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

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9 • 819 Ratings

🗓️ 11 September 2025

⏱️ 28 minutes

🔗️ Recording | iTunes | RSS

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Summary

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! Subscribe & Review: iTunes | Spotify

Transcript

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0:00.0	Welcome back to a special Thursday episode of Startups for the Rest of us, where we continue on
0:04.4	with Tiny Seed Tales Season 5 as we follow Harris Kenny on his journey to grow Outbound Sink.
0:09.7	We've had a great response to these episodes from founders and Tiny Seed investors alike.
0:14.1	If you're interested in diversifying your portfolio and investing in ambitious, early-stage B2B SaaS
0:19.0	companies, we're currently raising Fund 3 for Tiny Seed.
0:22.6	We recently returned more than 100% of our first Tiny Seed Fund. And frankly, we're just getting
0:27.9	started. If you're interested in joining us, check out our thesis at Tinyseed.com slash invest.
0:34.5	And if you fill out the form there, it goes directly to my co-founder an R you can
0:38.7	also reach out to A-N-R directly at E-I-N-A-R at tiny seed.com let's dive in it is weird I do wonder like
0:46.5	oh is this the best idea I'm ever going to have maybe like I'm being hopefully not but like
0:49.9	maybe this could be like a really big thing I mean we're having calls now with like
0:53.8	pretty big companies and I do know we were having calls now with like pretty big companies.
0:55.8	And I do know that like there's like features in Trello that if I ship them right now,
0:59.7	I would turn them into revenue immediately.
1:04.1	Welcome back to Tiny Seed Tales, a series where I follow a founder through the roller coaster
1:08.2	of building their startup.
1:09.7	I'm your host, Rob Walling, a serial entrepreneur and co-founder of Tiny Seed, the startup accelerator
1:15.3	for ambitious SaaS bootstrappers.
1:18.8	Here in season five, I've been talking with Harris Kenny, founder of Outbound Sink.
1:23.4	Last time I spoke with Harris, he had just closed his biggest contract to date. Now, he's hit another impressive milestone.
1:31.7	Hey, Rob, quick clip for the pod.
1:34.4	20K. Let's fuck go.
	...

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