Dailey Resources

What Legacy Are You Really Leaving Behind?

January 29, 20251 min read

As an entrepreneur, you’re likely focused on building something that lasts—something you can pass on to the next generation. But legacy isn’t just about wealth. It’s about the values, character, and connections you leave behind.

I recently heard an estate planner pose a set of thought-provoking questions—not the usual financial planning questions, but the ones that should be asked. These shifted my perspective, and I wonder which of them resonate with you:

  1. If you could transfer all of your financial wealth without any tax or you could have grateful children, what would you pick?

  2. If you could average a 12% return on your investments, or you had children who were self-reliant, self-sufficient, productive, and mature, what would you pick?

  3. If you could completely asset protect all of your assets or you had children who knew who they were and what they valued, what would you pick?

  4. If you could ensure that your assets were used exactly as you outlined or that your family was engaged, involved, and connected with each other 50 years from now, what would you pick?

These questions get to the heart of what legacy really means. Money is a tool, but character and connection are what truly last.

So, as you think about the impact you want to leave, which of these questions challenges you the most? I’d love to hear your thoughts.

What Legacy Are You Really Leaving Behind?

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.

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