Dave Portnoy, the outspoken Barstool Sports founder, has offered a rare moment of reflection—this time not about sports or scandal, but investing.
After years of stock market banter and financial consultations, Portnoy now wonders if the smartest move all along was just buying Bitcoin and holding tight.
In a post shared on July 14, he admitted that endless daily strategy sessions with his advisor may have been a distraction from the obvious winner: BTC. With Bitcoin recently rocketing past $123,000 before settling just under $120K, Portnoy’s frustration with traditional investing seemed to hit a peak.
“Forget the back-and-forth,” he wrote in paraphrased terms. “We should’ve just gone all in on Bitcoin.”
The irony? He already holds over $5 million in crypto—but as the market surges, even that feels underwhelming to him.
Portnoy’s financial journey has never followed a straight line. From picking stocks out of a Scrabble bag to betting big on Tesla, his investing has always leaned on instinct over analysis. Though his relationship with Bitcoin has been rocky—marked by mistimed buys and one infamous $170K loss on a wrong token purchase—he’s remained engaged with the crypto scene.
Now, as BTC enters new price territory, Portnoy’s realization echoes a broader shift: even seasoned investors are rethinking their playbooks as crypto leaves legacy strategies in the dust.
Kosta Gushterov
Reporter at Coindoo
Kosta joined the team in 2021 and quickly established himself with his thirst for knowledge, incredible dedication, and analytical thinking. He not only covers a wide range of current topics, but also writes excellent reviews, PR articles, and educational materials. His articles are also quoted by other news agencies.
Source: https://coindoo.com/bitcoin-leaves-stocks-behind-and-dave-portnoys-having-regrets/