Marine engineer turned property entrepreneur Reuben Wincott sailed through some choppy waters before becoming financially free. He lost money in a joint venture which went badly wrong until he managed to turn around his fortunes. Reuben now earns £6,000 to £7,000 a month from a mixed portfolio including serviced accommodation. He also reached the semi-finals of The Eviction 2024, the Apprentice-style competition for budding investors hosted by Samuel Leeds.
‘Rent-to-rent model is a golden goose’
In his old job, Reuben was contracted to repair and rebuild boats, as well as sail them. His work took him all over the world, mainly to Europe and also the Caribbean.
Eventually, however, Reuben tired of living out of suitcases and decided he wanted to make a full-time living instead out of investing in bricks and mortar.
He already had some experience, having flipped houses with his father since the age of 15 in the Gosport area of Hampshire. Together they would do up a property and then either sell or rent it out.
It was when Reuben was renting out one of his dad’s places which he put on Airbnb, hoping to get bookings for a couple of nights a month, only for it to achieve 90 per cent occupancy.
“I thought this is a golden goose. I’ve found a business model here, renting off landlords and then renting them out on Airbnb.”
Keen to find out more about the strategy, he scrolled through YouTube and immediately Samuel Leeds’ videos came up. That led to Reuben attending one of Samuel’s £1 crash courses which opened his mind to a ‘new way of thinking and a new way of life.’
The course gave Reuben an overview of how to source properties, find landlords and assess potential deals. He was also impressed with the energy in the room and so signed up for a course on rent-to-rents before later registering on the academy.
After joining the year-long training programme he embarked on a joint venture in January 2024 to convert a three-bed property in Sheffield into a four-bed HMO.
It was miles away from where Reuben lives in Portsmouth, but he went ahead with the project despite that, agreeing to split the profits.
“I was working abroad at the time. I thought I'll JV with someone. I'll put in the money. They'll do the work and then we refinance at the end, and I'll get all my money back in theory.”
In hindsight, he admits it was stupid. He was ‘hands-off’ and failed to keep up to date with what was happening with the work. Then the builder fell sick which hindered progress.
Finally, Reuben called time. “I had to give the JV partner a settlement to get him off the project and for me to take back full ownership. It was a nightmare.”
After paying the builder for his work, Reuben found himself picking up his tools, ‘grafting’ 12 to 14 hours a day for about three weeks to complete the scheme.
The house is now fully tenanted, but he overshot his budget and is still waiting to obtain the refinance. Once that comes through, he expects to pull out around £135,000.
Whilst the 29-year-old just about pulled around his investment, there were lessons to be learned. One was to ensure he had a ‘bulletproof contract’ incorporating performance targets in future. Had Reuben had such a contract, he could have avoided the settlement.
The distance between his home and his investment property has also proved to be a problem when repairs have been needed which has been a common occurrence.
“We've been having some issues with the boiler lately and I've had to pay a plumber £200 every time to go round there, whereas if it was close to me I would just go there and repressurise it to fix the issue.
“So, investing somewhere local to your home is key.”
Diversifying the portfolio creates a ‘fast’ and ‘slow’ pound
By investing in Sheffield, Reuben ignored the general advice of his trainers to choose a patch within an hour of his home where property is cheap. As he lives in the south, where prices are high, he felt he had no choice but to head north instead.
He also invested in a pub in Wales. That was even more of a wild card,’ than his Sheffield house, he confesses. More recently, however, he has stayed local, having realised with the benefit of his education that there are other ways of funding acquisitions in expensive areas.
“I already had one buy-to-let in Gosport and then I'm now about to buy another two Southampton way, so not far from Portsmouth.”
What changed for the entrepreneur was learning that, in taking on HMO conversions, bridging and finance companies will lend the entire cost of the development.
“I've always been, buy for cash. So now I’m utilising bridging finance to do some deals local to me.”
Another academy member recommended a broker who has been helping him to secure the finance.
One of the houses Reuben is about to complete on is in Eastleigh, near Southampton. The purchase price is £262,000, with the refurbishment projected to cost about £180,000 which will be funded through a bridging loan.
Reuben will put in about £130,000 from his savings. It is lot of cash to be putting in, he concedes, but the rewards promise to be high. He is aiming to achieve an end value of £650,000 once it has been converted into a seven-bed house share.
His plan is to obtain a commercial valuation and then remortgage it, leaving in about 25 per cent of his money. The rooms will also be rented out, producing an anticipated profit of £1,800 to £2,000 per month.
At the same time, the businessman has been using the rent-to-HMO strategy to ramp up his profits, targeting properties in and around Portsmouth, and Aldershot.
“This has been eye-opening [seeing] how much cash flow you can get from such a low investment. On the rent-to-HMO model we’re doing an average £5,000 to £10,000 per one for set-up and these are all cash-flowing £800 to £1,500 profit a month.”
