Centimillionaire Strategies · Oct 17, 2026 · 25m · 19m saved
With Richard Wilson, Founder of Family Office Club
Family Office Club's sales team used a custom GPT 1,500 to 1,800 times a year, then used a sales-specific AI system hundreds of times a week, Richard Wilson, founder of Family Office Club, said in a keynote on Centimillionaire Strategies.
McKinsey research he cited puts general AI use at 88% of people. Richard puts the share of companies that build a dedicated AI system for every role at under 1%, and his talk was about closing that gap.
"If you use generic AI, and you just go to ChatGPT, you're going to get generic results." — Richard Wilson
Richard started the business in 2007 and has done 43 transactions for his own balance sheet, alongside the deals the club helps structure for family offices.
The full episode is covered here so you can skip it. 25 minutes of audio, 6 minutes of reading.
Here are the 6 lessons that matter.
Key Takeaways
One AI system per job function beats one shared chatbot login for a whole team
Richard compares a shared login to giving a carpenter, an electrician and a roofer one toolbox
Family Office Club's sales team used AI 5 to 10 times as often once it had a system built for sales
A software migration took 9 days with AI, against 9 months and $25,000 for a consultant the time before
Most companies need 7 to 12 role-specific AI systems, Richard estimates
Family offices would rather back someone they trust than someone promising bigger returns
One investor writing a seven- or eight-figure check is worth dozens or hundreds of smaller ones
1. 330 Events in 19 Years
Richard opened with the size of the event business. Family Office Club has run about 330 events over 19 years, and this one was its first in the Silicon Valley area. Its core cities remain Los Angeles, New York, Dallas and Fort Lauderdale.
Family Office Club is dropping one-day events for four three-day summits
"Next year we're doing zero one-day summits. We're just going to do four big super summits... each summit, 110 speakers on stage." — Richard Wilson
This session packed 27 speakers into a single day, against 12 to 15 in a normal format. October brings masterminds on deal structuring in all four core cities, and the annual Super Summit runs December 15 to 17 in Fort Lauderdale. At the last one, the club's mobile app alone recorded more than 1,000 meetings.
