Hi Chris. Thanks for doing this with us. You’re best known as the Godfather of the Hashtag. However, can you briefly tell us who you are and what have you been up to till this point?
I think of myself as a social technologist and product designer. I studied communication design at university and have worn many hats over time — from running a consulting agency to working for big tech companies like Google and Uber to building several nascent internet-elevated communities (co-working) and events (BarCamp). Last year I left Silicon Valley and gave over two dozen talks around the world about where we’ve been with social media and where we are now, and where we can go with synthetic media and artificial intelligence if we humanize founder culture.
Let’s go through your design journey. How did it all start?
Early on I was much more of an artist — drawing comic book characters, painting, sculpting… art was something I was pretty good at from a young age. But then I discovered computers and loved their logic and how they offered technical puzzles to figure out. By the time I got to high school, I realized that I could combine both of those interests in the emerging field of web design — and became hooked.
I ended up designing and programming my high school’s website and after a summer working as an intern at a graphic design shop (mostly doing bindery and scanning hundreds of ads for a massive cookbook to raise money for a convent!), landed a job at the first web design company in New Hampshire. This is where my love for the internet got its start, and since then, I’ve wanted to share the empowering and connective aspects of this platform with the world.
Before we get more deeply into your life, I have to ask about the hashtag! I’m sure you told this story so many times, please share it with us. How it all started?
Some might think that the hashtag started with a single tweet, but technically the hashtag started with months of research which I gathered on the Twitter Fan Wiki (which I started and maintained at the time) and then wrote up into a proposal on my blog. The famous first tweet, therefore, was actually intended to get feedback on the concept — some of which was quite mixed!
The day after I published my 2000-word proposal, I walked into Twitter’s headquarters in South Park in San Francisco and shared it with Biz Stone, one of Twitter’s co-founders. He was somewhat dismissive because, frankly, they had other priorities to attend to at the time (i.e. servers on fire, etc). But I wasn’t to be deterred. Instead I decided to reach out to the nascent developer ecosystem building apps on Twitter’s API and started to recruit app developers to my cause.
Since there was already a way to call out other Twitter users (i.e. with the @-mention), it seemed reasonable that there should be a similar convention (with a different symbol) for topics, to make Twitter more personally relevant to each user. That is, if you could follow a person to get their updates, why couldn’t you do the same for a topic or event?
And so I pressed developers to change to their apps to add links to “tags” (words or concatenated phrases) that were prefixed with the pound symbol (#) to find other tweets that contained the same tag.
Since there was already a way to call out other Twitter users (i.e. with the @-mention), it seemed reasonable that there should be a similar convention (with a different symbol) for topics, to make Twitter more personally relevant to each user.
Over time, as people realized that this mechanism was a useful and easy solution to bring visibility to their tweets or to find other people posting similar content, the use of hashtags took off — and not just on Twitter, but critically on Instagram as well, where users of the photo-based service needed a way to add more metadata to their photos so they’d more easily be found in search results.
To this day, my favorite aspect of the hashtag is that it works anywhere that people can compose text — both online and off. The hashtag was developed in an era when many of us who were early to social media wanted to create interoperable standards such that a user of, say, Facebook, could message or interact with a user of Twitter, and so on. Email worked this way — and we wanted social functionality to be a feature of the web, not limited to a small number of websites. Thus the hashtag was intended to label content on all networks — not just Twitter. And so the fact that the hashtag is now supported on every major social platform is a testament to that original aspiration.
Considering contemporary usage of the hashtag — I’m both encouraged and hesitant. There’s so much newfound power in the use of social media to learn and discover what’s happening in the world. But we’re still learning how to cope with such fast access to so much information, often without local context or understanding, which can accelerate misunderstanding, expose bias, and sow disconnection. At the same time, such exposure can galvanize support and build cross-cultural empathy. Consequently, I would much rather the use, adoption, and promotion of social media and the hashtag persist, and that we do more to prepare and condition people to participate in this new medium effectively and pro-socially.
