Best Craig Hewitt At Castos Podcasts (2025)

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 enter…

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#360 - Bootstrapping vs Raising Funds: How AI Is Changing the Game for Indie Founders 26:42

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1M ago26:42

26:42

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 st…

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#359 - Interviewing Craig Hewitt on International Expansion, AI and Raising Funds While Building Castos 1:15:18

1M ago1:15:18

1:15:18

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…

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#358 - How Does Mindset Shape Your Business Success Across Cultures? 24:05

2M ago24:05

24:05

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 differ…

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#357 - Is Indie Hacking Dead Or Will It Be Killed By AI? 35:49

2M ago35:49

35:49

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…

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#356 - A day in a life of an entrepreneur [Re-published] 7:45

2M ago7:45

7:45

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/wbetiagoBy Tiago Ferreira

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#355 - Rob Walling on How To Build a SaaS [Re-Published] 1:33:51

2M ago1:33:51

1:33:51

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 te…

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#354 - I Asked ChatGPT How To Get to $1M ARR! 35:54

3M ago35:54

35:54

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 B…

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#353 - Should I Buy My First Sailboat? 22:24

3M ago22:24

22:24

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 t…

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#352 - Which Businesses Have the Best Multiples in 2025? 23:52

3M ago23:52

23:52

I break down key insights from a digital business acquisition report by Flippa. I share which business models are getting the highest multiples (SaaS, content sites, YouTube channels), highlight surprising trends in buyer interest, explain what affects deal speed and size, and give quick tips for founders considering selling (or buying) right now. …

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#351 - Market Validation, Churn Reduction & Bootstrapping ScreenshotOne.com to $20K MRR with Dmytro 57:22

3M ago57:22

57:22

In this episode, I sit down with Dmytro, founder of ScreenshotOne.com, to uncover how he bootstrapped his SaaS tool for automated website screenshots to an impressive $20K MRR. We dive deep into the market validation process that gave ScreenshotOne.com an edge, explore real-world use cases, and discuss the early challenges Dmytro faced as an indie …

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#350 - Mastering B2B Sales: Strategies for Indie Founders 28:14

4M ago28:14

28:14

I share my journey into B2B sales, detailing the strategies that helped me land clients for my company, Podsqueeze. I discuss the differences between B2B and B2C, the importance of identifying target leads, and effective outreach methods, including using WhatsApp. I cover the demo process, follow-up negotiations, and the significance of maintaining…

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#349 - How Indie Makers Can Leverage Press Releases & Niche Marketing to Boost Visibility 22:31

4M ago22:31

22:31

I share a recent breakthrough in my entrepreneurial journey with Podsqueeze. After experimenting with various marketing strategies, I discovered the power of targeted press releases. Initially, I struggled with traditional PR methods, but I found success by reaching out to niche podcasting newsletters. This approach not only increased our visibilit…

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#348 - What Defines a Good Entrepreneur? The Power of Value Creation, Continuous Learning & Building a Self-Sustainable Business 25:14

4M ago25:14

25:14

I discuss the definition of a successful entrepreneur and what constitutes a company. I share my perspective on profitability and value creation, emphasizing that a true business should be self-sustainable. I explore the role of luck in entrepreneurship and reflect on my journey with Podsqueeze, including the challenges of replicating success. I co…

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#347 - The Market Doesn’t Care: Realities of Entrepreneurship 24:42

5M ago24:42

24:42

I share my journey with Podsqueeze, reflecting on two years of entrepreneurship. I discuss the impact of seasonality on our business and the brutal nature of the market. I explore the challenges of balancing investment and salary, leading to a decision to scale down operations. I highlight our shift towards B2B clients and the lessons learned from …

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#346 - Reflections on 2024: Achievements, Challenges, and the Power of Sustainable Marketing 30:56

10M ago30:56

30:56

I share a wrap-up of 2024, discussing both successes and challenges with Podsqueeze. I reflect on our disappointing growth compared to 2023 and the importance of sustainable marketing, particularly through SEO, which significantly increased our traffic. I analyze our MRR growth of 18% and the ongoing issue of churn, which remains a focus for 2025. …

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#345 - Navigating Residential Building Management: Overcoming Challenges and Cultural Clashes 34:51

10M ago34:51

34:51

I dive into my journey of managing a residential building after buying our first apartment. I share the ups and downs of dealing with a crumbling building, a lackluster management company, and a diverse group of neighbors from different cultural backgrounds. I talk about how I took charge, rallied the residents, and navigated through conflicts to i…

