Startups For the Rest of Us

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

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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: 
    • Invest in TinySeed Fund 3
    • Coaching Call Bonus
    • MicroConf Events
    • OutboundSync
    • Harris Kenny | LinkedIn

      • 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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      Startups For the Rest of UsBy Rob Walling
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