Wealth and Relationships: Skillful Love
Maintaining family harmony between family and business lies in learning together. Skillful love means intentionally prioritizing...
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Amy A. Castoro
- May 31
- 2 min
Wealth and Relationships: Five Tips to Keeping the Peace at the Family Vacation Home
- Meaningful Conversations Are Key by Amy Castoro Mom and Dad’s dream of the family vacation property providing a respite of family unity...
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Amy A. Castoro
- Dec 21, 2022
- 2 min
Wealth and Relationships: Sound Bites for the Holiday Table by Amy Castoro
From our team to your family team, we say thank you for the honor and privilege it is to be a part of your lives. We wish you all a...
54 views1 comment
Amy A. Castoro
- Nov 23, 2022
- 1 min
Wealth and Relationships: Serve Up Some "Emergent Listening"
Serve up some “Emergent Listening” this Thanksgiving and see your connection with your loved ones deepen. Emergent listening is not the...
117 views0 comments
Amy A. Castoro
- Aug 4, 2022
- 1 min
Tom Brady talks raising kids with great wealth with Jim Farley on Drive Podcast
Spotify podcast "Drive with Jim Farley" talks with Tom Brady about how being really wealthy is the hardest thing about raising kids. We...
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Amy A. Castoro
- Jun 14, 2022
- 1 min
Wealth and Relationships: Great Wealth ≠ Great Happiness
Recently, I attended a presentation by Neil Pasricha, a New York Times best-selling author on happiness. He said the idea that we work...
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Amy A. Castoro
- Dec 29, 2021
- 2 min
Wealth and Relationships: Starting Conversations in 2022
The Roman philosopher Seneca is credited with saying, “Luck is what happens when preparation meets opportunity.” In other words, luck...
168 views0 comments
Amy A. Castoro
- Dec 22, 2021
- 1 min
5 Hot Tips to Help You Through The Holiday Season
The holidays are here and so are those polarizing dinner table topics such as vaccines, politics, and parenting. Here are 5 hot tips to...
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Amy A. Castoro
- Nov 3, 2021
- 1 min
Wealth and Relationships: Roles and Responsibilities
The Cavanaugh family decided that any family member having a “significant” decision-making financial responsibility role within the...
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Amy A. Castoro
- Oct 13, 2021
- 1 min
Wealth and Relationships: 3 Essentials For a Smooth Wealth Transition
Our research shows transitions occur more smoothly when: 1. Heirs are better prepared 2. Relationships among family members are...
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Amy A. Castoro
- Sep 29, 2021
- 1 min
Wealth and Relationships: Whose Money Is This?
Hannah arrived at the long-awaited family meeting to talk about the family wealth feeling anxious. She knew they were wealthy, having...
85 views0 comments
Amy A. Castoro
- Sep 16, 2021
- 2 min
Wealth and Relationships: 3 Tips For Better Communication
A next-generation family member said to me “I find it hard to get together with my family to talk about anything meaningful. We end up...
44 views0 comments
Amy A. Castoro
- Aug 26, 2021
- 1 min
Wealth and Relationships: Level the Playing Field
Cameron’s mother died unexpectedly when Cameron was 25 years of age. This was the first time Cameron met his mother’s financial and legal...
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Amy A. Castoro
- Jul 28, 2021
- 1 min
Wealth and Relationships: The Trust That Binds
by Amy Castoro Wealth can complicate relationships and magnify levels of trust positively or negatively. A patriarch had a history of...
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Amy A. Castoro
- Jul 14, 2021
- 1 min
The Carter Center Speaking Event Preparing Your Heirs with Amy Castoro
Joel Kimmel and I were honored to participate in a webinar hosted by The Carter Center on "Preparing Your Heirs". Click this link to...
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Amy A. Castoro
- Jun 9, 2021
- 1 min
Wealth and Relationships: 4 Foundations of a Successful Wealth Transition
What is the difference between successful and unsuccessful transition planning? Successful transitions mean the family remains intact and...
