Toucan co-founder. Lover of startups and travel.

Current status: One out of two ain't bad.

Last week I promised to talk about modalities, and I’m holding myself to it. It might sound less interesting than princes and drag queens, but stick with me. It’s not something anyone’s talking about, and it 

Let’s start with what “it” is. I know “work modalities” sounds like the topic of some dreadful MBA lecture, but I don’t know what else to call them. (If after reading this post you think of a better term, please let me know 🙏🏻.)

Think back to two years ago when things were normal and most of us worked in offices…
You check your schedule and you notice you have a budget meeting in the Star Trek conference room in 10 minutes. You get up, go to the kitchen, make yourself another cup of coffee, and make your way over to Star Trek.

You walk in and your colleague Joe is already sitting down at the conference table.

I’m dreading this meeting. Our PR firm wants us to double our spend and Carl is going to be pissed.

You’re fine. I have to tell him we need to spin up a hot backup data center to pass our continuity audit. When he hears those numbers he’s not going to give you a second thought.

Oh my God. A complete nightmare. Last night she chewed up my favorite pair of running shoes. Almost ended up with a dead dog.

They get over it. Has she at least stopped peeing all over the house?

Carl walks to the head of the conference table, plugs his laptop into the projector, and pulls up the budget spreadsheet.

So we’re all agreed? Get me your revisions by end of day and we’ll go through this again tomorrow.

Damn, I’m late for my one-on-one with Sally. Gotta run. Hey Mary, we still have lunch at Papa Leon’s?

What did we just witness? A completely normal meeting, broken up into three parts. Before Carl walked in, you, Joe, and Mary were 

. After the meeting started, the four of you were 

Now, I want you to fast-forward to six months ago: everyone working-from-home.

You check your schedule and you notice you have a budget meeting in Carl’s personal Zoom room in 10 minutes. You get up, go to the kitchen, make yourself another cup of coffee, and make your way back to your home office.

You log into the meeting room and see a message telling you that the host will let you in momentarily. You turn off your camera. Mute. And check Twitter. Suddenly your reading is interrupted.

Good morning! Everyone here? Can you hear me?

Hi Carl. I can hear you. Can you hear me?

Carl shares his screen. No one turns their camera on.

The meeting ends. Carl closes the Zoom room. You Slack Mary: “What a d*ck!”. Mary Slacks back: “First class. I have to go. The dog just pissed under my desk.”

When you have one meeting like that after another, without the social breaks, it’s exhausting.

Traditional video conferencing platforms don’t allow that to happen. They’re optimized for work, even though socializing is an integral part of work. As we often say, Zoom is tiring because it lacks humanity.

If you’ve used Toucan you know it’s a completely different experience because we’ve designed Toucan to allow seamless transitions between all three modalities: 

. A typical meeting – like the one I described above – is what we call a modal sandwich: [socializing][collaborating][socializing].

Now, let’s consider a bigger event, like a company all-hands.

You check your schedule and you notice the company all-hands is scheduled in 20 minutes. You’re a bit surprised that this one is due to last three hours and wonder what’s up. The all-hands is in the auditorium, which is at the other end of the building, so you’d better get going. You stop by the kitchen to grab another coffee and run into Mary who’s also getting a fresh cup.

Good to see you too! Have you seen Joe recently?

You didn’t hear? We broke up. His wife found out about us. He told me it was over, that he was leaving her, but as soon as she started giving him hell for cheating on her he asked for forgiveness and went running back. I was so pissed off. I told him never to call me again. I hope I don’t run into him at the all-hands. It’s so awkward.

Oh Mary. I’m so sorry. I had no idea...

Don’t worry, I’m almost over it. Just not sure I’ll ever trust another guy again.

You and Mary walk to the auditorium in silence. As you pass other colleagues you greet each other. You walk in, and Mary grabs your arm.

Oh no, there’s Joe. I don’t want to talk to him. Come sit with me.

You walk to the other side of the auditorium, sit down, and start talking about your dogs.

Hey Joe! How’s it going? You heard the rumor? I hear we’re being acquired. That’s why this all-hands is going to be so long.

That’s the big secret. No one I’ve talked to has any idea!

Hey, did you see Mary walking in? Why didn’t she come say hi?

The lights start to dim. The CEO’s Chief of Staff walks up to the podium.

Good morning everyone. We’re going to get started in 5 minutes. Please take a seat.

Working together online is fundamentally different than working together in person because most online tools don't allow multiple modalities. Toucan does.

Work Modalities

We, the developers and designers and hustlers of Startuplandia use toucan almost exclusively for internal technical standup.

Is that because A. you all are massive hipsters or B. cause being better than zoom is apparently a low bar ?

Oh why I think it is a bit of both, yes, John D used to be a massive hipster (and has the single speed + cocktail bar to prove) and yes, toucan is generally better than zoom.

Well, how do you actually define 'better' ?

(Aghast) You want me to define my marketing-speak?

Well, in our specific use case (small technical screensharing sessions), we define better as...


1.	Toucan never crashes (Platform Stability +1 Toucan)
2.	Toucan plays a cool little sound of the rainforest when you start the session (Emotional Feedback +1 Toucan)
3.	Toucan has a visually clean interface (The iPhone of Video Tools +1 Toucan)
4.	Toucan has an excellent layout for monitoring self, others and the screen that others see when screensharing (Functionality +1 Toucan)
5.	Toucan rhymes with both "YOUCAN" AND "TWOCAN" talk about motivational (Marketing IQ +1 Toucan)
6.	Zoom has better audio AND video quality than google hangouts (Technical Attribute +0 cause who cares about hangouts)
7.	Zoom as a company is worth 90Bn ? (Irrelevant metrics +1 Wall Street)
8.	Zoom interface hasn't noticeably changed in over 2 years? (Is that even possible? -1 Zoom)
9.	Zoom has a pretty smart domain name, Zoom.us (Marketing IQ +.5 Zoom)


So after careful analysis, you see Toucan has 5 points, Wall Street has 1 point and Zoom has -.5 points. (Would you rather pay $0 for 5 points or 90BN for -.5 points? +1 Wall Street)

We'll let this "data" speak for itself, but if you want to see a more in depth discussion and demonstration of the above points, watch the below demonstration video to get a sense of what we are talking about.

