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Most people remember the highlights: the serve, the swagger, the Wimbledon final, the Davis Cup hero moments.

They don’t remember what it costs.

In this episode, Mark Philippoussis gets brutally honest about what happens when you get big money young (a multi-million FILA deal at 17), hit world-stopping highs (beating world #1 Pete Sampras at 19), then your body breaks, your career ends without your permission, and you’re left dealing with the fallout, mentally, financially, and personally.

What you’ll learn in this episode

• The reality of making serious money at 17, and how it changes you.
• The mindset of a teenager taking down Pete Sampras (and why “no one expects you to win” can be a weapon).
• Comebacks aren’t motivational quotes, they’re rehab, dark days, and doing the work when no one’s watching.
• What forced retirement does to your identity (especially when you never chose it).
• Losing millions, making mistakes, and why asking “stupid questions” is how you get smart with money.
• Mark’s daily high-performance routine (the “20-20-20” first hour) and how he sets long-term + daily goals.

Timestamps
0:00 – Intro
1:13 – Coming Up
3:03 – The accidental start to a world-class career
10:30 – Signing a multi-million dollar contract at 17
18:35 – How a 19-year-old took down Pete Sampras
29:49 – 1999 Davis Cup: crowd pressure, nerves, and delivering anyway
32:36 – Wimbledon final (and the comeback year people forget)
38:27 – Knee surgeries, pain, and being told “you’ll never play again”
48:35 – Losing millions: mistakes, lessons, and rebuilding smarter
57:09 – Forced retirement (and falling out of love with the sport)
59:31 – Battling depression during the darkest stretch
01:07:47 – Why losing everything became the turning point
01:12:29 – The “20-20-20” high-performance formula + journaling routine
01:20:32 – Final Thoughts

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Dubai dating is a different planet. In this episode, Matt sits down with Christiana Maxion, a high-net-worth matchmaker who works with wealthy men looking for a serious partner, and charges $65,000 to $350,000 to do it.

They get into the brutal reality of “transactional” dating, where people say they want respect, while negotiating the relationship like a deal. Christiana explains why every relationship is transactional (money, emotions, sex, status, pick your currency), and why the real difference is the standard you hold and the environment you keep putting yourself in.

Then it turns into pure business: how her offline matchmaking agency works (vetting, background checks, concierge dates, feedback loops), what “success” actually means, and how she’s scaling it with MAX, a “matchmaking app” built to stop people wasting their lives in DMs and get them to the first date faster.

You’ll hear Matt & Christiana talk about:

• Why Dubai dating feels pay-to-play, and how to avoid ending up in the same loop.
• The real reason men pay $65k–$350k for matchmaking (hint: it’s not romance, it’s time).
• What her process actually looks like: vetting, alignment, concierge dates, and feedback.
• “Delusional” requirements (and the fastest way to ruin your dating life).
• How she built MAX: subscriptions, verification, compatibility matching, and auto-booked first dates.
• The business model behind a matchmaking agency (and why referrals are the real growth engine).
• Why she’s building separate matchmaking “portals” (expats, India, Muslim marriages) and expanding across the GCC.

Timestamps:
0:00 – Dubai dating is “transactional” (and why)
6:29 – “Every relationship is transactional” (standards vs expectations)
7:38 – How she started “Dating in Dubai” and got fired for it
9:26 – “I’m going to solve dating in Dubai” → launching matchmaking
10:13 – Why she only represents men + the 40,000-women database
11:03 – The pricing: $65k–$350k + what “success” means
13:38 – The “delusional age range” problem (and why it fails)
19:33 – MAX: paid subscriptions + passport/LinkedIn verification
20:37 – Why swiping broke dating + how MAX gets you to a real date
27:35 – App growth: UAE applications, active users, revenue
30:09 – A real success story (and a brutal horror story)
35:52 – What she’s building next (GCC expansion + new portals)
37:10 – Where to find Christiana + MAX

Follow Christiana Maxion
Instagram: https://www.instagram.com/christiana.maxion.matchmaker/
Website: https://christianamaxion.com
App: Maxion (available on the App Store)

Enjoyed this episode? Please subscribe to Stripping Off with Matt Haycox and leave a ★★★★☆ review on Apple Podcasts or Buzzsprout – it really helps others find us!

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Rob Lipsett says he hasn’t worked in 10 years, and he’s not saying that to flex. He’s saying it because he built a business that doesn’t rely on motivation, luck, or going viral. It relies on systems, content that ranks, and products people actually buy.

In this episode, Rob sits down with Matt to break down the real playbook behind his seven-figure fitness brand: how he started from zero, learned YouTube properly, and built an ecosystem that turns attention into income, without burning out or relying on one platform.

They go deep on what most creators and early-stage founders get wrong: thinking ads will make them rich, ignoring titles and thumbnails, and never building an offer that converts. Rob also shares his blunt views on market “saturation”, what biohacking actually does (and doesn’t) do, and how real estate became part of his long-term legacy plan.

If you’re building a personal brand, trying to escape the 9–5, or wondering how creators actually make real money, this episode will save you years of guessing.

You’ll hear Rob and Matt talk about:

• Why “market saturation” is a good thing (and why most people use it as an excuse).
• The real formula: titles + thumbnails + the first 15 seconds.
• How Rob went from early YouTube to a seven-figure business model.
• Why ads aren’t the business — your product is.
• Building an ecosystem: apps, partnerships, and offers that don’t depend on “posting more”.
• Supplements and biohacking: what’s real, what’s hype, and what to ignore.
• Real estate, Villa Lipsett, and how influence creates unexpected opportunities.

Timestamps
0:00 – Intro
1:04 – Coming Up
2:16 – Ireland’s First Fitness YouTuber
6:08 – Educational Background & Turning a Hobby into a Career
8:15 – Mastering the YouTube Algorithm & Starting from Zero
14:25 – From 9–5 Grind to Seven Figures
24:49 – Content Strategy
29:37 – Building the Ecosystem: Apps & Brand Partnerships
35:57 – Converting Followers into Sustainable Revenue
38:54 – Biohacking Realities & The Truth About Supplements
40:47 – Adapting as Your Audience Matures
43:05 – Real Estate & The Villa Lipsett Project
48:16 – The Future of Fitness & Building a Legacy
52:56 – Final Thoughts

Resources & Links:

• Instagram @roblipsett
• Buzzsprout/Podcast: Listen on Apple Podcasts, Spotify, Google Podcasts: https://strippingoffwithmatthaycox.buzzsprout.com
• Follow Stripping Off on YouTube

Enjoyed this episode? Please subscribe to Stripping Off with Matt Haycox and leave a ★★★★☆ review on Apple Podcasts or Buzzsprout – it really helps others find us!