AI booked 650 meetings, and almost got a date episode artwork

EPISODE · Mar 25, 2026 · 56 MIN

AI booked 650 meetings, and almost got a date

from AI for Founders with Ryan Estes · host aiforfounders.co

There is a moment in every founder's journey where they realize the bottleneck in their pipeline is not their product, not their pricing, and not their pitch. It is time. Specifically, the time between when a prospect raises their hand and when someone, or something, responds.Will Del Principe discovered this the hard way. At 16, he was a solar sales rep dialing through a list of thousands of warm leads on an iPad, burning out after five or six calls, leaving a fortune in uncontacted interest sitting in a CRM. A decade later, he is the head of growth at Thoughtly, an AI voice agent platform that calls those same kinds of leads within 10 seconds of form submission, runs 13,000 calls a month for a single client, and once had to be reprogrammed after one of its agents agreed to go get coffee with a prospect.This episode is about what happens when you stop asking humans to do what machines can do endlessly, and start letting your best salesperson work around the clock without ever needing a break.https://www.thoughtly.com/https://www.linkedin.com/in/will-del-principe-57b18b2a5/⁠https://www.linkedin.com/in/estesryan/⁠⁠https://aiforfounders.co⁠⁠⁠https://kitcaster.com/application ⁠⁠⁠⁠https://ryanestes.info⁠⁠

There is a moment in every founder's journey where they realize the bottleneck in their pipeline is not their product, not their pricing, and not their pitch. It is time. Specifically, the time between when a prospect raises their hand and when someone, or something, responds.Will Del Principe discovered this the hard way. At 16, he was a solar sales rep dialing through a list of thousands of warm leads on an iPad, burning out after five or six calls, leaving a fortune in uncontacted interest sitting in a CRM. A decade later, he is the head of growth at Thoughtly, an AI voice agent platform that calls those same kinds of leads within 10 seconds of form submission, runs 13,000 calls a month for a single client, and once had to be reprogrammed after one of its agents agreed to go get coffee with a prospect.This episode is about what happens when you stop asking humans to do what machines can do endlessly, and start letting your best salesperson work around the clock without ever needing a break.https://www.thoughtly.com/https://www.linkedin.com/in/will-del-principe-57b18b2a5/⁠https://www.linkedin.com/in/estesryan/⁠⁠https://aiforfounders.co⁠⁠⁠https://kitcaster.com/application ⁠⁠⁠⁠https://ryanestes.info⁠⁠

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AI booked 650 meetings, and almost got a date

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This episode is 56 minutes long.

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This episode was published on March 25, 2026.

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There is a moment in every founder's journey where they realize the bottleneck in their pipeline is not their product, not their pricing, and not their pitch. It is time. Specifically, the time between when a prospect raises their hand and when...

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