Going Big by Challenging the Status Quo: Kip Woodward on Leadership, Innovation, and the Courage to Ask “Why?”

Some people build businesses. Others build institutions. Kip Woodward has spent a lifetime doing both.

A fourth-generation business leader, investor, healthcare executive, and public policy advocate, Woodward has led organizations across retail, agriculture, healthcare, hospitality, and finance. Throughout his career, one trait has remained constant: an unwillingness to accept "that's just the way things are."

On this episode of Going Big!, host Kevin Gentry explores how curiosity, thoughtful leadership, and a willingness to challenge conventional thinking have shaped Woodward's remarkable journey.

Curiosity Creates Opportunity

Woodward traces much of his success to a habit he developed early in life: asking questions.

After his family's department store business was sold, he helped lead Douglas Lake Ranch, constantly looking for ways to build on what already existed. Whether expanding operations or creating entirely new revenue streams, he learned that innovation often comes from seeing possibilities others overlook.

That same mindset would eventually shape his work in healthcare and public policy.

Turning Frustration into Action

One pivotal moment came when Woodward tried to bring mobile MRI units to underserved communities in British Columbia. Although the idea had proven successful elsewhere, Canadian regulations prevented it from moving forward.

Rather than walking away, he began asking a bigger question: Why were patients waiting so long for care when other countries had found better solutions?

That experience led him into healthcare leadership and years of work advocating for reforms that improve patient access while preserving universal healthcare.

Leadership Is About People

Whether overseeing billion-dollar healthcare organizations or growing private businesses, Woodward believes leadership starts with simplifying complex problems and building strong teams.

He also speaks candidly about failure. Every major opportunity, he says, involves risk, setbacks, and difficult decisions. Success comes from surrounding yourself with trustworthy people, learning from mistakes, and staying focused when challenges arise.

One lesson has guided him throughout his career: if you want to create change, you have to be "in the tent." Complaining from the outside rarely solves problems. Real impact comes from engaging with people, building relationships, and helping shape better solutions.

Walk Through Open Doors

When asked what advice he would give young people, Woodward encourages them to remain curious and say yes to unexpected opportunities.

Join a nonprofit board. Take the meeting. Meet people outside your profession. Those experiences often become the moments that shape an entire career.

Looking back, Woodward believes Going Big isn't about chasing titles or recognition. It's about having the confidence to ask better questions, the humility to keep learning, and the courage to step through doors that others might never open.

Listen to the full episode of Going Big! with Kip Woodward to hear how curiosity, thoughtful leadership, and a willingness to challenge the status quo can create lasting impact.