Compared to a buy, refurbish, refinance project which can take upwards of a year to bring to fruition, the rent-to-HMO method gives the investor a quick way of making money. The disadvantage is not actually owning the asset.
For that reason, Reuben is concentrating his efforts on diversifying his portfolio to create a ‘fast pound’ which replaces his salary and a ‘slow pound’ for building generational wealth.
‘A lot of people have £50,000 and don’t know what to do with it’
When Reuben took up his training, he had £150,000 at his disposal, plus £70,000 in shares. It was a decent pot of money to invest and recycle into other deals.
The principle behind the buy, refurbish, refinance strategy is that the entrepreneur improves a property and then remortgages it to its new value to extract capital.
However, if there is a delay in obtaining the refinance it can prevent the investor using that money to move on to their next BRR project.
As Reuben has been waiting for the mortgage to come through on his Sheffield property, he fears it could scupper his Eastleigh acquisition. So, as a ‘fail-safe,’ he has been raising finance for it.
The first step when approaching an investor is to make them believe in you, he says. “When I was younger nobody believed in me. It's only after compounding quite a few years of experience that I can raise money quite easily now.”
Reuben, who went full-time into property in May 2024, finds investors through frequenting ‘high ticket places’ like marinas and golf courses where the rich congregate, as well as using his network. For his Eastleigh undertaking, a friend has agreed to lend him £70,000.
“There are a lot of people who have got £50,000 in the bank and don't know what to do with it.”
Since posting on Instagram about his rent-to-rents many people he’s met over the years have reached out to him. This has also happened when going to the gym.
“I've had people come up to me saying I saw your post. I've got £20,000. What do you think I should do with it? Next minute you’ve got a pool of five £20,000s. You give them ten per cent return on investment. They're happy and you've got £100,000.”
His portfolio includes three rent-to-HMOs, which he took on with his business partner Jacques Bridges, and three SAs of his own. They are also due to collect the keys to another two by the spring of 2025.
The rent-to-rents make upwards of £5,000 a month in total. Of that amount, £3,500 comes from the rent-to-HMOs, with the others making Reuben around £2,000 to £3,000. That alone is the equivalent of an average full-time salary, he points out.
Reuben met Jacques at one of the academy dinners. Both men are from Gosport and so they teamed up. Reuben already had his SAs, whereas Jacques prefers HMOs. Consequently, they have been homing in on that as their strategy, finding properties through agents mainly.
The pair look for houses with plenty of bedrooms, scanning the windows of estate agencies for suitable properties.
Reuben always wears a suit, walking in off the street without an appointment if he identifies a property that might work for him. He explains that he has a professional renting company housing contractors in the marine industry, and that due to increased demand his business is seeking to expand its portfolio.
Taught to lead with questions, he tells his story confidently with the aim of securing a viewing.
Often the houses he finds have previously been student lets which need a facelift.
“Since they've built all these purpose-built student blocks, the student HMO market is dying and they're not converting them for professionals. So, we'll go on SpareRoom to find out what the average room rents are.”
He and his partner then multiply that figure by the number of rooms in their target property to work out the potential revenue from it, allowing £100 per tenant for bills.
Ideally, it needs to produce a positive cash flow even if one room is empty or at least break even in the worst-case scenario. Their goal is to achieve a profit of more than £700 a month. They control a six-bed HMO, all with en suites, which makes £1,500 per month, while some of the smaller properties generate around £800 a month.
‘The Eviction was intense, gruelling – and rewarding’
The Eviction proved to be an enriching experience for Reuben, although it was ‘intense’ and ‘gruelling,’ working up to 18 hours a day to complete real-life investment challenges.
The ‘key takeaway’ for him was pursue one course of action until successful. He and his two teammates made more than 200 calls one day and earned £51,000 through selling deals.
Now he is hoping to take on more HMOs as his journey progresses, having also learnt lessons from the purchase of a disused pub in Wales with his business partner. They wanted to convert it into apartments but cut their losses after delays getting planning permission.
Each of them put in £40,000 to buy the pub but have now accepted an offer on it, although they will lose about £5,000 overall.
The training and mentorship provided by the academy has been crucial in enabling Reuben to expand his knowledge, get advice on deals and obtain contracts.
“I was already clued up on refurb costs, but I had no idea about commercial valuations and refinancing. The mentorship was one of the reasons I joined the academy.
“When you’re going to start investing your own money it’s scary, so I needed some sort of guide and that’s been exactly what I got.”
Reuben’s tips
- To find investors go to places which attract wealth. I wouldn’t say go to a marina if you don’t know anything about boats.
- If you know an experienced investor, ask them for feedback on your deal and run the numbers past them. They might offer you funding without directly asking for money which could make them feel awkward.
Samuel Leeds
“It’s been great working with Reuben and having him on The Eviction. He’s smart. He works very hard. He’s got natural get-up-and-go and I wish him nothing but continued success.”
