Category Archives: Startups & Founders

The Money Plumbing Founders Get Wrong

A Q&A on payment processing, chargebacks, float, reserves, failed renewals and cross-border fees: how premium really moves, the costs that rarely make the budget, and the calls you only get to make cheaply once. Insurtech decks love a twelve-slide pricing model. The pipes get zero slides. Then the first processor statement shows up and the…

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Sponsor the Small List: Why 4,000 Devoted Readers Can Beat a Million Skimmers

A Q&A field guide to finding, pricing, negotiating, writing and tracking niche newsletter sponsorships | October 2026 Every founder eventually stares at an ad dashboard at 1 a.m. wondering where the money went. Here is a cheaper place to put it. Small, niche newsletters sell a reader who asked to be there and trusts the…

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Make a Forecast and Keep Score: Why the Founder With Receipts Beats the Founder With Predictions

Predictions are cheap. Every pitch deck, podcast and year-end LinkedIn post is stuffed with them. The rare move is the second half of the job: going back later, lining your call up against what happened, and printing the result where people can see it. That second half is where credibility gets manufactured, and Warren Buffett…

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Pick the Vertical With Data, Not With a Hunch

Sizing a staffing niche with labor statistics, posting volume, fee norms and competitor density, plus the signals that should send you somewhere else entirely. Part One: Why Your Gut Makes a Lousy Market Analyst 1. Why does almost every new staffing firm pick its niche the same way? Because the hunch is free, fast and…

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