
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.
Latest episodes

Dec 5, 2024 • 52min
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.

Nov 21, 2024 • 47min
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 7, 2024 • 47min
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.

Oct 10, 2024 • 54min
Everybody’s marketing
We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying.

Sep 26, 2024 • 55min
How’s 2024 going
In this episode, we review our yearly goals, talk about some new AI tools we’re trying out, and more.

5 snips
Aug 29, 2024 • 50min
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.

6 snips
Aug 15, 2024 • 49min
The internet isn’t fun anymore
The hosts emphasize the importance of a supportive podcast community while sharing personal anecdotes about frustrating home repairs. They discuss the challenges of home renovations and celebrate a colleague's milestones in podcasting. A nostalgic look at social media's evolution highlights the need for intentional online habits. They also share insights on successful offsite meetings and client engagement strategies. Finally, there's a humorous debate about the practicality of getting a Tesla Cybertruck for their business.

Aug 1, 2024 • 46min
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.

Jul 5, 2024 • 43min
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.

Jun 25, 2024 • 47min
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.