I speak about how I’m automating my indie founder workflow using N8N. I share my favorite automations: press release creation and translations, social media scheduling, and newsletter writing, all powered by AI and connected through tools like Excel and GPT. I talk about handling integrations, using Flarecut for YouTube Shorts, and the challenges with Reddit. I discuss my plans to automate B2B outreach and customer success. My focus is on maximizing distribution, saving time, and scaling my projects with automation.

Twitter: https://x.com/wbetiago

Timestamps by PodSqueeze

Introduction and Podcast Setup (00:00:01)  

Discovering and Setting Up N8N (00:01:21)  

Overview of N8N Features (00:02:35)  

Need for Automation in Workflow (00:04:46)  

Automating Press Releases (00:05:54)  

Technical Setup: MCP Server Integration (00:07:04)  

Automated Social Media Posting (00:09:19)  

Challenges with Social Media Integrations (00:12:28)  

Automating Newsletters (00:13:31)  

Reddit Automation Attempts and Issues (00:15:20)  

Future Automation Plans (00:17:34)  

Reflections and Closing Thoughts (00:18:33)  

Outro and Call to Action (00:19:36)

My experience attending a business conference in Madrid as a bootstrapped founder. I talk about the challenges I faced pitching in Spanish, the costs involved in attending the conference, and why face-to-face meetings are so important for B2B sales. I share my own tips on networking, negotiating ticket prices, and preparing demos, and I also describe what it was like staying in a capsule hotel. I emphasize the irreplaceable value of in-person connections and engaging on social media, and I reflect on what it means to expand into new markets. I’d love to hear about your own conference experiences, so feel free to share them with me!

I speak about the challenges of setting prices for B2C and B2B customers. I share why B2C is more price-sensitive and talk about Podsqueeze’s shift to bigger B2B clients. I give examples from other SaaS companies—how some only show enterprise pricing and others adjust based on value or usage. I talk about Podsqueeze’s new pricing strategy for enterprise clients and my lessons from past mistakes. If you want to connect or have questions, reach out on Twitter or LinkedIn.

Twitter: https://x.com/wbetiago

Linkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/

Timestamps por PodSqueeze

Introduction and Episode Overview (00:00:01)  

Podsqueeze’s B2C Beginnings (00:01:35)  

Transition to B2B and Hitting a Growth Plateau (00:03:07)  

First B2B Sales Meetings and Pricing Challenges (00:06:21)  

The Challenge of Serving Both B2C and B2B (00:07:53)  

Example 1: Get Vocals’ B2B-Only Flexible Pricing (00:09:20)  

Example 2: Turnkey’s Value-Based Pricing (00:12:04)  

Example 3: SendGrid’s Usage-Based Tiered Pricing (00:14:41)  

Podsqueeze’s Pricing Adjustments and Negotiation Issues (00:17:18)  

Future Plans: Unlimited Enterprise Plan and Flexibility (00:18:26)  

Conference Preparation and Closing Remarks (00:20:42)

I reflect on my recent interview with Craig Hewitt, founder of Castos. I dive into the trade-offs between bootstrapping and raising venture capital. I share my thoughts on how AI is changing entrepreneurship and jobs. I talk about my own experiences with product pivots and tough market challenges. I explain how I use AI to boost efficiency in my startup journey. Building products is easier than ever, but getting distribution right is still the hardest part.

