
10 Questions to Ask Your AI Advisory Board This Week
Most founders know they should be asking better questions. Here are 10 specific prompts to get real value from your AI advisory board this week.

Most founders know they should be asking better questions. Here are 10 specific prompts to get real value from your AI advisory board this week.

You've been using ChatGPT as a business advisor. Here's why that's like asking a stranger for directions in a city they've never visited.

Your AI advisor can only give you relevant advice if it knows your business. Here's how uploading your pitch deck changes the quality of every conversation.

MCP integration means your AI advisory board lives inside Claude and ChatGPT — not in a separate tab you have to remember to open. Here's why that matters.

Six months ago I fired my $3,000/month business coach and replaced him with an AI advisory board. Here's the honest breakdown — what I lost, what I gained, and why I won't go back.

AI coaching and executive coaching are not the same thing. Here's an honest look at where each one wins — and where it doesn't.

A SaaS founder asked one question — "Should I raise prices?" — and made a $40,000 decision in 10 minutes. Here's what that conversation actually looked like.

I used to spend four hours a week consuming business content. Now I spend four minutes asking questions and getting answers. Here's what I do with the other 3 hours and 56 minutes.

An MBA costs $150k and takes two years. The right newsletter subscriptions cost $0 and deliver more current, more practical business education. There's just one problem.

Solo founders make worse decisions. Not because they're dumber, but because they don't have anyone to say "have you considered this?" Here's how to build a board of advisors without giving up equity.

I had 48 hours to prepare for an investor conversation and zero fundraising experience. My newsletter archive had more VC advice than I realized. Here's how I turned it into a crash course.


I cancelled my $400/month coaching program and replaced it with an AI advisory board built from my newsletter subscriptions. Three months later, here's what actually happened.


A good business advisor costs $500/hour and is available when they're available. AI advisors cost $20/month and are available at 2am when you're spiraling about a pricing decision. Here's how to use them well.


I spent almost $5k on coaching last year and retained maybe 15% of it. So I went looking for AI tools that could hold onto the wisdom my brain keeps losing. Here's what I found.