Paying Taxes With a Card: Processors And Tradeoffs

#263: Chris breaks down exactly how he’s earned millions of points and miles, and why simplicity matters more than optimization. He covers signup bonuses, spending strategies, credit score impacts, business cards, cash-back alternatives, and how to decide when a card (or perk) is actually worth it.

Link to Full Show Notes: https://chrishutchins.com/points-and-miles-simplified-credit-cards

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Resources Mentioned

Credit Cards: Best Cards Page

• Alaska Airlines Visa®
• American Express® Green Card
• American Express Platinum Card for Schwab
• Atmos™ Rewards Summit Visa Infinite® Card
• Bank of America® Premium Rewards® Elite
• Bank of America® Unlimited Cash Rewards
• Bilt Palladium Card (Rates and fees here)
• Capital One Venture X Business
• Capital One Venture X Rewards Credit Card
• Citi® / AAdvantage® Executive World Elite Mastercard®
• Coinbase One Card
• Costco Anywhere Visa® Card by Citi
• Hilton Honors American Express Aspire Card
• Robinhood Gold Card
• The Business Platinum Card® from American Express
• U.S. Bank Altitude® Reserve Visa Infinite® Card
• Venmo Credit Card
• Wells Fargo Autograph℠ Card

Rakuten: Free $50 here

Business Payment Platforms: Plastiq | Melio

IRS Authorized Payment Providers

• Pay1040
• ACI Payments

Reddit: Credit Card Spend Needed to Achieve Each Airline Status Tier

ATH Podcast

• Chris' Credit Card Optimizer Tool
• Ask Chris Anything!
• Membership
• Gift Card Site
• Ep #164: Earn Points Paying Taxes with a Credit Card (+ Latest Deals/News)
• Ep #200: Debunking Tax Myths, Avoiding Audits and Maximizing Savings with Jasmine DiLucci
• Ep #221: Deep Dive on Credit Reports, Scores, and Their Real-World Impact
• Ep #247: Deep Dive on Bank of America Credit Cards (Up to 5.25% Cash Back)
• Ep #248: How to Stop Over-Optimizing and Focus on What Matters with Tim Ferriss
• Ep #258: My Top 5 Mistakes with Points & Miles
• Ep #261: Goals, Tools, and Mindset Shifts for a Better 2026 with Kevin Rose
• Leave a review: Apple Podcasts | Spotify
• Email for questions, hacks, deals, and feedback: podcast@allthehacks.com

Full Show Notes

(00:00) Introduction
(01:26) How Chris Has Earned 15+ Million Points
(03:46) Why Signup Bonuses Still Matter More than Everything Else
(05:04) The Role Everyday Spending Actually Plays
(08:42) When Transfer Bonuses Are Worth It
(12:24) How Chris Leverages Referral Bonuses
(13:24) What Having "Too Many" Credit Cards Really Does to Your Credit Score
(16:13) How Many Signup Bonuses per Year Is Reasonable?
(16:44) Why Spend Requirements Are the Real Bottleneck
(18:23) Approval Odds and Timing Applications
(22:04) Getting Approved for Business Cards (Without A Business)
(27:23) Maximizing Rewards without Overcomplicating It
(30:18) When Cash Back Is the Better Option
(32:48) Best Cards for Big, One-Time Expenses like Weddings
(37:24) Making Sense of Card Rules and Restrictions
(38:13) Annual Fees: How to Decide if They're Worth Paying
(41:12) Paying Taxes with a Credit Card
(46:28) How to Think about Points if You Mostly Care about Hotels
(49:10) Is CLEAR Worth It?
(51:48) How DoorDash Credits Work
(53:25) Is There a Shortcut to Airline Loyalty Status?
(57:04) The Best Credit Card for Costco Spending
(59:19) Are the New Bilt Cards Actually Bad?

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