Startups For the Rest of Us Episode 799 | TinySeed Tales s5e6: $500k ARR!
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Sep 25, 2025 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.
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Vacation Sparked Health Changes
- Harris took a family trip to Europe which wasn't restful but provided space to think and start new personal routines.
- He began waking at 4:30am and built an 81-day workout streak that improved his health and energy.
Big Levers Beat Tiny Tweaks
- Harris attributes growth to getting a few big directional things right rather than optimizing tiny details.
- He intentionally let small tasks slide to focus on high-leverage work that moved the company forward.
Laser Tag Instead Of A Boring Happy Hour
- Harris planned an invite-only laser tag event around a major industry conference to create buzz and deepen relationships.
- The event grew into a 90-person gathering with sponsors, buses, trophies, and professional media coverage.