FridAI - ChatGPT Did My Taxes?!

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Business Brain – The Entrepreneurs’ Podcast

Shannon Jean & Dave Hamilton

699 episodes

2 days ago

Two long-time small-business owners, Dave Hamilton and Shannon Jean, come to you each week to talk through the trials, success, pitfalls and tips it takes to successfully run a small business in today's world. Hear real-world folks talk about real-world problems, letting you know not only what it takes to get it done but that you're not alone in doing it!

All content for Business Brain – The Entrepreneurs’ Podcast is the property of Shannon Jean & Dave Hamilton and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.

FridAI - ChatGPT Did My Taxes?!

Business Brain – The Entrepreneurs’ Podcast

24 minutes 31 seconds

4 weeks ago

FridAI - ChatGPT Did My Taxes?!

Dave and Shannon open Casual Friday with a Shopify nod, then spotlight listener David’s “vibe-coded” Replit app for high-school sports. His web iPad tool tracks scoring, fouls, streaks, and biggest leads, exports structured summaries to an AI project, and let him publish recaps before leaving the gym. The hosts urge productizing it as a simple SaaS for local media and parents, noting how low-code iteration unlocks niche, high-value workflows.
Listener Ian contributes a prompt to reduce ambiguity in text communications—analyze likely interpretations, confirm intent, then offer two clearer rewrites—which sparks a broader discussion about using AI to keep customer-service tone friendly over SMS. Shannon then explains how he used ChatGPT for tax prep: export a Gmail “receipts” label via Google Takeout, auto-extract 2024 transactions, categorize them, cross-check with credit-card summaries (dedupe, find misses), and organize 1099s/K-1s for his accountant—plus a “what am I wasting money on?” audit to cut subscriptions. They close by inviting listeners to send their own AI workflows to feedback@businessbrain.show.

00:00:00 Business Brain – The Entrepreneurs’ Podcast #693 for Casual FridAI, October 17, 2025

October 17th: National Clean Your Virtual Desktop Day

00:01:16 David-Replit vibe-coded me an app I wanted!

00:08:00 Ian-FridAI-Here’s a prompt to help reduce communication ambiguity
PROMPT: Analyze my text for possible interpretations. Rank them by likelihood based on how most readers would understand the wording. Ask me to confirm which meaning I intend. Then, provide two alternative rewrites that eliminate ambiguity while preserving my tone: [paste text here]

00:10:00 Beware of customer service handling via text. You have to go over the top to be friendly.
00:13:40 SPONSOR: Shopify – For anyone to sell anywhere, sign up for a one-dollar-per month trial period at Shopify.com/BusinessBrain and upgrade your selling today!
00:15:17 Shannon: ChatGPT Did My Taxes

Google Takeout
Is this a prison decision or a penalty decision
Upload your credit card statement to ChatGPT and ask it, “what am I wasting my money on? Be harsh. Tough love.”

00:23:55 Business Brain 693 Outtro

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