Startup to Last

Rick Lindquist and Tyler King
  • 5.0 (22)
  • ENTREPRENEURSHIP
  • UPDATED BIWEEKLY

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.

  1. 4D AGO

    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 2026 Rick 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 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 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 58m

  2. 12/04/2025

    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

    49 min

  3. 11/20/2025

    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.

    45 min

  4. 11/06/2025

    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.

    50 min

  5. 10/09/2025

    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.

    55 min

  6. 09/25/2025

    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.

    55 min

  7. 09/11/2025

    Website overhaul

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

    56 min

  8. 08/14/2025

    We're profitable, now what?

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

    54 min
See All (196)

5
out of 5
22 Ratings

About

Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.

Information

  • Creator
    Rick Lindquist and Tyler King
  • Years Active
    2019 - 2025
  • Episodes
    196
  • Rating
    Explicit
  • Copyright
    © Rick Lindquist and Tyler King
  • Show Website
    Startup to Last

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