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

EPISODE · Nov 26, 2025 · 55 MIN

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

from Bothsides Podcast · host Bothsides Podcast

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)Explore the Bothsides Ecosystem ⁠⁠⁠⁠⁠here⁠⁠⁠⁠You can watch us on ⁠⁠⁠⁠⁠⁠⁠Youtube ⁠⁠⁠⁠⁠⁠⁠Find us on ⁠⁠⁠⁠⁠I⁠⁠nstagram⁠ ⁠⁠⁠⁠⁠⁠Join us on ⁠⁠⁠⁠⁠⁠⁠Tik Tok ⁠⁠⁠⁠⁠⁠⁠Hosted by ⁠⁠⁠⁠Dan Beardall⁠⁠⁠⁠,⁠⁠⁠ ⁠Kevin Buchanan⁠⁠⁠⁠ and⁠⁠⁠ ⁠Josh Morrissey ⁠⁠⁠⁠Follow Bothsides on Spotify so you never miss an episode! Thank you for listening.

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)Explore the Bothsides Ecosystem ⁠⁠⁠⁠⁠here⁠⁠⁠⁠You can watch us on ⁠⁠⁠⁠⁠⁠⁠Youtube ⁠⁠⁠⁠⁠⁠⁠Find us on ⁠⁠⁠⁠⁠I⁠⁠nstagram⁠ ⁠⁠⁠⁠⁠⁠Join us on ⁠⁠⁠⁠⁠⁠⁠Tik Tok ⁠⁠⁠⁠⁠⁠⁠Hosted by ⁠⁠⁠⁠Dan Beardall⁠⁠⁠⁠,⁠⁠⁠ ⁠Kevin Buchanan⁠⁠⁠⁠ and⁠⁠⁠ ⁠Josh Morrissey ⁠⁠⁠⁠Follow Bothsides on Spotify so you never miss an episode! Thank you for listening.

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

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This episode was published on November 26, 2025.

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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...

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