I interview ChatGPT (calling it Alex) and challenge it to create a roadmap from zero skills to $1M ARR in five years. We break down the best skills to learn (coding, sales), how to choose a profitable niche, and why B2B SaaS for remote creative collaboration is a strong bet. I dive into practical steps: market research, MVP building, pricing, and B2B outreach. I reflect on sales cycles, pricing strategy, and the impact of AI tools on entrepreneurship. I question bootstrapping, validation, and staying ahead as the landscape rapidly evolves.

Timestamps by PodSqueeze

Introduction and Episode Setup (00:00:00)  

Naming ChatGPT and Framing the Challenge (00:02:09)  

Defining “Rich” and Setting the Revenue Goal (00:03:10)  

Defining the Starting Point and Essential Skills (00:04:03)  

Learning to Code in the Age of AI (00:05:56)  

Timeline for Learning Coding Skills (00:07:09)  

Sales as an Alternative Path (00:08:02)  

Combining Skills and Setting the Five-Year Plan (00:09:22)  

Market Selection and Research (00:09:44)  

Examples of Promising Markets (00:10:58)  

Evaluating and Sizing a Market (00:12:01)  

How to Research and Validate a Market (00:13:01)  

Choosing the Best Market Right Now (00:14:06)  

Existing Tools in the Remote Work Space (00:14:43)  

Framework for Finding Opportunities in Remote Work (00:15:17)  

Selecting a Specific Problem to Solve (00:16:20)  

Zeroing in on a Concrete Product Idea (00:17:33)  

Distribution and Go-to-Market Strategy (00:18:13)  

Targeting and Reaching Decision Makers (00:19:19)  

Preparation Timeline for Outreach (00:21:02)  

Warming Up Specific Contacts (00:21:26)  

Example Target Companies (00:22:06)  

Pricing Strategy for B2B SaaS (00:22:48)  

Justifying Tiered Pricing (00:24:14)  

Timeline to Reach 1 Million IRR (00:25:09)  

Step-by-Step Action Plan (00:26:33)  

Closing and Reflections (00:28:03)  

Final Thoughts and Outro (00:36:07)