Best Bootstrapped Web Podcasts (2025)

1
2025 recap & 2026 outlook 1:02:58

Play Pause

1d ago1:02:58

1:02:58

Hey! Back in your feed for our bi-annual updates! It's December 2025 and that means it's time for our year-end recap and year-ahead outlook. What Jordan's up to: Rosie Offiste Podcast Jordan on X What Brian's up to: Builder Methods YouTube Agent OS & Design OS Panel Podcast Brian on XBy Bootstrapped Web

1
#989 - WP-Tonic Show: Lessons Learned Launching a Successful WordPress Service Plugin 50:24

1h ago50:24

50:24

Lessons Learned Launching a Successful WordPress Service Plugin Discover key lessons learned launching a WordPress service plugin. Avoid costly mistakes and accelerate your plugin's success today. With Special Guest Ben Sibley, Co-Founder of Independent Analytics https://independentwp.com/ #1 - Ben, can you give the tribe more info on how you got i…

1
#367 - We Just Moved In To Our Own Office 24:43

5d ago24:43

24:43

I share the story behind getting our first dedicated Podsqueeze office in Portugal. I talk about the challenges of moving from a co-working space, hunting for a budget-friendly place, and doing DIY renovations with my co-founder. I explain how we furnished the space cheaply, set up a gym and podcast studio, and optimized for productivity. I cover o…

1
#988 - WP-Tonic Show:We Look At Our Most Powerful Interviews In 2025 52:09

5d ago52:09

52:09

We Look At Our Most Powerful Interviews In 2025 Our most powerful interviews in 2025 revealed: Game-changing conversations with visionaries you need to hear. Don't miss these stories. In 2025, we dive deep into the most impactful interviews that shaped our understanding of key issues. This episode features extraordinary discussions with influential…

1
D2C Without a Tax Degree: How to Sell On a Web Shop Without Becoming a Tax Expert 24:39

12d ago24:39

24:39

You didn’t build a game studio to become an expert in global tax law. But as more publishers move from marketplaces to direct-to-consumer (D2C) web shops, the burden of tax compliance shifts from Apple and Google directly to you. In this episode, we sit down with Rachel Harding, Senior Director of Tax at FastSpring, to demystify the complex world o…

1
How to Scale Playable/Interactive Ad Strategies with Elina Arponen of Quicksave 31:01

19d ago31:01

31:01

Thanks to technologies like WebGL, mobile UA teams now have powerful tools for building incredibly interactive and playable ads that take what is possible to an entirely new level. While many of us have embraced this trend, there still remains one huge problem. TIME. Producing playable/interactive ads can bring our creative teams to their knees whi…

1
RS354: The State Of Podcasting Heading Into 2026 41:22

9d ago41:22

41:22

Craig is back! Today, he welcomes fellow podcaster Colin Gray back to the podcast. They dive into the ever-evolving world of podcasting, reflecting on how much the landscape has shifted over the last decade and what people are craving now more than ever: genuine human connection. From the tug-of-war between YouTube and podcast growth, to what it re…

1
#987 - WP-Tonic Show: Are The Glory Days of SaaS Finished in a World of AI? 58:16

10d ago58:16

58:16

Are The Glory Days of SaaS Finished in a World of AI? Rob Walling, Founder of Tinyseed, MicroConf & Podcast "The Startups For The Rest of Us" Are the glory days of SaaS over as AI transforms software? Explore how artificial intelligence is reshaping the SaaS landscape forever. ---------------------- Sponsors of The Show ----------------------------…

1
#986 - WP-Tonic Show:The Future of Cloud Hosting in a World of AI 53:18

1M ago53:18

53:18

#986 - WP-Tonic Show: The Future of Cloud Hosting in a World of AI The Future of Cloud Hosting in a World of AI The future of cloud hosting meets AI: Explore intelligent infrastructure, predictive scaling, and next-gen solutions transforming businesses. With Special Guest Suhaib Zaheer, Senior Vice President and General Manager of Managed Hosting a…

