Founding Year Eight

Darrell Silver
2 min readSep 4, 2019

Today we’re founding the next era in Thinkful history: an era where our mission to build the world’s next workforce truly begins. For seven years we’ve known, deep down in our soul, that all adults should learn the way we teach. We’ve proven it works with our audited results. Now we get the chance to deliver not just for the thousands who choose us today, but for the millions who’ll choose us next.

“Bootcamps” were started as an alternative to expensive and slow higher ed programs, but prices have ticked up every single year since 2012, now crossing $20k. High cost is bad for students (even when you pay later). High cost limits access, and is a slow ooze toward the status quo. This year Dan & I came to realize that to build the world’s next workforce prices need to go way, way down. And this must be done without compromise to quality, support, and extraordinary student outcomes.

That’s why we’re ecstatic to join Chegg. They’re the adults in the room bootcamps need. Chegg is a massive company in education, and today we’ve announced it will acquire Thinkful for $100m. Together we share a deep belief that the future of adult education must be accountable for student outcomes, low-risk, high impact, and incredibly affordable. Our values are deeply aligned: Student-first, intellectually honest, transparent, and approaching everything we do with an unreasonable passion. Chegg chose Thinkful as a platform to reach adult learners, perfectly complementing its existing learner base of millions of college students. And we’re hiring.

“Learning is not a four-year thing, it’s a forever thing” in Chegg’s NYC office

We’ve been working on this for months — plenty of time to consider and plan, course correct and discuss. Above all I’ve realized that today we become life partners. We’re creating something so few get to experience, and that this experience will bind everyone at Thinkful in job, career, friendship, mission, and for the rest of our lives no matter what. I think that’s also called family. To the Thinkful community of students, alumni, educators, team: Welcome to the Chegg family. Congratulations on getting us to today and congratulations on making tomorrow possible.

This morning we’re very, very proud, and we’ll enjoy it. This afternoon we’re back to work.

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Darrell Silver

Co-founded+CEO'd+sold Thinkful (acquired by Chegg) & Perpetually (Dell). Now researching AI,, board The Young Center, furniture maker.