The 21+ Moments and Insights that Gave Multitudes Life in 2021

At the start of 2021, Multitudes was nothing more than a fanciful thought, an experiment that had gone on hiatus during the pandemic.

As 2021 draws to a close, Multitudes is a venture-backed company with a fully functioning product, a growing team, and a host of opportunities coming its way.

Yeah, I know. It's crazy!

I'm still scratching my head at how an idea that I had in an Uber over two years ago would grow and evolve to anything remotely close to this.

To get to this point, there was so much that had to go right: the right opportunities, the right collaborators, the right breakups. Yes, even breakups (yes, plural). The right coincidences, the right portents that seemed to tumble across my path by accident.

Knowing that fills me with a strong sense of gratitude.

Because I've never been so excited for a project as I am for this one.

I believe that we're on to something special with what we're creating. Something that will foster wonder, connection, and play in the world.

And the journey is just beginning.

In 2022, we'll be starting on some new frontiers: accelerators, a full round of fundraising, business experiments, new hires.

But before 2021 ends, we wanted to celebrate the journey so far. Below, you'll find the 21 (+) serendipitous chain of moments and insights that brought Multitudes to life this year.

If you're reading this now, in all likelihood, you were a part of this journey.

Let's start from the beginning.

#1: It all started with a question.

I’d just finished catching up over a dinner with one of my best friends – Viria. We were driving back to her apartment in an Uber, savoring a day that had been chock full of unplanned walks through parks, old book stores, and double features. After we’d swerved past an empty Tibetan restaurant, Viria – ever the entrepreneur – provoked me with a question.

“If you were to start a restaurant, what kind of restaurant would it be?”

“Something with dining in the dark,” I sputtered without hesitation.

"Oh that's interesting. Have you ever tried it?" she asked.

"No," I said. But I could vividly recall the first time I'd encountered the concept.

#2: One night, while walking through the streets of Bugis, I passed by a restaurant that was immersed in complete darkness.

Folding green panels animated the restaurant's facade, where there stood a stately-dressed man with his arms behind his back.

Finding his presence so arresting, I couldn't help but approach him to interrogate what lay behind him.

“Dinner starts in one hour,” he said, handing me a pamphlet.

The first thing that jumped at me was the eye-gouging price – $199. And then I saw the images that seemed to be shot with night vision goggles.

"So they're eating in complete darkness?"

"Why, yes," the man said. "When we remove sight from the experience of food, we short-circuit our brain's tendency to judge before tasting. This has the effect of sharpening our other senses – taste, smell, touch."

Though I'd ultimately opt to save myself $199, the concept of eating in complete darkness with a group of strangers stuck with me.

#3: As I drew out the logic for my choice, I started to see how the “Dining in the Dark” model could be applied to a context that I’d grown burnt out from: dating.

“What if this could be a way to meet cool people?” I continued. “You could bond with a complete stranger over food while your waiter facilitated."

"You could call it blind date," she suggested. A pun upon puns.

The idea tickled me, as it felt like far more preferable to dating apps, the dominant modus operandi by which people met. In the months since moving back to the US – and out of a long-term relationship – I’d dabbled in several dating apps, hoping to connect with people I otherwise wouldn’t have.

At first, it was fun. I swiped left and right with gusto, excited by the suspense of whether the ones I desired might reciprocate. And when they did – bang! I felt that hit of dopamine (and validation) surge through me after every match.

You are desirable, Manny. (Hurray!)

Doesn’t it feel nice to be desired? (Oh, yes it does.)

We’d then engage in some back-and-forth banter, texting late into the night. Whenever I got bored, I could just ghost or unmatch from them, freeing myself from the clutches of responsibility.

#4: I noticed the inner chatter that would run through my head as I evaluated people’s dating profiles, picking them apart with a blade that sharpened with every swipe.

Eww, what is this person wearing?

Another “sarcasm is my second language” person, seriously?

Are these fools pulling their bios from the same source?

The Office was not that great of a show, why are you claiming you’ve memorized full episodes???

