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Startup to LastCan Rick’s optimism defeat Tyler’s pessimism?In this episode, we once again talk about AI, and oh boy do we get off topic.Here's the AI tool Rick mentioned for recording your screen (we'll talk about that in a future episode)Here's the AI report Rick mentioned
2025-12-0449 minStartup to LastSIP trunksIn this conversation, Rick and Tyler explore various topics ranging from smoking techniques and the evolution of grilling methods to the challenges and benefits of a four-day work week. They discuss business growth strategies, particularly focusing on customer retention and the importance of securing renewals. The conversation shifts to the technical aspects of VoIP systems, including SIP trunking, and the implications of AI on search optimization. Finally, they delve into potential new product opportunities and the strategic considerations of acquiring existing products to enhance their offerings.
2025-07-0448 minStartup to LastAdd-on productIn this conversation, Rick and Tyler discuss various topics ranging from their beverage preferences to the latest trends in podcasts, business growth, and the integration of AI in their operations. They explore the significance of setting revenue goals, the role of AI agents in customer outreach, and the development of internal tools to enhance efficiency. Additionally, they delve into potential new product opportunities, customer feedback, and pricing strategies for future offerings, concluding with reflections on their business direction.TakeawaysTyler prefers soda over coffee for his morning routine.Rick has re-engaged with podcasts, discovering new content...
2025-06-1954 minStartup to LastAcquisition vs ExpansionIn this conversation, Tyler and Rick discuss the challenges and adjustments of parenthood, particularly Tyler's experience as a new father. They explore the balance between work and family life, the dynamics of business growth, and the implications of freemium models in their respective companies. The discussion delves into the importance of customer retention versus acquisition, the value of free users, and the efficiency required in service-heavy business models. Throughout the conversation, they share insights on navigating these complexities while maintaining a focus on long-term success. In this conversation, Tyler King and Rick discuss various topics including the implications of...
2025-05-2252 minStartup to LastVibe codingIn this conversation, Tyler King shares his experiences as a new father while balancing work responsibilities. The discussion transitions into Tyler's recent work on LegUp Health, focusing on the challenges and opportunities in building a health insurance platform. They explore the concept of 'vibe coding' and how AI is reshaping software development and content creation. The conversation concludes with a brainstorming session on packaging benefits for LegUp Health, emphasizing the importance of clear communication and demonstrating value to potential clients.TakeawaysFatherhood brings unexpected challenges and joys.Work-life balance is crucial for new parents.
2025-04-2657 minStartup to LastLooking back at 2023 and forward to 2024This is our yearly recap episode!Personal updates from 2023TylerGoals from last year🆗 Take more vacation and make up with with extra work off-hours work🆗 Renovate the houseOther updatesFound a band I like: Caligula's HorseFirst time as an adult I feel good about my exercise routineRickGoals from last year❌ Get weight below 200lbs❌ Write a newsletter most Sundays (27 total)Other updatesBuilt a new house and moved inHad another baby (daughter)Personal goals for 2024TylerMaintain exercise routine: 9k steps/day + 2 rucks/week + 200 pushups/weekFinish house remodelRickRebuild daily exercise and writing habitBe more present with family when I’m w...
2023-12-291h 28Startup to LastReducing FrictionThis week, we discuss how LegUp Health reduced a major point of friction when selling to employers.Here's the full topic list:Rick is finally in his new house, and a major stress has been removed.Rick gives updates on LegUp Health, including a major unlock to getting employers onboard.Rick talks about progress towards hitting annual sales goals.Tyler talks about other ways he's been able to simplify LACRM's operations.Tyler has a coughing fit and we give up early.
2023-10-2734 minStartup to LastExecution eats strategy for breakfast In this episode, we talk about how both of us are refocusing on execution. Here's the full topic list:Tyler is trying to focus everyone at LACRM on the top priorities including:Having the devOps team do a bit more normal software engineering work.Offering customer service people a chance to work on marketing and sales.He himself is starting to code again.Rick explains how LegUp Health is focused on execution and it seems to be working.Rick/JD hired a sales coach.Rick talks about what he learned from the book Amp It Up.Tyler poorly e...
2023-08-1548 minStartup to LastYou can't optimize nothingIn this episode, we talk about how much optimization should be done before you have demand generation figured out.Here's the full topic list:Rick is back from parental leave, and he has things to say about what it's like to take care of two kids at once.We discuss what our perfect days look like.Tyler talks about how LACRM had a bit of crunch mode, and how they stayed calm.Rick talks about a sales slump, and what he's doing about it.We talk about how LegUp Health migrated from no-code to full-code.Tyler...
