This episode is about the deal he says he'd never do again.
In Part 5 - the final episode of this conversation - Dylan Koch, off-market real estate investor and operator in Cincinnati, breaks down what happens when the underwriting is wrong and the money's already spent.
This was not a bad-deal problem. It was a constraint problem: DSCR requirements, a low appraisal, and $70,000 he had to bring back to the closing table on a refinance that didn't work out as planned.
We cover: Why the 1% rule no longer works in high-property-tax counties The negotiation tactic he uses on every seller call, and the psychology behind it The refinance mistake that cost him six figures in unplanned capital Why he's hiring his third acquisitions manager and what he's changing this time How he and his wife run an annual life-vision conversation most operators skip
If you're a founder, operator, or investor managing debt, underwriting risk, or a growing team, this conversation will feel familiar.
This is a practical breakdown of what happens after the deal closes and the numbers don't cooperate.
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Chief Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.
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