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Freelance to Founder

Freelance to Founder

Your First Hire Could Save You… or Sink You

Freelance to Founder · Oct 6, 2026 · 21:36

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Christine Olivas has a calendar that won't quit and a pile of projects she keeps saying no to. The obvious move is to hire, but she knows the wrong hire at the wrong time just creates a bigger, more expensive mess. Preston and Christine walk through how she went from solo freelancer to a 24-person team: the signs that show it's time, the first role worth filling, and the traps that keep freelancers overwhelmed even after they bring on help.



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Episodes: Freelance to Founder

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