2023-07-0700 minStartup to LastHandling sales tax as a SaaSIn this episode, we talk about what Less Annoying CRM is doing to handle sales tax compliance worldwide.Here are all the topics:Tyler has officially signed the partnership agreement with Rick and LegUp Health!Rick is wrapping up a position/brand/story projectLegUp Health has updated their mission and core valuesThings are a bit hectic at LACRMTyler is considering merging his personal blog back into the LACRM blogLACRM is probably switching from Stripe to PaddleRick shares what he's learned servicing the early LegUp Health group insurance clientsWe talk a bit about ChatGPT and how it...
2023-06-0955 minStartup to LastPivots and renegotiationsIn this episode, we discuss some changes to LegUp Health, the end of Tyler's sabbatical, and more.Topics in this episode:Tyler is back from his sabbaticalLACRM is getting ready to launch a major redesignRick gives updates on how the LegUp Health/Benefits plan has changedBecause of the changes, we renegotiated Tyler's compensation and involvement in the companyTyler talks about the difference building a product that customers don't expect to use regularly vs and every-day productivity tool.Rick gives an update on working with a marketing coachWe talk about Seeyafuture.me
2023-04-231h 04Startup to LastAn inside look at building a new productIn this episode, we talk about the very early stages of building LegUp Benefits, and a bunch of other stuff. Topics:Rick has hired a marketing coach for LegUp, and we discuss how to get the team talking to each other more instead of having everything flow through Rick.Tyler gives some reflections on leaving LACRM for 6 weeks, and the early days of his sabbatical.Tyler describes a new positioning idea at LACRM.We discuss the early work on LegUp Benefits including customer validation and learning a new tech stack.Rick gives an update on his n...
2023-03-2357 minStartup to LastHow to win against well-funded competitors In this episode, we talk about how bootstrappers can win against companies that have raised massive amounts of money.Full topic list:We give an update on the compensation negotiations we discussed last episode. We've agreed on terms for Tyler to work for Rick on LegUp Benefits!Rick had his first annual offsite and shares a ton of great learnings.LACRM had a great month in February. There was absolutely nothing to learn from it.LACRM's major redesign is getting closer.Rick has streamlined bookkeeping and other financial tasks to save time.Tyler is thinking through w...
2023-03-031h 04Startup to LastThe one where we negotiate Tyler’s compensationIf you’ve been following along, you know that Tyler is about to temporarily join Rick’s startup to help build their new app. In this episode, we talk about the compensation proposal Rick just came up with. Full topic list:Rick already has a new group insurance client after deciding to give that a shot in the last episode.JD is visiting Rick in Utah next weekend.Tyler is having success with delegation, and finds himself with a lot of unstructured time on his hands......and Tyler is having to re-learn what to do with unstr...
2023-02-171h 05Startup to LastHow we deal with security questionnaires In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more.Topics in this episode:Tyler shares his experience at Big Snow Tiny ConfTyler is getting ready for a sabbatical which means delegating a lot of work to other peopleRick talks about gather customer profiles at LegUp HealthRick explains what "aged leads" areWe discuss whether or not it makes sense for Rick to go after group health insurance clientsTyler talks about an LACRM company traditionLACRM launched their Zapier integration!Tyler is preparing to do more design w...
2023-02-031h 03Startup to LastSomething new to announceTopics this week:Tyler is going to work with Rick to build the new LegUp Benefits SaaS productRick has officially transitioned LegUp to 2023Rick talks about how Airtable Interfaces are usefulRick talks about an annual retreat with JD, and we discuss rituals and traditionsTyler is going to Big Snow Tiny ConfLACRM launched their new API, and are almost ready to launch Zapier integrationWe talk about the value of podcasting
2023-01-201h 01Startup to LastLooking back at 2022 and forward to 2023Personal 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-i...
2022-12-311h 44Startup to LastBig bets vs small betsTopics 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 a...
2022-12-131h 05Startup to LastHow 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
2022-12-021h 00Startup to LastAn opportunity that comes along once per yearTopics 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...
2022-10-281h 00Startup to LastWhat'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...
2022-10-1454 minStartup to LastHow much to spend acquiring a customerTopics 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...
2022-09-1659 minStartup to LastThe great re-orgTopics: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...
2022-09-021h 03Startup to LastIs 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...
