Patrick Wood: Why Every Entrepreneur Should Plan for Failure

The Paradox of Expecting Failure

Most entrepreneurs begin their journey fueled by optimism. Yet Patrick Wood, a 30-year veteran of capital markets and the CEO of DelphX Capital Markets, believes success begins with the opposite mindset: expecting things to go wrong.

“Entrepreneurs should always plan for failure,” Wood says. “That mindset keeps you two steps ahead instead of one.”

His message lands differently in a world obsessed with “fail fast” mantras. For Wood, failure isn’t a slogan—it’s a strategy. Whether you’re a first-time founder in Nairobi, a second-career entrepreneur in Toronto, or a solopreneur building an online brand, the same truth applies: resilience is built on readiness.

Why Planning for Failure Is a Winning Strategy

Failure is not a possibility—it’s a certainty somewhere along the road. Markets shift. Investors hesitate. Customers surprise you. The entrepreneur’s job is to anticipate each of those fractures.

Wood’s philosophy came from three decades of experience navigating volatile financial systems. “If it were easy to do what we do, everyone would be doing it,” he reminds us. “You have to expect that what you’re doing might fail—and move and pivot accordingly.”

This proactive mindset reframes entrepreneurship from a heroic leap to a strategic series of recoveries. The winners aren’t those who never fall; they’re those who get up quickly, recalibrate, and move again.

Case Study: Pivoting DelphX from Credit to Crypto

Wood’s own company is proof. DelphX began by offering downside-protection tools in traditional credit markets. When traction slowed, the team asked the uncomfortable question: What if this doesn’t work?

Rather than collapse under sunk costs, they looked sideways—to the exploding crypto-treasury market. “We leveraged the infrastructure we’d already built,” Wood says, “and applied it to a market where the wind was at hand.”

The pivot produced a breakthrough product: a fully collateralized hedge for digital-asset treasuries, eliminating counterparty risk by backing Bitcoin exposure with U.S. Treasuries. In essence, DelphX gave conservative CFOs a reason to trust crypto.

That small shift transformed near-failure into competitive advantage.

Collaboration as a Survival Skill

No pivot happens in isolation. Wood credits collaboration as the often-overlooked safety net for entrepreneurs.

“We wouldn’t have a company without key advisors,” he notes. “Strategy, product development, even emotional support—they make the difference.”

For entrepreneurs working solo or in small teams, collaboration might mean forming peer circles, joining accelerators, or even sharing early prototypes with trusted critics. Diverse perspectives act as radar for blind spots that ego alone can’t detect.

How to Build a “Plan B Mindset”

Wood’s approach can be distilled into four repeatable principles:

1. Assume volatility, not stability. Markets and moods change faster than you can plan. Model scenarios for the worst 20 percent of outcomes, not just the best.

2. Design flexible systems. Build products and workflows that can be repurposed—like DelphX’s technology that transitioned from credit to crypto.

3. Track weak signals. Listen to advisors, data, and customers whose feedback contradicts your assumptions.

4. Detach identity from outcome. A failed launch doesn’t mean a failed founder. As Wood puts it, “Don’t go into a severe depression—keep doing what you’re doing, but be prepared to adjust.”

   
   

Reflect on this in your own business: if your core product vanished tomorrow, which capability could you repurpose within 30 days?

The Hidden Cost of Perseverance

Wood is candid about the toll. “It takes decades in some cases to get it right,” he says. “Those decades mean you get older, and when you finally hit that high point, it can feel anticlimactic.”

Entrepreneurship, he adds, can be “sinister”—a self-inflicted challenge chosen over an easier life of employment. Yet behind that hardship lies the deeper reward: freedom and self-governance. “Being in control—or at least thinking that you’re in control—of your destiny,” he says, “is what makes it worth it.”

For readers balancing family expectations, financial uncertainty, or cultural barriers, this perspective reframes entrepreneurship as a practice of agency, not just ambition.

What’s Next for DelphX—and for Founders Like You

Looking ahead, Wood envisions DelphX becoming a prime acquisition target within the next three years, after which he plans to launch a private-equity group specializing in early-stage financing. It’s a classic entrepreneurial loop: build, exit, reinvest, and start again—this time wiser.

For aspiring founders, the message is timeless:Failure is feedback. Adaptation is profit.

Key Takeaways

• Expect failure early. It reduces emotional volatility and sharpens strategy.

• Pivot intelligently. Reuse assets, don’t restart from zero.

• Collaborate constantly. Mentors and partners expand perspective.

• Protect downside risk. Whether in finance or mindset, safety nets fuel bold moves.

• Redefine success. The goal isn’t perfection—it’s sustainable evolution.

Call to Action

Ask yourself: What would my next move be if today’s plan stopped working?

Sketch it out. Share it with your team. Rehearse your pivot before reality forces it.

Explore more insights from Patrick Wood, download the episode, take notes, and start designing your own antifragile business strategy.