Property Developers Playbook

Jonathan Stobbs & Kieron Shepherd
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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.

  1. Which Contract is Right for Your Development: JCT Contracts and The Alternatives

    5 DAYS AGO

    Which Contract is Right for Your Development: JCT Contracts and The Alternatives

    In this episode, Jonathan and Kieron dive deep into the world of construction contracts, focusing on the industry-standard JCT (Joint Contracts Tribunal) and the more collaborative NEC (New Engineering Contract). They discuss why having a legal framework is essential for managing risk, cost, and timelines in property development, and also share highlight the importance of thorough administrative processes and clear scopes of work to avoid disputes.  KEY TAKEAWAYS The JCT is the most common standard form of contract in UK construction, widely recognized by contractors, lenders, and solicitors for its clear structure. You cannot simply reuse a JCT contract; each document has a unique ISBN and must be purchased and filled out specifically for each new project to be legally valid. Under a D&B contract, the contractor takes responsibility for the design team, which can relieve pressure on the developer regarding aesthetic and technical decisions. A contractor should never perform work outside the original scope without a formal, documented instruction from the contract administrator, as verbal agreements can lead to unpaid disputes. While JCT is standard, the NEC contract offers a more collaborative approach and can allow for more flexible payment terms, such as deposits or down payments. BEST MOMENTS "Effective what you're agreeing is what happens in worst case scenario. Who will effectively be deciding the tribunal element of who's in the right in terms of how you move forward." "Don't try to trip each other up. You're working as a team. It’s not about finding loopholes." "Contracts allocate risk; they don't remove it. They just try to mitigate the risk as much as possible for both parties." "Poor administration causes more issues than poor wording. It needs to be administered correctly." 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.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/ Book your seat now on our 3 day live event Property Developers Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    39 min
  2. Why Traditional Tendering is Broken: Disrupting Contractor Procurement

    26 JAN

    Why Traditional Tendering is Broken: Disrupting Contractor Procurement

    Today, Jonathan and Kieron challenge the industry standard of traditional tendering. Speaking from both developer and main contractor perspectives, they dissect the inefficiencies, hidden costs, and frustrations of the ‘cheapest wins’ mentality. Jonathan and Kieron propose a more collaborative, transparent approach that prioritises realistic budgeting, early engagement, and building long-term partnerships over competitive tension. KEY TAKEAWAYS Traditional tendering often rewards unrealistically low bids that lead to cost overruns later. The lowest initial price rarely equals the best final value. Sharing your actual budget and proof of funds early builds trust and saves everyone time. Treat contractors as partners, not adversaries. Don’t just look at the price on a spreadsheet. Interview potential contractors (via Zoom or in person) to gauge compatibility, experience, and honesty. To get accurate apples-to-apples comparisons, provide a bill of quantities rather than just raw drawings. This ensures everyone is pricing the same scope of work. Involve main contractors and quantity surveyors during the design phase. Their input on buildability and material costs can prevent expensive redesigns later. BEST MOMENTS "The lowest initial price rarely equals the best final value." "Treat contractors with respect and intelligence. If you start that conversation of allowing that contractor to ask those really important questions, we want the business." "You don't win at construction by buying the cheapest. You win by buying certainty." "Cheap isn't what you want. That level of cheap is you just asking for problems. We know our product." "It's about building long-term partnerships. If you do something well with a developer or customer or main contractor, you're going to use them again." 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.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/ Book your seat now on our 3 day live event Property Developers Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    48 min
  3. Why You Don’t Always Need to Build

    19 JAN

    Why You Don’t Always Need to Build

    In this episode, Jonathan and Kieron debunk the common myth that being a property developer requires you to actually build houses. They break down the full development lifecycle, from sourcing land to securing planning permission, and explain why ‘building’ is actually just one of several potential exit strategies. The duo discuss the benefits of exiting early, such as selling sites with planning permission to reduce risk, and why the old ‘rule of thirds’ for calculating profit no longer applies in today’s market.  KEY TAKEAWAYS Construction is often the last stage of development, and you do not have to undertake it to be successful; many developers specialise solely in sourcing land and achieving ‘planning gain’ before selling the site. While building out a site typically offers the highest profit margin, it also carries the most risk regarding construction costs and market changes. Selling a site with planning permission is a ‘shorter game’ that allows you to realise profit sooner with less exposure. The old rule of thumb (33% land cost, 33% build cost, 33% profit) is outdated. A more realistic breakdown today is often 20% purchase price, 50% build costs, 20% profit, and 10% finance/anomalies. When working with investors, treat the planning approval stage as a checkpoint. This gives everyone the option to decide whether to sell the site and take the profit now or proceed to the construction phase. Successful development requires the ability to pivot. You might intend to build, but personal circumstances or market conditions might make selling the site (‘flipping’) a smarter financial move at the time. BEST MOMENTS "In reality, building is often the last stage in property development. There are multiple exits before you actually get to start building." "Some people just specialise as property developers in planning gain. They find a piece of land, sort out the planning, and then sell it on to another developer." "Building is ultimately just one method of extracting the value from the site." "A bird in the hand is better than two in the bush. Cash in the hand is better than cash in the land." "People used to do the whole 'third, third, third'. We don't do that anymore. It's probably a bottom line 20% conservative on your profit." 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/ https://www.propertydevelopersplaybook.co.uk/ Book your seat now on our 3 day live event Property Developers Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    27 min
  4. Alter Architects - Designing for Developers. Architecture That Builds The Purpose of Place