2022-08-1959 minStartup to LastSingle points of failureTopics in this episode:LACRM got DDoSed *again*Rick went to some networking eventsTyler is ending his newsletterRick gives a chamber of commerce updateLegUp Health is seeing early success with an incentive offerWe discuss handling an employee who leaves for an extended period and whether the goal should be to have no single points of failureRick talks about how intentional assumptions can combat fearTyler gives an LACRM product-led growth update
2022-07-291h 05Startup to LastHealthy urgencyTopics this week:Tyler thinks he's finally fixed his audio setup.Rick and Tyler are both having good sales months. Rick actually knows why!We discuss what indicators a SaaS company might look at to tell whether a recession is impacting their business.Rick is getting weekly updates from JD in a new format that is working well.Rick went to a fancy-pants senator's house to schmooze with the big wigs and now he wants to meet more powerful people so that they can laugh at us common folk.Tyler talks about the possibility of LACRM expanding into...
2022-06-291h 06Startup to LastPrioritizing effectiveness over efficiencyTopics from this episode:Rick has learned more about how to be a good business partner.Rick is prioritizing effectiveness over efficiency.Tyler asks about how best to track marketing ROI.Tyler has an idea for a platform play at LACRM.Another company in LegUp Health's space has been aquired.Tyler gives an argument against delegation.Rick revisits the importance of buffer.Tyler recommends listening to this episode of the IndieHackers podcast.
2022-06-1058 minStartup to LastCharge LessTopics from this episode:Rick is working on updating and simplify LegUp Health's messaging.LegUp Health is testing out purchasing leads.Rick talks about the next step of his SEO work.Tyler has been listening to customer interviews and learned some things about pricing and features with LACRM.Tyler isn't listening to as many business podcasts.We discuss the blog post: We Need A Middle Class For Startups
2022-05-2750 minStartup to LastMission, Vision, and ValuesTopics 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
2022-04-1553 minStartup to LastTools don't solve problemsTopics 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...
2022-04-0157 minStartup to LastPutting together a growth planTopics 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...
2022-03-181h 04Startup to LastThe importance of patience and impatience when hiringTopics 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...
2022-03-0159 minStartup to LastFunding your startup with a day jobTopics this week:Rick is close to finalizing a partnership agreement with his first team member.Tyler is excited that LACRM has been shipping a lot of product improvements lately.Tyler has a new productivity hack he's trying.LegUp Health is doing some cold outreach and so far it's working.LegUp Health joined a new business association.Tyler is nervous about some marketing trends even though they haven't become a problem yet.NFTs. What are they? Why aren't we able to understand them? Why do we keep talking about them despite not understanding them? Because we're podcasters so...
2022-02-1557 minStartup to LastRebirth / Welcoming 2022This 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 righ...
2022-01-211h 24Startup to LastThe final episodeThis 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...
2021-08-1852 minStartup to LastSustainability starts with planningTopics 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.
2021-08-1153 minStartup to LastHome runs vs. consistencyTopics from this episode:Tyler hit 2,000 Twitter followers, and we discuss how Twitter is a hits-based business which doesn't suit Tyler's strengths.Rick gives an update on his personal website and newsletter optimization efforts.Rick reached the first page on an important search term.Less Annoying CRM is tweaking the format of help articles to appeal more the the easily distractible internet user.Rick has finished his javascript course.Tyler discusses the LACRM product roadmap.
2021-07-2741 minStartup to LastThrowing things at the wall to see what sticksTopics this week:Tyler had fun with a once-per-year football bet, and Rick had to put in a full day of dad duty.Tyler is considering taking the ShiftNudge design course to get better at design. He also purchased a license to Tailwind UI so he can copy from better designers.LACRM is tweaking it's policy that everyone at the company must do an hour or support each week.Rick reflects on the value he gets from both writing and reading personal newsletters.LACRM is tweaking it's policy around employee conversation, partially based on a conversation we had...
2021-07-211h 00Startup to LastThe thing about utopias is that they're not realTopics this week:Rick launched LegUpBenefits.com.We discuss Rick's new no-code tool: Outseta.Less Annoying CRM has a new developer starting next month.Tyler has refined his approach to writing internal documentation, and Rick makes a fantastic analogy.Tyler's co-founder/brother will be in town next week.Rick wants to keep practicing coding so his skills don't deteriorate.Rick is taking a break from podcasts.Tyler wants Rick's help to teach the coding fellows about no-code use cases.We discuss Rick's notes on Anything You Want which leads to a conversation about whether startup utopias are real.
