In this episode, we discuss using consultants to level up your team.

 In this episode, Rick explains how he’s getting more hands on with marketing. 

In this episode, we discuss how some lessons can't be taught, they have to be learned through experience. What does that mean for mentoring less experienced employees?

 In this episode, we talk about when it makes sense to outsource work to contractors and agencies, vs when it makes sense to do something in-house.

 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 TylerGoals from last year🆗 Take more vacation and make up with with extra work off-hours work🆗 Renovate the houseOther updatesFound a band I like: Caligula's HorseFirst time as an adult I feel good about my exercise routineRickGoals from last year❌ Get weight below 200lbs❌ Write a newsletter most Sundays (27 total)Other updatesBuilt a new house and moved inHad another baby (daughter)Personal goals for 2024 TylerMaintain exercise...

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 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...

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...

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...

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...

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...

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...

 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...