Property Developers Playbook

In this premiere episode of Property Developers Playbook, hosts Kieron Shepherd and Jonathan Stobbs introduce themselves, their backgrounds, and what inspired them to launch this podcast. With over 70 completed dwellings and 100 more in the pipeline, Kieron (a construction veteran) and Jonathan (an accountant-turned-developer) share how their complementary skillsets shape their approach to property development.

KEY TAKEAWAYS

Kieron brings construction know-how; Jonathan brings financial acumen—together they demystify the property development process.

The podcast aims to help listeners avoid common (and costly) mistakes by sharing hard-earned experience.

The show will cover a comprehensive, cyclical development model—from sourcing sites to planning exits.

Jonathan and Kieron explain how development offers scalability, tax advantages, and better risk-reward balance.

Property development is a team sport; knowing your strengths and finding complementary partners is critical.

BEST MOMENTS

“Property development is not a solo sport.”

“You need to be the conductor of the orchestra—but you’ve also got to bring something to the table."

“We’ve learned a lot along the way—some of it the hard way.”

“There are huge tax advantages in property development compared to buy-to-let.”

“Do what you love. Don’t just chase the quick buck.”

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.

https://www.facebook.com/jonathan.stobbs.7/

https://www.linkedin.com/in/jonathanstobbs/

https://www.facebook.com/kieron.shepherd.73

https://www.linkedin.com/in/kieron-shepherd-83b979aa/

In this episode, we dive deep into the nuanced world of adaptability, leadership, and innovation with a guest who straddles multiple disciplines—from elite military operations to high-level coaching. Jonathan and Kieron explore how individuals and organisations can build adaptive capacity, leverage feedback loops, and thrive under pressure. If you're navigating change, leading teams, or pushing the limits of your own performance, this episode offers a compelling mix of strategy, science, and storytelling.

KEY TAKEAWAYS

While online platforms like Rightmove and Zoopla can be useful, the most valuable opportunities often come from building relationships with local commercial agents, architects, planning consultants, and even accountants.

Rather than casting a wide net, the hosts recommend focusing on a specific geographic area you know well—your “goldmine area.” This allows you to leverage local knowledge, build relationships, and manage developments more efficiently, especially if you want to balance work with family life.

Beyond traditional listings, the episode covers alternative sourcing methods such as direct-to-vendor letters, using land-sourcing software like Nimbus Maps, networking with professionals, and even following up on unsold auction properties.

Finding a potential site is only the beginning. Jonathan and Kieron stress the importance of quickly assessing whether a deal is viable by running the numbers, understanding build costs, and factoring in hidden expenses.

Property development is not a solo endeavour. Success depends on assembling the right team—planning consultants, architects, contractors, and more.

BEST MOMENTS

“Adaptability is not something you’re born with—it’s something you train like a muscle.”

“The best don’t rise to the occasion, they sink to the level of their systems.”

“Feedback is how nature evolves; if we don’t build it into our lives, we stagnate.”

“Stress isn’t toxic by default—it’s information. It’s how you respond that determines the outcome.”

“Leadership isn’t about having the answers—it’s about holding the space for better questions.”

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.

https://www.facebook.com/jonathan.stobbs.7/

https://www.linkedin.com/in/jonathanstobbs/

https://www.facebook.com/kieron.shepherd.73

https://www.linkedin.com/in/kieron-shepherd-83b979aa/

Property Developers Playbook is your go-to podcast to the world of property development and investment. Hosted by Jonathan Stobbs and Kieron Shepherd, who both have experience as developers and as main contractors, this podcast dives into the strategies, challenges, and rewards of real estate development. 

Whether you're a contractor looking to transition into development or an investor looking to scale, each episode provides actionable insights, dos and don’ts, and first-hand experiences from those on the ground. Join us as we interview top developers, tackle common pitfalls, explore innovative solutions, and discuss the mindset required to thrive in property development.

Property Developer’s Playbook is more than just advice; it’s a blueprint for unlocking your potential in property development. Tune in to start building your knowledge, confidence, and your success.

ABOUT THE HOSTS

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.

https://www.facebook.com/jonathan.stobbs.7/

https://www.linkedin.com/in/jonathanstobbs/

https://www.facebook.com/kieron.shepherd.73

https://www.linkedin.com/in/kieron-shepherd-83b979aa/

https://www.propertydevelopersplaybook.co.uk/