The weird thing was that I continued to hear this chatter even when I wasn’t on the apps. I might cross people in the streets, overhear their conversations, and feel myself casting those same aspersions on people. People I didn’t know, that I couldn’t know from this single data point in their lives.

And yet, it was as though using the apps continued to feed this voice inside of me that wanted to judge, to project all my insecurities that I was a poorly-dressed, uncultured fool who occasionally went on Reddit to steal other people’s quotes for my profile and, occasionally, indulged in Office memes.

#5: In my heart, I knew that this was wasn't the person I wanted to become.  

In making these assessments on dating profiles, our brains are relying on the limited dataset of our past. No person has and ever will meet every single human being on the planet. Even of the people they have met and known, how much can they definitively say they know them when every person is a rich and changing repository of memories and dreams, of stories that might never see the light of day?

If you need any more convincing, just look at yourself.

That’s what Walt Whitman did. In the epic, “Song for Myself,” Whitman famously wrote,

 Do I contradict myself?

 Very well then I contradict myself,

 (I am large, I contain multitudes.)

And yet, even with this stanza etched in my mind’s eye, I continued to make the same mistake over and over and over again: I’d rush to judge, and then use that judgment to assess compatibility.

It’s a mistake that we see happen all the time in dating.

We seek to predict compatibility before connecting with a person, flying in the face of decades of relationship research that has consistently shown the same truth:

Compatibility isn’t a precondition for connection; it’s a result of it.

The things that we value most in relationships – respect, kindness, sense of humor – can’t really come through a 500-character profile.

So, I began to wonder: could this ‘dining in the dark’ social experience help us overcome this tendency?

#6: Determined to see how this "Blind Date" concept work, I tested the experience with my friends and family.

To test it, I would equip my (mostly) willing subjects with blindfolds. As they sat in the dark, I would play the role of waiter/facilitator, serving them food and prompting them with discussion questions.

"What was the first concert you recalled going to?"

"Who is a teacher that made an impact on your life?"

"What advice would you give your teenage self?"

The start of these experiments was always a little awkward. People would tip over their drinks, fumble about their food.

But the awkwardness would be accompanied by lots of laughter and hearty discussion. Days after trying it out, people would tell me about how it felt to engage with other voices in complete darkness. The darkness had helped sharpen their focus and attention. Unaffected by the gaze of others (and their screens), they could fully immerse themselves in the questions and responses, into listening, sharing, and playing.

Someone remarked that it felt like ‘learning a new style of dance to a song I already know.’ Every move felt novel, albeit strangely familiar.

#7: So I gave up...

Surely, there was no future to be had in in-person businesses – much less one that invited you into dark rooms with strangers.

#8: Several months later, an email for a "Creatives Workshop" arrived in my inbox.

Designed by Seth Godin, the program promised to help you build daily creative habits by bringing you into a virtual community with other creatives. For 100 consecutive days, the community was intended to help foster an ecology of talent, or “scenius” – ”a whole scene of people who support each other, look at each other’s work, copy from each other, steal ideas, and contribute ideas.”

#9: I almost didn’t enroll into it.

The program smacked of self-help books and lifehacks, something I didn't have much of an appetite for at the time.  

But then, the girl I was dating at the time broke up with me just before going into a major surgical operation.

All of the sudden, my life felt a lot lonelier – and I felt a strong need for community.

#10: So...I enrolled.

I wasn’t entirely sure whether I’d focus on developing the "Blind Date" concept. I had also been working on a novel and building my skills as an EDM producer, so I didn’t want to feel entirely boxed in to one craft (classic creative diva, right?).

Every day, we were to post something ‘creative’ on the course platform. The posts were a measure of accountability – as proof that you were following through on a daily basis. But they were also meant to elicit reaction from your fellow participants.

#11: For one assignment, I sketched out screens for a digital version of the “blind date” experience.

The screens were simple in their design, meant to illustrate how many of the elements of the in person context – the blindfolds, the facilitation, even the food – could be translated to a digital one.

Closely observing the rise of Clubhouse, I realized that audio-only conversational experiences could be engaging and viable. In removing the profile and image, this could function as a ‘virtual blindfold.’ The facilitation could then be automated by assigning turns (and set times) for each person to share, while a facilitator would read out a series of prompts to help drive the conversation.