1
#366 - I Took My First Step In Politics And You Should Do It Too! 38:02

18d ago38:02

38:02

I share my journey stepping into local politics. I discuss my experience exploring a political party, why direct impact is difficult, and my thoughts on democracy, transparency, and capitalism. I reflect on how entrepreneurs can contribute outside traditional politics, the role of technology in future democracy, and ideas for making systems more tr…

1
#365 - Why Did I Wear a Suit to Web Summit? Spoiler: It Worked! 31:16

23d ago31:16

31:16

I share updates on negotiating for a new office, including the challenges with the landlord and contract terms. I reflect on changing my dress code at Web Summit, how it affected others’ perceptions and my self-confidence. I discuss Web Summit highlights—AI hype, standout startups, and networking moments. Finally, I break down my latest automations…

1
#985- WP-Tonic Show:From The Longest Night To Making $114,238 in 15 Days 1:01:00

1M ago1:01:00

1:01:00

From The Longest Night To Making $114,238 in 15 Days We have a great interview coming up with Dustin, founder and CEO of the popular AI tool Magai. He has an amazing personal story, and we will also discuss some of the major lessons he has learnt from growing Majai. Why don't you join us live with your questions for Dustin? https://f0k0.short.gy/Zu…

1
984 - WP-Tonic This Month in WordPress & Tech Round Table Show For October, 2025 55:10

2M ago55:10

55:10

WordPress and Tech Stories of The Month. Get the insights you need now. Discover the month's must-know WordPress and tech stories in our latest video! We explore key updates, fascinating innovations, and expert commentary that are vital for anyone involved in the digital realm. Our engaging discussion keeps you informed and inspired as you navigate…

1
#364 - How a Loud Neighbor Pushed Us to Get Our Own Office 31:04

1M ago31:04

31:04

I share my journey from working at home to trying co-working spaces, and then renting my own office. I talk about challenges like noise and limited hours that made me and my co-founder look for a better fit. Now, with our own office, we have more freedom, flexibility, and the chance to build a community of indie makers. If you’re bootstrapping your…

1
983 - WP-Tonic Show - What Does It Take To Build A Successful Web Design Agency: At The End of 2025 55:49

2M ago55:49

55:49

Discover what it takes to build a successful web design agency with expert insights from Imran Siddiq of Web Squadron. Get proven strategies now. In this insightful show, Imran Siddiq from Web Squadron shares the essential steps for establishing a thriving web design agency. From mastering client relationships to honing technical skills, Imran reve…

1
#363 - How I Automated My Indie Business with AI and n8n 20:00

1M ago20:00

20:00

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 w…

1
The Dramatic Rise of Web in Gaming: How Top Publishers & Studios Are Building Innovative Web Teams With Caleb Brown of X-Team 35:42

2M ago35:42

35:42

There are few moments in an industry's history where a trend or emerging technology introduces a step function that unlocks an entirely new level of growth. With the rise of D2C and other web based experiences, game publishers are experiencing a rare opportunity to increase profits and establish better long term relationships with players. But how …

1
982 - WP-Tonic Show: AI & WordPress The Good, The Bad & The Ugly 1:09:08

2M ago1:09:08

1:09:08

Discover AI & WordPress pros and cons! From automated content creation to security risks - get the complete guide to using AI with WordPress. Our Special Guest This Week Is Matt Medeiros of Gravity Forms & The WP Minute Podcast In this week's show, we delve into the powerful intersection of AI and WordPress, uncovering its advantages and pitfalls. …

1
981 - WP-Tonic Show: How To Build a Successful Plugin Business in 2025 48:54

2M ago48:54

48:54

How To Build a Successful Plugin Business in 2025 With Special Guest Devin Walker of RollBack Pro & Give WP Learn how to build a successful plugin business in 2025 with proven strategies, monetization tips, and market insights. Start your profitable journey today. In this video, we explore the key strategies for establishing a successful plugin bus…

1
Pricing & Packaging for Game Web Stores with Chip Thurston of FastSpring 32:18

2M ago32:18

32:18

By FastSpring

1
980 - WP-Tonic Show: We Discuss The Challenges of Building a Real Online Community in 2025 53:44

