Interview with Dan Stickel, the CEO of EstateExec [2023]

Thanks for having me!  I’ve been a long-time tech entrepreneur, doing everything from starting companies in my spare bedroom, to serving in executive roles at tech giants such as Google.  I’ve been the CEO of multiple tech companies, responsible for $ billions in product revenue, and raising >$100M in investor capital. I have an undergraduate degree from Harvard University in Applied Mathematics, and a graduate degree from Harvard University in Computer Science.

I founded EstateExec in order to improve the experience of estate settlement.  For those of your readers who don’t know, when anyone dies, their estate must be “settled”, meaning their assets collected, their debts paid off, government forms filled out, and inheritances distributed (well, that’s the simple version).  Usually, this is handled by a family member who has never done it before and could use some help.

EstateExec provides step-by-step instructions that are automatically customized for the particulars of the estate, and integrated estate accounting (including the ability to download and analyze related bank transactions).  It simplifies the process, and reduces the chances for making errors.

EstateExec provides step-by-step instructions that are automatically customized for the particulars of the estate, and integrated estate accounting (including the ability to download and analyze related bank transactions).  It simplifies the process, and reduces the chances for making errors.

A few years ago my father passed away, and I was named executor for his estate.  Given my degrees from Harvard and my experiences running large organizations, I thought it would be relatively easy to go through the process of settling his estate, but I was surprised at how challenging it was, and how antiquated the entire process seemed.

I realized I could make a difference here, and that since everyone eventually passes away, that such a project would touch the lives of millions, actually hundreds of millions of people.

To clarify, we position EstateExec as a productivity aid for estate executors.  Although we help guide our users through a maze of legal processes and inform them of publicly available statute information, we do not provide legal or financial advice.  

That being said, privacy is VERY important for our users, and so our policy is that their data is private.  We do not sell, rent, or expose their information in any way to third parties, and we do not accept advertising on the site.  And of course we use state-of-the-art security technology, encrypting their information both in transit and while stored.

EstateExec is part of the modern world, in which you can do everything online.  EstateExec includes online sharing, so you can share View or Edit access with other people as desired, such as a co-executor, a lawyer, an accountant, or even an heir.

The core of EstateExec is the software, which provides automated guidance and integrated accounting.  The guidance typically includes reference to the relevant statutes for the particular jurisdiction, so that if users have questions they can read the source law themselves.

EstateExec also includes links to services that can help users with particular tasks, such as estate sales, asset appraisals, or even legal advice.  We generally list only service providers that are accredited in their industry (such as the Appraisers Association of America, or the American Bar Association), and provide that membership information to our users.

I love my work, so I’m happy to spend quite a bit of my time focused there.  At the same time, I’m quite disciplined, so I know I have to carve out time for things such as exercise, sleep, and so forth.  I probably fall a little short in keeping up with some of my personal relationships, but I’m always resolving to do better.  And I love to go on adventure trips, so that gets me out of the work routine as well.

We are always improving and enhancing the software. Most recently, we added support for spousal deemed disposition deferments in Canada… I know that sounds detailed and boring, but it’s actually quite important and has significant real-world implications for taxes due. It’s actually a big deal, even though it may not sound like it.

We have MANY new features under development as well, some much more accessible and exciting to discuss, but we’re going to keep those under wraps until we go into beta with them.

I think it’s important to encourage vigorous debate so that we can be sure we’ve considered options and alternatives, but it’s important that people understand we’re talking about ideas, not the people with the ideas.  I find it’s helpful to have everyone sit on the same side of the table, and commonly view the whiteboard or the slides with the ideas on the other side.  Of course, you can’t debate every little thing, and people need to be empowered to make decisions within their own areas.

I meet people all the time who want to address this space, because they have personally had an experience with estate settlement and realize it could be improved.  But one of the reasons for that is that it’s a tough space: rules and processes vary from jurisdiction to jurisdiction, and separately, it’s hard to change behavior for a market that has been established for literally hundreds of years.  So my main advice would be a word of caution that it’s not as easy as it might appear.

But if they do create a useful service, we’re happy to link to it in order to provide the best experience for our users…

EstateExec will continue to be the leading software aid for estate executors, and add even more important capabilities.  In fact, estate settlement is such a broad category that our roadmap could easily extend 10-20 years out!

At the same time, we will likely continue to expand our geographic coverage, at least for now sticking to countries whose primary language is English.