The client you should fire
You found your best clients. Now look at the other end of the list.
Latest
When someone asks AI, do you show up?
A regular search now opens with an AI answer. Are you in it?
Your time is money
The work that's quietly eating your week.
Your no-show math
Pull last month's no-show count. Then turn on one thing.
The discount you're about to run
The slow week is not a discount problem.
How to spot your best clients in your data
The trap most service businesses fall into when describing their "ideal client" is feel-words. Loyal. Easy. Aligned. Useless, because every existing client believes they fit them. Here is the definition you can pull from data.
You don't need more clients.
A founder I had coffee with last month finished her best-revenue quarter ever and looked exhausted. I asked what she was working on next. "Pipeline. We need more clients." Then she paused.
The clients who quietly left
Last week we talked about the clients who stay. Today is the other side of that list: the ones who used to come every six weeks and just stopped. They did not leave. You misplaced them. Here is how to find them and the three-line note that brings them back.
The price you're afraid to charge
A salon owner told me she has not raised her color price in four years. When I asked why, she said the sentence I hear every week: "I'm afraid I'll lose them." Then we pulled her client list.
Instagram says AI can build you a business in 24 hours. It can't.
The viral "build a business in 24 hours" prompt list produces ten beautiful documents and zero customers. Here's where each prompt earns its keep, and where it lies.
Your top 10 customers, and the one to reach out to this week
Most owners can name their three regulars. The other seven are where the money is hiding. The customer audit to do this week.
I lost my domain for 40 days
It started with a renewal email I never saw. 40 days later: who actually owns your business online.
Simplify in 3: AI can't fix messy data. Here's a 30 min Sprint
Simplify in 3: Three tips every two weeks to grow your business, stay organized, and save time without the overwhelm. Hi [FIRST NAME GOES HERE] Before: You tried ChatGPT for you...
Building In Public
Simplify AI Update: Graduating FI + What I am building, and what I need
Issue #3 of the Simplify AI investor update: Founder Institute graduation, where we stand today, what feedback taught us, and my asks.
Productivity
Simplify in 3: 5 minutes before any meeting - here’s your cheat sheet
Stop the pre-meeting panic. Three simple habits that turn 15 minutes of inbox archaeology into 2 minutes of calm preparation — plus an AI prompt you can use today.
Building In Public
Building in Public #2: I found my co-founder, chose the scary pricing, and I need your honest opinion
Issue #2 of Building in Public: How I found my co-founder, why I chose a value ladder over subscription pricing, and the marketing pivot that changed everything. Plus three questions I need your honest answers on.
Follow Up
Simplify in 3: The "set it and forget it" system for staying top of mind
Stop letting leads go cold. Three actions to automate your follow-ups without sounding like a robot — plus an AI prompt that gives you handwritten-note thoughtfulness in 2 minutes.
Quarterly Planning
Simplify in 3: Plan Your Q1 in 30 Minutes with AI
New quarter, blank page, familiar overwhelm? Three steps to plan a focused Q1 in 30 minutes using AI as a thinking partner — plus a planning prompt that replaces a full strategy session.
Year In Review
Simplify in 3: What Actually Mattered in AI for Small Businesses in 2025
A year-end look at what actually mattered in AI for small businesses in 2025: the game-changer, the panic that flopped, and what's coming in 2026. Plus a reflection prompt to close out the year.
Agentic AI
Set up these 3 automations before 2026 (no coding required)
Your LLM can now connect to your email, calendar, and files. Three no-code automations to set up before 2026 — plus a 'chief of staff' AI prompt that ties them all together.
Building In Public
Building in Public: My Journey to Simplify
Issue #1 of Building in Public: The full story of why I started Simplify Digital AI — 20 years at Cisco, the gap between enterprise tools and small business reality, and what's slowing us down right now.
AI Hallucinations
Simplify in 3: When your AI Lies to You
3 ways to stop AI mistakes before they hurt your credibility or client trust. Spot hallucinations, question confident answers, and match AI to the right tasks — with four real-world disasters to learn from.
Cybersecurity
Simplify in 3: Stop spam, phishing & protect your money
30 minutes to stop phishing, secure your accounts, and protect your money. Cybersecurity Awareness Month: three concrete actions for small business owners, plus the password manager I recommend.
AI Tools
Simplify in 3: AI tools that actually save time (and don't add stress)
29,000+ AI tools on the market, but you only need a few. Four tools I actually use (Claude, Descript, Read.ai, TidyCal), four matching prompts, and a 3-question test before you add another tab to your life.