Ajay Gupta built a wealth management firm to over a billion dollars, sold his stake at 49, and launched a family office with Tony Robbins. He joins Tom Ruggie to discuss how he evaluates private investments, why he wants to be paid for giving up liquidity, and what he means by quality time remaining.
How much of a portfolio should be illiquid? Ajay Gupta’s answer depends on two numbers that are difficult to know with certainty and one condition that can change the calculation entirely.
Ajay is Principal of Robbins Gupta Holdings, the family office he and Tony Robbins run together as partners. His path there began with two reinventions. At 29, he left a wealth management practice in Montreal and moved to San Diego with no clients and no network. At 49, he sold 100% of his stake in the firm he had spent 25 years building.
When Ajay called Tony to say he was retiring, Tony told him he was not retiring. He was rewiring. Three and a half hours later, they began building a family office together.
In Episode 28, host Tom Ruggie and Ajay discuss what changed when Ajay began investing his own capital instead of advising on someone else’s. Ajay explains how he thinks about liquid and illiquid assets, why net worth affects that balance, and why the liquid side of his portfolio consists largely of low-cost index funds.
On the private side, he shares why he often prefers owning part of the firm managing the money rather than only investing in its funds. He also recounts the meeting where that idea first came together, including the moment when he nearly ended the call before the opportunity became clear.
Tom and Ajay also compare their current views on real estate. Ajay is buying. Tom is waiting.
The conversation moves beyond portfolios to longevity, advanced diagnostic testing, sleep, and the shift from counting hours worked to paying closer attention to health. Ajay closes with what the significance of wealth means to him at 55, and the three things he believes are difficult to hold at the same time.
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