2021-07-141h 01Startup to LastSharing profit with employeesTopics this week:Rick took some time off, but is wondering if he earned it.Tyler wrote five blog posts in one day, and wonders if this should be the new approach to blogging.Rick decided to wait for Memberstack updates before taking on a coding project he was planning.Rick is using Outseta for his next technical project to diversify away from Memberstack. He plans to have the done in the next week.Rick is still waiting to decide how to handle the API vendor that closed down his account.Tyler is diving into design and is...
2021-07-0753 minStartup to LastWhen platform risk goes wrongTopics in this episode:Tyler was interviewed to be on Mixergy, but didn't think he did a great job.Rick is adjusting his routine now that he has a kid to take care of.Rick enrolled in a new javascript course to hone his skills.Tyler's previous positive results converting website visitors to his newsletter have turned to failure. No one is signing up.Tyler attended Less Annoying CRM's first leadership team meeting.Tyler had his first person finish building a website based on his online course.Tyler (geez, enough with updates from Tyler, right?) is thinking through...
2021-06-301h 02Startup to LastWhen churn and word of mouth cancel each other outTopics this week:Tyler has a new iPad and doesn't know what it's good for.Rick has added a client through word of mouth, and we discuss how churn and word of mouth are constantly battling with one another.Rick has resolved a major issue one of his clients had with their dental insurance. Crisis averted.Tyler has been working on the wrong things, and is trying to correct that.We discuss Less Annoying CRM's new leadership team.Rick is applying his new javascript skills to his Airtable data.Tyler is writing blog posts in a new way...
2021-06-2346 minStartup to LastWhat we've learned about podcasting after 100 episodesTyler has a new mic.Tyler is in the middle of the final round of interviews for his new dev hire, and he's starting to plan onboarding.We discuss whether to put a new LACRM content project on the main lessannoyingcrm.com domain, or a separate mini-site.Rick finished taking his javascript course.Rick's dad is in town, and he's taking a bit of time off work.We discuss a trick for getting people to complete online courses.We reflect on what we've learned after recording 100 episodes of this podcast.
2021-06-161h 03Startup to LastContent marketing: Putting all our eggs in one basketTopics covered this week:We selfishly discuss larger themes we've covered on the podcast which might make for good topics on the Indie Hackers podcast.Tyler's newsletter signups have increased since changing the call-to-action.Rick lost another LegUp Health client due to unavoidable churn.Tyler has a content idea centered around CRM pricing.Tyler wants to do engineering as marketing but doesn't have any good ideas.Rick is almost done learning javascript.Rick has his first coding projects lined up.We discuss the new Stripe payment links.We revisit last week's topic because a listener called in with...
2021-06-0954 minStartup to LastWhat does a $100k/year support person look like?Topics this week:Tyler asks Rick how he configured the call-to-action for his newsletter on his blog.Tyler is adding a curated list of links to his newsletter.Tyler overcame writers block and wrote his first support-focused blog post.Rick is curious what a highly-compensated support rep might look like at LegUp Health.Rick started paying for Notion.Tyler gives a shout-out to SavvyCal.We take a listener question about how to reach customers who don't have online communities.
2021-06-0252 minStartup to LastCan a course business succeed even if no one finishes them?Topics in this episode:Apparently online courses have a very low completion rate, but maybe that's ok?Rick is learning more about javascript and has a few questions.Rick is taking a vacation where he'll fully unplug.Tyler gives some learnings from the recent enterprise deal that LACRM closed.Tyler has the interview process figured out for LACRM's next hire.
2021-05-2538 minStartup to LastWhen customer expectations aren't metTopics this week:Rick crossed 200 subscribers for his personal newsletter.Rick gives an update on some recent milestones related to this podcast.Rick has been doing Wes Bos's beginner javascript course and is learning a lot.Tyler is on vacation, and is mostly just taking it easy.We discuss Notion's new API.Rick seriously sprained his ankle.Rick is dealing with a customer who is disappointed.
2021-05-1441 minStartup to LastThe Theory of ConstraintsTopics this week:We're using a tool called ZipMessage to collect listener questions. If there's something you'd like us to discuss on the podcast, leave us an audio recording of your question at zipmessage.com/tylerLess Annoying CRM had a good April.LACRM's average account size is going up slightly, but it's having a significant impact on revenue.We discuss the theory of constraints, and how Rick can apply it to his next project.We talk about interviewing software engineers, especially when people with different experience levels will be applying for the same position.Rick finished a book...
