Estate Planning


Gene Farrell

May 17, 2023

The future of estate advisory: A new way to think about estate planning

  [Watch Legacy Now on demand, to learn more about Vanilla’s vision for estate advisory.] I believe that technology – when used thoughtfully – can be truly transformative. And this week at our Legacy Now event, with the help of Vanilla co-founder Steve Lockshin, I had the opportunity to share how Vanilla plans to transform not just estate planning, but financial advising as a whole, with the new Vanilla Estate Advisory Platform.  The technology itself is only a part of the picture. It’s a tool. It’s the enabler that, when paired with exceptional advisors, will allow for a new kind...



May 11, 2023

What is a power of attorney – and how does it work?

Life is unpredictable. And as a financial advisor, one of the essential parts of your job is to help prepare clients for that unpredictability – whether that comes in the form of balancing a portfolio so that it’s not over reliant on a single company or sector or ensuring they have the right documents in place in case of an accident or health scare. One of these key documents is a power of attorney.  A power of attorney (POA) is a legal document that authorizes an individual, known as the agent or attorney-in-fact, to act on behalf of another person,...



Apr 25, 2023

What is a living trust, a.k.a a revocable trust?

  A living trust (also called a revocable trust) is a legal document created by a person during their lifetime that directs how their assets are managed during their life, and how they are to be distributed after their death. It can also help bypass or minimize the sometimes expensive and time consuming probate process required by a traditional will.  A living trust is typically used in conjunction with a short will that directs all assets held in the individual’s name to “pour over” to the revocable trust on death (referred to as a “pour-over will”).  This living trust estate...



Apr 07, 2023

Communicating between the lines: Using Letters of Wishes to guide trustees

When it comes to estate planning, there’s no substitute for having the right core legal documents drafted, and ensuring they align with your clients’ wishes. But no matter how carefully estate planning documents are drafted, it’s impossible to anticipate every eventuality – and, the truth is, life often moves faster than clients do when it comes to updating their documents. One great way to bolster an estate plan against the unexpected, and to help trustees make decisions in accord with client expectations, is through Letters of Wishes. What is a Letter of Wishes? A letter of wishes is simply a...

Michael Blog

Daniel Brockley

Mar 15, 2023

The Advisor’s Advisor: Michael DiFiglio uses his experience at Ayco & Goldman Sachs...

Creating a truly remarkable product is rarely one person’s doing. It takes a team of smart, talented, dedicated folks to make it happen – a diversity of experience and perspectives. At Vanilla, we have a crack team of product designers and engineers who have brought our platform to life and continue to evolve it and make it better. But in addition to dialing in our tech, we need to always keep tethered to the realities of the finance industry – to the needs of advisors and attorneys – and their clients. That means that we all spend a lot of...

7 Sins Blog


Mar 08, 2023

The 7 Deadly Sins: Common estate planning mistakes to avoid

They won’t make your clients feel wicked. Still, the seven deadly sins of estate planning may leave your clients vulnerable to several unintended consequences such as probate, loss of assets in a divorce, and avoidable estate tax liability. Financial advisors can help their clients avoid the seven most common estate planning mistakes listed below. Estate planning mistake #1: Not updating estate planning documents regularly Some clients may think that creating an estate plan is a one-and-done proposition, but you should review and update your client’s estate plan with them when they experience any of the following: Major life events: Your...


Daniel Brockley

Mar 02, 2023

Process Matters: Why “bespoke” is not enough when it comes to estate planning

  Part I in a series of 3 on The Vanilla Estate Planning Playbook. Talk to any financial advisor out there, and you’ll hear a common refrain: Sure, we do estate planning. The thing is, what advisors mean when they say they do estate planning varies wildly. For many, doing estate planning simply means asking clients if they have basic documents in place, such as a Will, trust(s), healthcare directive and power of attorney. If the client has docs, the financial advisor moves on to other matters like investments. If they don’t, they refer the client to an estate attorney...

Pour Over Blog


Feb 28, 2023

What is a pour-over Will? The essentials financial advisors and their clients need...

