Episode 793 | TinySeed Tales s5e3: Building Momentum
What happens when momentum hits and your biggest challenge becomes keeping up?
In this episode of TinySeed Tales, Rob Walling catches up with Harris Kenny, founder of OutboundSync. Revenue is growing, the team is moving fast, and enterprise leads are coming in. But with success comes complexity: support load, pricing strategy, and product demands are all increasing. Harris is hiring again, learning to say no, and figuring out how to keep the momentum without losing focus.
Topics we cover:
(1:40) – Closing his biggest deal ever and what it unlocked
(4:26) – Learning how to do enterprise sales
(6:20) – How SOC 2 made the product stronger
(12:18) – New hires are paying off
(18:23) – Building the Salesforce integration
(22:13) – Getting pull from the market, not pushing
(24:10) – Taking customers from unicorns
Links from the Show:
TinySeed SaaS Accelerator - Applications close on September 9th
Coaching Call Bonus
Invest in TinySeed
YNAB (You Need A Budget)
Dynamite Jobs
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!
Subscribe & Review: iTunes | Spotify
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Episode 792 | Hot Take Tuesday: GPT-5 Struggles, the A.I. Bubble, and the Windsurf Debacle
Is GPT-5 a real risk for SaaS founders, or just the beginning of a new chapter?
In this Hot Take Tuesday, Rob Walling, Einar Vollset, and Tracy Osborn dig into GPT-5’s mixed reviews, signs of stress in the A.I. bubble, and how Windsurf’s $2.4B exit left early employees with nothing. They also unpack why returning a VC fund is such a rare (and big) deal.
Episode Sponsor
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Topics we cover:
(3:12) – TinySeed returns Fund One
(9:40) – GPT-5: Upgrade or letdown?
(19:19) – Are we in an AI bubble?
(24:09) – The Windsurf debacle: $2.4B exit, $0 for early employees
(31:06) – The bigger problem: Are startups forgetting to share the upside?
(40:05) – Lifestyle vs. Ambitious Bootstrapping
Links from the Show:
TinySeed Fall 2025 Applications Live Q&A - Join us Wednesday September 3rd
TinySeed SaaS Accelerator - Applications are Open!
Invest in TinySeed
MicroConf
SaaS Institute
Discretion Capital
Einar Vollset | LinkedIn
Einar Vollset (@einarvollset) | X
Tracy Osborn
Tracy Osborn | LinkedIn
Tracy Osborn (@tracymakes) | 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 791 | TinySeed Tales s5e2: Growing Pains
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
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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