Field notes from indie retail.
Practical posts on running an independent store with AI in 2026.
- roadmap
The Shop With Me Year 2 Roadmap — What We're Building, What We're Not
A transparent look at Shop With Me's year-two roadmap. Bilingual expansion, deeper POS integrations, mobile companion app, multi-store admin, and opt-in surveillance.
Apr 28, 2027 - comparison
Remi vs AI Retail Competitors — An Honest Lay of the Land
A straightforward comparison of Remi against enterprise AI retail platforms and POS-vendor AI features. Different problems, different solutions, where each fits.
Apr 21, 2027 - roundup
The Best AI Tools for Independent Retailers in 2027
An even-handed roundup of AI tools for indie retail in 2027 - customer-facing, back-office, and marketing - with the criteria that actually matter at indie scale.
Apr 14, 2027 - founder
One Year of Shop With Me — What Worked, What Didn't, What's Next
A founder retrospective on the first year of Shop With Me — hardware, pricing, customer acquisition, product, and people. What we got right and where we missed.
Apr 7, 2027 - vertical
The Hidden Cost of Confusion in Liquor Store Customer Experience
What unanswered questions actually cost a liquor store. Real customer behaviors, the embarrassment factor, and the floor moments where revenue quietly leaks.
Mar 24, 2027 - founder
AI Retail Kiosk Lessons From Our First 100 Stores
A founder retrospective on what we learned from the first 100 stores running Remi - the integrations that broke, the assumptions we got wrong, and what we'd do differently.
Mar 17, 2027 - multi-unit
A Consistent Customer Experience Across Multi-Store Retail Without Losing Local Character
Practical playbook for standardizing the customer experience across 3-10 stores - templated responses, central training, and AI-driven baseline service.
Feb 17, 2027 - multi-unit
Scaling Indie Retail - What Changes When You Go From One Store to Five
The operational pain points that hit between store one and store five - communication, inventory variance, brand drift, staff turnover, and the ownership disconnect.
Feb 10, 2027 - opinion
Why Your Best Salesperson Is Probably the One You Just Hired
A contrarian take on retail sales training - why fresh staff outperform veterans on conversion, and how AI tools fit into a continuous training loop.
Jan 27, 2027 - ops
How to Run a Retail Technology Pilot Program Without Breaking Your Store
A 30-day retail technology pilot framework - scope, success metrics, exit criteria, and the difference between a pilot and a demo. From an indie operator.
Jan 13, 2027 - predictions
AI Retail Predictions for 2027 - What Indie Operators Should Watch
Nine predictions for indie retail technology in 2027 - from voice mode adoption and LLM cost decline to multi-store dashboards and biometric privacy rules.
Dec 30, 2026 - data
AI Retail Customer Questions — What We've Learned After Seven Months in Stores
After ~7 months running an AI concierge in real stores, the patterns in what customers actually ask are clearer. A category-level look at the data — observational, no inflated numbers.
Dec 16, 2026 - seasonal
New Year's Eve Liquor Store Sales — What Sells, What Doesn't, and the Mistakes to Avoid
NYE is the single highest-volume day of the year for many indie liquor stores. Here's a practical operator's playbook on inventory, last-minute customers, and common mistakes.
Dec 9, 2026 - seasonal
Holiday Liquor Store Tips — Practical Q4 Prep for Indie Operators
Inventory, staffing, gift bundles, age verification, and AI-mediated discovery — practical Q4 holiday prep for independent liquor store owners.
Dec 2, 2026 - founder
Indie Retail Technology — What Big-Box Gets Wrong, and What Indie Gets Wrong
Independent retailers and big-box chains both make predictable mistakes about retail technology. Specific category-by-category examples and what to do instead.
Nov 25, 2026 - founder
An AI Is Not a "Retail Employee" — Why the Language Matters
Calling an AI a "retail employee" sounds modern but creates legal and trust problems for indie stores. Here's what we call Remi instead, and why precision matters.
