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.

• (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

• 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!

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Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter?

In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal.

This episode is brought to you by Gearheart.io, which specializes in helping early-stage founders validate ideas, prototype SaaS products, and build AI-powered MVPs with real user testing, so your code won’t crumble when your first customers show up.

Founded by entrepreneurs who’ve launched and exited their own startups, Gearheart has helped launch over 70 B2B SaaS products, including SmartSuite (which raised $38 million). They get where you’re at.

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• (3:12) – TinySeed returns Fund One
• (9:40) – GPT-5: Upgrade or letdown?
• (19:19) – Are we in an AI bubble?
• (24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees
• (31:06) – The bigger problem: Are startups forgetting to share the upside?
• (40:05) – Lifestyle vs. Ambitious Bootstrapping

• TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd
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• MicroConf
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• Discretion Capital
• Einar Vollset | LinkedIn
• Einar Vollset (@einarvollset) | X
• Tracy Osborn
• Tracy Osborn | LinkedIn
• Tracy Osborn (@tracymakes) | X

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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In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work.

Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.

• (2:27) – Launching a lower-priced version and building expansion revenue
• (6:40) – How lead-gen shops are outpacing legacy rev ops
• (12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
• (18:15) – A surprise Salesforce breakthrough and what it means for product strategy
• (24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check

• Join the TinySeed Mailing List
• Apply for TinySeed - Applications reopen September 1, 2025
• OutboundSync
• Harris Kenny | LinkedIn
• Coaching Call Bonus
• Dynamite Jobs
• Vanta

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