The Side Hustle Show The Ladders of Wealth Creation: A Step-by-Step System to Up Your Earning Power (Greatest Hits)
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Nov 17, 2025 
Nathan Barry, a serial entrepreneur and founder of ConvertKit, shares his journey from flipping burgers to generating $2.5M monthly in software revenue. He introduces his 'Ladders of Wealth Creation' framework, highlighting the pivotal four ladders that build skills for wealth. The conversation covers adding new income streams, project pricing strategies, and the importance of service-based businesses in professional growth. Barry discusses his focus on productization and shares marketing strategies that boosted ConvertKit's revenue, offering valuable insights for aspiring creators.
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Wealth Creation Is A Learnable Skill
- Wealth creation is a skill made of many smaller skills that compound over time.
- Treat business progress like learning an instrument: start with simple scales before tackling concertos.
Begin With Time-For-Money Roles
- Start with time-for-money roles to learn accountability and baseline work skills.
- Use that foundation before attempting higher-leverage business models.
Build Self-Accountability First
- If you freelanced full-time, provide your own accountability and systems.
- Learn focus rituals (Pomodoro, to-do lists) and habit tools before quitting a job.