An if the video wasn't enough for you, check out the below screenshot of some general developer feedback about using Toucan vs Zoom (I was actually shocked that everyone shared my sentiments as I'm usually the weird outlier)

Disclaimer: We know the people who built toucan, they are super smart engineers, smarter than us, we didn't write this post just cause they built toucan, we tried toucan cause they said it was nice, and yes, we agree, and then the founder of toucan asked us since we are strong users if we wanted to be in the newsletter, so this is some hopefully well placed content marketing. We also agree that if you want some boss product engineers (and designers) you should say hello@startuplandia.io

We are proud to publish our first guest blog! John Davison wrote a great piece on Toucan and it's differences to Zoom.

Toucan for Standups,  Good Bye Zoom

Today I was planning on writing about video modalities, but last night I watched a production of 

 that sent my mind down an unexpected path. Video modalities are going to have to wait.

 got me thinking about pseudonymity in a way I never had before. Specifically it made me consider what makes pseudonymity similar to anonymity and what makes it similar to a  verified identity.

Before taking a closer look at this I want to explain what it was about this 

Most of the roles were played by actors of the opposite sex. Prince Hamlet was played by a woman, as were Guildenstern, Horatio,  and Laertes. Ophelia was played by a man. Normally I’d expect this sort of affectation to distract from the play. It didn’t at all. In fact I barely noticed it. And that’s what surprised me most.

It wasn’t until today, on one of my early morning hikes, that I began to wonder why  Federay Holmes and Elle While, the production’s directors, had done this. I came up with three plausible explanations.

 explanation, and I came at it from two perspectives:

     1. Historical redress:  women were given the good men’s roles because they’d             traditionally been denied that opportunity.

     2. Gender fluidity: gender is subjective, so it objectively shouldn’t be a consideration.

Both of these seem trite in light of the play itself. The direction was too intelligent. The directors are true Shakesperians, so I dismissed this explanation.

explanation. In Shakespeare’s day all the roles were played by men. Having most of the major male roles played by women seemed like a nod to tradition with a modern wink. This seemed a bit more plausible.

The third plausible explanation was my favorite. I thought of it as the 

 explanation. Acting isn’t ballet. Roles rarely require physical characteristics only possessed by one sex. So maybe the directors just considered their troupe of actors and picked the one they thought best suited for each role, irrespective of gender.

I’ll never know if any of these three, or maybe even another, was the reason behind the aggressive transvestism. I’d rather not know, because it doesn’t matter.

 I’ve seen. The woman who played Prince Hamlet, Michelle Terry, was the best Prince Hamlet I’ve watched. It was one of those performances that will become a reference point for every Prince Hamlet I see from now on.

Believing that Michelle was the prince while I watched her perform made me realize that I’d given pseudonymity short shrift in my recent thinking about 

I argued that we didn’t know how to manage the evolution of etiquette in the face of anonymity. But pseudonymity is different. I think I finally understand how.

When an actor plays a role, his performance is pseudonymous, i.e., his words and actions are those of the character he is playing. From the audience’s perspective, the fiction lasts as long as the play. Had I been at the live production of the 

 I streamed last night, I might have gone back stage to congratulate Michelle for her wonderful performance.

Although I’d just spent two hours believing that she was Prince Hamlet, I would not expect to find Prince Hamlet backstage.

And although I’d just spent two hours believing that Prince Hamlet’s actions were both inevitable and justified, I’d be horrified to walk into Michelle’s dressing room and find her forcing her uncle to drink a fatal poison while stepping over her dead mother.

The pseudonymous fiction was time-bound by the play.

I have a soft spot for drag queens. When they’re good I have no problem believing they’re women and treating them accordingly. When they’re out of drag I also have no problem calling them by their real names and interacting with them as I would with any other men. The transformation is real but impermanent. And just as I expect Michelle as Hamlet to act like Hamlet, I expect Joe as Dollface to act like Dollface.

Neither Michelle nor Joe are anonymous. They are temporarily someone else. If they were anonymous they would be no one else. They would just be unknown.

It turns out is the critical measure of a pseudonymous performance. Time is more important than the quality of the performance itself. Time is the reason a pseudonymous individual is so similar to or sometimes identical to an identified individual. (I could go further and argue that an individual’s given name is nothing more than a pseudonym conferred by his parents but I think we’re far enough down this rabbit hole as it is.)

Plays and drag performances are easily time bound. Other forms of pseudonymity – particularly online – are not.

I spend a lot of time in what people call “crypto Twitter”, this is a collection of important people in the cryptocurrency space. Many of those people are pseudonymous, for a variety of reasons. Some of those pseudonymous Twitter accounts have existed for years. They have very clear personalities. Some of them are smart, and many are influential. Are those characters anything like the people behind them? Who knows. It doesn’t matter. What matters is that they are known and accepted as they are. They behave exactly as we would expect an identified individual to act. They are as bound by Twitter’s etiquette as I am.

Until my morning ruminations over the relationship of actors to their roles, I hadn’t appreciated the importance of time. It’s so obvious when action is live, but far less obvious when it takes place in digital space.

A pseudonymous account is anonymous on creation. Over time the pseudonymous personality becomes more and more real until it is indistinguishable from an identified individual.

In my earlier thinking about anonymity, I stated very clearly that I believed online worlds with anonymous actors could not be governed by etiquette. That’s not true for pseudonymous actors. I appreciate Shakespeare’s clearing that up for me, but now I’m faced with another conundrum: when is a pseudonymous actor old enough to be real?

Prince Hamlet considers the dichotomy between being and not being. While that is still possible from the perspective of the online pseudonymous actor, it isn’t possible from the observer’s perspective because the observer has to consider time. Pseudonymous characters are always in the process of becoming.

Thankfully, humans are good at managing ambiguity. Despite uncertainty, we muddle through.

Just as we’re grappling with consequences of online anonymity, we are grappling with the consequences of online pseudonymity. As someone who has to worry about providing environments where both might exist, I’ll continue trying to contribute to the framing and, with luck, solutions to these problems.

Shakespeare had something to teach me about online pseudonymity.

Shakespeare and Pseudonymity

I’d rather swim in the ocean than in a pool, but friendly oceans are rare, so I’m well used to chlorine. Everywhere I go, I look for a pool. This can be challenging.

