
Startup to Last
Two founders talk about how to build software businesses that are meant to last. Each episode includes a deep dive into a different topic related to starting, growing, and sustaining a healthy business.
Latest episodes

Dec 11, 2020 • 54min
Celebrating wins in the early days
Other topics we covered this week:Advent of codeThe 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.

Dec 3, 2020 • 1h 5min
Info products moving to a subscription model
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.

Nov 26, 2020 • 55min
Planning a marketing sprint
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.

Nov 19, 2020 • 1h 3min
Traction vs distraction
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 LegUp Health, including making an appearance on tv.Tyler reports on the results of some help site changes Less Annoying CRM made a while back..Tyler is planning a design fellowship.

Nov 12, 2020 • 1h 5min
Setting goals when you're just getting started
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.

Nov 5, 2020 • 1h 6min
How big to go when moving upmarket
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.

Oct 29, 2020 • 1h 6min
Startup community fatigue
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 celebrating their 20-year anniversary.Rick is interested in grain.co.Instagram/Facebook are a cancer upon humanity and they should be destroyed. Or they should let Rick log into his account. Either way.We discuss how Less Annoying CRM could package and position their product in a future where they have multiple sub-products all within the same app.

Oct 22, 2020 • 1h 9min
Offering night and weekend support without burning out your team
Some other topics discussed this week:Rick separated his marketing site from his app and launched a site for his b2b product: www.legupbenefits.comLess 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 logo on them.Rick will yell at me if I don't point out that he didn't get the ones with Slack's logo, he got the same type of shoe without the logo.We give a few shoutouts:Demodesk is a great tool for giving demos to customers.Turn the ship around is a helpful book on leadership.This episode on health insurance for startup founders is interesting and started a conversation about premium tax credits.

Oct 16, 2020 • 60min
The perils of being dependent on a platform
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 houseTyler 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 tools) as well as distribution platforms (e.g. the Shopify app store)We talk about how Covid might impact things for the rest of the year.

Oct 8, 2020 • 1h 4min
Building a moat
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 marketplaceRick 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 customer they've had before.Rick complains about his CRM adding data automatically.We give a shoutout to Rick's wife who helped launch Lucidspark.We give a shoutout to Dru Riley and Trends.vc.We give a shoutout (how many shoutouts are there?) to Courtland Allen who's starting a podcast network which we're joining.Tyler complains about restaurants that aren't trying to compete.Rick likes some extremely stupid shoes that Cole Haan made in partnership with Slack.