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In this episode, Kieron flies solo while co-host Jonathan takes a break to deliver an honest, candid look at the uncomfortable reality of property development: failed deals, lost capital, and unexpected setbacks. Kieron shares behind-the-scenes stories from his own portfolio, including a promising five-house development that unraveled due to planning restrictions and a high-margin site he had to walk away from when investors capped their funding.
KEY TAKEAWAYS
Setbacks Are Tuition, Not Failure: Losing time, energy, or money on a deal isn't a personal failure; it's an essential part of the learning curve that shapes a sharper developer.
Stick Strictly to Your Numbers: Never inflate Gross Development Value (GDV) or squeeze contingency buffers just to make an unprofitable deal look viable on paper.
Avoid Emotional Attachment: Falling in love with a site design or layout clouds objective decision-making; development must remain a disciplined, factual process.
Verify Planning Constraints Early: Always conduct independent due diligence on planning permissions and redline boundaries rather than relying solely on third-party assumptions.
Know When to Walk Away: Whether due to tight timelines, investor limits, or changing market conditions, having the discipline to say "no" saves you from catastrophic losses down the line.
BEST MOMENTS
"Don't see this as a failure... it's all learning."
"The deal you lose makes room for the one you were actually supposed to do."
"Property development isn't about winning every deal; it's about surviving long enough to win the right ones."
"If it doesn't work, it doesn't work... don't try to make the deal work."
"You've got to brush yourself off, get back on the horse, and just go again."
YOUTUBE CHANNEL
https://www.youtube.com/@propertydevelopersiq
HOST BIOS
Jonathan is a property developer and entrepreneur with a background in finance and construction. Originally from South Africa, he holds degrees in Accounting and Auditing and relocated to England in 2003. He gained financial and operational experience at firms such as RSM, Prudential, and Baker Tilly before transitioning into property. Since 2014, Jonathan has managed major commercial-to-residential conversions and new build developments, particularly across the South West. His analytical mindset and on-the-ground experience help listeners navigate the property world with confidence.
Kieron is a construction expert and entrepreneur with over 20 years of industry experience. Starting as a mason, he went on to found Shepherd Construction in 2012, delivering projects across both the public and private sectors. From extensions to luxury new builds, Kieron has earned a reputation for quality, precision, and strong leadership. As Managing Director, he’s involved in every stage—from design to delivery—offering a no-nonsense, deeply practical perspective to anyone looking to build with success.
OUR SOCIALS
https://www.facebook.com/jonathan.stobbs.1979/
https://www.linkedin.com/in/jonathanstobbs/
https://www.instagram.com/jonathan.stobbs/
https://www.facebook.com/kieron.shepherd.73
https://www.linkedin.com/in/kieron-shepherd-83b979aa/
https://www.instagram.com/kieron__shepherd/
https://www.propertydevelopersplaybook.co.uk/
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