Startup to Last

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 teamRick 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.

Rick shares the chaos and joy of juggling two kids while balancing work demands. The discussion dives into addressing a drop in client engagement and offers insights on refining outreach strategies. The team also navigates the migration from Google Analytics to Fathom, highlighting the need for meaningful data over complex metrics. They ponder over pricing new features and reflect on the cyclical nature of business growth, emphasizing the importance of real metrics for decision-making. Plus, they explore the value of customer webinars for enhanced software optimization.

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 projectLegUp Health has updated their mission and core valuesThings are a bit hectic at LACRMTyler is considering merging his personal blog back into the LACRM blogLACRM is probably switching from Stripe to PaddleRick shares what he's learned servicing the early LegUp Health group insurance clientsWe talk a bit about ChatGPT and how it can be useful for no-code/low-code appsTyler 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.