Matthew Diakonov: From Moscow to Meditation to AI Data Entry Automation
A conversation with Matthew Diakonov for Mother of Success
The Interview
Xiao He: Matthew, thank you for joining us today! To start, could you give readers a quick self-intro?
Matthew Diakonov: I grew up in Moscow and wanted to be a founder since I was about six. My first “business” at nine was selling newspapers to schoolmates. Then I discovered a CD-ROM burner and—illegally—copied and sold computer games. That bought me my second computer. I got into programming around 15, entered university via a CS Olympiad, and then did short stints at McDonald’s, appliance sales, and a bank before spending five years as a business consultant. After that I started my first software company—we sold it after two years. Five other startups didn’t work out. When the war started, I left for the U.S., started again from scratch, and now I’m building a media/automation company with my co-founder, Louis. We’ve fundraised and are working with design customers.
Xiao: Did your family encourage your entrepreneurial streak?
Matthew: My father used to give me money if I get good grades in school. That’s how I learned the value of money. When the grades slipped, I found alternative ways to make this income.
Xiao: In college you studied computer science, but you went into consulting at Accenture instead of pure software engineering. Why?
Matthew: One thing—it was too boring to be a software engineer for me. Also the technical bar in Moscow is much higher than in other countries. I wasn’t a great software engineer at that time. It was better to balance my career and learn business skills instead.
Xiao: You lived and worked in multiple countries. What was that like?
Matthew: I did like nine countries where I lived at least two months. Two years in the UAE—Dubai and Abu Dhabi. Accenture relocation was smooth. But consulting was intense, and the work felt very similar everywhere. It was pretty hard, so I didn’t enjoy it.
Xiao: What kinds of projects were you working on?
Matthew: Very different projects—consumer goods companies and transportation, airlines. Mostly cost-reduction projects: where are you overspending versus competitors and how do we cut? Often it meant reorganizations and changes in the back end or back-office operations.
Xiao: Looking back, did you enjoy consulting?
Matthew: Not really. The motivation felt off. I wanted to build things that help people.
Xiao: Tell us about your first startup.
Matthew: We built a CRM/operations system for small hotels and short-term rentals—connecting Airbnb/Booking.com channels to property managers for bookings, housekeeping, inventory, pricing. Around 2014–2016 this was an obvious leap beyond paper/Excel. It started as software I needed while running my own small rental operation. Other operators wanted it, so I left Accenture and went full-time.
Xiao: How did that business evolve, and why sell?
Matthew: We didn’t have experience. I didn’t do the right thing. Instead of just selling software, we pushed for leases and long agreements, hired people—ops and other things—which was like a nightmare. It wasn’t very scalable. When we tried to scale, it was long negotiations, ten-year agreements, hiring ops teams. My co-founder wanted out, so we sold part of the company. He left. I tried to continue, but the remainder fragmented. Some entities shut down, and another co-founder is still running a related business back in Russia.
Xiao: What did you try next?
Matthew: We tried property management for long-term real estate: a “no-agent” flow—self-tours via camera and digital locks; e-sign and e-pay everything. On paper it scaled. In practice, people weren’t ready. Renting is a big, high-price item. Paying rent is like a third of your income. People want a human in the loop.
Xiao: That was around 2017. Do you think people would be more ready now?
Matthew: It’s much better nowadays, but I think it’s still gonna take like 50 years for people to change.
Xiao: Fast-forward to moving to the U.S. in 2022. How was that transition?
Matthew: Brutal. In Russia I was late-seed with a 10-engineer team and had raised around $1.5 million (big locally). In the U.S., none of my reputation transferred. I had to reset to IC, relearn coding solo, and improve my English. It was uncomfortable and humbling.
Xiao: Your English today is excellent. How did you improve?
Matthew: Classes almost every day—30 to 60 minutes—focusing on accent and clarity. After about three years you see real progress. I’m not done; I expect to keep polishing for another 10 years.
Xiao: You work seven days a week, meditate, swim, and study English. How do you fit it all in?
Matthew: The first app I built in the U.S. was a time tracker. I actively log activities; weekly reports keep me honest. Awareness plus intention gives you better outcomes. My week is a simple loop: sleep, meditate, work, exercise, English, meditate, sleep. Lately I moved workouts to evenings; it works for me.
Xiao: When did meditation enter the picture?
Matthew: About a year after moving. Things kept failing. I had passive income from Russia, but it was shrinking; I had no friends or partner here, and my projects weren’t working. I slipped into depression and had recurring nightmares. Friends swore by meditation—one did a 10-day Vipassana and rebuilt her life fast. I tried a short two-day intro and then a 10-day course. On day eight I felt a deep shift. From there, life improved quickly.
Xiao: What are you building now?
Matthew: Louis originally started screenpipe—24/7 screen and audio capture to create a personal archive you can query and feed to AI. It went viral multiple times and made around $100k, but daily usage wasn’t there. Meanwhile, companies asked to use it for automation. That demand pulled us into business workflow automation built on recordings and observations. That’s where we’re focused now—fundraised and working with design partners.
Xiao: How did you and Louis team up? Any advice on finding a good co-founder?
Matthew: I wish I could have a good advice. It’s like a market, right? Supply and demand and opportunity sets. If you’re new to a country, consider working at a startup here first so you know strong people by output, not résumé. Otherwise expect trial and error. I worked with around 20 potential co-founders. Hackathons are underrated—one intense day shows how someone operates. Also, many great people already work on their own idea. Instead of insisting others join your idea, sometimes the higher-leverage move is to join theirs if you strongly believe in it. That’s what I did with Louis: I saw his GitHub and cadence, kept in touch, and when timing aligned, I joined him. I’m grateful to him. Then it started to work out.
Xiao: Any film, book, or content you’d recommend to founders?
Matthew: The best movie, I think, is Forrest Gump. Just doing repetition like a normal guy can still lead to extraordinary outcomes. A book by Ray Dalio, I forgot the name for a moment, yes, Principles. And YC—if somebody is looking to start up, start with YC’s videos. Watch one a week, and try to apply it in real life.
Closing
Consistency compounds. For Matthew, that’s time-tracking, English every day, swimming, and meditation—paired with honest pivots and the humility to reset. Sometimes the smartest founder move is to join the right person on the right idea—and then build.
Interview by Xiao He for Mother of Success.