How to use AI as your founder assistant, and what NOT to ask itby Derek Lidow As we said last week, AI is a decent assistant but it is not a good partner or mentor. For the next two newsletters we will focus on where and AI can help aspiring and practicing entrepreneurs without causing more trouble than they are worth. This week we will focus on where AI can be a potent assistant and next week we will focus on where and how it can give good specific advice. Many people are disappointed with their AI experiences and there are many ways AI can and will disappoint. Last week’s discussion of the danger of using AI’s startup advice is an example of AI not having the training to replace a human who is trained and experienced in providing individualized, multidimensional analysis.
AIs are trained with generic data and by humans with specific types of expertise and experiences, and if your experience is very different from the experience of the trainers, its advice can be inappropriate. A second way that AI disappoints, is that if you ask or prompt it in a naive manner, it can give you a disjointed or nonsensical answer that may include hallucinations or made-up facts based on pretend expertise. We use AI as the equivalent of an assistant or intern on a daily basis and we suggest you do, too. We use AI in the private mode so our prompts and the answers we receive are not captured by the parent company (you can select this mode of operation in your settings). As with any assistant or intern, you do need to accept that they must learn how to work with you and what you expect, so you will always want to review their work to see if the task was understood and accomplished to your satisfaction. For example, we rely upon AI to brief us on how competitors are doing things we are also interested in doing. We also ask for briefings on organizations we are thinking of doing business with or that we consider as role models. We recommend all founders routinely study how other organizations do things particularly well. It is particularly valuable to do this before you meet with someone you want to ask for help for the first time. It makes for a more productive meeting and it greatly increases chances the meeting will produce a tangible result. AI can be very effective at producing very useful and insightful briefing documents. If we want a really deep briefing, we will ask both Claude and ChatGPT and there will always be bits of information we learn from one and not the other. This is a prompt we used recently to ask for a briefing, which AI did in 7 minutes that would have taken an intern two days. We prompted: I am the founder of an organization that provides aspiring entrepreneurs with on-line advice and coaching on how to be a successful entrepreneur. I would like a briefing on the XYZ NGO as we will meet with them to discuss ways we might collaborate. I would like to understand their mission, organization, funding sources, business model and all the data and comments that indicate the impact and success of their initiatives. Cite your sources. Do not spend time recommending how we could work together.
AI produced a 5 page briefing documented that included everything we asked for. All the sources of information it used were useful to know and not made up. We followed up asking AI to give us a list of and other NGOs that provided similar services to XYZ in other countries, which resulted in us asking for an in depth briefing on an organization we were not familiar with. We find prompting is important. Good prompting is a matter of explaining in plain language what you want AI to do for you as if AI were an educated but inexperienced intern showing up for their first day. If you want AI to follow certain steps or instructions in getting you what you want, then explain those as well. Do not assume AI is trained to think the way that you do. An important command to include with your prompt is to ask for the AI to give you a link to every fact it used to brief you. If the quoted fact seems important, then you will want to check to make sure it is correct. You can always ask AI to dig deeper or present their analysis differently. Rarely are you “one and done” with a single prompt. There are always things you’ll want done differently or parts of the presentation that will make you want to know more. If you do not know how to do something, like finding and filling out application forms, it is very good at finding the form and then explaining inputs you might not understand. When using the free version of ChatGPT specifically ask to use ChatGPT 5.2 thinking, otherwise it often will use a lightweight model that is designed to be fast but which takes shortcuts, frequently resulting in superficial answers, misunderstandings or hallucinations. As a final note for this week, we use AI to edit what we write. We hate looking for typos and checking grammar, so we love our AI editors. But we definitely do not use AI to draft correspondence or any of our general communications. We find AI drafted emails and internal communications are impersonal and often seem insincere. Anything that you want to represent “you” as a person needs to come from you. This is another reason we do not ask AI to create any content for our “The Entrepreneurs” platform, besides it being a poor entrepreneurship advisor or coach. Next week we will describe how to use AI tools to analyze and present information. With gratitude, Derek and Ben P.S. If you like what we’re doing, please consider recommending this newsletter to another person you think would benefit from us. It really helps us build out our free content platform.
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