When Two Entrepreneurs Took the Same Road and Ended Up in Different Universes

🎧 Always Turn Left: Unlock Hidden Wealth | Transform Business Expenses into a Growth

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Picture this: it’s a Monday morning and two business owners are swiping their cards for everyday expenses. One is Dan, running a 20-person construction firm in Austin, Texas, juggling lumber, concrete, and subcontractors. The other is Maya, leading a boutique five-person digital marketing agency in Chicago, paying for ad campaigns, client travel, and software subscriptions.

Both spend roughly $750,000 a year. Both are disciplined, both are successful. Yet by the end of the year, their “returns” on that spend look wildly different. One treats rewards like spare change. The other treats them like a quietly compounding asset class that funds premium travel, impresses clients, and adds tangible value to her business.

Dan: The Flat-Cashback Comfort Zone

Dan owns Hill Country Commercial, a mid-rise construction business in Austin. His operations are straightforward: vendor payments for concrete and lumber, fuel for trucks, equipment rentals, and a handful of subcontractors.

He’s set on simplicity. Five years ago, his banker convinced him to use a single 2% cash-back business Visa. No categories to track, no points to transfer, no tracking charts - just a clean rebate on every purchase.

Reality check:

• Some vendors process payments through intermediaries that code as “utilities” or “miscellaneous,” which only earn 1.5%.
• Other expenses earn 2%.
• Blended earn rate: ≈1.8%.
• Annual rewards: ≈$13,500.

Dan redeems the rewards once a year as a statement credit. Five years of this approach yields roughly $67,500. Not bad - but capped.

His mindset is conservative. He enjoys the predictability and simplicity, but this approach leaves hundreds of thousands of dollars in potential value on the table.

Maya: The UpNonStop Flywheel

Nine hundred miles north, Maya runs Lakefront Creative, a small digital marketing agency in Chicago. Her expenses cover:

• Facebook, Google, and TikTok ad spend: $180,000
• Client travel and hotels: $120,000
• SaaS, payroll, and contractors: $150,000
• Miscellaneous operational spend: $300,000

Before partnering with us @ UpNonStop, she treated rewards like Dan did: a flat 2% cash-back card. Then she realized she was leaving value on the table.

Her Card Stack

With UpNonStop guidance, Maya built a multi-issuer card system that averages 3.2% effective earn:

This yields roughly 2.4 million transferable points per year, split across Amex Membership Rewards, Chase Ultimate Rewards, and Capital One Miles.

How She Redeems

Earning points is only half the equation; redemption strategy drives the true RoS.

Maya targets realistic mid-2025 award sweet spots. Examples include:

Flights Booked

Hotels Booked

Average redemption value: ≈2.5¢ per point, conservative but realistic when mixing high-value flights with hotel stays.

Crunching the Numbers

• Earn: 2.4 M points × 2.5¢ ≈ $60,000 in travel value per year
• Effective RoS: ≈8% - more than four times Dan’s 1.8%

Over five years, Maya’s approach would yield $300,000+ in premium travel - first-class flights, five-star hotels, and client-impressing trips. That’s enough to fund a new hire, launch a new service line, or enhance client retention with memorable experiences.

Why Maya’s Strategy Works

1. Flexible Currencies
   Amex, Chase, and Capital One points can transfer to 40+ airline and hotel partners. Flat cash-back cards can’t match this leverage.
2. Category Optimization
   Targeting 4–5x multipliers on big buckets - digital ads, flights, and shipping - turns ordinary expenses into a high-yield portfolio.
3. Smart Redemption Timing
   UpNonStop monitors partner award charts, so Maya books when premium cabins and peak-season hotels are available at favorable rates.
4. Compound Effect
   By reinvesting the value of rewards back into client travel, employee incentives, or marketing, Maya creates a self-funding growth flywheel.

Realistic Industry Data

UpNonStop tracks dozens of SMB clients, showing mid-2025 averages:

Top performers: marketing agencies, professional services, e-commerce sellers with heavy ad spend, and firms with frequent client travel.

Lessons for Small Business Owners

• Audit Spend Categories: Know what earns at 2x, 5x, or only 1x.
• Mix Issuers Strategically: No single card covers every high-value category.
• Redeem Intelligently: Target premium cabins, peak hotels, and points that deliver 2–5¢ per point.
• Track RoS Like ROI: If your annual spend hits six figures, a 2% cash-back return is tiny compared with an optimized 8% RoS.

The Bottom Line

Dan’s Austin construction firm earns $13,500 in “rewards” on $750,000 spend.
Maya’s Chicago marketing agency earns $60,000+ in value, plus client-impressing experiences, first-class flights, and premium hotel stays.

Same spend. Different choices.

The gap isn’t luck. It’s strategy.

If you’re a small or medium business owner, the difference between a flat 2% cash-back mindset and a points-as-an-asset approach can be hundreds of thousands of dollars over a few years.

That’s the quiet power of Return on Spend.

Are Your Points Working Hard Enough for Your Business?

Every dollar your company spends can either generate real travel value or sit idle. Our complimentary RoS evaluation shows you where you’re leaving opportunities on the table - and where you could be earning more.

We only run a handful of evaluations each week, so early sign-ups get the clearest picture first.