5 Luxury Purchases That Are Actually Worth It

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Dec 9, 2025

Discover why buying back time with housekeepers and chefs can be the ultimate luxury for founders. Explore the surprising trade-offs of outsourcing household tasks and how investing in fitness pays off. Learn the benefits of concierge healthcare and why experiences often outweigh possessions. From dream homes as sources of joy to upgrading travel for better health, the discussion reveals the true values behind luxury spending. Tune in for insights on making purchases that genuinely enhance life.

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ADVICE

Buy Back Your Time

Buy back time by hiring housekeepers, private chefs, or assistants to remove tedious chores.
Use that reclaimed time for work, family, or restorative activities instead of overfilling your schedule.

ADVICE

Invest In Consistent Fitness

Hire a personal trainer and create a home gym to reduce friction and stay consistent with workouts.
Commit effort to health; shortcuts or passive biohacks rarely replace disciplined work.

ADVICE

Prioritize Mental Health

Prioritize mental health by committing to regular therapy; founders unanimously endorsed it.
Treat coaching and accountability as investments that change behavior and outcomes.

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Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/

Everyone thinks the “rich person” life is about fast cars, fancy watches, and designer flexes. But when we talked to over 150 high-performing founders, the things they actually spend on – and swear by – were surprisingly practical. Some luxuries just look good on Instagram. Others change the way you live, work, and feel every day.

Here’s what we talk about:

The #1 luxury nearly every founder says they’ll never go without again
Why hiring a housekeeper or private chef might save your business (and marriage)
The health investments founders make – and which ones are worth skipping
Why some founders spend $100K/year on concierge medicine for their families
Renting at $17K/month: outrageous flex or return-on-happiness?
The emotional ROI of experiences (and the trip one founder spent $500K on)
Business class vs. private jets: which travel upgrade is actually worth it?
How these purchases impact kids – and the fine line between “comfortable” and “entitled”

Cool Links:

Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/

Sponsors:

Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise
Achieve your dream body with dailybodycoach.com/moneywise
Tame your taxes today at https://olarry.com/moneywise

Chapters:

(1:18) Stuff You Buy vs. Stuff That Matters
(1:58) Buy Back Your Time (Not Just Watches)
(3:04) The Housekeeper Dilemma: Freedom or Softness?
(4:23) Health Hacks: Trainers, Gyms & Biohacking
(6:11) Therapy, Insurance, and the $100K Checkup
(7:22) Dream Homes: ROI on Happiness
(10:53) Experiences > Things: The Data Says So
(12:00) Cancer, Family, and $500K on Memories
(15:13) Connection, Curiosity, and Intentional Spending
(15:33) The Business Class Trap
(16:44) The Real List: What’s Actually Worth It

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Jackie Lamport

Not really the host, but the producer.
Wrote this sentence.