In high school, Holmes founded a paintball field as his first business which later became an online retailer. After dropping out of university in 1997 Holmes moved back to his hometown of Vernon and started his second business, a pizza restaurant called Growlies. He sold a franchise of the business in that year. To re-pursue his passion for computers and be a part of the emerging tech industry, Holmes sold Growlies in 1999 and moved to Vancouver. While there he taught himself internet design and development and began working at a local technology firm. Following this he founded Invoke, a digital media agency, where Hootsuite was born in 2008. In 2012, he then raised another round of funding for Hootsuite in the amount of $20 million from Canada-based VC Omers Ventures. In August 2013, Holmes announced Hootsuite had secured $165 million in a Series B round of funding, the largest ever for a Canadian software company, led by
Insight Venture Partners with participation from
Accel Partners and existing investor OMERS Ventures. Today, Hootsuite has nearly 1,000 employees, and over 16 million users around the globe and has expanded its reach into the Enterprise-level market for large-scale social media solutions. In 2013 Holmes launched an accelerator program for young entrepreneurs called The Next Big Thing (later rebranded as The League of Innovators), in part to help foster a "Maple Syrup Mafia," the term he coined in early 2013 to describe a new Canadian technology powerhouse similar to the original
PayPal Mafia. In 2016, he teamed with Steve Suchy to launch Oristand, an affordable cardboard standing desk/workstation. In 2017, Holmes came out with a book,
The 4 Billion Dollar Tweet, described by
ZDNet as, "a guide to understanding and maximizing the use of social media." It is his first book. Holmes claimed that the book inspired
Goldman Sachs Chief Executive
Lloyd Blankfein to tweet for the first time in June 2017. In 2020, Holmes started working on the startup idea platform Kern.al. ==Recognition==