Nov 18, 2026 - launch
Introducing the AI Kiosk ROI Calculator — Methodology and How to Use It
Launching the Shop With Me ROI calculator for AI kiosks. Methodology, inputs, and how to interpret payback period, ticket lift sensitivity, and staff hours equivalent.
Oct 28, 2026 - ops
AI Retail Kiosk ROI — Worked Math for a Single Liquor Store
A transparent ROI walkthrough for deploying an AI retail kiosk in an independent liquor store. Real levers, real math, no inflated claims.
Oct 21, 2026 - comparison
Self-Checkout vs AI Concierge — Different Problems, Different Tools
Self-checkout speeds up the transaction. An AI concierge improves the decision. They solve different problems and most stores should run both. Here's when to deploy which.
Oct 14, 2026 - comparison
AI Upsell vs POS Prompts — Why "Want Fries With That" Fails in Indie Retail
Generic POS upsell prompts annoy customers and rarely lift average ticket in indie retail. Conversational AI does something different. Concrete examples and the math.
Oct 7, 2026 - technical
AI Retail Kiosk Hardware — What's Actually Inside Remi
A practical walkthrough of the hardware behind an AI retail kiosk. Why off-the-shelf tablets beat custom hardware for indie stores, plus power, network, and security notes.
Sep 30, 2026 - founder
The Great-Grandfather Test — How a San Diego Liquor Store Built an AI Concierge
Why every Shop With Me feature has to pass the "great-grandfather test." A founder note from Mike Yadago about family, retail, and AI you can actually trust.
Sep 23, 2026 - ops
7 Questions to Ask Before Buying Retail AI (A Checklist for Indie Operators)
A practical seven-question checklist for indie retailers evaluating AI tools. Data ownership, offline behavior, multilingual, integrations, ramp time, exit, and real-store proof.
Sep 16, 2026 - technical
POS Data Privacy for Retail Kiosks: What a Kiosk Should and Should Not Read
A clear-eyed framework for what data a retail kiosk should be allowed to read from POS, what should stay out, and a brief note on PCI compliance.
Aug 26, 2026 - comparison
Clover vs. Square for Liquor Stores: An Even-Handed Operator Comparison
Clover and Square both work for liquor stores. Hardware, fees, age verification, integrations, multi-store — here is the honest comparison without picking a winner.
Aug 19, 2026 - technical
How an AI Kiosk Integrates With Square POS (And What Square's API Actually Allows)
A practical look at how a kiosk-style AI assistant integrates with Square POS — what the OAuth flow looks like, what data flows, and what does not.
Aug 12, 2026 - vertical
AI for Independent Grocery Stores: The Most Underserved Vertical in Retail Tech
Independent grocery is the underserved retail tech vertical. Here is what shoppers actually ask, why chains cannot customize the way indies can, and where AI fits.
Jul 22, 2026 - education
The Top 10 Questions Liquor Store Customers Actually Ask (With Model Answers)
A staff-training resource covering the ten most common questions liquor store customers ask, with model answers for each that work on the floor.
Jul 15, 2026 - education
Wine Pairing for Liquor Store Staff: A Quick Reference That Actually Works on the Floor
A practical wine pairing guide for liquor store staff. Real examples by price tier, how to handle the I am not a wine person customer, and what to skip.
Jul 8, 2026 - ops
The Real Cost of Untrained C-Store Staff (And What an AI Kiosk Actually Replaces)
Convenience store turnover is brutal and training cost is real. Here is the operator's view of what an AI kiosk replaces versus what it cannot.
Jun 24, 2026 - vertical
Bilingual Customer Service in Liquor Stores: Why Spanish Matters and What Most Stores Get Wrong
Spanish-language service is a differentiator most indie liquor stores miss. Here is what bilingual signage misses and how a kiosk closes the gap without a bilingual hire.
Jun 17, 2026 - education
What Is an AI Store Associate? A Plain-English Definition for Indie Retail
An AI store associate is an in-store assistant that answers shopper questions, recommends products, and routes them around the store. Here is what it actually does.
Jun 10, 2026