We spend our entire lives building—careers, families, and a home here on the SF Peninsula. But what happens to it all when we're gone? How do you ensure the life you've built becomes a lasting legacy instead of a legal mess for the people you love?

This week on South of SF, we demystify the world of estate planning. Ranger sits down with Winston Duggan, a senior associate attorney with the San Mateo law firm McDowell Cotter. Winston specializes in trusts, estate administration, and probate, guiding Bay Area families and business owners through the process of creating a clear, powerful plan for the future.

This episode is an essential guide for anyone who wants to gain peace of mind and ensure their loved ones are protected, no matter what happens.

Key Topics & Questions Answered:

• What is an estate plan and who really needs one in the Bay Area? (Hint: It's not just for the wealthy).
• How to avoid probate court in California, saving your family years of time, money, and stress.
• The critical differences between a Will and a Trust, and which one might be right for you.
• Incapacity Planning: What happens if you're alive but can't make your own financial or health decisions?
• What is the process for getting started with an estate planning attorney?

Episode Highlights & Timestamps:

(02:23) The Core Mission: Providing Peace of Mind: Winston explains how expert legal guidance through trusts and estate administration brings clarity during life's most difficult times.

(05:08) Why Estate Law? Winston shares his journey into this field and what keeps him passionate about helping people navigate complex legal systems.

(08:29) Community Involvement: Learn how McDowell Cotter gives back to the Bay Area community through service days with organizations like Second Harvest Food Bank.

(10:49) The 25-Year-Old Case: A real-world example of how unresolved estates can create a complex legal puzzle decades later, highlighting why avoiding probate is so critical.

(14:23) "Is Estate Planning Only for the Rich?" Winston debunks the single biggest myth in estate planning and explains the importance of incapacity planning for every adult.

(16:18) What to Expect When You Call: Winston outlines the simple, no-pressure process for an initial consultation to see if their firm is the right fit to help you.

(17:15) The Danger of a "Handshake Agreement": Why informal or "back of the napkin" plans can lead to disaster and the importance of a legally sound plan.

Connect with Our Guest:

• Guest: Winston Duggan, Senior Associate Attorney
• Firm: McDowell Cotter, Professional Law Corporation
• Location: San Mateo, CA (Serving the entire Bay Area)
• Book a Consultation: Call the office at (650) 572-7933 to get started.
• Website: mcdlawyers.net
• Support the Show:

If this conversation gave you the clarity you needed to take the next step, please leave a quick review on Apple Podcasts or Spotify. It’s the best way to help more people on the Peninsula find these essential local resources.

Until next time, keep it local, keep it real, keep it South of SF.