Can ChatGPT Agent Mode Reconcile My Checking Account?

Can an AI reconcile your books while you sleep? Blake and David run a live experiment with ChatGPT-5’s Agent Mode in Xero—watching it match transactions, stumble on prepayments, and reveal what’s realistically automatable today. They also break down a flood of app news: Dext's bill pay, Ramp’s mega raise, Thomson Reuters and Deloitte’s agentic AI, plus Ignition–Financial Cents and Canopy portal moves. They dig into survey findings showing that 58% of employees are secretly using AI at work despite company bans, and take a look at how AI is disrupting the job market for college graduates.

Sponsors
TeamUp - http://accountingpodcast.promo/teamup
Relay - http://accountingpodcast.promo/relay
Human at Scale - http://accountingpodcast.promo/human
Missive - http://accountingpodcast.promo/missive

Chapters

• (01:32) - Exploring AI in Accounting
• (02:20) - Testing ChatGPT for Accounting Tasks
• (05:26) - Reconciling Transactions with AI
• (10:27) - App News
• (18:34) - AI and Automation in Accounting
• (23:29) - Recent Raises and Acquisitions
• (31:10) - Government and Regulatory Updates
• (35:14) - AI Agent Struggles with Prepayment
• (35:39) - VC Investments in Accounting Firms
• (37:43) - Ignition and Financial Sense Integration
• (40:13) - Canopy's Smart Intake and AI Innovations
• (42:58) - AI in the Workplace: Surveys and Insights
• (44:39) - AI Agent Finally Figures Out Prepayment
• (52:36) - AI's Limitations and Future Potential
• (01:01:55) - Fundraising and AI in Accounting Apps
• (01:12:28) - Impact of AI on the market
• (01:13:42) - Conclusion and CPE Information

 

Show Notes

Product Specialist-Accounting,AI - Xero

https://builtinlondon.uk/job/product-specialist-accounting-ai/6683466

Rillet raises $70M to replace 20th-century accounting software with AI-native ERP built by accountants

https://www.globenewswire.com/news-release/2025/08/06/3128328/0/en/Rillet-raises-70M-to-replace-20th-century-accounting-software-with-AI-native-ERP-built-by-accountants.html

AI accounting startup Rillet raises $70 million in Andreessen Horowitz, ICONIQ-led round

https://www.investing.com/news/economy-news/ai-accounting-startup-rillet-raises-70-million-in-andreessen-horowitz-iconiqled-round-4172975

Ramp Raises $500 Million at $22.5 Billion Valuation to Accelerate AI and Build the Future of Finance

https://www.prnewswire.com/news-releases/ramp-raises-500-million-at-22-5-billion-valuation-to-accelerate-ai-and-build-the-future-of-finance-302516953.html

Ramp hits $22.5B valuation just 45 days after reaching $16B

https://techcrunch.com/2025/07/30/ramp-hits-22-5b-valuation-just-45-days-after-reaching-16b/

IRS, White House clashed over immigrants' data before Billy Long was ousted

https://www.washingtonpost.com/business/2025/08/09/trump-administration-irs-data-dispute/

Trump replaces IRS Commissioner Billy Long with Scott Bessent

https://www.washingtonpost.com/business/2025/08/08/billy-long-irs-commissioner-bessent/

Trump ousts Billy Long as IRS commissioner, names Bessent acting head

https://www.cnn.com/2025/08/08/politics/billy-long-ousted-irs-commissioner

IRS Chief Forced Out After Immigrant Tax Data Pushback—Report

https://www.newsweek.com/irs-chief-forced-immigrant-tax-data-pushback-report-2111292

Billy Long