Show Notes
Will Ruben spent more than a decade at the companies that taught the internet what attention looks like. He led ranking and recommendations across Instagram during the era when Reels stopped being a feature and started being the entire product. He worked on Coinbase's Web3 Wallet. He scaled consumer products for billions of people. And then he walked away from all of it to solve something almost embarrassingly small in scope: the back and forth of scheduling a meeting.
That choice is the whole story. Will is not building Workmate because scheduling is glamorous. He is building it because scheduling is the gateway drug to giving every knowledge worker the kind of strategic support that used to be reserved for executives with assistants and corner offices. The premise is democratization, the wedge is the calendar, and the long arc is a world where you collaborate with a mix of humans and AI teammates that feel indistinguishable from coworkers.
In conversation with Ryan, Will lays out a thesis that is unusual in this AI moment. While most founders are racing to make their agents louder, faster, and more obviously artificial, Will is doing the opposite. Workmate is engineered to disappear. It has an email address at your domain. It writes the same way every time. It is white-labeled, customizable, and in many cases, the people interacting with it do not know they are talking to AI. Will calls this a flex. The flex is appearing more important than you are.
The conversation winds through the ethics of disclosure, the speed of building when the foundation models change every two months, the difference between sculpting and painting, and a tangent on Instagram Reels that will make you reconsider why your wife sees men cooking with no shirts on. It also lands somewhere unexpected: a quiet, almost paternal argument that the founders who win in this era are the ones who go to bed on time.
1. The Trust Curve in AI Disclosure
Will frames the disclosure question not as a binary but as a function of industry, demographic, and medium.
Internal team communication: full transparency is the default because users know they are working with the productExternal client communication: depends on industry norms (some sectors expect executive assistants, where AI fits seamlessly into existing expectations)The Workmate position: provide both options and let the customer choose the level of transparencyThe bet: in two years the question will dissolve entirely because AI teammates will be normalized the way remote work was normalized between 2015 and 2025
2. The Three Waves of Instagram (and What They Taught Will About AI Products)
Will identifies three distinct product eras at Instagram, each of which informs how he is building Workmate.
Wave one: filters on the feed (self-expression)Wave two: stories (ephemeral connection)Wave three: constant content recommendations and Reels (algorithmic discovery)The takeaway for AI: the third wave succeeded because it gave users more control over what they saw, not less. Workmate applies the same principle to scheduling preferences.
3. The Sculpting versus Painting Distinction
Will and Ryan agree that the founder's job is shifting from execution to taste.
Painting: the founder hand-crafts the outputSculpting: the founder shapes what AI produces by setting parameters, reviewing direction, and arbitrating qualityThe implication: management skills, not technical execution, become the bottleneckThe catch: agents are not fully autonomous yet, so founders still cannot fully step away
https://www.linkedin.com/in/wruben
https://www.linkedin.com/in/estesryan/