Episode 799 | TinySeed Tales s5e6: $500k ARR!
Update: 2025-09-25
Description
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 raise funding (for now), to planning a laser tag event no committee would approve, to what comes next on the road to $1M.
Topics we cover:
- (1:49 ) – Crossing $500k ARR and building personal health habits
- (5:36 ) – The big levers behind OutboundSync’s growth
- (6:39 ) – Laser tag, not hotel happy hours
- (13:01 ) – Deciding not to raise more funding (for now)
- (16:25 ) – An overbuilt tech stack
- (17:57 ) – Competitors, copycats, and growing a brand
- (19:06 ) – The next chapter for OutboundSync
- (23:29 ) – Ambition, TinySeed, and channeling energy
- (25:14 ) – Harris’s advice for founders still grinding
Links from the Show:
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!
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