Is MicroStrategy’s Michael Saylor joining the Trump administration?

Michael Saylor, the executive chairman and co-founder of MicroStrategy, might be adding a new title to his repertoire—crypto advisor in Donald Trump’s administration.

Saylor has reportedly met with several members of the incoming administration but is keeping tight-lipped about specifics. When asked directly whether he had met Trump, Saylor replied, “I have met with a lot of people in the incoming administration, but I could not comment further than that.”

The possibility of him stepping into a government role has gained traction, especially after there are expectations for a crypto advisory council under Trump.

“If I’m asked to serve on some digital assets advisory council, I would probably do so,” Saylor said. This aligns with his long-standing commitment to influencing crypto policies both publicly and privately.

MicroStrategy’s Bitcoin obsession keeps growing

While political rumors swirl, Saylor’s company, MicroStrategy, continues its Bitcoin-buying spree, making headlines for its aggressive strategy. Over six straight weeks, MicroStrategy has acquired Bitcoin worth $45 billion, solidifying its position as the largest corporate Bitcoin holder.

The timing couldn’t be more perfect, as the company prepares for its inclusion in the Nasdaq 100 index next week. Interestingly, MicroStrategy’s stock performance this year has outpaced Bitcoin itself, driven by retail investors and hedge funds seizing on market volatility.

MicroStrategy’s obsession with Bitcoin is anything but subtle. While the company started as a software firm in 1989, it now operates more like a Bitcoin treasury. Saylor confirmed the shift in focus, saying, “Our primary method of generating shareholder value is through our treasury operations.”

In October, MicroStrategy announced plans to raise $42 billion over three years. However, with overwhelming market enthusiasm, Saylor hinted they could hit this target by January. “The equity capital markets were very enthusiastic over the past four weeks,” he said.

With $7.2 billion in convertible debt already on their books, the company plans to lean more on fixed-income markets moving forward. Saylor explained that this is meant to build “more intelligent leverage” for the benefit of shareholders.

He also addressed how MicroStrategy buys Bitcoin without moving the market. Using regulated exchanges like Coinbase and specialized algorithms, the company ensures its purchases remain discreet. “Our goal is to not be noticed by the market,” he said.

Saylor’s view on Bitcoin, accounting rules, and corporate adoption

Saylor has long championed Bitcoin as a superior financial asset, but he believes its true potential is just beginning to unfold. Recent regulatory changes and political changes have created a favorable environment for Bitcoin adoption, according to him.

He pointed to the November 1st election results, calling them a “sea change” for the industry. With fair value accounting for Bitcoin becoming mandatory in 2025, Saylor expects this to be a turning point for corporate adoption.

“For the first time in 100 years, large public companies have a capital asset they can consider in lieu of Treasury bills, and that’s Bitcoin,” he said. The MicroStrategy boss criticized traditional assets like real estate and gold, arguing that Bitcoin is the logical choice for corporate treasuries.

He believes these changes could drive more companies to follow MicroStrategy’s lead, although he acknowledged the infamous rejection he got from Microsoft.

He recently pitched to their board on investing in Bitcoin. “Microsoft’s strategies are conventional—buying back their own stock and parking cash in Treasuries,” he said. Still, he remains optimistic that broader adoption will come as accounting rules and regulatory clarity improve.

MicroStrategy’s Bitcoin holdings have already delivered substantial returns. The company has generated $18.6 billion in unrealized investment income this year, and Saylor expects this figure to grow significantly with fair value accounting.

By 2025, he projects $10 billion in annual investment income, positioning the company for inclusion in the S&P 500. “When we adopt fair value accounting and Bitcoin goes up 20% a year, we’ll be generating billions annually in investment income,” he explained.

MicroStrategy’s controversial identity and shareholder value

Despite its transformation into a Bitcoin powerhouse, MicroStrategy hasn’t abandoned its software roots. The company’s software division generates $75 million in annual operating income and remains profitable. Saylor called it a “core part of the company’s identity,” adding that they have no plans to spin it off.

However, the numbers speak for themselves: the bulk of shareholder value now comes from Bitcoin-related activities. Saylor broke down the three ways MicroStrategy creates value: operating income, investment income, and acquisition income.

This year alone, Bitcoin-related operations have added $14.4 billion in benefits to shareholders. The company’s strategy of issuing equity and debt to acquire Bitcoin has proven highly lucrative, and he sees no reason to slow down.

As MicroStrategy prepares for its Nasdaq 100 inclusion, questions remain about its next steps. Saylor hinted that they might explore selling newly issued stock to index trackers, depending on market conditions. “When we execute the ATM, we sell equity into the market if we like the price and terms,” he said.

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