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Recent episodes
Correcting AI when it gets something wrong
Jun 18, 2026
41m 49s
HIPAA
Jun 4, 2026
51m 35s
It’s a Tyler episode
May 19, 2026
47m 46s
Where do the humans fit in?
Apr 23, 2026
54m 56s
Where to host a marketing site in the age of AI
Apr 9, 2026
50m 50s
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| Date | Episode | Description | Length | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 6/18/26 | Correcting AI when it gets something wrong | In this episode, we talk about using AI to answer questions based on content in a knowledge base. It’s easy to get a proof of concept working, but how do you continuously improve it from there? Is that even realistic with current technology? All that and more. | 41m 49s | ||||||
| 6/4/26 | HIPAA | In this episode, we dive into one of the most exciting topics imaginable: HIPAA compliance | 51m 35s | ||||||
| 5/19/26 | It’s a Tyler episode | In this episode, we dive deep into Less Annoying CRM’s new marketing strategy. | 47m 46s | ||||||
| 4/23/26 | Where do the humans fit in? | In this episode, we talk about how one of the new business challenges is to figure out what skills are uniquely human, and leaning into those things as your differentiator. | 54m 56s | ||||||
| 4/9/26 | Where to host a marketing site in the age of AI | In this episode, we talk about whether tools like Webflow still make sense to use when AI can generate professional looking marketing sites for you. | 50m 50s | ||||||
| 3/27/26 | How much to invest in growth | In this episode, we talk about how Rick has changed LegUp Health’s formula that decides how much money is available to invest in growth. | 51m 42s | ||||||
| 3/12/26 | Do custom Notion agents really work? | No, they don't! | 53m 25s | ||||||
| 2/27/26 | Soft launches | Less Annoying CRM is soft launching two major features we’ve been working on for months. This episode dives into that and a bunch of other stuff. | 51m 29s | ||||||
| 2/12/26 | New positioning | Of course we spend the first half of the episode talking about AI, but then we get into some good ol’ fashioned SaaS talk. | 54m 10s | ||||||
| 1/15/26 | Obligatory Claude Code episode | In this episode, we talk about the only thing anyone is talking about right now: Claude Code. | 48m 59s | ||||||
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| 12/31/25 | 2025 Recap | This is our annual recap episode. We talk about how things went in 2025 and what we’re hoping to see in 2026.Personal goals for 2026Rick Getting back to basicsGoing from reactive to proactive (and surviving to thriving)Shifting from a strategy of playing it safe and reducing risk to taking smart risk and being ok looking a little foolishTyler Handle the transition back to full-time work (as it impacts parenting)Find clarity on what level of wealth we’re comfortable exposing our daughter to.Help Shelly find more ways to go out at night while I take care of SydFinalize will+trustStretch goal: Start vibe coding personal appsProfessional goals for 2026Rick (hopes to achieve at least two of these goals) Outsource, delegate, or automate recurring tasks that I no longer value doing and/or others don’t value me doingTry to grow LegUp Health by 50%, but do it in a way that we are all excited aboutRebuild personal website + read 10 really, really good nonfiction books and publish notes on themExperiment with AI to generate 1 additional revenue streamTyler Spend almost all IC time on design, product management, and coding. Fewer distractions!Management: Get the team up to speed on AI, and make it self-sustainingProduct management/design: Figure out how to keep up with the devs (especially if AI allows them to move even faster)Product Ship Mobile and KanbanReduce support by making things more self-serveMain theme: The first 30 minutes Onboarding improvementsRebuild the importing flowSimplification Separate contacts and companiesOpen contacts in page dialogStatuses on the contact recordTable view of contacts | 1h 57m 30s | ||||||
| 12/4/25 | Can Rick’s optimism defeat Tyler’s pessimism? | In this episode, we once again talk about AI, and oh boy do we get off topic.Here's the AI tool Rick mentioned for recording your screen (we'll talk about that in a future episode)Here's the AI report Rick mentioned | 49m 14s | ||||||
| 11/20/25 | Open Enrollment Woes | In this episode, Tyler and Rick discuss the challenges faced by Leg Up Health during open enrollment, including issues with email communication and the impact of AI on consumer behavior. They explore the current health insurance landscape, the importance of product strategy and customer experience, and the role of content in engaging customers. The conversation also touches on shifts in search traffic and marketing strategies as they adapt to changing consumer needs. | 44m 50s | ||||||
| 11/6/25 | Does OG inbound marketing still work? | In this episode, we talk about whether Rick’s expertise with traditional inbound marketing will work for LegUp Health. | 49m 59s | ||||||
| 10/9/25 | ICP ICP ICP | We spend the entire episode diving into how we can better define Less Annoying CRM’s ideal customer profile, and what that would mean for the product and marketing. | 54m 51s | ||||||
| 9/25/25 | What to do while you’re waiting for results | In this episode, we talk about what the Less Annoying team should be working on while waiting to see if the last bet actually pays off. | 54m 46s | ||||||
| 9/11/25 | Website overhaul | In this episode, we talk about how Rick can overhaul the LegUp Health website to fit their new positioning. | 56m 29s | ||||||
| 8/14/25 | We're profitable, now what? | In this episode, Rick shares how he approached thinking about what to do with his first meaningful profit. | 53m 36s | ||||||
| 7/31/25 | Tiers, add-ons or standalone products? | In this episode, we dive into where things stand with Less Annoying CRM’s potential new product.Here's the blog post about First Team Principles Rick mentioned. | 57m 06s | ||||||
