UpNonStop: More 🏝️ • Less 💰 • Smart 🍪 (Page 2)

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

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

Your business isn’t just spending, it’s paying a hidden Points Tax. Invisible on your P&L, untracked by your accountant, undisclosed by banks, it silently drains value whenever loyalty points are mismanaged, under-earned, or redeemed below their true worth.

Weekend Edition / Dear Ohad...

Weekend Edition / Dear Ohad...

Sam spends $600K a year on cards but his points were just sitting there. What if he could use points to close deals, impress vendors, and accelerate contracts without touching cash? Here’s how businesses turns points into silent negotiation power.

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

Strategy Saturday

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

You read that right. Most companies think of reward points, miles, and loyalty credits as something to rack up, redeem for travel, or hand out to employees. But what if your points weren’t just a perk - they were a negotiation tool ?

The Earn Engine: Why Businesses Need a Chief Points Officer

The Earn Engine: Why Businesses Need a Chief Points Officer

Your wallet is leaking millions you didn’t know you had. Every point your business earns is untapped profit - ignored, mismanaged, or wasted. A Chief Points Officer stops the drip, turning invisible loyalty into a weaponized engine for growth.

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

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

Devaluations don’t crash... they creep. One tweak, one partner pull, and your million-point cushion turns into loose change. The smart money hedges before the drop. Spot the pattern, move first, and ride The Redemption Curve while everyone else is still earning yesterday’s rate.

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

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

Your points aren’t perks - they’re profit. Stack the right cards, time your transfers, and your business 2% cashback ceiling becomes a 10% ROI engine. The game isn’t earning... it’s burning smart. Miss the stack, miss the margin. Stack or starve.

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

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

Fixed charts are dead. Airlines & hotels now flex points dynamically - miss the strike window, and you overpay. SMBs who master timing, partner arbitrage, and strategic transfers turn every swipe into predictable ROI. Stop chasing points - make them work for you.

Weekend Edition / Dear Ohad...

Weekend Edition / Dear Ohad...

Josh wants to take his wife and three kids to London for Spring Break. With Chase’s 40% Virgin bonus, transferring 125K points instead of spending 350K-800K in the portal can save him thousands. If he finds five saver seats, that’s a 6–9% return... real yield, not status.

How Airlines Suddenly Make Money on Debit Cards Again

Strategy Saturday

How Airlines Suddenly Make Money on Debit Cards Again

Airline debit cards are back, but not for your benefit. United’s new MileagePlus Debit Card isn’t about rewarding spending; it’s about mining deposits, exploiting small-bank loopholes, and turning your checking balance into their next billion-dollar loyalty engine.

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

Strategy Saturday

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

Hyatt. Marriott. Hilton. Three loyalty giants but only one delivers real ROI. We broke down footprint, transfer math, and cents-per-point to find out which program turns your company’s travel budget into profit. Spoiler: it’s not who you think.