Startups For the Rest of Us Episode 795 | TinySeed Tales s5e4: The $20K Milestone
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Sep 11, 2025 Harris Kenny, founder of OutboundSync, shares his journey to hitting $20k MRR ahead of schedule while participating in the TinySeed accelerator program. He discusses the exhilarating highs and lows of milestone achievements and the arrival fallacy that often follows success. Harris reveals strategic bets, like integrating with Salesforce and achieving SOC 2 compliance, which acted as game-changers for the business. He dives into the importance of consistent execution and hidden market demands, setting his sights on reaching $30k MRR next.
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Hitting The $20K Milestone
- Harris hit $20K MRR ahead of schedule and felt both thrilled and overwhelmed.
- He planned to celebrate with his wife and then set a new $30K goal.
The Arrival Fallacy And Stress
- Harris experienced the arrival fallacy: milestone reached but anxiety persisted.
- Rob points out stress can both drive performance and become harmful if unchecked.
Repeat What Works To Reach $30K
- Keep executing the same core playbook: blocking and tackling wins the next milestone.
- Show up daily and repeat the actions that produced the current growth.