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Justin Wastnage is the founder and CEO of Vloggi, a platform that transforms everyday mobile phone footage into trusted, structured, legally owned video assets for businesses and enterprises. What started as a tool for tourism boards to crowdsource location content has evolved, through COVID, multiple pivots, and years of customer-funded development, into an infrastructure layer that verifies, structures and processes video for some of the world's most compliance-heavy industries.

In this episode, Justin joins Alan to talk honestly about the challenges of pitching a business that investors think they already know. Vloggi has worked with Major League Baseball, Netflix, the NSW Government, Google Ads and RFK's presidential campaign, yet raising in Australia remains stubbornly difficult. Alan digs into why that is and what Justin can do about it, from repositioning the pitch, to rebranding, to putting someone else in the room.

If you're a founder who has pivoted hard but can't shake what investors remember about your old story, this one is for you.

00:00 - Intro

02:03 – Meet Justin Wastnage and the origins of Vloggi

04:57 – What Vloggi does: video as content, data and evidence

07:11 – What changed with synthetic AI video and why it matters now

09:00 – The pivot story: from tourism boards to enterprise compliance

12:35 – Bootstrapping and the team behind Vloggi

13:03 – The current raise: $800k to bring the enterprise product to market

17:03 – How Vloggi verifies that uploaded video is authentic, not AI-generated

19:33 – Commercial model: per project vs ongoing enterprise licensing

22:31 – Why Vloggi wants to be infrastructure, not a consumer brand

24:48 – Alan's challenge: how to reposition when investors think they know your old story

29:08 – Should you rebrand? The case for and against

32:26 – Pitch deck strategy: teaser first or full deck upfront?

35:23 – Alan pitches Vloggi back to Justin the way he'd do it

38:51 – The airline use case and how to open with one vertical then go broad

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Why Investors Keep Saying No (And What to Do About It) | Justin Wastnage from Vloggi