Deep Dive
What was Scott's worst purchase?
Scott considers his first cars to be his worst purchases. They consumed all his disposable income and more, costing $2500, equivalent to $10,000 today adjusted for inflation, for the car itself plus insurance at age sixteen.
WHY does Scott prefer spending money on experiences?
Scott learned, through a health scare and subsequent trip to Europe, that experiences create lasting memories, unlike material possessions. He cites his European backpacking trip at age 24 as his best expenditure ever.
What does Scott consider his best purchases?
Scott's best purchases, both financially and emotionally, were his homes. His first home symbolized commitment and domestic bliss, while his last home, purchased in 2017 for 9.5 million (against an asking price of 15 million), significantly appreciated in value, particularly during the COVID pandemic.
What category of spending does Scott refuse to skip on?
Scott spends lavishly on travel, often inviting friends to join him and covering their expenses. He attributes this generosity to his difficult relationship with his frugal father.
WHY is Scott so generous with his spending?
Scott's generosity stems from his childhood experiences with his "painfully cheap" father. He vowed to be different if he ever became wealthy, enjoying his money and sharing it with others.
How does Scott handle splitting the check at a restaurant with friends?
With younger friends, Scott prefers splitting the check evenly or using payment apps. With older, more financially secure friends, he suggests couples or individuals taking turns paying for the entire meal.
How does Scott approach gift-giving during the holidays?
Scott prioritizes meaningful gifts like notes, books, or framed pictures over material possessions. He dislikes excessive consumerism and prefers giving gifts randomly rather than solely on holidays or birthdays.
WHY does Scott consider employee gifts strategic?
Scott views employee gifts as strategic because they are pre-tax, more meaningful than cash bonuses, and enhance employee morale. He prefers giving gifts rather than simply increasing compensation.
What is Scott's approach to "essential" spending?
Scott emphasizes ensuring spending lags behind income to avoid the pain of downsizing. While he enjoys his private plane, he acknowledges the importance of financial security to maintain such a lifestyle.
Has Scott ever downsized his lifestyle due to financial constraints?
Yes, after the 2008 financial crisis, Scott had to sell his New York loft due to financial losses. He found this experience humbling, highlighting the importance of financial responsibility.
WHY is philanthropy essential to Scott?
Scott believes hoarding wealth is unnecessary. He chooses to either spend or give away any excess income beyond what he needs for a comfortable life, supporting causes like mental health and vocational training.
What does Scott's spending reveal about him?
Scott's spending reflects his generosity, focus on experiences, and commitment to family. He acknowledges his indulgences and desire to impress others, but emphasizes the importance of aligning spending with values.
- Car ownership was essential for social life in Los Angeles during Scott's youth.
- Scott's first car purchases created significant financial strain.
- Scott views his early car purchases as his worst financial decisions.
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