Twitter: https://x.com/wbetiago

Linkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/

Timestamps by Podsqueeze

Introduction and Recap of Previous Episode (00:00:02)

Raising Funds vs. Bootstrapping (00:01:20)

Valuation, Market Size, and Risks of Raising (00:03:59)

Analyzing Competitors and Market Potential (00:09:13)

Calculating Market Size and Revenue Projections (00:10:21)

How Much to Raise and Lessons from Greg Hewett (00:11:32)

Benefits of Not Raising and Work-Life Balance (00:12:54)

AI’s Impact on Productivity and Hiring (00:12:54)

Long-Term Thinking and Consistency (00:13:59)

AI’s Negative Impact on Jobs and the Economy (00:16:25)

Building Resilient Businesses and Diversification (00:18:58)

Turning a Landing Page into a Revenue Stream (00:20:01)

Iterating the Business Model and Monetization (00:21:08)

Distribution as the Key Bottleneck (00:22:15)

Leveraging Distribution Channels for Growth (00:23:20)

Conclusion and Call to Action (00:24:39)

I chat with Craig Hewitt , founder of Castos. We talk about his journey from running a podcast editing agency to building a SaaS hosting platform. We cover the challenges of bootstrapping, raising funds, and going international. Craig shares how he uses distribution channels, how AI affects small teams, and what it’s like to scale in a niche market. We end with advice for indie founders on picking business models, taking risks, and keeping up with tech changes.

My twitter: https://x.com/wbetiago

About Craig Hewitt

Twitter: https://x.com/TheCraigHewitt

Podcast: https://roguestartups.com/

Timestamps by Podsqueeze

Greg’s Background and Starting Podcast Motor (00:01:02)

Getting First Clients and Sales Approach (00:06:29)

US vs. Europe: Customer Acquisition Differences (00:08:25)

Localization and Multi-Currency Pricing (00:13:18)

Transition from Agency to SaaS: Castus (00:16:30)

Distribution Channels and Product Positioning (00:19:06)

Impact of AI on Team and Product Development (00:25:28)

Bootstrapping vs. Raising Money: Tiny Seed Experience (00:30:25)

Agency vs. SaaS: Which to Start First? (00:31:33)

Tiny Seed Accelerator: Value and Learnings (00:35:55)

Distribution, Churn, and Growth Challenges (00:38:56)

Balancing Family, Agency, SaaS, and Accelerator (00:41:05)

Using Investment to Scale and the Realities of Raising Money (00:44:05)

Investor Returns and Exit Expectations (00:51:19)

Podcasting Market Realities and Churn (00:54:10)

Pricing, Retention, and Content Marketing Plateau (00:57:23)

What to Do When Growth Plateaus (01:00:59)

AI’s Impact on SaaS and the Economy (01:10:21)

US vs. Europe: Entrepreneurial Mindset Differences (01:14:53)

Conclusion and Where to Find Greg (01:17:58)

Links and Mentions

Tools and Websites

"Castos": "00:01:02"

"Podcast Motor": "00:01:02"

"Audacity": "00:05:40"

"Ecom from Skype": "00:05:40"

"Blueberry": "00:05:50"

"Buzzsprout": "00:05:50"

"Seriously Simple Podcasting": "00:17:36"

"HubSpot": "00:19:14"

"Cursor": "00:15:11"

"Zencastr": "00:22:33"

"Zoom": "00:22:33"

"Figma": "00:24:26"

"Cursor": "00:27:41"

"TinySeed": "00:30:25"

"11 Labs": "00:26:30"

"Claude": "00:26:30"

"Marnus": "00:26:30"

"TinySeed": "00:48:33"

"WordPress": "00:51:19"

"Podsqueeze": "00:54:10"

"Apple Podcast Connect": "00:55:13"

"Rogue Startups": "01:17:58"

Books

"Steal Like an Artist": "00:19:31"

Videos and Podcasts

"Nathan Barry's Podcast": "01:08:40"

I speak about how mindset is shaped by culture and how it impacts business and self-confidence, comparing Portugal, Germany, and the US. I share lessons learned from interacting with entrepreneurs, especially around valuing your work and selling yourself. I talk about my new advertising project, Oliver Media, the challenges of B2B sales, and differences in how people approach business across countries. I reflect on how surrounding yourself with a strong entrepreneurial mindset can change what you believe is possible, and why understanding culture is key for B2B success.

