Dave Portnoy (founder of Barstool Sports and known for his outspoken trading commentary on “Davey Day Trader Global”) has been actively deploying capital into cryptocurrency, particularly during market downturns.
He follows a contrarian “buy when there’s blood in the streets” strategy, often referencing Warren Buffett’s philosophy of being greedy when others are fearful. Portnoy he’s continuing to buy crypto amid price drops: He posted: “Pouring dry powder into crypto. The more it falls the more I buy. The more uncomfortable I get the better I feel. Chaos is a ladder.” He emphasized this is not investment advice.
On January 31, 2026, he mentioned: “Just keep buying crypto right? It’s getting uncomfortable. I think that’s when you need diamond hands.” On January 30, 2026, he shared a video stating “Crypto is crashing but I’m still buying.”
Reports indicate a specific recent purchase during a crypto sell-off: He bought approximately $1 million worth of XRP around $1.79 per token and $500,000 worth of Bitcoin around $82,000 per BTC. This adds to prior positions, with him declaring he’d “keep buying” if prices continue falling.
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In November 2025, he announced buying $2 million in crypto during a pullback: roughly $1 million in XRP (split buys), $750,000 in Bitcoin, and $400,000 in Ethereum. Other instances include a $1.5 million bet in April 2025 ($1 million XRP + $500,000 BTC), and he has referenced holding positions like $1.5 million in BTC and $1.3 million in XRP as far back as late 2024.
Portnoy often uses Kraken for trades, he’s partnered with them for content like Bitcoin Pizza Day promotions and frames these as high-conviction moves during fear-driven dips. His posts frequently highlight XRP alongside Bitcoin, drawing attention in crypto communities.
Note that crypto markets are volatile, and Portnoy’s actions are personal/high-profile but not professional financial advice—he disclaimers that in his posts. His involvement has sparked mixed reactions, from praise for conviction to skepticism about timing or influence on retail traders.
Dave Portnoy’s XRP investment strategy is centered on contrarian, dip-buying during periods of market fear and price declines. He frequently invokes Warren Buffett’s famous advice to “be greedy when others are fearful” or “buy when there’s blood in the streets,” treating sharp crypto sell-offs as prime opportunities for accumulation rather than panic selling.
Portnoy positions himself as a high-conviction holder with “diamond hands” during discomfort, emphasizing that the more prices drop and the more uneasy he feels, the stronger his urge to buy. He deploys significant capital often in the $1M+ range per trade into XRP when prices fall sharply, viewing volatility and crashes as ladders to climb rather than reasons to exit.
Portnoy has repeatedly highlighted XRP for its potential for outsized gains e.g., “10X” potential compared to Bitcoin’s more limited upside in his view. He sees it as a speculative, gambler-friendly asset tied to Ripple’s ecosystem developments like stablecoins, often pairing it with BTC and sometimes ETH.
He admits to being “always late” to runs but bets big anyway, holding long-term rather than day-trading. He uses platforms like Kraken for execution and often shares screenshots or videos of trades. Every public post includes disclaimers that this is personal conviction, not professional guidance.
He embraces discomfort—”the more uncomfortable I get, the better I feel”—and references chaos as opportunity. Built significant positions, including a $1M+ buy during a dip around February 2025, describing it as a high-risk, high-reward bet on XRP’s potential.
In mid June 2025 he sold his entire XRP bag valued at ~$3M at ~$2.40 based on advice from an “XRP guy” advisor concerned about external factors like stablecoin competition. XRP then surged dramatically to new highs like $3.65+, leading Portnoy to publicly regret it (“sick to my stomach,” “I want to cry,” missed millions).
Re-entered aggressively during a market crash, buying ~$1M in XRP (split buys), plus BTC and ETH, totaling ~$2M. He framed it as shark-like predation on weakness. Continued accumulation amid ongoing downturns in February 2026. Key buys include: Late January: ~$1M XRP at ~$1.79 + $500K BTC at ~$82K, adding to prior positions.
He repeatedly posted “Just keep buying crypto… It’s getting uncomfortable… diamond hands” and “I’ll keep buying” if prices drop further. As of early February 2026, his disclosed XRP exposure appears to have rebuilt substantially, often alongside BTC. He has referenced past holdings like $1–2M+ in XRP at various points, but exact current totals aren’t publicly itemized beyond trade announcements.
Portnoy’s strategy draws mixed reactions: praise for bold conviction and retail inspiration during fear, but skepticism over timing and influence on followers. Crypto remains highly volatile, and his moves are personal/high-profile rather than diversified professional investing. He often ties XRP enthusiasm to broader crypto optimism but treats it as his favored “moonshot” play.