June 4, 2026Episode 20451 min
HIPAA
In this episode, we dive into one of the most exciting topics imaginable: HIPAA compliance
Episodes
205
Latest episode
Jun 2026
Language
EN
About the show
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.
Listen to episodes
May 19, 2026Episode 20347 min
It’s a Tyler episode
In this episode, we dive deep into Less Annoying CRM’s new marketing strategy.
April 23, 2026Episode 20254 min
Where do the humans fit in?
In this episode, we talk about how one of the new business challenges is to figure out what skills are uniquely human, and leaning into those things as your differentiator.
April 9, 2026Episode 20150 min
Where to host a marketing site in the age of AI
In this episode, we talk about whether tools like Webflow still make sense to use when AI can generate professional looking marketing sites for you.
March 27, 2026Episode 20051 min
How much to invest in growth
In this episode, we talk about how Rick has changed LegUp Health’s formula that decides how much money is available to invest in growth.
March 12, 2026Episode 19953 min
Do custom Notion agents really work?
No, they don't!
February 27, 2026Episode 19851 min
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.
February 12, 2026Episode 19754 min
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.
January 15, 2026Episode 19648 min
Obligatory Claude Code episode
In this episode, we talk about the only thing anyone is talking about right now: Claude Code.
December 31, 2025Episode 1951 hr 57 min
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 from reactive to proactive (and surviving to thriving)Shifting from a strategy of playing it safe and reducing risk to taking smart risk and being ok looking a little foolishTyler Handle the transition back to full-time work (as it impacts parenting)Find clarity on what level of wealth we’re comfortable exposing our daughter to.Help Shelly find more ways to go out at night while I take care of SydFinalize will+trustStretch goal: Start vibe coding personal appsProfessional goals for 2026Rick (hopes to achieve at least two of these goals) Outsource, delegate, or automate recurring tasks that I no longer value doing and/or others don’t value me doingTry to grow LegUp Health by 50%, but do it in a way that we are all excited aboutRebuild personal website + read 10 really, really good nonfiction books and publish notes on themExperiment with AI to generate 1 additional revenue streamTyler Spend almost all IC time on design, product management, and coding. Fewer distractions!Management: Get the team up to speed on AI, and make it self-sustainingProduct management/design: Figure out how to keep up with the devs (especially if AI allows them to move even faster)Product Ship Mobile and KanbanReduce support by making things more self-serveMain theme: The first 30 minutes Onboarding improvementsRebuild the importing flowSimplification Separate contacts and companiesOpen contacts in page dialogStatuses on the contact recordTable view of contacts
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