How Richard C. Wilson Uses AI in Deal Work

At a Family Office Club event, Richard C. Wilson shares practical ways to use communication and AI tools in investor relations and deal work.

Richard C. Wilson closes a Family Office Club session with a practical tour of communication habits and AI tools for investor relations, deal screening and company knowledge. He moves from email follow-up and asynchronous messages to screening calls and custom GPTs, with examples for teams working with investors and family offices.

In this video: Richard C. Wilson (Founder of Family Office Club)

What they said

1. Richard on email follow-up. Richard says he uses email snooze reminders to keep follow-ups visible. He says it took 14 emails for Mark Cuban to reply to his interview questions, with follow-ups every 6 weeks or 8 weeks. (at 7:56)
2. Richard on asynchronous communication. Richard recommends messages and audio notes for conversations that don't need a meeting. He says they let him think before replying and preserve tone, while helping people get three times as much done. (at 10:12)
3. Richard on qualifying calls. Richard says he asks people pitching him deals questions before scheduling a call, then uses their answers to shape an agenda. He says this can make a call last 8 to 10 minutes and keep it focused on relevant topics. (at 12:30)
4. Richard on Dewey's first review. Richard describes Dewey as a custom GPT that reviews pitch decks and flags risks or questions for further diligence. In his view, it can supplement review, but it doesn't replace meeting a person or bringing in qualified professionals. (at 19:25)
5. Richard on family knowledge tools. Richard describes a custom GPT built from public billionaire videos and interview transcripts, with plans to add infographic and book summaries. He suggests a similar tool could let future generations ask questions about a family member's business experience and values. (at 21:17)

In their words

"You can hire some Uber nerd to dial in your Perplexity or a custom GPT or Notebook LLM or whatever it is you want to do."

"More feedback before you just let them loose or before you know it, they're spending 40 hours on something that's completely off base from what you actually wanted them to be doing."

Why it matters if you are building or preserving great wealth

Richard says an AI used by many CEOs can average their ideas. He says a founder who follows that baseline won't reach the top 0.1%.