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Rogue Startups
RogueStartups
50 episodes
3 weeks ago
On Rogue Startups we share the journey of startup founders as they're growing their businesses. We feature experts in the fields of sales, marketing, and product development to hear how they're growth hacking their productized services and SaaS products. If you're on the journey of an entrepreneur then tune and hear how we're tackling some of the same obstacles you may be facing, and how we're winning in the game of business. Listeners of Startups for the Rest of Us, My First Million, Mixergy, and Bootstrapped Web will love checking out our show.
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Entrepreneurship
Technology,
Business
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All content for Rogue Startups is the property of RogueStartups and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
On Rogue Startups we share the journey of startup founders as they're growing their businesses. We feature experts in the fields of sales, marketing, and product development to hear how they're growth hacking their productized services and SaaS products. If you're on the journey of an entrepreneur then tune and hear how we're tackling some of the same obstacles you may be facing, and how we're winning in the game of business. Listeners of Startups for the Rest of Us, My First Million, Mixergy, and Bootstrapped Web will love checking out our show.
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Entrepreneurship
Technology,
Business
Episodes (20/50)
Rogue Startups
RS348: Not Exactly White Hat AI-SEO with Lars Lofgren
In today’s episode, Craig sits down with AI-SEO expert Lars Lofgren to unpack the future of AI-SEO in a world dominated by artificial intelligence. They explore how to attract and retain traffic through both on-site and off-site strategies like Reddit, YouTube, LinkedIn, and beyond. With AI rapidly reshaping the digital landscape, the traditional rules of content and inbound marketing are being rewritten. Should SEO still be your top focus? How do you build brand authority when search algorithms are changing every day? Tune in for practical tips and bold insights on what’s working now—and what’s next. Highlights from Craig and Lar’s conversation: What does SEO even mean in the age of AI? How the search landscape has shifted with AI’s rise The #1 thing to do now to thrive in AI-powered search results Top of Funnel (TOFU) vs Bottom of Funnel (BOFU) marketing Why Google prioritizes specific landing pages for specific products The companies gaming AI—and how it’s disrupting traditional SEO How to get your brand seen in AI answers and social media feeds The surprising impact of Reddit on SEO strategy Why SEO best practices feel more unclear than ever Authentic content vs high-volume output, what wins with AI? Building trust: How to make your site feel real to your visitors Ads, paid influencers, evangelists: what actually pays off? Resources and Links from This Episode Lars on LinkedIn: https://www.linkedin.com/in/larslofgren/  Lars’ website and newsletter: https://larslofgren.com/  Lars on BlueSky: https://bsky.app/profile/larslofgren.bsky.social  Lars on Twitter/X: https://x.com/larslofgren?lang=en  Find me on Twit...
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2 weeks ago
53 minutes 5 seconds

Rogue Startups
RS347: How to Rank Any Brand In AI Results
Craig talks with This week on Rogue Startups, Craig chats with Mike Buckbee from Knowatoa about how AI is changing the game for brands. With tools like ChatGPT taking over the way we search and discover businesses, Mike breaks down what you need to do to get your brand noticed in the AI world. From content strategies to getting your site in front of the right eyes, this episode’s got the lowdown on how to stay ahead in an AI-driven world. Michael is a serial entrepreneur and software developer who has founded multiple successful startups in the cybersecurity space. With over a decade of experience in marketing and technology, he previously worked as a Director of Demand Generation for a public cybersecurity company, as well as consulting for multiple YC startups. Knowatoa’s mission is to help businesses win the AI search game by ensuring they remain discoverable, relevant, and competitive in a rapidly evolving digital landscape. Highlights from Craig and Mike’s conversation: How to get your business in front of customers in the AI-driven world New strategies for success: creating brand-specific content that attracts customers What "Face vs Space" content really means Where AI is training and how it impacts businesses The role of txt: Is it still important, and what’s the best alternative? Why you should ask ChatGPT questions about your business Personalized AI search results: Are they working for or against you? Why your content should be on YouTube, LinkedIn, and Reddit The growing role of LLMs in social etiquette and advice How search, companionship, and advice are blending in the AI space What does all this mean for businesses in the future? The future of business is pay-to-play Will AI take 30% of our jobs? The "floor" may rise, but the "ceiling" will stay human   Resources and Links from This Episode Knowatoa: https://knowatoa.com/ Mike on LinkedIn: https://www.linkedin.com/in/michaelbuckbee Email: Mike@knowatoa.com If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com
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3 weeks ago
47 minutes 34 seconds

