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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

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

Hotels don’t hate Expedia because of commissions - they hate them because OTAs own the guest before they ever arrive. The entire system is a rigged economy of hidden rates, silent penalties, and loyalty blackouts. Book wrong, and you’re not a “guest”… you’re inventory.

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

Strategy Saturday

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

Black Friday is the shopping holiday that ate the calendar and then asked for seconds. For points nerds and SMB finance managers alike, it’s less about impulse buys and more about micro-arbitrage: stacking discounts, category multipliers, portals, and transfer promotions until the math cries uncle.

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

Strategy Saturday

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

If you think 2024 and 2025 were chaotic in points land, buckle up. The next 12-18 months are shaping up to be the most consequential era for business travel value since the first bank slapped a bonus category on a metal card and called it innovation.

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 ?

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.

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

Strategy Saturday

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

Stop earning points blindly. We're building you a 12-month travel calendar that ties every dollar of spend to a specific redemption. Forecast points, plan transfers, and redeem strategically - turning business travel from an expense into a predictable 10% ROI engine.

How 179,000 Amex Points Became $18,380

Strategy Saturday

How 179,000 Amex Points Became $18,380

Six seats. $18,000 each. Sold out months in advance. Yet our Orlando accountant flew Japan Airlines First Class for 179,000 points - turning $47K of business expenses into $18K of tax-free yield. That’s not luck. That’s 39% Return on Spend hiding in his ledger.

Your Strike Window: The 48-Hour Premium Award Release

Strategy Saturday

Your Strike Window: The 48-Hour Premium Award Release

There’s a moment, about two days before takeoff, when the entire airline yield system exhales. Corporate no-shows get processed. Fare fences relax. Inventory algorithms stop pretending to be in control. And somewhere in that chaos, a few premium seats quietly surface - often for miles, not money.

The Spend Stack: How to Build a Self-Funding Business

Strategy Saturday

The Spend Stack: How to Build a Self-Funding Business

You’re not losing money on bad sales - you’re losing it on bad spending. A Spend Stack flips expenses into assets by optimizing every dollar that leaves your business. When you manage cash flow, rewards, and redemption like capital, your company starts funding itself.

The Status Mirage: Why Business Owners Chase Airline Status the Wrong Way, Burning Cash Instead of Optimizing Points (And How to Flip the Script)

Strategy Saturday

The Status Mirage: Why Business Owners Chase Airline Status the Wrong Way, Burning Cash Instead of Optimizing Points (And How to Flip the Script)

Greatest trick the airlines ever pulled: convincing business owners that status is the crown jewel of travel. Those shiny elite cards in your digital wallet? They feel powerful. They unlock upgrades, lounges, priority boarding. They’re also six figures in wasted value every year. Here's why...

Saturday Surge: The 48-Hour Window for Sneaky Award Space

Strategy Saturday

Saturday Surge: The 48-Hour Window for Sneaky Award Space

📆: Airlines quietly dump unsold premium seats late Friday, opening a 48-hour award bonanza. Strike Saturday or lose to Monday’s business rush - keep points liquid, move fast, and lock lie-flat seats for a fraction of the cash fare before the dynamic pricing tide snaps shut.