Dailey Resources

Leading Through the Unknown, Lessons from Walt (and James Shaw)

May 07, 20251 min read

Some people host events. James Shaw invites transformation.

Alyce and I got to be part of his Elevate event this week, she spoke, and we both sat in on a keynote that hit home. James shared lessons from Walt Disney’s life that feel surprisingly relevant for those of us leading businesses, raising families, and building something that lasts.

The core idea? Greatness doesn’t come from having a perfect plan. It comes from taking risks, adapting when things fall apart, and staying rooted in story.

Walt lost the rights to Oswald and came back with Mickey. He launched Disneyland before it was finished, before he had everything figured out. He made bold moves that didn’t make sense at the time, but became turning points later.

James laid out five lessons that stuck with me:

  1. Start before you’re ready. Waiting for certainty usually means waiting too long.

  2. Dream bigger. Ignore the doubters. If it feels a little scary, you’re probably on to something.

  3. Keep improving. Ask, Where can we make this 1% better? Then do it.

  4. Lead with story. People don’t remember stats. They remember how you made them feel.

  5. Don’t waste your setbacks. That hard season might be the soil your next season needs.

This isn’t about trying to be Disney. It’s about remembering that all great things start unfinished. Imperfect. A little messy.

So this week, ask yourself: Where am I waiting when I could be building?

Learn More About James Community

Elevate 2025

Seth is the Co-Founder of both The Dailey Group and Keller Williams Gateway in Baltimore, Maryland. He serves as the Operating Principal for the brokerage and as the team leader for The Dailey Group, which consistently helps over 150 families a year. Seth, a Montana native, is passionate about empowering leaders and teaching people to make smart financial moves.

Prior to real estate, Seth held his CPA designation and worked as a mortgage lender before joining forces with his wife of 20 years, Alyce. Seth can usually be found at the nearest coffee shop with a personal growth book in hand while scribbling down his next great idea on the back of a napkin.

Seth Dailey

Seth is the Co-Founder of both The Dailey Group and Keller Williams Gateway in Baltimore, Maryland. He serves as the Operating Principal for the brokerage and as the team leader for The Dailey Group, which consistently helps over 150 families a year. Seth, a Montana native, is passionate about empowering leaders and teaching people to make smart financial moves. Prior to real estate, Seth held his CPA designation and worked as a mortgage lender before joining forces with his wife of 20 years, Alyce. Seth can usually be found at the nearest coffee shop with a personal growth book in hand while scribbling down his next great idea on the back of a napkin.

LinkedIn logo icon
Instagram logo icon
Back to Blog