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

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

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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Episoder(489)

He Went From a Window Tint Shop to a $400M Company (His One Hiring Rule)

He Went From a Window Tint Shop to a $400M Company (His One Hiring Rule)

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ Dustin Sims went from running a window tint shop to VP of Operations at A1 Garage Door Service — a $400 million company — in und...

7 Jul 1h 28min

The Accountability System That Makes Poor Performance Impossible to Hide

The Accountability System That Makes Poor Performance Impossible to Hide

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ More than half of private equity–backed CEOs don't make it through the hold period. Samantha Allison and Taavo Godtfersen studie...

2 Jul 1h 7min

The Operating System Behind America's Biggest Garage Door Company

The Operating System Behind America's Biggest Garage Door Company

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ A1 Garage Door is about to cross $410 million — and Garage Door Freedom exists to hand other owners the exact systems that got i...

30 Jun 39min

The Belief That Separates the People Who Win From Everyone Else | Evan Carmichael

The Belief That Separates the People Who Win From Everyone Else | Evan Carmichael

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ Evan Carmichael started with $300 a month, dead-ass broke, too afraid to  tell anyone. He sold his company at 22, built a YouTub...

30 Jun 1h 19min

Your Hiring Strategy Is Setting You Up to Fail Before Day One | Mike Matalone

Your Hiring Strategy Is Setting You Up to Fail Before Day One | Mike Matalone

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ Window Nation had 80% employee turnover. Within 6 months, Mike Matalone brought it down to 23% — without changing their sales pr...

24 Jun 1h 11min

He Grew A Company To $220M | His Warning To Every Home Service Owner

He Grew A Company To $220M | His Warning To Every Home Service Owner

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ Chuck Thokey built sales teams that generated $220 million in  revenue — and his first coaching client went from under $1 millio...

19 Jun 1h 8min

What Every Contractor Brags About, That's Actually Proving Their Brand's Working Against Them

What Every Contractor Brags About, That's Actually Proving Their Brand's Working Against Them

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ Your brand is either quietly growing your business or quietly killing it. In this episode, KickCharge Creative President Terri B...

19 Jun 49min

The Smartest Home Service Owners in the Country Are All Doing This One Thing

The Smartest Home Service Owners in the Country Are All Doing This One Thing

🚀 FREEDOM 2026 Get your Tickets Today! https://homeservicefreedom.com/ Jim Leslie is the CEO of Home Service Freedom and former CMO/CTO at A1 Garage Door — where he helped build the company to over $...

11 Jun 52min

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