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
Learn

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

→
Return

The Unclaimed $50,000: The ROI Math Your CFO Should Demand

→
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

→
DearOhad

Weekend Edition / Dear Ohad #36

→
Strategy Saturday

How Airlines Suddenly Make Money on Debit Cards Again

→
Strategy Saturday

Your Hotel Points Are Lying to You: The Brutal Truth About Hyatt, Marriott, and Hilton in 2025

→
Earn

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

→
Earn

The 2-Cent Club: Why Your Points Are Worthless Until You Burn Them Right

→
Earn

The $250,000 Oversight: Why Most Businesses miss 8% of Their Points Every Year

→
Case Study

The Pittsburgh Upgrade: How a Law Firm Turned Flexible Points into First-Class Morale

→
DearOhad

Weekend Edition / Dear Ohad #35

→
Strategy Saturday

How to Build a 12-Month Travel Calendar Around Your Company’s Spend Cycles

→
Burn

$7,532 Business-Class Redemption from 100,000 Points (11.8% Return)

→
Burn

The Accountant, the Avios, and the Lapland Winter | Or: How we saved him $21,285 in Cash

→
Burn

From Dental Equipment to Deluxe Suites: How a Miami practice owner turned $80K/month spend into a Buenos Aires 4-night luxury stay for 120K points

→
Burn

$9,937 Business-Class Redemption from 77K Chase Ultimate Rewards Points: How a Dallas HVAC CEO Turned Six-Figure Monthly Spend into a Christmas on the A380

→
Burn

$8,785 Business-Class Redemption from 287,000 Points: How a NYC Restaurant Owner Turned $100K+ Spend into Luxury Travel (Hint: 11.8% Return)

→
DearOhad

Weekend Edition / Dear Ohad #34

→
Strategy Saturday

How 179,000 Amex Points Became $18,380

→
Saturday Dispatch
Get the week's best insights.

Free. Saturday 06:00 ET. Unsubscribe anytime.

Subscribe for free