What would help your customers more: another round of faster AI output, or a better way to see what you're building?

Josh Colter, the majority owner of Cardboard, has put a lot of thought into that question. He bought the company with a bet on AI and has been combining story maps with detailed instructions so he can see the big picture while the models work through the details.

His comparison comes from the Wright brothers. He says "they thought about control first." A bigger engine is useful once you can steer. Josh applies that idea to building software: make the work visible, understand the customer behavior you're trying to change, and keep releases small enough to inspect.

We talk about the difference between having AI drive and learning to operate it yourself, why a long specification can hide something a human needs to see, and how Josh planned and shipped dark mode in three days after finding years of requests from users of a competing product.

Useful questions from the conversation

Can you see the work clearly enough to tell where it's going?

Can the people building it understand the plan as readily as the AI can?

What customer request are you trying to meet, and how will you check the result?

Chapters

00:00 Control before thrust

00:45 Show intro

00:53 Meet Josh Colter

01:26 Buying Cardboard and betting on AI

02:46 Chauffeurs and airmen

08:47 Why a bigger engine needs control

11:05 Make the work visible

15:20 Story maps, specifications and human understanding

20:32 Planning and shipping dark mode

25:26 Checking what you've actually built

26:35 Where to find Josh and Cardboard