The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
All content for Startups For the Rest of Us is the property of Rob Walling and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
Episode 789 | TinySeed Tales s5e1: From Agency to SaaS
Startups For the Rest of Us
30 minutes 55 seconds
2 months ago
Episode 789 | TinySeed Tales s5e1: From Agency to SaaS
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!
Subscribe & Review: iTunes | Spotify
Startups For the Rest of Us
The original podcast for bootstrapped and mostly bootstrapped startups, this show follow the stories of founders as they start, acquire, and grow SaaS companies. Hear when they fail, struggle, succeed, and take you with them through the tumultuous life of a SaaS founder. If you like Mixergy, This Week in Startups, or SaaStr, you’ll enjoy Startup for the Rest of Us.