In 2010 you took a job at Google. Why did you decide to join them and tell us about your role?
I ended up at Google for a couple reasons: to learn, to influence, and to grow.
I was at first quite skeptical about joining a large company like Google, but I’d also reached a point in my career, having founded my own consulting agencies, and worked with startups, where I felt like I needed the experience of working in a big company like Google to teach me how it operated, what the benefits of working for a big company are, and of course, what are the drawbacks and challenges. The paycheck was certainly nice, but the Google lifestyle was also all-consuming. The reasons they provide busses to campus and free food are now well known. Still, I was working with some of the brightest engineers and product people on the planet — and it was impossible not to see the limitations in my own ideas and thinking by working with them.
The work that I was doing before I joined Google was related to the hashtag: attempting to provide the raw building blocks of a decentralized social web to disrupt Facebook’s inevitable rise as a monopoly power, which I worried would threaten the vibrancy of the startup and indie web ecosystem (a fate that has nearly come to pass). In addition to the hashtag, I worked on several formats and protocols to enable the interoperability of social applications and websites, including OAuth, OpenID, Portable Contacts, Activity Streams, Salmon, PubSubHubBub, WebFinger, XRDS, and more. Since I joined the newly-established social web developer relations team, being with Google gave me a much larger platform to promote the dream of building social functionality into the web itself.
I stayed for three and half years to grow, professionally (as a product designer and leader), and individually (as a dynamic human). The first half of my time was spent as a developer advocate — Google’s take on the technical evangelist. But since I wasn’t an engineer, I had to fight to establish my relevance on that team, so contributed by being an outspoken advocate and liaison for developers outside the company. The external part of my role didn’t last long, however, since I was supporting Google Buzz, Google’s ill-fated first effort at building a social aggregator into Gmail. Once that project was shut down the company rebooted its social efforts leading to the project that would become Google+. With external advocacy on hiatus, I recast my role as an internal developer advocate, running hackathons and design sprints to teach Google engineers how (and why!) to build social apps.
In this work, I realized that there was an opportunity to overhaul Google’s developer documentation and outreach materials, which had been strewn across several Google Code websites, or published haphazardly on Google Sites pages. Thus I started organizing the effort that would lead to the creation of Google Developers — a brand to unify all of Google’s external APIs, API console, and developer documentation.
I recast my role as an internal developer advocate, running hackathons and design sprints to teach Google engineers how (and why!) to build social apps.
I spent about six months with the team designing and leading that effort, working closely with developer relations, the developer documentation writers, and developer marketing in order to launch the new brand, website (developers.google.com), and renamed GTUGs to “Google Developer Groups” at Google I/O 2012. With that work done, I felt like I no longer had much of a purpose or room to grow within the developer relations team and underwent the internal interview process to switch roles to become a UX designer on Google+.
You helped to create Google Developers, redesigned the Google Profile, created designs for the Google+ 1 button and brand badges. If you had to pick one, what project was your favorite, and why?
My favorite project at Google was the redesign of the profile. In terms of the problem, scale, scope, and strategic importance — and the talent of my small, nimble team — it was at once challenging and also satisfying.
Many people probably don’t remember what it was like to manage your presence on Google before Google+ came along, and more likely, for those who used Google+ or were familiar with it, they probably didn’t fully understand the intent of the initiative internally. Put simply, Google+ was Google’s realization that people, thanks largely to Facebook, were going to expect the web to be a more personalized, social environment, and that advertising would move in that direction as well. Google, therefore, needed a better way to capture and store information from and about people, and to map people’s real life relationships, to provide more personal and personalized experiences, to meet peoples’ evolving expectations. The Google+ profile, therefore, could serve as a point of aggregation for all that Google knew about you — a kind of spine off of which other services could be built.
Google, needed a better way to capture and store information from and about people, and to map people’s real life relationships, to provide more personal and personalized experiences, to meet peoples’ evolving expectations.
