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The Bootstrapped Founder - 421: Why You Should Never Start a Software Business
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421: Why You Should Never Start a Software Business

The Bootstrapped Founder

10/31/25

21m

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Featured In

The brutal truth about SaaS nobody tells you.

Here’s the thing: I’m about to share all the reasons why you should never, ever start a software business.

And yes, I’m fully aware that I’m talking to an audience of software founders. This is somewhat sarcastic, somewhat ironic twist on the great things about entrepreneurship. And the problems you'll face.

This episode of The Bootstraped Founder is sponsored by Paddle.com
You'll find the Black Friday Guide here: https://www.paddle.com/learn/grow-beyond-black-friday

The blog post: https://thebootstrappedfounder.com/why-you-should-never-start-a-software-business/
The podcast episode: https://tbf.fm/episodes/421-why-you-should-never-start-a-software-business

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

I know you're out there. The developer who watches their colleagues enthusiastically embrace Claude Code and Cursor, having AI write entire feature sets while you proudly type every semicolon by hand. The founder who sees AI-generated code as a ticking time bomb of bugs and security vulnerabilities. The software entrepreneur who believes that real code comes from human minds, not language models.

This one's for you.

This episode of The Bootstraped Founder is sponsored by Paddle.com
You'll find the Black Friday Guide here: https://www.paddle.com/learn/grow-beyond-black-friday

The blog post: https://thebootstrappedfounder.com/ai-for-the-code-writing-purist-how-to-use-ai-without-surrendering-your-keyboard/
The podcast episode: https://tbf.fm/episodes/420-ai-for-the-code-writing-purist-how-to-use-ai-without-surrendering-your-keyboard

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

When you build a software business as a founder, you have a dream. Building. Features. APIs. UIs.

But how much of that is JUST a dream, and what REALLY leads to paying customers?

This episode of The Bootstraped Founder is sponsored by Paddle.com
You'll find the Black Friday Guide here: https://www.paddle.com/learn/grow-beyond-black-friday

The blog post: https://thebootstrappedfounder.com/the-things-your-customers-dont-care-about/
The podcast episode: https://tbf.fm/episodes/422-the-things-your-customers-dont-care-about

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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