Why Most Live Events Lose Money (Sales Tips that keep a customer engaged for 3+ years) with Shay Whitton episode artwork

EPISODE · May 20, 2026 · 52 MIN

Why Most Live Events Lose Money (Sales Tips that keep a customer engaged for 3+ years) with Shay Whitton

from That F*cking Marketing Podcast · host TFM Digital

What happens when you have a customer sale cycle of 728 days? In today’s episode, Taylor is sitting down with Shay Whitton from Positive Real Estate, Australia’s FIRST buyers agents who have been working in the industry in 2003, well before the marketing world became funnels, retargeting ads and AI generated everything. Since then, the business has coached more than 7.5k clients, closed over 10k property deals and has built a marketing strategy that keeps people engaged, educated and emotionally bought in for years. In an era where it’s getting harder to hold your customer’s attention for five minutes, hearing how Shay nurtures an audience for hundreds of days is pretty bloody useful. Key moments: 0:00 - What marketing looked like before Facebook, Google ads and smartphones  3:54 - Shay’s best property deal, worst property deal and the $30M mistake that became a very expensive lesson 5:09 - How do you keep someone interested when they might not buy from you for 728 days?  9:18 - Why warm leads need more than just emails, funnels and follow-ups to stay engaged with your business 13:08 - How Positive Real Estate built extra services around the problems their customers kept running into  14:31 - The biggest mistake businesses make when they’re marketing to people over a long sales cycle  16:00 - Live events: how do they play into a long term customer strategy? 23:48 - What do live events look like for smaller businesses? 26:13 - How many people is normal to show up for an event? 27:40 - What going from head marketer to the CMO looked like (and why you need to prepare for more check-ins than you’re doing now) 34:43 - What founders should do before they hire someone to take marketing off their plate  39:05 - How Positive Real Estate are using AI right now 46:09 -  Can you use AI and still maintain trust with your customers? 49:19 -  Shay’s advice for anyone who keeps saying they want to invest in property and still hasn’t done anything If you want to know more about Positive Real Estate, you can find the links below. Website - www.positiverealestate.com.au Facebook - www.facebook.com/positiverealestate Instagram - www.instagram.com/positiverealestate Register for a free property night here

What happens when you have a customer sale cycle of 728 days? In today’s episode, Taylor is sitting down with Shay Whitton from Positive Real Estate, Australia’s FIRST buyers agents who have been working in the industry in 2003, well before the marketing world became funnels, retargeting ads and AI generated everything. Since then, the business has coached more than 7.5k clients, closed over 10k property deals and has built a marketing strategy that keeps people engaged, educated and emotionally bought in for years. In an era where it’s getting harder to hold your customer’s attention for five minutes, hearing how Shay nurtures an audience for hundreds of days is pretty bloody useful. Key moments: 0:00 - What marketing looked like before Facebook, Google ads and smartphones  3:54 - Shay’s best property deal, worst property deal and the $30M mistake that became a very expensive lesson 5:09 - How do you keep someone interested when they might not buy from you for 728 days?  9:18 - Why warm leads need more than just emails, funnels and follow-ups to stay engaged with your business 13:08 - How Positive Real Estate built extra services around the problems their customers kept running into  14:31 - The biggest mistake businesses make when they’re marketing to people over a long sales cycle  16:00 - Live events: how do they play into a long term customer strategy? 23:48 - What do live events look like for smaller businesses? 26:13 - How many people is normal to show up for an event? 27:40 - What going from head marketer to the CMO looked like (and why you need to prepare for more check-ins than you’re doing now) 34:43 - What founders should do before they hire someone to take marketing off their plate  39:05 - How Positive Real Estate are using AI right now 46:09 -  Can you use AI and still maintain trust with your customers? 49:19 -  Shay’s advice for anyone who keeps saying they want to invest in property and still hasn’t done anything If you want to know more about Positive Real Estate, you can find the links below. Website - www.positiverealestate.com.au Facebook - www.facebook.com/positiverealestate Instagram - www.instagram.com/positiverealestate Register for a free property night here

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Why Most Live Events Lose Money (Sales Tips that keep a customer engaged for 3+ years) with Shay Whitton

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This episode was published on May 20, 2026.

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What happens when you have a customer sale cycle of 728 days? In today’s episode, Taylor is sitting down with Shay Whitton from Positive Real Estate, Australia’s FIRST buyers agents who have been working in the industry in 2003, well before the...

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