56 views0 comments
Amy A. Castoro
- May 10, 2021
- 1 min
Wealth and Relationships: Is Your Family Ready For Wealth Transfer?
Take this quiz. If you score less than 4 “yes” answers, a successful transfer of wealth is unlikely. Contact us to discuss your results...
58 views0 comments
Amy A. Castoro
- Apr 28, 2021
- 1 min
Wealth and Relationships: When Do We Tell Our Family About The Wealth?
The question stems from the historical system of estate planning that says there is a certain age when kids are ready. The inevitable and...
41 views0 comments
Amy A. Castoro
- Apr 14, 2021
- 1 min
Wealth and Relationships: Start the Conversations Now
A successful business owner was becoming forgetful, but he wouldn’t admit it. He was making uncharacteristic decisions and becoming...
24 views0 comments
Amy A. Castoro
- Apr 8, 2021
- 1 min
Wealth and Relationships: Your Estate Plan Won't Protect Family Relationships
A patriarch wanted to leave his wealth to his three daughters; however, he wanted to be hands-off and did not care how they utilized the...
40 views0 comments
Amy A. Castoro
- Apr 2, 2021
- 1 min
Wealth and Relationships: How to Talk About the Family Money
Talking to the kids about the family money is often a conversation that gets “kicked down the road” until it is too late. Left...
33 views0 comments
Amy A. Castoro
- Mar 24, 2021
- 1 min
Wealth and Relationships: Little Questions Can Make a Big Difference
By Joel Kimmel, Senior Lead Family Consultant Through my work with The Williams Group for over 20 years, I found the biggest difference...
29 views0 comments
Amy A. Castoro
- Mar 11, 2021
- 1 min
Wealth and Relationships: The Dichotomy of Cordial Hypocrisy
Speaking honestly about draft picks for the NFL is one thing. Speaking honestly about inheritance is another thing entirely. Family...
366 views1 comment
Amy A. Castoro
- Feb 25, 2021
- 1 min
WSJ article "How to Know When to Quit Your Job"
Great article by Betsy Morris for The Wall Street Journal. In a family business, knowing when to step aside rather than down makes the...
71 views0 comments
Amy A. Castoro
- Feb 17, 2021
- 1 min
Wealth and Relationships: Alignment vs. Agreement
Alignment vs. agreement. Merging expectations inherent in generational wealth can be tricky if an agreement is the only option. Conflict...
36 views0 comments
Amy A. Castoro
- Feb 10, 2021
- 1 min
Family Meetings About Wealth and Wealth Transfer
Amy Castoro is quoted in this article from the Institute for Preparing Heirs on how important it is for advisors to refer families to...
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Amy A. Castoro
- Feb 3, 2021
- 1 min
Wealth & Relationships: Be Curious, Not Critical
The complex conversations needed to prepare heirs for wealth transition are often stalled because family members are afraid of being...
43 views0 comments
Amy A. Castoro
- Jan 28, 2021
- 1 min
Wealth and Relationships: Navigate Challenging Conversations
Inherent in transitioning wealth is the need to navigate challenging conversations. A mantra we use is "The right conversation at the...
25 views0 comments
Amy A. Castoro
- Jan 20, 2021
- 1 min
Wealth and Relationships: Expand Your Value Proposition
Evolution is about keeping your value proposition relevant. The number one concern among high-net-worth families is whether their wealth...
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Amy A. Castoro
- Jan 11, 2021
- 1 min
Wealth and Relationships
Relationships are tricky enough without adding the responsibility of great wealth to the mix. One of our coaches likes to say, “You can...
46 views0 comments
Amy A. Castoro
- Dec 23, 2020
- 2 min
Reflecting on 2020
The year 2020 has been the year of relationships. The sudden anxiety and uncertainty of the pandemic had us all pivot to the well-being...
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Amy A. Castoro
- Nov 25, 2020
- 2 min
Four Steps to Taking the High Road This Thanksgiving
Families come to us and want to know how to manage difficult conversations, and often those conversations show up around the holidays....
