Making Something From Nothing: Jenny Xia Spradling Of FreeWill On How To Go From Idea To Launch

An Interview With Fotis Georgiadis

I wish I knew right at the start how satisfying simply closing the books would be each month, after the initial “idea” morphs into a rapidly growing, successful company. It felt like a milestone that first month in 2017, with the second month not too far behind. If I knew how satisfying even the little things would still be in year five, I probably would have left my previous job earlier.

As a part of our series called “Making Something From Nothing”, I had the pleasure of interviewing Jenny Xia Spradling.

Jenny Xia Spradling is the Co-founder and Co-CEO of FreeWill, a social-good enterprise offering online tools that empower Americans to address commonly faced estate planning needs and make charitable donations in tax-advantaged ways, all for free. Before FreeWill, Jenny worked at McKinsey and Bain Capital, where she helped launch the firm’s first impact investment fund. She is also a cofounder of Paribus, later acquired by Capital One.

Thank you so much for doing this with us! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

Thank you, too, for speaking with me!

I grew up outside Seattle with my sister and two loving parents who both immigrated from China during the 1980s in search of a better life for their daughters. My parents’ story is one you’ve probably heard quite often — they started over from scratch when it came to connections with people, language, and culture. Their journey and my Asian American identity each plays a shaping role in who I am.

When I was young, we visited our family in China often and I realized that the only difference between me and my cousins in China — who didn’t have many of the things I had — was that I was lucky. I was born at the right place at the right time. My parents were some of the first immigrants who left China after the Cultural Revolution.

Because of that lived experience, I believed from a young age in the idea of using philanthropy to correct luck-based inequalities. I always dreamed of working for the Gates Foundation. I began in the private sector, and I learned a great deal. Eventually, I felt that it was time to draw on those lessons and make a difference.

That’s why I started FreeWill with a classmate from business school, my co-CEO, Patrick Schmitt. We’ve been able to help drive transformative gifts to charity, and I think what we’ve been able to accomplish — almost $5 billion committed to nonprofits in just five years — is already beyond my loftiest dreams.

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

I always go back to a lesson I learned during business school: emotions are our bodies’ quickest form of pattern recognition. I grew up bottling and ignoring emotions to get through challenging situations, but I’ve come to realize that reaction squanders helpful information.

For example, there haven’t been many stories of Asian American women who have founded and scaled notable brands, so when I told my parents about my plan to leave a stable, high-paying job to eventually start my own company, they showed concern. Not because they didn’t want big things for me, but because they’ve never met or read about someone like me for whom entrepreneurship worked out. I needed to create that pattern for them.

Then, in 2020, I planned to have my first child. I think I felt more anxiety because I hadn’t seen an existing pattern of founder-moms who’d scaled their companies to unicorn status. I hope I can build patterns for other women who may feel less fear in jumping into entrepreneurship after seeing me succeed.

This lesson is also important to keep in mind when running a company. Often, when I feel a particular emotion in my capacity as an executive, I stop and try to unpack it. Often, there’s useful information hiding in plain sight when I recognize and address my emotions in this way.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Anne-Marie Slaughter’s 2012 cover story in the Atlantic Monthly entitled “Why Women Still Can’t Have It All” has always stuck with me. It was a groundbreaking piece that sparked a dialogue relating to women balancing motherhood with career advancement. It was published a month before I started my career, so the timing was impactful for me.

The piece resonated because I had big professional dreams, but I also wanted to become a great parent, just as mine were for me. I thought about the piece every now and again over the years, but it became quite relevant to me personally when the time came for me to become a mom.

I was a founder by then, and the fact is, there aren’t too many founder/moms. Practically everyone I talked to told me there was never a “right time” to have a baby, and I couldn’t help but think I was beginning to really feel what I’d read a decade before.

Luckily, it’s worked for me. My company has grown a lot in the past year, acquired a company, launched a crypto giving product, and raised a Series B investment — all since my return from maternity leave. At the same time, I know there are different phases of motherhood — some easier than others. I’m happy to say that I think things are really getting better every time I re-read “Why Women Still Can’t Have It All”, and I enjoy revisiting the piece from time to time to take stock.

Ok super. Let’s now shift to the main part of our discussion. There is no shortage of good ideas out there. Many people have good ideas all the time. But people seem to struggle in taking a good idea and translating it into an actual business. Can you share a few ideas from your experience about how to overcome this challenge?

