Side Hustle School Ep. 3248 - Q&A: “Should I spend $2,000 on retention or acquisition?”
Nov 22, 2025
Santiago, a bootstrapped software founder from Miami, grapples with a $2,000 dilemma for his subscription app with 180 users. Should he spend it on retention strategies to reduce cancellations or chase new sign-ups? Chris advises prioritizing the churn rate first, highlighting the importance of fixing leaks before investing. If churn is low, acquisition could be the way to grow revenue. The discussion emphasizes focusing on existing customers while keeping an eye on scaling when metrics are favorable.
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Santiago’s Real-World Dilemma
- Santiago calls from Miami with a bootstrapped SaaS of 180 users at $15/month and $2,000 to reinvest.
- He asks whether to focus on retention (lifetime value) or acquisition (lowering acquisition costs).
Measure Churn Before Spending
- Do check your churn rate before choosing between retention or acquisition spending.
- If churn is low, prioritize acquisition to grow revenue; if churn is high, fix leaks first.
Small Base, Big Potential
- A small subscription base at a low price can still be a solid foundation for growth.
- Moving from a few thousand to $5k–$10k monthly changes strategic options significantly.