Startup to Last

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.