How a Free Video Closed Reddit w/ Jordan Winston (Ep #53)...

Q: How long is this episode of Curiosity Class?

This episode is 34 minutes long.

Q: When was this Curiosity Class episode published?

This episode was published on June 12, 2026.

Q: Can I download this Curiosity Class episode?

Yes, you can download this episode by clicking the download button on the episode player, or subscribe to the podcast in your preferred podcast app for automatic downloads.

What this episode covers

A 26-year-old cold DM'd Reddit saying "I'll shoot over the video when it's done" - before he'd made it. He closed a Fortune 500 client with a video that didn't exist yet.Jordan Winston is the founder of Not Your Dad's Media, a street interview ad agency that's landed brands like Reddit, sports betting platforms, and CPG companies - all built from scratch in six months with no funding, no co-founder, and a LinkedIn DM strategy most people would be too embarrassed to try.What you'll take away:The exact cold outreach method Jordan used to close Reddit (and why telling someone "it's almost done" before you've started is genius, not dishonest)Why Jordan's biggest lesson after six months of building is "do less" - and the three things that actually move the needleThe case for founder-business fit over status: why Jordan chose to build an agency instead of a product, even though NYC startup culture says that's the wrong callLinks mentioned:Not Your Dad's Media: notyourdadsmedia.comJordan on LinkedIn: Jordan Winston (bio says "street interviews")Jordan on Instagram: @jordanwinston_Follow Curiosity Class:YouTubeSpotifyApple PodcastsLinkedInInterested in sponsoring? [email protected]

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