Indie Founder

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/wbetiagoLinkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/Timestamps por PodSqueezeIntroduction 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/wbetiagoLinkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/Timestamps by PodsqueezeIntroduction 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/wbetiagoAbout Craig HewittTwitter: https://x.com/TheCraigHewittPodcast: https://roguestartups.com/Timestamps by PodsqueezeGreg’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 MentionsTools 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 PodSqueezeIntroduction 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

The discussion dives into how AI is reshaping indie hacking and SaaS, raising questions about job security and the commoditization of software. The impact of Twitter's algorithm on community dynamics and knowledge sharing is examined, highlighting the rise of a few standout figures. Concerns about AI replacing human creativity are raised, alongside strategies for diversifying business models. Listeners are encouraged to share their experiences navigating this evolving landscape, adding to the rich conversation around entrepreneurship.

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 PodsqueezeLinks and MentionsSAS Playbook: 01:31:58Startups for the Rest of Us Podcast: 01:31:58MicroConf YouTube Channel: 01:31:58The Zen Founder Guide to Founder Retreats: 01:30:39Twitter Thread for Book Recommendations: 01:32:37TimetsampsRob 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)

Discover how to build a million-dollar business from scratch! The conversation delves into essential skills like coding and sales, and discusses the rising potential of B2B SaaS for remote collaboration. Learn practical steps for market research, MVP creation, and pricing strategies. The host reflects on the impact of AI tools on entrepreneurship, emphasizing the need for continuous learning and adaptation. With insights on identifying lucrative niches and effective outreach, this roadmap offers valuable guidance for aspiring indie founders.

I talk about my personal dilemma: should I buy a boat now or wait? I share my love for sailing, the costs and challenges of boat ownership, and my ideas to make it affordable—like renting it on Airbnb. I discuss chasing dreams versus saving or investing money, and ask if achieving goals is better than the journey itself. Finally, I mention trying to negotiate the boat price by offering my web skills. I’d love your feedback—message me on Twitter (@wbtiago).My Twitter: https://x.com/wbetiagoTimestamps by PodSqueezeIntroduction and Personal Dilemma (00:00:01)  Podcast Housekeeping & Audience Engagement (00:00:52)  The Caribbean Fisherman Story (00:01:56)  Reflection on Chasing Success (00:03:00)  The Gambler and the Devil Story (00:05:13)  Current Financial Situation (00:06:34)  Passion for Sailing and Background (00:07:36)  Debating the Investment (00:08:41)  Understanding the Value of the Chase (00:09:42)  Practical Challenges of Boat Ownership (00:10:51)  Marina Costs and Scarcity (00:12:02)  Boat Depreciation and Resale Value (00:13:15)  Offsetting Costs: Airbnb Rental (00:14:20)  Offsetting Costs: Tourism Experiences (00:15:23)  Offsetting Costs: Renting to Sailors (00:17:17)  Focusing on Airbnb as the Best Option (00:18:12)  Negotiating with the Boat Owner (00:19:20)  Next Steps and Request for Advice (00:20:16)  Episode Wrap-Up and Recommendation (00:21:21)