Episode 53

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

June 12, 2026

00:34:10

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? curiosityclasspod@gmail.com

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Episode Notes

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 call Links mentioned: Not Your Dad's Media: notyourdadsmedia.comJordan on LinkedIn: Jordan Winston (bio says "street interviews")Jordan on Instagram: @jordanwinston_ Follow Curiosity Class: YouTube Spotify Apple Podcasts LinkedIn Interested in sponsoring? curiosityclasspod@gmail.com

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