The Operator

Ohad Sternberg

5M+ miles flown. 70 countries. 629 programs tracked. The person friends text at 11pm about whether to transfer to Aeroplan.

Ohad Sternberg
Ohad Sternberg
Essays by author
DearOhad

Weekend Edition / Dear Ohad...

Strategy Saturday

The Secret Economy of Hotel Booking: Why Third-Party Sites Exist, How They Rig the Game, and When Booking Direct Is the Only Power Move Left

Strategy Saturday

Black Friday, But Smarter: Earn Big, Burn Better (the UpNonStop playbook)

Hotels

The Great Loyalty Mirage: Why Hotel Chains Keep Devaluing Rooms While Pretending They’re ‘Dynamic’ (And How to Still Win in 2026)

Burn

The December Escape Playbook: How to Beat Dynamic Pricing, Win the Calendar, and Fly for Almost-Free When Everyone Else Overpays

Burn

The Dark Pools of Award Travel: How Airlines Run a Shadow Inventory You’ll Never See… Unless You Outsmart Them

DearOhad

Weekend Edition / Dear Ohad...

Strategy Saturday

2026 Predictions: The 7 Quiet Devaluations Coming (and How You Can Still Win Big)

Burn

The Most Underpriced Redemption in Award Travel: Dual-Seat Saver Inventory; Why You Profit When Airlines Slip?

Burn

The $6,580 Lie-Flat Lesson: How UpNonStop Turns a “Normal” Transatlantic Ticket into a Masterclass in Smart Redemption Strategy

Burn

The 72-Hour Panama City 🇵🇦 Redemption Playbook

Burn

The Hidden Gold Rush of November: How to Turn Transfer Bonuses + UpNonStop GPT Into Your Highest-Value Redemptions of the Year

Learn

The Points Tax You’re Already Paying (And How to Zero It Out)

DearOhad

Weekend Edition / Dear Ohad...

Strategy Saturday

How $100,000 in Points Can Give You a $20,000 Contract Advantage

Earn

The Earn Engine: Why Businesses Need a Chief Points Officer

Learn

The Redemption Curve: How to Predict the Next Devaluation Before It Hits

Return

Stack or Starve: The Real ROI Behind Every Point You Earn

Earn

The Bank War Beneath Your Wallet: How Chase, Amex, and Citi Are Weaponizing Transfers in 2026

Learn

The Vanishing Value: How Dynamic Pricing Quietly Killed Fixed Redemption Logic

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