Episode 793 | TinySeed Tales s5e3: Building Momentum

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9 • 819 Ratings

🗓️ 4 September 2025

⏱️ 27 minutes

🔗️ Recording | iTunes | RSS

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Summary

What happens when momentum hits and your biggest challenge becomes keeping up? In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus. Topics we cover: (1:40) – Closing his biggest deal ever and what it unlocked (4:26) – Learning how to do enterprise sales (6:20) – How SOC 2 made the product stronger (12:18) – New hires are paying off (18:23) – Building the Salesforce integration (22:13) – Getting pull from the market, not pushing (24:10) – Taking customers from unicorns Links from the Show: TinySeed SaaS Accelerator - Applications close on September 9th Coaching Call Bonus Invest in TinySeed YNAB (You Need A Budget) Dynamite Jobs 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	We're back with episode three of season five of Tiny Seed Tales.
0:04.9	I hope you're enjoying the season so far.
0:07.2	Before we dive into the episode, I wanted to let you know that Tiny Seed applications are open for our fall 2025 batch.
0:13.8	If you're a B2B SaaS founder with at least $1,000 of MRR, and you're looking for the perfect amount of funding, a community of ambitious,
0:21.1	like-minded founders, and a network of world-class mentors, you should apply. If you know your
0:25.9	metrics, the application only takes about 10 to 15 minutes to fill out. Applications close on
0:30.7	September 9th. Get all the details at tinyseed.com slash apply, and even if you miss the application deadline,
0:38.7	any of your email at tiny seed.com slash apply,
0:41.2	and you'll be notified next time we open applications.
0:43.9	Let's dive in.
0:45.1	I believe really firmly that we are ahead of the market.
0:47.9	I think that the users that we're signing up
0:49.8	and the prospects we're talking to today
0:51.3	represent like the very beginning of a big chunk
0:53.7	of a bell chunk of a bell
0:54.1	curve of the market that's going to be changing its process.
1:01.2	Welcome back to Tiny Seed Tales, a series where I follow a founder through the roller coaster
1:05.8	of building their startup. I'm your host Rob Walling, a serial entrepreneur and co-founder
1:10.4	of Tiny Seed,
1:11.7	the startup accelerator for ambitious SaaS bootstrappers. Here in season five, I've been
1:17.1	talking to Harris Kenny, founder of Outbound Sink. In our last episode, Harris moved on from a
1:23.2	broad market approach to zeroing in on agencies helping clients with cold outreach.
	...

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