O’Leary vs. Saylor: Crypto Strategy Showdown

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Kevin O’Leary and Michael Saylor Clash Over Bitcoin Strategy as Ethereum Gears Up for Major Upgrade

KevinOLearyKevin O’Leary, the entrepreneur best known from Shark Tank, recently pushed back on Michael_SaylorMichael Saylor’s bold Bitcoin strategy. Saylor, chairman of MicroStrategy, has been a vocal advocate for using company funds—via share and debt sales—to build massive Bitcoin holdings. O’Leary, however, doesn’t believe the U.S. government will ever adopt a similar approach.

Speaking candidly, O’Leary said there’s virtually no chance Congress—whether led by Democrats or Republicans—would approve a national Bitcoin reserve. He called the idea politically unrealistic, regardless of how bullish the crypto community feels.

That doesn’t mean he’s anti-crypto. Far from it. O’Leary sees digital assets as a growing part of the global economy. But he’s betting on stablecoins like USDC, not Bitcoin stockpiling. In his view, regulated stablecoins could revolutionize international payments by offering speed and cost savings traditional banking systems can’t match.

“Wire transfers can cost up to 2%,” O’Leary said. “Stablecoins can do the same thing for a fraction of that—more like 0.01%.” He also disclosed he’s personally invested in USDC, along with major crypto firms like Coinbase and Robinhood.


The “Bitcoin Reserve” Bill in Congress

One piece of legislation making waves in D.C. is the Cynthia Lummis Bitcoin Bill, which proposes the U.S. government purchase 200,000 Bitcoin each year for five years—paid for by selling existing gold reserves, not taxpayer dollars. The Bitcoin would be held for at least 20 years.

O’Leary doesn’t expect the bill to go anywhere. But despite his skepticism, support for crypto on Capitol Hill is growing. The House now has a clear pro-crypto majority, while the Senate is slowly warming up.

States are also making moves. New Hampshire recently approved a law allowing the state to allocate up to 5% of public funds into digital assets—limited to cryptocurrencies with a market cap above $500 billion. At present, that means only Bitcoin qualifies, though Ethereum could meet the threshold in the future.


Ethereum’s Major Upgrade Rolls Out May 7

Ethereum, the second-largest cryptocurrency by market cap, is set for a key technical upgrade on May 7. The so-called “PCRA Upgrade” introduces two Ethereum Improvement Proposals (EIPs) that target usability and staking efficiency.

EIP-7702: Smarter, Simpler Wallets

This update enables Ethereum user accounts to behave more like smart contracts.

That means users could:

  • Pay gas fees in tokens other than ETH
  • Bundle multiple actions into a single transaction
  • Enjoy easier wallet recovery

The goal is to simplify Ethereum wallets, particularly for newcomers to the ecosystem.

EIP-7251: Bigger Staking Batches

Right now, Ethereum staking is limited to 32 ETH per validator. The new upgrade raises that ceiling dramatically—to 2048 ETH. This change appeals to large financial players, as it reduces the number of validators they need to manage. But it also raises concerns about potential centralization.


Stablecoin Regulation Could Arrive by August

Lawmakers are also working on a long-awaited stablecoin framework. O’Leary expects legislation to pass before August. While Senate Democrats have pushed for stricter rules around fraud prevention and financial transparency, progress is ongoing.

The goal of the legislation is to ensure stablecoins are fully backed by reserves and subject to government oversight. If passed, it could boost mainstream and international adoption of stablecoins. O’Leary is optimistic, particularly given his investment in USDC, and sees stablecoins playing a key role in the future of finance.


The Bottom Line

Michael Saylor and Kevin O’Leary represent two very different visions for crypto’s future in the U.S. One wants Bitcoin as a national asset; the other is focused on regulated digital dollars and private-sector innovation.

Meanwhile, Ethereum continues to evolve with a major upgrade designed to improve efficiency and user access. With new state-level crypto policies and national legislation on the table, 2025 is shaping up to be a critical year for digital asset regulation and adoption.

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