How Much Will World Cup Players Pay in Taxes & Xero's New AI Agent Builder

What do World Cup taxes, AI-built accounting tools, and remote work have in common? In this episode, Blake and David unpack how tax rules hit global athletes and sports bettors, why Xero’s new AI products signal a shift toward accountants building their own software, and where firms still face risk with audit standards, cybersecurity, and homegrown apps. You’ll also hear what’s really happening with remote work and a listener correction on Trump accounts.


Chapters
  • (00:00) - Cold Open and Welcome
  • (00:27) - World Cup Chat Setup
  • (04:04) - World Cup Player Taxes
  • (06:58) - Betting and Prediction Taxes
  • (09:47) - Xerocon London Highlights
  • (12:58) - Xero Ultra Midmarket Push
  • (15:31) - Xero Force Agent Builder
  • (20:56) - More Xero Updates
  • (23:22) - App News Canopy Close
  • (26:13) - TaxDome Kiosk In Person
  • (27:34) - Rippling Banking Payroll
  • (29:37) - Exit Readiness Pitch
  • (30:30) - AI Audits Need Rules
  • (32:40) - QC 1000 Rollbacks
  • (35:58) - CBIZ Activist Pressure
  • (39:04) - Vibe Coding Boom
  • (40:41) - DIY Tools Hidden Risks
  • (48:05) - WISP Versus Security
  • (48:57) - Remote Work Reality
  • (50:13) - AI Usage Cost Chaos
  • (54:13) - Trump Accounts Correction
  • (58:23) - AI Handles CPE Reporting
  • (01:01:13) - CPE Plug And Farewell
 

Show Notes
World Cup players face tax penalties
How Much Will World Cup Players Pay in Taxes? In 2026, FIFA is the Real Winner
World Cup Betting Tax Rules Differ for Prediction Markets, Sportsbooks
Xero CEO on AI, the builder class and Xero at 20
How we're building Xero to scale with growing businesses
Introducing XeroForce: Your no code custom AI agent builder for financial workflows
Paying your bills just got cheaper: Standard ACH is now free in Xero
Xerocon London 2026: The Agentic Era Has Arrived for Small Business Finance
TaxDome Launches Kiosk: The In-Person Client Experience, Now Digitally Integrated
Rippling Launches Business Banking
MindBridge urges clearer PCAOB guidance on AI audits
PCAOB Issues Proposed Amendments to QC 1000 and Seeks Public Comment
Restarting the M&A Flywheel — CBIZ, Inc.
Starbucks starts vibe coding enterprise stack
Software vendors aren't losing sleep over vibe-coding — yet
Most accounting firms can be impersonated by email – we checked 275 of them
Despite return-to-office crackdowns, remote work is alive and well as the rate has barely changed over the last two years
AI bills are baffling the C-suite after shift to usage-based pricing


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Transcripts
The full transcript for this episode is available by clicking on the Transcript tab at the top of this page

Creators and Guests

David Leary
Host
David Leary
President and Founder, Sombrero Apps Company
How Much Will World Cup Players Pay in Taxes & Xero's New AI Agent Builder
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