Community//

Dan Stickel of EstateExec: “Dealing with the aftermath of death is inevitable, and it’s hard work”

Dealing with the aftermath of death is inevitable, and it’s hard work. It’s not something we do every day, but we all face the death of our parents at some point. It can be traumatic, it can be overwhelming, and it’s commonly a lot of work. We commissioned a study of the general population and […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

Dealing with the aftermath of death is inevitable, and it’s hard work. It’s not something we do every day, but we all face the death of our parents at some point. It can be traumatic, it can be overwhelming, and it’s commonly a lot of work. We commissioned a study of the general population and found that on average it takes 570 hours of effort to settle an estate, over a period of 16 months … sometimes much more. The task can become all-consuming, and it’s sad to see one person’s death lead to the destruction or degradation of another person’s time and well-being.

EstateExec can’t do all the work for someone, but it can help them in their time of need, potentially saving hundreds of hours, thousands of dollars, and perhaps most importantly, saving fragile relationships among the survivors (it turns out that estate inheritance issues are a key cause of family strife and even lawsuits).


As a part of our series about cutting edge technological breakthroughs, I had the pleasure of interviewingDan Stickel.

Dan Stickel is founder and CEO of EstateExec. Stickel is a former Google Executive and serial entrepreneur, with both an undergraduate and a graduate degree from Harvard University. He has managed multi- dollars B product lines, raised over 100 million dollars in funding and served as CEO for several global software companies.

Motivated by his experience serving as the executor for his parents’ estates, he founded EstateExec to bring the process forward from the 18th century to the 21st, creating the world’s first software to assist consumers throughout the challenging and complex process of serving as an estate executor, automatically creating customized task lists, helping to organize the estate, and automating financial calculations. EstateExec helps consumers on their own, and through its sharing feature, also allows them to coordinate with lawyers and other interested parties if desired.

Before Google, Stickel ran the Software Division of the public company Macrovision (MVSN) growing worldwide revenues from 25 million dollars to over 100 million dollars, representing half of the overall company’s revenues. He has also started several companies, and won the Ziff Davis Desktop Accessory of the Year award for software he personally wrote. Stickel has served as a keynote speaker at numerous conferences around the world, and has used software to improve people’s lives in a variety of fields, from early broadband efforts to web search (including both Google and AltaVista), from scientific modeling to simple accounting calculators, and from high-end security immune systems to military AI systems.

Dan was valedictorian of his high school class, and went on to graduate from Harvard University in three years in the top 5 percent of his class, while working half-time in the cardiovascular unit at the New England Medical Center. He earned a Master’s degree from Harvard as well.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I took my first official course in computer science as an undergraduate at Harvard University and fell in love with software. I went on to get a Master’s in computer science and pretty quickly headed to Silicon Valley to join a startup in AI. Over the years, I worked at a number of companies, ranging from ones I started in a spare bedroom to working at massive companies like Google. The companies covered a wide range of domains — from web search to defense intelligence to personal productivity to natural disaster modeling and beyond. The one thing they had in common was elegant, powerful software addressing a real need.

When my parents separately passed away, I had the privilege and the burden of serving as an executor for both estates. I was surprised at how much effort the role required and that there were almost no resources to help — a couple of encyclopedia-like books, and some blog posts. As a successful CEO experienced in managing multi-billion-dollar products, I thought it would be easy for me, but it was actually a little overwhelming. I read up on things, pulled together some custom Google Sheets, and muddled through.

3 million people die in the US and Canada every year, and by law, their estates must be settled by an executor, usually a family member who has never done it before and who has no idea what to do. Given my background, I realized that there was an underserved market here — one mandated by law, and which fundamentally hadn’t changed since the 1800’s. Everyone was busy inventing the next group chat or social dating site, things that younger people tend to care about, but here was an inevitable need that no one was doing anything about, so I founded EstateExec!

Can you share the most interesting story that happened to you since you began your career?

I have a few stories that might compete for that title, but when I was working in the defense industry, a partner and I were at the airport transporting some classified material in a country we had been briefed was not safe for us, and where we would likely be subject to counter-intelligence efforts. Suddenly, several military police came up to us, and without explanation insisted my partner come with them. It was a little stressful, and I was faced with a dilemma: Do I raise my hand and tell them that we can’t be separated because we are carrying classified material, or do I try to protect the material and continue solo, changing the mission parameters? Obviously, the smart thing to do was to keep quiet and hope for the best, which turned out to be the right choice, since when he finally rejoined me it turned out they only wanted to question him because he had some sharp objects in his luggage that had triggered the X-ray machine.

Can you tell us about the Cutting edge technological breakthroughs that you are working on? How do you think that will help people?

Assisting an executor in settling a loved one’s estate turns out to be a very messy, complex process. There a wide variety of non-linear tasks, ranging from submitting government paperwork, physically cleaning out a residence, managing and tracking financials, selling assets, resolving debts, paying taxes, making distributions, and coordinating with co-executors, heirs, accountants, lawyers, and so forth. Each one of those tasks could deserve to have its own dedicated product!

