Willing
Summer 2015AcquiredThe best way to make your legal will.
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The best way to make your legal will.
Explore the risks and possibilities with a prompt for ChatGPT, Claude, or your agent.
Willing (legal entity: Bequest, Inc.) was a Miami-based legal technology startup founded in 2014 by Eliam Medina and Rob Dyson. Operating from Y Combinator's Summer 2015 batch, the company built a digital estate planning platform that allowed users to create a legally valid will in all 50 states in under ten minutes — no attorney, no forms, just button-click questions. It later expanded into a full estate planning suite covering trusts, powers of attorney, and living wills, alongside a funeral home price-comparison marketplace. By the time of its acquisition in November 2019, Willing had served more than 500,000 families on approximately $7.1 million in total venture capital.[1]
Willing's failure as a standalone business was not a product failure — it was a distribution failure. The company proved consumer demand was real and that UX simplicity could unlock a historically friction-blocked category, but it could not build the distribution engine needed to justify independence. Its original monetization model — free wills subsidized by funeral home referral fees — was quietly abandoned, and the paid SaaS model that replaced it could not generate the scale that $7.1 million in capital and a seven-person team could sustain.
MetLife acquired Bequest, Inc. in November 2019 and embedded Willing's technology into Hyatt Legal Plans, described as the world's largest legal insurance company.[2] The outcome was a textbook "feature absorbed by platform incumbent" acquisition: Willing built the technology and proved the market; MetLife provided the distribution Willing could never independently achieve. Founder Eliam Medina stayed at MetLife for approximately two years before departing to found Telora, a startup incubator for students and hackers.[3]
Eliam Medina's path to founding Willing was unusually circuitous for a consumer legal-tech startup. He held a dual degree in Business Management and Computer Science from Florida International University and a Columbia MBA, and had spent five years as a consultant at McKinsey's Miami office before joining 3G Capital's operational team at Burger King as a vice president.[4] By any conventional measure, he was on a high-trajectory corporate career path — not the profile of someone about to teach himself to code and build a will-creation tool.
The inflection point was personal. When a medical emergency forced Medina to help his aunt navigate end-of-life planning, he encountered an industry that his McKinsey training and private equity experience had not prepared him for: slow, expensive, emotionally fraught, and structurally opaque.[5] The experience gave Willing something that many legal-tech startups lack — authentic founder-market fit rooted in a specific, documented pain point rather than a market-size calculation.
Medina's response was characteristically high-conviction. He resigned from Burger King, enrolled in Bloc — a 12-week online coding bootcamp — and built the initial version of Willing as his class project.[6] This is a notable signal: rather than hiring a technical co-founder and staying in a product/strategy role, Medina chose to acquire the skill himself. The resulting product was functional enough to take to Y Combinator.
Co-founder Rob Dyson joined as CTO. Dyson and Medina had been friends since high school in Miami, making this a trust-based founding team rather than a skills-matched one assembled through professional networks.[7] Dyson's professional background and technical credentials are not documented in available sources — a gap that makes it difficult to assess the founding team's technical depth independently of the product they shipped.
The YC application process itself revealed Medina's instinct for narrative. He reportedly sent personalized urns to YC partners as part of his pitch — a move that demonstrated both his willingness to lean into the taboo nature of the product and his understanding that getting people to engage with death-adjacent planning required breaking through emotional avoidance.[8] The stunt worked: Willing was admitted to the Summer 2015 batch.
The company was incorporated as Bequest, Inc. — a name that signals the founders' awareness of the brand sensitivity around death — but operated publicly as Willing, a name chosen to suggest agency and intentionality rather than morbidity.[9] The dual naming strategy reflected a sophisticated understanding of the psychological barriers the product needed to overcome.