Prior to the Google+ profile, there was something like 40 or more discrete profiles that might represent a single person across Google’s vast number of products and services. And each of those profiles allowed you to use a different name or profile photo or bio… a feature in an earlier time, but a liability as your Google account became the key to unlock your accounts and personalization on third party websites and apps. Consolidating how you appeared throughout Google’s family of apps and services necessitated giving users more control over what, where, and how information about them appeared on Google — hence the need for the Google+ profile.
Subsequent iterations of the profile involved my first mobile-first design projects, and my instinct was to design a profile experience in which you could infinitely scroll through someone’s life… to first get a gestalt of their interests and activities (with content interwoven that was shared privately with you), with the ability to dig into a category or take action as a secondary step.
I also felt that it was also important to optimize for the majority use case — which would be for users who weren’t active on Google+ or who chose to keep their profile private. For those users, I still wanted to surface a beautiful landing page (inspired by about.me) if they came up in a search on Google, but without necessarily offering too much information. We prototyped this kind of profile, but never launched it:
Importantly, the Google profile needed to work for people, brands, and local businesses (for the integration in Google Maps). Here are a few of the iterations I developed:
The version of the profile that launched offered a large background image with just a round profile photo and name — with a set of tabs for different sources and types of content near the bottom of the page. Once you scrolled a little, if there was content, it would pop to the top of the screen and you’d be immersed in content. We also had to keep in mind that people were using these profiles to find and interact with others, and so always needed to keep an expanding bar of actions like sending a message or initiating a Hangout visible above the fold.
There were many different functions that the profile served, and many stakeholders to consider. Every iteration made different tradeoffs, making it extremely challenging to land on the final design. Ultimately, especially for cross-platform profiles, there’re really only so many ways to design a profile that will serve users with very little to large amounts of content. I’ve watched Facebook contort its profile in all sorts of ways and can see them iterating on the same things challenges we faced — i.e. leaning towards more personal expression or trying to nudge users to adopt some new feature (i.e. Stories, Dating, etc). In fact, at the last F8, Facebook revealed a new design (called FB5) which looked nearly identical one that we launched seven years ago!
I’ve watched Facebook contort its profile in all sorts of ways and can see them iterating on the same things challenges we faced — i.e. leaning towards more personal expression or trying to nudge users to adopt some new feature (i.e. Stories, Dating, etc).
You were super positive about Google+, but it’s officially close down now. What are your thoughts on this and how has you life changed after you left Google?
I joined Google initially because I didn’t want Facebook to go unchallenged. Google’s initial strategy was pro-web and pro-decentralization, but unfortunately those attributes make it hard to mount a product- or design-led challenge. Decentralization typically requires that you design to the lowest common denominator features, drive towards consensus through running code, and ultimately take the long road to success. Given the speed at which Facebook was moving, especially towards mobile, Google execs determined that they couldn’t afford to wait for that kind of strategy to pan out and so pirouetted to a Google-first footing.
I joined Google initially because I didn’t want Facebook to go unchallenged.
For a while, it seemed possible for the social network market to end up as a duopoly — which seemed preferable to a monopoly — but Google stumbled along the way, first by creating solutions that were too complex for average users (i.e. Circles) and by — inexcusably — missing the shift to mobile (Google was simultaneously growing the Android ecosystem). It seemed to me that product direction from the top was chasing Facebook from at best two years prior, and seemed no longer aligned with the principles it had laid out at launch, or was at least was adrift in the emerald sea of the social web, without a port in sight to dock its battered and listing vessel.
I became increasingly frustrated and annoyed. I was irritable to be around. I struggled to reconcile the mismanagement that I saw around me with the importance I felt about our work inside myself. Three and half years into my tenure at Google, I decided that I just couldn’t muster the enthusiasm and resolve I needed to keep pushing. It was time for me to move on and admit defeat (even if Google wouldn’t throw in the towel for another four years).
