Real Estate Sessions Rewind - Matthew Simpson, co-Founder Lolo
15 July 2025

Real Estate Sessions Rewind - Matthew Simpson, co-Founder Lolo

The Real Estate Sessions

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Local Loyalty: How Lolo Transforms Agent-Client Relationships

Matthew Simpson, co-founder of Lolo, shares the pivotal role of maintaining connections within the real estate industry through thoughtful engagement strategies. He articulates how Lolo provides real estate agents with a sophisticated tool designed to facilitate ongoing communication with their sphere of influence by sending curated local gifts on a monthly basis. This initiative not only fosters loyalty among clients but also champions local businesses, thereby enriching community ties. Throughout our discussion, we delve into the evolution of Lolo and the significance of leveraging technology to enhance personal relationships in a competitive market. Additionally, Matthew shares invaluable insights on the importance of building a robust network and the lessons learned from navigating the complexities of entrepreneurship within the real estate sector.





The dialogue between Bill Risser and Matthew Simpson unfolds a narrative rich in insights about the evolution of Lolo, a platform designed to maintain connections between real estate professionals and their clientele. Matthew, drawing from his extensive experience in the real estate sector, elucidates how Lolo curates local gifts, thereby fostering a sense of community and enhancing client relationships. The discussion delves into the challenges faced by local businesses amid the dominance of larger corporations, and how Lolo aims to provide these businesses with a competitive edge through innovative marketing strategies. Matthew articulates the importance of sustaining local culture and economy, illustrating how Lolo not only benefits agents in their outreach efforts but also supports small enterprises in becoming visible and engaging within their communities. This episode captures the essence of modern entrepreneurship in real estate, emphasizing relationship-building as a pivotal approach in an increasingly digital world.

Takeaways:

    Matthew Simpson discusses the inception of Lolo, a platform designed to enhance connections between real estate agents and their local communities. The Lolo service curates monthly gifts from local businesses, enabling agents to maintain engagement with their sphere of influence effectively. Simpson emphasizes the importance of relationships in real estate, advocating for agents to focus on networking from the outset of their careers. The podcast highlights the evolution of Lolo from a technology initiative to a business centered on curating meaningful local experiences for clients. Simpson shares insights on overcoming fears of rejection in sales, urging new agents to embrace failures as opportunities for growth and learning. The conversation reveals Lolo's commitment to supporting local businesses and fostering sustainable community engagement through thoughtful gifting.