2014 — Eliam Medina and Rob Dyson found Bequest, Inc. (d/b/a Willing) in Miami, FL. Medina had recently left Burger King/3G Capital, taught himself to code at Bloc, and built the initial platform as a class project.[6]
Summer 2015 — Willing participates in Y Combinator's Summer 2015 batch. Reported as the fastest-growing startup in its cohort, having logged more than 10,000 wills.[10]
June 1, 2015 — Willing.com launches publicly. Founders project 10,000 wills within a few months.[11]
July 13, 2015 — TechCrunch covers Willing's launch, detailing the free-will plus funeral-home-marketplace business model and the $20.7B funeral / $5B estate planning market opportunity. Investors at this stage include YC, 500 Startups, Sound Ventures, and Gary Vaynerchuk.[12]
2015 — Willing raises capital across Seed and Series A rounds (specific amounts undisclosed); total lifetime raise reaches approximately $7.1M from 10 investors including Accomplice VC, Crux Capital, and Ironfire Ventures.[13]
2015–2019 — At some point in this window, Willing pivots from a free-will-plus-funeral-marketplace model to a paid tiered SaaS model. The timing and rationale are not documented in available sources.
November 20, 2019 — MetLife and Bequest, Inc. (d/b/a Willing) announce a definitive acquisition agreement. Terms undisclosed. At this point Willing has helped 500,000+ families create legal documents and has a team of approximately 7 people.[14]
Late 2019 — Post-acquisition integration begins: Willing's technology is embedded into MetLife's Hyatt Legal Plans, converting a consumer product into a B2B2C distribution channel.[2]
2021 — Eliam Medina departs MetLife after approximately two years post-acquisition. Kris Borer (Willing's CTO at acquisition) remains as CTO of MetLife Legal Plans.[3]
2023 — Medina founds Telora, a fellowship and incubator helping hackers and students build startups, drawing on lessons from the Willing journey.[15]
Willing's core product was deceptively simple: a web-based tool that walked users through the creation of a legally valid last will and testament using button-click questions rather than open-ended form fields. The entire process took under ten minutes.[16] The UX insight was that the primary barrier to will creation was not cost or legal complexity — it was friction and emotional avoidance. By eliminating blank forms and replacing them with structured choices, Willing removed the cognitive load that caused most people to abandon the process.
The legal credibility of the output was not sacrificed for simplicity. Documents were state-specific, drafted in collaboration with estate planning attorneys, and tracked relevant statutes across all 50 states and the District of Columbia.[17] This was a meaningful differentiator: pure software competitors risked producing documents that failed state-specific validity requirements, while Willing's attorney-backed approach gave users — and, critically, their families — confidence that the documents would hold up.
Over time, Willing expanded beyond the basic will into a full estate planning suite. The platform came to include revocable living trusts (which allow assets to pass outside of probate), living wills (healthcare directives), durable powers of attorney (authorizing someone to act on your behalf if incapacitated), and transfer-on-death deeds (for real property).[18] This expansion transformed Willing from a single-document tool into a comprehensive estate planning platform — a logical product progression that also justified higher price points in the eventual paid model.
The second product pillar was a funeral home and cemetery price-comparison marketplace. The strategic logic was explicit: Medina observed that most funeral planning decisions happen under acute emotional distress, immediately after a death, when price comparison is psychologically impossible. Willing's marketplace was designed to enable advance, objective comparison — removing the emotional distortion of in-person funeral home visits.
As Medina put it in 2015: "The dream here is never having to step foot in a funeral home or cemetery, which are very difficult environments to make objective decisions in. We're trying to make the process as objective as possible."[19]
He elaborated on the behavioral insight driving the marketplace: "Nobody likes to plan for a funeral. No one says, I had an awesome weekend, I went to four funeral homes. Typically, this all happens because someone close to you passed away or got sick. When you start the process this way, there is not a lot of price comparison going on, and that is why we believe in starting early."[19]
The product evolution — from free will tool to paid estate planning suite — reflected a significant business model shift. The original pricing was free for the basic will, with monetization routed through the funeral marketplace. The later paid model introduced three tiers: an Individual Plan at $69, a Homeowner Plan at $299 (including a revocable living trust), and an Ultimate Care Plan at $399 (including overnight document delivery and unlimited changes for three years).[18] The pricing architecture suggests Willing was targeting a mid-market consumer segment — above the free tier of competitors like DoYourOwnWill, but below the cost of engaging an estate planning attorney (typically $1,000–$3,000 for a comparable document set).
What distinguished Willing from alternatives was the combination of legal rigor, UX simplicity, and speed. LegalZoom offered broader legal document coverage but a more complex user experience. Quicken WillMaker was desktop software with a steeper learning curve. Rocket Lawyer operated on a subscription model with attorney access. Willing's sub-10-minute, mobile-friendly, attorney-backed will creation occupied a specific niche: the user who wanted a real legal document without the friction of any of the alternatives.