Timestamps by PodSqueeze

Introduction and Episode Overview 00:00:00  

How to Support the Podcast & Contact Info 00:01:29  

Coworking Space Story & Cultural Observations 00:02:52  

Salary Expectations: Portugal vs. Germany 00:03:53  

Cultural Mindset and Its Impact 00:05:24  

Business Mindset: Portugal vs. US 00:06:47  

US Clients and Investment in Projects 00:08:12  

Case Study: Portuguese-American Entrepreneur 00:10:38  

American Attitude Toward Business and Monetization 00:11:50  

Introducing Oliver Media Project 00:12:57  

Building a Podcast Advertising Network 00:14:14  

Challenges in Portuguese Podcast Advertising 00:15:27  

Learning to Sell Advertising as a Product 00:16:35  

B2B Sales Focus and Strategy 00:19:49  

Cultural Nuances in B2B Sales 00:20:57  

Mindset Differences Across Countries and Continents 00:22:02  

Learning from American Business Culture 00:23:21  

Conclusion and Call for Listener Interaction 00:24:34

I reflect on changes in the indie hacking community, especially how Twitter’s algorithm elevated a few “stars” and reduced sharing of useful lessons. I discuss how AI is transforming bootstrapping and SaaS, making coding accessible and raising anxiety about job security. I explore how software is becoming a commodity, what this means for developers and founders, and why owning distribution and marketing will matter most. I share thoughts on diversifying businesses beyond SaaS as AI rapidly evolves, and invite feedback from listeners about their own experiences with AI and entrepreneurship.

Twitter: https://x.com/wbetiago

Linkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/

Timestamps by PodSqueeze

Introduction and Episode Overview (00:00:00)  

Podcast Housekeeping and Call for Reviews (00:01:37)  

Tiago’s Indie Hacking Beginnings (00:03:06)  

Golden Days of Indie Hacking Community (00:04:27)  

Rise of Indie Hacking Stars and Algorithm Shift (00:05:45)  

Vanity Metrics and Decline of Knowledge Sharing (00:07:17)  

Personal Impact and Disconnection from Community (00:10:12)  

Platform Comparison: Twitter vs. LinkedIn (00:12:47)  

Transition to AI and Future of SaaS (00:14:13)  

Personal Story: Co-founder’s Journey with AI Coding Tools (00:14:13)  

AI’s Impact on Coding and Productivity (00:15:56)  

AI in Daily Work and Expanding Use Cases (00:17:09)  

Anxiety Over AI Replacing Computer-Based Jobs (00:20:08)  

Threat of Big Tech and Commoditization of Software (00:21:31)  

Changing Developer Job Market and Skills Gap (00:22:56)  

Importance of Distribution and Marketing (00:25:56)  

Existential Questions: AI Replacing Human Intelligence (00:27:16)  

Human Value in a Post-AI World (00:31:48)  

Diversification as a Survival Strategy (00:34:25)  

Uncertain Future and Final Reflections (00:35:39)

Today I am re-publishing an episode from my early days as an entrepreneur. It kind of seems like it was a lifetime ago. I have learned a lot since then. But its cool to go back in time!

Hope you enjoy it!

Follow me on twitter: https://x.com/wbetiago

Here is the republish of my chat with Rob Walling, author of the SaaS Playbook. We delved into product pricing, focusing on value alignment rather than greed, and discussed strategic price increases to reduce churn and bolster marketing. Rob also shared when to start paid ads and how to create impactful content. He offered advice on assembling a team within budgetary limits and revealed that smart business structuring can lead to profit with less work. Our conversation ended on the importance of joy in entrepreneurship, emphasizing freedom, purpose, and relationships.