Rogue Startups
RS346: What 11 Years in SaaS Really Looks Like
In this episode of the podcast, Craig sits down with longtime entrepreneur Colin Bartlett, cofounder of StatusGator, to explore what it really takes to build, and sustain, a SaaS business over the long haul. With more than a decade at the helm of a company that helps users monitor service outages, Colin shares hard-won insights from 12 years of entrepreneurship and 11 years of running StatusGator. The conversation dives into how founders’ perspectives evolve, especially in today’s turbulent tech landscape, and how to stay grounded and successful through all of that craziness. Highlights from Craig and Colin’s conversation: How Colin and StatusGator did when Google Cloud went down for a few hours The factors that can determine whether or not free trials can work for your business The difference between the company in the beginning versus 10+ years down the road How their businesses fit into the current markets (alongside AI and other tech advances) Appreciation and respect for the businesses in such uncertainty Plans, trajectories, and what the future holds for them Views on profit in the SaaS industry Their team structures and how to hire and maintain a team in the AI era Staying fresh in the market after you’ve been in the business for a while The benefits of having a cofounder SOC 2 (System and Organization Controls 2) compliance and privacy standards How many hours does your team have to work to be a value to your company?   Resources and Links from This Episode Colin Bartlett on LinkedIn: https://www.linkedin.com/in/colinabartlett/ StatusGator: https://statusgator.com/ If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com  
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1 month ago
48 minutes 49 seconds

Rogue Startups
RS345: The State Of Search 2025
- LLMs.txt article: https://www.quoleady.com/llm-txt-files/ - Craig's YouTube channel: https://youtube.com/@thecraighewitt  
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1 month ago
18 minutes 27 seconds

Rogue Startups
RS344: 12 Years to Overnight Success with Amar Ghose
What does it really take to lead a company for over a decade—and still be growing? In this episode, Craig chats with Amar Ghose, founder and longtime CEO of ZenMaid, about the challenges, lessons, and evolution that come from running a SaaS company for 12 years. From market leadership and internal conflict to personal growth and productivity, Amar shares candid insights into the realities of long-term entrepreneurship. Whether you're scaling a startup, feeling stagnant in your leadership role, or just wondering if AI is going to eat your SaaS lunch, this conversation delivers.   Highlights from Craig and Amar's conversation: Transitioning from following trends to becoming a category leader Navigating internal disagreements and managing tough decisions Running a "benevolent dictatorship"—and why that sometimes works How to deal with boredom, complacency, and staying sharp as a CEO The productivity paradox: what being "productive" means at the top Entertainment vs. distraction: protecting your focus How coaching reveals your blind spots (and helps you evolve) Staying out of cruise control—how to keep leveling up, year after year Is AI a threat to SaaS companies, or a tool for growth? Takeaways and Vision Longevity in SaaS isn’t about coasting. It’s about evolving. Amar Ghose proves that staying in the game for 12+ years means embracing discomfort, sharpening your focus, and leading with intention. Whether you're one year in or a decade deep, this episode is a reminder: real leadership isn’t about avoiding boredom, it’s about leveling up through it. Resources and Links from This Episode ZenMaid – Amar’s SaaS for maid service businesses Follow Amar on LinkedIn Rogue Startups Podcast Archive Connect with Craig on Twitter/X: @TheCraigHewitt If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes.  Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me:
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2 months ago
47 minutes 27 seconds

