Richard began his entrepreneurial journey in 2009 after leaving his role as a Business Development Manager for a supported employment charity. He started by offering bid writing services and social enterprise consulting before transitioning into website development and SEO.

In 2012, he launched a Shopify store selling prints of iPhone panorama photos, which was featured on the Shopify blog. At the same time, he built a portfolio of SEO clients, which he later sold in 2013. To document his 1,000-day journey in entrepreneurship, he wrote Coffee Shop Entrepreneurs.

In 2016, Richard sold his Shopify store on Empire Flippers, realizing the value of building digital assets. This led him to sell FunnelEngine.com through FE International in 2017, where he later helped an investor flip the site for twice its value.

Recognizing the potential in website investing, he founded Flipping Websites, a business that provided operational services to investors and built a thriving Facebook community and podcast. He sold the business in 2019 to Alpha Investors, which later became Investors Club.

In 2020, Richard launched Website Investing, a newsletter and podcast focused on digital asset investing. It gained traction and was later acquired by Travis Jamison, earning recognition on They Got Acquired. His expertise in the space led him to sell the alts.substack.com newsletter and Discord community to Flippa in 2022.

The following year, he exited multiple digital properties, including acquire.gg and two Beehiiv newsletters, selling them to Scott Oldford at The Wisdom Group. As an early adopter of Beehiiv, he also secured an investment in their Series A round.

In 2024, he launched WhyNot.Bot, an AI automation agency helping charities secure funding. By 2025, his focus shifted toward AI-driven automation, leading to the launch of AI Agents: Digital Asset Pros on Whop.

Richard continues to explore the intersection of AI, digital assets, and online business, helping others navigate and capitalize on emerging opportunities.