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Amy A. Castoro
- Nov 4, 2020
- 1 min
Stressed Out Feelings Also Magnify Family Discord
Check out The New York Times article by Paul Sullivan. In these uncertain times, stressed-out feelings also magnify family discord....
13 views0 comments
Amy A. Castoro
- Nov 4, 2020
- 1 min
Things Will Not Go Back to the Way They Were
Good article from The Wall Street Journal by Chip Cutter - A common theme I read among the CEOs is that we must accept things will not go...
22 views0 comments
Amy A. Castoro
- Oct 15, 2020
- 1 min
Does Your Family Have Strong Trust and Communication For a Successful Wealth Transfer?
One of Buffet's truths that separate the doers from the dreamers is investing in communication skills. "One easy way to become worth 50...
32 views0 comments
Amy A. Castoro
- Jul 13, 2020
- 1 min
Stop Complaining About Your Colleagues Behind Their Backs
Great article in Harvard Business Review by Deborah Riegel. We see the gossip dynamic in many families as well as family businesses. At...
44 views1 comment
Amy A. Castoro
- Jun 26, 2020
- 1 min
Survey Results — New Programs for Advisors and Wealth Managers
We recently surveyed our community of contacts to learn more about their emerging needs during these turbulent times. The resounding...
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Amy A. Castoro
- May 5, 2020
- 1 min
A Message From Our Coaches
COVID-19 has made the world a scary place and we are here for you every step of the way. Your future and the future of your families are...
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Amy A. Castoro
- Apr 20, 2020
- 4 min
Healthy Habits for Virtual Family Meetings
The Coronavirus has brought the wellbeing of family relationships, and the fragility of our health to the forefront. Many people are...
62 views0 comments
Amy A. Castoro
- Apr 15, 2020
- 3 min
Three Online Educational Resources for Families
Recommended by our coach, Marion MacGillivray We are living in an extraordinarily challenging time. Many families are struggling to work...
63 views0 comments
Amy A. Castoro
- Mar 24, 2020
- 1 min
Tips for Having Meaningful Conversations at Home
During this uncertain time, it's important to have conversations about your family's future. We are all at home in close quarters with...
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Amy A. Castoro
- Mar 16, 2020
- 1 min
Centering Exercise - Stress Relief
As we are all social distancing during this trying time, it's good to take a moment and center ourselves to reduce stress. Join our...
35 views0 comments
Amy A. Castoro
- Dec 20, 2019
- 4 min
How to Talk to the Kids About Wealth This Holiday Season
Waiting for the right time to talk to your kids about their expectations regarding the family wealth? The holidays can be a natural time...
45 views0 comments
Amy A. Castoro
- Jul 23, 2019
- 5 min
Take Your Family Council to the Next Level of Performance
We recently worked with a family council that was stalled on policy design and growing increasingly frustrated with their lack of...
15 views1 comment
Amy A. Castoro
- Jun 3, 2019
- 1 min
NextGen Collaborative - What's Next for NextGen?
What's Next for NextGen? Check out Amy's video on NextGen and find out more information on our NextGen Collaborative program kicking off...
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Amy A. Castoro
- May 2, 2019
- 1 min
Is Everyone Being Heard?
A philanthropic strategy is a great idea, but not if everyone isn't being heard. Check out Amy's family insights in her new video.
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Amy A. Castoro
- Mar 24, 2019
- 1 min
Communication is Key
New video by our very own Amy Castoro on how communication is key in families with great wealth.
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Amy A. Castoro
- Mar 14, 2019
- 3 min
Managing Both a Portfolio and Family Dynamics: Two Skill Sets
I was on a call with an advisor yesterday who said the advisors in his practice “do what we do.” If that were true, we would have far...
21 views0 comments
Amy A. Castoro
- Feb 25, 2019
- 5 min
Honesty in Families Can Be Complicated
Turning 30, Paul felt it was time to leave his family’s third-generation real estate business, even though it was experiencing a meteoric...
21 views0 comments
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