After I left Google, I struggled but felt like I needed to stay in the game to maintain my professional momentum. People told me to take time off, but I didn’t listen. I didn’t think I needed to listen. Secretly, I worried that I’d lose my edge having seen the competitiveness of the job market. So within a week or two of leaving, I joined a startup that I was excited about, and of which I’d become an ardent supporter and advisor: NeonMob.
Three and half years into my tenure at Google, I decided that I just couldn’t muster the enthusiasm and resolve I needed to keep pushing. It was time for me to move on and admit defeat (even if Google wouldn’t throw in the towel for another four years).
I may have discovered NeonMob through Rogie King, a prolific and overwhelmingly talented visual designer who had cofounded the company with Mike Duca. Having grown up a comic book and sports card collector, something about bringing artificial scarcity to the infinitely abundant digital realm seemed like a fascinating problem to tackle… And having spent so many years working on social software, I was looking for a break and leapt at the chance to work on a platform to support digital artists.
My tenure was relatively short lived largely owing to a mismatch of my skills and and the needs of the fledgling startup. Specifically, I designed a number of features that I thought would improve the core mechanics of the platform (related to messaging and creating digital assets, but the cofounders needed help with growth — not my forté. So, after a few months I left the company to return to my advisory role.
It seemed like I was going to be forced to take time off after Google, whether I wanted to voluntarily or not. I found myself without a clear path forward — and as the cliché requires — had all the time in the world for what was to come next: Burning Man! But I’ll leave that story for a different time and place. 😛
You joined Uber as the first Developer Experience Lead. Tell me about the times you spent there.
After I’d blown up my life (professionally and personally), I came back in touch with an adversary from my pre-Google social web days and we recorded a podcast on non-monogamy, as one does in Silicon Valley. He let slip that he’d be starting at Uber as head of the developer platform and — my interest piqued — told me that we had an opportunity to build Facebook Connect, but for cities. I left, unable to get the idea out of my head.
I joined Uber as Developer Experience Lead, a new role that was kind of like a UX designer-slash-advocate for developer products (API consoles, documentation, etc). I salivated at the idea of opening up Uber’s platform to developers… even then, Uber had a pretty shady reputation and I thought that maybe the developer platform might be a way to turn the tide of public perception for the better. I was wrong, but it was worth a shot. I’d never joined a soon-to-be unicorn and wanted to experience what it was like on the inside.
Although Uber’s DNA came from all over the Valley (Google, Amazon, Facebook, Airbnb, Apple, Microsoft, and others), its culture was distinctively competitive and — the best word for it is — fierce. It didn’t necessarily bother me, even if it contrasted with Google’s more intellectually academic culture… but it did make my role more challenging as my duties required working with and advocating on behalf of the external community to promote integrating Uber rides and API features into other products, apps, and services.
I think of my time at Uber as like being on a pirate ship, where you’re never quite sure who’s going to shank you. You learn (metaphorically) to sleep with one eye open, drink often and enthusiastically, and do the best you can given the pressures. You’re also working with some of the smartest, most talented, motivated, and focused people you’ll find — and the intensity envelops you so you just keep rushing forward with an air of inevitability. Google+ was probably one of the more competitive and intense teams to be on at Google while I was there but being at Uber required operating at a whole different level. It was demanding, and moments were for sure exhilarating while others were devastatingly soul-crushing.
I think of my time at Uber as like being on a pirate ship, where you’re never quite sure who’s going to shank you.
What is your favorite project that you launched while being at Uber?
I can’t take much credit for features that launched — though I worked closely with the teams that wanted to expose API surfaces to third party developers and partners. Right before I started, Uber participated as a launch partner with Facebook Messenger — enabling riders to request a ride directly from within a conversation. This was mind-blowing to me — because it expanded on a trend — conversational commerce — that I’d been following since 2015. This integration is also what lead me to write a piece that declared that 2016 would be the year of conversational commerce — which accurately predicted the tech industry’s dalliance with bots and automated conversations.
