Cuttable founders Jack and Sam are the unlikely duo behind one of Australia’s most exciting AI startups - one is a former agency creative, the other sold A Cloud Guru to Pluralsight for $2B in 2021. Together, they’re using AI to bring creative craftsmanship back to advertising.

Why this conversation is important? Jack and Sam are rethinking how ads get made in an AI-saturated world. With one foot in old-school storytelling and the other in frontier tech, they offer a blueprint for what creative work looks like in the future.

What Jack and Sam reveal in this episode:

- How Sam’s $2B exit and Jack’s Mad Men-like childhood made them an unlikely but compatible duo

- The emotional advice Jack’s dad gave him that still drives him today- How Sam’s volatile childhood made him risk-averse

- Why most AI-generated ads look like catalog junk (and how Cuttable was born)

- Their competitive edge over startups like @Icon

- Why creative humans will remain the highest leverage

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Thanks to our sponsors Zeller and KC Ventures.

Zeller is building the financial stack to help startups scale, called Zeller for Startups. https://www.myzeller.com/startups. Every founder unlocks exclusive rewards and offers when you use Zeller for Startups — including a high-interest savings account, 12-month free access to Zeller Corporate Cards and expense management, and discounts on amazing partner solutions from Employment Hero, Xero, and Pop Business.

KC Ventures helps Australian startups scale by providing strategic financial advice. You can find KC Ventures at http://kcventures.com.au/ or message their founder Luke Rix on Linkedin to get in contact directly.

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Enjoyed this video? You may like our most recent documentary on Relevance AI - an Aussie startup in the global AI agent race https://youtu.be/oanG_oIYU7Q?si=8VKA2OzW-jV4SINW

Chapters

00:00 Introduction

01:54 The Unlikely Duo

04:34 Sam's Journey from Tech Training to Advertising

09:44 Zeller Ad

11:13 Jack's Advertising Roots

14:10 The Evolution of Advertising

19:10 The Birth of Cuttable

31:17 Redefining Customer Mindset

31:53 Testing Theories with SMBs

32:22 Merging Industries and Building Vision

32:32 KC Ventures Ad33:24 Challenges in Advertising

34:01 The Importance of Quality in Ads

36:45 Balancing Quality and Quantity

37:09 Philosophy and Product Development

43:40 The Role of AI in Advertising

49:54 Recruiting Talent for Innovation

58:26 Staying Hungry and Passionate

01:03:00 Conclusion and Call to Action

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We are two best friends, trying to build a community around in-depth interviews and short documentaries with the best minds in technology and startups. Through bold storytelling and candid conversations, we explore how visionary thinkers are shaping the future. The best way to support is subscribing, truly it makes all the difference for us 💙