Milenomics ² Podcast - No Annual Fee Edition TravelStories Episode 71: A Wide Ranging Conversation with Gary Leff
Jan 8, 2026
Gary Leff, a frequent travel industry commentator and the voice behind View From the Wing, joins to share his vast knowledge on airline loyalty programs. He discusses the evolution of these programs, shedding light on the changing landscape of upgrades and the value of mid-tier status. Family travel takes center stage as Gary offers practical tips for traveling with kids and highlights the deeper emotional connections that travel fosters. He also hints at the future of personalized experiences and the potential of emerging loyalty strategies.
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When Free Breakfast Broke A Hotel
- Gary recalls Freddie Awards at a Hilton overwhelmed by guests with newly acquired Gold status causing a three-hour breakfast line.
- That experience illustrated how status promotions can unexpectedly strain operations and guest experience.
Upgrades Have Been Monetized, Not Promised
- U.S. airlines historically gave unsold premium seats to elites, but now sell many seats and monetize upgrades heavily.
- Marketing still promises upgrades while actual availability and complimentary upgrade rates have dropped dramatically.
Favor Mid-Tier Status For Practical Value
- Aim for mid-tier airline status because it delivers most practical benefits like extra-legroom confirmations, priority boarding, and checked bag exemptions.
- Avoid overinvesting to chase top-tier perks that have become rarer and less reliable.