In this episode, Gav sits down with Wayne Gerard to unpack his ongoing founder journey - from army officer to building RedEye, one of Australia’s early enterprise SaaS companies, through to becoming an active investor and launching new ventures like My Planner and Cetana.
This is not a story about what was - Wayne is still very much in the journey, continuing to build, evolve and back other founders while navigating the realities of business and life.
Expect a candid, behind-the-scenes look at what it really takes to launch a B2B SaaS company from scratch, the pressure it entails and how it can impact your health if you're not careful.
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In this episode, we cover:
- Why Wayne is still in the journey - evolving from founder to investor while continuing to build
- Wayne’s early career in the army and transition into tech
- The moment he decided to take the leap into entrepreneurship
- Early business failures and lessons on timing and co-founder alignment
- The origin story of RedEye and identifying a real market gap
- What it was like building enterprise SaaS before cloud was widely adopted
- The reality of founder pressure, burnout and panic attacks
- Raising capital and the hidden toll it takes
- Why founders must stop being the product to scale
- Building a repeatable sales engine in enterprise SaaS
- The difference between a demand problem and a sales problem
- How to think about risk and make better decisions as a founder
- The importance of deep customer relationships
- Lessons on leadership, delegation and letting people grow
- Why most startups are just apps - not real businesses
- The transition from founder to investor and what changes
- What makes a great founder in today’s environment
- How AI is reshaping SaaS and enterprise sales
- The importance of balancing health, wealth and longevity
- What keeps Wayne motivated across multiple ventures
Wayne Gerard:
What is The Leap by Founders Collective?
The Leap is a podcast for founders, creatives, and career-shifters who are bold enough to start something of their own. Hosted by Gavin Tye, each episode dives into the real stories behind people who’ve taken the leap...from launching startups and scaling side hustles to pivoting careers with purpose.
Through candid conversations with early-stage founders, innovators, and changemakers, we explore the messy middle of entrepreneurship: the fears, breakthroughs, lessons, and mindset shifts that come with building something meaningful from the ground up.
Whether you’re thinking about starting a business or already deep in the trenches, The Leap will leave you feeling inspired, informed, and ready to take your next big step.