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

Latest Episodes

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...

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.

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.

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.

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