The Tom Woods Show Ep. 2757 Will the Billionaires Unseat Massie? Cliff Maloney's Strategies for Election Victories
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May 2, 2026 
Cliff Maloney, CEO of Citizens Alliance and author of Run Right, is a political strategist who builds massive door‑knocking operations. He breaks down practical campaign mechanics. Topics include door‑knock ROI and canvasser tactics. He discusses balancing media buys with ground game, targeted messaging with the Leesburg Grid, fundraising realities, voter targeting, and tactics used in the Massie primary.
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Use Paid Door Knocking For High ROI Votes
- Do invest in paid door knockers because nine face-to-face conversations at the door produce one new vote on average.
- Maloney built large paid canvass teams (120 full-timers, 1,100+ applicants) to match Democratic ground games and prove doors win wars.
Sexy Media Can Mask Weak Ground Game
- Insight: TV and digital feel sexy but often underdeliver compared with targeted ground operations.
- Maloney: you need parity on media, but can't let opponents outspend you on paid canvassers and turnout work.
Use The Leesburg Grid To Focus Messaging
- Do run a Leesburg Grid messaging exercise and narrow each quadrant to three core messages for clarity.
- The grid maps what you want voters to think about you, your opponent, and opponent messaging to focus campaign communications.