| 7/17/25 | User communities | In this episode, we talk about trying to create a forum for Less Annoying CRM’s users. | 53m 13s | ||||||
| 7/4/25 | SIP trunks | In this conversation, Rick and Tyler explore various topics ranging from smoking techniques and the evolution of grilling methods to the challenges and benefits of a four-day work week. They discuss business growth strategies, particularly focusing on customer retention and the importance of securing renewals. The conversation shifts to the technical aspects of VoIP systems, including SIP trunking, and the implications of AI on search optimization. Finally, they delve into potential new product opportunities and the strategic considerations of acquiring existing products to enhance their offerings. | 48m 04s | ||||||
| 6/19/25 | Add-on product | In this conversation, Rick and Tyler discuss various topics ranging from their beverage preferences to the latest trends in podcasts, business growth, and the integration of AI in their operations. They explore the significance of setting revenue goals, the role of AI agents in customer outreach, and the development of internal tools to enhance efficiency. Additionally, they delve into potential new product opportunities, customer feedback, and pricing strategies for future offerings, concluding with reflections on their business direction.TakeawaysTyler prefers soda over coffee for his morning routine.Rick has re-engaged with podcasts, discovering new content.Leg Up Health achieved a record revenue month, nearing their goal.Setting realistic revenue goals can provide relief and stability.AI integration is becoming crucial for business operations.Internal tools can significantly improve team efficiency.Customer feedback is essential for product development.Pricing strategies need careful consideration for new offerings.Exploring new product opportunities can enhance revenue per user.Authenticity in customer outreach is vital for engagement. | 54m 28s | ||||||
| 6/5/25 | Will these guys please stop talking about AI | In this conversation, Tyler and Rick discuss various topics ranging from personal experiences with parenting and reading habits to business growth strategies and the integration of AI in their respective companies. They explore the challenges of managing growth, the importance of understanding customer needs, and the potential of AI to enhance efficiency and customer experience. The discussion also touches on the significance of vertical integration and the future of AI in business, emphasizing the need for companies to be prepared for technological advancements while maintaining a focus on customer service.Chapters00:00 Parenting and Sleep Challenges03:29 Reading Habits and Fantasy Literature06:32 Business Growth and Revenue Updates09:21 Form Metrics and Marketing Strategies12:17 Internal Use Cases and New Features15:23 Exploring Industry-Specific CRM Opportunities21:22 Future of CRM and Industry Integration28:57 Navigating Software Integration Challenges32:34 The AI Dilemma: To Adopt or Not?37:13 AI Readiness: Preparing for the Future39:38 Revenue Metrics and AI Efficiency50:28 Exploring AI Opportunities in Customer Experience | 54m 47s | ||||||
| 5/22/25 | Acquisition vs Expansion | In this conversation, Tyler and Rick discuss the challenges and adjustments of parenthood, particularly Tyler's experience as a new father. They explore the balance between work and family life, the dynamics of business growth, and the implications of freemium models in their respective companies. The discussion delves into the importance of customer retention versus acquisition, the value of free users, and the efficiency required in service-heavy business models. Throughout the conversation, they share insights on navigating these complexities while maintaining a focus on long-term success. In this conversation, Tyler King and Rick discuss various topics including the implications of free trials on conversion rates, the integration of AI in coding practices with tools like Cursor, and the evolving landscape of client retention and revenue trends. They also delve into the recent changes in Apple's App Store pricing policies and their impact on developers, as well as the importance of understanding customer segmentation in business strategy. | 52m 48s | ||||||
| 4/26/25 | Vibe coding | In this conversation, Tyler King shares his experiences as a new father while balancing work responsibilities. The discussion transitions into Tyler's recent work on LegUp Health, focusing on the challenges and opportunities in building a health insurance platform. They explore the concept of 'vibe coding' and how AI is reshaping software development and content creation. The conversation concludes with a brainstorming session on packaging benefits for LegUp Health, emphasizing the importance of clear communication and demonstrating value to potential clients.TakeawaysFatherhood brings unexpected challenges and joys.Work-life balance is crucial for new parents.Fundraising milestones can be a time for reflection.Vibe coding allows for rapid development with AI assistance.AI can enhance productivity but may lead to fragility in code.Clear communication is key in demonstrating value to clients.Packaging benefits effectively can unlock new opportunities.Understanding the market is essential for product success.AI tools can streamline content creation processes.The future of work may require new skills and adaptability.Chapters00:00 The Journey of Fatherhood03:16 Navigating Work-Life Balance06:21 Milestones in Professional Growth09:09 The Dynamics of Startups12:11 Innovations in Health Tech15:20 Vibe Coding and AI in Development18:19 The Future of Software Development21:11 Content Creation with AI25:43 Navigating the AI Landscape32:56 The Future of Learning in an AI World37:26 Innovating Benefit Programs49:06 Packaging Value in Health Benefits | 57m 25s | ||||||
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