Table of Contents

01 Crucial Context: The Digital Art Market is Born
02 The Challenge: Reimainging a Digital Art Marketplace in 9 Months
03 The Discovery: Kicking Off By Taking Stock
04 The Solution: The Radical Separation of Art from the Market
05 The Outcome: A Ground-Up Redesign & Economic Innovation

Crucial Context

The Digital Art Market is Born

When blockchain technology first converged with digital art in the mid 2010s (NFTs), a niche group of hackers, anarchists, and artists saw an opportunity to trigger a global creative renaissance unlike the world had ever seen. Dada was a first mover, years before NFT as an acronym or speculative cultural artifact became widely known. What about NFTs was so compelling that Dada and other trailblazers like Rare Pepes and CryptoPunks leaned in?

Simply put: before blockchain, digital art had no value because it could be endlessly reproduced. Copy, paste, worthless. But now, this new technology made it possible to turn digital art into unique assets that could be transacted – bringing scarcity, authentication, and ownership online – and allowing them to capture value just like physical art. Boom, up spawns the digital art market.

Before this market moved and shook, Dada was a social media platform where visual artists like painters, illustrators, and back-of-the-napkin doodlers alike came together the world over to co-create artworks in a unique way, similar to “One Word Story,” the party game where participants take turns saying one word at a time to create a spontaneous narrative. We called these visual conversations. And they're pretty magical:

Thousands of these conversations made up of over 120,000 unique illustrations in total had been created on Dada by a passionate, engaged community with our tools — the largest collection of rare digital art in the world. And so when its founders discovered blockchain, Dada was in a position to convert those artworks into NFTs – along with its market-making properties – virtually overnight.

Making history, Dada launched the famed Creeps & Weirdos collection on Halloween 2017, a standalone marketplace to experiment with selling a curated selection of individual works from our visual conversations as NFTs. This historic moment minted us as one of the first NFT platforms ever and the only one – with our mission to put artists first – to bake in a programmatic royalty structure that auto-paid a percentage of future sales to the artist when a work switched collector’s digital hands in perpetuity.

The Challenge

Reimagining a Digital Art Marketplace in 9 Months

Bad Incentives = Bad Behavior

“The NFT space is chock-full of financial and technological innovation, but what truly sets it apart is the unique opportunity to ‘do it right’. By infusing it with diversity, value distribution, and sheer artistic virtuosity, [Dada] has reimagined the collectible movement and done it right.” — Metakovan, Metapurse Founder

As other entrepreneurs and investors caught wind of digital art’s innovation, an arms race began. Who was going to capture the most value in a hot new space? But in Dada’s view, we found the emerging digital art ecosystem around us to have sight, sure, but no vision: to thoughtlessly inherit the free-market norms of the traditional art world would drive the same speculative behavior that treats art and artists like financial assets. 

Here was an opportunity to completely reimagine the paradigm. In art markets and so many systems of our world that organize human activity, the incentive structures are bad. And so we knew in our hearts that our point was to align the economic dynamics that would govern our marketplace with the greater good of art and artists. But a dream is but a dream without a plan.

My Role & Reality

I was hired as Head of Product to:

1. Recruit and lead a design / development team to overhaul the artist’s experience across web and mobile
2. Work with our CTO to convert the archive of 120,000 digital artworks into NFTs to make them functionally transactable 
3. Explore, define, and productize a viable, “enlightened” economic model alongside the founders
4. Create a platform with a strong foundation for marketplace innovation and a diversifying user base

And boy did we have our work cut out for us.

Limited Runway & Time

We raised a small seed round ($350k) from ConsenSys, the premier Ethereum investment fund of its time. It bought us under a year to research, design, develop, launch, and raise more capital. 

Bad Design Is Bad For Business

Dada's software was in rough shape, whacked together. It suffered from devastatingly low conversion and retention — with 150,000 sign ups, only a few thousand returned, and of those, only a few hundred became regular users. 80%+ of support emails were folks frustrated with usability or performance.

