#43 Wingman

Nick and Jonathan join Gavin to share how they built Wingman, a company that’s transforming real estate operations with offshore admin solutions. Starting in property management, Jonathan grew his business from 60 to 3,000 properties, leveraging virtual assistants in the Philippines. Together, Nick and Jonathan now lead a team of 900 staff supporting 700 real estate agencies, streamlining operations to maximize productivity.

They discuss the real estate industry's misconceptions about outsourcing, the power of offshore support, and how Wingman helps agencies scale. From overcoming skepticism to building trust with top-performing agents, they explain why delegation is the key to growth.

Episode Breakdown:

[0:00 - 5:00] The origin of Wingman – Jonathan’s journey from a 23-year-old property manager to leading a high-growth business through offshore admin support.

[5:00 - 10:00] From 60 to 300 properties: How outsourcing admin tasks enabled rapid business growth.

[10:00 - 15:00] The role of offshore teams in real estate – how Wingman helps agencies free up time for high-value work.

[15:00 - 20:00] The common myths about outsourcing: Why it’s not just about cutting costs but driving business expansion.

[20:00 - 25:00] Behind-the-scenes of Wingman’s operations – training, quality control, and ensuring offshore teams integrate seamlessly.

[25:00 - 30:00] How Wingman’s support allows real estate professionals to focus on revenue-generating activities.

[30:00 - 35:00] The biggest lessons from scaling a business – leadership, efficiency, and the power of delegation.

[35:00 - 40:00] What’s next for Wingman: Future expansion, the Profit Summit event, and their vision for helping more agencies grow.

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