AI Tools, Thought Leadership and Clear Messaging for Raising Capital
Richard C. Wilson | Family Office Club Workshop- AI, Thought Leadership & Capital Raising Strategies
Founders, fund managers and investors who want practical AI and communication habits for raising capital and screening deals.
The 5 big lessons
- Make what you do obvious. Richard says too many people make it hard to understand their business. Abner's Harlem Real Estate Holdings name and website brought in Harlem deals. An email signature like "ABC Capital" tells a new contact nothing.
- Use text and live chat. Richard says text messages often get opened at much higher rates than email. He cited about 90% for texts and 8% or less for emails, which are his figures and will vary. He also recommends live chat for websites with a couple hundred visits a day. Text message marketing and live chat are separate tools, and many people talk to an attorney about messaging rules before starting outreach.
- Let email snooze handle follow up. After sending an important email, Richard snoozes it to return in a set number of days. It took 14 emails to get Mark Cuban to reply to interview questions. Over 12 years, more than 170 emails of negotiation helped win billionaires.com.
- Screen deals before any call. Richard asks for an agenda and written questions first, then gets on a call. He uses a due diligence GPT to suggest more questions. Calls then run 8 to 10 minutes. He says the tool adds to, and does not replace, meeting people or getting professional help.
- Build custom GPTs from your own material. His team fed 986 billionaire YouTube videos and 42 interviews into a billionaire advisory tool. Richard says anyone can build a custom GPT in 15 to 30 minutes. He suggests starting with what your team or investors ask most often.
The short version
Chip Perkins, who Richard says has raised over $40 billion, called thought leadership the holy grail of raising capital, according to Richard C. Wilson. He ties that idea to a clear message about what you do. Abner describes renaming one LLC Harlem Real Estate Holdings, a local operator focused on New York City middle market renters. After the website went up, every deal in Harlem came to him.
Richard then walks through the tools his team uses. They include text message marketing, PhoneBurner, live chat, email snooze, Fixer.ai, Upwork, and custom GPTs for due diligence, billionaire research and one-liners. He says AI should add to human judgment and not replace it. Audience members close with comments on visiting properties, family incubators and website form outreach.
Facts and figures
- Fixer.ai drafts email replies for the user to review and send. Richard cited a stat of about 45% of drafts being sent without editing.
- Richard's team has hired over a hundred people on Upwork over 18 years. He asks for a fixed price and starts with a small test task.
- The Investor Nexus GPT draws on 1100 YouTube videos and 13 books Richard published.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Richard C. Wilson | Family Office Club Workshop- AI, Thought Leadership & Capital Raising Strategies. Quotes come from the video captions, lightly edited for readability. Figures are the speakers' own estimates and experience.
General education only. Not legal, tax or investment advice.
Talk to a securities attorney to explore options around text outreach rules, entity naming and deal screening. Do not use AI to write your own legal agreements.
In their words
"you will save hundreds of hours of your life if you do not get on the phone with people until you have at least halfway of an idea of what they do."
"you only have a couple seconds to get an investor's attention."
"billionaires do not find safety in following the herd."
- 1Ask for the call agenda
- 2Send written questions first
- 3Run the deck through a GPT
- 4Ask five to ten follow ups
- 5Hold a short focused call
Related questions
- How do I use AI to research family offices?Ask a tool like ChatGPT or Grok to run deep research on a specific person at a specific family office.
- How can AI help me find investor mandates and criteria?AI helps most with sorting, not sourcing.
- How do I use AI to build a fundraising financial model?Use AI as a fast assistant for drafting the structure, formulas and scenarios of your model, then check every number yourself.
Questions about this video
Why does Richard say in person contact matters for investor relations?
He says John calls investor relations a contact sport. John attends real estate closings in person and sources deals there from title agents, attorneys and counterparties. Richard says in person is 30, 50 or 100 times more effective.
How does PhoneBurner help with outreach calls?
Richard says it lets a user leave a scripted one-liner voicemail with one click and move to the next call. He says it can help a person make 100 calls a day instead of 20, 30 or 40. His team had just started testing it.
How did the audience's one-liner panels go?
Richard says seven investor panels rated submitted one-liners on a scale of 1 to 10. At the last event, only one person got a good rating. He says many people have no one-liner at all.
Put this into practice with the one-liner builder. See all ai for capital raising resources.


