Nov 27, 2025

EP 138 | Matt Pillios: From Broke at 35 to $600M in Sales! How to Win Without Losing Yourself!

EP 138 | Matt Pillios: From Broke at 35 to $600M in Sales! How to Win Without Losing Yourself!

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Description

Matt Pillios reveals how he went from broke and in debt to selling $600M in property and why "winning ugly instead of losing pretty" changed everything. He shares the athlete mindset, daily systems, and brutal truths that turned his life into sustainable success.

Matt Pillios is the Director of Kay & Burton and was ranked Victoria's #1 real estate agent in 2023, selling over 200 properties worth $600M+ in two years while working with AFL stars and high-net-worth clients.

After being broke for his first four years in real estate and starting at 35, he redefined how he approaches work, fitness, relationships, and wealth.

He explains:

◼️ Why he treats real estate "like an AFL season" (and takes a mandatory off-season)

◼️ The 11-out-of-14 training routine that keeps him mentally sharp

◼️ Why your partner at home is your most important business decision

◼️ What billionaires told him about being "truly rich"

◼️ The difference between winning ugly and losing pretty (and why it matters)

◼️ Why getting physically fit changed everything about his business

◼️ The toxic clients he fired that led to his best year ever

◼️ How to handle financial stress without destroying yourself

◼️ Why wealthy people have the most regrets (and how to avoid them)



Matt Pillios reveals how he went from broke and in debt to selling $600M in property and why "winning ugly instead of losing pretty" changed everything. He shares the athlete mindset, daily systems, and brutal truths that turned his life into sustainable success.

Matt Pillios is the Director of Kay & Burton and was ranked Victoria's #1 real estate agent in 2023, selling over 200 properties worth $600M+ in two years while working with AFL stars and high-net-worth clients.

After being broke for his first four years in real estate and starting at 35, he redefined how he approaches work, fitness, relationships, and wealth.

He explains:

◼️ Why he treats real estate "like an AFL season" (and takes a mandatory off-season)

◼️ The 11-out-of-14 training routine that keeps him mentally sharp

◼️ Why your partner at home is your most important business decision

◼️ What billionaires told him about being "truly rich"

◼️ The difference between winning ugly and losing pretty (and why it matters)

◼️ Why getting physically fit changed everything about his business

◼️ The toxic clients he fired that led to his best year ever

◼️ How to handle financial stress without destroying yourself

◼️ Why wealthy people have the most regrets (and how to avoid them)



Matt Pillios reveals how he went from broke and in debt to selling $600M in property and why "winning ugly instead of losing pretty" changed everything. He shares the athlete mindset, daily systems, and brutal truths that turned his life into sustainable success.

Matt Pillios is the Director of Kay & Burton and was ranked Victoria's #1 real estate agent in 2023, selling over 200 properties worth $600M+ in two years while working with AFL stars and high-net-worth clients.

After being broke for his first four years in real estate and starting at 35, he redefined how he approaches work, fitness, relationships, and wealth.

He explains:

◼️ Why he treats real estate "like an AFL season" (and takes a mandatory off-season)

◼️ The 11-out-of-14 training routine that keeps him mentally sharp

◼️ Why your partner at home is your most important business decision

◼️ What billionaires told him about being "truly rich"

◼️ The difference between winning ugly and losing pretty (and why it matters)

◼️ Why getting physically fit changed everything about his business

◼️ The toxic clients he fired that led to his best year ever

◼️ How to handle financial stress without destroying yourself

◼️ Why wealthy people have the most regrets (and how to avoid them)



About this Guest

About this Guest

About this Guest

Matt Pillios

Matt Pillios

Matt Pillios

Agent to the Stars | Director, Kay & Burton

Agent to the Stars | Director, Kay & Burton

Agent to the Stars | Director, Kay & Burton

Matt Pillios is one of Victoria’s most awarded real estate agents and a leading force in Brighton and Bayside property. As a Director at Kay & Burton, he’s built a reputation for unmatched energy, precision, and results — consistently setting suburb benchmarks and cultivating a loyal network of long-term clients. Known for his commanding auction presence and exceptional negotiation skills, Matt brings a proactive, hands-on approach that drives momentum and maximises outcomes for every sale. His success is defined not just by record-breaking results, but by his unwavering commitment to delivering a world-class experience for every client he represents.

Matt Pillios is one of Victoria’s most awarded real estate agents and a leading force in Brighton and Bayside property. As a Director at Kay & Burton, he’s built a reputation for unmatched energy, precision, and results — consistently setting suburb benchmarks and cultivating a loyal network of long-term clients. Known for his commanding auction presence and exceptional negotiation skills, Matt brings a proactive, hands-on approach that drives momentum and maximises outcomes for every sale. His success is defined not just by record-breaking results, but by his unwavering commitment to delivering a world-class experience for every client he represents.

Matt Pillios is one of Victoria’s most awarded real estate agents and a leading force in Brighton and Bayside property. As a Director at Kay & Burton, he’s built a reputation for unmatched energy, precision, and results — consistently setting suburb benchmarks and cultivating a loyal network of long-term clients. Known for his commanding auction presence and exceptional negotiation skills, Matt brings a proactive, hands-on approach that drives momentum and maximises outcomes for every sale. His success is defined not just by record-breaking results, but by his unwavering commitment to delivering a world-class experience for every client he represents.

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Curated events.

© Copyright 2025, BOTHSIDES. All Rights Reserved

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