What matters most: An interview with Jennifer Xia Spradling of Freewill
Jenny's startup journey, Freewill's mission, and do young people need wills?
Hi all, nice to see you again! Coming to you from San Francisco once again, and apologies for the short delay in posts.
This week I was fortunate to do a Q&A with my old friend Jennifer Xia Spradling, Co-CEO of Freewill, a tool for free end-of-life planning that has also facilitated substantial donations to charity. I was inspired hearing about her startup journey, appreciated her tips for end-of-life planning, and I had to ask her, do I need a will?? (Spoiler: I think everyone does…) Read ahead!
Can you tell us a little about what inspired you to found Freewill and your path to founding a company?
Jenny: My path to starting a company was twisty! Out of college, I started working in management consulting. I was so lucky to get recruited into starting a company with two friends, Eric Glyman and Karim Atiyeh, on the side of our full-time jobs as consultants and bankers. It was a great learning experience, but I left before we got to the scaling phase of being a company for two reasons.
First, I suffered from imposter syndrome. I was unsure about whether people like me or my friends could be successful entrepreneurs. The great entrepreneurs in my mind were Steve Jobs, Bill Gates, and Mark Zuckerberg. I wasn’t selling lemonade at 6, or tinkering with computers at 8, so was I really smart or creative enough to start a company?
Second, job security. My parents are immigrants who know nothing about business. I had already had a job offer from a top tier private equity firm that was safe, and frankly paid a higher salary to 24-year-olds than I had ever heard of any adult being paid. They thought I’d be crazy to turn that down.
I got lucky in that a few things happened at the right times: First, Paribus sold to Capital One within a couple years of founding, showing me that indeed my friends (at least) were good enough to make great entrepreneurs. That gave me confidence. Second, my mentors in private equity (who have many friends who have “made it” in the US) pointed out that whenever I talked about Paribus I was way more excited than talking about leverage, and also pointed out no matter what I did I would have fall-back career options that would feed me and my family.
Finally, I met Patrick, my FreeWill cofounder within two weeks of starting business school. With cofounders, when you have founding chemistry (similar values, similar reasons for starting a company, very different experiences and skillsets) things are just easy. And he had a brilliant idea to start FreeWill after having spent his whole career being a pioneer in the digital fundraising space.
What does Freewill do and what is its mission and business model?
Jenny: FreeWill provides free online estate planning - wills, revocable living trusts, advance healthcare directives, and financial powers of attorney. We make it easy for people to leave money to charity in their wills, and our mission is to help raise $1T for charity in the next 30 years as Baby Boomers leave over $70T of assets to lucky beneficiaries. Our tools are completely free to consumers, and our business model is to provide white-labelled versions of our tools to nonprofits for an annual SaaS fee.
Who do you view as Freewill's primary competitors and how do you try to differentiate vs. them?
Jenny: FreeWill’s primary competitor is surprisingly the same on the user and nonprofit side - it’s inaction. Over 70% of Americans have no estate planning in place. That includes around over 40 million parents who haven’t appointed guardians for their children, and 40 million baby boomers who haven’t put any end-of-life plan in place. Top reasons why they haven’t done it: they are worried it’s too expensive, too complicated, and too scary. FreeWill solves the first two problems for most Americans. Most Americans who do make an estate plan go to see an attorney, because they think it’s the only option. If someone has a complicated estate - multiple marriages, a child with disabilities, a net worth of over $10M - this makes sense. Attorneys are experts in giving advice on particular situations. But the vast majority of Americans just need a simple will, healthcare directive, and financial power of attorney. They can get that for free on FreeWill from the comfort of their own homes.
What is one thing that has surprised you about end-of-life planning industry as you've learned more about the area?
Jenny: How fulfilling it is. A lot of people ask me, “Isn’t thinking about death all the time awful?” It’s really the opposite. End-of-life planning is really about helping people think about the things that matter most to them - their family, their friends, what gives them meaning and purpose in life, and then distilling those down to some powerful decisions they get to make at the end of their life. The things that matter most in life become part of my daily practice by osmosis.
From seeing a lot of end-of-life planning on your platform, do you have any general advice for readers in terms of how to think about this type of planning?
Jenny: Sure! Few things:
Just block off 20 min to take the first step, and you will feel so much better. Most of our users finish writing their entire will in less than 20 minutes. They are always surprised it so quick and painless.
The average gift to charity in a will is 3x larger than the cumulative lifetime giving of an individual. Think about every penny you rounded up or donated at a grocery store register or gave to a friend’s marathon fundraiser, added up, and multiplied by 3! If you are serious about making an impact on the world, a will is a surprisingly effective way to do it.
Think seriously about whether you need a trust. Attorneys are unfortunately financially incentivized to sell you the most complicated end-of-life planning vehicle that fits your circumstances. Most attorneys are good actors, but we’ve heard many stories of people who got their revocable living trust earlier than they needed to and were stuck with a lot of maintenance. Alternatively, perhaps in their state of residence a will vs. trust doesn’t make a big difference at all because the probate process is smooth. The internet is directionally helpful (although obviously not perfect) about these things, so do some desk research before starting your estate planning.
Being in this field I have to disclaim, I’m not an attorney or accountant, so none of this is legal or financial advice.
Many of the readers of this newsletter are in their 20's and 30's. Do they still need wills despite being quite young?
Jenny: Maybe! Tony Hsieh just passed away at 46 worth nearly $1B and didn’t have a will. If you think about having a will like an insurance policy with no up-front cost and no premium that you can change at any time for the rest of your life - it’s probably worth 20 min to get that policy in place. As you gather more wealth and dependents, you can keep leveling your will up, but the initial security is so cheap and easy to get.
It’s also worth talking to your parents about their end-of-life plans. Start with the advance healthcare directive - this is the document that helps you understand what their healthcare wishes are if they are incapacitated and unable to make decisions for themselves. It can be very hard to make medical decisions on behalf of your parents if they are sick and in the hospital, especially because many decisions also have serious financial consequences. It’s sad to think about, but it’s better to find out what your parents want while you can still ask! If they don’t have one, there are several free resources online that can help someone fill one out for free, and give instructions on how best to file with their preferred hospitals and doctors.