In this episode of Industry Disruptors, Ajay Nayyar and Jordanne Whiley MBE sit down with Jack Wilkinson — ex-footballer, chartered planning consultant, and seasoned property developer. Jack brings a unique perspective to the world of investment, combining the technical precision of planning with the real-world grit of development.
From Football to Floorplans
Jack’s story is far from typical. Starting his career on the pitch as a footballer for Ipswich, he quickly learned the value of teamwork, discipline, and strategic thinking. Those same qualities now fuel his success in two key property disciplines: planning consultancy and investment development.
After years working in local planning authorities, including enforcement and senior officer roles, Jack founded his own consultancy, Wilkinson Planning. He soon expanded into property development, applying his insider knowledge to unlock sites others might overlook. As he puts it, “If I can’t get planning on my own site, I’ve got a problem.”
Why Planning Knowledge Matters
Planning is often one of the most misunderstood (and feared) parts of the property journey. Jack broke it down with clarity:
- Start from the ground up: understand flood risk, contamination, and access.
- Then look above ground: heritage concerns, ecology, noise, and biodiversity net gain.
- Every site needs its own tailored strategy.
What gives Jack an edge? He knows what councils look for, how decisions are made, and where risks lie. That insight doesn’t just help his own projects — it’s also a huge benefit for clients.
From Risk to Reward
Planning can be risky. Jack shared examples, like a six-house scheme refused and lost on appeal. But with option agreements and long-term strategy, the risk was minimised. His focus? Always show a “route to approval.” That mindset has helped him succeed where others stall.
One standout deal: converting a Grade II listed office into six flats. Jack navigated 14 months of planning hurdles, building works, and valuation stress. But the outcome was worth it:
- Purchase price: £288,000 (subject to planning)
- Final valuation: £1.18 million
- Profit: 27% retained, all units now let
His takeaway: understand the full journey — from pre-application strategy to refinancing. Bring in the right professionals, and don’t skimp on due diligence.
Why Property Still Wins
Despite the rise of crypto and alternative investments, Jack believes UK property remains the strongest asset class. Yes, the market has changed. Yes, planning is tough. But if you can succeed in today’s conditions, you’re building long-term resilience.
His approach moving forward? Focus more on planning gain. Secure subject-to-planning deals, get approvals, then package them for sale. It’s smart, scalable, and plays to his strengths.
The Importance of People
Jack doesn’t just bring technical know-how — he understands the power of relationships.
- “You’ll never be criticised by someone doing more than you.”
- “If you’re the smartest in the room, you’re in the wrong room.”
- “I need people who live and breathe property, who pick up the phone at 9pm.”
That’s why he chooses to work with Hearthstone. As a developer, he values advisers who know the process end-to-end and can act fast.
Lessons for Investors
This episode isn’t just for developers — it’s for anyone serious about property. Jack’s key insights:
- Know your numbers, but also your risks
- Don’t let criticism from the sidelines slow you down
- Surround yourself with doers, not doubters
- Celebrate the wins, but always stay hungry
And if you’re buying land or doing deals? Get a planning consultant. As Jack puts it, even bat droppings can derail your timeline.
Ready to work with advisers who understand planning, risk, and real-world investing?
Hearthstone supports investors at every stage, from strategy to completion. Whether you’re planning your first conversion or scaling a development portfolio, we’ve got your back.
