Ryan’s business success story was written from humble beginnings. Raised in Sheffield and growing up on one of the area’s largest council estates, he left school at the age of around fifteen/sixteen and launched his first venture with his own capital, selling double glazing.

He has since gone on to become a self-made businessman having built a market-leading enterprise. Across his portfolio of businesses, Ryan now employs more than 1,000 individuals directly and indirectly, as well as boasting over 35 years of experience as a businessman. 

Staysure Group was born in 2005 and is the UK’s market leader in travel insurance with the likes of Rock, Paying Too Much and Avanti all under its wing. With his insurance companies Ryan has changed the perspective of an entire sector on the realms of what was possible for generations of travellers, and moved the parameters to ensure that individuals over 50 can travel at any age, irrespective of any existing health condition. He was also the first to market with travel insurance for Covid-19 cover in 2020.

From his own learnings as an entrepreneur, Ryan has devised his own unique business system, 90 Days, which is deployed in all the companies he works with and invests in. It is designed to help staff, individuals and entrepreneurs meet their objectives and goals and comes as a downloadable app. 

Ryan’s motivation is to use his own experience of achievements, set-backs and life learning to support others. He overcame a serious illness earlier in life, and adheres to a strict and very healthy diet and daily exercise regime as well as a holistic approach to life and fitness.

Ryan invests into businesses through his private equity investor, Howsam Ltd, which specialises in the mature affluent market. Investment size is between £5 and £100 million, with a target range of investments covering the financial services, leisure and technology sectors. 

Outside of business, Ryan is a professional golfer having recently qualified. It has long been one of his life passions, having wanted to play the professional game having left school, before venturing on his business journey. He sponsored what was called the Staysure European PGA Tour’ and then invested personally to become the major shareholder. The name then changed to the Legends Tour of which he is now CEO. This is a major fixture and competition in the golfing world engaged in by the world’s leading names and legends in the sport.

Ryan is a regular speaker on topical matters and issues of the day including travel disruption, vaccine passports, the future of travel in the post-pandemic world, and his views on government policy. He also speaks on many aspects relating to UK business, entrepreneurship, mentoring and investing, including what he looks for in businesses and entrepreneurs he wishes to invest in.

In August 2021, Ryan appeared on a Leaders Council of Great Britain & Northern Ireland podcast, discussing the importance of leadership and the impact it has had on his career to date.