
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 31, 2022 • 1h 44min
Looking back at 2022 and forward to 2023
Personal updates from 2022TylerGoals from last year✅ Plan for travel as part of relationship ❌ Build more schedule flexibility Other updatesFigured out personal finance plan with ShellyRickGoals from last year✅ Reprioritize daily personal health habits ❓Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands) ❌Writing goalsProfessional updates from 2022TylerGoals from last year❓ Spend more time working, but on my own terms ❓ Make space to do more individual contributor design work ❌ Release redesign of LACRM❓ Two blog post-worthy updates per quarter✅ Shift product priorities to be more focused on growth/strategy and less on low-impact customer requests.✅ Run the coding fellowshipOther updatesMore of a CEO, less of a managerGrowth was bad, but not as bad as expectedProduct team got more focusedRickGoals from last year✅ Structure a partnership and financial plan that enables JD to go full-time❌ Grow the business to 400 clients ❓Fully automate the new user onboarding experience✅ Help scale Windfall the right way 2023 personal themes/goalsTyler Take more vacation and make up for it with extra work days Start working towards my rich life: Renovate the houseRickGet weight below 200lbs Write a newsletter most Sundays (at least 27 Newsletters)2023 professional themes/goalsTylerReap the rewards we sowed in 2022 (marketing projects and product team productivity)Get back to decent growth: +$36k ARR per monthMore of a sense of urgency on the dev teamThree major product winsRedesignFinish all "first round" growth projects (Zapier, API platform, event invites)Close the gap between us as other CRMs (email logging and/or kanban view)If there's a recession, minimize impact on customers and employeesRickRetain JD for another yearDouble the client base again (~200 clients)Build v1 of LegUp Benefits and get to $1k MRRBiggest worryTyler: Product relevance - Have we lost ground in the CRM marketRick: Personal and family healthWhat do we want to learn?TylerHow to communicate how decisions are made betterHow to simplify policies so they are easier to understandRickHow to build a SaaS via contractors and self-taught coding (i.e. without giving up equity)Further expertise in digital advertising and dataBest practices for effective leadership (in the home, neighborhood, and workplace)PredictionsTylerGenerative AI will advance, but not break through in 2023 (it will still seem more like the future than the present at the end of the year)Binance and/or Tether will collapse, and Bitcoin will end the year downThe recession will get worseS&P500 will be down over the first half of the yearThere will be more tech layoffs in 2023 than there were in 2022Rick Big swing back to co-location as a working requirement AI gets embedded into workflows for millennials

Dec 13, 2022 • 1h 5min
Big bets vs small bets
Topics in this episode: LACRM is having a good DecemberRick is feeling lots of momentumRick gives an update on LegUp Health's growthRick is reading the Warren Buffet bio: The SnowballTyler explains LACRM's new approach to bug triageRick is thinking about how hard to push for in-personTyler describes a new shorthand: Following daylightRick realizes he's learning a lot about digital marketingWe discuss how it's good for businesses to be boring and complexRicks suggests having "certifications" for new hiresWe discuss Webflow LogicRick is going on a date!Tyler is trying to decide how to prioritize big bets vs. small bets at LACRM.

Dec 2, 2022 • 1h 1min
How can founders use the new AI tech?
Topics:Rick gives an update on open enrollmentTyler talks about some upcoming product launches including the new Zapier integrationRick is refining his Adwords approachRick is starting to think about 2023Tyler talks about project managementLACRM had a CRM Coach culture refreshWe talk about the recent wave of AI innovation

Nov 11, 2022 • 59min
Professional hater
Topics this week:I mean, Twitter, obviouslyRick gives an update on open enrollment including...Sales so farHis misadventures with Google advertisingWebsite positioning and designTyler gives an update on LACRM's integration projectLACRM just went through a process that happens every six monthsWe talk fruitlessly about the potential recession and tech layoffs

Oct 27, 2022 • 1h 1min
An opportunity that comes along once per year
Topics from this episode:Rick gives a big update on how LegUp Health is prepping for open enrollmentHis goal is to be long-term patient, but have short-term urgencyHe doesn't have enough traffic for retargetingOutreach will be their main leverThis weekend is his chance to get everything ready for November 1stTyler talks about his time at Founder SummitLACRM is thinking about brand marketing instead of just performance marketingTyler recounts a churn cohort analysis they did at LACRMRick shares some advice he got from a friendTyler gives an update on LACRM's integration partnersWe discuss "Courses as marketing"We talk about the value of sharing what you're working on with other people

Oct 14, 2022 • 54min
What's priority #1?
Topics this week:Tyler is getting ready for Founder SummitRick is learning about digital advertising, and we discuss whether tracking people on the internet is a net good or bad thingTyler gives an update on his NPS sagaTyler talks about a joint webinar he did with ZipMessageRick describes his chamber of commerce webinar strategyWindfall is opening a Utah officeRick is getting ready to do outreach, but needs to reduce friction firstTyler is making some changes to how he approaches project management and prioritizationWe discuss a possible niche audienceRick explains how a major hole in the health insurance laws has been fixedTyler started listening to the ShipSaaSFaster podcast

Sep 30, 2022 • 57min
The marketing tech stack
I (Tyler) am traveling and don't have time to write up show notes, so the other topics in this episode are a mystery. Enjoy!

Sep 16, 2022 • 59min
How much to spend acquiring a customer
Topics this week:Figma got acquired by Adobe AND I DONT WANT TO TALK ABOUT IT I'M NOT CRYING YOU'RE CRYING SHUT UP YOU'RE NOT MY REAL DADRick spent a week in Cancun and soaked up some sweet business wisdomTyler is experiencing a period of calm at work and has done some coding for the first time in a long timeLACRM decided not to hire interns next summerRick and JD planned their marketing blitzTyler gives an update on his work to make LACRM into a platform for API integrationsWe discuss how a company should decide what they're willing to spend on customer acquisitionTyler heard a new take on what "product-led growth" means from this podcast episode

Sep 2, 2022 • 1h 4min
The great re-org
Topics:LACRM had a great growth month in August, mostly because of expansion revenue.JD, Rick's business partner, is doing a great job.Rick is oscillating between investing in more resources and staying focused.Rick gives an update on his recent local marketing blitz.Tyler is rethinking the customer onboarding flow.LACRM is shifting around their marketing priorities.Rick shares some wisdom from Jason Lempkin.Rick is learning how it's hard to not have authority.Tyler talks about hollow abstraction by mostly just parroting what's said in this video.We talk about "Zucking" (please don't look it up on Urban Dictionary, we're not talking about that kind of Zucking).

Aug 19, 2022 • 59min
Is SaaS getting harder?
Topics this episode:Summer is ending at LACRM and things are going back to normal.Rick attended a company offsite last week, and now he's behind.LegUp Health is planning a local marketing blitz.Tyler gives an update on pay transparency at LACRM.Tyler has been doing some cold outreach to try to find API partners.There's a new VP at Lucid.Tyler talks about how this episode of Default Alive has an interesting take on no-code.Tyler and Rick talk about how it seems like it's getting harder to build a SaaS business, largely inspired by this episode of Out of Beta.