Due diligence
The Wiltbank study found that investors who spent more than 20 hours of diligence per deal averaged nearly 6X, versus 1.1X for those under 20 hours. Investors above 40 hours saw returns greater than 7X. The videos here cover the checklist behind those numbers, including five-year pro formas with cash flow to the next financing round, breakeven timing and a profitability forecast. They also include a case where a fund put in $5 million 13 months before a company went bankrupt.
Family Office Club built the Dewey AI due diligence tool, which has produced over 2,000 reports. Richard C. Wilson equates that to nine full-time year-round employees. Dewey was trained on 18 years of club data, 1500 investor talks and the top 150 white papers on due diligence. Other pages cover reference checks, a master questionnaire for multi-family offices and a guide to preparing a data room for investor due diligence.
24 videos, 1 guide on this topic.
Guides
- How to Prepare a Data Room for Investor Due DiligenceMost capital raisers wait until an investor asks for files.
Videos with summaries and takeaways
- Technology Investor Panel: How Angels Screen Tech DealsBand of Angels looks at about 50 unsolicited deals a month.
- Billionaire Strategies for Success: Details, People and Due DiligenceIra, a former Chase workout banker, spent 15 years buying companies for a billionaire family.
- Deep Due Diligence: Tools, Teams and Case Studies with MarcMarc sees about 400 deals a year and invests personally in four.
- Evaluating Deals and Performing Due Diligence: A Full ChecklistIn the Wiltbank study cited in this talk, angel investors who spent more than 20 hours on due diligence per deal averaged nearly 6X returns.
- AI for Investor Due Diligence, Deal Structuring and Capital RaisingRichard C.
- Dewey AI Due Diligence Tool: Vet and Screen Deals FastDewey is an AI due diligence adviser that Richard C.
- 10 Small Details That Matter in Due DiligenceThe speaker is 72 and belongs to a group of more than 50 accredited investors who share deal flow and run joint due diligence, then invest separately.
- Due Diligence Time Savers for Private InvestorsScreening deals by email before any call is the main time saver Richard C.
- Fine Art Lending and Collateralized Debt Investor MandateThe guest runs a family office investment boutique that was started thirty years ago after leaving Wall Street.
- How to Prepare For and Survive Investor Due DiligenceSlow replies are one of the quickest ways to lose a sophisticated investor, according to Richard C.
- How to Do Due Diligence on an Investor Conference or ClubRichard C.
- Close More Deals With a Master Due Diligence QuestionnaireA master due diligence questionnaire, or DDQ, is one document that answers the questions investors ask most often.
- Closing Deals with Celebrities and Pro Athletes: Metta World PeaceMetta, a former NBA player with a 17 year career, describes how he moved into business through his philanthropy work in Los Angeles.
- How a Family Office Screens Deals and Builds Investor TrustSahil's family office screens deals by checking one thing first: the stability of the partner bringing the deal.
- Pro Athlete to Investor: Real Estate, Crypto and a Costly MistakeJohn played three years for the Cardinals after college at Penn State.
- Due Diligence and Investment Strategy: Family Office Club PanelA 156 question checklist sits at the center of this Family Office Club panel, where family office and fund representatives compared how they vet deals.
- Investor Mandate Interview: Consumer Products, Fintech and BiotechA 24-hour cool down rule is the main habit Steve shares in this investor mandate interview with Richard C.
- How Focused Due Diligence Helps You Win Better Deal TermsRichard C.
- Florida Angel Investor Mandate Interview with ThomasThomas leads the Palm Beach chapter of Curitzu, an angel investor forum with 54 chapters around the country.
- Investment Horror Stories: Due Diligence and Fundraising MistakesOne angel investor describes a startup whose founder skipped a hot fundraising market, hoping for a higher valuation later.
- Private Investor Due Diligence Mini-Series: OverviewRichard C.
- Shortcuts to Vet CEOs and Investment ProfessionalsA smile, a bad meal and a drink or two can tell an investor more about a CEO than a ratio can.
- Where Real Estate Is Headed in 2025, With Joe of Keller WilliamsJoe, co-founder of Keller Williams, lists seven local influences he checks on any piece of real estate.
- What Investors Want to See in a Pitch Deck: A Panel DiscussionA panel of investors each name what they want to see in a pitch deck.
Questions answered
- How do I close a funding round?I close a funding round by focusing on investors who fit the opportunity and moving each interested prospect through clear, consistent follow-up.
- What documents do investors request during due diligence?Prepare a clear, organized package covering your operations, investments, compensation, team, and track record.
- How do I raise capital for my business?I raise capital by building a repeatable system for attracting the right investors, establishing credibility, and developing relationships before asking for money.
- How do I raise money with no track record?I would raise money without a track record by focusing on credibility, relationships, and evidence of my ability to execute.
Tools for this topic
Common questions
What did the Wiltbank study find about diligence hours?
Investors who spent more than 20 hours of diligence per deal averaged nearly 6X, versus 1.1X for those under 20 hours. Those who spent more than 40 hours saw returns greater than 7X.
How many reference checks does Richard suggest documenting?
Richard suggests documenting seven reference checks for each main partner or the top CEO.
What does the Dewey due diligence tool do?
Dewey is an AI tool trained on 18 years of club data, 1500 investor talks and the top 150 white papers on due diligence. Its forensic accountant mode reviews the last 3 years of financials plus year to date, looking at ratios, trends and missing line items.


