Startup to Last

Topics in this episode:Tyler bought tickets to attend Founder Summit.Tyler is rethinking his investment strategy.A competitor of LegUp Health is going out of business.Tyler is working on renewing LACRM's office lease.LegUp Health is struggling to scale their outreach, so they're going back to basics.LACRM's new design is coming along.LACRM is making pay more transparent internally.Rick wants LegUp to be in the discussion when people talk about health insurance in Utah.We discuss how to provide mentorship to employees if no one at your company has expertise in the area they need help with.We discuss what future marketing channels might be similar to what SEO was in the early 2000's.

Topics this week:A new employee started at LACRMTyler is getting ready for lots of internsRick has been struggling to form healthy habitsRick gives an update on his business partner's work/life balanceTyler finished his cycle of meeting/presentation/1:1s that he does every six monthsTyler asks Rick about how to define mission, vision, and valuesRick describes a new marketing funnel he foundLegUp Health's vision is supported by a recent regulation change

Topics this week:Tyler has been extremely busy with meetings, interviews, etc.LACRM hired two new CRM Coaches.Rick took some time off to ski with his family, watched a Duke basketball game, and celebrated his son's 1st birthday.LegUp Health has mixed results sending cookies to try to delight customers.Tyler gives some updates on product-led growth brainstorming from last episode.LegUp Health added some new tools to their workflow to start making things more efficient.Rick warns us about the dangers of thinking that tools solve problems.Tyler is in discussions with DemandMaven.Tyler isn't sure what the future of his blog/newsletter should be.We talk about how to be real without being rude.

Topics from this week:Tyler explains how bug bounties work.Rick discusses the power of incentives.LegUp Health is adding new clients every week, and we discuss how prospecting is working.Rick brags about his new X1 credit card (I swear this isn't sponsored, we don't have nearly enough listeners for anyone to bother paying us for product placement)We discuss how Rick can thank people who help his business.No-work Sunday is a success for Rick.We discuss Jason Cohen's blog post: The Elephant in the room: The myth of exponential hypergrowthRick helps Tyler think through his new growth plan.

Topics this week:Tyler is reading The Great CEO Within.Rick shares some early sales wins.LegUp Health is learning about their ICP (Ideal Customer Profile).Tyler has been experiencing ups and downs when it comes to design, but overall has learned a lot the last two weeks.Rick is making Sunday a "no work" day.Less Annoying CRM is hiring, and Tyler thinks there needs to be more of a sense of urgency.Rick has set a quarterly goal, but it's about learning rather than hitting certain metrics.Rick has additional responsibilities at Windfall.Tyler shouts out a few products from Elgato, especially the low-profile mic arm.We compare starting a business when you're younger vs when you're older.Update from last episode: This is the compensation agreement Rick finalized with his first employee.

This episode dives into the balance between a full-time job and startup life, with insights on adaptive compensation models. The hosts share excitement over software enhancements and clever productivity hacks. They explore the odd allure of NFTs and question their underlying value. A listener's query sparks discussion on managing work-life balance amid evolving tech trends. The challenges of marketing strategies and user retention metrics reveal the complexities of navigating a growing business landscape while maintaining clarity and transparency.

Topics this week:Tyler is considering going to Founder Summit in Ashville this fall.LegUp Health signed a partnership deal with Pando Labs.LACRM is on a hiring spree.LACRM has a new thriving wage.We discuss whether video testimonials are a good idea.Tyler heard a podcast which made fun of LACRM's design, and this resulted in him getting some design coaching.We discuss how Rick can structure a partnership agreement with his first hire.

This is our annual retro/goal-setting episode. Here's what we cover:Personal updates from 2021TylerGoal from last year: ✅Spend more time with family and friends once vaccinatedOther updatesStarted exercisingFroze embryosRickGoals from last year✅ Get sleep under control✅ Adjust to being a dadOther updatesWasn't good about exercisingHas only been on one date with SableProfessional updates from 2021TylerGoals from last year✅ Get marketing to a point where if can be delegated❓ Design a new appointment scheduler product✅ Biggest worry: Growth leveling off❓ Want to learn: Re-learn how to iterate and move fastBiggest disappointment: Losing a developer right when the product team was building momentumBiggest learning: Wants to be a product designerOther updates:Fewer management responsibilitiesSigned biggest client to-dateFull-funded the treasuryRickGoals from last year❌ Get to $10k MRR. ✅ Automate/delegate so service can be scalable. ✅ Biggest worry: Being able to scale service. ✅ Want to learn: Learn more coding, especially working with API data and generating dynamic emails.Biggest disappointment:  Not being able to work on LegUp Health full timeBiggest learning:  Sharing the journey at LegUp Health is better than going solo Other updates: Tried bringing on another friend as a Marketing contractor, but he decided to take a full-time job before he ramped up 2022 Personal themes/goalsTylerPlan for travel as part of relationshipBuild more schedule flexibility so things can be done without needing willpower (e.g. exercise mid-day)RickReprioritize daily personal health habits (write/exercise before family wakes up, daily calorie tracking)Spend more quality time with Sable (have a date most weeks) and Oliver (take on errands)2022 Professional themes/goalsTylerTheme: Spend more time working, but on my own termsMake space to do more individual contributor design workOther thingsRelease 3.9 designTwo blog post-worthy releases per quarterBy end of year, have an equal balance of tech debt, core CRM, strategy, and product-led growth work on the dev teamRun the coding fellowshipRickSupport the growth of LeUp HealthStructure a partnership and financial plan that enables JD to go full-timeGrow the business to 400 clientsFully automate the new user onboarding experienceHelp scale Windfall the right way Prioritize both performance and peopleBe a team playerDeliver on my responsibilitiesBiggest worryTyler: Growth slowed in 2021. Will it come back?Rick: Retaining JD for the long termWhat do we want to learn?Tyler: More professional visual designRick: First principles of leading others (e.g. influence, motivation, habits, trust, negotiation, communication, and decision-making)PredictionsLast yearTyler: ❌ San Francisco will become a good place for early-stage startups againRick: ❓ Asynchronous video will become big in professional settingsNext yearTyler: The world will be less interested in speculative bubbles (NFTs, meme stocks, etc.)Rick: VR headset use is going to become as common as playing a Wii

This is our last episode. Thanks to everyone who has listened and supported us over the last couple years. We're going to miss you 😢Topics in this episode:Rick accepted a new job. What does that mean for LegUp Health?Rick finished migrating his help site to Webflow.Rick notified his free users that the free service is shutting down.Tyler talks about compounding and what it means for thinking about the future.We discuss how it might be harder to start a company these days because there are so many success stories that are hard to live up to.We discuss Datafetcher.com as a nice no-code tool.We discuss the build vs. buy tradeoffs.

Topics this week:Rick is canceling his CRM subscription.Tyler is considering where his newsletter fits into his overall plan.Based on our conversation last week, Rick has new clarity around the future of LegUp Health.Tyler explains how LACRM came up with their long-term product roadmap.Rick is going through continuing education.We discuss some touchy feely things related to the passage of time.