#354

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)