Hawaii Family Office Retreat: AI Tools and Pitch Package Tips
Hawaii Family Office Retreat: AI, Investors & Capital Raising Strategies | Richard C. Wilson
Founders, capital raisers and investors who want to understand how family offices think and how AI can speed up pitching and due diligence.
What this talk covers
Richard C. Wilson opens the Hawaii Family Office Retreat by saying the family office industry holds over 14 trillion dollars. He says that is bigger than private equity and venture capital combined. He describes family offices as founders who have had exits, and says the club's main value is learning from them, not finding an investor right away.
He then walks through AI tools built on transcripts from the club's events. They cover investor lists, due diligence reports, and deal structures. He also lays out a pitch package of a one-liner, a short founder video, a one-pager, a short deck, and a due diligence questionnaire. He ends by urging in-person meetings and full due diligence on everyone.
- 1One-sentence pitch
- 2One to three minute founder video
- 3One-page version of the deck
- 4Short deck of 10 to 15 pages
- 5Due diligence questionnaire
Five points worth keeping
- Family offices are successful founders. Richard C. Wilson describes family offices as entrepreneurs who have cash flowed or exited a business for seven, eight or nine figures or more. He says the best use of the room is learning from them. Pressuring someone, he adds, usually makes them back off.
- Meet in person for big decisions. Richard says people want to meet face to face when the decision matters, such as investing a quarter of a million dollars or more. He cites Robert's claim that people are far more likely to invest or negotiate a deal if they meet in person. AI can make almost anything look good, so he says to walk the property and shake the hand.
- AI supports deal work, it does not replace it. He cites studies he attributes to BCG, Harvard and MIT showing more work done with fewer mistakes. He compares it to a chess player working with AI. He still says to read every word of anything you invest in.
- Build a structured pitch package. Richard says investors like a one-sentence pitch, a one to three minute founder video, and a one-page version of the deck. A short deck of 10 to 15 pages should follow, not 40 to 70. He says many investors would rather watch 45 seconds of the founder than start with a 40-page deck.
- Offer a due diligence questionnaire. He suggests a questionnaire with the top 30 questions investors should ask and the answers to them. An AI tool can draft it from a pitch deck or PPM. He says to check the draft word for word and notes that many sponsors also ask their own advisors to look over materials like this.
Said on the call
"Family offices are just super founders, like super entrepreneurs who have learned how to cash flow or have an exit for seven, eight or nine figures or more."
"You should still read every word of anything that you're going to invest in yourself. It's not to replace that."
"Most investors would prefer to first watch 45 seconds of a founder explaining what they're up to than look at a 40-page pitch deck."
Key facts
- Richard C. Richard says the family office industry is over 14 trillion dollars, larger than private equity and venture capital combined.
- The investor pipeline tool searches 22,000 investor profiles and returns the top 50 matches near the user.
- The structuring tool is trained on a thousand deal structures and suggests 10 deal structures at a time.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Hawaii Family Office Retreat: AI, Investors & Capital Raising Strategies | Richard C. Wilson. 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 offering document review, deal structure options and investor communications. Do not use AI to write your own legal agreements.
Related questions
- How do I use AI to summarize investor meeting notes?Start with a transcript of the meeting, give it to an AI tool with a specific request, and say what format you want back.
- How do I use AI to write investor update newsletters?Give the AI your real source material, such as deal notes, closings and milestones, and ask it for a first draft in your own voice.
- Can AI automate investor follow-up sequences?Yes, AI can automate much of the routine work in investor follow-up, like scheduled emails, reminders and tracking who replied.
Questions about this video
How big is the family office industry according to the talk?
Richard C. Richard says there is over 14 trillion dollars in the family office industry. He says that is bigger than private equity and venture capital combined, and that it is still growing.
What should a founder include in a pitch package?
He lists a one-sentence pitch, a one to three minute founder video, a one-page version of the deck, and a 10 to 15 page pitch deck. He adds a due diligence questionnaire with the top 30 questions and answers.
Can AI replace reading deal documents?
No. Richard says AI can analyze a long document such as a 140 page PPM and flag missing items and red flags. He still says to read every word yourself and not to trust AI blindly.
Put this into practice with the pitch deck grader. See all ai for capital raising resources.
