The Founder’s Journey

From first idea to lasting success: the stories, challenges and lessons behind building a thriving business.

What does it take to turn an idea into a successful business, navigate the challenges of growth and build something that lasts?

Join the Old Scotch Collegians for The Founder’s Journey, an engaging discussion with three Old Boys who have built successful businesses across different industries. Hear first-hand about their experiences, from taking the initial leap into entrepreneurship to growing organisations, building strong relationships and creating lasting impact.

Sebastian Watkins (OSC 2001) is CEO and Co-Founder of Lendi Group, the business behind Aussie and Lendi. Since co-founding Lendi in 2013, Sebastian has helped grow the digital mortgage start-up into one of Australia’s leading property and finance platforms, with a loan portfolio exceeding $108 billion. Sebastian will join the discussion via videolink, sharing insights into business growth, innovation and the role of technology in shaping the future.

Sam Sycamore (OSC 2001) is Founder and Managing Director of Category 5, a workforce solutions and rail services business established in Port Hedland in 2009. Growing the business organically from a sole operation into a national provider, Sam has built lasting partnerships across the resources and rail industries, while creating employment and training opportunities for local communities.

Aaron McDonald (OSC 2001) founded Pragma in 2014 after building his career in commercial law. An experienced legal practitioner and advocate, Aaron is also committed to access to justice and legal education, having founded the Subiaco Community Legal Service, where he serves as Chair.

From identifying opportunities and overcoming challenges to scaling a business, building trusted partnerships and giving back to the community, our speakers will share the lessons that have shaped their journeys and the insights they’ve gained along the way.

Whether you’re an aspiring entrepreneur, business owner or simply interested in what it takes to build a successful business, this is an opportunity to learn from those who have done it.

Event details:

Date: Wednesday, 18 November 2026

Time: 5.30pm event start for 6.00pm presentation

Venue: Pragma Lawyers, 282 Rokeby Road Subiaco

Tickets: $30

For further information, please contact the OSC.

Update your details: To ensure you receive future correspondence, please update your details on the College website or by contacting the OSC office at osc@scotch.wa.edu.au.

Contact the host of Scotch Business Directory: The Founder’s Journey

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