Startup to Last

 In this episode, Rick tries to explain to me that there are people who know how to grow businesses, and I stubbornly insist otherwise.

In this episode, we discuss what feels like an inflection point in Rick's business.

Full topic list:

• LegUp Health has a new website.
• Rick thinks he's feeling an inflection point.
• We daydream about the future of LegUp Health a bit.
• Things are calm at LACRM, and the employees are all increasingly experienced.
• Tyler is coding again.
• There's a new buzzword at LACRM.
• We complain about X/Twitter.

This week, we discuss how LegUp Health reduced a major point of friction when selling to employers.

Here's the full topic list:

• Rick is finally in his new house, and a major stress has been removed.
• Rick gives updates on LegUp Health, including a major unlock to getting employers onboard.
• Rick talks about progress towards hitting annual sales goals.
• Tyler talks about other ways he's been able to simplify LACRM's operations.
• Tyler has a coughing fit and we give up early.

In this episode, we discuss whether or not building features customers ask for is a valid path toward growth.

Here are all the topics:

• LACRM has started migrating to Paddle.
• LegUp Benefits has its first official customer!
• We discuss how LACRM's free trial pipeline isn't as correlated with paying user growth as you'd expect.
• We dive deep into the history of LACRM's product strategy, and what comes next.
• Rick has a major milestone to share.

This week, we talk about a pricing change we recently announced at Less Annoying CRM. We dive into the history behind the decision, how it was communicated, what it means for the finances of the business, and more.

In this episode, we discuss a hodgepodge of things including a company reorg, growth tactics, and more.

Here are all the topics:

• Rick updates us on LegUp Health's progress. He talks about working on the sales pitch, building momentum, staying focused, and more.
• Tyler is merging two teams at LACRM. We discuss what the impact of that change might be.
• We spend a while discussing different growth ideas, especially related to sales and outbound marketing.

 In this episode, we talk about how both of us are refocusing on execution. Here's the full topic list:

• Tyler is trying to focus everyone at LACRM on the top priorities including:
  • Having the devOps team do a bit more normal software engineering work.
  • Offering customer service people a chance to work on marketing and sales.
  • He himself is starting to code again.
• Rick explains how LegUp Health is focused on execution and it seems to be working.
• Rick/JD hired a sales coach.
• Rick talks about what he learned from the book Amp It Up.
• Tyler poorly explains why LACRM is going to work on a feature that isn't the top priority.
• We talk a bit about how to optimize a support team
• Rick is starting to think about how he can contribute to marketing.

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