2021-05-071h 04Startup to LastThe importance of internal communicationTopics 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.R...
2021-04-301h 07Startup to LastEmpowering employees to be leadersTopics 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...
2021-04-231h 03Startup to LastTime managementTopics 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.
2021-04-1655 minStartup to Last$2k MRRTopics 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.
2021-04-0956 minStartup to LastBurnoutTopics 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...
2021-03-1856 minStartup to LastWhat 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.
2021-03-0555 minStartup to LastContent marketing when you're not a domain expertTopics discussed this week:Rick is learning more powerful no-code tricks with Zapier, and advancing his PHP knowledge.We discuss the best way to learn how to write secure code.Tyler is wrapping up a big project which involves setting deadlines. We discuss healthy vs. unhealthy deadlines.Tyler is brainstorming content marketing approaches which is tough because he's not an expert on the topics his customers are most interested in.We discuss Rick's learnings from Peter Drucker.We talk about the idea of running an online competition
2021-02-191h 04Startup to LastGetting marketing ideas from Hubspot's acquisition of The HustleOther topics this week:Rick officially launched a "give back" programRick decided not to post internship openings until post-parental leave.Rick wants to start a group focused on reaching local consumers.Tyler is planning an at-home retreat.Morale is a bit low as covid drags on.We discuss a specific UI decision LACRM is facing.We discuss aligning what you want to have happen with what will actually happen.
2021-02-051h 01Startup to LastThe paradox of successOther topics this week:How Robinhood's recent controversy applies to Rick's business model.Rick received his first cancelation.Twitter acquired Revue.Rick is working on a low-code solution to an automation issue.Tyler is close to closing a deal with an enterprise client.We discuss how to handle security audits (e.g. SOC 2 compliance) with enterprise customers.
2021-01-2957 minStartup to LastIs building an audience worth it?Other topics this week:Less Annoying CRM hit $3 million ARR, and the tweet about it got a lot of engagement.Rick paid out referral rewards to his clients.Rick explains his buyer journey exercise.Rick reflects on the value of customer appreciation.Tyler has been a guest on several other podcasts.We discuss how to react when a competitor launches.We discuss the idea of building buffer into everything we do, and how it relates to the startup to last philosophy.
2021-01-221h 03Startup to LastThe future of no-codeOther topics this week:Tyler reviews what he learned from last week's DDoS attack.Rick has planned out the year and feels good about his ability to get it done.Rick is allocating 50% of his time to promotion and 50% to automating his product.Tyler is about to start teaching a design course.LACRM is close to finishing a migration to Webflow.We discuss Clubhouse.Tyler is getting a Peloton.Rick is experiencing anti-depressant withdrawal syndrome.
2021-01-1557 minStartup to LastEnd of 2020 mega-episodeLooking back at 2020Note, many of the goals mentioned here were set in our 2019 recap episode.Personal accomplishments Rick 2019 Goal: Get to a point where he and his wife feel comfortable having kids - ✅ Not only are they ready, Rick's wife is pregnant 🎉2019 Goal: Increase level of play - ✅ He's been playing basketball, skiing, playing water sports, etc.Had success writing his newsletter almost every week.Tyler 2019 Goal: Get a dog - ✅ His name is jolo and he's an idiot.2019 Goal: Exercise three times per week - ❌ Things were looking good until covid hit.Got married and bought a h...
2021-01-011h 32Startup to LastShould your startup donate to charity?Other topics:Tyler realized he might have more revenue growth next year than he originally thought.Rick is learning that things don't die down immediately after open enrollment, and that's making it hard to do end-of-year planning.Tyler has been thinking about what the approach might be when LACRM re-opens the office.Rick is meeting his intern for the first time in-person.Rick switched to Notion and is loving it.Tyler has a marketing approach that he wants feedback on.We discuss whether companies should donate money to charities.
2020-12-251h 04Startup to LastProduct Market FitOther topics from this episode:Rick is finished with open enrollment and walks through some metrics.Rick is expecting his first churn from customers who signed up earlier this year.Rick realizes that word of mouth happens at specific moments in time, such as when someone leaves their job, gets married, or has some other life event.Tyler is learning more about his strengths and weaknesses.Tyler is overwhelmed with interviews.Tyler is preparing a presentation on recruiting and diversity.I would like to apologize for my lack of creativity in the sentence structure above. It's the...
2020-12-181h 12Startup to LastTraction vs distractionSome 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...
