Interview · moment 18 of 24
Hiring Is Just Guessing, and Contextual Creative Per Platform
from Two Greatest Minds of The Century (Gary Vaynerchuk) | The Tim Dillon Show #324 · #324
4 min
Guest
Gary admits hiring is largely intuition and guesswork, then pivots into advising Tim to post more on LinkedIn and explains 'contextual creative' — tailoring content differently for each platform and city, just like a comedian adjusts jokes by room.
- Tim argues that hiring is fundamentally guessing, though experience makes you better at it.
- He describes mishiring people constantly and laughing at how bad recent hires have turned out.
- The key to good employees at his company: avoiding cynicism and not being afraid, since the doors are open and communication is unlimited.
- Tim suggests doing more content on LinkedIn, since his thoughtful comedy would work well there clipped and properly framed.
- Every platform requires different creative strategy—TikTok, YouTube Shorts, and Twitter each demand their own approach.
- Comedy changes city to city and country to country; Tim tailors his sets with location-specific jokes like Josh Allen references in Buffalo or footy jokes in Australia.
- Understanding contextual creative—tailoring content to each platform where you're actually distributing it—is the single most important thing that can advance a career or business.
YouTubeTikTokLinkedInTwitterCooper's beerJosh Allen