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#344 - Cracking the Productivity Code: Balancing Work Satisfaction and Personal Time for Indie Makers 27:18

11M ago27:18

27:18

I dive into the tricky balance between work and rest that many indie makers face. I share my personal journey and talk about the constant pressure to work long hours and the feelings of dissatisfaction that can arise in both 9-to-5 jobs and startups. I emphasize the importance of finding fulfillment and suggest that entrepreneurs should delegate ta…

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#343 - Network Used To Be Awkward... Lets Talk About Websummit 24:01

11M ago24:01

24:01

I dive into the art of networking at conferences, focusing on my experiences at the Web Summit in Lisbon. Having attended for three years, I share tips on navigating the event, securing a media ticket, and making meaningful connections. I emphasize the importance of networking over attending talks, recounting my interactions with various companies,…

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#342 - Currency Fluctuations and Trump's Victory: Impacts on Indie Maker's Businesses 27:04

12M ago27:04

27:04

I dive into the potential impacts of Donald Trump's election victory on indie businesses, especially in the SaaS sector. I discuss the differences between the U.S. and European business environments, noting how higher purchasing power in the U.S. can benefit indie makers. I also touch on corporate tax rates, tariffs, and currency fluctuations. Whil…

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#341 - How Your Ego Is Killing Your Business! 31:48

12M ago31:48

31:48

I dive into the importance of setting aside ego in both entrepreneurship and personal life. I share personal stories and lessons learned, emphasizing that being an entrepreneur is a lifestyle that shapes one's worldview. I talk about how different professions influence perspectives and highlight the value of self-belief and adaptability. I encourag…

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#340 - Navigating Scaling Challenges and User Feedback: Elston's Indie Journey with Tiny Host 1:21:26

12M ago1:21:26

1:21:26

I chat with Elston, founder of Tiny Host. We dive into his journey as an indie maker, his early interest in web design, and the founding of Tiny Host. We discuss validating business ideas, building Tiny Host from an MVP to a user-friendly tool, and the importance of user feedback and market research. We also touch on scaling challenges and the diff…

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#339 - From Stagnation to Success: Reviving User Engagement with Podsqueeze 38:00

1y ago38:00

38:00

I share the rollercoaster journey of my startup, Podsqueeze. I talk about our initial success, hitting a growth plateau, and the strategies we used to bounce back, like investing in SEO and launching new features. I dive into the emotional highs and lows of entrepreneurship, the importance of teamwork, and the challenges of maintaining motivation. …

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#338 - New Name! New Product! New Season! 25:57

1y ago25:57

25:57

I discuss the evolution of my podcast and why It went from "The Wannabe Entrepreneur" to "Indie Founder." I introduce Flarecut, my new AI tool that helps create short videos. I reflect on its market reception so far and why it might be failing. Mentions Podsqueeze (00:06:41) - https://podsqueeze.com Flarecut (00:12:52) - https://flarecut.com Auto S…

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#337 - Unveiling the Myth: Overworking and Work Performance in the Path to Wealth 33:38

1+ y ago33:38

33:38

In this episode, I dive into my latest thoughts on entrepreneurship, work-life balance, and productivity. I share exciting updates about my project, Podsqueeze, and my collaboration with João on a new product. I discuss the struggle of balancing work with personal life and question traditional metrics of productivity. We also touch on the culture o…

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#336 -Why Business Size Matters: Navigating a Bootstrapped Company and New Projects 33:34

1+ y ago33:34

33:34

I talk about the importance of prioritizing tasks and managing time effectively. I also discuss my main goal: becoming a better entrepreneur through continuous learning. You'll hear about my marketing strategies, especially focusing on Google SEO, and the challenges of growing a bootstrapped company. Plus, I reflect on the slow growth of Podsqueeze…

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#335 - Navigating Business Metrics and My Podcasting Conference Journey - Young Entrepreneur Mistakes 26:58

1+ y ago26:58

26:58

I made a mistake with my pricing, but I'm getting over it with some meditation. I'm also excited to go to a podcast conference in London to meet people and learn more. I talked about the importance of understanding business metrics to make good decisions, not just to look impressive. Also, AI is becoming a big deal in our field, and I'm watching ho…

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#334 - Rob Walling on Mastering Product Pricing for Churn Reduction and Entrepreneurial Wealth - Author of The SaaS Playbook 1:33:51

1+ y ago1:33:51

1:33:51

Here is 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 budgeta…

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#333 - Thriving in Your 30s: Embracing Community Building and Entrepreneurship 27:18

