Meet

Anne & Jeff

Discover their journey after joining the Rent-to-Rent 2.0 Inner Circle..

Lifetime Cashflow

£540,000

Monthly Cashflow

£9,100

Number Of Deals

13 Deals (8 x HMO, 4 x SA)

Rent-to-Rent allowed me to quit my job.

Watch the video below to find out how.

Anne and Jeff are now full-time property investors, but up until very recently, they were still working in their prospective careers. Anne was a supply chain analyst for a pharmaceutical company. Jeff had a business building and designing pipe organs, which he continues to do on the side, with property now his main focus. After working with Simon and joining his Mastermind they have now successfully secured five Rent-to-Rent deals! This generates her £3,950 cashflow!

Hear Anne & Jeff's story on the Simon Smith Online Show

£9,000 monthly cashflow deal...

Meet Anne and Jeff, R2R 2.0 mentees who are using rent-to-rent to feed a family of four and quit their day jobs by controlling properties they don't own, which is bringing in a whopping £9,000 per month! “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. Over the last eight months we’ve acquired three deals. Simon, because he’s in the Rent-to-Rent business, he knows what to avoid, he helps you see what value you can offer and how to communicate that effectively.”

More Case Studies

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October 16, 2025
Meet Stephanie Limuaco, a full-time digital project manager, mum, and driven property entrepreneur, who found herself stretched thin trying to balance family, a demanding career, and the early stages of a rent-to-rent business in London. With mounting pressure to make the numbers work fast, limited capital, and a string of dead-end viewings and difficult negotiations, the dream started to feel distant. But she didn’t give up. Instead, with the right support and sharper execution, she turned a corner, securing her first deal and generating over £2,000 per month profit on Airbnb. This is a raw, real journey of overcoming doubt, delays, and decision-fatigue to finally get traction in a business that’s now starting to work for her. If you’re battling overwhelm and second-guessing whether it’s worth it, this one’s for you.
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London
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July 1, 2024
Imagine going from zero property experience to running a business that’s generated nearly £600,000 in turnover—all through rent-to-rent. That’s exactly what Rob & Emine have achieved. They share how they built a 15-property portfolio from the ground up, the challenges they faced, and what they’d do differently if they started again. From landing their first deal to scaling their systems, Rob & Emine open up about what it really takes to grow a successful rent-to-rent business—and how they turned uncertainty into unstoppable momentum. Whether you’re just starting out or scaling up, their journey is packed with real lessons, powerful mindset shifts, and practical advice you can act on.
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South
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April 15, 2026
Simon and Celen Sullivan had carried the desire to start their property journey for a long time. After growing up in East London, living in Essex for almost 30 years, and later moving to Littlehampton on the south coast, they had spent most of their lives working various jobs, raising their family, and building a life together. Married for 38 years, with two daughters and two young grandchildren, they reached a stage where they wanted to build something new for their future. Their pensions were not where they wanted them to be, and they wanted to create a retirement fund that could give them more financial security in the years ahead. Rent-to-rent gave them a practical way to start building income from property without needing to buy a house first. Since joining SSO, Simon and Celen have secured two rent-to-rent deals and started proving to themselves that it is not too late to build something new. For them, this is not just about property. It is about seizing the opportunity, putting in the work, and creating a stronger future for themselves and their family.
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London
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April 21, 2024
Meet Ricky and Roxie—a software engineer and a communications consultant who turned a three-year plan into a six-month success story. With no prior experience in rent-to-rent, they’ve built a property business generating over £30,000 in monthly revenue—and they’re just getting started. Ricky and Roxie now operate a portfolio of rent-to-rent units that generate over £30,000 in monthly revenue—all within just six months of starting their journey. With a sharp focus on relationship-building and operational systems, their deals are built on solid fundamentals and long-term vision. This case study showcases not just a single property, but a rapid business transformation powered by purpose, strategy, and execution. Whether you're just getting started or ready to scale, this is a must-watch for anyone serious about financial freedom through property.
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