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…
Category Archives: Startups & Founders
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…
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…
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…
Attention Management When You Are the Product
A Q&A for founders who are also the delivery team, the sales team, and the logo There is a particular flavor of tired that only arrives when you are the entire company. You end a client call at 2:15 and you were the deliverable. At 2:30 you are the sales department. At 4:00 a prospect…
The Newsletter You Actually Own
A Q&A on audience ownership, algorithm risk, and why the advice you give every client is the one you never took. You tell every client to own their audience. Then you build yours on rented land, from a landlord who can raise the rent tonight, under a lease you never read. I have 28,000 followers…
Write the Discovery Call Down
Your first call is a product with no spec sheet, shipped differently every time, by people who are guessing. It is also where the deal is actually decided. Here is what 35,000 observed calls, 519,000 recorded ones and one 16th-century Italian scribe have to say about that. Continue reading →