1+ y ago27:18

27:18

I've been reflecting on the growth and changes over the past few years. We talked about the leap from a 9 to 5 to full-time entrepreneurship, the societal pressures we face, especially as we hit our 30s, and the quest for work-life balance. I also pondered the idea of renting an office space to combat the solitude of working from home and to build …

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#332 - Money, Time and Fun - You Can Have It All! 26:22

1+ y ago26:22

26:22

In today's podcast, I dive deep into how we juggle our time, chase wealth, and strive for that elusive work-life balance. I shared some personal stories, including the ups and downs with my own project, Podsqueeze, and how I'm tackling growth challenges head-on. We also talked about why we leave cushy jobs to strike out on our own—is it for freedom…

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#331 - Unlocking Organic Growth: The Hidden Tool Transforming Businesses 24:01

1+ y ago24:01

24:01

I'm happy to share some personal updates and entrepreneurial insights. Lately, I've discovered Apollo, a networking tool that's completely revolutionized the way I connect with others. Our Website was completely down for a complete 30 min and I have never beens this stressed XD And to continue this stressing week we decided to increase Podsqueeze p…

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#330 - Unlocking Productivity: How "The 4-Hour Workweek" Revolutionizes Entrepreneurial Efficiency 22:48

1+ y ago22:48

22:48

I dive into the nation's burgeoning immigration scene, exploring its cultural boons and economic hurdles. As a business owner, my political perspectives are ever-shifting, particularly concerning taxes and government policies. Plus, I'll reveal my journey towards achieving a work-life balance and heightened productivity, inspired by "The 4-Hour Wor…

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#329 - Strategic Investing Strategies Post-Company Sale with Daniel's $500K SaaS Portfolio 1:26:54

1+ y ago1:26:54

1:26:54

Hey fellow indie hackers, just wrapped up a super cool chat with Daniel, a 26-year-old entrepreneur who's totally killing it with a $500k SaaS portfolio. He and his brother started young, sold their first company, and now they're smartly reinvesting into more SaaS, real estate, and other assets. Daniel's all about that cautious growth and avoiding …

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#328 - Rob Walling's Game-Changing Book: Strategies for Makers on Reducing Churn and Embracing Long-Term Thinking 25:08

1+ y ago25:08

25:08

Hey fellow indie hackers! I've promised myself (and you guys!) that from now on, I'll drop a fresh episode every Monday – gotta keep that trust going, right? I also dived into my new adventure with PodSqueeze, chatting with customers on the podcast and soaking up all their amazing insights. Oh, and I had this awesome talk with Rob Walling, which le…

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#327 - Unlocking Product Growth: The Role of Early Adopters and Marketing Tactics 20:42

1+ y ago20:42

20:42

Why do some products grow more than others? In today's episode of "The Wannabe Entrepreneur," I ponder over the growth trajectory of my product, the inevitable plateau, and the significance of early adopters and the early majority. I confess to overlooking long-term marketing tactics initially and discuss strategies to break into fresh markets, lik…

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#326 - Growing Together: Mastering Customer Retention for Financial Success 22:50

1+ y ago22:50

22:50

I'll talk about the crucial skill shifts, strategies to keep customers, the art of delegation, and the power of SEO and email marketing. Learning from fellow entrepreneurs has been key, and I'm eager to show that bootstrapping can lead to serious financial wins. Links Support This Podcast DM me on Twitter Join The WBE Community Try PodSqueeze Times…

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#325 - Transform Your Entrepreneurial Journey: Invest in Marketing Expertise! 26:12

2y ago26:12

26:12

Ever wondered how a developer turns into an entrepreneur? In this episode of "The Wannabe Entrepreneur," I, Tiago, dive into my own transformation, revealing the ins and outs of my entrepreneurial journey. I'll walk you through the crucial role of passive user acquisition strategies, such as SEO and content creation, and explain why it's essential …

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#324 - Guerrilla Marketing and Podcast Creation: Launch Your Show in 24 Hours! 29:08

2y ago29:08

29:08

Are you ready to dive into the world of guerrilla marketing and podcasting? I'm Tiago, the host of "The Wannabe Entrepreneur" and co-founder of PodSqueeze. In this episode, I'm excited to share our marketing focus for early 2024 and the behind-the-scenes of our rapid-fire podcast creation, "Lessons from a Podcaster." I'll walk you through our launc…

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#323 - From $0 to $100K in One Year: Our Rapid Prototyping and Product Launch Journey 56:02

