25 Years on eBay, Bipolar, and the Chaos That Built FRANK

Today Matthew Freeman talks about his quarter of a century selling on eBay, living with bipolar, and building FRANK, an AI system designed to give time back to small business sellers: I am Matthew Freeman and for 25 years, eBay has been my anchor.

From selling a few items in a one-bedroom council flat to completing over 50,000 transactions, it has been the constant in a life that wasn’t always predictable. For most of my career, I hid a crucial part of my story: I have bipolar disorder. I feared the stigma and the assumptions people might make about my capability to run a business.

Yet, while facing hospitalisation and personal setbacks, the predictable rhythm of ecommerce — wake up, check messages, list, sell, pack, repeat—provided the very stability I desperately needed. The Question That Anchored Me While my wife, Tanya, has been my voice of reason and rock for the last decade, it was my mum who gave me my guiding philosophy.

Near the end of her life, suffering from Parkinson’s dementia, I sat by her hospital bed and explained how my business worked. She listened carefully, then asked one profound question: “Does it make you happy?” My answer was “Yes!” My mum died just days later.

Of everything she could have asked me during those final days, those five words are what stayed with me. ‘Does it make you happy?’ is still a question I ask myself today. It did. And it still does. That question remains the filter through which I run my business today.

Engineered by Chaos: The Birth of FRANK In 2026, my journey evolved when I embraced eBay Live. As a seller specialising in electronics, I loved sharing the nuance of why a specific camera or camcorder was valuable. But new requirements meant that every item shown on stream needed a full, detailed listing beforehand.

An hour of spontaneous live selling suddenly required hours of tedious administration. Refusing to accept this, I built FRANK, an AI system born directly out of a practical seller’s frustration. FRANK isn’t just another tech trend; it is built on a few core principles: Human-in-the-Loop: AI can be confidently wrong.

If FRANK isn’t absolutely certain, the human decides. Capturing Context: AI excels at the what, but after 25 years of selling, I know the seller owns the why. AI should augment that expertise, not replace it. Compressing Administration: We recently proved FRANK can process 100 item listings in just 22 minutes, eliminating hours of repetitive typing.

The TikTok Challenge When I was challenged on TikTok to prove that the system actually worked, I took 100 items from a box, moved each one in front of the camera and then returned it to the box while FRANK generated the listings. The run took around 22 minutes, followed by quality control.

What those 22 minutes represent is hours of repetitive administration potentially compressed into a fraction of the time. That’s where my interest in AI lies – Not AI because it’s fashionable, not generating content simply because a machine can generate it, and definitely not removing the seller from the process.

It gives a small business owner their time back! We often ask how many more listings somebody can create or how much more revenue a business can generate. Those are valid measurements, but perhaps we should also ask ‘How much of someone’s life can good technology give back to them?’ That’s become one of the principles behind FRANK.

Why I’m talking about bipolar now? For most of my adult life, I’ve worried about being stereotyped because I have bipolar disorder. So I hid it. Recently, I’ve started talking about it more openly. I’ve realised I don’t want to spend the next 25 years hiding a part of who I am. Running a business with bipolar hasn’t always been easy.

There have been breakdowns. There have been hospital admissions. There have been financial and personal setbacks. There have been periods of rebuilding. Routine has mattered enormously.

But there have also been 25 years of selling – More than 50,000 transactions, thousands of customers, a community, a marriage, and now an AI system that I could never have imagined building when I sold those first few objects from a council flat. I don’t think one part of that story cancels out another. They’re all part of the same story.

AI With a Human Heart This year, I have been shortlisted for the eBay Business Awards 2026 AI Expert Seller Award (You can vote for me here). But for me, this represents a collision of two 25-year journeys: learning how to sell, and learning how my own mind works.

FRANK has a human in the loop because, after 25 years of ecommerce, I still believe the human matters. And after all the technology, AI models, live streams, listings and thousands of transactions, I still come back to the simplest question anyone ever asked me about my business… My mum’s question. “Does it make you happy?” Yes! It does.

And perhaps that’s the best way I can describe what I’m trying to build with FRANK: AI with a human heart — designed to give selle