The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
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The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
Episode 795 | TinySeed Tales s5e4: The $20K Milestone
Startups For the Rest of Us
28 minutes 27 seconds
1 month ago
Episode 795 | TinySeed Tales s5e4: The $20K Milestone
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 Us
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