Willing's primary target was the approximately 55% of adult Americans who lacked a will or estate plan — a massive, structurally underserved population.[20] Within that broad population, the product's UX and pricing positioned it toward digitally native consumers who were aware of the need for estate planning but had not acted due to friction, cost, or emotional avoidance. The product's life-event framing — Medina explicitly cited having a baby, buying a home, or "planning for the unexpected" as trigger moments[21] — suggests a target demographic of adults in their 30s and 40s experiencing major life transitions.
MetLife's post-acquisition characterization of Willing's users as "a digitally native audience unlikely to go see an attorney for estate planning services"[22] confirms this positioning. Willing was not competing for the high-net-worth estate planning market (where attorneys remain dominant) or the elderly market (where in-person relationships matter). It was competing for the middle — the majority of Americans who needed basic estate planning and would never initiate it through traditional channels.
Willing targeted two adjacent markets: a $5 billion U.S. estate planning market and a $20.7 billion per year U.S. funeral industry.[20] The dual-market framing was central to the original business model: the will tool addressed the estate planning market directly, while the funeral marketplace addressed the funeral industry through a lead-generation model. In practice, the addressable market for a digital-first, self-serve estate planning product was a subset of the $5 billion figure — the portion of that market currently served by attorneys and traditional legal document services, minus the high-net-worth segment that would not self-serve regardless of UX quality.
Willing competed in a crowded field that included LegalZoom, Quicken WillMaker, Rocket Lawyer, Trust & Will, Lawdingo, Sequiter, and Willful.[23] The competitive landscape can be mapped along two axes that mattered most: distribution reach and product depth.
LegalZoom occupied the high-distribution, broad-product-depth quadrant — a well-funded incumbent with brand recognition across all legal document categories, not just estate planning. Its distribution advantage (direct traffic, SEO authority, brand recall) was structural and difficult to overcome on $7.1 million in capital. Rocket Lawyer similarly had broad distribution and a subscription model that created recurring revenue and user lock-in.
Willing competed on product depth within estate planning specifically, and on UX simplicity — a narrower but real differentiation. The sub-10-minute will creation was a genuine product advantage over LegalZoom's more complex flows. But product depth and UX simplicity are features that well-capitalized incumbents can replicate; they are not structural moats.
The more structurally significant competitive threat was the platform move that ultimately absorbed Willing: large insurers and financial services companies recognizing that estate planning was a natural adjacency to their existing customer relationships. MetLife's acquisition of Willing was not an isolated event — it reflected a broader pattern of financial services incumbents acquiring digital estate planning capabilities rather than building them. This dynamic made the standalone consumer legal-tech category structurally difficult: the highest-value distribution for estate planning products was embedded inside existing financial protection relationships (insurance policies, financial advisory accounts, employee benefits), and those distribution channels were controlled by incumbents who could acquire rather than compete.
Trust & Will, a close peer founded in 2017, pursued a similar consumer-direct model and raised significantly more capital ($60M+ as of 2023) — suggesting that the category required more capital than Willing raised to achieve standalone scale, and that the window for independent consumer legal-tech was narrowing as incumbents moved in.
Willing launched with a freemium model: wills were free, with monetization planned through the funeral home marketplace via lead generation and referral fees from funeral homes and cemeteries.[24] The founders explicitly stated that user data would never be sold — a commitment that narrowed monetization options from the outset.[11]
The strategic logic of the original model was coherent: free wills would drive high-intent user acquisition at scale, and those users — having just documented their end-of-life wishes — would be natural prospects for funeral planning services. The funeral industry's price opacity (a well-documented consumer problem) created genuine value in a comparison marketplace. The problem, which the available evidence suggests but does not confirm, is that the conversion from "created a will" to "actively compared funeral homes" was insufficient to build a sustainable revenue engine. The behavioral gap between estate planning (a cognitive exercise done at a desk) and funeral pre-planning (an emotionally loaded, in-person process) may have been wider than the product architecture assumed.
