on the table – some of which I know people would fight for. I chose a path that I felt I wouldn’t regret in the then amazing upside of the economy.

In the years following, I made bets to be at places, to be with people, and to learn from them that I had doubts other platforms would provide. In retrospect, some more foolish than others. Placing trust and hope that some of my friends who knew considered in ill faith.

But every time I learned.

I became a stronger person than when I went in.

Now

These days when friends, colleagues, and strangers ask “How are you doing?” or “How have you been?”, I’ve become my own worst nightmare.

“I’m fine.”

“I’m okay.”

While I’m not lying, I hate myself the moment I utter those words. First how much it’s become a knee jerk reaction. But secondly, and more importantly, how much hasn’t changed since the pandemic.

Like many of my friends and colleagues, and I’m sure, many more on this planet, I had 2020 plans. Plans to take risks and make mistakes. Unfortunately, for one reason or another, many of them have been put on a stalemate. At the same time, I know many of my friends aren’t doing well. From breakups to layoffs to the impending doom of deportation to deaths in the family, I feel like I should be the last person to complain.

In closing

I want to be clear. I’m not looking for pity here. But I want you to know. It’s okay. You’re not alone. While we all are feeling a different magnitude of emotions now, you’re not alone, when “I’m okay” belies what we’re all feeling right now. I can’t speak for others, but I am not at my best right now.

If you need someone to talk to or just someone to listen, I’m here.

Photo by Bruno van der Kraan 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!

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