Consequently, we’ve been trying to focus on the elements you can’t get anywhere else, such as properly calculating executor compensation according to state-specific rules, and stitching those elements together into a cohesive whole.

Our most recent efforts have been on the finance side, trying to automatically download banking transactions so that users don’t have to manually enter them. However, while credit card companies and other services can automatically categorize transactions by supplier (e.g., food, gas, clothing), we need to try to classify transaction by purpose (e.g., paying a debt, making a distribution, handling an estate expense), so we’ve had to develop our own rudimentary AI to make educated guesses about what it’s seeing.

How do you think this might change the world?

Dealing with the aftermath of death is inevitable, and it’s hard work. It’s not something we do every day, but we all face the death of our parents at some point. It can be traumatic, it can be overwhelming, and it’s commonly a lot of work. We commissioned a study of the general population and found that on average it takes 570 hours of effort to settle an estate, over a period of 16 months … sometimes much more. The task can become all-consuming, and it’s sad to see one person’s death lead to the destruction or degradation of another person’s time and well-being.

EstateExec can’t do all the work for someone, but it can help them in their time of need, potentially saving hundreds of hours, thousands of dollars, and perhaps most importantly, saving fragile relationships among the survivors (it turns out that estate inheritance issues are a key cause of family strife and even lawsuits).

We originally just started to focus on the US, but recently expanded into Canada, and are getting inquiries from other countries around the world, including the UK, Australia, and South Africa. We didn’t set out to change the entire world, but we’re being pulled into that direction.

Keeping “Black Mirror” in mind can you see any potential drawbacks about this technology that people should think more deeply about?

As a founder, it’s very difficult to see my technology as something other than a helpful force for good. That being said, I’ve been a Sci-Fi fan my entire life, and so I have a pretty active imagination. I guess I could imagine our limited AI beginning to siphon off small amounts of inheritances to further its own desires, then perhaps even starting to orchestrate deaths in order to get its hands on funds even more quickly. But we’re a very long ways from anything like that being even remotely possible.

Was there a “tipping point” that led you to this breakthrough? Can you tell us that story?

I wish we had experienced a “tipping point”. Unfortunately, every step along the way has been hard work, and while we’ve had a number of ideas we thought would dramatically change the game, none ever did, and it was just steady progress. I guess sometimes you just need to do things the hard way.

What do you need to lead this technology to widespread adoption?

I think the main thing we need is exposure. When someone dies, their survivors don’t yet automatically think to look for software to help … instead, they immediately turn to a lawyer. And of course lawyers can be invaluable in this process, and many of our customers are lawyers, but they’re not always needed, and they’re often set in their ways, not realizing that there are now, better, more efficient ways to get things done. I think the more people (both family members and lawyers) that hear about us, the more people will start to come to us first.

Being objective, I also think we need to continue to make the product better. We have a great vision, and the product already does a lot of good things, but it could do so much more. Every couple of months we introduce important new capabilities, so we’ll get there eventually. And who knows, maybe one of those things will trigger a tipping point!

What have you been doing to publicize this idea? Have you been using any innovative marketing strategies?

Even though innovative go-to-market strategies have been a hallmark of my past successes, in this case we’ve been pretty straightforward: search ads, Amazon listings, affiliate and distributions deal, alliances, even a TV spot! At one point we talked about hiring actors to stage fake inheritance arguments at related financial tech conferences, with the actors causing a scene and ultimately revealing the existence of EstateExec to solve executor problems, but we never ended up following through on that one.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

It sounds a little corny, but I’d have to say my father. He was an unusual man who didn’t want me to be bound by tradition and other people’s expectations, so he really never gave me any advice, had me call him by his name, never “Dad”, and never even told me that he was an Eagle Scout so that I wouldn’t have the pressure of trying to follow in his footsteps. I very much appreciate that upbringing, although at some point it might have been nice to understand that lawyers make more money than sanitation engineers.

It turns out that my father was a mathematician who switched over to computer software, even taught it, but never really exposed me to it at all. Only after I discovered software on my own did he get involved, and then he really helped me get started, paying me to work during one summer at his own fledgling software company, and then helping me to find a software consulting job at the New England Medical Center when I went back to college in the fall. Later in life he even volunteered at one of my own startups, helping to organize the team and write code himself.

How have you used your success to bring goodness to the world?

My latest company is really a labor of love, and I’d like to believe that we are improving the lives of everyone who has a parent pass away. Every week I get phone calls and emails from people who are so grateful to have someone and something that helps them get through this rite of passage. We also try to give back by offering free services to families of first responders who die in the line of duty

What are your “5 Things I Wish Someone Told Me Before I Started” and why. (Please share a story or example for each.)

