In a captivating episode of Millennial Investing, host Robert Leonard interviews James Altucher, a multifaceted figure renowned as a prolific writer, serial entrepreneur, chess master, and venture capitalist. Altucher's candid discussion spans his colorful career, marked by significant highs and devastating lows, and distills invaluable lessons for entrepreneurs and investors alike.
Altucher’s journey defies traditional career paths. Starting with a computer science background, he transitioned from programming for HBO to launching a successful web development company in the early internet era of the mid-90s. He recalls the nascent internet space, where knowing HTML and basic programming made one a pioneer. His company built some of the first major corporate websites, like AmericanExpress.com, though he admits his initial lack of business acumen meant he sold his company as a "glorified ad agency" rather than a higher-valued "software company."
His early success, however, was followed by repeated financial ruin. After selling his first company for $15 million, overconfidence led him to invest heavily in stocks and private companies without sufficient knowledge, ultimately losing nearly everything, down to $143 in his bank account. This cycle of making and losing money repeated for 11 years. Altucher attributes these failures to arrogance and a lack of humility in the face of the market. These experiences, however, forged his "daily practice"—a commitment to improving physical, emotional, creative, and spiritual health—which he credits for his ability to bounce back each time.
Driven by an obsessive interest in investing after his losses, Altucher embarked on an unusual path to becoming a hedge fund manager. Lacking traditional finance credentials, he consumed hundreds of books, studied market history, and wrote software to analyze trading strategies. His track record and articles for financial publications helped him gain recognition and raise money for a hedge fund, and later a fund of hedge funds. He learned that unlike entrepreneurship, where one can control product development and sales, the stock market's unpredictability makes hedge fund management inherently stressful. The final straw for his hedge fund career came when a potential investor, citing the reputational risk of "Bernard Madoff Securities" being on the front page, declined to invest in him. This incident pushed Altucher to pivot to other ventures, including investing in private companies like Facebook ad agencies.
Altucher's core philosophy revolves around "choosing yourself." This means not waiting for permission or validation from traditional gatekeepers (publishers, networks, employers) but actively pursuing one's ideas. He exemplified this by self-publishing his successful book, "Choose Yourself," and highlights how technology empowers individuals to create and distribute their work independently. This philosophy emphasizes self-reliance, continuous learning, and maintaining personal well-being as foundational for any form of success.
When asked for his number one investment pick, Altucher unequivocally states that it's investing in *yourself*. He illustrates this with stories of billionaires like Richard Branson and Damon John, who made bold, self-directed moves rather than simply investing in external assets. Altucher argues that acquiring new skills, even small ones, offers unparalleled returns. He shared a personal example of taking a photography class: "If you do just one wedding next year, you made 200% on your investment."
Host Robert Leonard concurred, reinforcing the idea by sharing his own experience of getting a real estate license for a few hundred dollars, which quickly yielded thousands in referral commissions. He emphasized that this principle applies even to corporate careers, where investing in skills can lead to higher salaries and career advancement.
In the listener Q&A segment, Robert addressed a millennial investor's question about portfolio allocation for long-term, risk-adjusted returns. He stressed that the answer is highly personal, depending on goals, risk tolerance, and involvement level. For those seeking lower risk or less involvement, he suggested a 90/10 or 80/20 split between low-cost broad market stock ETFs (like VTI) and bond ETFs (like BND), or using target date funds. For his own portfolio, with a 30-40 year horizon and high-risk tolerance, Robert employs a 50% ETF allocation (mostly S&P 500 and tech ETFs) and 50% in concentrated individual stock picks, actively managing with options. He concluded by reiterating that there's no perfect universal allocation, but understanding one's personal circumstances is key.