#19: Why you aren't using AI Right! Jake Shelley on helping scale Deputy to $100 million, Leadership and building Jiffi

The Long Pour with Brendon Hill · Jul 23, 2026 · 47m

Jake Shelley has lived two completely different business lives.

First, he helped build Deputy from one of Australia's fastest-growing startups into a business worth more than $100 million alongside a core team that stayed together through years of growth.

Now he's doing it all again as the founder of Jiffi.

In this conversation we explore what changes when you move from being an operator inside a successful company to carrying the responsibility of being the founder.

We also dive into one of the biggest topics in business today: AI.

Not from the perspective of hype—but from how businesses and…