From Music to Million-Pound Cash Flow: Simon’s Unexpected Journey
Simon Smith didn’t start as a property expert. In fact, just a few years ago, he was immersed in the music industry—gigging as an MC and writing songs for major artists like Britney Spears. But when royalty checks didn’t pay the bills and a freezing job selling insurance outside a supermarket became reality, he knew it was time for a drastic change. That’s when he stumbled upon the rent-to-rent (R2R) model—a strategy that would radically transform his financial trajectory.
Today, Simon has completed over 70 rent-to-rent deals, both in HMOs and serviced accommodation (SA), and owns properties funded entirely by the cash flow from controlling properties he doesn’t own. His talk at the HMO Summit 2023-24 was a high-energy, brutally honest session on why controlling cash-generating assets beats owning them outright—for at least the first phase of your investing career.
The Billionaire’s Blueprint: Control Over Ownership
Simon kicked off with an inspiring story from the Maldives, where he learned of a Malaysian billionaire who leased a lagoon (not an island), developed four manmade islands, and subleased two of them to Ritz-Carlton. This, Simon said, is billion-dollar rent-to-rent—an extreme version of controlling assets to cash flow them at scale. The takeaway: you don’t need ownership to generate wealth—you need control and creativity.
This set the tone for Simon’s own approach. Rent-to-rent allowed him to build a property portfolio without the massive capital outlay required for purchasing. His strategy? Control for cash flow first, then buy later when the cash reserves make ownership less risky.
Cash Flow vs. Capital Appreciation: What Matters More?
Throughout his talk, Simon addressed the age-old debate: should you chase cash flow or capital growth? Most investors lean toward owning assets for long-term appreciation, but Simon challenged this assumption:
- Appreciation is often theoretical. Most landlords don’t sell, so the wealth stays on paper.
- Refinancing is slow. Even the best BRRRR (Buy, Refurbish, Refinance, Rent, Repeat) strategy takes months to realize value.
- Cash flow is immediate and usable. It pays for your lifestyle now—not 20 years from now.
He emphasized that a rent-to-rent business generating £20,000/month could easily be valued and sold just like a traditional business. That’s an asset in itself, and one that gives you both speed and lifestyle.
Control Without Ownership: Better ROI, Lower Risk
Simon illustrated a key point using a powerful example: two properties side by side, each generating £1,000/month in income. One requires a £197,000 investment to buy; the other, just £10,000 to control via R2R. The returns? Identical. So why tie up so much capital in ownership when you can control multiple properties for the same amount and multiply your cash flow?
He acknowledged the emotional satisfaction of owning, but for him, it’s all about Return on Effort and Return on Time. Controlling more with less makes sense—especially early in your investing career.
The Problem with Debt, JV Partners, and Complexity
One of the most honest parts of Simon’s talk was his reflection on debt and joint ventures. While the property world often celebrates “good debt” and JV partnerships, Simon argued that simplicity is underrated:
- Too many JV partners = too many moving parts.
- Too much debt = sleepless nights.
- Banks can call in loans. JV partners can change their mind.
Instead, he recommends reinvesting your R2R profits into assets you fully control, ideally with minimal debt and no outside interference. His own preference is to JV only with his wife—a setup that aligns incentives and reduces conflict.
Exit Flexibility and Peace of Mind
A little-discussed benefit of R2R is flexibility. If you need to exit a property you control, a simple 2-month notice period does the job. Contrast that with selling a mortgaged property, which can be expensive, slow, and emotionally taxing. The optionality of R2R means you’re less exposed during downturns or personal crises.
Development Headaches vs. Rent-to-Rent Speed
Simon also shared a cautionary tale about a £1.2 million development that turned into a two-year nightmare due to planning delays, restrictive covenants, and a bankrupt builder. The project drained time, energy, and capital.
In contrast, R2R deals can be secured, set up, and cash-flowing within days or weeks. Year one of his R2R journey saw him onboard 20 deals and earn £20K/month in profit—nearly impossible with developments.
The Rent2Rent 2.0 Model: The Best of Both Worlds
Simon’s current approach? Something he calls Rent2Rent 2.0—a hybrid strategy where he controls properties for high cash flow, systemizes the operations, and uses the profits to buy long-term assets slowly and safely. He’s now on properties #9 and #10, almost entirely funded through rent-to-rent cash flow.
This method allows him to live well today while building generational wealth for tomorrow. No heavy reliance on OPM (Other People’s Money), no stress from joint ventures, and plenty of room to enjoy the journey.
Final Lessons: Cash Flow First, Lifestyle Always
Simon’s closing message was both motivational and strategic:
“Think about where you were when you started and what your goal was. You’ve got to improve your life today. You owe it to yourself and your family.”
He reminded attendees that the property game should be enjoyable. If you’re only investing for a retirement 30 years away, what happens if you never make it there?
Instead, focus on building a lifestyle you can enjoy today. For Simon, rent-to-rent made that possible—and it might just do the same for you.
Rent-to-rent is not a stepping stone. Done right, it’s a powerful business model in its own right. It offers speed, scale, flexibility, and cash flow—everything a modern investor needs to build wealth and enjoy the process. If you’re looking to grow your property portfolio without tying up hundreds of thousands in deposits and debt, Simon Smith’s model is one to seriously consider.
