Mark Cuban replied on the 14th email
Richard C. Wilson emailed Mark Cuban 14 times before Cuban answered his interview questions. In Richard's early count, 17 of the first 22 billionaire interviews came from cold emails. He uses the story to make a point about doing the tedious list work most people skip.
Build the list, then work it
Richard's team built a database of billionaires. He reached out to every one he could find on Instagram, Facebook or email, many of them more than once. Cuban was one of those cold emails.
The same method for deals
Richard gave the same idea to a member buying accounting firms. List the 100 firms in the area with each owner's contact details and social profiles. Then work that list over and over. Competitors may cover several cities, so a local buyer who does the dull work can meet every owner.
Why the replies come
Richard says owning Billionaires.com is a big part of why people like Cuban and Michael Saylor's team reply at all. The name gives a cold email a reason to be read.
In Richard's words
"I had to email Mark Cuban 14 times till he answered my questions." (Richard C. Wilson, Billionaire Insights talk)
"But out of the 22 billionaires, 17 of them were cold emailed" (Billionaire Insights talk)
"you just work that list tirelessly and do the tedious work that nobody else will ever do." (2026 event, about 2:36:19)
"It's the reason why Michael Saylor would reply to your email, or Mark Cuban replied to my cold email, is because I own Billionaires.com." (April 2026 FOC event)
How to use this
- Count your follow-ups. Most people stop after two or three, and Richard's reply came on number 14.
- Build the full list of targets in your niche, with every channel to reach each one.
- Give each message a reason to be read, such as a known platform, a clear ask or a credible name.
- Use the same list method for buying businesses, not only for outreach.
Questions and answers
How many times did Richard C. Wilson email Mark Cuban?
14 times. Cuban answered the interview questions after the 14th email.
Were most Billionaires.com interviews cold outreach?
In Richard's early count, 17 of the first 22 billionaire interviews came from cold emails. The rest came from referrals.
How does this apply to buying a business?
Richard suggests listing every target company in your area, with each owner's contact details, and working that list persistently.