Why Every Entrepreneur Should Plan for Failure?

Inside this conversation

Patrick Wood is a 30-year entrepreneur in finance and capital markets across Canada and the U.S., now leading an early-stage public company redefining how digital asset treasuries hedge risk. We spoke about what it really takes to endure the entrepreneurial grind — and why expecting failure can become your most powerful advantage.

“Always plan on failure first,” Patrick says. “Expect it’s going to fail — then move, pivot, and adjust.” That mindset has guided his own journey, from stockbroker to CEO, through multiple pivots that turned potential collapses into breakthroughs. When his firm’s initial product for credit markets stalled, he leveraged the same structure to serve crypto treasuries — a small shift that unlocked major traction. “We accepted the fact it was looking like a failure and needed to act,” he reflects.

Patrick explains that few founders win on their first try, or even their fourth. What matters is readiness — anticipating how to adapt when things break. “If it was easy to do what we do, everyone would be doing it,” he says. For him, entrepreneurship remains a strange but irresistible pursuit of freedom, responsibility, and self-governance.

Listeners will come away with a pragmatic view of resilience — how to build flexibility, protect investors, and make smarter strategic pivots when the wind shifts.

Key takeaways

• Expect failure as part of the entrepreneurial process, not an exception.
• Build your plan two steps ahead — always know your pivot options.
• Leverage what already works instead of starting from scratch.
• Accept when something’s failing early to minimize damage.
• Freedom and self-direction outweigh comfort for true entrepreneurs.
• Collaboration with the right advisors accelerates smarter decisions.

Episode description from the official 21CE podcast feed. This text is the show notes, not a full transcript.