Startup to Last

 In this episode, we talk about Less Annoying CRM’s latest sales experiment. 

In this episode, we talk about takeaways from big snow tiny conf, and more.

In this episode, we discuss how Rick is using the “profit first” mindset to manage company finances. 

This is our yearly recap episode! Personal updates from 2023 Tyler Goals from last year 🆗 Take more vacation and make up with with extra work off-hours work 🆗 Renovate the house Other updates Found a band I like: Caligula's Horse First time as an adult I feel good about my exercise routine Rick Goals from last year ❌ Get weight below 200lbs ❌ Write a newsletter most Sundays (27 total) Other up...

In this episode, we talk about Rick's open enrollment experience, and what LACRM is doing related to DEI (diversity, equity, and inclusion)

 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 s...

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...

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 idea...

 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 foc...

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 t...

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...

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 ba...

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 mee...

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...

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 positioni...

 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...

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 del...

 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 o...

Topics this week: Tyler is going to work with Rick to build the new LegUp Benefits SaaS product Rick has officially transitioned LegUp to 2023 Rick talks about how Airtable Interfaces are useful Rick talks about an annual retreat with JD, and we discuss rituals and traditions Tyler is going to Big Snow Tiny Conf LACRM launched their new API, and are almost ready to launch Zapier integration We tal...

Personal updates from 2022 Tyler Goals from last year ✅ Plan for travel as part of relationship  ❌ Build more schedule flexibility  Other updates Figured out personal finance plan with Shelly Rick Goals from last year ✅ Reprioritize daily personal health habits  ❓Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands)  ❌Writing goals Professional updates from...

Topics in this episode:  LACRM is having a good December Rick is feeling lots of momentum Rick gives an update on LegUp Health's growth Rick is reading the Warren Buffet bio: The Snowball Tyler explains LACRM's new approach to bug triage Rick is thinking about how hard to push for in-person Tyler describes a new shorthand: Following daylight Rick realizes he's learning a lot about digital marketin...