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Freelance to Founder

Freelance to Founder

You Need a Vacation

Freelance to Founder · Sep 14, 2026 · 19:17

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Dave's agency works, for now. Pricing, delivery, client issues—it's all running through his head, and he's starting to feel it crack under the weight. Jesse P. Gilmore, founder of Niche In Control, joins Preston and Sabrina to map out exactly which systems to build first, from client onboarding to capturing the tribal knowledge that only exists in a founder's brain. Sabrina pushes the conversation further, asking what systemizing looks like when your service is literally yourself. It's a practical, no-fluff roadmap for anyone ready to stop being their business's single point of failure.

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Episodes: Freelance to Founder

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