For many aspiring property investors, the biggest challenge is knowing where to start.
That was exactly the position Simon Dolman found himself in before entering the world of property investing. Today, Simon operates seven rent-to-rent serviced accommodation properties across Northampton, Milton Keynes and Dartford, while also expanding into lease options, hotel deals and property management.
His journey is a powerful example of what can happen when an entrepreneurial mindset, networking and consistent action come together.
Watch Simon’s Full Property Success Story Here
From Landscaping Business to Property Investor
Before entering property, Simon already had strong entrepreneurial instincts.
Growing up in Northampton, he worked within his family’s landscaping business after previously working in commercial vehicle sales. Alongside this, Simon helped scale a self-storage business with around 50 storage containers, generating recurring income.
Even from a young age, entrepreneurship came naturally.
“Even at school, I’d be selling cans of Coke and chocolate bars.”
Like many successful property investors, Simon’s background in sales and business gave him the confidence to communicate with people, build relationships and identify opportunities.
However, property investing had always interested him.
How Simon Discovered Samuel Leeds
Simon first came across Samuel Leeds Academy after his wife discovered Samuel Leeds online through YouTube and social media.
Together, they attended one of Samuel’s low-cost property training events in London.
What stood out immediately was the practical approach.
Rather than teaching theory alone, Samuel actively demonstrated how to analyse deals, speak to agents and structure opportunities in real time.
That hands-on training gave Simon the confidence to move quickly.
The First Rent-to-Rent Deal
After attending the Deal Selling course, Simon secured his very first serviced accommodation opportunity within weeks.
Interestingly, it came through networking.
Originally attending networking events to grow his landscaping company, Simon began building relationships with landlords, developers and business owners. Over time, these conversations naturally evolved into property opportunities.
His first rent-to-rent serviced accommodation property was already operating successfully before he took it over, allowing him to see real figures and reduce risk.
Within a week of taking over the property, he secured a guest booking lasting several months.
That momentum quickly snowballed.
Scaling to Seven Serviced Accommodation Properties
Today, Simon operates seven serviced accommodation units generating approximately £13,500 per month in turnover.
His properties mainly serve contractors and working professionals looking for a more comfortable alternative to hotels.
Simon explains that serviced accommodation offers several advantages over traditional buy-to-let investing:
- Higher cash flow potential
- Greater control over property condition
- Flexible guest stays
- Reduced long-term tenant issues
- Strong demand in key working areas
He also highlights the importance of choosing locations with proven accommodation demand.
“If there’s a hotel there, they’ve already done the market research for you.”
This strategic thinking has helped Simon expand confidently into multiple locations.
Expanding Into Lease Options and Hotel Deals
Alongside serviced accommodation, Simon is now progressing into more advanced property strategies.
One of his current projects involves a lease option agreement on a property in Northampton, allowing him to control the asset without purchasing it outright today.
He is also working on a hotel acquisition opportunity through a joint venture partnership.
These strategies demonstrate an important principle taught within the Samuel Leeds Academy:
You do not always need large amounts of money to control profitable property deals.
The Power of Property Networking
One of the biggest themes throughout Simon’s journey is networking.
Interestingly, Simon believes some of the best networking opportunities happen outside traditional property events.
Many of his serviced accommodation opportunities came through general business networking groups, where landlords and business owners often have properties but lack the time or expertise to manage them effectively.
By focusing on helping people rather than aggressively pitching deals, Simon built trust naturally.
That approach continues to create opportunities today.
Building Financial Freedom Through Property
Despite already running successful businesses, Simon sees property as the vehicle that creates long-term freedom.
His ultimate goal is not simply financial gain, but more time with family, greater flexibility and the ability to travel more frequently.
With five children and multiple businesses, building systems and recurring income has become increasingly important.
This is one reason serviced accommodation and management contracts appeal to him so strongly.
Is the Samuel Leeds Academy Worth It?
For people researching whether the Samuel Leeds Academy is worth joining, Simon’s story highlights several key benefits:
- Access to practical property training
- Networking opportunities
- Mentorship and accountability
- Exposure to multiple property strategies
- A supportive community environment
- Confidence to take action quickly
Like many successful students, Simon’s results came from combining education with consistent implementation.
Simon’s Advice for New Property Investors
Simon’s advice for beginners is simple:
“Stop worrying about what other people think and just get started.”
He also emphasises the importance of helping people, creating win-win opportunities and consistently putting yourself into rooms where opportunities can happen.
For aspiring investors interested in serviced accommodation, rent-to-rent or building a property business from scratch, Simon’s story proves that progress often starts with a single conversation.
Want to Learn Property Investing?
Discover upcoming training events, property strategies and success stories through Samuel Leeds' official website.
You can also explore more real-world case studies on the Samuel Leeds Success Stories Page.
