• Can Rick’s optimism defeat Tyler’s pessimism?
    Dec 4 2025

    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

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    49 mins
  • Open Enrollment Woes
    Nov 20 2025

    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.

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    45 mins
  • Does OG inbound marketing still work?
    Nov 6 2025

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

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    50 mins
  • ICP ICP ICP
    Oct 9 2025

    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.

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    55 mins
  • What to do while you’re waiting for results
    Sep 25 2025

    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.

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    55 mins
  • Website overhaul
    Sep 11 2025

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

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    56 mins
  • We're profitable, now what?
    Aug 14 2025

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

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    54 mins
  • Tiers, add-ons or standalone products?
    Jul 31 2025

    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.

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    57 mins