In this week’s episode of the Merchant Sales Podcast, James Shepherd sits down with Chris Del Grande, payments entrepreneur and ISO operator, for an in-the-weeds conversation on scaling merchant portfolios through the 1099 agent model. They break down what it really takes to grow at scale - where agents struggle, how ISOs can better support them, and why the 1099 channel remains one of the biggest opportunities heading into 2026.
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In this week’s episode of the Merchant Sales Podcast, James Shepherd sits down with Chris Del Grande, payments entrepreneur and ISO operator, for an in-the-weeds conversation on scaling merchant portfolios through the 1099 agent model. They break down what it really takes to grow at scale - where agents struggle, how ISOs can better support them, and why the 1099 channel remains one of the biggest opportunities heading into 2026.
As the payments landscape continues to evolve, how should ISOs, agents, and software providers approach 2026—by going all-in on vertical-specific solutions or by refining generalized offerings that can serve a wider market?
In this solo episode, James Shepherd shares hard-earned insights from his experience running both CCStorage, a vertical-specific solution, and Stackably, a more generalized tech platform. He breaks down the advantages and challenges of each approach and offers practical advice on how to align your strategy for growth, innovation, and long-term success in the coming year.
Whether you’re building software, growing an ISO, or rethinking your 2026 roadmap, this is an episode you won’t want to miss.
Merchant Sales Podcast
In this week’s episode of the Merchant Sales Podcast, James Shepherd sits down with Chris Del Grande, payments entrepreneur and ISO operator, for an in-the-weeds conversation on scaling merchant portfolios through the 1099 agent model. They break down what it really takes to grow at scale - where agents struggle, how ISOs can better support them, and why the 1099 channel remains one of the biggest opportunities heading into 2026.
