Andy drops a life-changing pact - and Jack’s way too quick to accept. Hamish admits he’s now reliant on ChatGPT (RIP Google), and worries what the robot thinks of him. The boys run a Gusto Check on a family business, pitting two brothers against each other in a tight battle, and Hamish kicks off this week’s Upset Andy with a personal account… involving the fruit bowl.

1. Andy’s $50k pact
2. Gusto check - brother vs brother
3. What does Chat GPT know about you?
4. Upset Andy

Hamish presents a new game to Andy which is sure to ruffle some feathers! There’s a very rare Chit Chat Champion result, and the Tallest Hat chat has triggered a childhood memory for Hame. Andy is testing the ‘honesty system’ for the work office kiosk, and Hamish thinks he’s finally found a skill to impress his wife…spoiler: keep trying Hame!

1. Who is Andy Lee cooler than?
2. Chat chat champion - golf chat
3. Tall hat update - Hamish has done this before
4. Ice skating
5. Stealing from the office kiosk

Andy has run into a legal issue with the Worlds Tallest Hat, there’s been an influx of Extreme Empaths, and the boys put their social skills to the test with a new game. Hamish gets into trouble at NZ airport, and Andy reveals an insane fact about his dad that shocks Hame & Jack!

1. Tall hat liability
2. Extreme empaths
3. Social skills name game
4. Hamish’s run in with NZ customs
5. Andy’s Dad has never bought a TV

Plans (and CAD’s) are well and truly underway for the Tallest Hat record attempt, but a concerning health risk has been flagged…
Andy issues an apology song to Jack for reading out his humiliating golf scores, but how sorry is he really? More solid power moves have been sent in, and Hamish is humbled by a member of his ‘family’!

1. Tallest hat - a small health risk
2. Andy’s apology song to Jack
3. Power moves
4. In the Hertz family

Promises were made by Hamish to secure a special guest for episode 300. Now that the milestone episode is here, we finally find out who the “chosen” guest is! Hamish has discovered that his wife, Zoe, enjoys policing the police. Andy shares an alarming message from the Tallest Hat WhatsApp chat. Plus, a Song Sleuth involving an Aussie classic, and we settle the debate no one asked for - who is the best team player in the vegetable world?

1. Episode 300 special guest!
2. Zoe policing the police
3. Tallest hat - how high!?
4. Song Sleuth - Waltzing Matilda
5. Vegetable team players

Jack and his golf cart have been spotted in the wild! Hamish confesses his guilty sneezing habit, and the boys take on the dying art of company jingles in a “Jingle Joust!”. We go deep inside the Tallest Hat Dream Team WhatsApp for a very important brim-related discussion, and love is making Andy do strange things!

1. Jack In The Wild
2. Letting a sneeze off the chain
3. Jingle Joust
4. A tall swagman’s hat?
5. Partner requests

Hamish questions what actually constitutes “a monkey on your back,” and how many monkeys the average person might be carrying. Naturally, he turns it into a case study - guessing how many monkeys they are each carrying around right now! There’s a toothpaste ad that has Andy completely baffled, and after much anticipation (so much so that we almost forgot), Hamish finally reveals the next industry that he’s about to blow wide open! Andy also takes us inside the WhatsApp chat of our Tall Hat Dream Team to deliver a very important update!

1. Monkeys on our backs
2. Colgate ad stitch up
3. Inside the tallest hat WhatsApp chat
4. Crumpets investigation