Welcome to Season 5 of TinySeed Tales, the documentary-style series where we follow one SaaS founder’s journey over 12 months to hear about the wins, the missteps, and everything in between.

In this season premiere, Rob Walling introduces Harris Kenny of OutboundSync. After running a successful agency, Harris makes the leap to go all-in on SaaS. It’s a high-stakes transition that many agency owners are never able to make.

Topics we cover:

(2:25) – From agency owner to TinySeed-backed SaaS
(6:38) – Walking away from consistent agency revenue to go all-in on SaaS
(13:51) – Going all-in vs. splitting focus
(16:13) – Why most agencies fail at SaaS
(28:15) – What’s working, what’s not, and what’s next

Links from the Show:

Join the TinySeed Mailing List - Applications reopen in September 2025
Apply for TinySeed
Coaching Call Bonus
MicroConf Connect
OutboundSync
The SaaS Playbook
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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