From Construction to Real Estate Mogul

Henderson’s path to real estate wasn’t conventional. Before entering the industry, he worked as a machine operator in mining and construction. But after discovering buyer’s advocacy, he quickly transitioned, launching Henderson Advocacy in 2021. Fast forward to 2025, his firm now handles 40-50 property transactions per month with a team of nearly 60 advocates and 120 employees across Australia.

His secret? Standing out.

The Power of Branding
Henderson’s bold, flamboyant branding—think flamingo motifs and eye-catching suits—wasn’t just for show.

“We just wanted to be cool,” he jokes, but the strategy was deliberate. In an industry dominated by conservative players, Henderson’s unapologetic persona cut through the noise.

“I’ve always only listened to the opinions of people I respect,” he says. “If someone’s criticising me but hasn’t achieved what I have, why would I care?”

His branding wasn’t just about aesthetics, it was about authenticity. By being himself, he attracted clients who aligned with his values, rather than trying to please everyone.

Controversy & Crisis: The Turning Point
Henderson’s rise wasn’t without turbulence. In 2023, he faced a media firestorm—a high-profile exposé questioned his business practices, and his revenue dropped 30%. At the same time, his partner was diagnosed with breast cancer.

“It felt like my world was collapsing,” he admits.

Instead of retreating, Henderson pivoted:

• Shifted from referral-based leads to direct B2C marketing (now spending $300K/month on ads).

• Doubled down on lifetime customer value, expanding into finance, renovations, and property management.

• Exited a business partnership, taking full control of Henderson Advocacy.

By 2024, his business was 400% up from the previous year.

Rentvesting: The Smart Investor’s Strategy
Henderson is a vocal advocate for rentvesting—renting where you want to live while investing in more affordable, high-growth areas.

“Why tie up $2 million in a home when you can rent it for a fraction of the cost and invest elsewhere?” he argues.

His reasoning?

Flexibility: He can move without the hassle of selling.

Leverage: Capital is deployed into appreciating assets rather than locked into one property.

Affordability: Many Australians can’t buy where they want to live—renting allows them to stay while building wealth.

“Rich people live in major cities. If you’re not rich yet, you won’t afford it—that’s just reality.”

Ultra-Marathons & Mental Toughness
Henderson’s discipline extends beyond business. A non-runner just a few years ago, he now completes ultra-marathons, including a 205-mile (330km) run—one of the toughest in Australia.

“Every time I do something I didn’t think I could, my confidence grows,” he says.

His approach? Public accountability. By declaring his goals, he forces himself to follow through.

The Billion-Dollar Vision
Henderson’s next big play? Property management.

“There are 3 million investment properties in Australia, yet the biggest player only manages 20,000,” he notes. His goal? 50,000 under management in five years.

How?

Tech-driven efficiency: Separating client relations from property inspections.

Acquisitions: Already in talks to buy a 4,500-property portfolio.

Lifetime customer value: Capturing clients early (as tenants) and nurturing them into buyers.

“If I can spend the most to acquire a customer because their lifetime value is higher, I’ll always win.”

Key Takeaways
• Brand Authenticity Wins – Henderson’s success proves that standing out (even controversially) attracts the right clients.

• Rentvesting Works – If you can’t afford to buy where you want to live, rent there and invest elsewhere.

• Crisis = Opportunity – When his business was under fire, Henderson pivoted, leaned into marketing, and came back stronger.

• Lifetime Value Over Short-Term Profit – Building ancillary services (finance, renovations, property management) maximizes customer value.

• Public Accountability Drives Success – Whether in business or ultra-marathons, declaring goals forces execution.

Jack Henderson’s story is a testament to resilience, strategic thinking, and the power of staying true to yourself – even when the world pushes back.

Listen to the full episode on the With the Fox podcast here: https://open.spotify.com/episode/0ZV9Mw5Y2ha73lsgOdy1Tg?si=f70adf80ec274ec0

Follow Jack on Instagram @jackchenderson