Rogue Startups
A Caffeine Infused Diatribe
Hello, remember me?  Sorry that it's been 6 weeks, but I'm back. In this episode I talk through what I've been up to recently, what's going on with Castos, with myself personally, and things I'm learning growing the business.  Towards the end, I share the lessons I learned from a recent 2-day Scaling Workshop with Alex and Leila Hormozi.  The event was great, and really reframed how I am thinking about the business, and about being a business owner.   My YouTube channel: https://youtube.com/@thecraighewitt - for sales, marketing, and founder-focused content like this.
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2 months ago
46 minutes 59 seconds

Rogue Startups
RS342: SaaS Survival Mode - AI, Niches & Navigating Chaos
In this episode of Rogue Startups, Craig chats with Jesse Hanley, marketer, self-taught developer, and founder of Bento, a powerful email marketing platform for modern teams. With today’s economy in flux and global events adding more pressure, Craig and Jesse dive into what it really means to run and grow a SaaS business in 2025. They explore how entrepreneurs can protect their businesses and families in turbulent times, why niching down is more important than ever (but only for some), and how AI is transforming both Bento and Craig’s own company, Castos. From global living experiences to making tough decisions about free tiers, this episode is packed with honest insights, practical advice, and a few spicy takes on the future of SaaS. Highlights from Craig and Jesse’s conversation: Living and working in Japan, France, Australia, and the US: cultural and business differences Bento’s vision and how they are navigating economic uncertainty Knowing when to bring in experts (and when to trust your gut) How Bento is integrating AI—and how it’s driving real results for users Behind the scenes at Castos: using AI to boost productivity and creativity Are free plans a growth hack or a trap for SaaS companies? Marketing smarter: finding your ideal customers in a crowded market To niche or not to niche? What to do if your product is a Swiss Army knife If you’re a SaaS founder, bootstrapped entrepreneur, or just love behind-the-scenes looks at real businesses navigating real challenges, this episode is for you. Resources and Links from This Episode Jesse Hanley on Twitter/X: https://x.com/jessethanley  Bento: https://bentonow.com/  If you feel like Rogue Startups has benefited you, and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes.  Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn:
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3 months ago
45 minutes 12 seconds

Rogue Startups
RS341: Microconf 2025 Recap
Craig recaps his biggest takeaways from MicroConf 2025, reflecting on lessons in positioning, lead generation, conference ROI, and the power of going all in on what’s working. From tactical marketing insights to personal reflections, this episode delivers both strategic clarity and founder fuel.
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4 months ago
17 minutes 48 seconds

Rogue Startups
RS340: Is AI Killing SaaS w/ Tim Schumacher
In this episode of Rogue Startups, Craig sits down with founder and entrepreneur Tim Schumacher to discuss his insights on AI, the future of SaaS, and what makes a company successful. In 2001, Tim co-founded Sedo.com, the world's largest domain marketplace. Since selling the company, he’s been active as an Entrepreneur and/or Investor in various start-ups, such as Eyeo (makers of Adblock Plus), Ecosia, Hitfox, Aklamio, Miomente, PiwikPro, BasicThinking, Home, Zolar, Joblift, SaaS.group, and others.  Highlights from Craig and Tim’s conversation: The future of SaaS keeps founders up at night Using artificial intelligence to analyze feedback and company metrics for smarter decision-making How to make your data, and your customers' data, available across multiple platforms and environments What impact will AI and automation have on the economy and the future of work? Why are some in the SaaS industry still hesitant to adopt AI, and what are their fears? Key factors that drive business growth and longevity. Product-Market Fit vs Founder-Market Fit: Understanding the difference and why both matter. Starting a business at the intersection between climate tech and AI Remote work vs in-office culture: How the workplace dynamic is evolving in the age of digital transformation. Resources and Links Mention in This Episode: Tim on Twitter/X Tim on LinkedIn Email: tim@saas.group Sedo Zenloop  Day.ai  Fyxer If you feel like Rogue Startups has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. Do you have any comments, questions, or topic ideas for future episodes? Feel free to reach out to me: Twitter: @TheCraigHewitt LinkedIn:
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4 months ago
43 minutes