    12 JAN

    Alter Architects - Designing for Developers. Architecture That Builds The Purpose of Place

    Today, Jonathan and Kieron welcome Grant Shepherd from Alter Architects. Grant shares his journey from landscape designer to architect, detailing his experiences working with various property developers and the importance of collaboration in the industry. They discuss the nuances of architectural design, the significance of effective communication between architects and developers, and the challenges of balancing creativity with budget constraints. KEY TAKEAWAYS Successful property development relies on effective collaboration between architects and developers. Understanding each other's perspectives and terminologies can lead to better project outcomes. Decisions made in the early stages of a project significantly impact the final build cost and overall success. It's essential to assemble the right team and establish clear communication from the outset. Creating spaces that foster community engagement and cater to the needs of residents, especially youth, is vital. Good architecture should not only focus on aesthetics but also on enhancing the quality of life for users. Familiarity with local and national planning policies is critical for architects. This knowledge helps navigate the complexities of securing planning approvals and ensures that projects align with regulatory requirements. Efficient layouts and thoughtful design can add value to a project. Architects should focus on maximising space and functionality while being mindful of budget constraints, ensuring that designs are both practical and appealing. BEST MOMENTS "For us, that was second nature. We grew up with a father who was very creative and he was a landscape gardener." "I think the key thing is that what we come across a lot is that developers don't want to do measured surveys." "I think the critical thing is that those buildings are good returns." "You are the maker of dreams. You are turning their ideas and wishes and wants into reality." VALUABLE RESOURCES https://alterarchitects.co.uk/ https://www.linkedin.com/in/grant-shepherd-arb-maarch-5a79a889/ 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/ https://www.propertydevelopersplaybook.co.uk/ Book your seat now on our 3 day live event Property Developers Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    56 min
  5. Top 10 Challenges in Property Development - Part 10: Mindset and Resilience

    5 JAN

    Top 10 Challenges in Property Development - Part 10: Mindset and Resilience

    In this episode, Jonathan and Kieron delve into the often-overlooked challenge of mindset in property development. As they wrap up their mini-series on the Top 10 Challenges developers face, they emphasise the importance of resilience, mental health, and the ability to navigate pressure in the industry. The duo discusses the significance of setting goals, managing risks, and the value of having a supportive team and mentors. KEY TAKEAWAYS Success in property development heavily relies on having a positive mindset and the ability to navigate pressure and challenges. Developers must cultivate resilience to handle the stresses and uncertainties of the industry. Property development involves managing and mitigating risks rather than avoiding them. It's essential to assess risks for each development and make calculated decisions to move forward. Building a strong team and network is crucial. Collaborating with experienced professionals, mentors, and peers can provide support, guidance, and different perspectives, which are vital for overcoming challenges. Developers need to prioritise their mental and physical health. Taking breaks, engaging in hobbies, and maintaining a healthy lifestyle can help manage stress and prevent burnout. Each development project serves as a learning opportunity. By reflecting on past challenges and successes, developers can improve their decision-making and approach future projects with greater confidence. BEST MOMENTS "You don't build houses before you build resilience." "Success in development isn't about avoiding pressure. It's about learning to perform under it." "It's about how you deal with setbacks. There's always going to be a solution." "You need to have that kind of resilience. If something goes wrong, it's how can you bounce back from that quickly." "You can't just stick your head in the sand because that's never going to attract investment." 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/ https://www.propertydevelopersplaybook.co.uk/ Book your seat now on our 3 day live event Property Developers Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    27 min
  6. Top 10 Goal-Setting Tips for Property Developers in 2026

