Startup to Last

Do custom Notion agents really work? No, they don't!

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Soft launches Less Annoying CRM is soft launching two major features we’ve been...

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New positioning Of course we spend the first half of the episode talking about AI, but...

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

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2025 Recap This is our annual recap episode. We talk about how things went in 2025...

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Can Rick’s optimism defeat Tyler’s pessimism? In this episode, we once again talk about AI, and oh boy do we get off...

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Open Enrollment Woes In this episode, Tyler and Rick discuss the challenges faced by Leg Up...

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Does OG inbound marketing still work? In this episode, we talk about whether Rick’s expertise with traditional...

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ICP ICP ICP We spend the entire episode diving into how we can better define Less...

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What to do while you’re waiting for results In this episode, we talk about what the Less Annoying team should be...

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Website overhaul In this episode, we talk about how Rick can overhaul the LegUp Health...

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We're profitable, now what? In this episode, Rick shares how he approached thinking about what to do...

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Tiers, add-ons or standalone products? In this episode, we dive into where things stand with Less Annoying...

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User communities In this episode, we talk about trying to create a forum for Less...

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SIP trunks In this conversation, Rick and Tyler explore various topics ranging from...

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Add-on product In this conversation, Rick and Tyler discuss various topics ranging from...

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Will these guys please stop talking about AI In this conversation, Tyler and Rick discuss various topics ranging from...

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Acquisition vs Expansion In this conversation, Tyler and Rick discuss the challenges and...

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Vibe coding In this conversation, Tyler King shares his experiences as a new father...

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What do all these customers have in common? In this conversation, Tyler and Rick discuss various aspects of...

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Dipping a toe in the AI waters In this conversation, Tyler and Rick discuss the challenges and triumphs...

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Consultative sales In this episode, Tyler and Rick discuss various sales best practices,...

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Lowering the bar In this episode, we talk about how Rick has given himself some breathing...

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