5 “Boring” Decisions That Made Me a Multi-Millionaire

Rob Walling reflects on five pivotal decisions that helped him grow from a dreamer into the founder of multi-million dollar SaaS businesses.

1. Stop Consuming, Start Shipping

• Problem: Analysis paralysis — endless books, videos, and domains without progress.
• Decision: Start shipping products publicly.
• Impact: Builds confidence, reduces fear of criticism/failure, creates real opportunities.
• Evergreen lesson: No book or video guarantees success. Execution > learning.

2. Embrace Hard, Boring, Grind Work

• Problem: Only wanting to do “fun” tasks.
• Decision: Prioritize tasks by impact, not passion.
• Examples: SEO, customer support, bug fixes, copywriting, advertising.
• Impact: Built resilience and momentum. Freedom to choose work came only after years of grinding.
• Evergreen lesson: In the short term, you need progress, not passion.

3. Learn, Adjust, Don’t Repeat Mistakes

• Problem: Repeating the same failed approaches.
• Decision: Treat failures as feedback. Adjust course.
• Examples:
  • Avoided low-price B2C SaaS (high churn, low returns).
  • Shifted to B2B, higher pricing.
  • Combined building and acquiring apps.
• Evergreen lesson: Failure ≠ progress unless you learn and adapt.

4. Make Increasingly Larger but Manageably Sized Bets

• Problem: Growth requires capital, but risk must be contained.
• Decision: Reinvest steadily into progressively bigger bets.
• Path:
  • $11K → acquired NetInvoice → scaled revenue.
  • $30K → HitTail → grew further.
  • $200K → Drip → major SaaS success.
• Impact: Stepwise compounding of resources.
• Evergreen lesson: Bet bigger over time, but never bet the house.

5. Avoid Impulsive Decisions in Hard Times

• Problem: Burnout, criticism, money stress, frustration.
• Decision: Delay big decisions until emotions cool.
• Example: Declined a 7-figure acquisition offer for MicroConf during a low point → long-term win.
• Evergreen lesson: Don’t make permanent choices from temporary emotions.

Core Takeaways

• Execution beats endless preparation.
• Grind through unsexy work — that’s where traction is built.
• Adapt fast, don’t cling to failed strategies.
• Compound by escalating risk responsibly.
• Patience and emotional discipline prevent regret.

→ Evergreen advice: Turn off YouTube, pick something small, and ship it.