Unlike a lot of sports, swimming culture varies from country to country. I don’t know why that is. Ski in Colorado, Switzerland, and Chile and the experience is rather similar. But being familiar with American pool culture doesn’t prepare you for a workout in Hong Kong, or Italy. Once I learned this lesson I started approaching swimming in a new country with as few expectations as possible. This turned initial frustrations into a mix of apprehension and excitement. Going to a new pool became a lot more fun.

I should point out that public pools are not tourist destinations. If you don’t speak the local language, prepare to be confused.

I learned to swim in America. My first and only coach was an ex-olympian at the University of Texas in Austin. I swam with her for two years. She taught me all the dos and don’t of swimming, or so I thought. I eventually discovered that I’d only learned the American rules.

Two that will surprise a lot of non-Americans: pre-swim showers and caps are unnecessary. You’re welcome to shower and wear a cap, but no one will care if you don’t. Why? Because Americans love technology.

The pool at UT was chlorinated enough to kill anything that might lurk on an unshowered body. Sometimes the levels were so high our teeth hurt. If you’ve never experienced that, it’s special.


My whole life I’d been told that hair damages pool water filters. When I asked my coach about it, she laughed. “Why would we use filters that couldn’t deal with hair?”

Australians take their swimming seriously. The first time I went to a public pool in Sydney it took me forever to get in. Lanes are organized by speed, and it was clear that picking the wrong lane would be frowned upon. They could have made it easy by being precise – this lane is for 1:20 swimmers, this one for 1:40, etc. – but instead they were just marked “slow” to “fast”. Despite the vague guidance, people knew exactly where they belonged. No one was passing.

I watched people swim for at least 15 minutes before picking a lane.


If you’re a Western swimmer, Hong Kong is a great experience.

The average age of swimmers is 90, at least. I never figured out what Hong Kongers do for exercise when they’re younger, but they don’t swim. Apparently, it’s a sport they pick up on their 80th birthday with great enthusiasm.

In Hong Kong the public pools open at 6:00. I’m the guy who always shows up before a place opens, especially if it’s for a workout. In most countries that pretty much guaranties I get a pool lane to myself, at least for the first half hour. Not in Hong Kong. At 5:30 the first enthusiasts show up. By 5:45 the crowd is thick with people gossiping and stretching. When the doors finally open, it’s a mad dash to the changing rooms. I think I’ve been to four pools in that country, and the pattern is identical. Hong Kong pool culture is strong!

I like to think I’m efficient. My swim gear is always well-organized and my pre-swim routine is simple. Despite that, I was never first in the pool. A group of spry 90 year olds always beat me to it. I’m a little competitive, and I was sure that one day I’d beat them. Swimming almost daily for three months, I never did.

After Hong Kong I was ready for Taiwan, or so I thought.

Swim caps must be worn at all times. No exceptions. But they have loaners, which is unusual.

The first time I went to Taipei I chose an Airbnb within walking distance of a sports center with a 50m pool. My heart sank when I was told I couldn’t swim in it without a special pink wristband. To get the wristband you have to pass an exam only given on Mondays at 8:00. If you miss it – which I did twice! – you’re stuck in the 25m pool full of people doing aerobic tai chi.

When I was finally allowed into the grownup pool I was almost immediately kicked out for using training equipment. All forbidden. No fins, no paddles, and no snorkel. But other people in the pool were using equipment! Baffling. I eventually found someone who spoke enough English to explain why. Those other people were part of a club and had applied to train. Of course.

Taiwanese lane rules are the opposite of Australia’s. People swim in any lane they want, at whatever speed they want. The lanes are marked, but it makes no difference. In the fast lane I had to deal with people who were literally practicing floating. Eventually I pretended it was an intentional obstacle course and made a game of it.

Japan is the most difficult place I’ve tried to swim. It’s so difficult that I failed to even find an open pool my first two trips there. It’s easy to find pool websites, but they are the opposite of helpful. In fact, I think they’re all purposefully misleading.

On my third attempt I asked two native Japanese speakers to help me out. They were as baffled by what they found as I was. Google Translate wasn’t the problem after all. They came back to me with information like “You might be able to swim in this pool on Thursday if the junior school isn’t using it. But it’s not clear.” I was determined to figure it out, so my letter to every potential Airbnb host began with “Is there a pool nearby and can you tell me when I can swim there?” One host finally got back to me with very precise information. She had gone to the pool to get it in person. I was finally in!

My first day at the pool was confusing. Shoe etiquette was complicated. I had to take my street shoes off before going into the changing room but was only allowed to wear my thongs (or flip-flops) up to a special rack that I of course didn’t notice. Wearing thongs up to the pool is not OK. After that first infraction I was pointed to a board full of rules I couldn’t read. I smiled and hoped I wouldn’t unintentionally break more.

By the time I’d sorted out my shoes I was thrilled I was finally going to get to swim in a Japanese pool. But before I was able to get in, everyone got out of the pool, and stood around. Five minutes later, everyone got back in. I eventually learned that this is perfectly normal. An hourly break is required.

The most wonderful thing about Japanese pools is their lane etiquette. Unique.

In most places – but not Taiwan – when you swim faster than the person in front of you, you tap their foot and they pull over when they reach the end of the lane. In Japan people pulled over in the middle of the lane, immediately. I was so surprised the first time that ran right into the polite swimmer in front of me.

But my very favorite experience was arriving at the end of a lane and having two or three women clapping for me. The first time it happened I thought I’d misunderstood, but it happened again. Women I would have passed on the return leg pulled over and clapped when I touched the wall. The men never did. They waited until they saw me in the locker room to say “fast” with a thumbs-up!

In Australia I fit into a slow-medium lane, but in Japan I’m fast. If you want to feel good about your speed, go to Japan


Swimming in Thailand is also different. Thais don’t swim. Bangkok has two 50m pools that were built for competitions and would be empty if it weren’t for foreigners.

Thailand is run by the military and the closest pool to my house was on a military science compound. Being saluted before and after a workout was always a thrill. Pageantry aside, we all know the military like rules, and Thai pool use doesn’t escape this culture.

In order to be allowed to take the obligatory swimming exam – a 100m swim,  1/10th Taiwan’s requirement! – I needed to get a medical certificate from a hospital. Once I had my certificate and passed my exam I could apply for a pool membership card for which I needed a passport photo, ID, and, of course, some money.

