Departing Thinkful & A New Call to Code

When we founded Thinkful in 2012 it was labeled “alternative” education second to degrees and 4-year college. Eight years later 62% of Americans prefer non-degree skills training over degrees. In 2019 we sold to Chegg for $100m, lowered prices for students, integrated, hit plan, and hired for the experience necessary to scale inside a public company. Chegg also nearly tripled in value. Chegg and Thinkful are shaping the future of education.

But America’s recovery from COVID will accelerate wealth and opportunity injustices: In 2021 I fear a lucky few will continue getting richer, while debt and uncertainty will suffocate most Americans’ ambition. This delays and destroys millions of families and careers. 44% of American workers earn $10 / hour. The average American is $90k in debt. We already live four fewer years than our peers.

Those of us trained to rethink large systems must see this as a “Call to Code”. Lucky risk-takers (and yes, my success is mostly luck) must figure out how to better distribute luck. Education will be one solution. Others surely include answering how gig and frontline work can engender economic mobility, and what replaces the social safety net. To play on a phrase, opportunity is already here — it’s just not very evenly distributed. Let’s fix that.

Thinkful now has the best leadership, brand, team, educators, and in Chegg, steward, that it’s ever had. So, it’s time for me to move on. My transition out offers me the privilege of asking big questions, again. I’ll be contributing some answers soon enough. But first, I’ll spend a bit of time with my husband, our family, our friends, and our native NYC.



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Darrell Silver

Launching companies with undiscovered founders for 503 Corp. Co-founded+CEO’d+sold Thinkful (acquired by Chegg) & Perpetually (acquired by Dell).