Some ideas sound ridiculous—right up until they turn into trillion-dollar companies. Tesla (TSLA) was once one of them in the eyes of many investors, including “Shark Tank” investor Kevin O’Leary.
In a 2020 interview with CNBC, O’Leary said, “If Elon Musk came into the ‘Shark Tank’ and told me to invest in his electric car company before he started it, I would say, ‘You’re crazy.’” He added in a related segment, “But Elon, I still would have said, ‘no,’ to you in the ‘Shark Tank.’ Your idea was way too crazy. Right!”
A Pitch That Sounded Too Early
At the time, the skepticism tracked with how O’Leary invests. He has long favored companies with earnings, discipline, and a clear path to returns. Early Tesla didn’t fit that mold. The company was scaling aggressively, posting losses, and trading at valuations that made traditional investors uneasy. O’Leary even considered shorting the stock.
From the outside, Tesla looked like a car company struggling to prove it could turn a profit. That framing shaped the decision.
The Conversation That Changed Everything
The turning point came from inside the company.
In 2019, Tesla engineer Trevor O’Leary was interning as an electrical engineering student. After working there, he challenged his father directly. O’Leary recalled telling him he wanted to short Tesla because “it’s such a joke.” Trevor responded, “No, Dad, you’re the joke. I work there, you don’t understand.”
That exchange reframed the business.
Trevor argued Tesla was not just building cars. It was building a data-driven technology platform. Every mile driven feeds information back into its systems, improving autonomous driving over time. O’Leary told CNBC, “My son went to work for Tesla as an intern and convinced me that it wasn’t a car company I was investing in, it was a data technology company.” He added, “Every mile driven globally, [Tesla’s] data gets smarter, the resolution better. This company is all about the future of autonomous driving.”
Hearing that perspective from someone inside the company shifted the thesis.
When The Facts Changed, So Did The Bet
O’Leary changed course and bought shares, stepping away from the idea of shorting the stock. The timing worked in his favor. By mid-2020, Tesla had become one of his best-performing investments.
Reflecting on that decision, he said, “When facts change, I change. My young electrical engineer son talked me into buying a stock I had no interest in.”
Even Musk acknowledged the moment publicly, offering praise for Trevor’s perspective.
Since then, O’Leary has shifted from skeptic to supporter, often pointing to Tesla’s execution and engineering strength. In a 2024 interview on Fox Business’s “The Big Money Show,” he said, “I am a huge fan of Elon Musk, and for full disclosure, my son works for him and loves his job at Tesla.”
The broader message is clear. Early ideas that look unreasonable at first can look obvious with better information and time. Tesla didn’t fit a traditional checklist, but it wasn’t trying to.
In hindsight, the call looks simple. At the time, it didn’t.
On the date of publication, Jeannine Mancini did not have (either directly or indirectly) positions in any of the securities mentioned in this article. All information and data in this article is solely for informational purposes. For more information please view the Barchart Disclosure Policy here.
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