
Harris Kenny
Founder of OutboundSync, a B2B SaaS company focused on outbound sales tooling; featured for sharing his journey growing the business past $500k ARR and lessons on bootstrapping and scaling.
Top 5 podcasts with Harris Kenny
Ranked by the Snipd community

40 snips
Sep 11, 2025 • 28min
Episode 795 | TinySeed Tales s5e4: The $20K Milestone
Harris Kenny, founder of OutboundSync, shares his journey to hitting $20k MRR ahead of schedule while participating in the TinySeed accelerator program. He discusses the exhilarating highs and lows of milestone achievements and the arrival fallacy that often follows success. Harris reveals strategic bets, like integrating with Salesforce and achieving SOC 2 compliance, which acted as game-changers for the business. He dives into the importance of consistent execution and hidden market demands, setting his sights on reaching $30k MRR next.

22 snips
Sep 25, 2025 • 29min
Episode 799 | TinySeed Tales s5e6: $500k ARR!
Harris Kenny, founder of OutboundSync, shares his journey past $500k ARR. He discusses the critical decisions behind his growth, including why he chose not to raise funding for now and how simplifying his tech stack improved efficiency. Instead of typical networking events, he opted for laser tag to create unique experiences. Harris emphasizes the importance of ambition, setting goals to double MRR, and the invaluable support from TinySeed. His advice for fellow founders? Stay persistent and keep redefining your path.

22 snips
Sep 18, 2025 • 30min
Episode 797 | TinySeed Tales s5e5: Should I Raise More Funding?
Harris Kenny, founder of Outbound Sync and expert in B2B SaaS, shares his journey of growing monthly recurring revenue to $35k. He discusses the pivotal decisions that accelerated this growth, such as strategic integrations and building trust through SOC 2 compliance. The conversation dives into the dilemmas of raising unnecessary funds, decluttering good ideas, and maintaining work-life balance amidst startup stress. Harris also highlights the importance of refining sales strategies and focusing on core business elements in today's AI-driven landscape.

22 snips
Jun 24, 2025 • 1h 31min
"Justin, I built a SaaS!"
Harris Kenny, founder of App On Sync, shares his inspiring journey from corporate life to creating his own SaaS product. He discusses the personal challenges of entrepreneurship, the critical role of user engagement, and the importance of community feedback in shaping his business. Harris reflects on the trials faced during his first attempts and highlights the value of excellent customer support in a competitive market. His insights on navigating the SaaS landscape provide a roadmap for aspiring entrepreneurs.

15 snips
Aug 28, 2025 • 29min
Episode 791 | TinySeed Tales s5e2: Growing Pains
Harris Kenny, founder of OutboundSync and former agency owner, shares his journey into the SaaS world. He reveals how niching down has driven sales momentum and discusses the challenges of hiring full-time staff. Harris highlights a game-changing Salesforce breakthrough and what it means for his product strategy. He also candidly addresses the importance of SOC 2 prep and the shift in mindset that led him to effectively utilize his TinySeed funding, reflecting on the evolving landscape of lead generation and agency support.