Doug GPT

Overview

This is a sparring partner for deal work, which Jannis describes as a time saver that compresses 30 minutes to 5 minutes before a call with founders.

It’s a Custom GPT working with web search and a GPT-bound data lake.

Access

ChatGPT ownership

• Can edit (essentially admin): Milos, Jannis, Vincent
• Can give admin: Milos, Jannis, Vincent
• Can view: IM (added one-by-one)

A copy of the context files included

This is kept for backup and transparency reasons only. No automated ingestion is possible. Access on SharePoint is available in the Doug GPT context folder.

Link to the custom GPT settings

Even admins can’t access this via URL. It’s a GUI multi-step:

• https://chatgpt.com
• sidebar: GPTs / Explore GPTs
• top right button: My GPTs
• Find the existing GPT in the list and hit ‘edit’

Common Tasks

Upload files

Files for CustomGPT knowledge are added manually via GUI.

Weekly

There was initially an ask to include a weekly newsletter in the context, but there is no API endpoint with ChatGPT for this, so it was done manually. This task has been abandoned in favor of higher-priority work since there were no further asks or context complaints from IM, other than ideas by Jannis and Vincent.

Yearly

E.g. a Sequoia annual report for 2025 might need an update down the line.

Give read access to new hires

When a new person joins the IM, they need to be added to the list of individuals with access.

Troubleshooting

Version history attempt vs. shared admin

Vincent was added as an admin at his own request and was asked explicitly three times to let the automation team know once he was done editing. He replied once that he would be on it, and that is where the communication ends.

The idea was to communicate actively to ensure backups are made by the automation team of prompts and settings at discreet increments.

Context limitations

As of November 2025, a per-file size limit was 512 MB and there was a hard cap of about 25 files per GPT. This may have changed since.