The Bootstrapped Founder

Connor Turland (@Entrecurious) is the prototypical software entrepreneur. He found a niche from a "prior life" and is now building an AI bookkeeping SaaS.

Now, many founders struggle with bookkeeping, so this is your opportunity to learn more about the pitfalls and opportunities of that field from someone who speaks both "developer" and "bookkeeper."

Here's Connor and how he is employing cutting-edge AI in an industry that is usually very resistant to change.

Learn more about Connor at https://connorturland.com/
You'll find Ceedar at https://ceedar.ai/

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/connor-turland-pioneering-the-future-of-bookkeeping-with-ceedar-ai/

The podcast episode: https://tbf.fm/episodes/359-connor-turland

Check out Podscan to get alerts when you're mentioned on podcasts: 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

AI was supposed to do our chores while we write prose and compose symphonies. Why is it composing our music and writing our books now, while WE do the chores?

As software founders, we have a special responsibility — after all, we're the ones crafting a new reality of AI empowerment. But here's the thing: an AI does not love its work. It can't.

And that's a problem. Today, I'll dive into how we can solve this.

Oh, and before you get into it: Podscan is running a 30%-off Black Friday Deal — use "BLACKFRIDAY" during checkout for a full year of discount on any plan.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/love-is-for-those-who-love-the-work/

The podcast episode: https://tbf.fm/episodes/358-love-is-for-those-who-love-the-work

Check out Podscan to get alerts when you're mentioned on podcasts: 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

Today, I’ll dive into the difference between a trial user and a trial abuser and what you can do to invite the former and prevent the latter.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/free-trial-error/

The podcast episode: https://tbf.fm/episodes/357-free-trial-error

Check out Podscan to get alerts when you're mentioned on podcasts: 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

Coding with AI changes everything. It changes how we design, test, and improve our software projects. Today, I’m talking to generative AI expert James Phoenix.

He’s written the book on prompt engineering and shares his hard-earned AI insights freely on the show — including a crash course in developing effectively with the Cursor IDE.

Are developers just AI wranglers now? Technical managers? Will we ever code again?

You’ll find out today.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/james-phoenix-mastering-code-ai-for-the-modern-developer/

The podcast episode: https://tbf.fm/episodes/356-james-phoenix-mastering-code-ai-for-the-modern-developer

Check out Podscan to get alerts when you're mentioned on podcasts: 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

YouTube is both the best and the worst source of information — because we can watch it all, but no one will tell us what's REALLY worth watching.

Here's how the gatekeepers have vanished, and what has taken their place.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/the-age-of-the-gatekeeper-is-over/

The podcast episode: https://tbf.fm/episodes/355-the-age-of-the-gatekeeper-is-over

Check out Podscan to get alerts when you're mentioned on podcasts: 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

The problem with having no boss is that there's no one to stop you from procrastinating.

I'm challenged by this daily, and I have found a few ways to stay accountable. I'll share those with you today.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/the-art-of-productive-procrastination/

The podcast episode: https://tbf.fm/episodes/354-the-art-of-productive-procrastination

Check out Podscan to get alerts when you're mentioned on podcasts: 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

I want new prospects to receive the maximum possible value the moment they register for Podscan, so I treat them as customers before they even come to the page for the very first time.

Here's the Podscan Dream Customer strategy — from idea to execution.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/podscans-dream-customer-acquisition-strategy/

The podcast episode: https://tbf.fm/episodes/353-podscan-s-dream-customer-acquisition-strategy

Check out Podscan to get alerts when you're mentioned on podcasts: 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

Yesterday, I shrunk the size of my production database from four terabytes to just under one terabyte.

Something interesting happened last weekend that made me realize I needed to change how I think about scale.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/running-lean-at-scale/

The podcast episode: https://tbf.fm/episodes/352-running-lean-at-scale

Check out Podscan to get alerts when you're mentioned on podcasts: 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

When a Podscan user got a bit "too general" with their keywords, all of a sudden, my email provider stopped sending emails.

Whoops.

Let's talk user error and founder foresight.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/from-overload-to-opportunity/

The podcast episode: https://tbf.fm/episodes/351-from-overload-to-opportunity

Check out Podscan to get alerts when you're mentioned on podcasts: 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

SaaS founders are simultaneously tenants and landlords, renting the tools we need while offering our own services for subscription. It's a world where true ownership seems increasingly elusive, yet understanding its nature is crucial for building lasting value.

This episode is sponsored by Paddle.com — if you're looking for a payment platform that works for you so you can focus on what matters, check them out.

The blog post: https://thebootstrappedfounder.com/building-your-castle-in-someone-elses-kingdom/

The podcast episode: https://tbf.fm/episodes/350-building-your-castle-in-someone-elses-kingdom

Check out Podscan to get alerts when you're mentioned on podcasts: 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