
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

Apr 29, 2021 • 1h 7min
The importance of internal communication
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 developer.Less Annoying CRM's office setup is changing, and we discuss the importance of communicating changes carefully.We discuss how to write content when you hit a wall.Rick is dealing with unavoidable churn.We talk for way too long about Basecamp's recent drama. We reach no conclusions. You can have a full refund for the amount you paid for this podcast if you're disappointed by that.

Apr 22, 2021 • 1h 4min
Empowering employees to be leaders
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 possible note-taking tool for Rick.Rick recommends Readwise.io for converting Kindle notes into text.We discuss schema markup as an SEO strategy.Rick has made some improvements to ricklindquist.com.Tyler might have more free time soon and needs to figure out what to work on.

Apr 15, 2021 • 55min
Time management
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 that makes software that verifies financial transactions who helped him with a question from last week.We discuss Webflow's product roadmap.

Apr 8, 2021 • 57min
$2k MRR
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.

Apr 1, 2021 • 1h 16min
Jamming with Dru Riley from Trends.vc
You can learn more about what Dru's working on on Twitter or at Trends.vc.

Mar 25, 2021 • 52min
Deep dive into an execution retreat
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.

Mar 18, 2021 • 57min
Burnout
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 our first vaccine shots, and we discuss what it would look like to re-open an office.Rick has realized how personal the information he needs from customers is, and how that impacts trust building.

Mar 11, 2021 • 59min
Enterprise sales is just project management
This discussion dives into how the new stimulus bill will reshape health insurance for entrepreneurs, making it more accessible. They also reflect on the juggling act of parenthood and managing projects. The conversation reveals enterprise sales as a form of project management, emphasizing stakeholder engagement and communication. Additionally, they analyze the significance of Zapier's acquisition of MakerPad in transforming the no-code ecosystem and enhancing sales practices.

Mar 4, 2021 • 56min
What does Indie.vc's move mean for startup to last companies?
Topics discussed:Indie.vc is shutting downRick 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.We discuss the long, slow SaaS ramp of death.

Feb 25, 2021 • 1h 2min
Hardcore week building a content site
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 ConvertKit.Tyler used Fiverr for the first time to hire a designer.We discuss multitasking for motivation.We both prefer creating content from our own personal voice rather than on behalf of the company.We brainstorm what's next for Less Annoying Business/