Connect with Orel: https://writestack.io
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What does it really take to build a product as a solo founder?
In this episode of thinkfuture, host Chris Kalaboukis speaks with Orel, software developer and founder of WriteStack, a tool designed specifically for Substack creators to manage notes, content, and publishing workflows.
Orel’s story isn’t an overnight success. Before WriteStack, he built and shut down 12 failed startups. Instead of quitting, he used each failure as feedback—refining his understanding of product-market fit, marketing, and community-building.
We cover:
Why most startups fail—and what you actually learn from them
The evolution of WriteStack from an AI outline tool to a full Substack productivity platform
The importance of listening to users and pivoting quickly
How community feedback shaped the product roadmap
What it’s like working 6 hours a day, 7 days a week as a solopreneur
Why marketing matters as much as code
The entrepreneurial mindset required to survive long-term
Orel believes that even if AI eventually automates tools like WriteStack, the mindset of building, adapting, and serving a community will always matter.
If you’re a Substack creator, indie hacker, solopreneur, or SaaS founder, this episode is a grounded look at persistence, iteration, and building tools for real users.
