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Startups For the Rest of Us

Episode 799 | TinySeed Tales s5e6: $500k ARR!

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9819 Ratings

🗓️ 25 September 2025

⏱️ 29 minutes

🧾️ Download transcript

Summary

What's next for OutboundSync? In the Season 5 finale of TinySeed Tales, Rob Walling talks with Harris Kenny as OutboundSync blows past $500k ARR. Harris shares the wins and struggles of getting here, from choosing not to raise funding (for now), to planning a laser tag event no committee would approve, to what comes next on the road to $1M. Topics we cover:  (1:49) – Crossing $500k ARR and building personal health habits (5:36) – The big levers behind OutboundSync’s growth (6:39) – Laser tag, not hotel happy hours (13:01) – Deciding not to raise more funding (for now) (16:25) – An overbuilt tech stack  (17:57) – Competitors, copycats, and growing a brand (19:06) – The next chapter for OutboundSync (23:29) – Ambition, TinySeed, and channeling energy (25:14) – Harris’s advice for founders still grinding Links from the Show:  Invest in TinySeed Fund Three Coaching Call Bonus 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

Transcript

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0:00.0

It's the sixth and final episode of Tiny Seed Tales Season 5, where we've followed Harris

0:06.0

Kenny's journey as he's had incredible results growing outbound sync. If you're interested in

0:12.9

investing in founders like Harris and diversifying your portfolio away from public markets

0:19.4

or wherever you might have that money parked, you can

0:22.2

join Tiny Seed Fund 3 to invest in early stage bootstrapped B2B SaaS companies.

0:28.5

To learn more about our thesis, you can add to tinyseed.com slash invest.

0:33.1

And if you fill out the form on that page, it goes directly to ANR, my co-founder's inbox. If you want to keep up with everything we're doing at Tiny Seed, head to Tinyseed.com and drop your email in the footer. I promise we will not spam you. We only send occasional updates about what's going on in the world of ambitious, mostly bootstrap founders. Let's dive into the sixth and final episode of this season.

0:55.0

There's a light at the end of the tunnel, which I haven't felt for a long time. If anything,

0:58.4

it felt like the light was getting like dimmer. Like I was like on like a little like train thing,

1:01.7

but the train was like on a hill and it was like rolling backwards. So now I found the hand crank

1:06.2

and I'm like kind of like cranking towards the light.

1:12.6

Welcome back to Tiny Seat Tales.

1:14.6

This is the final episode of season five,

1:16.8

and we're following Harris Kenny's journey

1:18.7

from agency owner to SaaS founder.

1:20.9

When we started this series,

1:22.3

Harris was juggling his agency

1:23.6

while building outbound sync.

1:25.3

Over five episodes, we've watched him go all in, navigate

1:28.7

the ups and downs of early growth, achieve profitability, and face the tough decisions that come

1:33.8

with success. In our last episode, he was about to take off on a vacation where he was planning

1:39.1

to mull over the decision on whether or not he should raise an additional round. So I wanted to check up on him to see how it went.

...

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