The Changelog: Software Development, Open Source

From WeWork to upskilling at Wilco (Interview)

Jul 24, 2022

On Freund, former VP of Engineering at WeWork and now co-founder & CEO of Wilco, discusses his transition from scaling WeWork to revolutionizing developer education with Wilco. He compares the dramatic portrayal of WeWork in the series 'WeCrashed' to reality, highlighting unique challenges in tech scalability. With Wilco's gamified simulations, he emphasizes the importance of practical skill acquisition in tech, enabling developers to learn in real-life scenarios. The conversation is packed with insights into building immersive experiences and the future of AI in education.

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ANECDOTE

WeWork's Tech Department

On Freund refutes the "WeCrashed" portrayal of WeWork's tech department as fabricated.
He clarifies that a tech department existed long before the show's timeline, growing organically to 1,000 developers.

ANECDOTE

WeWork.com Evolution

WeWork.com underwent multiple rewrites, driven by branding changes and maintainability goals.
These iterations involved backend improvements and adopting a static site with an API approach.

INSIGHT

Billing Challenges

On Freund highlights the complexities of international billing, a significant tech hurdle at WeWork.
Existing billing systems were too slow, leading WeWork to create its own system.

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This week we’re joined by On Freund, former VP of Engineering at WeWork and now co-founder & CEO of Wilco. WeWork you may have heard of, but Wilco maybe not (yet).

We get into the details behind the tech and scaling of WeWork, comparisons of the fictional series on Apple TV+ called WeCrashed and how much of that is true. Then we move on to Wilco which is what has On’s full attention right now. Wilco has the potential to be the next big thing for developers to acquire new skills. Wilco aims to be the ultimate simulator to gain new skills on a real-life tech stack. If you want to skip ahead, you can request access at trywilco.com/changelog — they are moving our listeners to the top of the waiting list.

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Featuring:

On Freund – Website, GitHub, LinkedIn, X
Adam Stacoviak – Website, GitHub, LinkedIn, Mastodon, X
Jerod Santo – Website, GitHub, LinkedIn, Mastodon, X

Show Notes:

Something missing or broken? PRs welcome!