Startup to Last

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 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 Syd Finalize will+trust Stretch goal: Start vibe coding personal apps Professional goals for 2026 Rick (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 doing Try to grow LegUp Health by 50%, but do it in a way that we are all excited about Rebuild personal website + read 10 really, really good nonfiction books and publish notes on them Experiment with AI to generate 1 additional revenue stream Tyler 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-sustaining Product management/design: Figure out how to keep up with the devs (especially if AI allows them to move even faster) Product Ship Mobile and Kanban Reduce support by making things more self-serve Main theme: The first 30 minutes Onboarding improvements Rebuild the importing flow Simplification Separate contacts and companies Open contacts in page dialog Statuses on the contact record Table view of contacts

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 traffic and marketing strategies as they adapt to changing consumer needs.

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, 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.

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. Takeaways Tyler 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.