Episode 793 | TinySeed Tales s5e3: Building Momentum

Episode 793 | TinySeed Tales s5e3: Building Momentum

Author: Rob Walling September 4, 2025 Duration: 27:16
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

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 799 | TinySeed Tales s5e6: $500k ARR! [not-audio_url] [/not-audio_url]

Duration: 29:15
What's next for OutboundSync? In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here, from choosing not to…
Episode 797 | TinySeed Tales s5e5: Should I Raise More Funding? [not-audio_url] [/not-audio_url]

Duration: 30:25
OutboundSync just hit $35k MRR—but the decisions are only getting harder. In this episode of TinySeed Tales, Rob Walling and Harris Kenny dive into the messy middle of SaaS growth, where every opportunity comes with a tr…
Episode 795 | TinySeed Tales s5e4: The $20K Milestone [not-audio_url] [/not-audio_url]

Duration: 28:27
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…
Episode 794 | From Struggling Side Project to Life-Changing SaaS Exit [not-audio_url] [/not-audio_url]

Duration: 56:04
B2C, low price point, one-time payments… not the typical recipe for a life-changing exit. In this episode, Rob Walling talks with longtime listener Zamir Khan, founder of VidHug (now Memento). Zamir’s story broke a lot o…
Episode 791 | TinySeed Tales s5e2: Growing Pains [not-audio_url] [/not-audio_url]

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 ho…
Episode 789 | TinySeed Tales s5e1: From Agency to SaaS [not-audio_url] [/not-audio_url]

Duration: 30:55
Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between. In this season premiere, Rob…