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Jenny Xia Spradling: “Make talking about death less stigmatized”

Make talking about death less stigmatized. Dying without a will and other estate planning documents can leave loved ones in a bad situation. While already grieving, your loved ones are also arguing about what your wishes are, because they never had the chance to talk to you directly about your wishes. It’s an incredibly selfless […]

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Make talking about death less stigmatized. Dying without a will and other estate planning documents can leave loved ones in a bad situation. While already grieving, your loved ones are also arguing about what your wishes are, because they never had the chance to talk to you directly about your wishes. It’s an incredibly selfless thing to talk about your final wishes with your family in advance.


As part of my series about “individuals and organizations making an important social impact”, I had the pleasure of interviewing Jenny Xia Spradling.

Before FreeWill, Jenny worked at McKinsey and Bain Capital, where she helped launched the firm’s first impact investment fund. She is also a co-founder of Paribus, later acquired by Capital One.


Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path? Can you share the most interesting story that happened to you since you began leading your company or organization?

I got invited to attend the Gates Foundation Philanthropy Conference in Seattle during my second year, and I remember feeling so special because I grew up around Seattle, and working at the Gates Foundation was my dream. It turned out that founding FreeWill was actually my dream job, but it was fun to relive my childhood dream anyway!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

When we first started FreeWill in graduate school, we did hundreds of user interviews to make sure that our product was actually filling a need that people had in their lives. One comment that kept coming up was “I love the product, but I’m not sure about the name. It reminds me of whales. You know the movie Free Willy?” We heard this so many times we started doubting the name. As this anxiety grew, we came up with another 10 alternatives, and almost bought a new domain name.

Luckily, we re-analyzed our user data before we made any moves. The “Free Willy” comment was mostly coming from millennials. In fact, no baby boomers had made the reference. Since we were initially targeting baby boomers, we decided to keep the name, and we are so happy we did. Our users now tell us consistently that the name is memorable and easy! Key learning: “Focus on your target customer segment.”

Can you describe how you or your organization is making a significant social impact?

FreeWill provides free online wills and estate planning to all Americans. There is a chronic lack of access to law in the US, because it is perceived to be expensive, complicated, and time-consuming. We wanted to fix that by making a warm, intuitive, and completely free solution that anyone could access. In addition, we make it really easy to leave money to charity in our wills. People on FreeWill donate 6x more than the national average, and we have helped people pledge 1.5 Billion dollars to charities through our tools.

Can you tell us a story about a particular individual who was impacted or helped by your cause?

My co-founder and co-CEO, Patrick just got this text from an old friend yesterday: “Not sure if this is still your number. Just wanted to say that my aunt, who is dying, just used FreeWill yesterday to create a last-minute will, and my family is so relieved and grateful. They don’t have much money or time, and they felt it was incredibly straightforward. I wanted to pass that feedback on. Thank you so much for what you do. ❤” We get messages like this all the time.

Are there three things the community/society/politicians can do to help you address the root of the problem you are trying to solve?

  1. Make talking about death less stigmatized. Dying without a will and other estate planning documents can leave loved ones in a bad situation. While already grieving, your loved ones are also arguing about what your wishes are, because they never had the chance to talk to you directly about your wishes. It’s an incredibly selfless thing to talk about your final wishes with your family in advance.
  2. All estate planning should contemplate giving to charity. Since we started FreeWill, we’ve seen lots of other online estate planning companies make charitable giving a bigger part of their platforms. That makes us so happy to see! We hope that lawyers also incorporate charitable giving as part of their estate planning conversations.
  3. Prioritize access to law in addition to safety. Sometimes regulations can be helpful for keeping bad actors out, but other times it can stifle creativity and access. We believe the legal system is being overly cautious towards safety, and it has harmful effects on society. We strongly believe that the legal system needs to serve and protect not only those who are wealthy and educated, but also those who are less fortunate. Online tech solutions can be really helpful in covering basic legal needs, and we hope that the regulation around online legal document providers allows more players like FreeWill to provide access to law online. Lawyers are really important for solving complex cases, and should focus their time and attention on those — they shouldn’t be charging hundreds of dollars an hour for simple documents.

How do you define “Leadership”? Can you explain what you mean or give an example?

Leadership is making the people around you better. It comes with a mindset of serving others, and not oneself. This can be as simple as defending someone’s view in a group conversation so that they feel supported and gain confidence.

What are your “5 things I wish someone told me when I first started” and why. Please share a story or example for each.

  1. Anyone can start a successful startup. FreeWill isn’t the first startup I founded, but it is the first one I really stuck with. The biggest reason why I didn’t stay with the first is because I didn’t think that a person like me — young, introverted, no startup experience — could be an entrepreneur. I thought people were born to be entrepreneurs or not. It seemed that in every famous entrepreneur’s biography that had been selling lemonade since the age of six. Now I know quite a few successful entrepreneurs, and one of my biggest learnings is that they are just “normal people” with hard work and good luck!
  2. Invest in diversity in your first 10 hires. We made a commitment from the very beginning to have 50% female engineers. This meant doing 50 interviews per person we hired to make sure we were sourcing and hiring the absolute best. It was a really costly thing to invest in early, but it’s paid dividends. It’s now much easier for us to hire female engineers because it is likely that underrepresented minorities have friends and networks who have other underrepresented minorities in them. This is true of all types of diversity, not just gender.
  3. The best part about being a founder is that you get to pick who you work with. My favorite part of my job is that I get to work with some of the smartest, kindest, creative, and joyful people that I’ve ever met. I learn from them everyday. This matters so much more to me than making a lot of money or becoming famous which I’d imagine is what a lot of people think being a founder is all about.
  4. Mission-oriented businesses are the way of the future. I used to work in impact investing and one fundamental debate we would have is whether the category of social enterprises should exist. We expected that nonprofits and for-profits could be extremely successful, but there is still a lot of skepticism in the industry that a company with multiple bottom lines — social and financial — can exist and do well. I no longer have skepticism, mainly because I see the smartest and best millennials choosing to work at mission-oriented businesses. Where the talent goes, the returns will follow.
  5. Cultivate relationships with your old friends. It’s easy to get absorbed into your startup when you first get started. The people outside my company have kept me sane, and been some of my most important advisors. Many of the hardest decisions you will make are decisions that come down to your values. The people who know you best can guide you through those better than anyone, even if they don’t have any experience in what you are doing.

You are a person of enormous 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. 🙂

Implementing a carbon tax as a sustainable, scalable system for combating climate change.

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

“I hope you are taking time to breathe.” — My best friend since age 11, Marissa. Life moves so quickly, and it’s so easy to get overwhelmed. Breathing is a helpful way to re-center in the present. At FreeWill, we actually start every group meeting with three deep breaths so we can leave the noise of whatever was happening before the meeting behind.

The time in which this was most helpful for me was at my wedding. I was crying so hard that I couldn’t start walking down the aisle! Luckily the “three breaths” came to me at just the right moment, and it was just enough to center myself so I could take those first steps.

Is there a person in the world, or in the US with whom you would like to have a private breakfast or lunch with, and why? He or she might just see this, especially if we tag them. 🙂

Andrew Yang.I’m so excited that more Asian Americans are joining politics. I think there is a stereotype that Asians can’t be charismatic or lead or influence. We are hard workers, but we can’t be at the top. I love that he’s such a vibrant counterexample, and I hope there are more coming!

How can our readers follow you on social media?

https://www.linkedin.com/in/jenxia/

This was very meaningful, thank you so much. We wish you only continued success on your great work!

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