In this episode, we talk about Rick’s early signs of success getting out a sales rut, and much more.

Full topic list:

• Rick gives an update on how he and JD are getting out of a sales rut.
• Rick is busy and has absolutely zero free time.
• Tyler talks about how he's considering web forms and automations as possible features for LACRM.
• We discuss an alternative approach to freemium.
• We brainstorm how to use the "engineering as marketing" approach for LegUp Health, but don't really get anywhere.

In this episode, we talk about how much optimization should be done before you have demand generation figured out.

Here's the full topic list:

• Rick is back from parental leave, and he has things to say about what it's like to take care of two kids at once.
• We discuss what our perfect days look like.
• Tyler talks about how LACRM had a bit of crunch mode, and how they stayed calm.
• Rick talks about a sales slump, and what he's doing about it.
• We talk about how LegUp Health migrated from no-code to full-code.
• Tyler gives an update on LACRM's growth the first half of the year.
• We talk about switching from Google Analytics to Fathom.
• LACRM is considering how to price a feature that has some extra infrastructure costs.
• Tyler is reconsidering a feature he's been talking about for years. Literally. Years.

In this episode, we talk about what Less Annoying CRM is doing to handle sales tax compliance worldwide.

Here are all the topics:

• Tyler has officially signed the partnership agreement with Rick and LegUp Health!
• Rick is wrapping up a position/brand/story project
• LegUp Health has updated their mission and core values
• Things are a bit hectic at LACRM
• Tyler is considering merging his personal blog back into the LACRM blog
• LACRM is probably switching from Stripe to Paddle
• Rick shares what he's learned servicing the early LegUp Health group insurance clients
• We talk a bit about ChatGPT and how it can be useful for no-code/low-code apps
• Tyler rants about how we talk about priorities

In this episode, we talk about Less Annoying CRM’s producthunt launch, and a lot more.

Here's the full topic list:

• Tyler takes a look back at LACRM's growth history, and explains their new approach to growth.
• Tyler explains how the recent Product Hunt launch went.
• Rick has cleared a lot off his LegUp Health plate and is starting to focus on new types of work.
• LegUp Health had its first partner meeting.
• April was a record month for LegUp Health.
• LACRM has their designer back with more hours than ever.
• Rick is looking to target CPAs as customers.
• The LACRM coding fellows have started.
• We discuss how to deal with the low points of being an entrepreneur.

In this episode, we discuss some changes to LegUp Health, the end of Tyler's sabbatical, and more.

Topics in this episode:

• Tyler is back from his sabbatical
• LACRM is getting ready to launch a major redesign
• Rick gives updates on how the LegUp Health/Benefits plan has changed
• Because of the changes, we renegotiated Tyler's compensation and involvement in the company
• Tyler talks about the difference building a product that customers don't expect to use regularly vs and every-day productivity tool.
• Rick gives an update on working with a marketing coach
• We talk about Seeyafuture.me

Come on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules.

In this episode, we talk about the very early stages of building LegUp Benefits, and a bunch of other stuff. 

Topics:

• Rick has hired a marketing coach for LegUp, and we discuss how to get the team talking to each other more instead of having everything flow through Rick.
• Tyler gives some reflections on leaving LACRM for 6 weeks, and the early days of his sabbatical.
• Tyler describes a new positioning idea at LACRM.
• We discuss the early work on LegUp Benefits including customer validation and learning a new tech stack.
• Rick gives an update on his new group insurance efforts.
• We talk about Silicon Valley Bank even though we don't have anything to say that hasn't already been said.

 In this episode, we talk about how bootstrappers can win against companies that have raised massive amounts of money.

Full topic list:

• We give an update on the compensation negotiations we discussed last episode. We've agreed on terms for Tyler to work for Rick on LegUp Benefits!
• Rick had his first annual offsite and shares a ton of great learnings.
• LACRM had a great month in February. There was absolutely nothing to learn from it.
• LACRM's major redesign is getting closer.
• Rick has streamlined bookkeeping and other financial tasks to save time.
• Tyler is thinking through when it makes sense to do custom work for a large client.
• We tackle a listener question: How do bootstrapped companies compete with funded competitors.

If you’ve been following along, you know that Tyler is about to temporarily join Rick’s startup to help build their new app. In this episode, we talk about the compensation proposal Rick just came up with. 

Full topic list:

• Rick already has a new group insurance client after deciding to give that a shot in the last episode.
• JD is visiting Rick in Utah next weekend.
• Tyler is having success with delegation, and finds himself with a lot of unstructured time on his hands...
• ...and Tyler is having to re-learn what to do with unstructured time.
• LegUp Health got hit with a bunch of spam contact forms.
• Tyler is planning the new office layout for LACRM.
• Apparently design debt is a thing.
• Tyler is having trouble getting started on the LegUp Benefits project. Side projects are hard.
• Rick brings up Youtube Premium, Quora, and NotionAI
• Big topic: We discuss the compensation proposal that Rick just sent Tyler.

 In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more.

Topics in this episode:

• Tyler shares his experience at Big Snow Tiny Conf
• Tyler is getting ready for a sabbatical which means delegating a lot of work to other people
• Rick talks about gather customer profiles at LegUp Health
• Rick explains what "aged leads" are
• We discuss whether or not it makes sense for Rick to go after group health insurance clients
• Tyler talks about an LACRM company tradition
• LACRM launched their Zapier integration!
• Tyler is preparing to do more design work
• We have some rants and shoutouts
• We talk about what to do when a lead asks for security certifications and/or asks you to fill out a questionnaire