Peer-to-Peer Roundtable Lunch Series, B2B Sales Strategies: How I Scaled Startups from Zero to $175M in 24 Months

​Connect. Learn. Grow.

​Join us for the Peer-to-Peer Roundtable Lunch Series—a meetup for Caledon-based entrepreneurs craving real talk, real tools, and real connections.

​Each session features a themed discussion led by Darren Shivraj, Program Lead at the Humber River Centre, and spotlights an Expert-in-Residence (EiR) from the DMZ network.

​Expect candid insights on startup essentials—from customer discovery to scaling strategies—and walk away with actionable advice and new connections. Powered by the Town-funded incubator, this is your go-to space for building business momentum in your own backyard.

​Meet your DMZ Expert in Residence – Andrea Matheson

​Areas of Expertise:

• ​High Growth Coaching

• ​Scaling Startups

• ​Strategic Problem Solving

• ​Change Management

​Andrea Matheson is a high-growth coach, multi-exit entrepreneur, and elite problem solver. With a track record of building three startups to successful exits—including one that scaled to US$175 million across three continents in just 24 months—Andrea brings unparalleled insight to founders navigating rapid growth.

​She’s advised over 1,000 entrepreneurs in the last five years, helping them tackle complex challenges, uncover blind spots, and scale with confidence. Andrea’s style is direct, thoughtful, and deeply strategic—expect tough questions, honest feedback, and actionable next steps.

​She believes in empowering founders to take smart risks, especially women in tech, and reminds all entrepreneurs: “Rest is key to growth in every area of your life.”