Every time I went for a swim I presented my membership card, watched the clerk record the number in a big book, and paid my entry fee in order to be given an entry ticket. The first time I put the ticket in my pocket and walked away. Someone followed me to make sure I put it in the right place. I didn’t of course and was confronted by a very worked up clerk when I walked out of the locker room. No one else in the pool was wearing a cap but I thought they might be members of a team and had gotten permission to swim capless, so I went back and pulled the cap out of my bag. That didn’t make the clerk feel better at all. Now I was stumped. Luckily an Irish guy was just finishing his swim so I asked him if he had any idea what could be wrong. He smiled and asked me if I’d put my ticket on the spindle between the office and the locker room. He knew.

The strangest pool culture I’ve ever encountered is definitely Italy’s.

Swimming caps are absolutely essential. Nothing will upset an Italian lifeguard more that someone trying to enter the pool without a cap. Last year my wife was told to remove her sun hat to make sure she was wearing a swim cap under it. They clearly don’t buy their filters from America.

Shoes can’t be worn into the locker room, like in Japan. Pre-swim showers and foot baths are required.

All swimmers are expected to own a bathrobe or poncho with a hood. A towel isn’t a suitable substitute. Those should be worn from the changing area to the shower area. I’ve never worked out why.

Swim suits must be worn at all times, even in the shower. I didn’t understand why until one day a woman walked into the showers looking for her son. Nobody thought it was strange.

, etiquette is wonderfully malleable and changes from place to place and over time. Pool culture is a good example. Rules and etiquette differ significantly from country to country. All of us building software need to keep this in mind.

If you’ve encountered unexpected pool cultures in other places, please let me know. I don’t mind surprises, but I’d rather be prepared.

Rules and etiquette at public pools throughout the world are surprisingly different. 

Pool Culture

, what got me there, and what got stuck in my memory. I also mentioned the ocean, Spain, Israel, Argentina, and Thailand. All of these thoughts and places are linked to works of art that had enough of an impact to get me on a plane. Sometimes I visited, and sometimes I stayed.

The only common thread to these stories was me. But what I didn’t talk about were professional obsessions. Today I want to tell you about some of the things that are pushing me to make Toucan the perfect embodiment of a new kind of profoundly human online interaction.

I’m obviously not doing this alone – I’m working with a very talented team – but I can’t presume to speak for everyone!

Socializing on video-conferencing platforms designed for one-to-one interaction is great. My kids are currently in 3 different countries. I’m in a fourth. If it weren’t for Facetime and WhatsApp, the long separations would be a lot tougher.

Other video-conferencing platforms are designed for business meetings and presentations, i.e., one-to-many interactions. Socializing on those platforms, to put it bluntly, sucks. That sounds harsh, but I say that with the greatest love for the many stalwarts – Skype, GoToMeeting, Meet, Teams, Zoom – that have made distributed work possible. I’m happy with daily standups and all-hands on those platforms, but I will not use them for anything even remotely social.

I don’t want to “hang out” with my colleagues in Zoom, I don’t want to talk to my cousins on Teams, I don’t want to attend a book club on Meet. Why? Because they’re not designed to support socializing. They aren’t designed for many-to-many interactions. When I get together with my colleagues to not-work, or my cousins, or my book club, we don’t all want to talk to everyone else all the time. We want to do what we do when we’re physically together: have conversations in small groups.

We started Toucan to solve this problem and to solve it well. Covid was the spark that engendered the idea, but that’s not what got me excited. (I assumed the whole Covid hysteria would be over before we shipped our first beta. 😂) I got excited because I have family, friends, and colleagues all over the world. I’ve never been able to socialize with them without getting on a plane, and I certainly haven’t had a way of inviting people from more than one location to an event.

That was a long way of saying: my nomadic life has created a problem I want to solve.

Another obsession of mine is learning. I’m a book learner. But I’m also an experience learner, and experiences almost always have a social element. So far we’ve seen the first sparks of people leveraging Toucan to provide a learning experience. One of our hosts has created a lecture series that allows people from all over the world to practice their language skills. Lectures are in English but then people break off into groups to discuss them in various languages. They are fun events because they attract so many different people.

A good friend, a playwright, has been writing “Zoom plays” that are performed online on a regular basis. They are delightful events, but I miss the social aspect of going to a performance. The audience shows up, turns off their camera and waits for the play to start. Some people say hello to each other and quickly realize how awkward it is to have a private conversation in front of dozens of strangers. When the play is over, everyone claps and presses the leave button. That’s not how I like to experience theatre! I want to arrive early and chat with my friends. At intermission I want to get a drink and talk about the play. And afterwards, I want to do the same. We still have some work to do to make live performances work well on Toucan, but the rest of the experience we’ve nailed, and I’m proud of that.

Going forward all teaching and cultural events will include a social element.

. For those of you who haven’t read my long post on the subject, my thesis is that etiquette is a critical emergent property of culture. Digital culture is brand new, and for a lot of reasons the idea of letting etiquette develop in that realm has been sidelined in favor of more aggressive options. I understand why. Problems arose quickly and had to be solved quickly. But those quick-and-dirty fixes are not good long-term solutions. We need etiquette.

Because Toucan does such a good job of supporting natural social interaction, we are seeing patterns of etiquette emerge. I won’t go into detail – that’s the topic of a future post – but it’s happening and it’s exciting. Because the medium is different, the etiquette patterns we’re seeing are different from those we use in physical space, which is to be expected. Toucan is turning out to be a laboratory for the evolution of digital etiquette.

I’ve always been lucky. Being able to work on a product that intersects with so many of my personal obsessions make me think that luck hasn’t run out yet! Toucan is my professional Kilimanjaro. It’s a mountain, a climb, and a series of discoveries. I’m enjoying every minute of the journey.

Obsessions are a prime motivator for invention. These are some of the obsessions that push my work on Toucan.

Toucan, My Professional Kilimanjaro

Antonia Hellman is a co-founder and CEO of Toucan.

She is a senior at Stanford University studying political science, economics, and management science & engineering.

Prior to Toucan, her career experience has been in data science and political campaigning.

I’ve said it before, and I’ll say it again: there are no more creative people in this world than teachers. Especially during pandemic time, when many of us may have taken a bit of a break to get our footing with this virtual world, teachers could not. Their jobs have never been easy, but COVID forced them to take even more onto their plates.

