Startup to Last

As if Claude, Claude Cowork, and Claude Code weren’t enough, today we talk about Claude Design which is a completely different thing.

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.

In this episode, we dive into one of the most exciting topics imaginable: HIPAA compliance

In this episode, we dive deep into Less Annoying CRM’s new marketing strategy.

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.

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.

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.

No, they don't!

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.

Of course we spend the first half of the episode talking about AI, but then we get into some good ol’ fashioned SaaS talk.

In this episode, we talk about the only thing anyone is talking about right now: Claude Code.

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 2026 Rick  Getting back to basics Going 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 foolish Tyler  Handle the transition back to full-time work (as...

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

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 tra...

In this episode, we talk about whether Rick’s expertise with traditional inbound marketing will work for LegUp Health.

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.

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.

In this episode, we talk about how Rick can overhaul the LegUp Health website to fit their new positioning.

In this episode, Rick shares how he approached thinking about what to do with his first meaningful profit.

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.

In this episode, we talk about trying to create a forum for Less Annoying CRM’s users.

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...

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 n...

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 als...

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...