At some point between 2015 and 2019, Willing shifted to a paid tiered SaaS model: Individual ($69), Homeowner ($299 with trust), and Ultimate Care ($399 with document delivery and unlimited changes).[18] The timing and rationale for this pivot are not documented in available sources — the absence of any public explanation is itself a signal that the transition was not a triumphant product evolution.
Directional unit economics (inferred, not confirmed): With $7.1 million raised over approximately five years and a team of 7–10 at peak, Willing's annual burn rate was likely in the range of $1–1.5 million — consistent with a lean Miami-based operation. At $69–$399 per paid user, reaching breakeven would have required roughly 2,500–10,000 paying customers annually at the low end of that burn estimate. Whether Willing achieved this is unknown; no revenue figures were ever disclosed.
Willing's early growth metrics were strong relative to its capital base. The platform launched June 1, 2015, and hit 10,000 wills within months — meeting the founders' own projection and reportedly making it the fastest-growing startup in the YC S15 cohort.[10]
By acquisition in November 2019, Willing had helped more than 500,000 families create legal documents — wills, trusts, and powers of attorney — since its 2015 launch.[1] That figure represents approximately 100,000 document-creation events per year on average, or roughly one new family every five minutes around the clock. For a seven-person team operating on $7.1 million in total capital, this is a meaningful consumer scale milestone.
The investor roster reinforced the traction signal. Sound Ventures (Ashton Kutcher and Guy Oseary) and Gary Vaynerchuk were early backers alongside YC and 500 Startups.[12] The celebrity investor participation was likely a deliberate strategy: in a category defined by emotional avoidance, having culturally visible investors signaled that estate planning was a normal, modern behavior rather than a morbid preoccupation. Accomplice VC, Crux Capital, and Ironfire Ventures rounded out a 10-investor syndicate.[25]
Critical gaps remain: no conversion rate data (free-to-paid, will-to-funeral-marketplace) is publicly available, no information on user acquisition channels or demographics has been disclosed, and whether the 500,000 figure represents unique users or total documents created is ambiguous.
Willing's fundamental problem was not product quality — it was the structural difficulty of building a defensible, scalable consumer business in a category where the highest-value distribution channels are controlled by incumbents with existing customer relationships.
Estate planning is a life-event-triggered behavior. Users don't wake up thinking about wills; they think about wills when they have a baby, buy a house, receive a diagnosis, or watch a parent die without one. The companies best positioned to intercept those moments are not consumer legal-tech startups — they are life insurers, financial advisors, mortgage lenders, and employee benefits providers who already have relationships with customers at exactly those inflection points.
Willing's consumer-direct model required it to acquire users through paid marketing, SEO, and word-of-mouth at the precise moment of life-event trigger — a high-cost, low-predictability acquisition model. MetLife, by contrast, could embed Willing's technology into Hyatt Legal Plans and distribute it to millions of existing policyholders at near-zero marginal acquisition cost.[2] The acquisition was not a rescue of a failing product; it was a recognition that the product's value was maximized inside a distribution platform Willing could never build independently.
MetLife's Todd Katz confirmed this logic explicitly: "Willing serves a digitally native audience unlikely to go see an attorney for estate planning services."[22] The acquirer's framing — a distribution problem, not a product problem — is the clearest available evidence that Willing's ceiling was structural, not operational.
Willing's original monetization strategy — free wills as a top-of-funnel acquisition tool, funeral home referrals as the revenue engine — was strategically coherent but apparently insufficient. The model assumed that users who created a will would convert to funeral pre-planning behavior at rates sufficient to generate meaningful referral revenue from funeral homes and cemeteries.
The behavioral gap between these two activities was likely wider than the model assumed. Creating a will is a cognitive, desk-based exercise that takes ten minutes and produces a document. Pre-planning a funeral requires confronting mortality at a more visceral level, involves in-person or near-in-person service selection, and carries a much higher emotional load. Medina's own framing — "Nobody likes to plan for a funeral"[19] — acknowledged the behavioral barrier, but the product architecture assumed that removing price opacity would be sufficient to overcome it.
The evidence that the funeral marketplace failed is indirect but consistent: Willing pivoted to a paid SaaS model at some point between 2015 and 2019, the funeral marketplace is not mentioned in the MetLife acquisition announcement, and no press coverage of the marketplace's performance or scale exists in available sources. The pivot to paid SaaS was the team's attempted remedy — shifting from a two-sided marketplace model to a direct consumer revenue model. The outcome was a more predictable revenue stream, but one that still couldn't generate the scale needed to justify independence.