Rogue Startups
RS339: AI Skeptic, or Believer
In today’s episode, Craig chats with Anthony Eden from DNSimple about how they use AI in their businesses and their personal lives. As early skeptics of AI, they do a deep dive into what made them change their minds, what AI does for them, and how it might actually be holding people back. Like the internet, AI is a powerful tool people can use to make their lives better.  They also chat about what it’s like to raise kids as entrepreneurs. Has their influence improved or hindered their children’s lives? Not to mention, how do they balance their work life and personal life and is AI helping them with that balance? Anthony Eden is the creator and founder of DNSimple. He has been developing web applications since the early days of the web (1995) using Ruby, Erlang, Golang, and other languages. He used to publish a podcast called the Strong Businesses Podcast with Steven Bristol. He also published a mostly weekly podcast of progressive dance music over at theministerprime.com. He also produces tracks which can be found on SoundCloud. Highlights from Craig and Anthony’s conversation: What changed Anthony and Craig’s minds about AI How to, as an entrepreneur, leverage AI without just “chasing the trend” The personal and emotional impacts of running a business in this AI world What AI will do for the future of business and SaaS Training AI and what the “mistakes” teach you and your team “I have to have a little bit of fear in everything I do [as a founder].” Keeping customer data safe and secure What data is AI using to aid you with your business? “This kind of stuff is fantastic but, boy, does it make you lazy.” As an entrepreneur, how do you talk to your kids about careers after college? How is generative AI going to make our lives better? Takeaways and Vision: How do you take a non-native AI solution and adapt it to a solution for your customers, your team, and your business? As a founder and entrepreneur, how you use AI in your business is important. Not only do you have to pay attention to what information you are getting from AI, but how it is affecting your productivity overall.  Resources and Links from This Episode: DNSimple Anthony Eden, LinkedIn Anthony Eden,
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5 months ago
47 minutes 49 seconds

Rogue Startups
RS338: Balancing Your Use of AI with Aaron Francis
Ever wonder what's happening behind the scenes when your dev team says they're "leveraging AI"? As a non-technical founder, you don't need to understand every line of code, but knowing how AI is actually being used in your business is becoming essential. Today I'm sitting down with Aaron Francis, who pulls back the curtain on AI in development work. We'll explore the surprising differences between how veterans and newcomers in the field are using these tools, the common pitfalls teams fall into, and the unexpected ways AI is transforming how products get built. Whether you're trying to speak your developer's language or just want to ensure your company is using AI effectively, this conversation will give you the insights you need.   Highlights from this Episode: Are junior developers utilizing AI too much? Creating a balance between overusing AI and being a Luddite How Aaron uses Claude for “discrete” tasks Developers aren’t going away anytime soon Balancing the use of AI without depending too much on it Harnessing the power of AI for your business AI tools are both calming and scary for founders Aaron’s different uses for 01 Pro What AI can do versus what AI should do and undeniably human tasks Where to go to educate yourself about AI The importance of testing and checking AI work   Resources and Links from this Episode: Try Hard Studios: https://tryhardstudios.com/ Aaron Francis: https://x.com/aarondfrancis Reforge: https://www.reforge.com/profiles/brian-balfour SWYX: https://x.com/swyx https://www.youtube.com/@JeffSu https://www.youtube.com/@SkillLeapAI https://www.youtube.com/@MATGpod Email me: podcast@roguestartups.com Find me on Twitter:  https://twitter.com/TheCraigHewitt
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5 months ago
52 minutes 12 seconds

