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Startups For the Rest of Us

Episode 789 | TinySeed Tales s5e1: From Agency to SaaS

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9819 Ratings

🗓️ 21 August 2025

⏱️ 31 minutes

🧾️ Download transcript

Summary

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

Transcript

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0:00.0

Is this really an episode of startups for the rest of us on a Thursday?

0:03.9

That's right.

0:04.9

For the next six weeks, you'll find new episodes of Tiny Seed Tales, Season 5, in this feed every Thursday morning.

0:12.1

If you're not familiar with Tiny Seed Tales, it's a narrative-style, season-based show,

0:16.9

where I follow a founder as they navigate the ups and downs of building a SaaS.

0:21.3

We dive into their journey to find product market fit, optimize the product, scale their business, and hopefully reach escape velocity.

0:28.4

These episodes were recorded over the past year, so you're going to get an inside look at a founder's journey.

0:34.7

The goal is to give you honest insights into the challenges, setbacks, and hard-won

0:39.1

victories that come with growing a real SaaS company. If you're new to Tiny Seed, it's the

0:43.7

startup accelerator I run for ambitious, bootstrapped SaaS founders. And it's the first accelerator

0:48.9

of its kind. Twice a year, we fund B2B SaaS founders who want just the right amount of capital,

0:54.3

a community of like-minded, ambitious founders, and access to mentorship, advice,

0:58.6

and everything else you'd expect from a world-class accelerator.

1:02.3

Applications for our fall 2025 batch open on September 1st.

1:06.6

This time around, we've shortened the application window a bit, and we've tightened up the process,

1:14.8

so we'll get you a definitive answer much quicker, avoiding the drawn-out uncertainty common in other investment processes.

1:18.1

The application is intentionally short and focused, and if you know your core metrics,

1:22.6

it usually takes about 10 to 15 minutes to complete.

1:25.0

For all the details, and to get notified when applications open, go to tiniseed.com slash apply

1:30.9

and get on our mailing list.

1:32.7

Let's dive into this first episode of Season 5.

1:35.7

My name is Harris Kenny.

...

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