A reason why I have such a deep appreciation for educators is that I was fortunate to have been surrounded by brilliant, funny, caring, encouraging, passionate teachers growing up. One teacher that had a massive impact on my intellectual curiosity, empathy, and creativity is Mrs. Roxanne Feldman. And, funny enough, approximately 17 years after I first walked into her library, she is now one of Toucan’s biggest Superhosts.

Whenever I want to learn something new and cool about my own platform, I go to Mrs. Feldman. Ever since she got on Toucan late last summer, she has been coming up with inventive ways to engage her students virtually. For the past few months, she has been hosting “Toucan Tuesday” with the students in her homeroom to give them regular social interaction - a space to just hang out and have fun.

She loves that she can let her students socialize with each other without her being actively present in their groups. Because of Toucan’s speech rings, she can keep tabs on who is talking, if one person is talking more than others, and if a group’s energy is low. When she sees that a group may benefit from a bit of facilitation, she pops in and chats with them. And sometimes her students need a bit of alone time to finish an assignment or take a break; and that’s totally fine. On Toucan, you can socialize on your own terms, which suits all students’ comfort zones.

During Toucan Tuesday, students do a variety of activities. Mrs. Feldman and her students love collaborative games and projects. 

 is a favorite - where students take turns drawing and guessing different images. A new one that Mrs. Feldman introduced me to is 

 - an online painting program, where multiple people can work on the same piece at the same time. She has her students split into groups on Toucan, each group chooses a picture to draw, and they divide that picture into equal parts. Each member of the group paints one section of the picture, and they end up with a masterpiece!

Mrs. Feldman’s favorite part about Toucan is her perpetual space. She is one of a small handful of people both inside and outside our company that has a special space that is open 24/7, so she can host whomever she’d like on Toucan whenever she’d like - all by using the same link. She’s helping our team test this feature (it’s coming soon). She loves having her own home base within our platform that she can customize and call her own. Plus, she gives her link to her friends, so they can access it on their own when they need to rendezvous. It’s the perfect informal meeting place. Plus, it’s fun!

Attending school online is challenging, especially if you are in middle or high school. Socializing with others is actually a huge part of students’ educational experiences, and that has fallen to the wayside at a lot of schools. Mrs. Feldman is actively working to buck that trend. The world is lucky to have people like Mrs. Feldman out there, constantly thinking of creative ways to make children’s lives a little brighter.

Let us know if you’re interested in a perpetual space by sending us an email at 

, and we’ll let you know when the feature is available.

Since last July, Roxanne Feldman has hosted hundreds of people on Toucan and come up with the most innovative activities. Read more to find out how she does it!

Superhost Spotlight: Roxanne Feldman

I first saw Kilimanjaro 20 years ago. I was sweating in a banana plantation. The mountain was just there, improbably rising from the rich red dirt I was standing in. The summit was hazy and the snowcap could have been a cloud. The smell of the dirt and fermenting bananas are deeply embedded in my memory of the mountain.

The odd thing is that that couldn’t possibly have been the first time I saw it. I almost certainly first saw Kilimanjaro flying into Arusha, and I certainly saw it before feeling so small in that forest of banana trees. Memory is funny. Imperfect. What isn’t fleeting seems to be cemented by random shocks, unexpected encounters. In this case, the smell of rotten bananas and dirt.

I didn’t climb the mountain. I was with my 8 year old son. But I promised I would one day.

I’d seen Kilimanjaro before arriving in Africa, through Hemingway’s eyes. It was 

 that made me take the detour to Arusha in the first place. I don’t know what I thought I’d find there. Resignation? Sadness? A cold woman? Death? It didn’t matter. I had to go.

I am often pushed by an idea towards an object, or place. The despair and loneliness in 

 pushed me to Kilimanjaro. The masculin bravado in 

 pushed me to Madrid. A story about a viper biting a small boy pushed me to a kibbutz when I was just 16. A Borges short story pushed me to Buenos Aires. I stayed four years. The King and I pushed me to Bangkok where I might still be if it weren’t for a virus that pushed the planet into suspended animation.

After a year of confinement, I want to get out. I want to let myself be pushed by some of my obsessions. 

 is an old one that was resuscitated by all the hiking I’ve been doing.

I also want to get back to the ocean. I love the ocean. I love that the way we perceive it depends entirely on our perspective. From above, motion but no life. From below, tranquility and an abundance of life. A line from 

The ocean is a desert with its life underground

When I’m on the ocean I wrestle with perpetually moving mountains. Very rarely am I even reminded of the underground life. But when I’m in the ocean – swimming, snorkeling, or diving – I’m in another world. Motion is mostly slow. No sounds except for my own breathing, a constant reminder that I don’t really belong since I can’t survive on the volume of oxygen trapped in the water.

All creatures are driven by hunger but being driven by ideas is unique to humans. Which gets me back to Kilimanjaro.

In Hemingway’s day a climber could find a frozen leopard near the summit. It’s assumed that the leopard was starving and followed prey too far. Instinct likely told it not to follow, but hunger won. Hunger always wins. And so do ideas.

Ideas are latent action, movement or construction. In confinement all of my ideas are necessarily funnelled into building.

I’m loving building, but I long to move. I want to go back to East Africa, transit through London, sleep in Colonial style in Nairobi, fly over the African bush, and then climb. When I do, I’ll let you know.

In the meantime I’ll keep publishing blogs and watching where they’re being read. My 

 was read in America, the UK, Canada, Italy, Singapore, Bulgaria, Brazil, Switzerland, Chile, Latvia, Holland, Russia, and Ukraine. As I scan through the list I imagine getting on a plane to a city in each of these countries. It’s a funny way to travel, but it’s the best I can do under the circumstances.

I hope this one is read in Tanzania. I’ll be watching.

Ideas from art works often fuel obsessions that push me to act.

Kilimanjaro

Etiquette is important. It’s so important, so powerful it could save us. Save society.

I know that’s a big claim for something that sounds quaint, prissy. Even the word “etiquette” sounds quaint.

It conjures images of fussy Victorians tut-tutting because the young lady forgot to curtsy as she met her hostess. The oversight seems trivial, and the response priggish. If that’s all etiquette has to offer then seriously, why should we want any part of it?

But we’re using the wrong lens. Considering etiquette from a historical distance completely distorts its potential. It necessarily seems outdated. And why waste intellectual effort on an idea that is a priori outdated?

I want to suggest why we’ve got this wrong and why some form of pragmatic etiquette might be the key to release us from the slow-motion social car crash we find ourselves in.