2020-11-201h 03Startup to LastSetting goals when you're just getting startedOther 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.
2020-11-131h 05Startup to LastHow big to go when moving upmarketOther 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.
2020-11-061h 06Startup to LastStartup community fatigueSome 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...
2020-10-291h 06Startup to LastBuilding a moatHere'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...
2020-10-091h 04Startup to LastShould multiple products share a single brandHere 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?
2020-10-021h 01Startup to LastAll-nightersHere 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).
2020-09-2559 minStartup to LastPricing annual plans when users are added mid-yearHere 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 b2...
2020-09-111h 05Startup to LastNetworking without being annoyingHere 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...
2020-08-2859 minStartup to LastWhat 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.
2020-08-211h 01Startup to LastHow college students can prepare for entrepreneurshipHere 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.
2020-08-141h 04Startup to LastThe Sims, but way more boringHere 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...
2020-08-071h 03Startup to LastAsking for too much info during signupNote from Tyler: I'm sorry that my dog is whining in the background throughout this episode. I'll banish him from my room in future episodes. He's such a wimp.Here are some of the topics from this episode:Tyler's price increase went into effect, but it's too early to draw any conclusions.Rick has gotten great feedback from sharing his slide deck.Tyler has been tweaking how his team communicates remotely.Rick has heard from his early customers that he's asking them for too much info, but it's necessary for him to provide them with service...
2020-07-241h 04Startup to LastBuilding trust when you're an unproven businessTopics discussed in this episode:Tyler's growth is still going strong.Rick is going to write content to build trust with his early leads.Rick created a slide deck to explain his business. Check it out here and let him know what you think.Tyler is making long-term product decisions.Tyler is thinking about making no-code a core part of the coding fellowship next year.Rick recorded an interview with Memberstack which will be featured on their site.Tyler is going to invest in Earnest Capital.Rick had to give advice about how to come up with an...
2020-07-1759 minStartup to LastWinning awardsHere are some topics from this week:Less Annoying CRM was named the #1 CRM by U.S. News and World Report.Tyler restarted employee raises after temporarily freezing them when the pandemic started.Rick now has fully self-serve onboarding.We discuss how to write a terms of service and privacy policy.Rick is making trade offs between sales and product time.Rick wants to retain some of his interns after the summer.Rick has validated that real estate is a good customer segment and is planning next steps.
2020-07-101h 03Startup to LastA price increase is comingTopics from this week:Tyler talks about the reaction he got when telling his customers about an upcoming price increase.Rick launched his referral program.Tyler is working on a new API for LACRM.Rick has finalized the interns he'll bring on this summer.Rick wasted a bunch of time talking to the IRS about a notification that was sent in error.We discuss HEY, the new email program from Basecamp.
2020-06-2659 minStartup to LastCuriosity or convictionHere are the topics from this week:Tyler and Rick both have interns and need to figure out what projects they should be working on.Rick has been working on a client referral program.Tyler is wondering if there's anything for him to do to partner with customers who love LACRM.Rick was considering an intrapreneurship opportunity (working as an entrepreneur within a larger company) and decided against it.Tyler is struggling to prioritize product improvements.Less Annoying CRM will need to raise prices at some point. Tyler is wondering if now is the right time.
2020-06-121h 01Startup to LastWeighing optionsHere are some of the topics we covered this week:Tyler's interns started and they're keeping him busy.Rick took a vacation over Memorial day weekend and feels refreshed.Tyler has been brainstorming his product strategy more since last week.Tyler gives an update on how May has been for Less Annoying CRM financially.Rick has added his first non "beta" client.Tyler used GDPR to get a company to delete some data.Rick has a new professional opportunity that would come at the expense of LegUp Health.We discuss the merits of masterminds and talk about the...
2020-05-291h 01Startup to LastFirst revenue in the bankHere are some of the topics we discussed this week:Rick made his first revenue with LegUp HealthTyler pimped out his home office with a new chairRick is using Heap for product analyticsLess Annoying CRM had a "CRM Coach day of rest" where developers handled support for the dayRick's intern has started and is already paying offTyler has a new framework for thinking about product improvementsWe discuss how several tech companies are moving to a more permanent remote work model
2020-05-221h 00Startup to LastThe interns are comingHere are the topics we covered this week:Tyler got a new standing desk.Rick hit a wall with his product.Both Rick and Tyler have interns starting soon. There's a lot of work to do to prepare.Less Annoying CRM had a breakthrough with their demo call workflow.Rick learned from the wisdom of Charlie Munger.Tyler is thinking about analytics because of a fan suggestion.LegUp Health got their first user referral.
