
Startup to Last Can Rick’s optimism defeat Tyler’s pessimism?
Dec 4, 2025
Dive into a lively discussion on AI's role in productivity, where optimism clashes with skepticism! Rick and Tyler share personal updates, including their creative hobbies and recent business milestones. They tackle the emotional impact of policy changes and the challenge of supporting team members effectively. The duo debates the merits of breaking projects into manageable tasks versus planning for the future. With thoughts on how AI can both assist in video production and reshape our understanding of work, this conversation is filled with intriguing insights!
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Episode notes
Early-Morning Reading Spree
- Tyler woke up at 4 a.m. and read for three hours because he couldn't sleep.
- Rick rediscovered fantasy reading and is re-reading The Wheel of Time after decades away.
Record Revenue During Chaotic Enrollment
- Tyler's company hit $25K MRR in November during a difficult open enrollment period.
- The policy subsidy changes made enrollments emotionally and operationally taxing for their agent JD.
Break Intertwined Projects Into Shippable Parts
- Break big intertwined projects into separable subprojects that handle shared dependencies first.
- Ship small, shippable pieces often to avoid long merges and slowdowns.