This direction felt exciting. On the one hand, it retained and even improved on the requirements for the in-person experience – all without requiring people to remain in a pitch-black room. And, using technology, the program could be scaled in a way that the in-person version could not.

#12: A friend in the workshop encouraged me to test out the concept with other participants in the workshop.

With over 400 participants enrolled in the cohort – all of them remote – the workshop represented an excellent testing ground for the virtual concept. All were, in some form, seeking to make connections with people in the workshop.

Plus, I knew I didn’t need to write a line of code to create the experience. Inspired by the stories of other tech company founders who’d used non-scalable solutions to test their hypotheses (the DoorDash story, for example), I used a suite of tools – Zoom, text-to-speech software, and Google Slides – to simulate the experience.

For every session, I would pair people without their knowing. To create the ‘dark’ factor, I would ask both to change their Zoom names to the name of a letter and keep their video off at all times. For the facilitator, I shared a screen that contained the ‘interface’ along with pre-recorded mp3s for the questions.

Her name would be Carla.

#13: The first test sessions were full of mishaps.

There was so much disappointment that came every time that a question didn’t land; the anxiety that arose every time someone accidentally arrived with their video and real name still visible; the trickiness of managing an interaction based on turns rather than allowing for more fluid conversation.

#14: But then, I would receive an outpouring of unsolicited love and excitement after the sessions.

What struck me most was the depth of sincerity in the comments. These weren’t empty ‘rah-rahs’ or light words of encouragement. The experience had affected something deeply within them – and this was in its first iteration!

#15: Between February and April, I would run 73 test sessions with 65 people from the workshop.

Each weekend, I introduced new features and activities. Over time, this grew to include using actual blindfolds, applying voice modulation (though this proved technically untenable), and a more developed theme centered around the concept of the Multiverse.

#16: And so much laughter was coming out of it.

#17: I also took a major step to bring in the first-ever collaborator – my dear friend, Alison – to support with facilitating the sessions.

Together, we were able to push the limits for what could created through this format.

In the final weekend of the workshop, we gathered and reviewed all of the posts from the workshop of every person who was in a Multitudes session that weekend – that included roughly 90 posts for each participant (and we had 20 participants that weekend!).

We then selected some of the most impactful posts from each participant and, to their surprise, spent the entire session reading their work back to them.

At the end, we invited an artist from the workshop to do a perform a live serenade for them (either through poetry or music).

Being able to help facilitate these sessions was incredibly moving, as I was able to witness each participant feel deeply moved. “It’s the realest form of being seen,” one participant said. “Thank you for the magic.”

#18: With the wind of these successful tests behind my back, I felt empowered to take the step to formalize Multitudes into a software company.

I wanted to see how this could be transformed into tool that could scale to other communities. And that’s when I approached one of my best friends from Stanford, Anna – who also happens to be a rockstar VC.

“You should join the On Deck Founder’s Fellowship,” she recommended. “It’s designed for people like you trying to get your ideas out there.”

#19: When I perused the On Deck site, sure enough, all the keywords were there.

“Helps people start companies”

“Meet collaborators”

“Gain conviction in your next venture”

A handful of case studies were sprinkled throughout, featuring testimonials from first time founders who'd managed to raise significant sums for their businesses after participating in On Deck.

Still, I was skeptical; here I was, this idealistic artist-type who’d just emerged from a soulful – albeit intense – 100-day retreat with a bunch of other artists and was convinced that he could make this concept –promising as it was – into a successful company?

#20: Fighting through bouts of impostor syndrome, I applied to the Fellowship – and got in.

This was a landmark moment for me, one where I felt that now, with my foot in the door, I could make shit happen.

As anticipated, I was very much one of the outsiders of the Fellowship. Though, a significant insight from the journey was that being an outsider wasn’t such a bad thing after all. In many domains, my naiveté paid off.

#21: As with the Creatives Workshop, I continued running Multitudes sessions to connect people within the cohort.

I did this partially to collect more feedback on the experience. But there were other, less obvious reasons for running them.

