Startup to Last

Topics this week: Rick is close to finalizing a partnership agreement with his first team member. Tyler is excited that LACRM has been shipping a lot of product improvements lately. Tyler has a new productivity hack he's trying. LegUp Health is doing some cold outreach and so far it's working. LegUp Health joined a new business association. Tyler is nervous about some marketing trends even though...

Topics this week: Tyler is considering going to Founder Summit in Ashville this fall. LegUp Health signed a partnership deal with Pando Labs . LACRM is on a hiring spree. LACRM has a new thriving wage. We discuss whether video testimonials are a good idea. Tyler heard a podcast which made fun of LACRM's design, and this resulted in him getting some design coaching. We discuss how Rick can structur...

This is our annual retro/goal-setting episode. Here's what we cover: Personal updates from 2021 Tyler Goal from last year: ✅Spend more time with family and friends once vaccinated Other updates Started exercising Froze embryos Rick Goals from last year ✅ Get sleep under control ✅ Adjust to being a dad Other updates Wasn't good about exercising Has only been on one date with Sable Professional u...

This is our last episode. Thanks to everyone who has listened and supported us over the last couple years. We're going to miss you 😢 Topics in this episode: Rick accepted a new job. What does that mean for LegUp Health? Rick finished migrating his help site to Webflow. Rick notified his free users that the free service is shutting down. Tyler talks about compounding and what it means for thinking...

Topics this week: Rick is canceling his CRM subscription. Tyler is considering where his newsletter fits into his overall plan. Based on our conversation last week, Rick has new clarity around the future of LegUp Health. Tyler explains how LACRM came up with their long-term product roadmap. Rick is going through continuing education. We discuss some touchy feely things related to the passage of ti...

Topics from this episode: Less Annoying CRM is back to remote-first because of the new wave of the virus. LACRM had a new developer start this week. Rick is thinking about how to simplify his business. Specifically, what can he cut? We discuss what it means to be a calm company. Or is that even the goal?

Topics from this episode: Tyler hit 2,000 Twitter followers, and we discuss how Twitter is a hits-based business which doesn't suit Tyler's strengths. Rick gives an update on his personal website and newsletter optimization efforts. Rick reached the first page on an important search term. Less Annoying CRM is tweaking the format of help articles to appeal more the the easily distractible internet...

Topics this week: Tyler had fun with a once-per-year football bet, and Rick had to put in a full day of dad duty. Tyler is considering taking the ShiftNudge design course to get better at design. He also purchased a license to Tailwind UI so he can copy from better designers. LACRM is tweaking it's policy that everyone at the company must do an hour or support each week. Rick reflects on the value...

Topics this week: Rick launched LegUpBenefits.com . We discuss Rick's new no-code tool: Outseta. Less Annoying CRM has a new developer starting next month. Tyler has refined his approach to writing internal documentation, and Rick makes a fantastic analogy. Tyler's co-founder/brother will be in town next week. Rick wants to keep practicing coding so his skills don't deteriorate. Rick is taking a b...

Topics this week: Rick took some time off, but is wondering if he earned it. Tyler wrote five blog posts in one day, and wonders if this should be the new approach to blogging. Rick decided to wait for Memberstack updates before taking on a coding project he was planning. Rick is using Outseta for his next technical project to diversify away from Memberstack. He plans to have the done in the next...

Topics in this episode: Tyler was interviewed to be on Mixergy, but didn't think he did a great job. Rick is adjusting his routine now that he has a kid to take care of. Rick enrolled in a new javascript course to hone his skills. Tyler's previous positive results converting website visitors to his newsletter have turned to failure. No one is signing up. Tyler attended Less Annoying CRM's first le...

Topics this week: Tyler has a new iPad and doesn't know what it's good for. Rick has added a client through word of mouth, and we discuss how churn and word of mouth are constantly battling with one another. Rick has resolved a major issue one of his clients had with their dental insurance. Crisis averted. Tyler has been working on the wrong things, and is trying to correct that. We discuss Less A...

