We sold OkCupid to Match in January of 2011. In September of

In the annals of builders and stewards, a clear milestone is set down like a boundary stone: “We sold OkCupid to Match in January 2011. In September 2012, I became CEO of all of Match, which is the operating segment of IAC that contains all of the dating properties.” Hear how the sentence moves from seed to harvest, from one fire tended to many lamps overseen. The first clause is the rite of passage—an entrepreneur laying a crafted vessel into a greater fleet. The second is a mantle—responsibility widening from a single hull to the whole armada. In these two dates the shape of a vocation changes: maker becomes guardian, founder becomes shepherd.

To say “we sold OkCupid” is not merely to cash out; it is to graft a living branch onto a sturdier trunk. Within January 2011 lies a founder’s humility: that a product born in a small forge may keep its flame longer beneath a larger roof. And to add, “I became CEO of all of Match” in September 2012 is to name the trust that follows proven craft: the artisanship of one house invited to tune the whole village. What began as solving for two people on a screen ripens into stewarding an ecosystem—policies, safety, product, and culture for millions seeking one another in the dusk.

This is the old arc of responsibility. First, you learn to keep a single promise—reliable sign-up flows, clean matches, honest metrics. Then you are asked to keep many promises at once—brand integrity across the dating properties, alignment of teams, the quiet justice of moderation at scale. The phrase “operating segment of IAC” is dry on the tongue, but in it lives a real charge: to make the marketplace not only grow, but grow clean; to ensure that the wind filling the sails is fair wind, not storm.

Consider a parallel from our own era. When Pixar joined Disney, Ed Catmull and John Lasseter were asked to carry not just one studio’s magic but to rekindle a kingdom’s broader craft—translating the discipline that made a few works excellent into habits that could elevate many. In like spirit, a leader crossing from OkCupid to Match is tasked with raising standards beyond a single brand: safety systems that scale, analytics that respect humans as more than metrics, and a culture where many teams sing from the same key without losing their harmonies.

Yet the heart of the quote is not corporate architecture but human purpose. OkCupid, Match, and the constellation of dating properties exist because solitude knocks at doors, because courage needs a bridge. The journey from founder to portfolio CEO is, at its best, the journey from crafting one bridge well to tending a whole river—lighting more crossings, patrolling for trolls, keeping planks sound in every weather. The work becomes less about personal brilliance and more about institutional virtue: designing systems that make it easier to do right than to do harm.

What lesson shall the apprentices keep? First, build something so honest and useful that a larger house invites it in without smothering its soul. Second, when your circle widens—when titles lengthen and halls echo—remember the single user at midnight who still needs a trustworthy path. Third, measure your success not by acquisition alone, nor by rank alone, but by the quality of the commons after you arrive: safer rooms, clearer rules, kinder defaults.

Let your actions be plain and durable. Hone a craft until it is worthy of partnership; when partnership comes, translate principles, not just features. If you lead a single product, behave as if you already steward a portfolio—document, mentor, design for scale. If you inherit a portfolio, walk its streets at ground level—use the apps, read the tickets, listen to the shyer voices. Guard the mission shorn of ornament: to help strangers meet with dignity. In this, the dates—January 2011, September 2012—become more than milestones; they become sacraments of stewardship, marking the day a maker learned to keep many lamps burning through the night.