Once a client has their Last Wills and Testament (“Wills”) and revocable trust created, their financial situation doesn’t just stand still. More often than not, a client’s financial situation will fluctuate throughout their life. A pour-over Will brings added security to an estate plan–making room for all of those potential life changes–by explaining what to do with new and unaccounted assets. This helps keep up with asset changes between times when your client updates wills and trusts. What is a pour-over Will? A pour-over Will is a Last Will and Testament that is used in conjunction with a revocable (a/k/a...



Feb 14, 2023

What is a spousal lifetime access trust (SLAT), and how does it work?

A Spousal Lifetime Access Trust (“SLAT”) is an irrevocable trust set up by an individual (the “donor”) during his or her lifetime for the benefit of the individual’s spouse and if, desired, other family members. How does the SLAT Work? A SLAT is created under a trust agreement, which contains the terms of the trust and the name of the individuals or entity that will act as trustee (typically a trusted friend or advisor). A SLAT is funded by way of a gift from the donor to the SLAT. During the donor’s lifetime, the trustee can make distributions to the...

what is probate Blog


Feb 09, 2023

What is probate, and how can you make it easier for clients?

When it comes to estate planning, “probate” is a term that looms large. You might hear talk of the complexity of probate, or strategies for avoiding probate — but what exactly is it? Put plainly, probate is the legal process that occurs after a person’s death. In probate, the court recognizes the validity of a Last Will and Testament (a “Will”) and appoints a personal representative for the decedent’s estate. The representative – also known as an executor or administrator – pays the decedent’s debts and then distributes the remaining assets to the beneficiaries. Though probate is simple to define...

Top 7 Gifting Blog

Daniel Brockley

Feb 02, 2023

Top 7 gifting strategies for estate planning

In 2021, Americans gave a whopping $484.85 billion to charities, a 4% increase from 2020. And that doesn’t account for gifts to family and friends outside of official charity organizations. Simply put, gifting is a huge part of our economy. Our guide provides a great refresher for advisors, and can also be given to clients to help educate them on their options when it comes to giving. Why consider giving? People choose to give for a variety of reasons, but there are two primary drivers that gifting has become such an important part of people’s lives (and their financial plans)....

ILIT trust Blog


Jan 26, 2023

What is an irrevocable life insurance trust (ILIT)?

Irrevocable Life Insurance Trusts (ILITs) are legal vehicles established specifically to own one or more life insurance policies and are set up during an insured’s lifetime. ILITs are created to own a life insurance policy and keep its proceeds out of the insured’s or owner’s estate to avoid increasing the size of their estate when the insured dies. When an individual owns an insurance policy (whether on his or her life or the life of another individual), the insurance policy is included in the individual’s estate at death and is therefore subject to federal estate tax (to the extent the estate exceeds...

Estate Planning Checklist Everything Your Clients’ Documents Should Cover for 2021, According to Our Legal Expert Blog


Jan 24, 2023

Estate Planning Checklist: Everything your clients’ documents should cover, according to our legal...

If something should happen to your clients, regardless of their age or income, it’s crucial that they have a plan for their financial assets. As their financial advisor, you’re in the best position to keep your clients on task so they can reach their goals and ensure their families are taken care of. But between a myriad of documents, individual state requirements, and shifting federal estate tax laws, it’s no wonder the estate planning process can be overwhelming for financial advisors and their clients. That’s why we’ve created this easy-to-follow estate planning checklist. We’ll give you clear insights into a...



Jan 17, 2023

What is a grantor retained annuity trust (GRAT)?

Grantor retained annuity trusts (GRATs) have increased in popularity in recent years because of how effective they are in transferring assets out of estates to beneficiaries in a tax-efficient manner. GRATs allow an individual grantor to transfer an asset’s upside out of their estate, with minimal risk or downside. Using this strategy, the GRAT transfers the initial value of the asset plus a government rate out of the grantor's estate. In brief, to establish a GRAT, a grantor transfers a particular asset(s) into an irrevocable trust and retains an annuity stream for a specified term of years. The annuity amount...

Charitable Remainder Trust Blog


Jan 10, 2023

What is a charitable remainder trust?

Many people have charitable intentions that they would like to consider as part of their estate planning. However, donating assets outright during their lifetime may not meet their financial goals. A more advanced strategy, such as a charitable remainder trust, may provide the flexibility to meet their personal financial needs while guaranteeing that a charity or charities end up with the remaining asset at the end of the term or when the settlor/donor is no longer living. When to use a Charitable Remainder Trust (CRT): When you are charitably inclined; and, You have highly appreciated securities you would like to...

