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From facing Roger Federer in the Wimbledon final to losing millions on bad investments, Mark Philippoussis’ life has been a rollercoaster of extreme highs and crushing lows. Known as "The Scud" for his record-breaking serves, Mark was one of the few players who could defeat legends like Pete Sampras and Andre Agassi—but his biggest battles weren’t on the court, they were in life.

In this raw, no-holds-barred conversation, Mark reveals:
🔥 What it’s REALLY like to play in a Wimbledon final against Federer.
🔥 How he lost millions on cars, real estate, and impulsive decisions.
🔥 The mental toll of forced retirement & battling depression.
🔥 The comeback story—how he rebuilt his life after losing everything.
🔥 What today’s young athletes need to know about money & fame.

Timestamps:
0:00 – Intro: Meet Mark Philippoussis
1:15 – Growing Up & Finding Tennis
4:47 – How His Parents Shaped His Career
9:25 – Turning Pro: The Pressure & Reality~
16:26 – The Matches He’ll Never Forget
26:03 – The Secret to Staying Mentally Focused
28:33 – Handling the Roar of the Crowd
29:47 – The 1999 Davis Cup: A Career-Defining Moment
32:45 – Wimbledon Final Against Federer: The Inside Story
37:57 – Injuries & Surgeries: The Brutal Side of Tennis
48:30 – The First Big Paycheck & How It Changed Everything
53:13 – Losing Millions: Cars, Real Estate & Bad Investments
57:27 – Forced Retirement: The Toughest Decision
59:55 – The Mental Toll: Dealing with Depression
1:04:44 – Impulsive Purchases & The Cost of Fame
1:10:54 – How His Past Mistakes Shaped His Parenting
1:12:51 – Life After Tennis: What Comes Next?
1:15:43 – The 20-20-20 Formula: His New Approach to Life
1:25:07 – The Goals Driving Him Forward
1:26:29 – Final Thoughts & Lessons Learned

If you’ve ever wondered how elite athletes transition to life after the game—or how anyone can bounce back from financial failure—this episode is packed with unfiltered insights you can’t afford to miss.

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Welcome to Stripping Off with Matt Haycox
This isn’t your average business podcast. It’s where real entrepreneurs, celebs, and industry leaders strip back the polished PR, and get brutally honest about the journeys that made them.

Hosted by entrepreneur and investor Matt Haycox, Stripping Off dives into the raw, unfiltered realities behind success: the wins, the fuck-ups, the breakthroughs, and everything in between. No scripts. No sugar-coating. Just real talk from people who’ve lived it.

Whether you’re hustling to scale your business or just love a behind-the-scenes look at how people really make it, this podcast is your front-row seat to the truth behind the triumphs.

Who Is Matt Haycox? - Click for BADASS Trailer