#unfiltered #74 What If Events Were Story Arcs?

castle, story, boat

“Somewhere along the line is a voice deep within you that tells you exactly who you are; you just have to have the courage to do that. That’s what the journey of the hero is all about. You’re born into a world where you don’t fit in. You answer the call to adventure. And you deny the call. Then at some point you then set out on your path. You slay dragons, and you do all of that. At some point, you come face-to-face with not a god, but yourself. Somewhere along the line, you get it — your A-ha moment. Your elixir. And you go back to your ordinary world and share it with others. I think that’s the journey. I think that’s the privilege of being absolutely who you are — belonging to yourself and being brave.”

That’s the arc of every great story in the words of Viola Davis on one of my new favorite interviews with Sean Evans, where she shares the secret to the hero’s journey.

In the world post-pandemic, people crave connection. A desire to go from URL to IRL. Everyone lost those years. Something everyone from a first grader to a college student to a young professional entering the workforce to a retiree could relate to. And in 2021, there was a re-emergence of events. Well-intentioned and well-founded. We had conferences, coffee chats, happy hours, fireside chats, oh, so many happy hours, panels, tech weeks, and… did I mention happy hours?

Most events out there are a time and a place for a collection of people. They’re static points in time. Not even counting the full spectrum of event planners, many of the best event planners spend tons of times on what makes events special, but change more about the small bells and whistles of an event than the overall flow. There are very few who take leaps of faith. Even less true for the vast majority of events, where events feel more of an afterthought than something that is designed to start or end a chapter in your life.

As such, everyone found themselves left with a goodie bag including a surplus of events, a lack of focus and attention, and a lollipop of exhaustion.

So, I had a thought last year, greatly inspired by my team at On Deck Angels. Instead of trying to host an event a month, what would need to change if we could only do one event a year? What would we have to do? Hell, extrapolating further, what if we only did one event every two years? Three years? Every Olympic arc? Which led to the thinking around, what do we need to do to make this the most memorable event that anyone has ever been to.

You see, I’ve hosted and co-hosted small and large-scale social experiments, but it was always for an audience who proactively and voluntarily signed up for. They were willing to do things outside the ordinary. But could I apply the same learnings to events for really, busy people who crave intellectual challenges, and who have been to so many events, they might be jaded?

So, below was and continues to be my collection of governing thoughts around answering that question, which will only grow and refine this year. In the theme of my blogpost last week, the below may be messy. Disorganized. Chaotic, even. Hope not, but possible. You’ve been warned. But I do hope that you might find at least one of the below frameworks useful.

Metrics for success

Every event needs a North Star. When planning the Angel Forum, as well as future events, below are mine.

  1. Attendees go on a hero’s journey, revisiting Viola Davis’ words above. In other words, character development. The event should create opportunities for growth within the event itself.
  2. Every attendee continues to and is motivated to build friendships (as opposed to networking and purely transactional connection) after the event. If the event itself is the only reason for people to connect, but it does not give people incentive to after, it’s a failure (in my books).

For now, that means, not only the speakers and the presenters need to be curated, but also each and every person on the guest list. I have yet to figure out how to customize such experiences at scale, where each person has wildly different goals.

Narrative frameworks I use for events

To dig a level deeper, here are my frameworks for execution:

  1. Surprise and suspense — Surprise is when you relay information that the audience does not expect. Suspense is when you relay information that the audience is expecting, but does not know when it’ll drop. Suspense is how you keep attention. It raises expectation, but knowing when to deliver the news helps with creating a reality that meets or beats expectation. Surprise is, on the other hand, purely for creating alphas in this expectation-versus-reality model. It’s the main driver for overdelivering on a seemingly smaller, but still powerful promise. To do so, I find George Loewenstein’s 1994 paper on the psychology of curiosity super helpful. More on how the five triggers to curiosity influenced my thinking here.
  2. Candy versus the meal — A Malcolm Gladwell framework. Effectively, how people think and what people actually talk about are quite different. Candy is what people talk about. For example, if I were to talk about the recent Avatar movie, I’d talk about how amazing the motion capture and the CGI was. And in doing so, I’ve spoiled nothing. It tells you nothing about the plot, but it’s exciting to talk about. On the other hand, the meal is how people think. It’s the whole package, the whole story. The meal has to be well-worth the visit, but the candy is what gets people excited. More on that in a previous essay I wrote here.
  3. The audience must understand the rules of magic — This is a combination of the thoughts of Malcolm Gladwell‘s framework around tools and Brandon Sanderson’s three laws of magical systems. Give the audience tools to use at the very beginning of the event. It could be a framework for how to think about the event and every activity in between. It could be physical tools that they will employ throughout the event. And once you do, make sure your audience knows how to use those tools. Test them. Give them small, but easy case studies and questions. Make it easy. Don’t put them on the spot. And by completing that test, that satisfaction and joy will help motivate them to use it more later. As Sanderson’s first law of magic goes, “your ability to solve problems with magic in a satisfying way is directly proportional to how well the reader understands said magic.” More on my thoughts on Sanderson’s laws here.
  4. Plots — Like any good story, the narrative is governed by plots. The plot must thicken and build towards a climax. And it must be resolved by the end of the event. Leave little in the main plot to chance, but leave room for each guest to discover something extraordinary. Maintaining a minor amount of stress and uncertainty, while sharing examples and reminders of being open-minded to new experiences, goes a long way. Only after stepping outside one’s comfort zone can one grow.
  5. Always use the audience’s time in a way that does not feel wasted — Inspired by one of the greatest writers of all time, Kurt Vonnegut. I forget which lecture he did that I learned this from. But it’s always been a governing theme for what I do.
  6. End on an ending where the reader can imagine no other — No loose ends. Everything that is teased (whether the audience realizes it or not) needs to be resolved by the end. This might be a semi-controversial opinion among storytellers and creative professionals. But I’m biased. I like my stories to end with a bowtie.

