Rogue Startups

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

Jordan Gal, founder of Rosie, discusses launching an AI-driven service that revolutionizes phone call management for small businesses. He emphasizes the need for non-technical CEOs to understand their customer's perspective. The conversation covers using AI to enhance user experience, strategies to avoid churn, and the importance of clear communication. They also touch on onboarding practices and the dynamics of customer acquisition. Jordan highlights the company's focus on genuine customer needs and the shift towards simplicity in tech solutions.

Join Alison French, a founder and marketer who specializes in AI tools like Claude.ai, as she dives into using AI to boost creativity and efficiency. She shares her journey overcoming initial hesitations to embrace AI, emphasizing its role as a collaborative partner. Discover how to fine-tune Claude's tone to fit your projects and transform your content creation process. Alison also discusses the balance between technology and personal connection, highlighting the importance of nurturing creativity while streamlining workflows.

In this engaging discussion, Dr. Stuart Grey, an AI expert and university educator, shares his insights on the transformative power of AI in everyday life and business. He talks about the balance of teaching technical skills with critical thinking in engineering education. The episode dives into practical AI tools for content generation and the importance of ethical considerations. Grey also reveals his AI Rules of Thumb, and emphasizes the need for human oversight in an increasingly automated world.

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!

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.

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

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

Wes Bush, an entrepreneur and product-led coach, shares his insights on product-led growth (PLG) strategies. He explains how PLG differs from self-service SaaS and emphasizes it as a powerful marketing tool. Discussion includes overcoming skepticism, educating customers, and creating growth loops. Wes also talks about the importance of community support for user engagement and retention. Listeners can expect valuable guidance on navigating market challenges while implementing a product-led approach.

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 via Fancy Funnels: Instead of hiding behind digital funnels and automation, get out there and sell directly. Speak to potential customers, get their feedback, and learn what truly resonates. Remember, your goal in the early days is to collect data, not over-engineer things. 4. Simple Ways to Test Paid Acquisition Paid acquisition is often intimidating, but there’s a simple approach that’s often overlooked—sponsorships in industry newsletters, podcasts, or YouTube videos. This tactic is low-risk and can provide quick insights into whether your message resonates. Why Sponsorships Work: Instead of figuring out the complexities of Google Ads or Facebook Ads, consider sponsoring content that already has your target audience’s attention. Whether it’s a niche podcast or a popular industry newsletter, you can place your offer in front of a highly relevant audience without a huge commitment. Discreet and Affordable: Unlike ongoing paid ads, sponsorships can be a one-off or a short-term commitment. You can test the waters, see if it works, and then decide whether to scale up. At Castos, we’re experimenting with this approach by sponsoring a few relevant newsletters and YouTube videos in our space. It’s a great way to validate messaging and offers before diving into more complex ad platforms. 5. The Most Important Thing for Founders The core principle for any founder is this: Work on the thing closest to your customers and revenue. All the fancy tools, automation, and branding strategies can come later. Start by doing what doesn’t scale—talking directly to your customers, gathering insights, and refining your product and messaging based on real feedback. Final ThoughtsThese are some of the questions that have come up repeatedly in my coaching sessions and with fellow founders. My best advice is to stay close to your customers, be data-driven in your approach, and always remember the 90-day rule when evaluating new channels. If you have more questions or want to dive deeper into any of these topics, feel free to reach out! Call to Action: If you’re interested in growing your business and leveling up your marketing, stay tuned for our upcoming episode where I’ll be sharing a deep dive into building a paid acquisition funnel for higher-ticket products.