5 Luxuries Rich Founders Don’t Regret Buying

SUMMARY

Producer Jackie Lamport, of the Moneywise podcast for high-net-worth founders, details the five most valuable luxury purchases that radically enhance quality of life, based on interviews with over 150 successful entrepreneurs.

STATEMENTS

Making money is one thing, and often considered the easy part by high-net-worth founders; the challenge is figuring out what to do with the wealth that follows.
The perceived luxuries of fast cars, designer clothes, and watches often don't translate to feelings of contentment or authenticity, and everything purchased incurs more responsibility.
Luxury purchases that founders consistently swear by—those that change how they live, work, and feel—are surprisingly practical and center around buying back time and maintaining health.
Buying back time involves outsourcing tedious or unenjoyable tasks through services like housekeepers, private chefs, and assistants, freeing up time for personal enjoyment, family, or work maximization.
Removing household friction by outsourcing tasks can be a significant benefit in personal relationships, avoiding disputes over chores and responsibilities.
High-end health investments, particularly personal trainers, are consistently deemed worth the money because they ensure accountability and proper structure for physical exertion.
Investing in a home gym is repeatedly cited as a worthwhile expense, even by modest spenders, as it reduces friction and increases commitment and consistency with workouts.
Preventative and high-end concierge healthcare is a valuable investment—even spending up to $100,000 annually—due to the general lack of focus on preventative health in standard systems.
A "dream home" is primarily valuable not for its financial return on investment (ROI), but for its return on happiness, serving as a gathering place to create shared memories and align wealth with personal values.
The most impactful personal spending category for founders is universally reported to be travel and experiences, prioritizing them over material goods.

IDEAS

The ultimate luxury purchase for successful founders is functionally "buying back time" by outsourcing routine tasks, which addresses the subsequent challenge of optimizing post-wealth life.
The emotional ROI of a dream home surpasses its financial ROI, as its primary purpose is to be a space for memory creation, community building (like founder dinners), and sharing wealth with loved ones.
Discipline and the willingness to do hard things are viewed as a source of "massive dopamine release" and are crucial for being a well-rounded person, which outsourcing risks hindering.
There is a "kid-spoiling risk" associated with extreme convenience, where children might not value discipline or understand that living in luxury (e.g., a home sleeping 45 with a private chef) is not normal.
For the ultra-wealthy, the feeling of "I made it" is often achieved not through traditional status symbols like big houses or fancy cars, but through the ability to fly business class or private, ensuring bodily comfort and reduced friction during travel.
The caveat for buying back time is the risk of accidentally eliminating restorative, meditative moments—like cooking or cleaning—that one didn't realize were beneficial.
While many health hacks are "money grabs," the universally approved preventative health investment is a personal trainer, focusing on accountability and effort, which is seen as a necessary part of good health.
Meaningful experiences are defined by intention—designing them around connection and curiosity as opposed to status or flashiness—and aligning them with one's personal values.
A very large home can swiftly transform into a part-time job due to the intensive time required for maintenance, contractor oversight, insurance, property taxes, and furnishing.
For some high-net-worth individuals, their sole spending priority shifts entirely to experiences over comfort following major life events, such as a spouse's illness and recovery.

INSIGHTS

The genuine measure of success for high-net-worth founders pivots from merely accumulating wealth (the easy part) to strategically deploying it to minimize friction, protect time, and maximize emotional well-being.
True value in luxury spending is derived from resources that simplify life and reduce physical stress—like optimized travel and personalized healthcare—rather than expenditures intended purely for external validation or status display.
The most significant long-term investments founders make do not have a financial return, but a return on happiness (ROH), which links wealth expenditure directly to core personal and familial values.
There is a subtle but critical trade-off in "buying time": while removing friction is beneficial, completely eliminating unenjoyable tasks risks eroding personal discipline and the appreciation for restorative hard work.
Experiences, particularly travel, are the primary vehicles used by successful individuals to convert wealth into lasting memories and shared joy, solidifying connection over ephemeral material ownership.
The pattern of worthwhile luxury purchases indicates a collective shift among founders toward internal metrics of life quality—health, time, peace, and meaningful relationships—as opposed to external symbols of affluence.

QUOTES

"everything that you buy is another thing that you're responsible for."
"Discipline is one of those things that just I feel like it's a massive massive dopamine release when you do something hard."
"how I try to frame investments now is return on happiness and investing in building my dream home."
"I never wanted wealth for things. I wanted wealth for memories, for and that creates them."
"The pattern here is that the things that are worth it are the things that give you time and make you healthier and make your life feel more memorable and calm."

HABITS

Strategically outsourcing tedious or unenjoyable chores to professional services (housekeeper, chef, assistant) to reclaim mental and physical time.
Engaging a personal trainer for consistent, accountable, and personalized physical health maintenance, regardless of high net worth.
Prioritizing family and personal preventative health by investing significant funds in high-end concierge medical services, including continuous advanced testing.
Actively designing travel and experiences around connection, curiosity, and shared memories, rather than passively engaging in large, status-driven trips.
Consistently opting for business or first-class air travel for any non-short flights to ensure physical comfort and eliminate bodily pain associated with long trips.

