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Marketing Playbook Episode 5

What scrappy, founder-led marketing really looks like—campaigns, pivots, and playbook-level insights

Issue #224

August 4th, 2025

Quick Hits:

This week, we caught up with Dewar Gaines, the CEO/CMO of Gaines Family Farmstead. Amongst other things, we covered…

  • The low-budget 4th of July campaign that absolutely crushed.

  • Why one influencer campaign failed in conversions but revealed a goldmine in retention.

  • How live selling is becoming their secret weapon for engagement and sales.

  • The underused tactic that drove foot traffic to 200+ retail stores.

  • Why Dewar swears by email marketing (and sends up to 15 campaigns a month).

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