Meet Brennen Bliss, CEO of Propellic, a digital marketing agency serving travel companies. After 10 years in business, Bliss has turned his company’s expenses, including $200,000 in annual estimated tax payments, into luxury travel experiences worth more than $75,000 per year.

Right now, Bliss is traveling across Asia on a trip that would have cost $40,000 out of pocket, but he’s paying far less, thanks to points earned from business spend.

The Numbers That Matter

Monthly business spend: $150,000 (growing to $750,000 over the next six to 12 months)

Monthly points earned: 200,000 to 400,000 points

Annual rewards value: $75,000+

Top spending categories:

  • Advertising spend
  • Flights for business travel
  • IRS/treasury (estimated tax payments)
  • Hotels
  • General business expenses
Man calculating tax payments using receipts, smartphone, and laptop at a desk.

The Tax Payment Unlock

One of Bliss’s biggest points generators? His estimated tax payments.

“I pay about $200K in estimated taxes annually,” Bliss said. For business owners sitting on large quarterly tax bills, this represents a massive opportunity to earn points on money you’re already required to spend.

A Strategic, Not Chaotic, Card Setup

Unlike many points enthusiasts who constantly chase welcome bonuses, Bliss takes a different approach: strategic category optimization without the hassle.

“I really haven’t been chasing sign-up bonuses,” he said “Too much work with Quickbooks setup, etc.”

Instead, he’s built an 11-card portfolio where each card has a specific purpose.

For advertising spending (his biggest category):

For travel:

For hotel stays:

For everything else:

Loyalty focus: American Airlines, Chase Ultimate Rewards, American Express Membership Rewards, Capital One Miles

The strategy is working. Bliss is on track for Concierge Key status with American Airlines this year with more than $60,000 in flight spend, plus full-fare international tickets.

The Current Trip: Proof in Practice

As we write this, Bliss is in Asia on an itinerary that showcases the real-world value of business points.

Flights (two passengers):

  • Los Angeles – Singapore – Bali in Singapore Airlines business class
  • Bali – Singapore – Vietnam in Singapore Airlines business class
  • Bangkok – Hong Kong – Los Angeles in Cathay Pacific first class

The Growth Multiplier

What makes Bliss’ story even more compelling? His business is scaling dramatically.

Current monthly spend of $150K is projected to grow to $750K per month as Propellic becomes the agency of record for larger clients, spending on their behalf.

If he’s currently earning between 200,000 and 400,000 points monthly at $150K spend, that could mean 1 million to 2 million points per month at the new volume, which is enough for multiple aspirational trips annually.

Business owner hanging an open sign on her shop door.

The Bottom Line for Business Owners

Brennen’s approach offers a blueprint for business owners who want to maximize rewards without adding complexity:

  1. Find your big spend categories and optimize cards for them. For Bliss, it’s advertising spend and tax payments.
  2. Don’t chase every bonus. Pick cards with strong category earnings and stick with them.
  3. Use your normal accounting tools. No need for complex tracking systems.
  4. Let business growth multiply your rewards. More revenue means more spend means more points.

When you’re spending more than $150,000 monthly on legitimate business expenses, the points aren’t a side hustle. They’re a significant benefit that can fund incredible travel experiences you might not otherwise take.

For Bliss, that means flights in premium cabins to Asia, stays at some of the world’s finest hotels and the freedom to travel in a style that would be prohibitively expensive if paying cash.

Want to build out your own card portfolio for your business? Check out our list of best cards for business owners to find the best offers for your business.