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

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...

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...

Strategy Saturday

How 179,000 Amex Points Became $18,380

Presidents Club

The President's Club Paradox: How a Free Trip Cost Millions Until It Didn’t

Learn

The Ghost Economy: How Unredeemed Points Became the World’s Most Profitable Liability

Learn

The Miles Multiplier Myth: Why “Double Points” Isn’t Always Double Value

Learn

Points & Taxation: What the IRS Doesn’t Tell You About Your Miles

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