Michael Castello AI BIO

Early Background and Personal Challenges

Michael Castello, born Michael Anthony Castello, began his career in the music industry as a singer-songwriter under the stage name Michael Seven. Mentored by Tin Pan Alley legend Lou Stallman, he performed in New York City before moving to Los Angeles with his brother David, where their band played at iconic venues like the Roxy and Whisky a Go Go. Additionally, Michael produced the nationally syndicated gospel radio show Gospel Traxx for 15 years, earning a Billboard Magazine nomination for top R&B syndicated radio. Sheri Castello, whom Michael married in the early 1990s, supported his creative pursuits and later played a pivotal role in his personal recovery and entrepreneurial shift.

In January 1994, the Northridge earthquake struck Los Angeles, exacerbating Michael’s health issues; he was initially diagnosed with an incurable condition, leaving him bedridden and facing a dire prognosis. At the time, the couple had a 2-year-old son, Jonathan, and Sheri became his primary caregiver, preparing gluten-free meals and fresh juices to aid his recovery. After two years of uncertainty, Sheri insisted on a second medical opinion over Christmas 1995, which revealed the initial diagnosis was incorrect, allowing Michael to regain his health.

Transition to the Internet and Domain Vision

During his recovery in late 1994, Michael spent extensive time on the computer, immersing himself in the emerging “Information Super-Highway.” This period sparked his vision of the internet as “digital real estate,” leading him to register his first domain, Powwow.com, for his production company Powwow Productions—after months of trial and error, as most premium names like Hollywood.com were still available for free. By March 1995, he had registered Whisky.com (inspired by his love of Scotch and the Whisky a Go Go nightclub) and PalmSprings.com, marking the start of his domain portfolio.

In 1995, Michael co-founded Castello Cities Internet Network, Inc. (CCIN) with his brother David, focusing on acquiring, developing, and monetizing premium geographic and lifestyle domains. Early developments included transforming PalmSprings.com into a tourism guide by the early 2000s, generating revenue through local advertising partnerships. Other acquisitions, like Nashville.com in 2003 and Traveler.com in the mid-1990s, followed suit, evolving into comprehensive platforms for events, dining, real estate, and travel content. Michael’s daughter Jessica later became editor of Traveler.com.

Founding Daycare.com

Inspired by his experiences as a new father to Jonathan, Michael registered Daycare.com in 1997 and co-founded the platform with Sheri. The site launched as a free online directory for childcare services across the United States, aiming to connect parents with daycare providers and operators. It quickly grew into a vital resource, integrating data from state databases to offer comprehensive listings. Over time, it transitioned to a paid model to ensure higher-quality, up-to-date information, encouraging providers to claim and maintain their profiles.

Sheri’s involvement stemmed from their shared parenting journey, though details on her independent professional background are limited beyond this collaboration. The couple’s family life in Moorpark, California—now including daughter Jessica—remained central, with Jonathan growing up to become CCIN’s Chief Technical Officer.

Later Achievements and Legacy

Michael’s domain expertise expanded beyond Daycare.com. In the late 1990s, he developed Whisky.com into a top-ranked site with extensive brand pages, networking at events like WhiskyFest to build partnerships. After early lowball offers (e.g., $1,000 in 1996, rejected for $10,000), he sold it in 2014 for $3.1 million to Europe’s largest whisky supplier—the domain, originally free, netted a massive return through broker Toofun. Other sales included Room.com for $1.5 in 2018.

Recognized as a domain pioneer, Michael was inducted into the TRAFFIC Domain Name Hall of Fame in 2009 and the Geo Domain Hall of Fame in 2010. He has spoken internationally at conferences, served on ICANN’s Business Users Constituency since 2008, and remains CEO and President of CCIN, as well as Chairman of Daycare.com Inc. (which licenses the domain from Daycare.com LLC). As of April 2025, he announced plans to modernize Daycare.com further.

Sheri continues to support Michael’s ventures while prioritizing family, embodying the personal motivations behind their 1997 founding. Together, the Castellos exemplify early internet entrepreneurship, turning parental insights and digital foresight into enduring online assets.