Have you ever heard of the adage “shirtsleeve to shirtsleeves in three generations?” It refers to the inability of children and grandchildren to manage family wealth that has been passed down. And it starts with the classic American dream story. One of the first generations hits it out of the park with success, but by the third generation, two things have happened: One, the money is all gone, and two, family relationships have been laid to waste because of the impact of the money on the family.

In fact, there have been studies done on affluent families to understand the reasoning better, and it’s not because of the lack of planning – less than 5% of failures are due to any failure to plan, so the pros are doing it right – fist pump in the air! Instead, they found that 60% of these failures are due to a lack of communication and trust within the family. Unprepared heirs cause another 25% – no one is setting them up for the roles and responsibilities they will have once mom and dad are gone. In addition, many people will raise their children to believe they are poor or middle class – not letting them know there is any family wealth. We highly recommend against this!

Finally, the last 10% of failures are caused by having no vision or mission of what to do with the money. We’ve been working on family legacy planning for years at DMG. We put together the “Living in Possibility Process” to help families address these issues, and Richard even wrote a book called Endless Inheritance that also walks a family through how to address these various causes of failure. To order a copy of his book, follow this link, and to learn more about family legacy planning, please visit https://aplaceofpossibility.com/family-and-legacy/.


Wondering what a family legacy video is like? Here’s Richard Del Monte’s legacy video for his uncle Bill Del Monte, the last known survivor of the 1906 San Francisco Earthquake and Fire. Bill’s father founded the Fior d’Italia restaurant in San Francisco, which fed the hungry, homeless masses after the quake and resulting fire.

One solution to the failures we discussed is creating a family legacy video. If you think about it, there’s the traditional way of passing things on through simple conversations, but they can quickly become forgotten and disappear over time. Photos are good for capturing a single moment; books and letters can give us valuable information, and audio can preserve one’s voice. But nothing compares to a video.

It instantly takes you back to moments in time that can be shared and passed down and ultimately helps foster connections for generations to come. That’s why we’re excited to sit down with a true expert on the topic, Stephanie Shaterain. Stephanie owns fLO Content, a video production firm specializing in documentary-style pieces that serve specific goals or strategies, and one of their specialties is legacy videos.

In this episode of A Place of Possibility, we’ll be discussing:

  • The shirtsleeves-to-shirtsleeves phenomenon of family wealth dissipating through the generations and how to prevent this from happening.
  • Inspiring family stories that were preserved through video, including one from the Del Monte family!
  • An inside look into fLO Content, how they got started, how it works, and what to expect when working with them.
  • Special tips on how you can help preserve your family’s wealth, traditions, and values.

And much more!

To all the parents and grandparents who want to secure the future of the upcoming generations, this podcast is for you. It’s never too early to start thinking about the future. Join us as we dive into the secrets to maintaining wealth and family legacy through the generations.

P.S. Looking to meet with Richard or Angela at our office in Alamo, CA? Want to discuss more of what you heard in this episode? Wondering where the heck you need to get started or what all of this means for your retirement plans? Schedule a free 30-minute session and find the peace of mind you deserve for the rest of your life. You can also reach us by calling 925.736.6410 or sending an email to Info@APlaceOfPossibility.com.

“What better way to communicate with your family than through a video? It connects them to their history. It shows them how some of the wealth was made, in many cases. And when you have this conversation in the context of more than just getting an inheritance, and instead that you are a steward of something really amazing, they approach the money and the relationships with their siblings/business partners differently.”

We’re proud to present you with our “Know Your Possibilities Guide,” a tool and free resource for you to take notes, review, keep on hand, or even share with your friends and family. So grab your copy, click the play button and follow along. You’re just minutes away from discovering your next Place of Possibility.

A Glance at this Episode:

0:00 Introduction

2:02 60% of the time, generational wealth dissipates due to a lack of trust and communication in the family. So, in this episode, we’re discussing how video production can support your family legacy for generations to come.

6:54 In a video clip, Richard’s uncle, Bill Del Monte, describes his experience as the last known survivor of the 1906 San Francisco earthquake and fire. Find out what an incredible impact this had on Richard and his family by tuning in here.

11:11 We’re diving in with our guest, Stephanie Shaterian, to discuss the use of legacy videos and their importance.

12:10 Stephanie shares more about how she got started in the production business, which began with her family.

14:13 Next, Stephanie discusses the benefits of the exploratory process in legacy video production for each family.

15:14: When developing these types of videos, there are usually three ways they can be developed: a family documentary, a values-based project, or a private/public project that benefits the family and the family business or organization.

18:13 Most people think that a video would focus on the history, but the real golden nuggets are in the values – what values got you through the struggles of achieving your goals?

19:02 One goal of fLO Content is making you and your family comfortable unearthing the values you want to share and outlining the storytelling elements.

20:48 A vital part of the video process is communication, staying on the same page with the family from beginning to end, and frontloading the project with a big-picture outcome, so it's smooth sailing when the editing process comes.

21:26 There’s something inherently unique about a video versus other forms of media. How does Stephanie help clients move forward with video production?

23:12 In this portion of the show, we discuss fLO Content’s process for creating a family video and what clients can expect.

27:17 If you’re someone who doesn’t like to be the center of attention or show your face, Stephanie has a special message just for you.

29:43 Your legacy video could cost the same as a family vacation. The only difference is this project lasts a lifetime.


Get in touch with Stephanie!
Stephanie Shaterian
Owner, fLO Content


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Links/Resources Mentioned in this Episode:


“One-size-fits-all” won’t fit you here! The Del Monte Group team understands that everyone’s financial goals are unique. That’s why we always provide customized advice. No matter where you are in life, you can depend on our proven expertise to provide financial planning support for long-term success. Ready to get started? Schedule a meeting with Richard or Angela in our Alamo, CA based office today or we can meet via Zoom! >> You can select a date and time that works for you via our calendar, call us at 925.736.6410, or send an email to Info@APlaceOfPossibility.com. We can’t wait to help you!

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