In closing

As you might imagine, much of this is still incomplete. And I hope to share more as I continue down this path of exploration and discovery.

Photo by Artem Sapegin 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.

#unfiltered #60 There’s No Such Thing As Writer’s Block

writer, inspiration, ideas, creativity

Years ago, I remember reading somewhere, “Writer’s block is not that you don’t have any ideas. It’s when you don’t have ‘good enough’ ideas.” In my opinion, one of the greatest fatalities of the 2020s is not that people lack ideas. But people have a poor way of capturing ideas when ideas do come to them.

And in the theme of ideating in the busy world we live in today, I wrote a short thread earlier this week on the seven ways I capture ideas.

  1. I carry a physical journal almost everywhere I go. Personally opt for a nice, weighty journal that I can’t wait to write in (none of that spiral bound, thin page notebooks, but that’s personal preference).
    My favorite brands: Leuchtturm1917/ Moleskine
    Page density: >150 g/m2
  2. While I’m at it, a good pen. I prefer felt tip or fountain pen.
    Psychologists do say you tend to remember thoughts more if you physically write them out, over typing them out.
    For felt tip: Staedtler fineliners
    Fountain pen: LAMY
  3. Reserve a full page for every idea. Even if your idea is only one sentence, give it space so that in the future you can come back to it and flush it out. As the wise Ron Swanson once said, “Never half-ass two things. Whole-ass one thing.”
  4. Allocate at least 10 minutes to generate ideas. Even if you can’t think of anything for 10 minutes, sit through the whole 10. A few months ago, amidst a catch-up, a founder friend of mine – for lack of better words, a serial builder, having created more apps that I can count – shared with another friend and I something incredibly insightful about finding inspiration. “Not enough people give themselves bored time. To produce ideas, you have to give yourself time to be bored.” These days, I try to allocate 30 minutes of bored time.
  5. I have a whiteboard in my shower. Yes, I take shower thoughts seriously. In fact, this blogpost originated from a shower whiteboarding session earlier this week. I’m not really picky on brand here, since it’s just to get thoughts on a board as quickly as I can, but get rain-proof markers.
  6. Handwritten notes are notoriously hard to track. So, I have a 3-step process for this.
    1. I have a table of contents at the back of every notebook. Usually reserve 4 pages for that. In there, I write down, page #, title of each journal entry, and key/most thought-provoking content.
    2. By the time I finish each journal, I revisit the now-completed table of contents to highlight/circle what resonates with me the most from that table.
    3. A few months later or 1-2 journals later, I revisit the same table of contents, browse through what I highlighted/circled, and for those that STILL resonate, I port over to my Notion, which becomes more or less my evergreen knowledge/idea hub.
  7. When I’m completely lost or need inspiration, I find that the best way to generate ideas is to ask great questions. For questions on people and passions, I’m a big fan of Tim Ferriss and Sean Evans. For startup or VC questions, I love Harry Stebbings and Samir Kaji.
  8. As a bonus eighth tip which I didn’t include in the Twitter thread, if you are still stuck, I find the question “What is the most important question I should be asking myself today?” quite useful.

Some examples of things I write in my idea journal:

  • Startup ideas
  • New things I learned in the venture capital space
  • Blogpost ideas
  • Introspective thoughts
  • Phrases and vernacular that other people say or write that I really like
  • Great questions to ask myself or others
  • Recipes I come up with
  • Dreams
  • Riddles or puzzles
  • Short stories
  • Concept art

In sum, anything is fair game. The more I allow my mind to expand without constraints, the more I’m able to draw parallels between seemingly disparate data points and create new meaning. At least for myself.

In closing

I passed by another quote over the years, and the attribution escapes me. “If you have don’t have any ideas, read more. If you have ideas, write more.” I’d extend it even further by saying, when you have a deficit of inspiration, consume. Read and listen more. There is a plethora of content out there today. And they are all more accessible than ever – from books to podcasts to articles to videos. When you have a surplus of inspiration, produce. Write and do more.

Photo by Brad Neathery 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!

#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.
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