This is a conversation as told ethan blockFounder and CEO of Digit. He just launched his 15th project, a financial planning platform called hiro. Condensed and edited for clarity.
I started my first serious business at the age of 13, even though I had never even heard of the word entrepreneurship or knew what it meant until I entered college.
You could call it a project.
I imported electronic equipment from China, especially PlayStation controllers and memory cards. I created a website called Blochardware, named after my last name. Back in 1998, this was an early e-commerce store before paying online with credit cards was commonplace, and it was actually quite painful.
We were selling everything cash on delivery. This means that the postman will come to the customer’s house with the item, pick up the money order, and mail the money order to me.
But even before that, I was a kid who thought financial software was fun. When I was 10 years old, I used to play Quicken and write pretend checks for fun.
entrepreneur bug
My father is an immigrant from the Soviet Union. He came to America in the ’70s. My mother’s family has also lived here for a long time from Eastern Europe. My father was an entrepreneur. He owned a used clothing business and my mother later started her own company. That was exactly the situation in our household.
Growing up around that kind of independence influenced me.
I’ve always had an innate or natural problem with not liking being told what to do. I want to be the one who tells people what to do. When I was a student, this was really painful, but once I started my own business or started a project, I felt like the world opened up to me. I could create whatever I wanted and help people however I wanted. It was a natural fit.
Hiro is my 15th challenge. It wasn’t a dream, but it was an idea I had wanted to realize for years.
What is Hiro?
Orson Scott Card’s science fiction series “Ender’s Game” features a character named Jane, an AI who helps the main character, Ender, with his taxes. Ender is the one who saved the world, but he doesn’t know how to do something so mundane. Jane helps him.
When I first read this series, I thought, “Everyone should have a Jane.”
That was many years ago, but the idea has stayed with me. I didn’t know what was going to happen.
My previous company, Digit, was an attempt to do just that. We created this guide to create a financial guide that gives everyone access to the kind of support usually reserved for the wealthy. What we finally unlocked was automatic savings, and it worked. We’ve helped millions of people save billions of dollars, but the conversational guide elements we envisioned weren’t yet a reality.
Then ChatGPT came out.
This kind of technology has never existed before, and suddenly we can do things that seem almost magical. Combining a large-scale language model that is very good at financial mathematics with a rigorous, verifiable financial planning engine makes truly sophisticated financial planning a reality for anyone who wants to get serious about their financial future.
Hiro targets high-net-worth clients with incomes somewhere in the top 30% of their geographic area.
Users sign up and have a short conversation to create a financial plan. You can test scenarios such as “What happens if my income changes?” — and Hiro instantly shows you how it impacts your net worth and financial independence timeline. You can open up the math to see and verify exactly what’s going on.
Beneath the surface, Hiro has a complete financial planning and tax engine. You can go into more detail if you want, but most people just talk, ask questions, try different scenarios, and explore. We’ve also added starter prompts about financial independence, life changes, home buying, and more.
The key to success is to try, fail, and try again.
If you are an entrepreneur, the most important way to win is to get reps. This is not a lot of pressure to put on yourself, especially if it’s your first time.
We do something because we love it, we are interested in it, we are curious about it. The first 13 companies all went to zero. He then sold Flourtown for $4.5 million. And I just sold Digit for over $230 million.
This is a timeline of all the projects I’ve worked on so far.
1996: I sold computer video games on Ebay. 1998: Stock day trader during the telecommunications and internet boom.
1998: On sale now Blochardware is an e-commerce store that sells Playstation and later Dreamcast accessories.
2000:Started IT service business.
2002: Launch of the foldable mobile computer “COMTOP”.
2004: Launched EMB Networks for Ultra-Broadband Internet Access.
2005: He started a children’s charity called PureHealth.
2005: We launched Parlor Room to win prizes in online poker and other skill-based gaming contests.
2006: We started OpenSermo, an Internet news network.
2008: We launched Financial Fuzz, a social network focused on financial news.
2008: I started WSYK, an early Youtube/iTunes video blogger focused on current events.
2008: We launched “The Way To Build Wealth,” a video podcast focused on educating viewers on the basics of investing.
2009: On sale now Flowtown is a b2b SaaS focused on helping small businesses connect with their customers on social media. Acquired by Demandforce for $4.5 million.
2013: On sale now Digit means algorithmic savings and has helped consumers save $9 billion. It was acquired by Oportun for $238 million.
2023: Released AI financial planner “hiro”.

