186 episodes since 2019

Startup to Last

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.

SIP trunks

In this conversation, Rick and Tyler explore various topics ranging from smoking techniques and the evolution of grilling methods to the challenges and benefits of a four-day work week. They discuss b...

Jul 04, 2025

Add-on product

In this conversation, Rick and Tyler discuss various topics ranging from their beverage preferences to the latest trends in podcasts, business growth, and the integration of AI in their operations. Th...

Jun 19, 2025

Will these guys please stop talking about AI

In this conversation, Tyler and Rick discuss various topics ranging from personal experiences with parenting and reading habits to business growth strategies and the integration of AI in their respect...

Jun 05, 2025

Acquisition vs Expansion

In this conversation, Tyler and Rick discuss the challenges and adjustments of parenthood, particularly Tyler's experience as a new father. They explore the balance between work and family life, the d...

May 22, 2025

Vibe coding

In this conversation, Tyler King shares his experiences as a new father while balancing work responsibilities. The discussion transitions into Tyler's recent work on LegUp Health, focusing on the chal...

Apr 25, 2025

What do all these customers have in common?

In this conversation, Tyler and Rick discuss various aspects of long-term product strategy at Less Annoying CRM, including personal updates, business growth, customer retention challenges, economic co...

Apr 10, 2025

Dipping a toe in the AI waters

In this conversation, Tyler and Rick discuss the challenges and triumphs of managing projects within SaaS companies, particularly focusing on the effective use of AI, sales pipeline dynamics, and the...

Mar 27, 2025

Consultative sales

In this episode, Tyler and Rick discuss various sales best practices, focusing on the importance of maintaining a clean sales pipeline, optimizing CRM usage, and enhancing marketing strategies. They d...

Mar 13, 2025

Lowering the bar

In this episode, we talk about how Rick has given himself some breathing room, and how that’s impacted his outlook on the business. 

Feb 20, 2025

Line go up

In this episode, we talk about some metrics that are headed in the right direction. Let’s go

Jan 16, 2025

Rating growth channels

In this episode, we try to prioritize some of the different growth channels Rick is considering for 2025.

Jan 02, 2025

2024 Recap

In this episode, we recap 2024 and set goals for 2025:Personal goals for 2025:Rick: Primary theme: Buy back timeTake 1 personal day every 1-2 monthsGet time back for things I love (skiing, basketball,...

Dec 19, 2024

Different types of hiring

In this episode, we discuss how there are multiple different approaches to take when a startup needs to grow the team.

Dec 05, 2024

Bluesky is back

In this episode, we discuss Bluesky as the new Twitter, how Rick’s busiest time of year is surprisingly calm, and more.

Nov 21, 2024

How we know if a feature is ambitious enough

Less Annoying CRM is working on some big features, and in this episode, we discuss what we’re learning as a result.

Nov 07, 2024
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