Justin Simon is a content strategist, course creator, and founder of the Distribution First Academy, helping solopreneurs and marketers build smarter content engines without burning out.
In this episode, Justin shares how a layoff became the unexpected push he needed to bet on himself—and why he’s focused on building a business he never wants to retire from. He opens up about navigating the messy early days of consulting, finding his niche in content repurposing, and the mindset shifts that helped him build a more sustainable, intentional career. From launching a course while still working full-time to taking a leap into coaching and community building, Justin traces the real, unfiltered path that brought him to today—and where he’s aiming next.
(00:00) Intro
(01:28) Creating the Content Repurposing Roadmap
(02:52) Transition to solopreneurship
(11:54) Early struggles and learning curves
(19:22) Lessons from fractional roles
(22:49) Balancing revenue streams
(23:16) Building a membership community
(26:25) The challenges of creating a membership
(32:33) The impact of one-on-one coaching
(37:58) Balancing personal and professional life
(47:23) What Justin would’ve done differently
Follow Justin on LinkedIn: https://www.linkedin.com/in/justincsimon/
Check out Distribution First Academy: https://distributionfirst.club/
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