Kevin O'Leary's Mom Shaped His Investment Strategy When He Was 7, Saying 'Boys, Never Spend The Principal, Only The Interest'

In a recent LinkedIn post, renowned investor and Shark Tank star Kevin O’Leary shared the unwavering investment principles that have guided his financial decisions throughout his career. O’Leary’s approach is simple yet powerful: invest only in assets that generate a steady stream of income through dividends or interest.

O’Leary’s investment philosophy is deeply rooted in the lessons he learned from his mother at a young age. He recalls her taking him and his brother to the bank to buy bonds, where she would impart the wisdom of never spending the principal and only living off the interest. This early lesson has become the cornerstone of O’Leary’s investment strategy.

In his own words, O’Leary views his portfolio as a “chicken on a spit dripping cash.” Every investment he makes, whether it’s a fixed-income position or an equity, must generate a yield. The cash flow generated from his investments is then used to support his family’s lifestyle and charitable commitments.

O'Leary says he keeps his family's wealth parked in two ETFs, calling them "the backbone" of his family trust: ALPS O’Shares US Quality Dividend ETF OUSA, which cherry-picks the highest quality balance sheets with positive cash flow from the S&P 500, and ALPS O’Shares US Small-Cap Quality Dividend ETF OUSM, which weeds out underperforming companies from the Russell 2000. These holdings provide distributions each month while providing market returns.

Two Alternative Investments That Generate Plenty Of Yield

For investors looking to adopt O’Leary’s cash flow-focused approach, two compelling investment options are the Ascent Income Fund and Basecamp Alpine Notes from EquityMultiple.

The Ascent Income Fund targets stable income from senior commercial real estate debt positions, offering a historical distribution yield of 12.1% backed by real assets. With payment priority and flexible liquidity options, the Ascent Income Fund is a cornerstone investment vehicle for income-focused investors. First-time investors with EquityMultiple can now invest in the Ascent Income Fund with a reduced minimum of just $5,000. 

Click here to learn more about the Ascent Income Fund and start generating a reliable stream of cash flow.

Basecamp Alpine Notes from EquityMultiple offer another powerful short-term cash management tool, with a target APY of 9.00% over a 3-month term and a minimum investment of only $1,000. These notes provide high liquidity and compelling rates with compounding interest, making them an ideal choice for investors looking to build their real estate portfolio while generating steady income. 

Click here to learn more about what makes Basecamp Alpine Notes an attractive high-yield investment.

In today’s unpredictable markets, Kevin O’Leary’s investment mantra of focusing on cash flow is more relevant than ever. By investing in assets that generate a steady stream of income, like the Ascent Income Fund and Basecamp Alpine Notes, investors can build a resilient portfolio that can weather market volatility and support their financial goals. As O’Leary puts it, “Cash flow is king, my friends.”