Startups For the Rest of Us

Episode 799 | TinySeed Tales s5e6: $500k ARR!

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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: 
    • Invest in TinySeed Fund Three
    • Coaching Call Bonus
    • OutboundSync
    • Harris Kenny | LinkedIn

      • 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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      Startups For the Rest of UsBy Rob Walling
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