Market Nascency & NFT Esoterica

The technical and cultural infrastructure around the digital art ecosystem was precarious and barren — a true wild west! Our users, too, struggled to understand the abstract value of blockchain technology and were concerned how selling work may impact Dada as a creative community.

Growing Pains

With no clear product vision, strategy, or org workflow, I rallied the founders to introduce a "leveled-up" mental model that opened and organized channels of comms cross-functionally.

Remote Work

As a fully remote and multi-cultural company, I had to facilitate the research, design, and development processes across four timezones, 10+ stakeholders, and three language barriers.

The Discovery

Kicking Off by Taking Stock

"The experience of co-creating visual conversations on Dada tapped into something primordial around humans as social creatures: the language of visual storytelling is a timeless expression bonding self and other."   

Because data wasn’t easily gatherable to help drive design decisions, I spearheaded a series of research efforts to understand and frame the problem set, and develop requirements for a user-centric, elevated redesign.

Heuristic Evaluation

I took inventory of every page, element, and interaction — an “exploded view” was the level of atomized granularity I needed to understand Dada. I suspected our low retention could be largely attributed to both confusing flows and poor onboarding / education around how to make progress and access functionality through our gamified system.

Stakeholder Interviews

Our founders (power users themselves) had close friendships with some of our most active artists from around the world. Their insights from years of osmosis, I teased out with a series of interviews that allowed me to truly understand the psychographic of a Dada artist. 

Contextual Inquiry / Usability testing

In a series of 20 screen shares, I requested our most engaged artists to use the product and articulate their thinking as they moved through various user journeys. I also became a power user myself (though I surely have no future as an illustrator).

User Surveys

I was curious to see how attitudinal data in surveys would differ from behavioral data I witnessed in usability testing. The data revealed how users felt about Dada aligned with how they used it. I interpreted this harmony between intention and action in the experience of co-creating visual conversations as tapping into something primordial around humans as social creatures: the language of visual storytelling is a timeless expression bonding self and other.   

Legacy Data

Very little to leverage here: high-level Google Analytics and a cumbersome archive of support emails with complaints and requests. I synthesized it all and gleaned what I could. 

Panels & Conferences

News traveled fast that we raised money from ConsenSys — we began receiving invitations to attend and speak at major events, like Ethereal Summit and Christie's Art + Tech Summit. Being new to the space, I had to quickly get up to speed — beyond my own research, attending these events were not only valuable opportunities for us to demonstrate thought leadership, but also to speak with other builders and learn about the competitive landscape at large.

Every Picture Problem Needs a Frame

By now, we de-risked our assumptions and had a solid foundation from which to define requirements for a redesign. However, our perception of the risk of integrating a marketplace dramatically increased.

Though we strongly believed the innovation in blockchain technology could enable our mission to align buying art on Dada with the greater good of art and artists, our founders felt strongly that the risk of introducing commerce prematurely could undermine the culture and social norms we had cultivated among users.

And so after serious and at times tense deliberation, the founders decided to backlog the design and development of a marketplace, and instead focus on defining its prerequisite mechanics. We needed to go deeper into the problem and consider the governing dynamics that drive behavior and activity in an economic system. And so we asked ourselves:

How might we innovate on economic ideology in a way that not only keeps the artist's experience intact, but amplifies it?

The Solution

The "Invisible" Economy: A Radical Separation of Art from the Market

A Universal Basic Income for Digital Artists

Through comprehensive analysis of progressive economic theories from minds like Noam Chomsky, John Maynard Keynes, Friedrich Hayek, Michael Albert and Jimmy Wales (to name a few), we developed a viable economic vision for Dada's marketplace modeled on participatory economics called The Invisible Economy.

We determined that in order to preserve artist's intrinsic motivations and the collective social norms that made Dada such a purely creative place, the economy must be "invisible" — we would necessarily decouple the experience of making art sales from that of making art itself, obscuring the marketplace and its requisite incentive structure. And in the process, Dada would provide every user with a Universal Basic Income (UBI).

