User communities
In this episode, we talk about trying to create a forum for Less Annoying CRM’s users.
Jul 17, 2025•53 min•Ep. 186
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.
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Episodes
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 business growth strategies, particularly focusing on customer retention and the importance of securing renewals. The conversation shifts to the technical aspects of VoIP systems, including SIP trunking, and the implications of AI on search optimization. Finally, they delve into potential new product ...
Jul 04, 2025•48 min•Ep. 185
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. They explore the significance of setting revenue goals, the role of AI agents in customer outreach, and the development of internal tools to enhance efficiency. Additionally, they delve into potential new product opportunities, customer feedback, and pricing strategies for future offerings, concluding...
Jun 19, 2025•54 min•Ep. 184
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 respective companies. They explore the challenges of managing growth, the importance of understanding customer needs, and the potential of AI to enhance efficiency and customer experience. The discussion also touches on the significance of vertical integration and the future of AI in business, emphasizing ...
Jun 05, 2025•55 min•Ep. 183
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 dynamics of business growth, and the implications of freemium models in their respective companies. The discussion delves into the importance of customer retention versus acquisition, the value of free users, and the efficiency required in service-heavy business models. Throughout the conversation, t...
May 22, 2025•53 min•Ep. 182
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 challenges and opportunities in building a health insurance platform. They explore the concept of 'vibe coding' and how AI is reshaping software development and content creation. The conversation concludes with a brainstorming session on packaging benefits for LegUp Health, emphasizing the importance of...
Apr 26, 2025•57 min•Ep. 181
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 concerns, product development, and the importance of identifying ideal customer personas. They explore the balance between adding features and maintaining simplicity, as well as the need to adapt to changing market conditions.
Apr 10, 2025•56 min•Ep. 180
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 balance between calm and chaos in business operations. They explore the importance of setting realistic goals, the role of automation in enhancing user experience, and the impact of parental leave on work dynamics. The discussion emphasizes the need for focused opportunities in sales and the potenti...
Mar 27, 2025•55 min•Ep. 179
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 delve into the challenges of customer service and the need for a consultative approach to selling, emphasizing the value of understanding customer needs and providing tailored solutions. The conversation also touches on the updates to their form builder and the strategies being implemented to increas...
Mar 13, 2025•52 min•Ep. 178
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•48 min•Ep. 177
Line go up
In this episode, we talk about some metrics that are headed in the right direction. Let’s go
Jan 16, 2025•45 min•Ep. 176
Rating growth channels
In this episode, we try to prioritize some of the different growth channels Rick is considering for 2025.
Jan 02, 2025•48 min•Ep. 175
2024 Recap
In this episode, we recap 2024 and set goals for 2025: Personal goals for 2025: Rick: Primary theme: Buy back time Take 1 personal day every 1-2 months Get time back for things I love (skiing, basketball, be present on vacations, reading/writing, local networking) Have a familiy vacation on the calendar to look forward to at all times Tyler Baby stuff Remain flexible and do whatever needs to be done Create space for Shelly to have a life outside of just parenting Take advantage of the calm life ...
Dec 19, 2024•1 hr 11 min•Ep. 174
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•52 min•Ep. 173
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•47 min•Ep. 172
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•47 min•Ep. 171
Everybody’s marketing
We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying.
Oct 10, 2024•54 min•Ep. 170
How’s 2024 going
In this episode, we review our yearly goals, talk about some new AI tools we’re trying out, and more.
Sep 26, 2024•55 min•Ep. 169
How AI might impact customer service
In this episode, we talk about how we’re thinking about customer service in a world of AI*, and we do a deep dive into a customer interview Rick did recently. *Clickbait warning: We don't actually spend much time on this topic, I just wanted a catchy title for the episode. Did it work? Did you listen because of my misleading title? Let me know in the comments** **There are no comments. This is a podcast.
Aug 29, 2024•50 min•Ep. 168
The internet isn’t fun anymore
In this episode, we talk about the value of a podcast community, and generally how we’re trying to protect ourselves from the internet.
Aug 15, 2024•49 min•Ep. 167
How to raise revenue by 20% in one day
In this episode, we talk about about the impact a recent price change is having on Less Annoying CRM’s finances.
Aug 01, 2024•46 min•Ep. 166
Small bets vs going deep
The internet loves to talk about whether to focus on a single business or build a portfolio of small bets. I’m sure you’re sick of hearing about it. But in this episode, we have a twist on that topic. For an established business thinking about launching complimentary products, is it better to build one great one, or a series of only ok ones.
Jul 05, 2024•43 min•Ep. 165
Pick one thing and max it out
In this episode, we talk about how the job of an entrepreneur isn’t to decide which ideas are good and which are bad. It’s to pick the single best idea out of a sea of good ideas.
Jun 25, 2024•47 min•Ep. 164
Step on the gas, or pull back?
In this episode, we talk about a decision Rick needs to make with LegUp Health. Should he treat it like a high-growth startup, or a lifestyle business?
Jun 06, 2024•51 min•Ep. 163
We ain't talking about zero to one
In this episode, we talk about how a lot of startup advice is focused on businesses going from zero to one, and how we have to be careful not to assume that all applies to us.
May 16, 2024•52 min•Ep. 162
Forms forms forms
In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the business
May 09, 2024•49 min•Ep. 161
Leveling up the team
In this episode, we discuss using consultants to level up your team.
Apr 25, 2024•41 min•Ep. 160
The first step of a flywheel
In this episode, Rick explains how he’s getting more hands on with marketing.
Apr 11, 2024•55 min•Ep. 159
Sometimes you need to touch the hot stove
In this episode, we discuss how some lessons can't be taught, they have to be learned through experience. What does that mean for mentoring less experienced employees?
Mar 28, 2024•52 min•Ep. 158
When to outsource
In this episode, we talk about when it makes sense to outsource work to contractors and agencies, vs when it makes sense to do something in-house.
Feb 29, 2024•49 min•Ep. 157
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