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100 Pros 1 Fund

7 min

Part 1 of The Chad & Cheese AI Sessions features Tim Sackett—author, investor, and long-standing provocateur in the HR tech space—returning with a venture fund, a new book, and no shortage of unfiltered insights.

This episode explores what happens when industry experience, entrepreneurial ambition, and sharp commentary collide. Sackett brings both humor and hard-earned perspective to topics ranging from publishing to public speaking, and of course, the ever-evolving world of talent acquisition.

Key topics include:

- Why publishing a single book suddenly elevates one’s credibility—despite a blogging history that spans over a million words

- What happened when SHRM attempted to edit his work (spoiler: it didn’t end in compromise)

- Why his latest book includes intentionally provocative chapters such as  “The White Guy’s Guide to Diversity Recruiting” and “Hiring Pretty People” designed to challenge conventional thinking rather than reinforce it

From AI strategy to the politics of keynotes, Tim Sackett delivers a candid, and at times confrontational, take on the future of HR. Consider this your fair warning—he doesn’t hold back.

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