Welcome again to Season 3 of The Land Pioneers Podcast!

Episode 2 of Season 3 is with Ben Howard, founder of Monopoly Group and a true pioneer in strategic land development and real estate investing. Ben turned early hardship into opportunity, building a property portfolio and career across Australia and the UK, and bringing a refreshingly honest perspective to our podcast.

In this episode, we explore how Ben’s early life experiences shaped his passion for business and property, and how he turned adversity into an advantage through creativity, hustle, and a commitment to growth. 

Full Episode

Ben’s story begins far from the boardrooms of land development. After the devastating loss of his two brothers to suicide, Ben left school in Year 10 and found himself without direction, support, or a place to call home. For five years, he lived on a homeless allowance, couch-surfed, and struggled to make sense of his circumstances.

Yet within that chaos, a spark ignited. Music became his emotional outlet and first entry into entrepreneurship. Through band promotions and event organising, Ben discovered his love for building things — not just in music, but in business. He began investing in traditional residential real estate, and after enrolling in a business course, he began offering to write free business plans for local stores in Rundle Mall, using lunchtime hours to sharpen his skills.

At 19, he purchased his first home—a $69,000 ex-housing trust property in Taperoo—using a first home buyer’s grant and borrowed money for the deposit. It wasn’t glamorous, but it was cash-flow positive. His mentor explained the value of yield and equity, and from that moment, Ben was hooked.

What followed was a rapid expansion into real estate. By his early 30s, he had bought, sold, or held nearly 20 properties. But growth wasn’t always linear. He quickly learned the difference between equity and cash flow, how serviceability limits affect scalability, and the importance of having adaptable income streams.

When banks tightened lending during a market shift, Ben didn’t collapse — he pivoted. He returned to event production, organising major dance competitions and concerts to sustain his momentum.

Later, Ben moved to London with his partner. He applied for many jobs without formal qualifications before landing a junior sales role. Through persistence and follow-up, he eventually became Head of Entertainment – Sales at The SSE Arena, Wembley, managing events, exhibitions, and large-scale contracts. That experience deepened his negotiation, sales, and international project management knowledge—skills that would become core to his property development success.

Ben returned to Australia with a renewed focus. Through Monopoly Group, he began acquiring and developing land in high-growth areas, particularly those aligned with future government infrastructure. His developments in South Australia and Victoria reflect a strategic, forward-looking approach — investing in the corridors of tomorrow, not just the opportunities of today. 

 Learn more about Ben and Monopoly Group here. 

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