FACTS

A specific home mentioned in the discussion required approximately 5 to 10 hours per week of oversight for maintenance, contractors, and proposals.
One founder spent $100,000 annually on concierge health services for his extended family because preventative care is not prioritized in standard healthcare systems.
The majority of high-net-worth founders surveyed in a "wealth report" identified travel and experiences as their number one personal spending item.
One founder detailed plans to spend close to half a million dollars on experiences in a single year post-recovery from a spouse's illness.
Brian Johnson claims to have the best biomarkers of anybody on planet Earth, operating his health journey in a league far above standard biohacking.

REFERENCES

Hampton (joinhampton.com)
Lower Street (lowerstreet.co)
Daily Body Coach (Anthony)
Dr. Becky (parenting expert)

HOW TO APPLY

Identify all tedious or unenjoyable tasks in your routine (e.g., cooking, cleaning, administrative work) and commit to outsourcing them immediately to buy back significant blocks of personal time.
Invest dedicated funds into physical and mental health resources, specifically obtaining a personal trainer for accountability and a therapist for mental wellbeing, rather than focusing on temporary "bio-hacks."
Reframe costly potential investments, such as a major home purchase or renovation, by prioritizing its "Return on Happiness" (ROH) and focusing on its capacity to foster community and family memories.
When planning travel, consciously design experiences with the intention of maximizing connection and curiosity rather than focusing on status or simply checking off a destination, ensuring alignment with core personal values.
Upgrade air travel to business class or higher for almost all long-haul flights, viewing this expenditure as a necessary cost to prevent physical stress (back and knee pain) and safeguard long-term health.

ONE-SENTENCE TAKEAWAY

Worthwhile luxury for the wealthy is highly practical, prioritizing time, health, reduced friction, and meaningful experiences over material status symbols.

RECOMMENDATIONS

Re-evaluate all current spending to ensure it is aligned with maximizing frictionless living and the return on happiness, rather than accumulating objects that increase responsibility.
Establish a firm boundary against allowing extreme domestic outsourcing to eliminate all difficulty, ensuring children and oneself maintain discipline and exposure to necessary challenges.
Prioritize and consistently budget for high-end preventative healthcare services for the entire family, recognizing the systemic shortcomings in standard wellness paradigms.
Before making a major purchase like a "dream home," meticulously calculate the time commitment required for maintenance and oversight, factoring in that cost before retirement.
Actively seek and integrate experiences into life that facilitate deeper connection and understanding of the world, following a pattern of intentionality instead of hollow adventure trips.

MEMO

The New Calculus of Affluence: Why Founders Are Trading Ferraris for Frictionless Living

The traditional symbols of extreme wealth—the fast cars, the designer watches, the massive estates—are increasingly being dismissed as superfluous burdens by the very people who can afford them. According to insights gleaned from over 150 interviews with high-net-worth founders, the true luxury is not accumulation but optimization. Making money, many admit, was the relatively easy part; the complex, ongoing challenge is figuring out how to spend it to genuinely improve daily life. This has led to a counterintuitive truth: the most valued purchases are the surprisingly practical ones that fundamentally alter how founders live, work, and feel, focusing overwhelmingly on reclaiming time, optimizing health, and elevating experiences.

The number one priority is functionally buying back time. This manifests in aggressively outsourcing chores—hiring private chefs, housekeepers, and personal assistants—to eliminate the "tedious or unenjoyable." The rationale extends beyond personal enjoyment; it's about removing household friction that strains relationships and freeing up mental space previously consumed by minor logistical worries. Yet, a crucial caveat exists: the risk of becoming too frictionless. Founder wisdom suggests that eliminating all forms of discipline and hard work risks diminishing one's appreciation of labor and, more importantly, raises the risk of raising entitled children who fail to see the necessity of effort.

Beyond time, high-end health investments are consistently deemed non-negotiable. While many bio-hacks are dismissed as fleeting trends, the commitment to personal trainers and comprehensive, preventative concierge healthcare is paramount. Founders, some spending six figures annually, prioritize securing advanced health services for their entire extended families, driven by the belief that standard healthcare systems neglect proactive prevention. Similarly, investment in a dream home is not viewed through the lens of maximizing financial return on investment (ROI), but rather achieving a "return on happiness" (ROH). These homes serve as gathering places for family and community, designed to facilitate shared memories and align wealth with intrinsic values, although they carry the risk of becoming a time-consuming "part-time job" in maintenance.

Finally, the shift away from material goods culminates in the prioritization of meaningful experiences and travel. Data confirms that travel and experiences are the single largest spending category for this demographic. The focus herein is on intentionality: experiences must be designed around connection and curiosity, not status. This principle also governs the ultimate convenience luxury: high-end travel. The ability to guarantee physical comfort and avoid body strain by flying business or first class is often cited as the truest feeling of having "made it," symbolizing