Hot Seats on Pitch Decks, Deal Structures and Due Diligence
Capital Raising Hot Seats: Pitch Decks, Structures & Investor Relations with Richard C. Wilson
Sponsors, founders and fund managers who are preparing a pitch deck, shaping a deal structure or getting ready for investor due diligence.
What to take from this talk
- Lead with a one-pager timeline. A one-liner on top and a company timeline below helps when a platform looks new but the team has a long record. Richard says whole meetings with a family can be spent walking through the timeline.
- Show alignment with your own capital. Richard describes an example where the sponsor's own capital is placed alongside the investor's to show alignment. He compares it to ideas from the hedge fund world. He says it can communicate confidence and aligned incentives. Structures like this are worth discussing with a securities attorney.
- Diligence depth follows check size. Richard says raising $20 million often brings far more scrutiny than $200,000 or $2 million. Early stage and construction risk can also raise the bar. For loans, investors may check title, other liens and executive backgrounds.
- Build trust through niche knowledge. Richard describes three shortcuts: investors who know the niche, investors who know the geography, and investors who already trust you. A database of 100 people who sold similar businesses can mean you do not have to explain the industry.
- Lead cold outreach with value. Richard says the best first contact is a resource, an introduction or a deal structure, not a pitch. Short, clear messages with an agenda work best. He says the aim is face-to-face relationships, not email volume.
The short version
A one-pager with a timeline helps a sponsor with a long track record present a new platform as credible. Richard C. Wilson shows an example for a roofing company, with the one-liner at the top and the company history at the bottom. He notes that busy contacts rarely have time for a 22-page deck. He also suggests focusing about 80% of capital raising on cities where projects exist, so investors can visit.
The other hot seats cover bridge loan due diligence, a beef platform raising a royalty participation note, and a seed-stage health technology company with no ARR. Richard explains that larger checks often bring deeper diligence. He also describes cold outreach that leads with value and one example of how some sponsors think about aligning their own money with investors. The session ends with membership and event details.
Facts and figures
- Richard says the best capital raisers he knows often contact 180 to 300 prospects to find 8 to 15 investors.
- One hot seat discussed an illustrative structure with interest for a period, followed by a share of revenues until a target return multiple was reached. Terms like these vary widely and are not a recommendation.
- The risk capital example used illustrative numbers to show how a small amount of capital can sit alongside a much larger amount. It is a discussion example only.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Capital Raising Hot Seats: Pitch Decks, Structures & Investor Relations with 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 deal structure terms, offering documents and investor eligibility rules. Do not use AI to write your own legal agreements.
Quotes from the session
"If you both take a 10% haircut, you both get hurt by 10%. If you both get a 10% gain, you're both getting a 10% gain."
"The best capital raisers on planet earth, who have raised $10 billion or $40 billion, typically reach out to 180 to 300 prospects to find the 15 who invest, or the eight that invest."
"Education is how you build trust. You know, adding value and education."
- 1Investor asks questions by email
- 2Call or Zoom to review answers
- 3Access to data room
- 4Meet founder in person
- 5Tour asset and check title
Related questions
- What is an investor teaser and what goes in it?An investor teaser is a one-page, one-sided PDF that tells an investor what your deal is and why it is compelling in two or three ways.
- How long should an investor pitch deck be?Keep your investor pitch deck to about 10 to 19 pages.
- What financial slides should a fund manager's deck include?A fund manager's deck should show the numbers an investor tests first.
Questions about this video
What happens after a family office likes a pitch deck?
Richard says investors usually ask questions by email, then hold a call. They may then request a data room, want to meet the founder in person or tour the property. For loans they may also check title and run background checks on executives.
How can a new platform look credible when the team has a long track record?
Richard suggests a one-liner and a timeline on a one-pager. He also suggests hosting investors at the actual project and showing the site in a simple, unpolished video.
What should someone do when investors want ARR and the product is brand new?
Richard suggests building credibility with specialists who already know the space, such as local doctors in a health technology case. He also suggests meeting them in person and targeting local investors with exits in that industry.
Put this into practice with the data room checklist. See all pitch decks resources.
