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The Bootstrapped Founder - 412: The $0.20/Day AI System That Converts Trial Users Into Paying Customers
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412: The $0.20/Day AI System That Converts Trial Users Into Paying Customers

The Bootstrapped Founder

08/29/25

25m

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Transcript

Featured In

It took me a long while to realize this: AI isn't just something like a chatbot for my customers. AI can work behind the scenes to facilitate getting the right stuff in front of the right people for me, even just to figure out who people are and how I should talk to them. And today, I want to share exactly what I'm doing, how expensive this is to run, and how I believe this can be part of every single software as a service business out there—even if you don't have any touchpoint with artificial intelligence in that business at all. Even if you don't think you should be offering AI features to your customers.

This episode of The Bootstraped Founder is sponsored by Paddle.com — SaaS Happy Hour Series

The blog post: https://thebootstrappedfounder.com/the-0-20-day-ai-system-that-converts-trial-users-into-paying-customers/
The podcast episode: https://tbf.fm/episodes/the-0-20-day-ai-system-that-converts-trial-users-into-paying-customers

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

Previous Episode

undefined - 411: The Currents of a Founder
411: The Currents of a Founder

August 22, 2025

19m

I was reading Brandon Sanderson's latest novel, Wind and Truth, when I came across a sentence that stopped me cold: "A stronger current makes for stronger fish."

That's it. That's what entrepreneurship is.

We're constantly encountering currents that either facilitate what we want to accomplish—the businesses we want to build, the lives we want to create—or they oppose us, trying to sweep us into dangerous waters. These currents change all the time. They vary in strength depending on where you are in your journey. And here's the thing: they're mostly invisible until you learn to feel them.

Someone on Twitter asked me what my top three currents were after I shared this thought. It turned out to be a revealing exercise—assessing what I'm exposed to, what I'm dealing with, and how I'm navigating these forces. So let me share what I've discovered about the currents pulling at me as I build Podscan.

This episode of The Bootstraped Founder is sponsored by Paddle.comThe Web Revenue Lab Series

The blog post: https://thebootstrappedfounder.com/the-currents-of-a-founder/
The podcast episode: https://tbf.fm/episodes/411-the-currents-of-a-founder

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

Next Episode

You know that moment when you realize the ground has shifted beneath your feet? I had one of those moments recently. I was watching an AI agent build out a complex feature for Podscan in about twenty minutes – something that would have taken me days to code properly just a year ago. And it hit me: the rules of the game have fundamentally changed.

This episode of The Bootstraped Founder is sponsored by Paddle.com

The blog post: https://thebootstrappedfounder.com/were-gonna-need-a-bigger-moat/
The podcast episode: https://tbf.fm/episodes/413-we-re-gonna-need-a-bigger-moat

Check out Podscan, the Podcast database that transcribes every podcast episode out there minutes after it gets released: https://podscan.fm
Send me a voicemail on Podline: https://podline.fm/arvid

You'll find my weekly article on my blog: https://thebootstrappedfounder.com

Podcast: https://thebootstrappedfounder.com/podcast

Newsletter: https://thebootstrappedfounder.com/newsletter

My book Zero to Sold: https://zerotosold.com/

My book The Embedded Entrepreneur: https://embeddedentrepreneur.com/

My course Find Your Following: https://findyourfollowing.com

Here are a few tools I use. Using my affiliate links will support my work at no additional cost to you.
- Notion (which I use to organize, write, coordinate, and archive my podcast + newsletter): https://affiliate.notion.so/465mv1536drx
- Riverside.fm (that's what I recorded this episode with): https://riverside.fm/?via=arvid
- TweetHunter (for speedy scheduling and writing Tweets): http://tweethunter.io/?via=arvid
- HypeFury (for massive Twitter analytics and scheduling): https://hypefury.com/?via=arvid60
- AudioPen (for taking voice notes and getting amazing summaries): https://audiopen.ai/?aff=PXErZ
- Descript (for word-based video editing, subtitles, and clips): https://www.descript.com/?lmref=3cf39Q
- ConvertKit (for email lists, newsletters, even finding sponsors): https://convertkit.com?lmref=bN9CZw

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