Rogue Startups
RS337: Building AI Native SaaS w/ Jordan Gal
Today, Craig chats with Jordan Gal from Rosie about starting a business centered solely on AI. While many of us use AI to help with our work tasks and streamline certain jobs, Jordan’s whole business is AI. They discuss how you and your customers can use AI, what it’s like to start a company right now, and what AI is doing to SaaS. Rosie creates a new option for small businesses. Previously, the only way to handle phone calls during work hours was through voicemail or an answering service. Rosie offers a new option in that market: an AI can answer the phone for you and handle the tasks needed for these calls, whether it’s taking messages, sending messages out, or talking to clients. Highlights from Craig and Jordan’s conversation: Non-technical CEOs sympathize more with customers Jordan views his engineering company as customers see their product Because of this, he knows how Rosie helps businesses run better Using AI to help the customer understand their data vs building a product that was not possible before AI Create milestones for the team when creating a brand-new product Jordan tells his team to work as if they are onboarding 100 customers a day Dealing with customers that have different knowledge bases of your type of product Remove marketing fluff to speak plainly to possible customers If you provide the customer with something they truly need and get value from, they will find ways to deal with those roadblocks Conversion versus usage numbers: how to avoid churn Freemium and usage-based trials What AI has done to SEO: people are led to video and YouTube Software in the AI era Now is a good time to bootstrap; it is not a good time to raise money Everything you do has to have leverage Takeaways and Vision: Everything in technology is time-sensitive because tech improves and evolves so fast. Rosie shows us that AI can do much more than just answer questions, run some numbers, and analyze data. Whether you’re using AI to help your business run better, or if you’re creating the next AI tool, now is the time to embrace this technology. Resources and Links from This Episode: Rosie   Jordan on Twitter/X
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6 months ago
48 minutes 6 seconds

Rogue Startups
RS336: Claude Project Deep Dive with Alison French
On today’s episode of Rogue Startups, Craig continues his AI series with founder, marketer, and Claude-user Alison French. They discuss the hesitation creators feel when working alongside AI and what Alison did to overcome that hurdle. Since then, she’s taught herself how to use Claude.ai in her creative and professional work. AI is a tool that everyone has to learn how to use.  Watch on YouTube If you feel our podcast has benefited you and might benefit someone else, please share it with them. Also, if you have a chance, please give Rogue Startups a review on iTunes. We’ll see you next week! Highlights from Craig and Alison’s conversation: How creatives can use AI to improve their professional and personal lives How to fine-tune Claude’s tone of voice: Add files to the specific project only You have to feed the machine with information that matters Over time, working within the same project, Claude will tune itself to your prompts How to have Claude see references and change the tone or voice Separate and break down transcripts by prompt to hone in on specifics Claude is like a junior copywriter: work with it and nurture it, and it will help your work go faster so you can focus on the important things. Craig’s creative process when creating content: Get examples/models, templates, and ideas to input into your AI program of choice. Break your content up into different functions. Go in once a week to pull out topics. Put the time and energy into refining one meaty piece of content that you can use over and over again. You have to focus on what makes you credible to your audience How does your team embrace and respond to AI because at the surface it’s a risk for all of us? How do we educate our youth now, for a future with AI? Takeaways and Vision Balancing the importance of human connection with the ability to express your individuality and be yourself is even more possible in this AI era. Adopting and embracing technology and AI in your personal and professional lives can help save you time and free up some creative energy for being social, innovative, and expressing yourself. AI will give you the time to do the work to open yourself up to having personal experiences. Resources and Links from This Episode   Alison French on LinkedIn: https://www.linkedin.com/in/frenchalison/  LTO:
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6 months ago
47 minutes 43 seconds

Rogue Startups
RS335: Evaluating AI Model Performance with Stuart Grey
In today’s episode of Rogue Startups, Craig sits down with AI expert Dr. Stuart Grey to discuss how AI is transforming both his personal and professional life. Dr. Grey also shares how he educates his students and clients on AI applications. He believes AI will play a pivotal role in all of our futures, and while there may be hesitations, AI can be harnessed to create high-quality content and drive innovation.   Watch on YouTube Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work. Highlights from Craig and Stuart’s conversation: What it’s like to teach AI and machine learning at the university level Comparing AI prompts across different platforms and analyzing results Stuart’s AI Rules of Thumb for efficient content generation Ethical considerations when using AI technologies A glimpse into the near future of AI in everyday life and business The two primary types of AI-driven content creation How to turn basic AI-generated content into exceptional material Takeaways and Vision AI is integrating into our daily lives and everyone needs to learn how to leverage this powerful technology to save time and enhance productivity. Whether you’re just starting or an established professional, understanding how to work alongside AI-powered tools is key to staying ahead in your career. Resources and Links from This Episode Stuart Grey on LinkedIn: https://www.linkedin.com/in/stuartgrey/  Stuart Grey on X: https://x.com/stugrey  Stuart Grey’s website: https://www.stugrey.com/  Castos Free Tools: castos.com/tools Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt Want to Share Your AI Story? I’m looking for guests to share how they’re using AI in their businesses. If you’ve got some great examples or unique insights, reach out to me:
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6 months ago
47 minutes 6 seconds