    29/12/2025

    Top 10 Goal-Setting Tips for Property Developers in 2026

    In this final episode of 2025, Jonathan and Kieron reflect on the lessons learned from the past year, and discuss their goals for 2026. They explore various goal-setting strategies, including the SMART framework and the significance of behaviour goals, while also addressing the challenges of instant gratification in today's society. They also share insights on effective networking, building a strong team, and the necessity of reviewing progress regularly. KEY TAKEAWAYS Emphasising the importance of setting realistic and achievable goals, particularly in property development, while also recognising the need for flexibility and adaptability in timelines. Focusing on activity-based goals, such as analysing a certain number of sites per week and attending networking events, to drive results rather than solely concentrating on outcome goals. Highlighting the significance of building a strong network and team, including finding the right professionals to collaborate with, which can enhance the success of property development projects. Encouraging regular reviews of progress and adjustments to goals, as well as celebrating small wins to maintain motivation and recognise achievements throughout the year. Advocating for a life-work balance where personal life takes precedence, and work is structured around it, ensuring that enjoyment and fulfillment are prioritised in both professional and personal endeavours. BEST MOMENTS "2025 taught us a lot. It's kind of taking those lessons and making sure we don't make the same mistakes, but actually growing and scaling from that." "You need to have certain activity goals that you need to be doing, analysing 10 sites per week to be able to submit a certain number of offers per month." "You want to be a yes man, but this is also quite a hard thing because people don't know, until you know, you don't know how far is too far." "Celebrate your small wins. A lot of people don't celebrate. We do a fist bump and then we kind of move on, rather than actually saying, okay, let's reward ourselves for doing something amazing." "The exit of a development should be also the start of the development. You should be reviewing each stage at every stage." 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/ https://www.propertydevelopersplaybook.co.uk Book your seat now on our 3 day live event Property Develoeprs Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    27 min
  7. 2025 in Review: Our Biggest Wins, Mistakes & Lessons

    22/12/2025

    2025 in Review: Our Biggest Wins, Mistakes & Lessons

    Today, Kieron and Jonathan take a look back at the challenges, lessons, and successes of their 2025 as they approach the Christmas season. They discuss their ambitious goals for the year, including various development projects such as Woodlands Ponsanooth, St. James Court, and Luxstowe House, while sharing insights on navigating the complexities of property development. The duo highlights the importance of building strong relationships with investors and landowners, as well as the value of collaboration in overcoming obstacles. They also touch on the launch of their podcast, plans for a Property Developers Bootcamp, and the expansion of their media company, POM Media. KEY TAKEAWAYS It's important to take time to reflect on the past year, assessing both successes and challenges. This practice can provide valuable insights and help in setting future goals. Managing multiple development projects can be complex, especially when dealing with issues like planning, financing, and unforeseen complications such as contamination testing. Patience and adaptability are crucial. Strengthening relationships with existing investors and building new ones has been beneficial. Engaging with investors through site visits can help validate project potential and foster trust. The launch of new initiatives, such as a podcast and a property developers bootcamp, has expanded outreach and provided additional resources for aspiring developers. Collaboration and leveraging team skills are essential for growth. The construction industry has faced challenges due to economic uncertainty and market stagnation. Staying positive and proactive in building relationships and seeking opportunities is vital for navigating these conditions. BEST MOMENTS "2025 was a year full of challenge, uncertainty, opportunity, and growth. Today we're breaking down how it was for us and what we've learned from it." "The bloody refinancing process has taken its toll, hasn't it? It's taken ages, hasn't it? Everything just seems to take a lot longer." "It's a way of trying to work out how to make the site easy to build. Just because something's got planning doesn't mean it's buildable." "One of the lessons was, try not to change the goalposts midway. It'll be a lot easier." "If you don't reflect, you don't think of it like that, do you? Lots of homes we're building." 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/ https://www.propertydevelopersplaybook.co.uk/ Book now onto our Property Developers Bootcamp https://www.propertydevelopersiq.co.uk/pdblive

    26 min
  8. Top 10 Challenges in Property Development - Part 9: Dealing with NIMBYs & Community Engagement

    15/12/2025

    Top 10 Challenges in Property Development - Part 9: Dealing with NIMBYs & Community Engagement

    Today, Jonathan and Kieron delve into the ninth challenge property developers face: dealing with NIMBYs (Not In My Backyard), community and stakeholder engagement, and turning objections into opportunities. They discuss the importance of proactive community engagement, emphasising that it's not just a tick-box exercise but a crucial part of the development process. They highlight the value of early consultations with local councils and stakeholders to mitigate potential conflicts and foster goodwill. KEY TAKEAWAYS Engaging with the community early in the development process is crucial. Developers should proactively communicate their plans to local residents and stakeholders to mitigate objections and foster goodwill. Developers need to comprehend the psychology behind NIMBY (Not In My Backyard) sentiments. Many objections stem from emotional attachments to views or local character, and addressing these concerns can help in gaining community support. By holding public consultations and providing clear information about developments, developers can manage the narrative surrounding their projects. This proactive approach helps counter negative speculation on social media and builds a positive perception. Utilising visual aids such as CGI and 3D walkthroughs can help residents better understand proposed developments. This transparency can alleviate fears and misconceptions about how a project will impact their surroundings. Developers should communicate the broader benefits of their projects, such as affordable housing and public realm improvements. By showcasing how developments contribute to the community, they can shift the focus from objections to positive outcomes. BEST MOMENTS "Objections can derail timelines, you know, planning approvals and finance." "It's trying to find that balance from a developer's point of view, you're trying to create homes for other people, and they're just trying to protect theirs." "If you do these public consultations, you're actually able to manage the narrative rather than dealing with the fire." "You can't create community in place if they're not on board." "You can't afford community engagement, but you can approach it strategically." 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/ https://www.propertydevelopersiq.co.uk/ https://www.propertydevelopersplaybook.co.uk/

    30 min
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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.

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