In this episode of TinySeed Tales, Rob Walling reconnects with Harris Kenny, founder of OutboundSync, to explore the rapid evolution of his SaaS business just months after transitioning from agency work.
Harris shares how niching down to outbound-focused agencies unlocked sales momentum. He talks about hiring, his Salesforce breakthrough, SOC 2 prep, and why finally spending his TinySeed funding changed everything.
Topics we cover:
(2:27) – Launching a lower-priced version and building expansion revenue
(6:40) – How lead-gen shops are outpacing legacy rev ops
(12:01) – Hiring full-time: Dev speed, onboarding load, and customer success firepower
(18:15) – A surprise Salesforce breakthrough and what it means for product strategy
(24:42) – SOC 2 prep, pricing confidence, and finally spending the TinySeed check
Links from the Show:
Join the TinySeed Mailing List
Apply for TinySeed - Applications reopen September 1, 2025
OutboundSync
Harris Kenny | LinkedIn
Coaching Call Bonus
Dynamite Jobs
Vanta
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
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Episode 790 | From Scrappy to Scalable: Evolving Your Role as a Founder
How can you scale yourself as a founder?
In this episode, Rob Walling is joined by Yaniv Bernstein (co-founder and CTO of Violet, former COO, VP of Engineering, and Google leader) to unpack how a founder’s role must change as the company grows. From writing the code yourself to leading managers of managers, they dig into the tough transitions every founder faces, and what happens if you don’t adapt.
Topics we cover:
(3:27) – How the founder/CEO role changes as your SaaS scales
(8:44) – The turning point where systems and processes matter
(14:49 – When to hand off marketing, sales, or product as a founder
(19:44) – Why setting context is your #1 job as a founder-CEO
(28:19) – Why hiring right (and firing fast) makes or breaks scaling
Links from the Show:
SaaS Institute
MicroConf | The community for SaaS founders
MicroConf YouTube Channel
People Engineering
The SaaS Playbook
Yaniv Bernstein | LinkedIn
Yaniv Bernstein (@ybernsteindig) | X
The Startup Podcast
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
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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
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Episode 788 | Do I Need a Co-founder? And More Listener Questions (with Derrick Reimer)
What are the real risks of AI-generated code and “vibe coding”?
In this episode, Rob Walling is joined once again by fan-favorite Derrick Reimer to answer a fresh batch of listener questions. They dig into solo vs. co-founder trade-offs, managing scope creep, and how integrations can shape early traction.
Want to get your questions answered? Drop them here.
Topics we cover:
(2:33) – Do you need a co-founder to succeed in SaaS?
(5:18) – The Risks of AI-Generated Code and “Vibe Coding”
(13:50) – How to manage scope creep as a solo founder
(23:32) – Finding and retaining great contractors
(39:43) – How to build a startup culture with a bias for action
Links from the Show:
MicroConf Europe | Istanbul, Sep 28-30, 2025
TinySeed Tales Podcast
MicroConf Connect
TinySeed Fund
SavvyCal
Derrick Reimer | LinkedIn
Derrick Reimer (@derrickreimer) | X
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
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Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"
How do you know it’s time to move on from a product that’s growing?
In this episode, Rob Walling chats with Braden Dennis, co-founder of Fiscal.ai (formerly FinChat), about a rare founder journey: bootstrapping, catching lightning in a bottle, and choosing to go big with venture capital. They dive into the emotional and strategic weight of shutting down a $1.5M ARR product, what shifts when you scale past 40 people, and why Braden prioritized long-term vision over short-term revenue.
Topics we cover:
(2:30) – From FinChat to Fiscal.ai: rebranding and repositioning
(6:50) – Why they raised a $10M Series A
(13:09) – From bootstrapped to venture-backed: what changes?
(19:56) – Becoming a real CEO at 25 employees
(26:44) – Why they shut down a $1.5M product
(30:30) – Lessons from having four co-founders
(33:13) – The benefits of joining TinySeed
Links from the Show:
MicroConf Connect
The Great CEO Within
TinySeed: SaaS Institute
Fiscal.ai (formerly FinChat)
Braden Dennis (@BradoCapital) | X
Braden Dennis | 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
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.
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