When someone agreed to try Stripe, Patrick and John Collison asked for their laptop and helped them get set up then and there. That's how Paul Graham described the brothers' approach in his July 2013 essay on early customer recruitment. At Y Combinator, he wrote, they called it the Collison installation.
The account describes what the founders did after a person said yes. It doesn't tell us how many people stayed with Stripe or how much of the company's growth came from those sessions. What it gives a founder is a much smaller idea to try: watch what happens between agreement and first use.
Patrick traced the payments problem back to Auctomatic in a 2024 Stripe Sessions conversation. Building that earlier business had exposed him to the trouble of accepting payments online, both through his own experience and through what others told him. Hearing about the problem helped identify what to build. Sitting with somebody trying the product can answer a different question: can they actually get it working?
Watch the first job, not the tour
Suppose you sell software that turns a wholesaler's order spreadsheet into a pick list for the warehouse. A buyer says yes. Ask them to bring a sample spreadsheet they are allowed to share, then watch them try to produce a usable list. Let the buyer drive. If a step needs a password or access to a live account, stop the screen share while they handle it.
Say the import fails because the sheet has two header rows. You can delete the extra row. Write down who did it. If you clean the sheet for the buyer and record the session as a success, you won't know whether the next person can get past the same error alone.
Count the assisted run separately. The buyer got a list, but only after you prepared a file the software could read. That's different from finishing alone.
Run the next setup without coaching
After a few sessions, look for a delay you can explain in plain language. Perhaps customers understand the product but keep bringing files it rejects. Start with that error. Fix the message or let the importer accept the extra row. If each delay instead comes from a different approval requirement at the customer's company, another import feature may do little.
Try the revised setup with a new customer in the same kind of business. Send the usual instructions. Give them room. If they get stuck, record where they stopped before you offer help. If they finish, open the list together. Could someone on the warehouse floor use it as-is? Getting to the last screen is a poor substitute for seeing the pick list they came for.