About Me

As CEO and operator of Over Sea, Terra Cafe, and Birchwood Unique Accommodations, Jordan Hipson is a serial entrepreneur who has found his passion and developed a group of innovative hospitality companies with it. Currently based in Halifax, Jordan lightheartedly considers himself “aggressively Nova Scotian!”

Jordan began his professional career at the age of 13 when he created Social Communities Association (SCA). SCA was a non-profit organization that focused on educating children on the importance of cyber safety, as well as helping them discover volunteering opportunities within their community. SCA operated for several years and even had a full-functioning office in Jordan’s hometown of Cole Harbour! From there, he then launched Jordan Hipson Omnimedia (JHO) at age 17. JHO included a rapidly growing radio show that covered a vast range of lifestyle-related topics for Seaside FM in Eastern Passage. Riding on the success of the radio show (titled At Home with Jordan Hipson) JHO expanded to produce a television show with Bell, a print magazine, and a successful digital media platform across Facebook, YouTube, and “JordanHipson.com”. In 2013, Jordan shared the stage with the inspiration for Jordan Hipson Omnimedia, Martha Stewart, at Grand Central Station in New York City!

Upon finishing high school and while operating JHO for another two years, Jordan joined the family business of property and casualty insurance. Having been raised in a family of insurance brokers, Jordan quickly became the youngest accredited insurance broker in Nova Scotia. He achieved both his Canadian Accredited Insurance Broker and Life License Qualification Program designations.

Realizing his urge to return to entrepreneurship, Jordan founded Lease Better in 2015, known today as Over Sea Real Estate Management. Initially, the company supported landlords in the long-term rental space, but Jordan quickly pivoted his services in 2016 to focus on short-term rentals due to the rapid growth of platforms like Airbnb. In 2018, Lease Better became Over Sea and has since grown to become the leading vacation home manager in Atlantic Canada, with luxury vacation homes throughout Nova Scotia and Newfoundland & Labrador. Following the advice he shared with his clients, Jordan entered the world of real estate investing himself in 2020 by developing his first tiny cabin in Cheverie, Nova Scotia. The cabin gained immense traction as a short-term rental, ultimately inspiring Jordan to begin working on his second unique accommodation in the same area.

Continuously working towards his goals in the hospitality industry, Jordan has also practiced as a business consultant for government agencies and entrepreneurs throughout Canada. Focusing on real estate investing/management, hospitality startups, and digital operations and marketing Jordan has worked on political campaigns, and has helped launch businesses such as 470 Main Boutique Hotel, Chester's Cafe and Social House, Sidekick Cafe, and AOI Renovations. 

In late 2021 Jordan embarked on his next business endeavour – the launch of Terra Café. Terra is located in the historic Alexander Keiths’ Brewery building in Halifax, and was created with a burning passion to deliver the same level of quality that is expected of Jordan in his other endeavours. Offering unique experiences with elevated quality is something that Jordan does best.

As a dynamic professional driven by values and respect, nothing makes Jordan happier than effectively translating business visions into profitable realities – all while ensuring everyone across the organizational pipeline has positive, constructive experiences along the way. From his own businesses to consulting, he has a genuine ardency for maintaining continuous growth and empowering others with in-depth guidance that enables them to solidify future success. This, in conjunction with his rich interpersonal skills, strategic approaches for every decision, and reputation for exceeding expectations, are what led Jordan to become the multi-industry leader he is today who continuously strives to raise the hospitality standards bar.