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Startups For the Rest of Us

Episode 787 | "We Shut Down a $1.5M Product, and Raised $10M Instead"

Startups For the Rest of Us

Rob Walling

Entrepreneurship, Management, Business, Marketing

4.9819 Ratings

🗓️ 12 August 2025

⏱️ 38 minutes

🧾️ Download transcript

Summary

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

Transcript

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0:00.0

You're listening to Start Up for the Rest of Us. I'm Rob Walling. In this episode, I have a conversation with Braden Dennis. He's come back on the show. He's the co-founder of Finchat, and they have recently rebranded to Fiscal.A. after raising a $10 million series A. I don't cover a lot of venture raises on this podcast because we focus on bootstrapped and

0:22.0

mostly bootstrapped companies. But now and again, in our ecosystem, we are seeing bootstrappers

0:27.4

who catch lightning in a bottle. And they realize that the opportunity that they've stumbled

0:34.2

upon has much more potential than they originally thought.

0:38.7

And some of those folks decide to sell early.

0:41.5

Some folks continue to bootstrap, and others decide to go that venture route.

0:46.2

And today, Brayden and I discuss that decision about why he and his co-founders decided to shoot for the moon.

0:53.0

As you can tell by the title, we also talk about how

0:55.0

they shut down a $1.5 million ARR product, and we do a quick recap of what got them here. You can hear

1:01.6

more of that in his prior episode, which I mentioned during the interview. Before we dive into that

1:08.0

conversation, I want to let you know about our microconf local chapters.

1:13.1

Building a business can be isolating, but it doesn't have to be.

1:16.1

So inside MicroConf Connect, which is our online membership community,

1:20.9

we are launching local chapters to help you meet each other in person.

1:25.0

Our first local chapters will be taking place in Barcelona, Toronto,

1:28.9

Sydney, Austin, and London, giving you the chance to share challenges, exchange ideas, and build

1:35.2

relationships with other founders in your area. Alongside these local chapters, we're also opening up

1:40.6

the MicroConf Ambassador program. If you want to help bring founders together in your

1:44.9

city, you can apply to become an ambassador. We'll provide everything you need, a comprehensive

1:49.3

playbook, promotional support, and swag to make your events successful. Because no event can be

1:54.7

successful without swag, am I right? If you're looking for accountability, collaboration, or just

1:59.4

good conversations over coffee, apply

...

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