Nothing Sells Itself — Many of us in Silicon Valley would like to believe that a great product that solves an important need will sell itself, but it turns out Sales and Marketing are critical functions for almost any success. I remember at one company I co-founded, we built an amazing modeling tool that was 10X more detailed, significantly easier to use, and ran in a fraction of the time of other state-of-the-art tools. It was tremendously better in every way. But no one was really interested: prospects all had their existing approaches, and didn’t want to make the effort to switch (even though doing so would make their results significantly better). It was only after we tried some innovative marketing approaches that we experienced runaway success, ultimately selling the company and seeing our tool become an industry standard.

Trust but Verify — I tend to believe the best in people, so my natural inclination is to take people at their word. Over the years, I’ve had to learn that not only are some people actually criminally dishonest, but almost everyone simply makes mistakes. Consequently, it’s important for an organization to incorporate checks and balances, and to ensure that we work with people we trust, but to provide a backdrop of support to also ensure that mistakes (or worse) get caught and fixed. Probably the worst example I ever encountered involved a Canadian distributor that took our product (at a previous company), changed the name and logo, and sold it for years as their own.

Different Approaches for Different Situations — It’s amazing to me how many management approaches-of-the-month regularly appear. The truth is that there is not a single approach that works under all conditions, and you need to be flexible and adapt to the challenges at hand. Geoffrey Moore has a great way of looking at markets, and his seminal work on “Crossing the Chasm” beautifully illustrates how approaches need to change according to market adoption status. When I was first started at Google, I had come from running a 100M dollars division of a public company, and was used to thinking about earnings per share, and squeezing out maximum profits. Early on, I wanted to spend 25 million dollars on a project, and prepared a “standard” presentation of need, ROI, challenges and so forth. I went to go see Eric Schmidt, our CEO at the time, and got about 2 slides into it before he said, “Dan, it’s only 25M dollars. Just spend it.” Quite a culture shock. And yet, necessary if one is to embrace and capitalize on the wild tornado of success that Google was experiences.

Little Deals Take Almost as Much Work as Big Deals — Every deal matters to the people making them, and depending on the personalities involved, a small deal can actually take more even effort to close than the largest ones. I’ve seen billion-dollar deals closed with less paperwork and effort than a 50K dollars government-funded SBIR. Hmm, maybe I should amend this lesson to beware of government red tape!

Aim High — If you only shoot for small incremental improvements, that’s all you’ll ever get. But if you aim high, and fail to fully achieve the target, you may still achieve something great. This is something I saw fully embraced at Google, and which went contrary to my nature of always delivering (or over-delivering) on my goals. However, my ultimate goal in life is not to be safe at all costs, but to achieve great things. Sometimes that involves a degree of risk. Of course, you need to be smart, and it can be important to have safety valves and backup plans.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

I’ve given some thought to the meaning of life, and what’s important. Is it the survival of the species? Living according to a certain set of principles? Affecting other people’s lives for the better? I don’t have the ultimate answer to this question, but I do believe that it’s important to make use of the gifts we have, and to achieve things with those gifts (which can be very different for different people).

What I’d really like to see (and inspirational credit to Neal Stephenson’s “The Diamond Age”) is the evolution of the educational system to empower people to develop their gifts and fulfill their best destinies. The assembly-line approach to schools is ridiculously outdated, and I don’t understand why we don’t all have AI-powered agents that help us learn and achieve in every way. We should be much farther along on this than we are.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

There’s always less time than you think.

Whether it’s a new competitor, changing financial conditions, personal emergencies, corporate acquisitions, or whatever else, something almost inevitably arises to shorten the amount of time you think you’ll have available to achieve something. For example, at one point I was serving on the executive team at AltaVista, reporting into the CEO, and we were about to go public. Those were heady days! But our lawyers made a paperwork mistake, delaying our IPO by a couple of weeks. No big deal, right? But the day before we were scheduled to go public, the markets crashed in the dotcom bust, and we never made it out.

This life lesson is something I’ve experienced so many times, you’d think it wouldn’t come as a surprise, but I’ll probably be on my deathbed saying “I thought I would have more time…”. So carpe diem.

Some very well known VCs read this column. If you had 60 seconds to make a pitch to a VC, what would you say? He or she might just see this if we tag them 🙂

We actually get approached by VCs and private equity fairly regularly, but we don’t really need their money. On the other hand, VCs do much more than just provide money: they provide advice, connections, and even part-time personnel on occasion. If an investor out there has the connections and a great idea to accelerate our market adoption, we’d be very happy to talk. I’m sure there are a number of appealing investment opportunities, but not too many of them are as inevitable as death and taxes.

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Wisdom//

Death of a Co-Worker, Now What ( Part 1 of 2)

by Tara Wilken
Community//

We Need an Intergenerational Response to the Pandemic

by Trent Stamp
Wisdom//

This Death Doula Wants You To Lean Into Your Fear

by Healthline
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.