What you need to know about generation-skipping gifts (and their tax implications) Blog
Jim Sinai

Jim Sinai

Dec 22, 2022

What you need to know about generation-skipping gifts (and their tax implications)

Gifting to your children is an excellent way to reduce estate tax liabilities, but sometimes it makes more sense to give directly to grandchildren, rather than to your children. Because these gifts “skip” a generation, they are referred to as generation-skipping transfers (GST) or gifts and have special tax treatment. There are a few important things to keep in mind when considering a generation-skipping transfer gift, including the generation-skipping transfer tax. We’ll break the tax down for you and give you a few more important pointers to pay attention to. What is the generation-skipping transfer tax? The generation-skipping transfer tax...

Let's take back our legacies Blog


Dec 06, 2022

Let’s take back our legacies

I am not an expert in estate planning. That may be a strange thing to admit for someone who runs a company focused on estate planning. What I do well (and what I find enormously rewarding) is identifying difficult problems, and – with the collaboration of great teams – use technology to solve them. When it comes to identifying which challenges to take on, I am drawn to areas where solving the problem can create real impact for individuals, families, and society. Estate planning is exactly this type of problem because it touches almost everyone. Helping individuals and families define...

What is a trust — and what are the different types of trusts Blog

Daniel Brockley

Nov 17, 2022

What is a trust — and what are the different types of trusts?

Trusts come up a lot in estate planning, and for good reason. They can be incredibly effective in helping fund education, provide for heirs, donate to charities and more. For high net worth individuals, trusts are also an important strategy to reduce taxable estates. The basics: What are trusts? Trusts are legal entities, much like corporations, which are considered distinct from the various parties involved. Trusts come in many forms, but in essence they are fiduciary arrangements in which, as the IRS states, one person (the trustee) holds title to property or assets…for the benefit of another (the beneficiary). Sometimes...


Daniel Brockley

Nov 03, 2022

Turning-Point Conversations: How to use important life events to refocus clients and deepen...

Curiosity – genuine curiosity – is one of the most important traits a financial advisor can have. Sure, this means curiosity about the different levers and pulleys of the economic machine, but it also means curiosity about clients. Not just about their risk tolerance, but about what makes them tick. Their goals, their fears. What gets them out of bed in the morning. A deeper understanding of clients as people, not just portfolios, enables you to bring the kind of value that goes far beyond index funds. There are certain times in life that lend themselves to these clarifying conversations–when...

What Should You Include in a Will? Blog

Daniel Brockley

Oct 20, 2022

What should you include in a Will?

  A Last Will and Testament (also known as a Will) is a legal document that outlines your instructions in the event of your death. It provides direction to your family, chosen representatives, and the court regarding how your assets should pass, as well as who should take care of your minor children (or pets!). Without a Will that expressly explains your wishes, the court will identify who gets your assets (generally your next of kin), based on applicable laws. And as for your kids? Well, without a Will, the court will make those decisions, too. In the United States,...

How Advisors Can Add Value Blog

Daniel Brockley

Oct 04, 2022

How financial advisors can add value in a bear market

It’s officially a bear market, now what? How advisors can add value when times are tough It’s brutal out there. After riding the sugar high of the pandemic, client portfolios – and probably your own portfolio as well – have found themselves in miserable hangover territory. The S&P recently hit a two year low and the Dow, not to be outdone, touched a yearly bottom as well. Instead of celebrating portfolio windfalls with your clients, you’re likely having some difficult conversations. But as challenging as these times are, there’s opportunity here. The current climate is the perfect chance to show...

Jim Sinai

Jim Sinai

Sep 19, 2022

10 Diagrams to explain advanced estate planning strategies

  Tax planning for clients with taxable estates has always been complex. We’ve learned the best way to explain estate planning strategies is with diagrams, not documents. That’s why we’ve put together this deck of 10 diagrams to explain some of the advanced strategies and why household with $10M in assets should care about estate tax. Why $10M in household assets? In 2026 the Estate Tax exemption drops down to just about $10M (or higher based on inflation). The 10 diagrams explain both why you need advanced strategies and how 8 different strategies work. We’ve explained them all below but...