Tyler has a new mic. Tyler is in the middle of the final round of interviews for his new dev hire, and he's starting to plan onboarding. We discuss whether to put a new LACRM content project on the main lessannoyingcrm.com domain, or a separate mini-site. Rick finished taking his javascript course. Rick's dad is in town, and he's taking a bit of time off work. We discuss a trick for getting people...

Topics covered this week: We selfishly discuss larger themes we've covered on the podcast which might make for good topics on the Indie Hackers podcast. Tyler's newsletter signups have increased since changing the call-to-action. Rick lost another LegUp Health client due to unavoidable churn. Tyler has a content idea centered around CRM pricing. Tyler wants to do engineering as marketing but doesn...

Topics this week: Tyler asks Rick how he configured the call-to-action for his newsletter on his blog. Tyler is adding a curated list of links to his newsletter. Tyler overcame writers block and wrote his first support-focused blog post. Rick is curious what a highly-compensated support rep might look like at LegUp Health. Rick started paying for Notion. Tyler gives a shout-out to SavvyCal . We ta...

Topics in this episode: Apparently online courses have a very low completion rate, but maybe that's ok? Rick is learning more about javascript and has a few questions. Rick is taking a vacation where he'll fully unplug. Tyler gives some learnings from the recent enterprise deal that LACRM closed. Tyler has the interview process figured out for LACRM's next hire.

This week, we answer a few listener questions about how to make your first hire.

Topics this week: Rick crossed 200 subscribers for his personal newsletter. Rick gives an update on some recent milestones related to this podcast. Rick has been doing Wes Bos's beginner javascript course and is learning a lot. Tyler is on vacation, and is mostly just taking it easy. We discuss Notion's new API. Rick seriously sprained his ankle. Rick is dealing with a customer who is disappointed...

Topics this week: We're using a tool called ZipMessage to collect listener questions. If there's something you'd like us to discuss on the podcast, leave us an audio recording of your question at zipmessage.com/tyler Less Annoying CRM had a good April. LACRM's average account size is going up slightly, but it's having a significant impact on revenue. We discuss the theory of constraints, and how R...

Topics this week: An effective, but maybe sleazy tactic for cold emails. LegUp Benefits got its second paying customer. Rick is done with SEO for now, and wrote 35 new pieces of content in April (holy shit!) Rick is focusing on LegUp Benefits for the next six weeks. Less Annoying CRM has  finally closed a big enterprise deal they've been working on. Tyler is about to start trying to hire a develop...

Topics this week: Tyler gave an internal presentation at Less Annoying CRM and announced a few new things... The office is being reopened in May. There will be a new remote work policy in place. A deep dive into how DEI (diversity, equity, and inclusion) fits into Less Annoying CRM's structure. A new leadership team. Rick is working on content and had a big SEO win. We discuss Roam Research as a p...

Topics this week: Tyler is reading a book called Killing Marketing . Rick is trying some time management hacks. Tyler has a potential job candidate using his new approach to recruiting. Less Annoying CRM had their "day of rest" where developers take over customer service for a day. Rick is working on content and SEO for LegUp Health. Rick has filed his taxes. Rick gives a shoutout to a listener th...

Topics from this week: Rick has a baby! Rick broke $2k MRR in March. Tyler gives an update on his content marketing site. Tyler is about to start recruiting a developer. We talk about all the speculative bullshit going on right now (NFTs, GME, bitclout, etc.). Rick feels pressure to narrow his focus now that he's a father. We discuss how to implement an internal tool with no-code.

You can learn more about what Dru's working on on Twitter or at Trends.vc .

Because Rick is taking some time off for parental leave, we recorded a special episode this week. Rick is about to do a week-long retreat to try to finish a major project before becoming a dad. We're going to spend this episode discussing how he can get the most out of the retreat.