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The investment meeting
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The investment meeting
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The investment meeting
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The investment meeting
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Steve Callahan · Managing partner, early-stage VC
An early-stage founder is presenting a venture for investment fit.
SteveSteve closes the deck and looks directly at the founder.
You have ten minutes. Start with the problem, not the product. Why does this company need to exist?
Independent clinics lose hours every week chasing patients after missed appointments. We automate personalized follow-up and let staff focus on care.
SteveThat sounds useful, but useful is not necessarily venture-scale. Who pays, how much, and what evidence says this is urgent?
The clinic pays $240 per month. We have six paying pilots, and four converted after a 30-day trial. Those clinics reduced unfilled cancellations by an average of 18%.
SteveSix clinics is early. What have you learned that would make the next fifty easier than the first six?
The buyer is the clinic manager, not the physician. Our strongest channel is practice-management consultants, and two have agreed to introduce us to their client groups.
SteveHe leans back and waits without offering a hint.
What breaks if a large scheduling platform ships this feature next quarter?
The reminder itself is easy to copy. Our advantage is the workflow data across channels and the response model tuned to each clinic. I still need to prove that advantage compounds.
Before we assess the pitch, what part of Steve’s questioning felt most difficult to answer?
The defensibility question. I knew the reminder feature could be copied, and I did not want to pretend otherwise.
You named that uncertainty directly. What evidence did you have, and what was still only a hypothesis?
The six paying pilots and the 18% reduction were evidence. The workflow data becoming a durable advantage was still a hypothesis.
Simulation Complete
The investment meeting
You stayed composed under pressure and treated uncertainty as something to examine rather than conceal. The next step is to make your evidence as precise as your vision.
You presented a clear operational problem, supported demand with early paid evidence, and responded candidly to the defensibility challenge. Your strongest moments converted broad claims into measurable facts. To strengthen the investment case, separate current evidence from planned validation earlier and quantify the economics of the acquisition channel.
✓ You answered the traction challenge with specific numbers: “six paying pilots” and “four converted after a 30-day trial.”
✓ You acknowledged uncertainty directly: “I still need to prove that advantage compounds.”
→ State the customer acquisition cost and expected payback period when describing the consultant channel.
→ Frame the requested round with an amount, runway, and milestones before being asked.
Distinguish evidence already observed from hypotheses the seed round is intended to test.
“Independent clinics lose hours every week chasing patients after missed appointments.”
“We have six paying pilots, and four converted after a 30-day trial.”
“The reminder itself is easy to copy… I still need to prove that advantage compounds.”
“I will send both by tomorrow… May I also include two customer references?”
Overall Score
87
The character remembers what was said, reacts emotionally, and never breaks role.
Radar comparison
Example class — The investment meeting
Participants
Which evidence changed the investor’s confidence, and which claims still need validation?
“Six pilots show interest, but I should not present them as repeatable revenue yet.”
“The conversion is promising; retention is what still needs proving.”
“I still need to prove that advantage compounds.”
“We know the buyer; the acquisition cost is still an assumption.”
“I can explain the channel, but I did not give a payback period.”
“The margin improves with scale, though I should have quantified it.”
“The feature can be copied; the workflow data is the bet.”
“Our moat is not the reminder itself, and I should say that earlier.”
Separate validated evidence from assumptions in the first two minutes.
State acquisition cost, gross margin, and payback period without prompting.
Answer defensibility questions with a testable claim, not a broad promise.
Everything the class did, ready to present in the next lesson.
Build once. Practice together. Learn individually.
Traditional classroom learning
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Everyone practices at once
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Not another AI tool — a different way to practice human skills.
You can prompt a chatbot to play a role. Here is what that does not give you.
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You control the learning experience — not the model.
Written against your rubric, quoting your student's own words.
Every point maps directly to an objective you defined.
It names what was said and why it mattered.
See personal reports, class patterns, and complete transcripts.
otherstanding is built by a team of entrepreneurs, academics, educators and experiential-learning specialists with more than 30 years of combined teaching experience. We spent years running roleplays with two volunteers at the front of the room while everyone else watched — so we built the tool that gives every student the conversation, and every educator the whole picture.
Built for universities, schools and organizations that have to answer for their students' data.
Same product, different conversation.
Universities & Colleges · Business Schools · Executive Education · Research labs
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Give a whole course the practice that usually fits two volunteers at the front of the room.
Example: A management student tells a team lead a deadline was missed and must separate facts from interpretation.
Turn frameworks into consequential conversations under pressure.
Example: Negotiate scope and price when a prospective client asks for a late concession.
Hold the scenario constant across participants and export what was said.
Example: Every participant faces the identical negotiation counterpart; transcripts are exported for coding.
Run the same practice conversation across cohorts and see where the group actually struggles.
Example: A new manager gives difficult feedback to a team member who pushes back.
Build once, share a link, and coach a group without being in every conversation.
Example: A coaching client who is ambivalent about a difficult change.
Used for negotiation, sales, leadership, feedback, customer success, healthcare, law and mediation, psychology and coaching — or any conversation you define.
Pay only for what you use. No hidden fees.
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Best for one or two simulations - up to 100 participants
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