The first obstacle comes right at the beginning. We all want the good life — to be able to enjoy dinner with our friends, spend time with our families, all while saving money. Getting to the good life can be challenging. For those who already enjoy some semblance of it, the idea of exchanging comfort and stability for something uncertain is simply not for everyone. My family certainly tried to talk me out of it.

Second, finding the right co-founder(s) is everything. Starting a business requires many different skill sets, and those skill sets rarely all reside within the same person. When I started business school, I knew I wanted to do something to help boost philanthropy. I was lucky enough to meet my co-founder Patrick two weeks later. He had extensive experience in nonprofit fundraising, and there’s no way FreeWill would have happened without what we each brought to the table. In the lean early days, having a co-founder also helped psychologically. We were always able to keep each other on track and support each other through the hard times. We like to say we have some overlapping strengths, but very few overlapping weaknesses, and that puts FreeWill in the best position.

Lastly, a good idea is only a good idea if your customers think so. Many founding teams spend too much time building what they think the market needs and not consistently validating their hypotheses with the market. You cannot spend too much time with your customers in the early days. Patrick and I were grateful to learn a lot of this methodology from Lean Launchpad, a class we took at Stanford together.

Often when people think of a new idea, they dismiss it saying someone else must have thought of it before. How would you recommend that someone go about researching whether or not their idea has already been created?

There’s no right way to do this, but vetting potential ideas is certainly easier to do today than it was 20 years ago.

Invariably, there will always be someone who has created at least some aspect of your idea already, but I’d tell any budding entrepreneur not to let that ever thwart them. Often, existing ideas can be meaningfully different, with underlying business models that may not be viable, and not all leadership teams are built to execute. For example, an investor recently told us that he had seen 50 online wills companies cross his desk that he passed on before deciding to invest in us. We had a different core customer and go-to-market strategy.

It’s important for potential founders to put themselves in the shoes of target customers in researching products that could potentially be available to solve for a particular need. One way to do this is by plugging terms and questions into Google and clicking around, with cookies enabled. Between searches and browsing activity, ads will be served that will provide some insight into who is viable enough to be spending on marketing.

Industry lists are also very important to look at, and of course, there is no substitute for finding subject matter experts who can speak knowledgeably about an industry.

For the benefit of our readers, can you outline the steps one has to go through, from when they think of the idea, until it finally lands in a customer’s hands? In particular, we’d love to hear about how to file a patent, how to source a good manufacturer, and how to find a retailer to distribute it.

Building a tech platform is in many ways different from starting a company that sells physical goods, but at the same time, there are parallels.

When we came up with the idea for FreeWill, we wrote up a values statement as well as a relatively succinct business plan. When we filed legally to establish our new entity, we decided to codify our values by becoming a public benefit corporation. Next, our market research and competitive analyses showed us that our biggest competitors were time and money — people didn’t prioritize taking the time to write their wills, and they definitely didn’t want to spend much. We did A/B testing to see how best we could remove friction and we found that 95% of people won’t do an estate plan if the cost is just $20, so we figured we might as well make it free.

From there, we spent virtually all of our time on the product. We invested heavily in legal resources to underlie our estate planning product, and we hired our first two employees to help nonprofits understand the opportunity

What are your “5 Things I Wish Someone Told Me When I First Started Leading My Company” and why?

I wish I knew earlier how beneficial it could be to tap into talent all across the country, rather than limiting our searches to a single city. We’ve been growing at more than 100% year-over-year, and after two years of remote work, the idea of limiting our searches to our headquarters in New York City sounds crazy to me, and impractical. The COVID-19 pandemic has been tragic in many ways, but there are some ways in which it’s helped drive progress. It challenged our preconceived notions that in-person work was the only way we could be successful. We’ve been able to attract amazing talent so much more easily with a remote-first workplace.

I also wish I knew how truly helpful working remotely could be for working parents. I always valued in-person collaboration, but I’ve seen the virtual model work in a sustained way and we’re committed to remote-first work at FreeWill. It allows increased flexibility for parents and caregivers. I’m among them and it’s allowed me to perform at both of my roles far more effectively as a founder-mom. At a time when many women have been leaving the workforce, we’ve thrived in terms of retention. I’m quite proud of that.

Third, the fact that we’re mission-based has been such a critical pillar of our recent success that it makes me smile anytime I think back to the debates we had when we first founded FreeWill. Granted, we were simply asking tough questions of ourselves in response to the feedback we received to not become a public benefit corporation, but I wish we spent the time elsewhere. Millennials and members of Gen Z, in particular, care deeply about purpose. As we recruit, retain and try to attract customers, our mission has played a central role.

