AI booked 650 meetings, and almost got a date
with Will Del Principe, Thoughtly
AI booked 650 meetings, and almost got a date
Show Notes
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 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.
The Thoughtly Origin Story
Will was not a developer. He was a yacht captain who watched ChatGPT launch and made a decision: he was not going to miss this wave. He shut everything down, built an AI agency, tested five voice agent platforms, and landed on Thoughtly because of one customer service rep named Max who picked up immediately and actually helped. The CEO found Will inside the platform two weeks later with 20 agents built. A coffee meeting followed. Two and a half years later, Will is still there - and the company has raised over $10 million in total funding.
The lesson buried in that story is not about AI. It is about responsiveness. Thoughtly won Will as a customer the same way Thoughtly wins deals for its clients: by showing up fast, with warmth, and with the right information.
Frameworks from This Episode
These frameworks have been added to the AI for Founders Frameworks Library. Filter by Sales or Will Del Principe to find them.
Speed to Lead
The first company to contact a warm lead wins. Almost always. Response time measured in seconds, not hours.
- •A lead filling out a form is actively shopping - likely on multiple competitor sites simultaneously.
- •Calling within 5–10 seconds of form submission dramatically increases connection and conversion rates.
- •Waiting until the next day means the prospect has almost certainly already moved on.
- •AI voice agents trigger a call the moment a form is submitted, arriving with personalized CRM context.
- •A personalized opener outperforms a cold opener every time - longer conversations, lower hangup rates.
High Consideration B2C
Target verticals where the psychology and economics of AI voice agents work together.
- •High consideration = mortgages, insurance, real estate, education enrollment.
- •Prospects often fill out half an application, step away to think, and go cold.
- •That contemplation window is exactly where AI reactivates interest before it disappears.
- •Low consideration purchases don't benefit - the margin and psychology don't support it.
- •AI is not the closer. AI is the qualifier, gatekeeper, and appointment setter.
The Reactivation Play
Your CRM has a goldmine of opted-in leads who went cold. AI voice can restart those conversations at scale.
- •Most businesses have thousands of leads who showed genuine interest but never converted.
- •Opted-in leads satisfy compliance requirements - cold calling with AI is illegal in all 50 states.
- •Emailing these leads produces diminishing returns. Voice reactivates context and emotion.
- •One Thoughtly client booked 650 meetings in 90 days and saved $400,000 in headcount costs.
Training the Agent on Your Voice
Feed your best sales calls into the knowledge base. The result scales infinitely and never has a bad day.
- •Record your best sales calls or objection responses.
- •Feed those recordings directly into the agent's knowledge base.
- •The agent learns your rhythm, style, and how you navigate pushback.
- •Pair with an assertiveness dial to control pipeline aggression.
The GTM Ladder for AI Agencies
A blueprint from scratch to a million-dollar run rate in AI automation.
- •Start where your knowledge already lives - your industry expertise is your moat.
- •Learn one automation that solves a real problem in that vertical.
- •Go to market immediately, even for free. First three goals: testimonials, case studies, referrals.
- •Let those compound into a repeatable, scalable offer. Do not wait until it is perfect.
Founder Experiment: Build a Speed-to-Lead Bot in a Weekend
Using AI code tools like Claude, Cursor, or Replit, build a lightweight proof of concept that calls a lead within 60 seconds of a form submission.
- 1Set up a simple form using Typeform or Tally that captures name, phone number, and inquiry type.
- 2Connect the form to a webhook using Make.com or n8n. When a form is submitted, the webhook fires.
- 3Use an AI code tool to write a script that triggers a call via Twilio or a voice AI provider like Thoughtly, ElevenLabs, or Bland AI. Pass the prospect's name and inquiry type into the opening script.
- 4Prompt your AI engineer to write a call script with a natural opener, two qualifying questions, and a calendar booking link delivered via SMS at the end of the call.
- 5Run 10 test calls on warm leads. Measure hangup rate, conversation length, and booking rate against your current follow-up method.
Stretch goal: Feed three of your best real sales calls into the knowledge base and instruct the agent to mirror your objection handling style. Compare conversion rates between the generic and trained versions.
Key Terms
These terms have been added to the AI for Founders Glossary. Search by Will Del Principe to filter them.
Tools from This Episode
Thoughtly
AI voice agent platform that calls warm leads within 10 seconds of form submission - 24/7, at unlimited scale. One client booked 650 meetings in 90 days and saved $400,000 in headcount.
Q&A
What is Thoughtly and what does it do?
Thoughtly is an AI voice agent platform specialized in outbound sales automation. It enables businesses to automatically call warm leads within seconds of form submission, qualify prospects, answer objections, and book appointments - all without a human on the line.
Is it legal to use AI voice agents for outbound sales calls?
Cold calling with AI voice agents is illegal in all 50 US states. However, calling opted-in leads - people who voluntarily submitted their contact information - is permitted. Compliance requirements vary by state, so consulting a legal professional is always recommended.
What industries benefit most from AI voice agents?
Real estate, insurance, mortgage, and education are the highest-performing verticals because they involve high consideration purchases where prospects often research, pause, and go cold before converting.
How fast should a business follow up with a new lead?
Within 5–10 seconds of form submission is the benchmark Thoughtly recommends. The longer the delay, the higher the probability that the prospect has moved to a competitor. Speed to lead is the single most impactful variable in outbound conversion rates.
Can AI voice agents be trained to sound like a specific salesperson?
Yes. By feeding audio recordings of real sales calls into the agent's knowledge base, the AI learns the cadence, tone, objection handling, and conversational style of the human it is trained on. The result sounds and responds like your best rep, available at unlimited scale.
Are there industries where AI voice agents should not be used?
Yes. Industries requiring deep human empathy at a moment of crisis are not appropriate - funeral homes are the clearest example cited in this episode. Any context where a caller is experiencing acute grief, trauma, or medical emergency requires a human on the other end of the line.