Rogue Startups
RS334: How AI Saves Me 10 Hours A Week
Today, I’m kicking off a series on AI—how I’m using it personally and professionally to grow my business, make life easier, and operate at a higher level. Over the next few episodes, I’ll be chatting with folks about the real ways they’re using AI in their businesses. If you’re interested in joining the conversation, hit me up (details below). But for now, here’s a breakdown of how I’m incorporating AI into my own work. Key Ways I’m Using AI in My Business Content Creation for Programmatic SEO Using OpenAI and Claude to create use case pages for Castos. Built a process to programmatically generate 100+ SEO landing pages using Google Sheets and templates. Example use case: Why Startups Should Start a Podcast for Thought Leadership. Custom GPT for YouTube Scripts Created a custom GPT workflow to script our Castos YouTube videos. Process: Provide a topic, feed it examples, and let GPT draft outlines and scripts. Outcome: High-performing, 90%-ready scripts I tweak and personalize. Building Free Marketing Tools Leveraging tools like Replit and Cursor to develop free tools for Castos (e.g., podcast name generator, social post creator). Focus: Engineering as marketing to drive traffic and lead generation. Documenting Internal Processes Using Loom to record workflows (e.g., triaging support tickets). Leveraging AI to convert videos into detailed step-by-step process documentation (aka playbooks). Automating Low-Level Tasks (Future Plans) Exploring tools like Make and Airtable for automating repetitive processes (e.g., email tagging, Slack notifications). Goal: Free up mental energy for high-value activities like sales, marketing, and strategy. Takeaways and Vision AI is transforming the way we work, and I’m all in on finding ways to integrate it into every aspect of my business. It’s not just about saving time; it’s about leveling up and creating systems that make the impossible possible. I’m inspired by the idea of building something like an 8-person, $10M business with AI at its core. That’s where I’m headed—and I want to bring you along. Resources and Links from This Episode Castos Free Tools: castos.com/tools VidIQ (for YouTube insights): vidiq.com Replit (for building free tools): replit.com Cursor (for coding support): cursor.com Loom (for recording processes): loom.com Email me: podcast@roguestartups.com Find me on Twitter: @TheCraigHewitt Want to Share Your AI Story? I’m looking for guests to share how they’re using AI in their businesses. If you’ve got some great examples or unique insights, reach out to me: Twitter: @TheCraigHewitt LinkedIn: Craig Hewitt Email: podcast@roguestartups.com Let’s level up together!
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6 months ago
15 minutes 51 seconds