Fourth, there’s definitely a greater need for founders to be intricately involved in every detail when a startup is in its infancy. But shortly after — especially once a product is in the market — founders add more value by asking the right questions and making good decisions rather than simply hustling more. Circumstance forced me to micromanage less, but it was a journey, and I was constantly anxious about the things I couldn’t control. My maternity leave forced me to truly let go of a number of responsibilities, however, and I saw that my teams delivered stellar results in my absence. Now that I’m back, I focus more on things only the CEO can do, and it’s helped me become a more effective leader.

Lastly, I wish I knew right at the start how satisfying simply closing the books would be each month, after the initial “idea” morphs into a rapidly growing, successful company. It felt like a milestone that first month in 2017, with the second month not too far behind. If I knew how satisfying even the little things would still be in year five, I probably would have left my previous job earlier.

Let’s imagine that a reader reading this interview has an idea for a product that they would like to invent. What are the first few steps that you would recommend that they take?

Try to figure out your product-market fit. Figure out what your value proposition would be relative to the next-best option in the market. If it’s not 10x better, try something else. Life is too busy to switch to a marginally better solution. Your customer acquisition costs will be too high, and your time and talents could be used solving a bigger problem for the world. Don’t assume you’ll simply execute better than the next person, or that your charisma will get you the investment to win the space.

Next, consider your addressable market — if it’s not $1B or more, that’s ok, but recognize it will be harder to get venture capital investment. Instead, you have might need to take a more slow and steady approach to building your company. The smaller the addressable market is, the harder it will be to find your customers and grow.

Finally, get your ideas and product in the market to test with customers as soon as possible. It might be good to do a survey as market research to test out your ideas. You could even consider investing in a prototype and running some social media campaigns using a landing page to get a sense of customer demand in different markets.

If all of that checks out, reach for the sky and file your articles of incorporation!

There are many invention development consultants. Would you recommend that a person with a new idea hire such a consultant, or should they try to strike out on their own?

I think ultimately founders need to strike out on their own, but it’s never a bad idea to work with a couple different folks early on if it means getting some additional voices in the mix. Having someone to challenge your ideas and ask tough questions about ideas they have no emotional attachment to adds tremendous value for any executive or founder. However, make sure you aren’t giving up too much value too early. Make sure if you are giving out equity, for example, that it’s structured in a way to reward early team members who stick it out for the long haul.

With FreeWill, we were lucky to have the Stanford business school network. It gave us access to seed investors, some of whom had a great deal of experience, it gave us access to faculty advisors as well as other budding entrepreneurs to weigh in. But early on, founders should be making the key decisions.

What are your thoughts about bootstrapping vs looking for venture capital? What is the best way to decide if you should do either one?

Start with your values — why are you starting a company? Be real with yourself — is it money, fame, to solve a particular problem, to have control over decision-making? How much does scale matter to you?

Venture capital is incredibly helpful but just one tool amongst many to achieve your goals. Funds are incentivized to support boom or bust companies — either ones that will win big, or fail. You need to think about whether the market you operate in is big enough (or touches other big markets you can expand into) to warrant venture capital.

You are more likely to achieve fame with venture capital, and less likely to achieve control over decision making (One-fifth of founders in venture-backed companies get replaced). As for money, it depends on what your risk tolerance is. Would you rather have a big shot at a medium amount of money (would lean towards bootstrapping), or a small shot at a big amount of money (would lean towards venture).

Ok. We are nearly done. Here are our final questions. How have you used your success to make the world a better place?

Everything I’m doing with FreeWill is designed to make the world a better place. I think that by helping charities fund good causes while at the same time helping people get access to comprehensive estate planning tools for free is a legacy I can be very happy about.

At the same time, as a founder and a co-CEO, I think it’s very important to use my platform to make the workplace a better place. That means making it a better place for women, for working moms, and for people of all backgrounds and ethnicities. By doing that in my own workplace, I hope I can leave my mark. I consider this the most important work I do.

You are an inspiration to a great many people. 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.

It’s very hard to pick one. First, when we chose to incorporate as a public benefit corporation, that meant codifying our mission — which is to help people do the most good for the people and causes they love. We have a fiduciary responsibility to that mission, and I’d love for it to become a movement. We know that as Boomers age, there will be an historic $70 trillion generational wealth transfer and that can be a vehicle for a lot of good to be brought to a lot of people through funding philanthropic causes.

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

I’d love to meet Melinda French Gates. I’ve always greatly admired the impact that the Gates Foundation has had on global health and poverty, specifically their founding values, such as valuing each human life equally.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.