Strategic Risks and Integration Success

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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