Startup to Last

Other topics this week: Rick officially launched a "give back" program Rick decided not to post internship openings until post-parental leave. Rick wants to start a group focused on reaching local consumers. Tyler is planning an at-home retreat. Morale is a bit low as covid drags on. We discuss a specific UI decision LACRM is facing. We discuss aligning what you want to have happen with what will...

Other topics this week: How Robinhood's recent controversy applies to Rick's business model. Rick received his first cancelation. Twitter acquired Revue. Rick is working on a low-code solution to an automation issue. Tyler is close to closing a deal with an enterprise client. We discuss how to handle security audits (e.g. SOC 2 compliance) with enterprise customers.

Other topics this week: Less Annoying CRM hit $3 million ARR, and the tweet about it got a lot of engagement. Rick paid out referral rewards to his clients. Rick explains his buyer journey exercise. Rick reflects on the value of customer appreciation. Tyler has been a guest on several other podcasts. We discuss how to react when a competitor launches. We discuss the idea of building buffer into ev...

Other topics this week: Tyler reviews what he learned from last week's DDoS attack. Rick has planned out the year and feels good about his ability to get it done. Rick is allocating 50% of his time to promotion and 50% to automating his product. Tyler is about to start teaching a design course. LACRM is close to finishing a migration to Webflow. We discuss Clubhouse. Tyler is getting a Peloton. Ri...

Other topics in this episode: Trump and his group of domestic terrorists are trying to overthrow the government and it sucks. What a Democrat-controlled government means for healthcare Rick's business is extremely seasonal. We give financial updates from 2020. Rick is working on some tooling changes: Twilio, Front, and knowledge bases. Don't be envious of other people.

Looking back at 2020 Note, many of the goals mentioned here were set in our 2019 recap episode . Personal accomplishments  Rick  2019 Goal: Get to a point where he and his wife feel comfortable having kids - ✅ Not only are they ready, Rick's wife is pregnant 🎉 2019 Goal: Increase level of play - ✅ He's been playing basketball, skiing, playing water sports, etc. Had success writing his newslette...

Other topics: Tyler realized he might have more revenue growth next year than he originally thought. Rick is learning that things don't die down immediately after open enrollment, and that's making it hard to do end-of-year planning. Tyler has been thinking about what the approach might be when LACRM re-opens the office. Rick is meeting his intern for the first time in-person. Rick switched to Not...

Other topics from this episode: Rick is finished with open enrollment and walks through some metrics. Rick is expecting his first churn from customers who signed up earlier this year. Rick realizes that word of mouth happens at specific moments in time, such as when someone leaves their job, gets married, or has some other life event. Tyler is learning more about his strengths and weaknesses. Tyle...

Other topics we covered this week: Advent of code The Less Annoying CRM design fellowship is finalized. Rick has a few different channels that are showing traction including Instagram DMs and getting referrals from other insurance agents.

Here are some of the other topics we discuss: Slack was acquired by Salesforce for a bunch of money. Like, a whole lot. Stripe launched a new "Treasury" product. Tyler finished his end-of-year planning. Rick has been bouncing between projects. Google Search Console has been broken for Rick. My first million is a good podcast.

Because this is a short week, we didn't have many updates. Instead we focused on two main topics: The trend of SaaS companies bundling multiple products into a single subscription. Rick's marketing plan for the next few weeks.

Some topics we cover: Rick has been reading two new books that teach about avoiding distraction and staying focused. Tyler had a product strategy breakthrough after giving himself time to think through a bunch of bad ideas first. Rick reflects on his failed startup from last year and we discuss the merits of having a portfolio of products vs a single product to focus on. Rick has been marketing Le...

Other topics we discussed this week: Tyler has another lesson to share from the book he's reading. Rick stopped marketing and he's struggling to get momentum back. Tyler is trying to design team permissions for Less Annoying CRM and it's proving to be difficult. We give a shoutout to Jetboost . Rick is frustrated that no-code tools aren't more transparent about their product priorities.

Other topics this episode: Tyler is switching Less Annoying CRM to Notion. Rick is finished with outreach to existing customers to prepare for open enrollment. Next up is marketing/sales. Rick's employee Lena is doing a great job executing their content strategy. Tyler gives an update on Less Annoying CRM's financial results in October.

Some other topics from this week: Rick is getting ready for open enrollment, and he explains the history behind why health insurance is sold all at the same time in the U.S. Tyler has been talking to customers a lot recently. Tyler is using "revenue per employee" as a simple guide for whether or not LACRM can afford to hire employees. Wildbit shows what it means to "startup to last" after celebrat...

Some other topics discussed this week: Rick separated his marketing site from his app and launched a site for his b2b product: www.legupbenefits.com Less Annoying CRM launched a new help site and in-app help center. We discuss what interns can do to get the most out of a remote internship. Rick's ridiculous shoes arrived and they're meh. The lesson is: Don't buy shoes because a company put their l...

Here are the topics we covered this week: Tyler has to decide between keeping his design consistent vs. optimizing each page's design for the content on that page. Rick has moved into a new house Tyler had his first meeting with the new mastermind group. Tyler gives updates on his ongoing Webflow project. We discuss the upsides and downsides of building a startup on tech platforms (e.g. no-code to...

Here's what we discussed this week: Tyler gives an update on the 1:1 meetings he's had with his whole team over the last week. Rick launched a digital health tool marketplace Rick is wrapping up his projects from earlier in the year and is ready to focus on a few important things going forward. Less Annoying CRM is close to close two new accounts, each of which are significantly larger than any cu...

Here are the topics we discuss this week: The difference between work and hobbies when hobbies involve work topics. Rick is focusing more on outreach. Tyler gave a 6-month presentation to his employees. Rick is about to build his employer-facing product using Glide . Should startups with multiple products put them all under a single brand umbrella, or run separate marketing sites for each one? Ric...

Here are some topics we discussed this week: Rick was on an entrepreneurship panel at his former high school. Rick has automated most of the onboarding process at LegUp health. Tyler gives an update on his price increase. Rick closed his first employer client and has lots of other opportunities coming up soon. Rick gives shout-outs to The Infinite Game and INTRO (we also discuss Trailhead ). We co...

Here are the topics this week: Rick is on a roll with his website build-out. Check it out at leguphealth.com and let him know what you think. We talk about mistakes you can make when handing off ownership to employees. Tyler is reconsidering the benefits philosophy at LACRM. Rick is thinking about how to build out an employer-facing app.

Here are some of the topics we covered this week: Tyler is preparing for vacation. Rick has his new CRM set up. Rick is working on his website and isn't sure the right approach to take. Less Annoying CRM hired a new developer. Less Annoying CRM has a bunch of new features getting launched. Tyler is considering how to get the rest of the team more involved in product prioritization. Rick has been a...

This week, we had a special guest: Malia Jones . We discussed how to teach no-code to beginners.

Here are some topics: Rick is taking a vacation which has him considering if his business should be remote-first so he can spend more time outside of Utah. Tyler was on support last weekend and started testing out ways to limit wasteful uses of customer service time. Tyler is prepping a presentation for his employees which he does every six months. Tyler is formalizing the org chart at LACRM a bit...

Here are some of the topics from this episode: University leadership handling covid this fall. Rick is using Copper CRM. Rick is done with positioning and moving on to making a website. Tyler has pricing and growth updates. Tyler has been learning about co-ops and thinking about succession plans. We discuss whether ARR or MRR is the right metric to communicate to the team. We discuss whether or no...