Three Years as CEO. One Hard Shutdown.

I took an internal side project at an existing company - a rough idea for a cannabis point-of-sale system - and launched it into a fully operational business in under a year. Oregon was legalizing recreational cannabis, and every dispensary needed compliant POS software. We were early.

I ran Bloom as CEO for approximately three years. We acquired dispensary clients across Oregon. I handled everything a CEO handles: product direction, client relationships, operations, hiring decisions, and the financials that keep a startup alive month to month.

Product-market fit never materialized at the scale we needed. The cannabis POS market attracted well-funded competitors faster than we could differentiate. I made the call to shut down rather than burn through capital chasing a market position we could not hold.

This is the case study I am most honest about. Not every venture works. But the judgment to shut down a company you built - before it becomes a liability rather than an asset - is a skill that only comes from having done it. I have made the hard call. I know what it costs. And I know it was the right decision.

Three years as CEO taught me things you cannot learn as an employee. How to evaluate product-market fit honestly, not optimistically. How to read a P&L and know whether next month is real or fiction. How to tell clients the truth when the truth is bad news.

Every engagement I take now is informed by that experience. When I advise on product strategy, I am not theorizing. When I recommend killing a feature or pivoting a positioning, I have made those calls with my own money on the line.