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The Home Service Expert Podcast

How AI Is Closing Deals for Home Service Businesses with Chiirp (Ryan Fenn)

The Home Service Expert Podcast

Tommy Mello

Management, Business

4.7793 Ratings

🗓️ 27 March 2026

⏱️ 64 minutes

🧾️ Download transcript

Summary

Ryan Fenn is an entrepreneur and the founder and CEO of Chiirp, a software company focused on helping home service businesses convert more leads into booked jobs. A lifelong entrepreneur, Fenn built his career from the ground up—starting with a windshield repair business he launched with just a few hundred dollars and scaling it into a multi-location operation.

Through his early experience in sales and home services, Fenn identified a major gap in the industry: most companies weren't losing revenue because of poor marketing, but because of inconsistent and slow follow-up with leads. This insight ultimately led him to create Chiirp, which automates customer follow-up across multiple channels, including text messages, emails, voicemail drops, and more.

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Transcript

Click on a timestamp to play from that location

0:00.0

There's hundreds of millions of people sitting on social media looking at the phones all day every day,

0:04.4

and you can be in front of them in a few seconds.

0:07.6

And if you play that game, the sky is the limit.

0:10.7

Welcome to the Home Service Expert, where each week, Tommy chats with world-class entrepreneurs and experts in various fields,

0:18.3

like marketing, sales, hiring, and leadership, to find out what's really behind their success in business.

0:25.3

Now, your host, the Home Service Millionaire, Tommy Mello.

0:30.0

Before we get started, I wanted to share two important things with you.

0:33.4

First, I want you to implement what you learned today.

0:36.1

To do that, you'll have to take a lot of notes, but I also want you to fully concentrate on the interview.

0:41.8

So I ask the team to take notes for you.

0:43.8

Just text notes, N-O-T-E-S, to 888-526-1299.

0:50.8

That's 888-526-1299, and you'll receive a link to download the notes from today's episode.

0:58.6

Also, if you haven't got your copy of my newest book, Elevate, please go check it out.

1:03.4

I'll share with you how I attracted and developed a winning team that helped me build a $200 million company in 22 states.

1:09.5

Just go to elevate and win.com for slash podcast to get your copy.

1:13.9

Now let's go back into the interview.

1:15.6

All right, guys, big day for me.

1:17.4

I got Ryan Finn in the House.

1:18.8

He's the CEO and founder of Cherp.

1:20.9

He's based out of Eagle Mountain, Utah, and knows a lot about automations.

1:26.4

I met Ryan years and years ago at a vertical track

1:30.9

Rajore event that we were hosting. And he and I and one of his major developers, Kevin, said

...

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