All Episodes
Displaying 1 - 30 of 200 in total
Do custom Notion agents really work?
No, they don't!
Soft launches
Less Annoying CRM is soft launching two major features we’ve been working on for months. This episode dives into that and a bunch of other stuff.
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...
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.
Website overhaul
In this episode, we talk about how Rick can overhaul the LegUp Health website to fit their new positioning.
We're profitable, now what?
In this episode, Rick shares how he approached thinking about what to do with his first meaningful profit.
Tiers, add-ons or standalone products?
In this episode, we dive into where things stand with Less Annoying CRM’s potential new product.Here's the blog post about First Team Principles Rick mentioned.
User communities
In this episode, we talk about trying to create a forum for Less Annoying CRM’s users.
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 f...
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 integrat...
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 i...
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 be...
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 L...
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 ...
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, ...
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 enhan...
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.
Line go up
In this episode, we talk about some metrics that are headed in the right direction. Let’s go
Rating growth channels
In this episode, we try to prioritize some of the different growth channels Rick is considering for 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 t...
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.
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.
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.
Everybody’s marketing
We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying.