Episode 791 | TinySeed Tales s5e2: Growing Pains

Episode 791 | TinySeed Tales s5e2: Growing Pains

Author: Rob Walling August 28, 2025 Duration: 29:16
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. Topics we cover:  (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 Links from the Show:  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

Rob Walling hosts Startups For the Rest of Us, a long-running conversation focused squarely on the realities of building a company without massive venture funding. This isn't about Silicon Valley fairy tales; it's a practical, ground-level view of entrepreneurship. Each episode delves into the specific journeys of founders who are starting, acquiring, or growing their SaaS businesses, emphasizing the path of bootstrapping. You'll hear the unvarnished details-the strategic decisions, the unexpected obstacles, and the hard-won victories that define the daily life of a founder. The discussions are built on real stories, offering tangible lessons from both struggle and success. For anyone who has ever felt that the typical startup narrative doesn't reflect their own resource-constrained reality, this podcast provides a necessary and relatable perspective. It’s a deep resource for actionable advice and genuine camaraderie, connecting you with the experiences of those navigating the same challenging terrain. Tune in for honest conversations that cut through the hype and focus on building sustainable businesses.
Author: Language: en-us Episodes: 100

Startups For the Rest of Us
Podcast Episodes
Episode 734 | The 20 Year Bootstrapper (With Ian Landsman) [not-audio_url] [/not-audio_url]

Duration: 35:03
In episode 734, Rob Walling interviews Ian Landsman, founder of HelpSpot, about his 20-year bootstrapper journey. They discuss Ian's transition from on-prem software to SaaS, the challenges and benefits of each, and the…
Episode 732 | Lessons Learned Bootstrapping to a $615M Exit [not-audio_url] [/not-audio_url]

Duration: 36:25
In episode 732, Rob Walling interviews Jeff, a mostly anonymous and retired founder, about his mostly bootstrapped business and subsequent exits. Jeff shares how he started the company in 2003 and how he persevered in th…

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