Good Incentives = Good Behavior

With an "invisible" economy that automatically meets their material needs, artists would live free from the competitive or survival pressure to sell, market, or produce work, and remain incentivized by higher values that have governed the entire community to-date. In the virtuous circle of our incentive framework, the economy would reinforce itself continuously.

It Takes A Village

To create an equitable economic system, we intended to "value" and measure the different ways folks contribute to the community, beyond the revenue driven through sales of artwork. This would enable us to quantify and correlate all user contributions with UBI redistribution.

The Redesign: Dada 2.0

Dada is fundamentally an open canvas characterized by user-generated content designed around one core experience: having visual conversations. Whether starting a new one or replying to an existing one, Dada users log in to actively create, browse, engage with the community, and often some combination of all three. As such, our design philosophy was to find the nexus between access, clarity, and playfulness — good design here just "gets out of the way."

A few key questions shaped our design process to rebuild Dada's information architecture, flesh out wireframes, UI elements, and user flows, and land on a visual design direction we felt honored Dada's history, and honored it well.

• How might we surface and animate the underlying "events" that make Dada quite literally a living, breathing work of art?
• How might we restructure search, navigation, and intention targeting to be more intuitive in the least amount of clicks?
• How might we retain the philosophy of Dadaism while leveraging more sophisticated design techniques?

Main Navigation

In the old Dada, search, discovery, profile and all navigation flows were built around inconsistent design patterns, disjointed and clumsy. An example: finding content by artist, tag, or browsing lived on different pages accessed by different UI elements. Who knows!

Now, all navigation is organized sensibly on the left margin with a pop-out panel where relevant. This acts as a mission control to manipulate all content in a fixed, vertically-scrolling main feed. We also amplified discovery with filters covering key search cases.

Three-Dimensional Branching

Before the redesign, users could only see the "top layer" of a visual conversation — a two-dimensional experience. Meaning: user A makes drawing 1, user B responds to 1 with drawing 2, and so on. If a conversation has four total drawings, and drawing 2 gets two new responses, it creates a "branch".

However, the old interface only showed the most recent response, burying every prior response. And so we designed a break-out solution to dynamically surface 100% of drawings. In a toggle drawer beneath every visual conversation, users access a real-time, three-dimensional branch model of its constituent drawings at a high and granular level.

Now they can see the total responses per drawing, how drawings branch off from one another, and by clicking the desired thumbnail, that particular drawing at its branch location will load into the visual conversation above. And off they go 🎨.

"Enlivening" Dada

Dada is a living, breathing work of art — a vibrant community of folks are simultaneously starting or contributing to visual conversations the world over. Yet its still and static interface obscured the fact that a constellation of connection and creativity is happening in real-time. And so we brought it all to life with a few key concepts.

Dada Live is a modal with three real-time features: a ticker for how many artists are currently logged in, a carousel updating every time another user posts a drawing, and access to Dada Radio: a virtual room for audio conversation between all logged in users.

Historically, we learned some of our users who became friends (as a consequence of visual conversations) would call or video chat together while drawing. Comments sections, too, were usually "bursting" with a conversational tenor. And so we productized these behaviors into one cohesive experience, collapsing walls between silos.

We also recreated the real-time typing indicator we see in messaging apps – the three dots that appear on your screen to show when someone on the other end of your text is typing – so users could see new drawings being worked on in the context of a visual conversation in real-time.

For users who had not toggled open a visual conversation drawer and were just scrolling the main feed, we wanted to signal the same sentiment. And so we added an animated paint brush icon to convey an artist(s) is drawing in this conversation right now.

Gamification & Product Education

On Dada, artists don't "level up" with compulsion-driven gamification mechanics that incentivize acquisitiveness and competitiveness. They merely earn colored dots as they make progress through a simple point system representing their unique contributions.

