Startup to Last

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.

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 sabbaticalLACRM is getting ready to launch a major redesignRick gives updates on how the LegUp Health/Benefits plan has changedBecause of the changes, we renegotiated Tyler's compensation and involvement in the companyTyler 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 coachWe 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.

Dive into the birth of LegUp Benefits with insights on early product development and the importance of customer validation. Listen to team dynamics evolve as a marketing coach is introduced to enhance internal communication. Hear personal reflections on sabbaticals and the emotional rollercoaster of startup life. Explore innovative rebranding and the use of new communication tools for better customer outreach. The complexities of group health insurance and the need for effective payment solutions are tackled, emphasizing strategic approaches to navigating challenges.

 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 NotionAIBig 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 ConfTyler is getting ready for a sabbatical which means delegating a lot of work to other peopleRick talks about gather customer profiles at LegUp HealthRick explains what "aged leads" areWe discuss whether or not it makes sense for Rick to go after group health insurance clientsTyler talks about an LACRM company traditionLACRM launched their Zapier integration!Tyler is preparing to do more design workWe have some rants and shoutoutsWe talk about what to do when a lead asks for security certifications and/or asks you to fill out a questionnaire 

Topics this week:Tyler is going to work with Rick to build the new LegUp Benefits SaaS productRick has officially transitioned LegUp to 2023Rick talks about how Airtable Interfaces are usefulRick talks about an annual retreat with JD, and we discuss rituals and traditionsTyler is going to Big Snow Tiny ConfLACRM launched their new API, and are almost ready to launch Zapier integrationWe talk about the value of podcasting