Startup to Last

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 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.

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 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.

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 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.

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 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.

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 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.

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?
• Rick is switching from Google Meet to Zoom.
• Should startups ask for a credit card when signing up for a trial, or after the trial has ended?

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 commiserate about Webflow limitations.
• We talk about smart home devices (what does this have to do with startups? Nothing).