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 their legacy and optimize the impact of their life’s work for the people and causes they care most about is the primary objective of estate planning.
Today estate planning is bespoke, artisanal, complex and can be extremely challenging for folks that don’t understand legal documents. I experienced this problem not long ago over the course of my own financial journey. Here’s what happened. And why I am determined to help change things.
My estate planning journey
For context, let me share a little about myself. 34 years ago, I married my college sweetheart and we have two boys who are now in their early 20’s and starting their own careers. My career began right after I got married and has progressed through four companies (Coca-Cola, Amazon, Smartsheet, and Vanilla) and five relocations between Seattle, the Bay Area, and Atlanta. About 10 years ago I lost both of my parents over the span of 24 months and experienced first hand the grief and strife that not having a good estate plan can inflict on a family.
Although we created a will when our first son was born, it wasn’t until I left Amazon to join Smartsheet as their Chief Strategy and Product Officer that my estate planning began to get complicated. Our family had grown over the years, and so had our net worth. This is where we got our first real glimpse of what a mess the status quo for estate planning is today.
We started by approaching our financial advisor, but as is so often the case, he didn’t have experience with estate planning, and referred us to an estate attorney. The attorney then proceeded to educate us at length on the nuances of estate planning and how we might protect our family and optimize for tax efficiency. While we appreciated this education, we had an unpleasant surprise when we realized how expensive it could be when paying by the hour. Eventually, we came up with a plan we felt okay about, but it wasn’t built in conjunction with our advisor, who knew the ins and outs of our long term goals. And, because our lives continued to change, it didn’t last long.
The reverberations of an IPO
When Smartsheet went public and we scaled the business from $100M to over $500M in revenue, it was a positive life change, but it also required a completely different level of estate planning – making the cracks in the system even more apparent. I still didn’t have a financial advisor who was comfortable with estate planning, so I went ahead and had an estate attorney prepare new documents, of course at great expense.
Soon after those documents were created, I had a chance conversation with an executive on a golf course in which he pointed me to a strategy that would be much better for my situation, allowing me to take advantage of the estate tax exemption while still living. When I asked my financial advisor about it, he concurred that it was a good strategy – and I had the attorney once again draw up new documents. Instead of the proactive advice I would have hoped to have gotten from my advisor or attorney, I ended up getting it on the links, by luck.
If this process can feel this broken for someone like me, who has the resources to invest in planning, how could it possibly work for others? When I talked with my friends about their experiences with estate planning, I learned that some of them shared similar experiences to mine and many didn’t even have estate plans because they didn’t know where to begin or had started the process with an estate attorney and quickly became disillusioned by the cost and complexity.
How to take our legacies back
Today, many individuals end up paying way too much for confusing estate plans that may not be the right fit for their life and family situation. This only gets worse when they discover how difficult and expensive it can be to maintain these plans in a way that stays up to date with their changing life.
While the very wealthy, who can afford the best estate planners, can derive exceptional value from a well crafted plan, the system today is not really serving the rest of us well. And the consequences for this broken system are huge. Only one third of people have even the most basic estate plan, and those who do have plans often have inadequate, outdated documents. It should not be this hard. Everyone deserves the opportunity to create a meaningful legacy and protect their family from unnecessary burden and grief regardless of how many assets they have.
It’s time to take our legacies back.
Taking charge of our legacy shouldn’t mean we need to become experts in estate planning. We want to empower regular folks and ultra high net worth individuals alike – as well as those who advise them – with tools that make the complexity of estate planning simpler and easier to understand. Tools that can evaluate their existing circumstances and recommend strategies they should consider, that might benefit them today or their spouses and kids and grandkids tomorrow. Tools that make estate planning an ongoing conversation. Not something that we shy away from, but something that we engage with – because actively creating our legacy today can be enormously fulfilling.
Making Estate Planning Simple for Advisors and their Clients
Our mission at Vanilla is to empower everyone to create a meaningful legacy. We see a world where everyone can maximize the impact of their life’s work by simplifying the estate planning process..
What does that mean in practical terms?
It means today we are building software and services that help wealth advisors drive the estate planning conversation with their clients. Wealth advisors are paid to help clients think about not only wealth creation, but also risk mitigation.
Vanilla will act as a single place where clients, advisors and attorneys can view all of their financial and estate information holistically. In a format that won’t be packed away in confusing documents or spreadsheets, but rather brought to life with powerful visuals, flowcharts, and living balance sheets. With Vanilla, both advisors and clients will be able to visualize different strategies to see how they will impact your estate before you actually implement them – seeing the numbers and flow charts change in real time. The experience will be better for clients and more helpful to beneficiaries, who can be brought into the conversation earlier, should clients desire it.
With Vanilla, financial advisors will be able to provide a differentiated level of service – and do it more efficiently. Clear, articulate estate planning conversations expand client relationships, uncovering deeper client goals and connect to the next generation. And the ability to include estate planning as part of the wealth advisory offering not only increases an advisor’s value, but saves clients on expensive attorney fees.
In this world we are building, legacy isn’t taboo – it’s embraced and celebrated. Everyday, Vanilla is fostering ongoing conversations between clients and their advisors so that clients’ estate plans represent their current wishes. Because life is always changing. We shouldn’t wait until it’s too late before we update our estate plans. And yet, with the way the system works now, it’s no wonder why people do. It’s time to change it.
