I’ve been enjoying his Facebook group, Foundations of Social Marketing:
Didn’t know that he was LDS, serving a mission in the Philippines (country of the happiest people), and even doing standup comedy.
It’s a super small world among leaders in the home services industry.
Imagine you had a rich bio like Ryan, showing your connections, companies, and accomplishments– how that would be your #1 asset to grow your home services business in your city.
Ryan Fenn is an American entrepreneur known for founding and serving as the chief executive officer (CEO) of CHIIRP, a software-as-a-service (SaaS) platform that provides automated messaging and lead conversion tools primarily for home service businesses. Through CHIIRP, Fenn has focused on leveraging text messaging, email, voicemail drops, and AI-driven automation to improve customer engagement and business growth, particularly in industries like plumbing, HVAC, and garage services. He bootstrapped the company without venture capital funding, growing it from an initial investment of $500 to approximately $8 million in annual recurring revenue (ARR).
Early life
Fenn was born and raised in Southern California in a religious family affiliated with the Church of Jesus Christ of Latter-day Saints (LDS). From a young age, he demonstrated entrepreneurial tendencies, such as selling gumballs and candy at school. He dropped out of high school at age 16, citing discomfort with the structured environment despite performing well academically and later passing the California High School Proficiency Exam with high scores. Fenn attended some community college classes but did not pursue formal higher education extensively.
After turning 18, Fenn took on various sales jobs, including selling cars. He served a two-year mission for the LDS Church in the Philippines, where he learned the local language and immersed himself in community service. In his early 20s, Fenn pursued stand-up comedy, performing clean, family-friendly sets and opening for comedians such as those from the television show In Living Color, Pauly Shore, and Daniel Tosh. He performed unpaid for several years but eventually stepped away from comedy due to lifestyle conflicts with his religious values and family aspirations.
Career
Fenn married at age 25 and moved to Utah for a better environment to raise a family. In 2010, following the birth of his first son, Maddox, and with only $500 in savings, he responded to a Craigslist ad for a windshield repair position at a car wash. He quickly excelled, repairing 5-10 windshields daily and earning $100-200 per day. After discovering fraudulent practices at the company, Fenn left and, with his brother Blake, started their own windshield repair business using $300 to purchase repair kits.
Initially door-to-door, the business expanded to gas stations and car dealerships, growing to nine locations. In 2014, Fenn created an online course called GlassPointe, teaching others how to start windshield repair businesses. He sold repair kits bundled with training, generating approximately $2 million in revenue and helping around 1,000 entrepreneurs. During this period, Fenn implemented text messaging automation for lead follow-up, which significantly boosted conversions and inspired the creation of dedicated software.
In 2018, Fenn founded CHIIRP (initially spelled CHIRP) with an initial $500 investment, developing it as a platform for automated lead nurturing across text, email, and voicemail. The minimum viable product (MVP) launched in early 2019, initially serving diverse industries like real estate and gyms before pivoting to home services in response to integrations with platforms like HouseCall Pro and ServiceTitan. This focus led to rapid growth, reaching $100,000 in monthly recurring revenue and eventually $650,000-$700,000 per month. CHIIRP has partnered with major home service entities, including Tommy Mello’s A1 Garage Door Service, and incorporates AI features for conversational follow-ups and appointment booking. Fenn has assisted over 1,500 home service businesses in scaling operations and generating leads.
Fenn has appeared on numerous podcasts, including The Home Service Expert with Tommy Mello, On the Homefront with Jeff Dudan, and Service Business Mastery, discussing topics like automation, lead conversion, and entrepreneurial mindset.
Personal life
Fenn is married and a father of four children. He attributes much of his success to faith, gratitude, and hard work, often describing key career moments as divinely guided. Fenn has self-identified as having ADHD, which he views positively as contributing to his entrepreneurial drive. He continues to engage in creative outlets, such as auctioneering for charity events.
Dennis Yu
Dennis Yu is the CEO of Local Service Spotlight, a platform that amplifies the reputations of contractors and local service businesses using the Content Factory process. He is a former search engine engineer who has spent a billion dollars on Google and Facebook ads for Nike, Quiznos, Ashley Furniture, Red Bull, State Farm, and other brands.
Dennis has achieved 25% of his goal of creating a million digital marketing jobs by partnering with universities, professional organizations, and agencies. Through Local Service Spotlight, he teaches the Dollar a Day strategy and Content Factory training to help local service businesses enhance their existing local reputation and make the phone ring.
Dennis coaches young adult agency owners serving plumbers, AC technicians, landscapers, roofers, electricians, and believes there should be a standard in measuring local marketing efforts, much like doctors and plumbers must be certified.