Startup to Last

Topics this week: Rick is feeling burnt out. We discuss how he noticed, and what he's doing to fix it. Rick's baby is expected this next week, so the next two weeks of the podcast will be pre-recorded episodes. Tyler is drowning in meetings. Tyler gives an update on his new content site. We talk a bit about SEO. Rick is looking for two plugins to help with his Webflow site. We have both received o...

Topics this week: Rick breaks down how the new stimulus bill will impact health insurance and entrepreneurs. Rick is putting his big project on hold until after paternity leave. Tyler gives an update on Less Annoying Business. We discuss enterprise sales, and how it's more about project management than convincing someone to buy. We talk about Zapier's acquisition of Makerpad.

Topics discussed: Indie.vc is shutting down Rick gives a revenue and churn update. Rick is preparing for the birth of his first child, but has one more big project to finish first. Tyler recaps the first week of results after launching Less Annoying Business last week. We discuss whether it makes sense to build an audience. Tyler is trying to get help with Elasticsearch from his online community....

Topics we covered today: Rick finished his goal for February of automating the monthly emails at Legup Health. Tyler gives an update on his new small business advice website. How do you like that link building I just did? Tyler remembers how fast a project can move when you don't have legacy code slowing you down. We discuss a variety of tools used to build a content site, especially Webflow and C...

Topics discussed this week: Rick is learning more powerful no-code tricks with Zapier, and advancing his PHP knowledge. We discuss the best way to learn how to write secure code. Tyler is wrapping up a big project which involves setting deadlines. We discuss healthy vs. unhealthy deadlines. Tyler is brainstorming content marketing approaches which is tough because he's not an expert on the topics...

More topics: We discuss the state of independent SaaS and what it means to have a very low payback period. Rick has installed a development environment and is learning to code again. Tyler is almost done getting ready to switch the LACRM marketing site to Webflow. Tyler is considering trying out Mixpanel. Salesforce is going more remote. What does that mean for San Francisco. We discuss Tyler's tw...

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...