Startup to Last

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 conclude...

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 cha...

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...

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 conversati...

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

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

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

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 do...

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

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

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

We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying.

In this episode, we review our yearly goals, talk about some new AI tools we’re trying out, and more.

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 p...

In this episode, we talk about the value of a podcast community, and generally how we’re trying to protect ourselves from the internet.

In this episode, we talk about about the impact a recent price change is having on Less Annoying CRM’s finances. 

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. 

 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. 

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? 

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.

 In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the business 

In this episode, we discuss using consultants to level up your team.

 In this episode, Rick explains how he’s getting more hands on with marketing. 

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?

 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.