From a childhood without electricity to co-founding a listed betting company, Oliver Shanahan’s story is a masterclass in technical grit and commercial pivots. As the Group Head of Cybersecurity and Infrastructure at BetMakers Technology Group, Oliver traces his path from wiring up early ISPs and mining ERPs to building TopBetta from a two-person LAMP stack into an ASX-listed business.

In this episode of Tech Execs, James MacDonald sits down with Oliver as he unpacks the high-stakes realities of bookmaking, the decision to pivot from B2C to B2B through acquisitions like Dynamic Odds, Global Betting Services, and Sportech, and why they rebuilt a legacy monolith into a cloud-native, multi-tenant platform that now powers 35+ sportsbooks. We also dig into ISO 27001 in practice, due diligence on tech debt, and how to use AI without leaking your IP. A candid, deeply technical blueprint for founders and engineering leaders navigating scale, regulation, and replatforming you won’t want to miss.

In this episode of Tech Execs, James MacDonald heads to Melbourne to sit down with Matt Vitale, former co-founder of Australia’s largest equity crowdfunding platform and now Executive Director at New Dialogue. Matt traces his winding path from nightlife promoter and sugarcane juice tinkerer to financial services lawyer, then startup pioneer, where he helped more than 300 companies raise over $250M. He shares the breakout Sheba Rideshare campaign, why storytelling and community trump slick code, and how a $300K LaunchVic grant sparked a hardware-focused angel network that became their most successful to date.

Tune in to hear Matt break down how enterprises can safely adopt AI by deploying open-source large language models inside their own secure environments—model-agnostic, auditable, and up in days, not months. He makes the case for bottom-up experimentation, rapid pilots, and why compliance-by-design will be the real moat as regulation catches up. Alongside the professional achievements, Matt also shares the daily practices (think meditation, breath work, and long works) that helped him reset following burnout. A must listen for those working in the rapidly evolving AI space.

Victoria Aspden, Executive General Manager - Digital & Transformation at Ampcontrol has had an unconventional career journey. Initially choosing technology for its earning potential, she managed to work her way through the field when recruiters valued her relationship-building skills over pure technical credentials. This pattern of people taking chances on her became a defining theme throughout her career.

In this episode of NTP’s Tech Exec podcast series, Victoria sits down with James MacDonald to discuss her diverse career and her core management frameworks, including ‘problem before solution’, ‘people, process, tech, data’ and their interconnectedness, and the ‘cone of uncertainty’. Victoria advocates for hiring people smarter than yourself and creating environments where vulnerability and honest communication are valued over technical expertise alone. Tune in to hear Victoria’s advice for leaning into your weird, and how challenging traditional gender roles in her family has allowed her career success.