After Spending $40k, Giving Up a 6-Figure Job in NYC , and Living with My Mom for 2 Years to Work on My Now-Defunct Startup, I'm Back at it Again
From Failure to Fresh Start: My Journey Redefining the Encyclopedia Using AI
The Fall of Cicero
Back in February, I shut down Cicero.ly after 3 years of on-and-off work.
Our mission was to curate content from the world's leading thinkers. The hypothesis was simple: our information landscape is broken, and it's hard to find the signal in the noise. We could solve this by finding and curating high-quality content into a feed.
But here's the harsh truth: we ran out of money and the product was too hard to build. It was all completely self-funded and I could never raise despite talking to dozens of investors.
I spent almost $40,000 building it, moved back into my mom’s house for 2 years, and gave up on multiple years of a 6-figure salary in NYC to work on Cicero. I was completely broke.
Also, it didn’t help that we built something people didn't want enough. It's the #1 reason startups fail according to CB Insights (https://s3-us-west-2.amazonaws.com/cbi-content/research-reports/The-20-Reasons-Startups-Fail.pdf), and we fell right into that trap. I eventually figured out what people wanted, but just ran out of money before finishing it
Saving and Reflecting
After shutting down Cicero, I took a few months to save money and reflect. I continued my startup coaching and business consulting work, lived frugally and continued living at my mom's house, and most importantly, thought deeply about what went wrong and how to do better next time.
This period was crucial. It allowed me to approach my next venture with a clearer mind and a fuller wallet.
Enter Dediro: A New Vision
During this reflection, I realized that the core problem I wanted to solve was still valid, but our approach was off. That's when the idea for Dediro was born.
Dediro aims to change the way we all take in information by creating a new kind of encyclopedia using AI. Instead of just gathering content, we're making it easier to understand complex topics and giving it to you in whatever format you like best.
Why this vision? Because in an era of information overload and polarized discourse, we need a beacon of truth-seeking. We need a platform that doesn't just inform but transforms how people engage with knowledge.
Building the Dream Team
With this vision in mind, I knew I needed a stellar team. Here's how I made my first hires:
Full Stack Engineer #1: Found on Reddit /r/forhire. From Pakistan
Full Stack Engineer #2: Found on Reddit /r/forhire. From Egypt.
AI Engineer: Found on Upwork and worked on Cicero. I asked him to come back. From Tunisia
Total monthly burn rate for the team: $3500. It's lean, but we're all invested in the vision.
All of them are super young, super energetic, and extremely ambitious. Most people don’t hire inexperienced in my position. But I’ve worked with over 300 founders and executives at this point and one thing is always clear: Passion, motivation, and loyalty always outweigh experience. Check this Harvard Business Review article about how little experience matters: https://hbr.org/2019/09/experience-doesnt-predict-a-new-hires-success
My Interview Process:
#1 is a personality assessment from principlesyou.com
30 minute behavioral structured motivational interview. Use Claude of ChatGPT to come up with these questions and a rubric for them
Paid work assessment where they do code review on some existing code I had. All three of these people went above and beyond in the code review, took ownership, and came up with amazing ideas to take the product to the next level.
What's Next?
We're now in the process of building our MVP. But this time, we're doing things differently. We're validating even more than I did last time and building less. It’ll all be about quick shipping and keeping things as lean as possible.
I'll be sharing our progress, challenges, and learnings here regularly. If you're interested in the intersection of AI, knowledge curation, and personalized learning, I'd love to hear your thoughts!
You are all-in in this mission!