2020-05-1550 minStartup to LastIt's all about the updatesWe tried out a new format in this episode. Instead of picking a deep dive topic and spending most of the time on that, we both had a lot of updates to give, so we spent the entire episode on that. Here are some of the topics we covered:Rick finished a project for a consulting client that probably won't get used. He talked about how deflating that feels, and how managers should be careful when doing this to employees.Less Annoying CRM just received money through the PPP and we discuss what should be done with the...
2020-05-0855 minStartup to LastRunning one-on-one meetings with employeesThe main theme of our discussion was that it's important to understand the objectives of any meeting. Rick helped Tyler narrow the list of objectives down, and now Tyler needs to (1) consider which objectives are most important to him, (2) consider if some of the objectives are being met in other ways so they can be left out of the meeting, and (3) communicate the objectives to employees prior to each meeting so that they can understand what's expected of them.
2020-02-1458 minStartup to LastLooking back at 2019 and forward to 2020This week, we wanted to take some time to reflect on what happened in 2019 and set goals for 2020. We created a series of questions that Rick and Tyler both had to answer. Here are the answers...What happened in 2019?In our personal livesRick: Took 7-8 months of to figure out who he is and what his goals are, especially with his new marriage.Tyler: Figured out a sustainable dietIn our professional livesRickFigured out what he wants to do after leaving his previous job of 11+ yearsStarted LegUp Ventures which is a holding company for his various ventures:GroupCurrent...
2019-12-2659 minStartup to LastThe role of emotions in businessIn this episode as part of some research for his next book, Rick interviews Tyler about his experience with emotions in the Less Annoying CRM workplace. Here are some of the takeaways:There are frameworks out there for emotional intelligence, self-regulation, but there isn’t much stuff out there about how emotions impact company culture, team performance, and leadership.There aren’t a ton of CEOs talking about their own experiences.Most of the stories out there are from therapists about their anonymous clients.There isn't agreement on the definition of emotion.One model is Robert Plutchik’s wheel...
2019-12-0659 minStartup to LastShould you consult on the side while launching a startup?In this episode, Rick seeks Tyler’s advice on how to approach consulting on the side to fund LegUp Ventures. Here are some of the takeaways:If you need the money, you’ve got to consult or get a jobAin’t no way around itConsulting can be preferable as you have way more flexibilityIt's way easier to bootstrap with consulting as your source of money versus a full time jobYou hourly rate as a consultant might be higher alsoBe proactive about consulting.(Don’t want until you need the money)View consulting as protection for your business —> it will help...
2019-11-2255 minStartup to LastResetting stakeholder expectations when things change at your businessIn this episode, we discuss how to reset expectations with stakeholders when things change. Rick shares a challenge he is facing at one of his companies. While we worked through a specific situation, the general concept applies often. Here’s the general framework that emerged:Clarify what needs to change and whyFrame the problem(s) thoughtfullyIdentify the stakeholders and where do they standIdentify who has decision-making authority and who can be an allyDecide who to talk to first and iterate from there as a teamBe open to feedbackGet everyone aligned and move forward togetherBe aware of fundamental differences; th...
2019-10-1158 minStartup to LastInterview with Rick Lindquist, founder of LegUp VenturesHere’s what you should know about Rick:Born in Raleigh, NC and grew up in Morganton and Charlotte, NCWent to college at Duke UniversityMajored in Economics and Computer ScienceWrestled at DukeMoved to Park City to Ski bum in after graduationMet Tyler at a startup called Zane Benefits (which is now part of PeopleKeep) in 2007Became the President of Zane Benefits after a mass layoff in 2008Bootstrapped Zane Benefits to $4+ million in annual revenue in 2013/2014After a regulatory threat in 2013, launched a new business called PeopleKeepRaised ~$3M in venture capital to finance thisWrote a book in 2014 which was pu...
2019-10-0434 minStartup to LastHow to recruit internsThis episode ended up being much more about how to increase workforce diversity than how to hire interns. Here’s a quick rundown: Tyler and his team at Less Annoying CRM want to increase diversityThey primarily source candidates via their summer internship programTyler and his team have had great success at WashU with this modelHowever, this has led to a lack of diversity across his 17 employees (~50% went to WashU)Tyler wants more internships to come from schools other than WashUDespite effort, Tyler has not been able to replicate the internship funnel at other schools in MissouriE.g. He’s tri...
