Episode 795 | TinySeed Tales s5e4: The $20K Milestone
Update: 2025-09-11
Description
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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