How can I use AI to practice my investor pitch?
Short answer
Use AI to practice in three passes. First, score your pitch deck and fix what it flags. Second, tighten your pitch into a single sentence. Third, have AI write the 30 questions an investor should ask, then answer them out loud until the answers feel natural. At Family Office Club we built tools for each pass. Many sponsors talk to a securities attorney about their claims.
Score the deck before an investor does
The fastest first pass is a score. In our webinar on 10 AI tools, I ran a pitch deck through our Pitch Deck Success Score. It checks 25 criteria and gave my deck 68 out of 100.
It told me there were not enough team bios. It said there was no funding ask. It also flagged that there was no one pager or website. Then it listed what to fix first. A lot of people are missing a one pager or a website for their offering. You can fix the gaps, run the deck again and watch the score move.
This clip shows the pitch deck score and the seven one-liners the tool produced from an attached deck.
Summary and key takeaways from this video
Practice saying it in one sentence
Next, work on your one-liner. I get about a thousand emails a day, according to my email meter tool. I only get two to eight voicemails a day. That is 146 times more emails than voicemails. If you do not hook someone in the first line of an email or the first sentence of a voicemail, you are in trouble.
I attached my pitch deck and asked the tool for seven one-liners to consider. Pick one, then say it out loud. If you cannot say it concisely and with conviction, keep editing. You can use the final version on the front page of your deck, the top of your one pager, your website, your emails and your voicemails. You can also use it when you introduce yourself in a coffee line at a conference.
Rehearse the questions investors will ask
The part most people skip is the question and answer round. In my experience investors rarely just nod. I tell our members to have 30 questions and 30 answers ready. AI can build that list for you.
"The way I think about Clara is like a hyper-specialized pitch architect."
In our live forum I explained how this works. You upload your pitch deck, your webinar or a long email where you answered an investor. Then you ask Clara what the 30 dialed in questions are that an investor should ask. You also ask her to write all 30 answers from your own materials. Weak or missing answers show you where your materials are thin.
Then do the part the tool cannot do for you. Read each question and answer it out loud without looking. Clara also has a voice mode, so you can brainstorm by talking. If you do not know how to use a tool, you can literally tell it so and ask what it is good for.
Here I walk through how Clara rates a deck, writes a one-liner and builds the 30 questions and 30 answers.
Summary and key takeaways from this video
Match the practice to the room
Rehearsing is easier when you know who is listening. In my investor demographics module I explain that, in my experience, deals often close faster when investors trust the team, know the industry or are local to the opportunity. So before each practice round, ask which of those you are trying to build.
This clip explains the trust curve and why knowing your investor type changes what you should emphasize.
Summary and key takeaways from this video
If your investors do not know the industry, spend your practice time teaching it. If they do not know you, practice your background and track record. AI can help you draft and rehearse. Many sponsors also talk to a securities attorney about their materials and claims before pitching real investors.
From the Family Office Club stage
One thing I would add is that you do not have to type everything. In the tool I use, you can go into talk mode, record and dictate, and upload up to 15 files, such as your pitch deck and a webinar you gave. Then you can ask it to act like an investor and grill you. Practicing out loud against that kind of pressure shows you which answers are shaky before a real investor does. Treat it as a rehearsal partner, not a replacement for a live run through with a colleague.
"Through a tool like this, you can go into talk mode, you can record and dictate something, you can upload 15 files, your pitch deck, a webinar you did, you can get feedback, you can practice your pitch on this tool and have it grill you and act like an investor."
Facts and figures
- In the webinar demo, the Pitch Deck Success Score rated Richard's sample deck 68 out of 100 across 25 criteria.
- Richard receives about a thousand emails a day but only two to eight voicemails, roughly 146 times more emails than voicemails.
- Richard recommends having 30 questions and 30 answers ready for investors, and Clara can draft both from your uploaded materials.
Sources
From Richard C. Wilson's Centimillionaire Strategies YouTube channel: Webinar: Demonstration of 10 Artificial Intelligence Tools for Capital Raisers & Investors, Family Office Live Forum: Capital Raising, AI Tools & Investor Feedback (with Richard C. Wilson), Investor Demographic Target | Ep 2. 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 pitch material claims, investor communication rules and offering documents. Do not use AI to write your own legal agreements.
What to do next
- 1Run your current pitch deck through a scoring tool and fix the first items it flags.
- 2Ask AI for seven one-liners and pick the one you can say with conviction.
- 3Upload your deck and have AI write 30 investor questions with 30 answers.
- 4Answer each question out loud, then fix any answer that feels weak.
- 5Many sponsors talk to a securities attorney about their materials before pitching real investors.
More questions on this
Can AI replace a live practice session with a real person?
No. I use AI to prepare materials and spot gaps. You still need to say the pitch out loud and talk to real investors.
What should I fix first after my deck gets scored?
Start with whatever the tool lists first. In my example the gaps were team bios, a funding ask and a one pager or website.
Do I need a pitch deck before I start practicing?
It helps, because the tools can read it. You can still practice your one-liner and your answers to investor questions without one.
Related questions
- Will AI replace placement agents and capital raisers?Probably not fully.
- 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 ChatGPT help me write an investor email?Yes, an AI tool can help you draft and tighten an investor email.
- How can AI speed up my investor due diligence preparation?Give AI your pitch deck and any emails where you already answered investor questions.
Work through it with the one-liner builder. See all ai for capital raising resources.