I’m proud of the work that the developer platform team produced documenting our API, providing sample code, libraries, testing tools, a full-featured API console, and more. We started out using a documentation platform called Readme but ultimately concluded that our needs were sufficiently unique and that we needed to move quickly, and so built our own developer documentation system. Having gone through that process at Google, I was concerned — and felt that it would distract from our core mission… but I was proven wrong, which is a testament to the talent on our team. We built our own documentation CMS with an integrated API console and it was better than anything else out there.
What was the next step for you once you resigned from Uber?
After a year on the platform team, plenty of controversy, personnel changes, and countless re-orgs, I had to confront the reality that the mission that I’d been sold on to connect people to their urban environment through technology wasn’t going to pan out. My day-to-day responsibilities revolved around driving more integrations of Uber into third party apps to drive rider growth. This made plenty of business sense but just wasn’t where my heart was. I tried to spin up a role dedicated to creating an Uber assistant, but given internal politics, timing, and circumstances, was unable to make that happen, so I left a year to the day and took those ideas and co-founded Molly, a conversational AI company, and became head of product.
What are you currently working on?
In 2019 I left San Francisco to become nomadic and explore the world. I didn’t have much of a plan except I had a couple speaking gigs scheduled in Lisbon and Bend, OR. I just knew that I needed a personal reset after I left my startup, and was starting to feel disillusioned with the Bay Area scene. Fortuitously, I ended up being invited to speak at several more events around the world which set my itinerary for the rest of the year (I spoke primarily about social media, the hashtag, product design, and startup culture and mental fitness).
In 2019 I left San Francisco to become nomadic and explore the world.
This year I decided to travel less and resettle, at least temporarily, in the East Bay, to write a book developing the ideas of the talks I gave last year. My sense is that people have embraced social media and integrated it deeply into their lives without fully appreciating or understanding the road we took to get here. And since I was largely on the outside working towards a specific set of goals (one that lead to the hashtag), and then went inside to work on Google’s entry into the space, I can provide a unique perspective that can hopefully inform what changes are needed as we develop more social software that is enhanced with artificial intelligence.
What do you like to do when you’re not working?
Some of my friends have taken to calling me “the bougie nomad”, because I enjoy traveling and exploring the world while eating and drinking delicious and well-made food and beverages. But I also love learning about the world and understanding why things work the way they do, and opening my aperture to examine things from myriad points of view. Lately, for example, I’ve been thinking about how monogamy and capitalism relate at a very deep level, and considering what our economics might look like if non-monogamy were the dominant relationship configuration.
Lately, for example, I’ve been thinking about how monogamy and capitalism relate at a very deep level.
I love listening to music, podcasts, to the news — I’m listen to several audiobooks at any given time. I enjoy cooking, spending time with my chosen family, and working out.
What’s an interesting or fun fact about yourself we wouldn’t find on your social media?
This is tough one — I’m pretty out there on social media, though there are some aspects of my life that I don’t get to share as often, or that I haven’t found the proper context in which to explore them. One thing that a lot of people probably don’t know is that I spent several months considering building an HQ Trivia-style video speed-dating app after I left Molly but ultimately decided it wasn’t a business I really wanted to get into (I was also warned by several people in the business that there were only two likely outcomes: get swallowed up by Match Group, which is partially owned by the Russian mob, or die trying to stay independent — neither seemed desirable).
Bonus Question: What’s your favorite way to eat an avocado?
I eat at least 1/2 an avocado daily with breakfast — sliced with a dusting of Maldon salt, straight out of the skin.
Also worth mentioning: when I was at Burning Man, my contribution to my camp cooking duties was slicing 300 avocados for an epic amount of guacamole. Everyone that’s seen me slice an avocado agrees: my slices are tight. 😂
Also, my favorite avocado toast that I ever had was in Sydney, Australia: