The email you meant to answer. The meeting that needs preparation. The subscription that renews before you remember to cancel it. For entrepreneurs, these small responsibilities can consume a surprising amount of the workday.
Using AI as a personal assistant can help bring that work under control. Across two Startup Club conversations—The Complete Entrepreneur with Colin C. Campbell and Michael Gilmour, and Start, Scale, Exit, Repeat with Colin and Michele Van Tilborg—founders shared how they are putting AI to work in their businesses and daily lives.
Their examples went well beyond asking a chatbot questions. They described morning briefings, project trackers, document preparation, and reminders that help keep commitments from slipping. They also disagreed about how much independence an assistant should have, especially when it starts communicating on someone else’s behalf.
“You Can’t Outsource the Entrepreneur”
Colin C. Campbell
Start With the Work That Keeps Piling Up
Michael’s move toward a personal AI assistant began somewhere unexpected: an anniversary dinner. Faced with an unfamiliar menu, he photographed it and asked ChatGPT to explain the dishes. That simple exchange made him reconsider the boundaries he had placed around AI. Why reserve it for designated work sessions when it could help with everyday problems?
He began developing an assistant that provided morning briefings, surfaced important messages, and helped him track unfinished work. In one instance, it flagged a mismatch between the date and day of the week in a meeting arrangement, giving him a chance to clarify before it became a scheduling problem.
Michele described a similar need. With too many emails to manage comfortably, she asked her assistant to review her inbox each morning at 8 a.m. and maintain a Google Sheet of tasks, updates, and replies she owed.
She was still refining the process. A task summary was less useful when she could not tell where it came from, so she asked for the original email’s subject line as well. That detail matters: an assistant should make the next action easier, including finding the message behind a recommendation.
Give Your Assistant Context and Clear Instructions
A useful assistant needs to understand the person and business it supports. During the second conversation, participant Elizabeth emphasized a step many entrepreneurs skip: explaining their business, communication style, and expectations before asking AI to produce work for them.
Colin shared his own preference for vendor communication: “nice but firm.” He also described providing his writing as a reference so that AI could help edit without replacing his voice. Michael takes a similar approach with difficult emails, supplying his main points and reviewing the resulting draft from beginning to end.
For an entrepreneur getting started, that context might include current priorities, recurring responsibilities, examples of well-written emails, and a clear description of what requires approval. Keep it relevant to the assignment. An assistant preparing a meeting brief needs the agenda and background, rather than every document the business has ever produced.
Elizabeth also described organizing work into separate projects for clients, businesses, and books. Keeping the relevant background together gives each assignment a clearer starting point and makes the material easier to manage.
Use AI to Make Scattered Information Useful
Some of the most valuable examples involved gathering information that already existed but was difficult to work through.
Colin described using AI to organize emails and documents related to an insurance claim after a hurricane damaged a beach house. He worked through the material with the assistant to prepare his argument and supporting information. Michael used his appointment history to identify meetings relevant to a government grant application and organize them into a usable format.
These tasks can be especially draining for founders: the information is available, but finding it, sorting it, and turning it into something useful takes time. AI can help with that preparation while the entrepreneur checks the underlying records and decides what to submit.
Recurring expenses provided another practical example. Colin said an assistant reviewing his emails identified an upcoming newspaper subscription renewal. After contacting the provider, he reported saving about $300. Michele described using payment notification emails to build a running spending tracker. The value in both cases came from making routine information visible enough to act on.
Decide When Your AI Assistant Needs Approval
The liveliest disagreement across the conversations concerned outgoing messages. Colin welcomed an assistant that took initiative, although he acknowledged that messages had gone out with mistakes. Michele wanted drafts she could approve before they reached a business contact. Her relationships were too important to leave the wording and interpretation entirely to an automated system.
Other participants described ways to retain that control. Ryan’s custom assistant could read email and prepare drafts, but could not send them. John described an assistant that noticed neglected client relationships and suggested follow-ups for him to authorize.
Michael and cybersecurity participant Rene also raised questions about the information an assistant could access. Their discussion highlighted a decision that belongs alongside the task itself: which messages, files, and accounts does this particular job require?
Set those boundaries in the tool’s available permissions as well as its written instructions. Reviewing a draft, approving a calendar change, and authorizing a purchase are different responsibilities. Treat them as separate decisions when setting up an assistant.
Build One Reliable Routine Before Adding More
The conversations offered plenty of ambitious possibilities, but a useful starting point is a routine you can evaluate. Choose one recurring task: a morning inbox summary, a list of overdue replies, or a briefing for tomorrow’s meetings. Explain what the output should contain, check it against the source material, and refine the instructions when something is missing.
Measure whether it helps. Are you spending less time searching your inbox? Are fewer follow-ups getting lost? Does the briefing prepare you to make a decision? Those results tell you more than the number of tools you have connected.
As Colin put it, “You can never outsource the entrepreneur.” An AI personal assistant can take on preparation and help maintain momentum. Your experience, relationships, and judgment determine what happens next.
Explore more conversations about entrepreneurship, AI, and business growth at Startup Club, and join the community to share what is working in your business.