Let’s take a step back for the sake of those who haven’t had the benefit of living in an etiquette-constrained society or, more accurately, people who don’t realize they’ve been living in an etiquette-constrained society.

And let’s also agree that we are dealing here with what I call pragmatic etiquette, an etiquette designed to oil the wheels of social interaction rather than arcane etiquette, a set of manners whose deliberate over-complication serves only the purpose of keeping the lower classes in their place.

With this pragmatism in mind, can we also agree that it is proper etiquette to refrain from farting when you walk into someone’s home? How do you know that? Because you were taught so (“It’s not polite.”) and if you ever forget, you are reminded (“Did you just fart? That’s disgusting.”). Etiquette governs this behavior, or in this case, behavior-avoidance.

We may find it ridiculous that anyone would remark on a girl forgetting to curtsy or a boy forgetting to bow, but we would certainly notice if someone let one rip in front of the Queen. Someday farting in public may be perfectly acceptable, and the oppressive prigs will be us.

The point I want to make is that this “no farting” rule isn’t written down. There isn’t a law against it. Police are not required to enforce it. This “rule” is part of good etiquette, which exists as part of our social fabric. Unlike more formal rules, most points of etiquette can’t even be enforced. They can only be encouraged by society at large. It is an emergent phenomenon, a set of rails for social behaviour that society creates out of necessity, for its own smooth running. And that tells you something about its importance… and by extension why its absence is so destructive.

When you dig into it, etiquette turns out to be a rather strange animal, an animal we don’t really notice until it disappears. But this is one animal whose extinction I truly worry about. When etiquette disappears we quickly witness the rise of something ugly.

Without these guardrails for our interaction and transaction we find other incentives to guide us: likes, follows, retweets, or simply our unrestrained selves. And at the other end we rub up against crude prohibitions: censorship, cancellation, vilification.

Which is where we are today. You don’t need to be a social scientist to recognise that etiquette is woefully absent from the digital sphere. If we don’t work to introduce it, or reintroduce it, we will be left with only two alternatives:

1. explicit, enforceable rules and
2. censorship.

Neither is likely to lead to a good end. Which is why, to politely hammer home my point: I believe etiquette can save us from this grim end state.

So here’s the big question: why did etiquette retreat from the digital sphere?

Etiquette works because social pressure is powerful. Anonymity changes that.

In physical life, true anonymity is impossible. Online, nobody knows you’re a dog.

Etiquette disappeared when online anonymity became possible. That’s where the poison got in. We first saw this on Usenet.

Usenet was the first distributed bulletin board on the Internet. It predated the World Wide Web. Usenet users were anonymous. People were far less polite on Usenet than they were face to face. This is unsurprising from today’s perspective, but at the time many of us were shocked. Removing social pressure to be civil immediately led to rampant incivility.

As a historical side-note, Usenet was used to share everything you can imagine, from technical data to child pornography. It was a free-for-all. It couldn’t be moderated because it was decentralized. For technical folks it was a critical resource so it was difficult to keep out of a programming shop. I administered Usenet for one of these shops on Wall Street where the CEO and I wrestled with the idea censoring this portal into an emerging Wild West. We ultimately decided not to, because we believed that would make us liable if anything illegal made it through. Moreover, people are so good at avoiding censorship that we knew we couldn’t do it effectively. Instead (and here I slap my naive forehead with my hand) we sent everyone a memo reminding them that downloading certain images could be either illegal or not “work-appropriate”. We also reminded people that they should be polite when interacting with others on the system. The memo stated that interpersonal etiquette applied even in the face of anonymity.

Were we successful?

No, we weren’t.

As technical people got used to non-existent social norms in the digital sphere, we saw the same behavior leak into the physical realm.

In the early days of technology conferences, being a female attendee was very difficult. They were objectified. They often weren’t taken seriously. Companies like Oracle attracted crowds by staging boxing matches between barely-dressed women. Booth-babes – as they were known – were never engineers. This behavior was very much a product of its time. If you’ve watched Mad Men you know exactly what I mean.

If the behavior I witnessed had been constrained to male braggadocio and silly stunts in an effort to “charm” women, it wouldn’t be worth a mention. But things were much worse. A large percentage of the attendees were engineers whose primary interactions were online, anonymous. They knew nothing about the etiquette that governed how far a man could go to attract a woman’s attention. The line between silly and offensive was crossed regularly. Women were insulted as if they weren’t present. Women were touched. And, for the most part, nobody said a word.

Because it became clear that etiquette no longer governed people’s behavior at these technology events, organizers were forced to publish “codes of conduct” so that attendees knew what behavior would and would not be tolerated. These codes are still with us today, more popular than ever. The problem with these codes is that they need to be enforced.

When people don’t follow the rules, they are banished, and often blacklisted. The process is arbitrary and sometimes unfair. A bad result for everyone.

Anonymity, then, led to the disappearance of etiquette online, which in turn led to problematic behavior in physical space.

“Codes of conduct” were introduced to replace the now-missing social constraints imposed by etiquette in physical space. Something different happened in the digital realm.

Usenet’s laissez faire didn’t last long. As bulletin boards centralized they were moderated for illegal activity.

Surprisingly, moderation was limited for a long time. Like me and my old boss, moderators feared that anything but a light touch would expose an institution to liability. But as publishing platforms became more powerful, fear of litigation diminished, and public outcry more strident, moderation became more aggressive.

Moderators – censors really – started by suppressing the distribution of illegal materials. Complying with the law is sensible. But they eventually began suppressing offensive materials and finally untrue materials.

The problem with this progression is serious. Over time the censorship trigger has become more subjective. Censors in this case are both judge and executioner, i.e., they determine whether or not something is illegal-offensive-untrue, and then eliminate it.

But even “censorship”, it turns out, is the wrong term. It often isn’t just speech that is eliminated but also authors themselves. They are banished from the digital world they inhabit. For many it’s their only world, both professionally and socially. We call this digital ostracism “being cancelled”.

The ancients banished undesirables from their city-states, a fate many considered worse than execution.

Because we couldn’t replicate etiquette in our digital world, we replaced it with a barbaric practice many of us thought long-buried in the past.

This all sounds grim. Is there another way?

In retrospect our old-fashioned-sounding etiquette seems rather wonderful. It guides behavior with gentle coercion. No written rules. No police. Even the elasticity of etiquette is a wonder. Etiquette differs from place to place, and even changes over time. As society evolves, etiquette evolves along with it.

