Justin Fineberg

Running a company and an audience at the same time

Justin Fineberg spends his days on two things most founders would tell you to pick between. He runs Cassidy, an AI automation platform used by enterprise teams, and he makes content about artificial intelligence for a following that has grown past 400,000 across TikTok, Instagram, X and YouTube. For him the two are not a distraction from each other. The audience came first, and it became the foundation the company was built on.

Cassidy's pitch is narrow and practical. It lets non-technical teams design, deploy and improve AI-driven workflows and agents without waiting on IT or stitching together brittle point tools. The platform connects securely to a company's own tools and knowledge, then uses that context to automate work like customer support, lead qualification and RFP processing. The idea Fineberg keeps returning to is simple: the person closest to the work should be the one who automates it.

That belief is why Cassidy exists in the shape it does. Instead of selling a black box that a technical team configures once and everyone else tolerates, the company puts the building tools in front of the people who actually run the process. When automation lives with the people doing the job, Fineberg argues, the results are more accurate, adoption comes faster, and small improvements compound into real productivity gains.

An invite that changed the plan

In 2020, Fineberg got early beta access to OpenAI's GPT-3. For a lot of people that would have been a fun weekend. For him it read as a signal about where technology was heading, and it reset his ambitions. Two years later, in 2022, he left his product manager role at Blade to build something around it.

He did not go it alone. He teamed up with Ian Woodfill, a long-time collaborator and engineer whose strength was the no-code space. Woodfill's understanding of how to make software approachable and Fineberg's push for accessible AI lined up neatly. In 2023 the two co-founded Cassidy, aiming to give organizations an easy way to build custom generative AI without a team of specialists.

The timing was not luck so much as preparation meeting a wave. Fineberg had grown to around 30,000 followers making AI content before ChatGPT launched. When mainstream interest arrived, the audience he had built covering a subject nobody yet cared about expanded quickly. He was already there when everyone else showed up.

Distribution before the product

Most B2B software gets built first and marketed later. Fineberg did the reverse. He grew a following of hundreds of thousands - reported as high as 500,000 - before Cassidy had a product to sell. That order gave the company something rare at launch: a large group of people who already trusted him to explain AI in plain terms.

The content is not a side hustle bolted onto the business. It is the reason the business can reach the people it wants to reach. When Cassidy talks to enterprise buyers, it does so from a brand that has spent years demystifying the exact thing those buyers are nervous about. Fineberg has been featured in Bloomberg, Fortune and AdAge, and has spoken at companies including Amazon, Healthline and Microsoft.

The through-line across everything - the videos, the platform, the pitch to a Fortune 500 - is accessibility. Fineberg's argument is that the hardest part of enterprise AI was never the model. It is getting the model to understand a specific business and putting that power in the hands of people who do not write code. Cassidy is his answer to that, and the $10M Series A led by HOF Capital in 2025, with participation from The General Partnership, Neo, Alumni Ventures and others, is the market agreeing it is worth funding.

A career, in order

What he has built

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