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Episode 135 · September 30, 2026

Justin Jacobs

From the Trunk of a Car

Founder, Health Plan Markets · Author, Journey to the Summit · Host, Closed!

About this conversation

Justin Jacobs got his insurance license in 2005 after a friend showed him a paycheck, and started Health Plan Markets in 2013 out of the trunk of his car. He had the company set up for eight months before he left his job, and he didn't leave by choice: "The universe made the decision for me. They fired me." Today HPM supports more than 700 agents in 41 states. In this hour he talks about the kitchen tables that hooked him on the work, the iceberg nobody sees under a success, the agent he bet against who became a top producer, and his field journal for agents, Journey to the Summit. He also explains why he now runs his marriage on the same system he uses to run the company.

In this conversation

  1. 00:00The trunk of a car, and the paycheck that got him licensed
  2. 05:06Crying at the kitchen table: why he believes in this work
  3. 08:24The iceberg, and the 90 percent nobody sees
  4. 15:32Marketing for doctors, coasting, and a boss named Gus
  5. 21:41"The universe made the decision for me. They fired me."
  6. 25:54Brenda Powell, the agent he bet against
  7. 28:59The first hundred agents, and his book, Journey to the Summit
  8. 38:12He runs his marriage like his company
  9. 42:29Serving those who serve others, and a $150,000 heart surgery
  10. 50:36Night diving in Key Largo, and the Orlando nobody sees

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