The Bootstrapped Founder

Generative AI used to be for early adopters. But now, Apple is bringing it to every iPhone. What does this mean for indie founders?

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/ai-for-the-rest-of-us/

The podcast episode: https://tbf.fm/episodes/329-ai-for-the-rest-of-us

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

A few months ago, I raised a low 6-figure investment for Podscan. Here's the conversation between me and my investor, @tylertringas, that happened just before I signed the contract.

You usually don't get to listen in for one of those. Today, you will.

Tyler and I discuss how the Calm Company Fund navigates the alignment challenge between founders and investors, what makes a business like Podscan investable, and the risks of funding a portfolio of niche bootstrapped businesses.

Tyler on X: https://x.com/tylertringas

00:00:00 Bootstrapper-Compatible Funding
00:06:23 Profit Sharing and Standardizing Investment Agreements
00:12:53 Investor-Founder Alignment & Site Projects
00:22:30 Side Project Management in Investments
00:28:18 Early Stage Financing Investment Considerations
00:40:50 Valuation and Investment Strategy Art
00:48:19 Entrepreneurial Collaboration and Forward Planning

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/negotiating-bootstrapper-funding-with-tyler-tringas/ 

The podcast episode: https://tbf.fm/episodes/328-negotiating-bootstrapper-funding-with-tyler-tringas 

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

This week, I almost lost access to my database, including all its backups. Also, a full-text index brought down my product. Neither were intended —obviously—, but both made me revisit my safety precautions and how I approach depending on platforms like AWS. Here's what happened, how I got out of there, and what there is to prevent this in the future.

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/two-surprisingly-scary-tales-of-platform-risk/ 

The podcast episode: https://tbf.fm/episodes/327-two-surprisingly-scary-tales-of-platform-risk

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

Zeno Rocha (@zenorocha) went through YC to build Resend, yet he still acts and thinks like a bootstrapper. In a world of polarized opinions about venture funding and not raising money, Zeno is both "one of us" and "one of them" — for both sides!

Today, we talk about overcoming purism and embracing pragmatic entrepreneurship, starting with picking a niche Zeno truly understands: developers. We dive into how he's building an email platform that makes email fun again, what unexpected challenges a decade-old technology such as email can pose, and how to build a customer-centric business at scale.

Zeno is an indie hacker, and has always been. He embraces venture funding but without all the hype and unicorn-chasing. You'll learn a lot from someone walking the tightrope between worlds that usually collide. Enjoy a friendly conversation about email, extremes, and making your dreams come true.

Zeno on X: https://x.com/zenorocha

00:00:00 Building an Indie Email Company
00:08:48 Attention to Detail in Scaling
00:21:30 Finding the Right Funding Model
00:32:39 Building Developer Ecosystems and Partnerships

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/zeno-rocha-from-bootstrapping-to-ycombinator/

The podcast episode: https://tbf.fm/episodes/326-zeno-rocha-from-bootstrapping-to-ycombinator

The video: https://youtu.be/-V6D1lXyVQU

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

"Everyone and their mother are talking about AI. Every founder releases their 500th GPT wrapper."

"AI is all hype, no substance."

Or is it? What if our collective perspective is really skewed, and our gathering places are to blame? Here's my take on why indie hackers have a dangerously biased view on what AI businesses are and should look like.

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/indie-hackers-myopic-view-of-ai/

The podcast episode: https://tbf.fm/episodes/325-indie-hackers-myopic-view-of-ai

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

Tim Schumacher (@TimSchu), the mastermind behind SEDO and Adblock Plus, now leads the SaaS Group to new heights. With $60 million ARR, 20 thriving businesses, and 300 employees, Tim shares his incredible journey from a coder to an influential entrepreneur in scaling businesses.

From his strategic focus on developer and online marketing tools to his forward-thinking perspective on the role of AI in reshaping the industry, we dive deep into the bootstrapping mindset and how it empowers founders to build something extremely valuable that SaaS Group can keep running, growing, and creating life-changing exits at the same time.

Oh, and did you know that Tim almost bought my business?

Tim on Twitter: https://x.com/TimSchu

00:00:00 Private Equity and Business Growth Trends
00:12:34 Evaluating Niche Business Acquisitions
00:24:39 Acquisition and Growth Strategies in Business

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/tim-schumacher-the-bootstrappers-mindset/ 

The podcast episode: https://tbf.fm/episodes/324-tim-schumacher-the-bootstrappers-mindset

The video: https://youtu.be/16MQT8hU7wY

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

• (00:00) - Private Equity and Business Growth Trends

Today, you get a glimpse into an ongoing marketing experiment for Podscan.fm. What if I can frontload value for my future customers even before they sign up?

Here's why I chose to create a Dream Customer List and how it will help me jumpstart customer acquisition.

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/the-power-of-the-dream-customer-list 

The podcast episode: https://tbf.fm/episodes/323-the-power-of-the-dream-customer-list

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

Noah Kagan (@noahkagan) has made AppSumo a massive success — and he's spilling the beans on how to launch, build, and grow a successful software business. Noah likes to keep things weird, and our conversation is proof of that: from Taco T-shirts to failing at entrepreneurship, we walk through the ups and down of a wild and intriguing founder journey.

If you're looking for guidance that actually helps you find your footing, Noah's your man.

00:00:00 Lessons From Noah Kagan's Entrepreneurial Journey
00:12:54 Overcoming Fear of Asking for Help
00:17:56 Importance of Asking and Repeating Messaging
00:26:25 Business Development and Patience in Entrepreneurship
00:30:26 Entrepreneurial Insights on Book Launches
00:37:07 Building Relationships for Business Growth

Noah on Twitter: https://x.com/noahkagan

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/noah-kagan-early-stage-founder-hurdles-how-to-jump-them

The podcast episode: https://tbf.fm/episodes/322-noah-kagan-early-stage-founder-hurdles-how-to-jump-them

The video: https://youtu.be/MolxsU1csKc

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

It started as a normal day — but then things started going wrong. And my stress levels rose.

But I recently learned how to use that to my advantage. Here's how I wrangled with a SaaS founder's worst nightmare, what happened, and how I turned the tables.

 
This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/unexpected-downtime-stress-as-enhancement-vs-stress-as-panic

The podcast episode: https://tbf.fm/episodes/321-unexpected-downtime-stress-as-enhancement-vs-stress-as-panic

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

Dr. Jessica Gold (@blissscience) helps founders live an intentional and passionate life — which ultimately impacts their entrepreneurial success. She wants to put intentional self-care back on the map in a field obsessed with productivity and tracking metrics.

In our conversation, we dive deep into vulnerable places: from romance, passion, and love to dealing with stressful interpersonal conflicts. Dr. Jessica exposes the do-it-(for)-yourself frameworks that can help founders to stay level-headed when challenges seem insurmountable.

Dr. Jessica Gold on Twitter: https://twitter.com/blissscience

(00:00) Navigating Business and Personal Relationships
(12:28) Balancing Work and Pleasure in Founding
(18:04) Balancing Work and Pleasure for Success
(28:00) Importance of Body-Informed Therapy

This episode is sponsored by Acquire.com

The blog post: https://thebootstrappedfounder.com/dr-jessica-gold-emotional-resilience-and-self-care-for-founders/

The podcast episode: https://tbf.fm/episodes/320-dr-jessica-gold-emotional-resilience-and-self-care-for-founders

The video: https://youtu.be/-3MGGrldnIM

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