Overview

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]

Founding Story

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.