How Millennials Think About Wealth Management Blog


May 25, 2022

Millennials and Estate Planning: What advisors should know

How millennials think about wealth management—including estate planning Millennials take their financial lives seriously—and they’re ready to enlist the experts to help. The past few years have seen a lot of change in the financial lives of millennials. The generation born between 1981 and 1996 is approaching their peak earning years and hitting major milestones from having kids to buying houses to starting businesses. According to one report, there are more than 618,000 millennial millionaires in the United States. And with the Great Wealth Transfer on the horizon, millennials are poised to inherit another $68 trillion from their Baby Boomer...

Here’s How Capital Gains Tax Changes Could Impact Your Clients’ Estate Planning for 2022 Blog


Sep 13, 2021

Here’s how capital gains tax changes could impact your clients’ estate planning for...

Estate planning is often treated as a “set-it-and-forget-it” topic, but it is vital—especially for wealthy clients—to stay on top of changes in law and in assets because failing to account for current tax law can put your heir’s inheritance at risk of significant reduction. Proposed capital gains tax changes will dramatically shift thresholds, making it more vital than ever for financial advisors to help their clients keep estate plans current and comprehensive. Historically, the step-up basis has been one of the strongest strategies for wealthy individuals to avoid paying capital gains taxes at death, but proposed changes to tax law...

The Top 4 Estate Planning Questions Advisors Have About UHNW Clients Blog


Aug 13, 2021

The top 4 estate planning questions advisors have about UHNW clients

Ultra-high net worth (UHNW) individuals’ estates are inherently complex and far-reaching, so having a comprehensive estate plan is vital to ensure a smooth transfer of wealth between generations and avoid expensive legal battles at death. But that doesn’t guarantee that these UHNW individuals are any more educated on estate planning processes and pitfalls. Even though 64% of wealthy individuals place a high value on the legacy they can pass on to the next generation, a full 39% do not have a comprehensive estate plan, according to the U.S. Trust Insights on Wealth and Worth. As their trusted financial advisor with...

Top 5 Challenges of Estate Planning for Blended Families (and How to Solve Them) Blog


Jul 19, 2021

Top 5 challenges of estate planning for blended families (and how to solve...

Deciding who gets what after one’s passing is tough. According to a survey by, only 42% of American adults have essential estate planning documents, such as a will or a living trust. People avoid planning for the inevitable for many reasons. But for blended families, a major reason is that estate planning requires more than a simple will. Many difficult questions come up: How do I ensure everyone is well taken care of after I am gone? Should I leave everything to my spouse and hope they take care of my children? How do I avoid disinheriting my children?...

How to Prepare for the Death of a Client Blog


Jul 08, 2021

How to prepare for the death of a client

You’ve built a solid financial foundation for your client, made investments with an eye on the future, and helped them strive toward making their financial goals a reality—but what happens once they pass on? Without preparation, the months following a client’s death can be a chaotic mess for a financial advisor. Assets need to be found, collected, and handed over to whoever is handling the estate. You put in hours of work, and in the end, you are left clientless, watching the assets you carefully tended for your client in life tangled in probate court and wasted on fees and...

4 Core Estate Documents Blog


May 24, 2021

The 4 Core Estate Documents: What they are and why they’re essential for...

According to a survey from, 2021 marks the first year that young adults ages 18-34 are more likely to have a will than those ages 35-54. COVID-19 seems largely responsible for this shift, but the pandemic hasn’t just impacted the younger generation. Participants of all ages agreed that the advent of COVID-19 has caused them “to see a greater need for estate planning.” As a financial advisor, this means you can expect more clients to turn to you for estate planning guidance in the coming days. With this influx of client needs, it’s important that you understand and can...

Naming the Right Fiduciary Trustee for an Estate Blog


Apr 22, 2021

The advisor’s guide to naming the right fiduciary trustee for an estate

One of the biggest estate planning mistakes people make is placing the power and responsibilities of a trustee in the wrong hands. Poor fiduciary selection can lead to family in-fighting, lengthy legal disputes, and a substantial loss of assets due to mismanagement. As a relationship-driven financial advisor, it’s essential that you understand the role of a fiduciary trustee and that you help your client select the right individuals or corporations to act as fiduciaries for their estate. A trustworthy, knowledgeable trustee helps safeguard the estate plan from mishandling and assures that beneficiaries get the full value of the assets. What...