2y ago56:02

56:02

In this episode, together with my co-founder João, we dive into our entrepreneurial rollercoaster with Pod Squeeze. From the ashes of a failed project to the thriving business we run today, we're peeling back the curtain on our journey. We'll chat about the crucial role of user feedback, the exhilarating boost from financial wins, and the gritty de…

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#322 - Overcoming Startup Plateau: Growth Strategies for Reaching the Early Majority 18:51

2y ago18:51

18:51

Are you an entrepreneur facing challenges and feeling frustrated with the stagnation of your company? In this episode, I, Tiago, the host and co-founder of Podsqueeze, share my own experiences and insights. Despite the difficulties, I realize that our achievements are impressive. I discuss a conversation I had with a Portuguese entrepreneur and inv…

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#321 - My Entrepreneurial Journey: From $100K Milestone to $1M Success 29:10

2y ago29:10

29:10

In this episode of "The Wannabe Entrepreneur," we will be exploring a range of topics. I will start by discussing the challenges of buying a new home and the art of gift-giving, sharing my personal experiences. Then, I will delve into the world of influencer marketing and compare working cultures in Portugal and Germany. I will express my frustrati…

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#320 - Mastering the Art of Selling Startups: Insights from Andrew Gazdecki 1:24:00

2y ago1:24:00

1:24:00

Have you ever wondered about the process of selling startups? In this podcast episode I had the pleasure of interviewing Andrew Gazdecki, the founder of Acquired.com. We dive into his experience of scaling his company and the significance of having a distribution mindset and a strong team. Join us as we explore the importance of delegation, hiring …

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#319 - From Cheating at a Podcast Festival to Sponsoring It 24:06

2y ago24:06

24:06

Let me take you on a rollercoaster journey through my experiences. This week, I've experienced both the highs and lows of this exciting world of indie hacking. Join me as I share the challenges of running PodSqueeze and managing co-founder relationships. I will also speak about our most recent sponsored event and gaining recognition in the Portugue…

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#318 - Maximizing Networking with Business Cards at Tech Conferences 24:02

2y ago24:02

24:02

What it's like to attend a major tech conference like the Web Summit? Well, in this episode, I'll be sharing my personal experiences from the event. Despite all the controversy and big tech companies dropping out, the turnout was massive! I'll be discussing my networking strategies, like using the event app to connect with people and finding a quie…

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#317 - How Blocking Fake Accounts Impacted User Engagement and Business Growth 27:02

2y ago27:02

27:02

Have you ever made a critical mistake that had a significant impact on your business? In this episode, I'll be sharing my own experience as the co-founder of Podsqueeze. Blocking the upload feature to combat fake accounts seemed like a good idea at the time, but it ended up causing a decrease in user engagement and revenue. I'll be discussing the i…

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#316 - Interviewing Dagobert About How to Avoid Burnout as a Founder 1:36:52

2y ago1:36:52

1:36:52

Have you ever experienced burnout and its impact on your health? Well, Dagobert shares his personal experience with burnout and how it led to a significant shift in his work-life balance. We also dive into the importance of therapy for mental health and how it played a crucial role in Dagobert's recovery. Links Follow Dagobert's Twitter Join The WB…

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#315 - How to Sponsor a Conference with your Indie Maker Business 30:38

2y ago30:38

30:38

Have you ever sponsored a conference to grow your business? In this episode, I, an indie maker, and my co-founder Joao, dive into our experience sponsoring a conference in Berlin for our company, Podsqueeze. We were initially worried about being scammed, but we ended up sealing a sponsorship deal for $700. I chat about the perks of attending such e…

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#314 - Securing Funding: Daniel's Journey with Wundertax from Startup Challenges to Success 1:13:34

2y ago1:13:34

1:13:34

I am interviewing Daniel, the CEO of Wundertax. He takes us on a journey from Hong Kong to Germany, sharing his experiences in entrepreneurship and the creation of Wundertax. We dive into the challenges of starting a business, securing funding, and navigating co-founder dynamics. Daniel also shares insights from his time in Amsterdam and how Wunder…

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#313 - Betting Big on a Podcasting Conference: New Features and Entrepreneurial Insights 14:04

2y ago14:04

14:04

I have some exciting news to share - our company has decided to sponsor a podcasting conference in Berlin as part of our marketing strategy. I'll be discussing our experimentation with different approaches like cold emails and automation, as well as our current focus on sponsoring conferences. Join me as I talk about my goals for attending the conf…