Welcome to Startup to Last, a podcast about building profitable software businesses that are meant to last.

Latest Episodes

New positioning

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

Obligatory Claude Code episode

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

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 2026Rick Getting back to basicsGoing fr...

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 fu...

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...

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