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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