Exclusive: Vanilla, backed by Michael Jordan and Vanguard, raises $30M

Vanilla, an estate planning fintech, raised $30 million in funding from a group of investors led by Insight Partners.

• Venture capital firm Venrock, basketball legend Michael Jordan, former Vanguard chairman and CEO Bill McNabb, and Vanguard itself joined the round.

Why it matters: Vanilla sits among a nascent class of startups seeking to use technology to simplify the complex world of death planning, in particular the financial part.

• In late 2020, Trust & Will raised $15 million to digitize the will-signing process. Earlier this year, Wealth — a company with a digital dashboard for managing estates — raised $16 million.

How it works: Estate planning comes with a knot of legal and difficult-to-track tax implications. Vanilla, which sells to investment advisors, aims to be a one-stop shop for the process.

• Vanilla says it can automatically calculate and recommend an optimized portfolio for estate taxes.
• "We had not planned to raise cash, but had a lot of inbound interest from VCs and we saw the chance to scale faster," says CEO Gene Farrell.

Of note: Having joined only in January, CEO Gene Farrell is realizing a long-time dream of becoming a CEO. It's been a long and twisty road for him.

• Amazon sued Farrell in 2017 after he left the company, accusing him of breaching a non-compete. Farrell had told Amazon he wanted to take a company public as CEO, and joined work collaboration startup Smartsheet.

• Amazon later dropped the suit. But Smartsheet CEO Mark Mader decided to stay on even after the company's IPO last year.
• It's all now in the past for Farrell, who says his relationship with his former Amazon boss (now Amazon CEO), Andy Jassy, is friendly again. Nor does he have any hard feelings against SmartSheet.

This article is a part of Axios Fintech Pro's daily newsletter. Read more about the deal here.