I spent nine months building a B2B voice AI company. The tech worked — the agents held real conversations, the data came back clean. The buying motion didn't. I made a hundred cold calls, hired SDRs, redesigned the pitch, pivoted the product. The market I chose moves slower than a bootstrapped company can afford to wait. The funding ran out before the market moved.
So I did what founders don't like admitting: I opened the job boards.
The reality on the other side was worse than I remembered. Four hundred new roles a day, maybe eight worth my time. My career doesn't fit one filter. AI, big data, marketplaces, SaaS, GameFi, eCommerce, Web3, infrastructure — as a founder, as an IC, and managing teams of 40 at scale. The bridges to my next role were non-linear; no job title could describe them. So every board showed me 5% of what mattered and buried it in noise. And applying well — reading the ad honestly, judging fit, re-tailoring the CV, writing a letter that isn't slop — takes an hour a role. Nobody has forty hours a week for that on top of interviews.
I'm a builder before I'm a candidate. So I built my caddie: a tool that walks the course ahead of me, scores every role against my actual career, and has the full application pack drafted by the time I sit down in the evening. It never sends anything — I take every swing. And every line it drafts, I can rewrite. It learns from each correction; by now it writes in my voice.
Then something shifted. Everywhere I looked — my feed, my chats, my old colleagues — people were struggling with this market, sending fifty applications into silence. Meanwhile I kept getting interviews. The difference wasn't my CV. It was the caddie carrying my bag.
So I turned it into a product. No pivot deck, no vision slide — a tool built out of necessity by someone inside the problem, shared with the people stuck in the same rough.
If you're mid-search right now: I know exactly what it feels like. That's the point.
