DiscoverStartups For the Rest of UsEpisode 795 | TinySeed Tales s5e4: The $20K Milestone
Episode 795 | TinySeed Tales s5e4: The $20K Milestone

Episode 795 | TinySeed Tales s5e4: The $20K Milestone

Update: 2025-09-11
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Harris hit $20k MRR. It’s real. What’s next?





In this episode of TinySeed Tales, Rob Walling celebrates with Harris Kenny after OutboundSync crosses $20k MRR ahead of schedule. They talk about why hitting a milestone can feel both exciting and overwhelming, the arrival fallacy, and how simple, consistent execution may be all it takes to reach $30k. Harris shares the bets that moved the needle, including Salesforce, SOC 2, and what hidden demand taught him about building integrations before anyone asked.





Topics we cover: 






  • (1:32 ) – Crossing $20k MRR and aiming for $30k




  • (6:29 ) – The Salesforce bet




  • (8:17 ) – Runway, burn, and pricing upmarket




  • (10:34 ) – Raise capital or keep bootstrapping




  • (15:03 ) – SOC 2 as a sales unlock




  • (20:11 ) – Marketplace credibility and AppExchange




  • (22:05 ) – Hidden demand for Salesforce




  • (26:11 ) – The push to $30k and parity





Links from the Show: 









If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!





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Episode 795 | TinySeed Tales s5e4: The $20K Milestone

Episode 795 | TinySeed Tales s5e4: The $20K Milestone

Rob Walling