We need to replicate this in our digital worlds. We don’t yet know how to do this generally, so we will have to try different approaches, one platform at a time.

Before we wrote a line of code for the Toucan platform we decided not to allow anonymous attendance at our social events. I thought this was somewhat cowardly, but my co-founders couldn’t see how we could avoid introducing heavy-handed platform-based moderation if we allowed it. In hindsight, they were right to insist on verified identities.

The problems that anonymity introduces are still too thorny. Our primary goal is to enable virtual events that are better than physical events. If etiquette is the foundation of physical social interaction, it also needs to be the foundation of virtual social interaction.

In the physical world a party host has the ability to expel someone who fails to conform to accepted etiquette. As I mentioned earlier, this differs from place to place. We, as a platform, cannot judge what is and is not acceptable, but our hosts can, so we have given them the ability to expel guests from their events.

It is not our place to make those kinds of local judgements. What may be unacceptable at a mixed-gender Stanford party may be perfectly acceptable at an all-male Maasai circumcision retreat, and vice-versa. No single platform “code of conduct” could be devised for both. No “safety team” (our Orwellian term for today’s digital censors) could possibly know what was and was not acceptable in both environments. The idea that they could is bizarre.

We are lucky. Because Toucan is a social platform, and because we do not allow anonymous attendance, we can expect etiquette to moderate behavior. Our goal is to encourage this and provide everything hosts and attendees at our virtual events need to make this possible.

We expect that virtual event etiquette won’t perfectly mirror physical social event etiquette. That’s OK. Humans are flexible enough to deal with both.

One final thought about anonymity:

We know it introduces unexpected complexity. As a society, we don’t yet know what etiquette looks like in that context. We, at Toucan, have decided not to try and solve it. But we believe that anonymity and etiquette are compatible.

Societies evolve slowly. Digital societies have emerged in the blink of an eye and we haven’t yet adapted. I think we will, but it will take time. I hope I’m right because codes of conduct and moderation are not acceptable substitutes for etiquette.


Special thanks to my friend Richard Newton who’s editing made my messy thoughts coherent.

If we can't develop virtual etiquette we're going to be stuck with moderation. Moderation leads to censorship and banishment.

In Praise of Etiquette

I hike a lot, mostly in the mountains. Fog can roll in unexpectedly, very quickly, and completely blind you. It happened to me today.

I left my home in bright sunshine. Actually, it was early, but it looked like bright sunshine was on its way. Very few clouds. I hiked up a mountain through a thick wood I didn’t know. That was the easy part. It was just straight up.

When I got to the top I was almost instantly engulfed by fog. I had two options:

1. take the same path down or
2. walk across a set of connected plains and another path down.

Naturally, my original plan did not involve taking the same path down. I know this area well, and I thought I could find my way across the plains, despite the fog.

Hubris.

I set out in the “right” direction and found myself going down a hill into a steep valley I didn’t recognize. I retraced my steps and set off in a slightly “righter” direction, or so I thought. Within 15 minutes I ran into a long cow fence I didn’t recognize. At that point I knew I was lost.

Despite being lost, I had a plan, and it was clearly time to execute it.

When I was younger, I never had a plan. I frequently got myself into less-than-sensible situations. Growing out of recklessness never happened. Even after a few kids my behavior didn’t change. Some day it was bound to end badly.

The thing is, the behavior wasn’t the problem. We make calculated risks all the time. The problem was my lack of rigorous what-if thinking before taking the risk.

This changed a few years ago, and it served me well today.

My father-in-law is an avid surf-skier, and he’s taught me the basics. After spending months just learning to stay on the ski, I began creeping out into the ocean, farther and farther. What could go wrong?

I should mention that my father-in-law is ex-Navy, so what-ifs are part of his DNA. When we’d get out a ways he’d often stop and ask me questions like: “If you lost your paddle, could you swim back from here?”, “If the wind picks up, can you paddle back?”, “If a shark takes your rudder, do you have a plan?”

The answer to that last question was always “no” of course.

Today, when I found myself surrounded by fog, I knew it was a somewhat dangerous situation. My neighbor recently saved someone who got lost up there and broke his leg. Dumb luck he’s alive today. With that story in mind, I worked through my what-ifs.

Each time I set out I made sure I could get back to where I started. Luckily the sun was strong enough that one part of the fog was brighter than the rest. I used that to keep my bearings, along with snow patches and rock formations. And each time I set out, I stopped when I wasn’t sure I’d find my way back if I went any further.

After two attempts at navigating the plain in near complete blindness, I decided it was time for the backup plan. I went back down through the woods to get out of the fog and eventually followed the mountain to a known spot. This took much longer than I expected, but the whole time I knew I was safe.

After three hours, I was home.

If you’re a regular reader you know that I like to draw parallels between my everyday life experiences and my work building Toucan. A few weeks ago I wrote about how customer acquisition is a lot like building and managing a fire, a rather heavy-handed analogy. 😂

Today I’m not going to bother.

What-if-ing an unpredictable situation is obviously a smart thing to do. It doesn’t matter if it’s a military attack, a strategic corporate bet, or a walk in the woods. It’s difficult believing it’s worth the time, but I’m now convinced it is. It’s taken me a looooong time to learn this lesson. Today I’m happy I did.

Getting lost is fine, as long you're prepared enough to find your way home.

If you are looking to be inspired to be a better Toucan host, look no further. Kae Huynh (EnterpriseGuy) is a Superhost in every sense of the word. He was an early adopter of Toucan last summer, he is a regular at our weekly socials--so he finds out about our newest features before anyone else--, and he throws tons of events for his communities on social media.

EnterpriseGuy made a name for himself in the Bay Area for hosting in-person events and meetups. Networking is what he does. And when COVID-19 hit, he had to take everything virtual. With traditional video conferencing tools, finding the same engagement as what he had in-person was challenging. But then he was introduced to Toucan.

Since the summer, he has hosted several events for his LinkedIn communities. These events started with his “🎉Networking Parties🎉”, where anyone connected with him on LinkedIn could join just by clicking the link. Over time, he picked more specific audiences, such as software investors.

When asked about what both he and his guests get out of using Toucan to network, he said, “My audience are investors. So they come in and they want to meet other investors, and it's very easy for me to present ideas...And they can do that in every other bubble, too. So I think that's been an amazing social use case that helps me, as an influencer, business operator, investor—whichever—build up my network, build up my business, engage with my audience, and try to continue to do what I do.”