3M ago53:44

53:44

By Jonathan Denwood & Kurt von Ahnen

1
#362 - The Best Strategies for Bootstrapped Founders at Business Conferences 23:04

2M ago23:04

23:04

By Tiago Ferreira

1
RS353: Is This the Last Organic Marketing Channel 50:57

3M ago50:57

50:57

In today’s episode, Craig sits down with SaaS founder and entrepreneur Brian Casel to talk about the future of software and AI. With years of experience building and growing SaaS companies, Brian shares his perspective on how artificial intelligence is reshaping the industry, from launching in niche markets and creating content that resonates to th…

1
#361 - Mastering the Art of Pricing: Balancing B2C Sensitivity with B2B Value 21:49

3M ago21:49

21:49

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…

1
#979- WP-Tonic This Month in WordPress & Tech Round Table Show For September, 2025 1:07:37

3M ago1:07:37

1:07:37

WordPress and Tech Stories of The Month. Get the insights you need now. Discover the month's must-know WordPress and tech stories in our latest video! We explore key updates, fascinating innovations, and expert commentary that are vital for anyone involved in the digital realm. Our engaging discussion keeps you informed and inspired as you navigate…

1
RS352: AI Killed Traditional Marketing – Here's What's Next 49:33

3M ago49:33

49:33

Ross Simmonds, founder of Foundation Marketing, has built a reputation for helping ambitious SaaS and B2B brands stand out online with data-driven growth strategies. In this episode, Craig sits down with Ross to dive into the future of marketing, SaaS growth, and social media in the age of AI. Marketing has transformed dramatically over the past de…

1
978 - WP-Tonic Show: We Discuss Local SEO and Speed to Lead in 2025 54:42

3M ago54:42

54:42

978 - WP-Tonic Show: We Discuss Local SEO and Speed to Lead in 2025 Master Local SEO and Speed to Lead techniques that convert searchers into customers instantly. Transform your local marketing today. In this show, we dive into the essential elements of Local SEO and its impact on your business's visibility. Discover how optimizing your online pres…

1
#360 - Bootstrapping vs Raising Funds: How AI Is Changing the Game for Indie Founders 26:42

3M 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…

1
RS351: Why Brands Fail on Reddit 45:05

3M ago45:05

45:05

Today on the podcast, Craig sits down with Reddit marketing expert Paul Xue to explore how brands can tap into one of the internet’s most engaged and skeptical communities. Reddit can be a tough nut to crack, but when approached with authenticity and a strategic approach, it can become a powerful driver of trust, visibility, and growth. Paul, found…

1
977 - WP-Tonic Show: Why Being A Guest On A Podcast Is A Great Idea 54:14

3M ago54:14

54:14

Why Being A Guest On A Podcast Is A Great Idea Discover why being a guest on a podcast boosts your brand, expands your network, and positions you as an industry expert. Start your podcast tour today. Discover why appearing as a guest on a podcast can be a game-changer for you! In this informative show, we highlight the advantages of sharing your in…

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

3M 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…

1
RS350: Authenticity, Content Strategy, and the Future of Marketing with AI 57:23

3M ago57:23

57:23

Startup marketing can feel like a maze, right? In this episode of Rogue Startups, Craig chats with Brendan Hufford of Growth Sprints about how to cut through the noise and actually connect with your audience. They dig into everything from creating raw, authentic content to dialing in your SEO strategies and uncovering your brand’s real voice. If yo…

1
976 - WP-Tonic Show: We Discuss The Power of Podcasting In 2025 55:54

3M ago55:54

55:54

Unlock the power of podcasting in 2025 with proven strategies for growth, monetization, and audience building. Your complete guide to podcast success. In this insightful video, we explore the transformative power of podcasting in 2025. Discover how technological advancements and evolving listener preferences are reshaping the podcasting landscape. …

