Ishita Dosi

Most founders practice their pitch with friends, co-founders, or other founders - people who aren't going to ask the questions that actually trip you up in a real investor meeting. This session is different.

I'll play investor. You pitch. Then I'll interrogate exactly the way an early-stage investor would on market size assumptions, competitive moat, unit economics, team risk, and the parts of your story that aren't landing. No softballing.

Here's how the session runs:

1. 5 min: quick brief on who you're pitching to (what kind of fund, what stage, what sector thesis) so I can calibrate the investor persona
2. 15 min: you pitch, uninterrupted, as if it's a real meeting
3. 25 min: I ask investor questions, the ones that expose gaps, challenge assumptions, and test whether you can think on your feet
4. 15 min: debrief. What worked, what didn't, what to fix before your real meetings

You'll receive a written debrief within 24 hours covering: the 3 strongest moments in your pitch, the 3 questions you need better answers to, and specific language improvements.

This session is best for founders who:

1. Have investor meetings in the next 2–4 weeks and want a pressure test
2. Have had meetings but keep getting stuck on the same questions
3. Feel confident about the deck but not the live conversation
4. Are raising for the first time and have never been in a real investor meeting

Background: I evaluate and invest in early-stage startups through Ecosystem Ventures and as an angel investor. I know the questions investors ask because I ask them.