Freelance to Founder
Freelance to Founder
Millo
Your First Hire Could Save You… or Sink You
21 minutes Posted Oct 6, 2026 at 10:00 am.
0:00
21:36
Download MP3
Show notes
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.
Support our show sponsors → ⁠https://freelancetofounder.com/sponsors⁠
Submit your own question → ⁠https://freelancetofounder.com/ask
Learn more about your ad choices. Visit megaphone.fm/adchoices