1
#358 - How Does Mindset Shape Your Business Success Across Cultures? 24:05

3M 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…

1
#357 - Is Indie Hacking Dead Or Will It Be Killed By AI? 35:49

3M 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…

1
RS349: Ranking In ChatGPT with Devesh Khanal 1:03:42

4M ago1:03:42

1:03:42

Today on Rogue Startups, Craig sits with Devesh Khanal from Grow and Convert to talk about how to get your brand showing up at the top of search results in LLMs. They dive deep into the world of AI SEO—covering everything from debunking myths about large language models to sharing actionable strategies for ranking your content in both Google and AI…

1
#975 - WP-Tonic This Month in WordPress & Tech Round Table Show For August, 2025 55:24

4M ago55:24

55:24

WordPress and Tech Stories of The Month. Get the insights you need now. Discover the month's must-know WordPress and tech stories in our latest video! We explore key updates, fascinating innovations, and expert commentary that are vital for anyone involved in the digital realm. Our engaging discussion keeps you informed and inspired as you navigate…

1
974 - WP-Tonic Show: We Discuss The Challenges of Building a New Plugin Solution in 2025 (Creator LMS) 52:34

4M ago52:34

52:34

Exploring Plugin Solution Creator LMS: Next-gen development insights, advanced functionality & game-changing features for modern education. In this video, we delve into the exciting journey of developing a new plugin solution for Learning Management Systems (LMS). Discover how this innovative tool enhances user experience, streamlines course creati…

1
2025 Mid-Year Update 1:09:53

4M ago1:09:53

1:09:53

We're back for a mid-year update! The last time we were on the mics together it was January 2025. So what's the outlook 8 months into the year? What we're working on: Jordan's in rocket ship mode on Rosie. Brian's building Builder Methods and YouTubing. Don't be a stranger! Jordan on X: @jordangal Brian on X: @casjam We're still podcasting here: Jo…

1
973 - WP-Tonic Show: Red Flag Issues With New & Existing Clients 53:28

4M ago53:28

53:28

Red Flag Issues With New Clients & The Right Tech Stack For WordPress Freelancers in 2025 Avoid costly mistakes! Learn to spot red flag issues with new clients & choose the right tech stack for WordPress freelancing success. Join us as we uncover the key red flags that could signal trouble with new clients in 2025. This video also highlights the op…

1
#356 - A day in a life of an entrepreneur [Re-published] 7:45

4M 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

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

4M 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…

1
#972- WP-Tonic This Month in WordPress & Tech Round Table Show For July, 2025 1:00:29

5M ago1:00:29

1:00:29

WordPress and tech stories. Get the insights you need now. Discover the month's must-know WordPress and tech stories in our latest video! We explore key updates, fascinating innovations, and expert commentary that are vital for anyone involved in the digital realm. Our engaging discussion keeps you informed and inspired as you navigate your tech jo…

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

4M 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…

1
The Hidden Science of Email: Authentication, Deliverability, and Trust With Hank Hoffmeier of Kickbox 39:47

5M ago39:47

39:47

Conversation with Kickbox Director of Operations Hank Hoffmeier about the science of email marketing. Email marketing is often hailed as the highest-ROI channel — especially for SaaS and digital product companies. But what happens when your emails don’t even make it to the inbox? In this episode of Growth Stage, we speak with Hank Hoffmeier, email …

1
971 - WP-Tonic Show: Does AI Mean The End of Developers Or Is It Just a New Powerful Development Tool? 57:46

5M ago57:46

57:46

Is AI the end of developers or just a new tool? Discover how AI is reshaping coding and what it means for the future of software development. In this thought-provoking video, we explore the impact of artificial intelligence on the world of software development. Is AI set to replace developers, or is it merely evolving the tools at their disposal? J…

1
#353 - Should I Buy My First Sailboat? 22:24

5M 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…

1
970 - WP-Tonic Show: We Discuss All Things Performance & WordPress 58:47

5M ago58:47

58:47

We Discuss All Things Performance & WordPress With Special Guest Remkus de Vries, Founder of Truer Than North & The Co-founder of Scanfully, plus the podcast "Within WordPress Podcast." In this video, we delve into the intricate relationship between performance and WordPress. Join us as we explore essential tips and strategies to optimize your Word…