#unfiltered #39 Five Lessons from Trying to Engineer Serendipity in a Virtual Environment

startups, spark, how to engineer serendipity, social experiments

Over the past few months, I’ve been slowly experimenting with how I can take Hidden Questions online, while not sacrificing the intimacy of the relationships it builds as well.

Hidden Questions started as a question game I played with friends and colleagues, which eventually expanded to other strangers. The goal of which was to deepen our friendship within minutes rather than weeks, months, or even years. In sum, a game where each person has to answer the question truthfully, but is not required to reveal what the question is. The catch is that if the person decides to conceal the question, they have to take a “punishment” (i.e. crazy hot sauce, disgusting foods, durian, Beanboozled jelly beans, etc.). Before they decide to or not, other participants can ask clarifying questions, as long as it’s not “Is X the question?”, and bet additional units of “punishment” if the answeree chooses to conceal the question. Of course, if the answeree does reveal, the people who bet will take the “punishment” instead.

Some references:

What’s changed?

After over 30 sessions in the past 3 months, a few things have been hotfixed since the in-person game:

  • One-time perishable links – While not the be all end all, vua.sh lets us create a “secret messages” where only the people with the link can access the question – and only once. Once the link is opened once, it’s dead. So, this gives folks a peace of mind knowing that no one can go back and find out what the questions are. The people who create these questions are the last group/individuals who play.
  • One-slide Powerpoint presentations, reminiscent of Jeopardy, with increasing risk/depth factor of questions, scaling punishments with question difficulty/depth.
  • Mailing the “punishments” to the people I’m playing with, like Sean Evans and his team does for their show, Hot Ones, where they mail their 10 hot sauces to their guest before the interview. This way, I can keep people accountable to the punishments
  • Zoom, or an equivalent web conferencing tool – Social distancing at its best. Even better now, ’cause I get to play with people outside the Bay Area as well.

The five lessons I learned

  1. Total conversation time virtually = 100%. Total conversation time in-person > 100%.
  2. First answer makes a difference.
  3. For group calls, preface with introspective intros.
  4. The “extroverts” take over.
  5. Take the bio break.
Continue reading “#unfiltered #39 Five Lessons from Trying to Engineer Serendipity in a Virtual Environment”

#unfiltered #17 My Favorite Questions from Social Experiments – On Love, Emotions, Candor, and Goals

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I’ve given myself the last two weeks to focus on introspection. Rediscovering cross sections of my life – crystallizing them in amber – to find where I can improve the most in. And in the process of doing so, I found inspiration in. I’ve known for a long time that I was, by no means, the smartest person out there. Arguably, my best ideas find the roots of their ‘originality’ in insights from others. From…

  • Friends
  • Founders
  • Investors
  • Subject-matter experts (SMEs)
  • Podcasts
  • YouTube videos
  • Academic journals
  • Blogs
  • And, really creative and really, really passionate people, where their passion is contagious.

… just to name a few.

But, that’s the best part!

Though it wasn’t my initial intention to do so, some of my favorite, most curiously introspective, most thought-provoking questions came from my guests during social experiments, particularly those who partook in Brunches with Strangers and Hidden Questions. Frankly, I can’t take credit for any of them. And just as I learned so much about them and myself from each, I hope you’ll be able to do the same. I don’t expect every question to resonate with you, but I suspect at least a small handful will. If so, my only ask is that you pay it forward in your own meaningful way.

Between 120+ guests between the two of the experiments, here are some of my favorite.

On Love and Emotions

  • When was the last time you said “I love you”?
  • When was the last time you wished you had said “I love you”, but didn’t or couldn’t?
  • Who was the last person you lost in your life that hurt you deeply (i.e. breakup, death, loss of friendship, etc.)?
  • When was the last time you uncontrollably cried?
  • When was the last time you genuinely smiled?
  • What emotion have you given an overemphasis on in the past year?
  • When was the last time you were disappointed in yourself? Why?
  • When was the last time you looked yourself in the mirror and thought “I’m killing it”?What might have sponsored that emotion?

On Lack Thereof

  • Is there someone you pretend to like but don’t? If so:
    1. What is stopping you from sharing your thoughts candidly with them?
    2. What is stopping you from liking them?
  • How many friendships do you regret having broken and never healed? Why?

On Candor to Others and Yourself

  • What are 2-3 things you look for in a person/friend before you are comfortable sharing a secret? How would you prioritize those 2-3 traits?
  • What are you dishonest to others about?
  • Why do you lie to yourself?
  • Over the past year, what have you gotten better at saying ‘no’ to?
  • What are some contrarian beliefs you hold deeply to be true?
    • (Also seen asked as) What is an unpopular opinion you have?
    • Who have you told? Or have you told anyone else?
  • If you could pass 1 value/trait down to your child(ren), what would it be?
  • If there was 1 trait that you could prevent your child(ren) from taking on, what would it be?
  • What is an unusual habit, or an absurd thing you love?
  • What is the best lie you ever told?
    • Do you believe it?
  • What is the most hurtful comment you once said, wrote, or expressed to another?
  • How often do you log on or log off of social media due to envy?

On Goals

  • Do(es) your long-term goal(s) scare you?
  • What’s the craziest thing you did for X?
    • Let X be any goal you’ve once had (i.e. job, relationship, family, grades, to learn, etc.)
  • What is something someone once said to you (good or bad) that keeps you motivated to this day?
  • What failure has set you up for success?
  • If you could title your own biographical movie, what would it be called? And what will it be called post-mortem?
  • What is your 10-year goal?
    • What’s stopping you from accomplishing it in 1 year?
    • If I held you at gunpoint, and told you that you had to reach this goal in 1 month, what do you have to do, starting from now?
  • If you could undo one decision you made in the future, what would that be?
  • What would you like to have written/said in your eulogy?

Photo by Nijwam Swargiary 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.


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