These shownotes were created with Podsqueeze

Links and Mentions

SAS Playbook: 01:31:58

Startups for the Rest of Us Podcast: 01:31:58

MicroConf YouTube Channel: 01:31:58

The Zen Founder Guide to Founder Retreats: 01:30:39

Twitter Thread for Book Recommendations: 01:32:37

Timetsamps

Rob Walling's Book (00:01:16)

Writing the Book (00:02:13)

Pricing Strategies (00:06:36)

OpenAI's Pricing Strategy (00:11:54)

Competitive Pricing Strategy (00:13:50)

Greed and Motivation (00:16:40)

Reasons for Raising Prices (00:17:50)

Impact of Pricing on Marketing (00:19:24)

Paid Advertising Considerations (00:20:59)

Using Ads for SEO Strategy (00:24:57)

Marketing Approaches for SaaS (00:29:50)

Creating Compelling Content for Reddit (00:32:38)

Navigating Reddit and Other Forums (00:34:17)

Understanding Marketing and Content Strategies (00:35:20)

Challenges of Early-Stage Product Development (00:38:03)

Defining Product-Market Fit (00:44:48)

Size of the Market (00:48:24)

Total Reachable Market (00:49:01)

Reaching 100% of the Paying Market (00:50:42)

Total Addressable Market (00:51:00)

Escape Velocity (00:54:20)

Business Plateau (00:55:39)

Hiring and Team Growth (00:57:24)

Managing People (01:03:09)

Owner and Founder Level Thinkers (01:04:35)

Challenges of Hiring and Paying Employees (01:05:33)

Remote Work and Cost-Effective Hiring (01:07:18)

Working On vs. In the Business (01:10:33)

Achieving Work-Life Balance and Financial Success (01:14:51)

Earning Wealth and the Challenges of Autopilot Income (01:19:44)

Investing and Selling Assets (01:20:21)

Tax Treatment and Selling SaaS Companies (01:21:14)

Wealth and Freedom (01:22:09)

Finding Happiness as an Entrepreneur (01:23:04)

Retreats and Self-Reflection (01:30:10)

Recommendations and Conclusion (01:31:58)

I interview ChatGPT (calling it Alex) and challenge it to create a roadmap from zero skills to $1M ARR in five years. We break down the best skills to learn (coding, sales), how to choose a profitable niche, and why B2B SaaS for remote creative collaboration is a strong bet. I dive into practical steps: market research, MVP building, pricing, and B2B outreach. I reflect on sales cycles, pricing strategy, and the impact of AI tools on entrepreneurship. I question bootstrapping, validation, and staying ahead as the landscape rapidly evolves.

Timestamps by PodSqueeze

Introduction and Episode Setup (00:00:00)  

Naming ChatGPT and Framing the Challenge (00:02:09)  

Defining “Rich” and Setting the Revenue Goal (00:03:10)  

Defining the Starting Point and Essential Skills (00:04:03)  

Learning to Code in the Age of AI (00:05:56)  

Timeline for Learning Coding Skills (00:07:09)  

Sales as an Alternative Path (00:08:02)  

Combining Skills and Setting the Five-Year Plan (00:09:22)  

Market Selection and Research (00:09:44)  

Examples of Promising Markets (00:10:58)  

Evaluating and Sizing a Market (00:12:01)  

How to Research and Validate a Market (00:13:01)  

Choosing the Best Market Right Now (00:14:06)  

Existing Tools in the Remote Work Space (00:14:43)  

Framework for Finding Opportunities in Remote Work (00:15:17)  

Selecting a Specific Problem to Solve (00:16:20)  

Zeroing in on a Concrete Product Idea (00:17:33)  

Distribution and Go-to-Market Strategy (00:18:13)  

Targeting and Reaching Decision Makers (00:19:19)  

Preparation Timeline for Outreach (00:21:02)  

Warming Up Specific Contacts (00:21:26)  

Example Target Companies (00:22:06)  

Pricing Strategy for B2B SaaS (00:22:48)  

Justifying Tiered Pricing (00:24:14)  

Timeline to Reach 1 Million IRR (00:25:09)  

Step-by-Step Action Plan (00:26:33)  

Closing and Reflections (00:28:03)  

Final Thoughts and Outro (00:36:07)