Rogue Startups
RS333: Grading My Business (and yours!)
In this New Year's Eve 2024 episode, we dive into a framework for evaluating SaaS businesses across eight crucial criteria. Instead of doing a typical year-in-review or making predictions, we explore how to assess the fundamental strength and potential of your business. Episode Highlights Craig grades Castos (podcast hosting platform) across eight key criteria for evaluating SaaS businesses: 1. Pricing (6/10)- Core product (podcast hosting) averages $28/month - below ideal $50+ threshold- Production services start at $1,500/month- Enterprise clients pay tens of thousands annually- Mixed pricing model affects overall score 2. Churn (9/10)- Extremely low churn rate- Attributes success to: - WordPress integration- Premium pricing (no free tier) - Strong technical reliability 3. Payment Processing Integration (4/10)- Offers multiple monetization options: - Castos Ads - Castos Commerce - Donations - Paid subscriptions - Private podcasting- Limited adoption of direct monetization features- Most customers monetize indirectly through business growth 4. Switching Costs (6/10)- Technically easy to switch providers- High retention due to ongoing necessity- Perceived switching cost higher than actual 5. Technical Advantages- WordPress integration provides unique value- Core functionality similar to competitors- Important lesson: Customer needs often simpler than assumed 6. Expansion Revenue (3/10)- Limited expansion opportunities- Most customers stay at $19/month- Working to add upgrade opportunities- Identified as major growth limitation 7. Established Market Need (10/10)- Clear market position- Well-understood service category- Strong product-market fit 8. Customer Acquisition (6/10)- Success with content marketing, SEO, partnerships- Struggling with paid acquisition- Limited by low price point- Working on improving paid channels Key Takeaways - Overall Business Grade: B (maybe 80/100)- Growth Ceiling: Business could potentially double but unlikely to become a $50M/year company- Main Limitations: - Low initial price point ($19/month for most customers) - Limited expansion revenue - Restricted marketing channels due to unit economics Looking Forward Future episodes will mix personal insights about founding and running a business with interviews featuring successful founders.
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7 months ago
22 minutes 3 seconds

Rogue Startups
RS332: Competing with Stripe and Hubspot (ft. Geoff Roberts)
Hey everyone! Just had an awesome chat with Geoff Roberts from Outseta (outseta.com). They're doing something pretty wild - basically smashing together Stripe and HubSpot into one platform for subscription businesses. How cool is that? Quick Hits:- Outseta is an all-in-one platform handling payments, auth, CRM, email, and help desk- They've got this unique setup where everyone makes $210k/year (pro-rated) and can work 1-5 days a week- Took them 4 years to really nail the product (hey, good things take time!) Best Parts of the Convo:- Jeff got real about marketing struggles (who hasn't been there?)- Turns out ChatGPT is actually sending them customers now - wild!- We had a great debate about whether SaaS is still the golden ticket (spoiler: it's way more competitive now)- Talked about why sometimes it's better to stick with a "pretty good" business than chase the next unicorn Where They're Headed:- Aiming for $10M in revenue with a lean team of about 20 people- Shifting from being super product-focused to really pushing growth- Geoff's been at it for 8 years and plans to keep going for 7 more Real talk: This episode is perfect if you're building a SaaS company or thinking about bundling multiple tools together. Geoff drops some serious knowledge about what it's actually like in the trenches. Check them out at outseta.com if you want to see what they're building! #SaaS #Startups #Entrepreneurship
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7 months ago
39 minutes 14 seconds

Rogue Startups
RS331: I'm Still Here...
After a 2+ month hiatus, we're back!  Watch on YouTube Sorry for the pause in episodes, but thank you for tuning in this week.  In this episode I talk through why the forever long break in the podcast, what I've learned in that time, and where things are with me and the business. But most of all, I want to hear from you...what do you want out of this podcast. Hit me up on Twitter, LinkedIn or even Bluesky
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7 months ago
9 minutes 23 seconds

Rogue Startups
RS330: Product-Led Playbook with Wes Bush
Wes Bush is a leading authority on product-led growth (PLG) and is here to guide Craig through the playbook for implementing product-led strategies in your business. This episode is invaluable for entrepreneurs eager to understand how product-led growth works, as well as those skeptical about its effectiveness. Listeners will gain insights into the product-led mindset and methodology that Wes employs for successful PLG implementation. Watch on YouTube Do you have any comments, questions, or topic ideas for future episodes? Send Craig an email at podcast@roguestartups.com. If you feel like our podcast has benefited you and it might benefit someone else, please share it with them. If you have a chance, give Rogue Startups a review on iTunes. We’ll see you next week! Highlights from Craig and Wes’ conversation: Differences and Similarities Between Product-Led Growth (PLG) and Self-Service SaaS How to Leverage PLG as a Marketing Tool Internal to External Growth Loops (e.g., Canva) Providing Value and Education to Empower Customers Overcoming the Fear of Change and Embracing Creative Destruction The Product-Led Implementation Program and Wes Bush’s New Book From Contender to Leader: Navigating Your Market Castos: A Case Study in Product-Led Growth A Little About Wes: Wes is an entrepreneur, author, and product-led coach. Over 500,000 people have read his Product-Led Growth book and listened to the ProductLed Podcast. Links & Mentions from This Episode: Wes on LinkedIn Product-Led “Why Nations Fail” by Daron Acemoglu and James A. Robinson Rogue Startups Resources: Follow Craig on Twitter/X Craig on LinkedIn Castos Founder Insights
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10 months ago
47 minutes 52 seconds