From Music to Million-Pound Cash Flow: Simon’s Unexpected Journey
Simon Smith didn’t start as a property expert. In fact, just a few years ago, he was immersed in the music industry—gigging as an MC and writing songs for major artists like Britney Spears. But when royalty checks didn’t pay the bills and a freezing job selling insurance outside a supermarket became reality, he knew it was time for a drastic change. That’s when he stumbled upon the rent-to-rent (R2R) model—a strategy that would radically transform his financial trajectory.
Today, Simon has completed over 70 rent-to-rent deals, both in HMOs and serviced accommodation (SA), and owns properties funded entirely by the cash flow from controlling properties he doesn’t own. His talk at the HMO Summit 2023-24 was a high-energy, brutally honest session on why controlling cash-generating assets beats owning them outright—for at least the first phase of your investing career.
The Billionaire’s Blueprint: Control Over Ownership
Simon kicked off with an inspiring story from the Maldives, where he learned of a Malaysian billionaire who leased a lagoon (not an island), developed four manmade islands, and subleased two of them to Ritz-Carlton. This, Simon said, is billion-dollar rent-to-rent—an extreme version of controlling assets to cash flow them at scale. The takeaway: you don’t need ownership to generate wealth—you need control and creativity.
This set the tone for Simon’s own approach. Rent-to-rent allowed him to build a property portfolio without the massive capital outlay required for purchasing. His strategy? Control for cash flow first, then buy later when the cash reserves make ownership less risky.
Cash Flow vs. Capital Appreciation: What Matters More?
Throughout his talk, Simon addressed the age-old debate: should you chase cash flow or capital growth? Most investors lean toward owning assets for long-term appreciation, but Simon challenged this assumption:
- Appreciation is often theoretical. Most landlords don’t sell, so the wealth stays on paper.
- Refinancing is slow. Even the best BRRRR (Buy, Refurbish, Refinance, Rent, Repeat) strategy takes months to realize value.
- Cash flow is immediate and usable. It pays for your lifestyle now—not 20 years from now.
He emphasized that a rent-to-rent business generating £20,000/month could easily be valued and sold just like a traditional business. That’s an asset in itself, and one that gives you both speed and lifestyle.
Control Without Ownership: Better ROI, Lower Risk
Simon illustrated a key point using a powerful example: two properties side by side, each generating £1,000/month in income. One requires a £197,000 investment to buy; the other, just £10,000 to control via R2R. The returns? Identical. So why tie up so much capital in ownership when you can control multiple properties for the same amount and multiply your cash flow?
He acknowledged the emotional satisfaction of owning, but for him, it’s all about Return on Effort and Return on Time. Controlling more with less makes sense—especially early in your investing career.
The Problem with Debt, JV Partners, and Complexity
One of the most honest parts of Simon’s talk was his reflection on debt and joint ventures. While the property world often celebrates “good debt” and JV partnerships, Simon argued that simplicity is underrated:
- Too many JV partners = too many moving parts.
- Too much debt = sleepless nights.
- Banks can call in loans. JV partners can change their mind.
Instead, he recommends reinvesting your R2R profits into assets you fully control, ideally with minimal debt and no outside interference. His own preference is to JV only with his wife—a setup that aligns incentives and reduces conflict.
Exit Flexibility and Peace of Mind
A little-discussed benefit of R2R is flexibility. If you need to exit a property you control, a simple 2-month notice period does the job. Contrast that with selling a mortgaged property, which can be expensive, slow, and emotionally taxing. The optionality of R2R means you’re less exposed during downturns or personal crises.
Development Headaches vs. Rent-to-Rent Speed
Simon also shared a cautionary tale about a £1.2 million development that turned into a two-year nightmare due to planning delays, restrictive covenants, and a bankrupt builder. The project drained time, energy, and capital.
In contrast, R2R deals can be secured, set up, and cash-flowing within days or weeks. Year one of his R2R journey saw him onboard 20 deals and earn £20K/month in profit—nearly impossible with developments.
The Rent2Rent 2.0 Model: The Best of Both Worlds
Simon’s current approach? Something he calls Rent2Rent 2.0—a hybrid strategy where he controls properties for high cash flow, systemizes the operations, and uses the profits to buy long-term assets slowly and safely. He’s now on properties #9 and #10, almost entirely funded through rent-to-rent cash flow.
This method allows him to live well today while building generational wealth for tomorrow. No heavy reliance on OPM (Other People’s Money), no stress from joint ventures, and plenty of room to enjoy the journey.
Final Lessons: Cash Flow First, Lifestyle Always
Simon’s closing message was both motivational and strategic:
“Think about where you were when you started and what your goal was. You’ve got to improve your life today. You owe it to yourself and your family.”
He reminded attendees that the property game should be enjoyable. If you’re only investing for a retirement 30 years away, what happens if you never make it there?
Instead, focus on building a lifestyle you can enjoy today. For Simon, rent-to-rent made that possible—and it might just do the same for you.
Rent-to-rent is not a stepping stone. Done right, it’s a powerful business model in its own right. It offers speed, scale, flexibility, and cash flow—everything a modern investor needs to build wealth and enjoy the process. If you’re looking to grow your property portfolio without tying up hundreds of thousands in deposits and debt, Simon Smith’s model is one to seriously consider.
