Kevin O'Leary is urging entrepreneurs to rethink what success looks like, arguing that flashy valuations and social media clout matter less than building and protecting a sizable cash cushion.
O'Leary Says Success Starts With Liquidity Discipline
"Most entrepreneurs think success is about valuations, followers, or the next big idea. It's not," O'Leary wrote Sunday in a post on X.
He added, "The real test is simple: Do you have $5 million liquid that you never touch? That's the discipline most founders never build. They double down on risky ideas, over-invest emotionally, and then wonder why they're broke at 65. Financial freedom comes from one thing, protecting the nest egg. Touch the income, never touch the principal."
Five-Million-Dollar Nest Egg As Freedom Benchmark Target
The "Shark Tank" investor has pushed the $5 million benchmark before. In a December 2024 interview with the Financial Post, he called that sum "the minimum" needed for true personal freedom and said it was "very, very, very hard to get," arguing that at that level, work becomes optional rather than compulsory.
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O'Leary stresses that the money should be kept in secure, liquid form, not in real estate, or in stocks, as he has put it in earlier interviews, pointing to cash and short-term government debt as his preferred vehicles.
At current yields near 5% on Treasury bills and similar instruments, a $5 million reserve could generate roughly $250,000 a year in interest, which he says can be spent while the principal remains untouched.
Entrepreneurs Urged To Prioritize Safety Before Risk
In a video clip attached to Sunday's post, O'Leary said he frequently tests founders' claims of success by asking whether they have $5 million in Treasury bills and that "nine times out of ten" they do not, reinforcing his view that many entrepreneurs overestimate their financial security.
O'Leary has previously told investors that once they reach a major financial milestone, they should first lock that amount into safe, liquid assets such as T-bills before taking on new high-risk bets.
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