Rogue Startups
How To Hire For Growth
In this episode of Rogue Startups, I dug into several pressing questions from the community. From knowing when to pull the plug on a marketing channel to the debate around hiring for support versus sales, we covered ground that matters deeply to founders and entrepreneurs. Here’s a breakdown of the key takeaways that can help you level up your startup game. Watch on YouTube 1. When Should You Know if a Channel is Working? A common dilemma many founders face is determining whether a new marketing channel is working. If you’ve ever wondered how long you should invest in a channel before calling it quits, you’re not alone. Here’s how I break it down: Give New Channels at Least 90 Days: If you’re starting fresh with a channel, 90 days is the minimum timeframe to give it. Less than that is almost never enough. Existing Channels Need Time Too: Even for established channels that you’re tweaking or optimizing, 90 days is still a good baseline. After that, look at the data to guide your decision. Focus on Leading Indicators: Whether it’s impressions on LinkedIn, open rates in email campaigns, or early engagement in SEO, you need to assess the leading metrics first. These are the earliest signs that a channel is gaining traction. For example, if you’re working on LinkedIn, impressions tell you whether your content is even being seen. Engagement and DM conversations are steps that follow, but focusing on what starts the funnel will help you decide if you should stick with it. 2. The Support, Success, or Sales Dilemma Another big question I often get asked is, “How do I know whether I need to hire for support, sales, or customer success?” This decision depends largely on where your business is in its growth stage and the roles you want to fill. Support Roles: These are typically more reactive—answering support tickets, maintaining a knowledge base, and troubleshooting. If customers are having common issues, or if onboarding is a bottleneck, it might be time to bring in a support team member. Success Roles: Customer success is more proactive. The goal here is to ensure customers get the most value from your product. This role could be key if your customers are signing up but not converting to paid users, or if you’re looking to drive expansion revenue. Sales Roles: Salespeople hunt for new business and close deals. If you’re looking to generate new demand or work with enterprise clients, this is the hire for you. Sales is more aggressive in its pursuit of growth, but if your inbound leads just need a quick demo, you may not need a dedicated salesperson—success could handle it. I suggest founders think about these roles in terms of function and their contribution to revenue growth. Where is the biggest gap in your customer journey? 3. Focus on Customers and Revenue-Generating Activities As entrepreneurs, it’s easy to get bogged down in tasks that feel productive but don’t directly drive growth. One of my favorite principles to live by is focusing on activities closest to your customers and revenue. Direct Conversations Over Complex Funnels: Fancy marketing automation systems might feel like progress, but especially early on, nothing beats direct customer conversations. Whether it’s cold outreach or calling people in your network, it’s the quickest way to gather real data and refine your approach. Avoid Procrastination vi...
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10 months ago
14 minutes 20 seconds

Rogue Startups
On Rogue Startups we share the journey of startup founders as they're growing their businesses. We feature experts in the fields of sales, marketing, and product development to hear how they're growth hacking their productized services and SaaS products. If you're on the journey of an entrepreneur then tune and hear how we're tackling some of the same obstacles you may be facing, and how we're winning in the game of business. Listeners of Startups for the Rest of Us, My First Million, Mixergy, and Bootstrapped Web will love checking out our show.