Episode 797 | TinySeed Tales s5e5: Should I Raise More Funding?
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode of Tiny Seed Tales, we follow Harris Kenny as he reaches a pivotal milestone - hitting $35,000 in monthly recurring revenue (MRR) and achieving infinite runway for his SaaS company, Outbound Sync. (02:00) Harris has grown from $20,000 to $35,000 MRR in just three months, representing 75% growth, by focusing on two key strategies: adding integrations for other platforms like Instantly and continuing to improve Salesforce features. (03:12) Now at breakeven, Harris faces a new challenge - deciding whether to raise additional funding to accelerate growth or continue bootstrapping. (13:39) He's also invested in a sales coach to improve his founder-led sales process, which has contributed significantly to his recent growth momentum. (25:41)
- Main Theme: Harris Kenny reaches profitability with Outbound Sync while navigating the complex decision of whether to raise additional funding to capitalize on significant growth opportunities in the AI-driven data integration space.
Speakers
Rob Walling
Rob Walling is a serial entrepreneur and co-founder of TinySeed, the startup accelerator for ambitious SaaS bootstrappers. He hosts the popular Startups For The Rest of Us podcast and has extensive experience building and scaling software companies over more than two decades in the startup ecosystem.
Harris Kenny
Harris Kenny is the founder of Outbound Sync, a data integration tool that helps growth agencies and sales teams sync data between various sales tools like CRMs, email platforms, and prospecting tools. He previously ran a HubSpot agency for three and a half years before transitioning to focus full-time on his SaaS product, which he joined TinySeed's Spring 2024 batch.
Key Takeaways
Focus Relentlessly on Value Creation for Customers
Harris attributes his success to maintaining a laser focus on whether each feature or decision will help customers book more meetings and close more deals. (10:40) He constantly evaluates decisions through the lens of customer results, asking "Will this help people book more meetings and deals?" This north star approach has guided him through countless product and business decisions, from building specific Salesforce features to handling data inconsistencies from upstream providers. By staying accountable to customer outcomes rather than getting distracted by internal metrics or competitor features, Harris has maintained consistent 10-20% month-over-month growth throughout his journey.
Strategic Saying No Is Critical for Bootstrapped Growth
As a bootstrapper with limited resources, Harris emphasizes the importance of constantly saying no to opportunities, features, and integrations that don't align with core business priorities. (08:11) He describes feeling like he's "constantly saying no to things" both professionally and personally as a parent of young children building a startup. This disciplined approach to resource allocation has enabled him to focus on the highest-impact activities - specifically partner relationships with growth agencies and core platform integrations - that drive the most revenue growth.
Invest in Key Hires Early to Scale Founder Bandwidth
Harris credits two critical hires - bringing his developer on full-time and hiring a Customer Success Manager - as game-changing decisions that freed up significant mental space for strategic work. (12:00) The CSM hire in particular allowed Harris to focus on growth and product decisions rather than getting bogged down in customer support issues. This investment in people, even when cash was tight, created leverage that directly contributed to his ability to scale from $20K to $35K MRR in just three months.
SOC 2 Compliance Unlocks Enterprise Revenue
Implementing SOC 2 compliance has been a complete game-changer for Harris's business, enabling him to cruise through security reviews and close larger enterprise deals. (04:52) Beyond just meeting compliance requirements, the SOC 2 process made Outbound Sync a better product by implementing practices that help catch bugs and improve overall quality. For non-technical founders like Harris, SOC 2 covered important blind spots and established professional processes that elevated the entire operation. The investment in a quality trust center and auditor has created a competitive advantage in enterprise sales cycles.
Double Down on Working Growth Channels
Rather than trying to fix underperforming channels, Harris's sales coach helped him realize he should focus more resources on what's already working - specifically agency partnerships. (27:24) Growth agencies using tools like Clay, Smart Lead, and Instantly have become Outbound Sync's most successful partner channel, far outperforming traditional CRM partner shops. This insight led Harris to stop trying to lift up direct deals and instead invest more heavily in the agency channel that was already generating consistent results, contributing significantly to his recent growth acceleration.
Statistics & Facts
- Harris grew from $20,000 to $35,000 MRR in just three months, representing 75% growth and nearly doubling his monthly recurring revenue. (02:56)
- Outbound Sync has maintained consistent 10-20% month-over-month growth on average since their first revenue month in October 2023, with some months exceeding 50% growth. (10:10)
- Harris joined TinySeed's Spring 2024 batch in May with a goal of reaching profitability within one year (June 2025), and achieved this milestone ahead of schedule. (06:24)