Artists "unlock" the ability to respond to visual conversations by earning dots of equal or greater amount than the conversation was set at by its creator. If I had earned three dots and a visual conversation was set at two, I could respond. At four, I'd have to earn one more dot, and for now can only appreciate this particular conversation as an evangelist. A 200 point baseline helps us filter out trolls who may create an account and deface visual conversations that artists put a great deal of effort into it.

To guide users through this system, we used:

• Contextual tooltips and hover events on any element related to dots / reply eligibility
• For the first three log-ins, a pinned banner with description
• A dedicated FAQ page

Content Curation

When a user logs in and no search action is yet taken, they're immediately thrust into a feed of visual conversations. And so we designed an algorithm that displays conversations by:

• 50% — the most engaged (by # of replies, likes, comments — which also tended to be the most "beautiful" making the interface an aesthetically-pleasing place to be)
• 35% — dot level compatibility
• 15% — exposure to the broader community so cross-pollination was happening between veteran and new users / visual conversations alike.

Dada On The Go

While the primary behavior on Dada is drawing, users also browse, comment, like, and share — just like other social media platforms. And while mobile interfaces are too small to be a productive drawing canvas, we built a simple responsive mobile experience and added a fun shuffle feature as a down-scoped version of three-dimensional branching on web.

Dadaism Is Not Dead

Initially as a design team we had an averse reaction to the unpolished styling around icons and other UI elements. But as we got to know our users better and the philosophy that drove both Dada as a movement and Dada as a company, we felt its values were extremely important to maintain in the details.

The Outcome

A Redesign & Economic Innovation, Even Without A Launch

We had a month of cash in the bank when a values-aligned VC who had verbally committed to capitalizing our next round was overruled by her superiors. We were six weeks from shipping and launching the redesign and entering a new design sprint to productize our new economic model in a v1.0 marketplace. 

In the wake of that news, the founders made the difficult decision to pause and not prematurely take on outside capital from the “wrong” investors merely to infuse the business with cash short-term. With too much influence, they felt a new investor could undermine the intention of reimagining market dynamics and force the hand towards any proven, high-return business model.

And so at the end of the month, the outsourced engineering team’s contract went unrenewed, and my design team and I were laid off. (In good spirits, we all volunteered to work a few extra weeks to hand-off and support the transition).

A Flyover of Outcomes

Disheartening as it was, a redesigned product 95% developed and a comprehensively researched and defined economic model shaped – with tremendous clarity – the vision, product strategy, and business goals that were nebulous and nascent when I first joined, enabling Dada’s founders to fly forward with a practical aim at its target destination were they to re-capitalize.

Our usability tests with 10 users were met with rave reviews. Let’s fly over these outcomes.

A very bittersweet ending to nine months of tremendous work. Since then, Dada’s founders have not raised outside venture capital (as I would have rejoined) and instead converted the organization into something of an artist collective. By resourcing within the community, they can continue to explore and realize their post-capitalist, socio-economic system that we came to know as The Invisible Economy, free from bad incentive structures and the norms that degrade the role of art and artists in our societies.

Post-Script

Humans assign value based on our values — it’s that simple. The problem is, not all values are weighted equally. When we grouped together and formed modern societies, the best of our nature was oppressed by the incentive structures that drove production of profitable goods and services. Greed, envy, self-interest, acquisitiveness, and a strong desire for power or wealth at the expense of others or the planet became psycho-behaviorally rewarded when it resulted in the development of more goods and services, or more power and wealth for the already powerful and wealthy. Wisdom, generosity, open-heartedness, vulnerability, compassion, acts of love — we have, rather devastatingly, not managed to organize our societies around these enlightened values.  

Now more than ever are these bad incentive structures eroding the human enterprise and the planet in which we inhabit. I was proud to be a part of Dada's effort, despite the outcome, to talk the talk and walk the walk.

Proud, too, was I to be a part of an LGBTQ+, immigrant, female-founded startup, representing too small a percentage of venture capital dollars deployed.