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

Apr 28, 2022
Illustration of piggy bank as a skull and crossbones

Illustration: Eniola Odetunde/Axios

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.

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.

Details: The deal, which values the company at around $120 million, is the company's first fundraise under new CEO Gene Farrell and marks the launch of Vanilla's growth phase.

  • The company plans to reach $1 million in revenue this year, Farrell tells Axios.
  • "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 Farrell, noting Vanilla has doubled its head count since January, to more than 50. The company was last valued at around $60 million, after a funding round in August.

Of note: Having joined only in January, 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 2018 IPO.
  • 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.

Editor's note: This article was updated to correct Smartsheet's IPO year to 2018.

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