
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

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.

Oct 1, 2020 • 1h 2min
Should multiple products share a single brand
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?

Sep 24, 2020 • 59min
All-nighters
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).

Sep 17, 2020 • 1h 8min
Handling capacity at a seasonal business
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.

Sep 11, 2020 • 1h 6min
Pricing annual plans when users are added mid-year
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 adding some new customers based on outreach he did months ago.Deep dive: How should Rick build and price and MVP of a new b2b service?

Sep 3, 2020 • 1h 10min
Learning no-code
This week, we had a special guest: Malia Jones. We discussed how to teach no-code to beginners.

Aug 27, 2020 • 59min
Networking without being annoying
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.We discuss how to network without annoying people.Rick has people reaching out looking for opportunities to work at LegUp Health and wants to figure out how to respond.

Aug 20, 2020 • 1h 2min
What if you get hit by a bus?
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 not it's healthy/smart/necessary to work more than 40 hours per week as a founder.

Aug 13, 2020 • 1h 4min
How college students can prepare for entrepreneurship
Here are some other topics we discussed:Tyler bought a house.Tyler is starting to do some startup mentorship.Rick's interns are gone.Rick has made progress on his positioning work.

Aug 7, 2020 • 1h 4min
The Sims, but way more boring
Here are the topics we discussed:LACRM shipped a handful of small improvements the interns had been working on.Tyler gives an update on the price increase.Rick is applying the positioning framework we applied last week which involved competitor analysis.Tyler officially decided to go with Sococo as a virtual office for the team while everyone is remote.Rick decided what to do with this Slack community.Rick's internship are wrapping up and he has a virtual get-together with all the interns next week.Tyler is getting close to deploying the first stage of his Webflow project.Rick wants to know how to maximize his experience with his first paid hire this fall.