Mar 26, 2021

Estate Planning Horror Stories: 5 nightmare scenarios that will scare you into action

  Most ghost stories are about unfinished business. Whether it’s a spooky campfire tale or a literary classic from the dark imagination of Edgar Allen Poe, a horror story plotline remains the same: the spirits of the departed haunt the living because there’s an unresolved matter preventing the deceased from moving on. So what does all of this have to do with estate planning? A poorly made or forgotten-about estate plan is like a ghost: It leaves your client and their loved ones vulnerable to hauntings of the financial kind. When people in mourning have to deal with their deceased...

Costly Risks That Come With Free Estate Planning Documents Blog


Feb 02, 2021

Top 6 costly risks that come with free estate planning documents

Tempted to give your clients free estate planning documents to create a will, trust, or other after-death protections? Think again. Free estate planning documents come with risks that may ultimately cost clients and their heirs more than they saved in legal fees. Let’s take a look at some of the significant — and expensive — problems that using free estate planning documents could cause. 1. Excluding family members from a will Free DIY wills don’t always tailor an estate plan to an individual’s circumstances and goals. This is particularly the case for blended families and new additions when it's easy...

New Estate Tax Complications: How to Prepare Clients for the Big Shift Blog


Jan 26, 2021

New Administration, New Estate Tax Complications: How to prepare clients for the big...

As the U.S. gains a new president and a new majority in the legislative branch, proposed changes to the federal estate and gift tax will transform the way wealth passes from one generation to the next. For wealthier families, this means the loss of allowances they’ve benefited from under a looser estate tax regime. As a financial advisor, the possible changes provide an excellent opportunity for you to deepen relationships with your clients. This quick guide will help you educate them on what to expect and offer guidance on how to navigate newer, more stringent estate tax regulations. Changes in...



Dec 11, 2020

7 Major reasons why estate planning isn’t a ‘set it and forget it’...

  Imagine that you're having your first consultation with a new client. You ask them whether they have an estate plan in place. They proudly tell you that they drew up a will and assigned guardianship as soon as their first child was born — 25 years ago. Job well done, next question — right? Not quite! Let's examine why treating an estate plan as a one-off task comes with significant risks that could end in nightmare scenarios for your client and their family. 1: Beneficiaries and fiduciaries are often temporary While your client may express a desire to designate...



Dec 02, 2020

“How do I get a medical power of attorney for my adult child?”...

  With more young adults living with their parents now since the Great Depression, families with college-age children need questions answered about where parents’ legal rights begin and end. As a financial advisor, you should be ready to answer the questions your clients have, such as “how do I get a medical power of attorney?” and connect them with the documents they and their adult children need to protect their families. This concise guide will help you point your clients in the right direction. “What are the legal realities of my child turning 18?” When a young adult turns 18,...

Check if Estate Planning Documents Are High Quality Blog


Sep 16, 2020

How do I know if estate planning documents are high quality?

As a financial advisor, you may be uncertain about the myriad of estate planning documents clients use, and which to recommend for the best possible financial outcomes for your client. Estate planning documents come in all shapes and sizes, but good planning documents need to address specific, important details. To help you sort through your clients’ paperwork, here’s how to discern if all those forms are well executed, high-quality estate planning documents. High-quality estate planning documents are updated regularly Thinking about the future and completing estate planning documents is an excellent first step, but your client’s financial situation is bound...

outdated estate planning practices Blog


Aug 24, 2020

How outdated estate planning practices can cost you and your clients

Estate planning is evolving. In a shifting landscape, financial advisors need to demonstrate value to their clients. One of the best ways to help your clients is to educate them about the risks of outdated estate planning documents, which, if left unchecked, can lead to serious consequences for them and their families. Of course, the estate planning process itself is somewhat outdated. Financial advisors often have no visibility into the conversations clients are having with third-party attorneys, creating an opaque, disconnected system with many moving parts. It’s difficult for financial advisors to offer the best advice when they can’t see...

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