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

Midlands
all
January 15, 2025
What makes Sharon’s story powerful is how it began: over 18 months of consistent follow-up with a vendor before finally securing the deal. From sourcing her properties directly to negotiating strong terms, Sharon shows what’s possible when patience meets preparation. She shares how she furnished the units cost-effectively, added smart home tech for better utility control, and secured an impressive 189-night booking across all three flats. With guaranteed rent of £1,200 per unit and high occupancy, her business is now thriving—and her journey is packed with valuable lessons for any aspiring investor. Sharon’s portfolio includes three well-located, two-bedroom flats in Worcester, each secured on guaranteed rent at £1,200 per month. Through strategic setup, smart tech, and direct sourcing, she’s maximised efficiency and income—most notably with a single 189-night booking that filled all three units. A perfect example of how strategic action and long-term thinking pay off in rent-to-rent.
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Midlands
all
March 7, 2024
Join us for an inspiring conversation with Nithia, a determined new investor navigating her way into the world of rent-to-rent. In this video, Nithia opens up about the internal battles, the learning curve, and how the power of community gave her the clarity and confidence to keep going. Her journey is filled with honest reflections, valuable lessons, and moments of real breakthrough—showing that success in property isn’t just about deals, it’s about mindset, support, and sticking with it. If you’re thinking about getting started but feel overwhelmed—this one will hit home.
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South
all
March 15, 2025
“I started working with Simon several months ago and since then I've managed to get rent-to-rent deals in the bag, with more in the pipeline. I think Simon has been the vital key to me securing my first deal because I'd worked with other people previously and they were unable to supply the level of value that Simon offers. He really pushed me to go for the deal I had on the table, and helped me through the process of saying the right things and having all of the right documents. ”
Read More
London
all
July 1, 2025
From struggling to find landlords to securing a direct deal with a property developer, Nakita’s journey into rent-to-rent shows what’s possible with persistence, smart strategy, and the right support. In this video, she shares how she built her Short Stays property business in London and scaled to three high-performing serviced accommodation units generating £12,000 per month. She reveals how the deal with a developer came about, what it took to set up each unit for success, and why guest experience and presentation have been crucial to her results. Nakita also talks openly about the challenges she faced, and how being part of the SSO mentorship gave her the tools and confidence to push through and build something she’s proud of.
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