#22: The first reason was that I just genuinely enjoyed listening to the output.

There was something delightful about listening to two complete strangers chatting over a call with no agenda other than to just mess around and engage in all sorts of playful banter, musing about the universe, the nature of consciousness, pretending to be giants and aliens.

I would often find myself breaking into fits of laughter when they both learned who was on the other end of the call at the end of the experience, their reactions full of a surprise and befuddlement. These sessions amused me so much I went out and published them as podcasts (with the participants’ consent, of course).

#23: And...I wanted to put my bat signal for other potential collaborators.

Within On Deck, there were two types of people:

1. the "Builders": those, like me, who already had committed to an idea
2. the "Explorers": those who were open to joining a venture.

The hope was that a taste of the experience would arouse enough interest from the explorers out there. I knew I needed help, a partner in crime, the technically savvy, snarky and enterprising Tony Stark to my heartful, quixotic and perhaps overly sincere Steve Rogers.

It was a longshot.

Some might even say improbable.

But boy, oh boy, was I lucky.

#24: First, I found Josh Benjamin.

From the start of the program, Josh and I just kept virtually bumping into each other. We were ‘randomly’ grouped in the same breakout rooms, the same pairings in the 1:1 Gatheround socials. The same Mastermind.

As we began to hang out more and more, a synergy became apparent. On the one hand, there was Josh, an ex-Apple engineer (and diehard aficionado), who’d been an entrepreneur for the better part of a decade, and also happened to be deeply into authentic relating games, non-violent communication, creating playful internet experiences – and offering up surprisingly thoughtful gifts.

#25: One afternoon, Josh sent me a text that simply had a link to download an app in test flight.

Thinking that he was merely referring me to an app that one his friends had made, I chose to ignore the text. A little while later, he called me to insist that I download the app at once.

“Okay, okay,” I said, after which he promptly hung up on me.

When I opened the app, I was thrown into an audio chat room where I heard a strangely high-pitched, chipmunk-style voice.

“All right, it’s working!”

“Josh? Is that you?”

“Yeah! Let’s sing chipmunks songs now!”

(Okay, he didn’t actually say that last part. But, in all fairness, it was him and his girlfriend later joined the call to sing a near-perfect rendition of “Blue Moon” which, in chipmunks voice, sounds absolutely precious!)

And then, I realized what this, in fact, was: a cofounder love letter.

#26: Following the conclusion of the Fellowship in August, I worked with Josh and the second significant collaborator I met through the program – Rnjai Lamba.

Half-monk, half-brilliant programmer, Rnjai proved to be one of the most generous people in the On Deck program.

Every day, he seemed to make himself available to anyone who was looking for technical support, whether it was scoping out the technical requirements of their projects (like mine) or providing thoughtful feedback on their experiences (also, like mine).

After his visit to the Multiverse, I could tell that he was intrigued by intent behind the experience – as well as the technical complexity it would take to create a coded version of it. It didn’t take much convincing for him to take me on as one of his first clients for his development shop.

#27: With Rnjai's, Josh’s, and my powers combined, we endeavored to build out the software for Multitudes.

To build it, we employed a “hacky stack of tools” to develop the application, iterating upon a series of slides that mapped out every single aspect of the experience.

And when I say every aspect – I mean every aspect. Having never built out a fully functioning web-based application, I was unaware of the rigor that went into designing for as many “edge cases” as possible. What if the user became disconnected? What if they clicked refresh while they were in the room? What if they arrived early or late? And then there was the issue of how to ensure that Carla spoke synchronously for both participants.

All of these questions and more, we had to carefully consider, deliberate over, and in some cases, lost our hair over.

#28: After three long months of coding, testing, and iterating, we had a fully functioning product that we could bring out into the world.

With the product, Josh and I began experimenting with it in as many contexts as possible: in connecting our friends, in virtual parties with strangers, in dating, in team socials.

With every experiment, we gained more insight into how this experience could – and couldn't – function as a way to create meaningful connections and build community.

On behalf of 'Carlaton' and the team, we wish you all an auspicious start to 2022!