Startup to Last

This is our yearly recap episode!Personal updates from 2023TylerGoals 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 2024TylerMaintain exercise routine: 9k steps/day + 2 rucks/week + 200 pushups/weekFinish house remodelRickRebuild daily exercise and writing habitBe more present with family when I’m with themRegular dates with Sable (2 per month minimum)4 vacations, with at least the next one scheduled at all times to look forward toProfessional updates from 2023Themes of the podcastYou can't optimize nothing (mostly applies to Rick)Back to the basics (mostly applies to Tyler)TylerGoals from last year❌ Get back to decent growth: $36k ARR/ $3k MRR per month✅ Sense of urgency on the dev team. No more 2-week projects that end up taking six months.🆗 End the year with three major product winsOther updates Announced the price increase for legacy customers  ~3 new devs sort of. Dev team is feeling way better than ever before. Improved money management Coded a lotJoined LegUp Health as a side projectRickGoals from last year✅ Retain JD full-time for another year🆗 Double the client base again (~200 clients) - 160 clients❌ Build V1 of LegUp Benefits and generate $1K per month in MRR from it (3-4 customers)Other updatesTyler joined LegUp Health as a partner Expanded services to group health insurance, and started figuring that out Made it to $100K annual revenue run rate + profitability in DecemberProfessional goals for 2024TylerDon't worry about growth unless something unexpected happensFocus on customer delight: If you ask a typical customer whether LACRM improved in 2024, their answer should be "hell yeah"Maintain stability related to the team, culture, etc.Protect coding time. Should be averaging >1 full day of coding per weekRickGet LegUp Health to $200K ARRApply Profit First Framework / Pay partner distributions, even if smallGet JD to his target compensationPrioritize better at Windfall / leverage over optimizationBiggest worryTyler: Our execution on the product side won't be enough to close the gap with competitorsRick:  I won’t figure out how to prioritize and manage my personal health as I build a family What we want to learnTyler: How to code like it's 2024. Should be able to do everything the other LACRM devs can do with no blind spotsRick: Nothing specific. 2024 is about execution

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 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.