Willing raised $7.1 million across its entire five-year life.[13] For a consumer product in a taboo category requiring sustained marketing investment to overcome behavioral avoidance, this was a constrained capital base. The comparison to Trust & Will — a close peer that raised $60 million or more and pursued a similar consumer-direct model — suggests that the category required significantly more capital to achieve standalone scale than Willing's investors were willing to commit.
The team size at acquisition — approximately seven people[26] — is consistent with a company that had optimized for capital efficiency rather than growth. This was a rational response to constrained capital, but it meant Willing could not invest in the marketing, sales, and partnership development needed to build the distribution moats that would have made it defensible against incumbents.
The attempted remedy — raising from a celebrity-adjacent investor roster (Kutcher, Vaynerchuk) to generate cultural visibility and organic growth — was creative but insufficient. Cultural destigmatization of estate planning is a decade-long project, not a startup-timeline one.
The legal-tech estate planning category has a structural characteristic that makes standalone consumer businesses difficult: the product is a one-time or infrequent purchase (most users create a will once and update it rarely), which means there is no recurring revenue from the core product without artificial subscription mechanics. The highest-value recurring relationship in estate planning belongs to the financial services provider — the insurer, the financial advisor, the bank — who sees the customer annually and can prompt updates at life events.
This structural dynamic means that the most defensible position in digital estate planning is not a standalone consumer product but an embedded feature inside a financial services relationship. Willing's acquisition by MetLife was the market's verdict on this structure: the technology was valuable, but the standalone consumer business model was not.
No founder post-mortem or retrospective interview specifically addressing what Willing got wrong exists in available sources — a gap that limits the analysis to structural and market-level inference.
Willing proved that UX simplicity is the key unlock for taboo-category consumer products — but proved it at a scale that made it an acquisition target, not a standalone winner. The company's 500,000-family user base on $7.1 million in capital demonstrated that sub-10-minute will creation genuinely removed the friction barrier that had kept 55% of Americans without estate plans. The lesson is not that the product failed; it's that proving consumer demand in a taboo category is a necessary but insufficient condition for building a defensible standalone business when the highest-value distribution is controlled by incumbents.
The funeral home marketplace model — Willing's original monetization engine — illustrates the limits of behavioral adjacency as a business model assumption. Willing assumed that users who created a will (a cognitive, desk-based behavior) would convert to funeral pre-planning (an emotionally loaded, in-person behavior) at sufficient rates to generate referral revenue. The quiet abandonment of the marketplace model between 2015 and 2019 suggests this conversion did not materialize. Startups building two-sided marketplace models on top of free consumer tools should stress-test the behavioral distance between the free product and the monetization event — not just the logical connection between them.
Willing's acquisition by MetLife rather than a legal-tech or fintech player reveals where the highest-value distribution for estate planning actually lives. The acquirer was an insurance company with an existing legal benefits platform (Hyatt Legal Plans), not a legal-tech peer or a fintech aggregator. This outcome suggests that estate planning is most naturally embedded in existing financial protection relationships — life insurance, employee benefits, financial advisory — rather than discovered through consumer search. Startups in adjacent categories should map not just who their competitors are, but who controls the distribution channels their customers are already in.
Willing's celebrity investor strategy (Ashton Kutcher, Gary Vaynerchuk) was a creative but ultimately insufficient substitute for structural distribution. The strategy was rational: in a category defined by emotional avoidance, culturally visible investors signal normalcy. But cultural destigmatization operates on a decade-long timeline, while startup capital runs out in years. Willing's $7.1 million total raise — compared to Trust & Will's $60 million+ — suggests the company either could not raise more or chose not to, and that the celebrity investor signal did not translate into the sustained marketing investment needed to build consumer brand at scale.
Medina's post-Willing trajectory — founding Telora, a student startup incubator — suggests he drew lessons about early-stage company building from the Willing experience. Rather than founding another consumer product company, he moved to the meta-level of helping other founders navigate the early stages he had experienced. This is consistent with a founder who built something real, learned the structural limits of the category, and chose to apply those lessons in a different domain rather than re-run the same playbook with more capital.