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Ohad Sternberg

The US to Southeast Asia Playbook: Best Redemptions Right Now

The US to Southeast Asia Playbook: Best Redemptions Right Now

Want lie flat to Bali, Bangkok, Singapore without torpedoing your points? Our August 2025 playbook shows real seats you can book tonight. KrisFlyer nonstops at 107k. Aeroplan at 87.5k plus 5k stopovers. Qsuite from 95k. LifeMiles low cash. (Hint: SMBs turn spend into Premium Seats)

Weekend Edition / Dear Ohad...

Weekend Edition / Dear Ohad...

This week in miles & points: United killed the stopover trick, Alaska launched a new program, Turkish ran a flash sale, Singapore pushed Spontaneous Escapes, and Delta dropped one of its wildest SkyMiles deals yet - here’s what actually matters for your points right now.

The Lie of “Dynamic Pricing”

Strategy Saturday

The Lie of “Dynamic Pricing”

“Dynamic pricing” isn’t innovation - it’s obfuscation. Airlines and hotels dress up yield management as progress, but the math hides a truth: you’re paying more for less. This Strategy Saturday tears apart the myth, exposes who profits, and shows how points are your only real hedge against the lie.

The Rewards Ponzi (And Why It Keeps Working)

The Rewards Ponzi (And Why It Keeps Working)

If everyone’s “winning,” who’s paying? Answer: the merchants and the suckers paying 19.99% APR | Or: Why Everyone Keeps Playing Even Though It’s a Rigged Game?

The Bank in Your Wallet

The Bank in Your Wallet

Think airlines run the points game? Cute. The banks own the house, mint the chips, and set the odds. Every swipe funds the show: cheap miles bought in bulk, annual fees as cover charge, and interest as the trapdoor. Your “free” trip? A payout planned on their spreadsheet.

The Rewards Cartel: Hotels do not fly planes, but they sure as hell sell points.

The Rewards Cartel: Hotels do not fly planes, but they sure as hell sell points.

Hotels don’t fly planes - they mint currency. Every swipe of a Hilton or Marriott card prints points sold to banks for cash, then redeemed for rooms that cost pennies. Your “free” night? Margin play. The buffet cost more. Dynamic pricing quietly taxes your balance. Burn fast or get devalued.

Airlines Are Banks That Happen to Fly Planes

Airlines Are Banks That Happen to Fly Planes

Airlines aren’t in transport - they’re minting money. United sold $6B+ in miles to banks at ~1¢; you redeem at 2–5¢ while dynamic pricing and breakage pad profit. The planes are props. The real business? A spreadsheet that prints cash.

The $100 Avocado

The $100 Avocado

What Actually Happens When You Buy Groceries With a Credit Card | Or: A person walks into Trader Joe’s and pays $100 dollars with an American Express. Where does that money go? | Spoiler: Trader Joe’s does not get 100 dollars.

Weekend Edition / Dear Ohad...

Weekend Edition / Dear Ohad...

This week in miles & points: You blinked, United’s flash sale was gone, Qantas just yanked value, Southwest is testing free Wi-Fi, JetBlue renamed everything, and Choice Hotels quietly gives insane deals - here’s what actually matters for your points right now...

Redemption Architecture: How to Lock in Maximum Cents-Per-Point Value

Strategy Saturday

Redemption Architecture: How to Lock in Maximum Cents-Per-Point Value

Most SMBs treat points like loose change: spend them fast, take the 1¢, move on. That’s the rookie play. The real game is Redemption Architecture: engineering every burn to hit 3¢–10¢ per point so your “rewards” become a six-figure travel asset, not a line item buried in your budget.

From Hard Hats to Hawaiian Sunsets: A Texas Contractor’s $2.3M Points Makeover

From Hard Hats to Hawaiian Sunsets: A Texas Contractor’s $2.3M Points Makeover

A Dallas construction firm was earning just $23K in cashback on $2.3M spend until a golf course chat revealed a hidden goldmine. By swapping cards and targeting bonuses, they turned the same expenses to $210K of luxury travel, from Maui retreats to European getaways, unlocking a game-changing edge.

From Boring Cashback to $123K in First-Class Travel | Inside a Florida Dental Clinic’s Points Makeover

From Boring Cashback to $123K in First-Class Travel | Inside a Florida Dental Clinic’s Points Makeover

A Florida dental clinic was earning $11K a year in boring cashback on $1.1M of expenses. Then they swapped cards, optimized categories, and now pull $123K in premium travel - booking lie-flat seats, luxury resorts, and bucket-list trips straight from their operating expenses.