Breakfast with the Bunch: Bitcoin, Belief and Bold Moves

In Conversation with Phong Le, President & CEO of Strategy

A cool and cloudy morning couldn’t dampen the energy at our recent Sydney Breakfast with the Bunch, proudly presented by Strategy.

In conversation with Cycling Exexs MC James Tobin, Phong Le, President and CEO of Strategy, shared the remarkable story of how one of the world’s leading enterprise software companies became the largest corporate holder of Bitcoin.

What followed was a masterclass in strategic reinvention, long-term thinking, and why sometimes the smartest move is also the boldest.

Inventing Their Way Out of an Existential Threat

In 2020, Strategy found itself in a position many companies would envy: $500 million in cash reserves. But with interest rates cut to zero and the US government printing $5 trillion in stimulus, inflation was inevitable, and that cash was suddenly at risk.

“We’d spent 30 years building that reserve. It was about to be worth 20% less and earning nothing. That was existential.”

Phong and Strategy’s founder, Michael Saylor, made the call: to invest the company’s treasury into Bitcoin, treating it as the most promising store of value ever invented.

They invited shareholders to exit through a Dutch tender, offering a 15% premium to anyone who disagreed. The result? Only 10% took the offer. The rest stayed and have since seen a 70% return.

Building a Culture of Risk and Resilience

Phong spoke candidly about the mindset required to lead through uncertainty. Strategy sees itself less as a tech company, and more as a perpetual innovator, akin to Tesla or Apple in its willingness to disrupt.

He explained how Strategy weathered the 2022 “crypto winter” by building a resilient, anti-fragile system: long-t

erm debt, minimal covenants, and the confidence to hold steady through volatility.

“You don’t panic. You build for the long term and ride the cycles like any great business does.”

He also drew on personal experience, his parents were Vietnamese boat people who risked everything to start anew. That, he said, puts corporate risk in perspective.

Bitcoin as Digital Sovereignty

The conversation went deep into why Strategy believes Bitcoin is past the point of no return. With adoption across retail, institutional, and now even nation-state levels, Phong argued that Bitcoin has become a non-sovereign, scarce, and essential store of value.

“Money is the manifestation of your work. If you work for it, why wouldn’t you protect it?”

Beyond education, Strategy is now helping shape the market with preferred share offerings like STRK, giving investors a 10.5% yield backed by Bitcoin. Their recent STRC IPO raised $2.5 billion, the largest single-instrument IPO in the US this year.

Leadership Lessons That Landed

For Cycling Execs in the room, Phong’s message was clear:

Innovation is a mindset, not a department.
Courage builds conviction, especially when others doubt the decision.
Risk is not the enemy. Misunderstanding risk is.

More Than a Bitcoin Story

This was more than a tech or finance talk, it was a powerful reminder of what bold leadership looks like in practice. Phong brought warmth, intelligence, and humour to a topic that’s often polarising, leaving the room inspired, curious, and maybe just a little more courageous.

Big thanks to Phong, James, and our friends at Strategy for making the morning possible.

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