Damien Cheeseman on Financial Freedom & Property Investment

In a recent episode of the Self Unemployed Podcast, host Colin Munro sat down with Damien Cheeseman at the Belvoir Estate, where Damien manages a portfolio of serviced accommodation properties. The conversation covered Damien’s journey to financial freedom, his business ventures, and his insights on property investment, wealth-building, and breaking free from societal conditioning. A key part of the discussion focused on the influence of Samuel Leeds and his Academy, which played a pivotal role in Damien’s property career.

From Double Glazing to Multi-Million Pound Ventures

Damien’s entrepreneurial journey began with door-to-door double glazing sales to fund university, but he opted out of higher education after realizing he could earn comparable money without a degree. This decision led him to establish a construction company, which he ran for 13 years, growing it to a turnover of £4-6 million annually. The business is now systemized, allowing Damien to step back from daily operations and focus on property investment.

About two years ago, Damien entered the property market, leveraging his construction expertise. He emphasized the importance of creative strategies to make property investment financially viable, moving beyond the traditional buy-renovate-sell model, which often yields limited profits after taxes. Instead, he focuses on strategies like rent-to-rent and serviced accommodation to generate passive income and build wealth.

Damien Cheeseman: Managing the Belvoir Estate Portfolio

A significant milestone in Damien’s career was securing a deal to manage the serviced accommodation portfolio for the Belvoir Estate, owned by the Duke and Duchess of Rutland. Initially, Damien approached the estate for a 30-year rent-to-rent deal on a single derelict property. However, during negotiations, he boldly suggested managing their entire portfolio to avoid competition between properties. After a successful trial, the Duchess entrusted Damien’s team with the full portfolio, which includes boutique hotels, cottages, and lodges. His team has since doubled the estate’s turnover and is expanding with new properties under renovation.

Building Wealth Through Good Debt and Asset Accumulation

Damien and Colin discussed the concept of “good debt” versus “bad debt.” Good debt, such as a mortgage on a property generating rental income (e.g., £2,000 monthly profit against a £500 mortgage payment), builds assets and wealth. Bad debt, like loans for holidays or depreciating assets like cars, offers no return and burdens finances. Damien highlighted how societal conditioning often discourages good debt, pushing individuals toward savings accounts that lose value due to inflation outpacing interest rates since 2008.

Drawing from Robert Kiyosaki’s Cash Flow Quadrant, Damien explained his transition from a self-employed mindset to a business owner and investor. He systemized his construction company to run independently, freeing him to focus on property investments that build equity and passive income. He stressed that wealth, not just money, is key to financial security, as currencies can fail, but assets like property retain value due to increasing demand and limited land.

Critique of Traditional Education and Financial Systems

Both Damien and Colin critiqued the education system for failing to teach financial literacy, such as understanding investments, good debt, and wealth-building. They argued that society conditions individuals to prioritize job security over financial freedom, trapping them in a cycle of dependency. Damien shared his realization that his construction company’s profits were heavily taxed, prompting him to educate himself on smarter investment strategies. He believes the internet and platforms like YouTube have made financial education more accessible, empowering a new generation to break free from traditional constraints.

Samuel Leeds and His Academy

Damien’s entry into property was catalyzed by Samuel Leeds’ Academy, which he joined 23 months ago after attending a £1 crash course in June 2023. Both he and Colin praised the Academy for its value, dismissing critics who label it a scam. They emphasized that the low-cost entry point allows anyone to explore property investment without significant risk. Damien Cheeseman was inspired by Samuel’s energy, the Academy’s community, and the practical strategies taught, such as rent-to-rent and serviced accommodation. He likened Samuel’s teachings to a “recipe for baking a cake,” noting that success depends on applying the knowledge with hustle and tenacity. The Academy’s supportive network, including local groups and Inner Circle meetings, was highlighted as a key resource for aspiring entrepreneurs.

Colin shared a similar experience, initially skeptical due to negative online comments about Samuel’s passionate marketing but convinced after attending a crash course. They both encouraged listeners to attend a £1 course to gain firsthand insight, arguing that the minimal cost negates scam accusations. Damien credited the Academy for shifting his mindset and equipping him with the tools to scale his property portfolio. Click Here for more information on Samuel Leeds’ Academy.

Advice for Aspiring Investors from Damien Cheeseman

Damien advised young and aspiring investors to educate themselves through courses like Samuel Leeds’ Academy or by connecting with successful investors. He emphasized that property investment doesn’t require substantial capital, as good debt can bridge the gap. His company, Damien Cheeseman Properties, works with investors who have liquid cash, underperforming single-let properties, or rundown assets needing renovation. By leveraging his construction expertise and property management team, Damien helps investors maximize returns through serviced accommodation and joint ventures.

Future Plans and How to Connect with Damien Cheeseman

Damien is focused on scaling his portfolio by onboarding more investors and securing off-market deals. His team, consisting of five employees, manages properties across the UK and Switzerland, with plans to expand further. He invites potential investors to contact him via Instagram (@damiencheesemanproperties) for opportunities in serviced accommodation and property development.

Key Takeaways

• Entrepreneurial Mindset: Damien’s journey underscores the importance of challenging societal norms and pursuing financial freedom through education and action.
• Wealth vs. Money: Building assets through good debt and strategic investments is crucial for long-term financial security.
• Samuel Leeds’ Academy: A valuable resource for learning property investment strategies, offering a