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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 ?

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.

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.

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

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

There’s a trillion-dollar market floating above your head built on points you’ll never redeem. Every swipe fuels it. Every delay funds it. Airlines don’t sell seats; they sell your patience. The Ghost Economy isn’t a reward system - it’s the most profitable debt ever invented 👻

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

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

“Double points” sounds like a win. It’s not. Most multipliers are smoke and mirrors - inflated earn rates hiding weak redemptions. The real metric isn’t 2x or 5x. It’s Return on Spend - what your dollar actually yields when you cash those points for real value, not brochure math.

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

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

Points aren't free money. They are taxable leverage hiding in plain sight. Earn them wrong, and the IRS calls it income. Use them right, and they become tax-efficient capital. The game isn't just earning and burning - it's knowing when uncle sam wants his slice.

The Chase Sapphire Countdown: Everything You Must Do Before the "Reserve" Revamp on Oct 26

The Chase Sapphire Countdown: Everything You Must Do Before the "Reserve" Revamp on Oct 26

Chase Sapphire Reserve changes on Oct 26. Points, perks, fees - everything is being rewritten. The next few days decide if you secure maximum value or leave thousands of points stranded. Act fast, plan carefully, or risk losing what you’ve earned.

CapitalOne Miles: The End of Easy Value (Q4-2025 Field Manual)

CapitalOne Miles: The End of Easy Value (Q4-2025 Field Manual)

CapitalOne built its empire on simplicity: flat earn rates, frictionless redemptions, and marketing that made points feel like cash with wings. That model doesn’t work anymore... Today their miles are fighting for definition in a world where partners are tightening, and arbitrage is vanishing.

Citi "ThankYou" in Q4-2025: When "Strata" Tries to Reforge Loyalty

Citi "ThankYou" in Q4-2025: When "Strata" Tries to Reforge Loyalty

Citi didn’t just rename a rewards card in 2025. It relaunched an entire worldview: "ThankYou" points are no longer a backwater alternative to Chase or Amex. With the Strata family, it’s trying to make its points behave like a modern currency - flexible, timed, and fiercely contested.

Bilt Rewards in Q4-2025: How Renting Became a Loyalty Asset

Bilt Rewards in Q4-2025: How Renting Became a Loyalty Asset

Bilt started as a novel rent reward tool. By Q4-2025, it’s matured into a loyalty infrastructure: embedded in property ecosystems, battling for redemption real estate, and hinting at alliances beyond travel - maybe even with Rakuten.