The Idea: Most founders get one exit. Ethan Bloch just got his third. In 2013, Bloch launched Digit - an app with a simple but brilliant premise: connect your bank account, and let AI automatically squirrel away small amounts of money into savings before you even noticed it was gone. No willpower required. No manual transfers. Just quiet, compounding savings, done for you. Bloch had already sold his first startup, Flowtown - a social media SaaS tool he built as a teenager - for $4.5M. But Digit was different. This was his category-defining swing. By 2021, Digit had 600,000 paying subscribers and had quietly helped millions of Americans save for emergencies, vacations and down payments. Oportun came knocking and Bloch sold for $211M. Most founders would have retired. Bloch started over. This was the beginning of Hiro Finance.
The Execution:
- 2009: Bloch founds Flowtown, a social media marketing SaaS, and sells it for $4.5M - his first exit, built as a teenager. Exit number one in the bag.
- 2013: Bloch launches Digit, an AI-powered automated savings app. The core insight: most people don't save because saving requires effort. Remove the effort, and savings happen automatically.
- 2017-2021: Digit grows to 600,000 paying subscribers and manages hundreds of millions in automated savings for everyday Americans. It expands from savings into investing and full neobanking.
- December 2021: Oportun acquires Digit for $211.1M - $112.6M in cash plus $98.5M in stock. Bloch stays on to lead the business unit. Exit number two.
- 2024: Having seen the potential for AI to transform personal finance, Bloch quietly founds Hiro Finance - an AI personal CFO tool that lets users model financial scenarios, stress-test decisions and build full financial plans in minutes. Backed by Ribbit Capital, General Catalyst and Restive.
- Late 2024: Hiro launches publicly and within five months is managing plans for clients with over $1 billion in combined assets. The team? Just 13 people.
- April 2026: OpenAI acquires Hiro Finance in a deal that brings the entire team to Sam Altman's company. Hiro shuts down on April 20. Bloch describes it as a chance to pursue the mission "at a much larger scale, for a much broader audience." Exit number three.
The lesson? Ethan Bloch's entire career has been built on one thesis: people are bad at the boring stuff, and software can fix that. From social media management to automated savings to AI financial planning, he's always been selling the same thing - remove the friction, let the technology do the work. He's been right three times. The fact that OpenAI bought him to build this into ChatGPT suggests that the fourth time might be the biggest of all.