Ever wondered why that “free” POS hardware ends up costing so much later? Christopher Dryden, Esq., sits down with Magnolia Ventures’ Jessica Casto to pull back the curtain on modern payments strategy: how software-led distribution reshaped acquiring, why processor-agnostic design protects leverage, and where the fine print quietly shifts risk to the least prepared party. We move from the realities of US card economics—reward-heavy credit that pushes up costs—into the trenches of cash discounting and surcharging, where debit rules, tax exclusions, and state-by-state quirks can break a great pricing story if your product can’t adapt.

We talk through the rise of SaaS add-ons as vendors chase lost processing revenue, and we map the contract terms that matter most for ISVs, ISOs, and resellers: Schedule A transparency, onboarding responsibility, chargeback support, and residual ownership. Jessica shares a practical playbook for tech companies entering the US market—collect multiple processor proposals, compare effective margins not just splits, and engineer optionality so you can route, renegotiate, or switch without rewriting your stack. If you’re subsidizing hardware, pressure-test your payback periods against debit-heavy mixes and capped surcharges before you scale.

Education is a recurring theme. Too many operators and even CFOs don’t read merchant statements, miss pass-through fees, and get blindsided by portfolio-wide basis-point hikes. We make the case for productizing compliance: build configurable pricing engines that exclude tax, respect card-network caps, and flex with state regulations—and notify partners before merchants feel the change. If you sell software, payments isn’t an add-on; it’s a strategic capability. Tune in to learn how to negotiate liability, design durable revenue, and plan your exit on day one.

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**Matters discussed are all opinions and do not constitute legal advice. All events or likeness to real people and events is a coincidence.**

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A payments podcast of Global Legal Law Firm