One of EnterpriseGuy’s favorite things about Toucan is that spreading the word is so easy. Once you’ve created your event, all you need to do to invite your friends, colleagues, and followers is post the unique link somewhere. “What I do is I create a simple event on Toucan, and that gives me a link. Then I take that link, I integrate it with my marketing, and then I send the marketing out...Then people come in and sign up for it, and we host the event.” It’s really seamless, and he emphasized how guests of all ages and technological skill sets pick up on how to use Toucan instantly.

EnterpriseGuy sees Toucan as being the next frontier for influencer engagement, and he’s the pioneer. It is not enough to just have a following; you have to create a brand, a community around yourself (i.e. EnterpriseGuy--except that one’s taken, sorry). Toucan is redefining what it means to be an influencer and pushing the boundaries of what’s possible for audience engagement. He puts it best, “this is one of the rising tools in the influencer stack. Because, as a host, you are an influencer. You just don’t know it yet.”

Building a fire produces anxiety, prevents procrastination, and ultimately brings joy. That's what customer acquisition is like.

Toucan x EnterpriseGuy

Not many people in my industry heat their home solely with wood. I do. I know too much about wood. I can tell what kind of tree it came from by looking at it, and I can tell how well it will burn by picking it up.

It’s cold where I live. I’m in the mountains. It’s windy, and it snows. I burn a lot of wood.

I use a big fireplace in the kitchen to keep it warm. I also cook there. In winter I work at the kitchen table. The previous owners of this house used to move their bed into the kitchen as soon as it got cold. I “upgraded” the house by installing a wood-burning stove that keeps the upstairs bedrooms warm-ish.

So I have two fires to manage, all the time.

Actually, I have three, but the third one is metaphorical: user acquisition.

What does user acquisition have to do with managing a fire? Not much, but the dynamics are oddly-similar.

For the record, I’m not a pro. I’m not a marketer or a salesman. But I work for a startup, where user acquisition is everyone’s job.

Managing a fire, especially at the beginning, is a near-constant source of anxiety. Do I have enough paper? Should I use cardboard? Is the kindling dry enough? Do I have the right sized wood once it gets going?

And at the beginning, a fire has to be fed constantly.

User acquisition is like that?

Yup, especially at the beginning. Am I capturing the right contact data? Should I send email? How often? Is my email annoying? Will they mark it spam? Maybe I should use social media. Will anyone pay attention? How do I get more followers? What about a blog? I could write a blog! Then people can read it on their own time. What should it be about? Signing up for our service? No, too direct. How about building fires? Hmm. Good idea 😉

You with me on anxiety?

Now let’s talk about procrastination. If you want to survive the winter in my house, don’t procrastinate.

Order wood in August. Lots of wood. Pile it up so air flows through it. Cover it in case it rains.

Every day, bring in enough wood before it gets dark. Don’t forget. We have scorpions and vipers here. They’re usually not in wood piles when it’s cold, but you never know. Daylight helps.

Remember I mentioned the anxiety of feeding the fire? You can’t forget. Keep checking. Feed it often at the beginning, then less often. And pay attention to air flow.

When I’m working, I have to set alarms. It’s the only way.

User acquisition? Same thing. Don’t procrastinate.

Setup all the systems you’re going to need to engage with your users. You need social media accounts, an email management platform, and a CRM. At the very least.

Send out email updates on a regular basis. Engage with your followers on social media. Don’t let them forget you! Write the blog post. Not tomorrow. Today.

The anxiety is useful. It’s necessary. It forces focus, and prevents procrastination. Maybe once you’re a pro, the anxiety goes away. I don’t know.

What I do know is that once a fire really gets going, once it’s producing enough embers to cook a chicken, or once it’s strong enough to burn a huge log all night, I feel very satisfied. I feel joy. I feel like nature is rewarding me for all the effort I put into her.

I also know that when the user acquisition fire finally gets going, once it’s self-sustaining, once I know – or at least think I know – that we’re delivering what users want, I feel very satisfied. I feel joy.

Unfortunately, this is where my fine analogy ends.

I never want my fires to get out of control. But if our user acquisition gets out of control and forces our ops team to run around putting out fires, I’ll be OK with that. Definitely more joy.

Burning Down the House

If you know me, you know I don’t like this new normal. I don’t like being told I can’t travel, eat out, or even have in-person interactions with friends and co-workers. There’s something profoundly inhuman about these restrictions. Most people agree, whether or not they believe the restrictions are justified.

I happen to belong to an extraordinarily privileged group because I work in software. In fact, by almost any measure, my professional life has gotten better thanks to Covid. And that’s true for all my peers. Most of us, I think, are happy for our work to continue being organized as it is, and some of us have been driving towards this for a long time, despite a lot of resistance.

I haven’t worked in a proper office since 2003. Almost 20 years. I hired my first remote developers in 1995. I was working in New York and the banks were absorbing all the tech talent. We only had a few recruiting advantages:

we let our developers wear anything they wanted,

in our library. At the time, even developers had to wear suits if they worked for a bank, and a lot of them hated it. And if they slept at work it was under their desk, not on a pull-out couch.
Despite our “perks”, we still had a difficult time.

One day I ran across a brilliant developer in Spain, and hired him. Our CEO thought I was nuts, and to some extent, he was right. This was before the existence of any software to support remote work. SVN – nevermind git – didn’t exist. Skype hadn’t been invented. We talked by telephone, and ftp’ed our work back and forth. We made it work.

A few months later I hired a developer in Australia, and another in New Zealand.

Since we didn’t have universal weather apps most of our phone calls started with a weather update. In the dead of New York winters we were always jealous to hear about the mild weather in Spain and the beach weather in the antipodes.

Over time the idea of distributed work caught on and stopped being so controversial, but most of the distributed work was either technical or low-skilled. Conventional wisdom said that a company could only be effectively run if the core team was in the same place.

Until a few years ago most VCs wouldn’t fund a company that wasn’t centralized in that way. As recently as last January a friend of mine, who happens to be a VC, took to Twitter to denounce the silly idea that distributed companies could ever be efficient. I like to remind him of this when he tells me about the deals he’s considering today.

First we distributed work. Then we distributed companies. Now we're distributing socializing.

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