Meet

Anne & Jeff

From day jobs to full time property investors

Lifetime Cashflow

Monthly Cashflow

Number Of Deals

Rent to rent allowed us to quit our jobs

Watch the video below to find out how.

Anne and Jeff are now full time property investors. Until recently, Anne was a supply chain analyst for a pharmaceutical company and Jeff ran a business building and designing pipe organs, which he still does on the side. Working with Simon, they have secured five rent to rent deals, and property is now their main focus. They talk about what it was like having Simon on the call for their first deal, and how that support was pivotal.

Hear Anne and Jeff's story on The Simon Smith Show

How Anne and Jeff replaced their jobs with rent to rent

Working with Simon is a practical, real life experience. When we worked together on our first deal, him stepping in on the call, making sure we were asking the right questions, it was like being hand held, and that was pivotal. Simon, because he's in the rent to rent business, knows what to avoid. He helps you see what value you can offer and how to communicate that effectively.

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January 1, 2026
Charmaine and Stuart did not want retirement to mean cutting back or giving up the life they had worked for. They wanted to travel, enjoy their time and build enough income to support the future they had planned. Rent to rent stood out because it let them create strong monthly cashflow without buying property first. Within three months of joining SSO, they had secured their first deal. Their second followed quickly, and they are already negotiating deal three.
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Jim was a hospitality managing director running 47 bars across the country before he walked away to pursue financial freedom through rent to rent. Starting from scratch, he signed three deals in just seven weeks, including a standout property in central Soho. His move from hospitality to property shows what happens when experience meets action.
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Ryan from South East London is proof that slow and steady still wins. In his first year, he built a portfolio of two well run units that bring in steady income. He shares what it really looks like to grow without the noise: focused action, strong relationships and a long term mindset. If you want a grounded, real world look at how rent to rent works over time, this is it.
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Rob and Emine had zero property experience. Today they run a 15 property rent to rent business with nearly £600,000 in turnover. They share how they built it from the ground up, the challenges they faced and what they would do differently if they started again. From their first deal to scaling their systems, they open up about what it really takes, and how they turned uncertainty into unstoppable momentum.
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