2019-09-2750 minStartup to LastInterview with Tyler King, co-founder and CEO of Less Annoying CRMHere’s what you should know about Tyler:Grew up in St. Louis, MissouriWent to college at Washington University in St. Louis (“Wash U.”)Majored in Computer ScienceBecame a web developer through side projects and internshipsPlayed guitar in a heavy metal band called Embers Rise (listen here)Left his Masters program early to join a startup called Zane Benefits (which is now part of PeopleKeep) in Park City, Utah Met Rick at Zane Benefits in 2007Survived a lay-off with Rick in October 2008 and became head of productWorked with Rick to pivot the business model to get to cash flow po...
2019-09-2037 minStartup to LastHow to market a podcastIn this episode, we talk about why we started the podcast, who we think our ideal listener is, and how we plan to grow our audience.After going back and forth, the following framework emerged for marketing a podcastWhy did we start the podcast?Who is our audience and ideal listener?What problem are we solving for our audience?What makes our podcast unique?How will we measure success?How will we achieve success?Takeaways include: Our ideal listener is someone who:Wants to achieve freedom through entrepreneurshipWants to build something sustainable that w...
2019-09-0655 minStartup to LastHow to teach yourself to code a web-based applicationIn this episode, Tyler helps Rick create a plan to teach himself how to code a web-based application. Rick isn’t sure where to start and asks Tyler for help. Tyler shares best practices he’s learned from teaching more than 15 people how to code from scratch. After going back and forth, the following framework emerged for teaching yourself how to code a web-based application:Clarify why you want to learn how to code.Get a macro understanding of the skills, languages, and technologies you need to know in order to build an application. Pick a simple...
2019-08-3050 minStartup to LastHow to communicate major product changes to your usersIn this episode, Rick helps Tyler think through how to roll out a major product redesign for his 20,000 users. Tyler has a plan, but he’s concerned about losing customers through the transition. His biggest roadblock is figuring out how to roll this out without causing his customers to get angry and leave.After going back and forth, the following framework emerged for communicating major product changes to existing users:Why you are making the product changes in the first place?How will you measure success (i.e. the desired outcome)? What are the key messages you...
2019-08-2350 minStartup to LastHow a non-technical founder can make their first technical hireIn this episode, Tyler helps Rick evaluate how to build a new software application from scratch. Since Rick is a nontechnical founder, his biggest roadblock is figuring out how to build the application without raising money.After going back and forth, the following framework emerged for nontechnical founders trying to hire a first employee:What is the idea (i.e. problem and solution)?What type of application needs to be built to deliver on the idea (i.e. requirements)?What technical skills are required to build the application?How much are these skills going to cost...
2019-08-0954 minStartup to LastHow an employee handbook can help with recruitingWhat’s an employee handbook?Tyler: The topic this week is employee handbooks. This has been on my mind because we redid our whole employee handbook this last spring leading up to hiring some new people. So I rewrote it and put a lot of thought into it, but I wanted to talk through it with you. I'd like to cover things like what should actually go into it. And one thing that I hadn't thought of prior to now is when and how should the information in an employee handbook be communicated. What we us...
2019-08-0246 minStartup to LastWorking remotely vs. working in an officeTyler: In this episode, we're gonna talk about the pros and cons of remote work, such as when does it make sense for a company to have employees altogether in an office versus fully remote or something in between.Rick: I personally get this all of the time. I've heard of four core models that . One is “single site” which means everyone works in the same office environment. Second, is “multi-site” where you have multiple locations with everyone working within the office. And then the third is “satellite”, in which most of the team is together, but a few people...
2019-07-2644 minStartup to LastThe role of a CEOThe role of a small business or startup CEOTyler: In this episode, we're going to talk about what the role of a CEO should be at a small business or a startup. I always hesitate to call myself a CEO, depending on who I'm talking to because it seems a little pretentious. I run a 17-person company and some days, I don't do any CEO stuff: I just write code or design something. And some days I'm in meetings and brainstorming long term product vision and I feel more like a CEO. I'm a...
2019-07-1949 minStartup to LastImpostor syndrome and fear-based decision makingTyler: In this episode, we're going to talk about impostor syndrome. Do you want to kind of explain what you had in mind here?Rick: Yeah. So you know this. I left PeopleKeep after 11 years. For most of the time, I was the leader of the company under various titles, most recently CEO. I left in October. So it's been about nine months now.Rick: One of the big reflections I had was sometimes how I treated people. Sometimes I was super impatient with people and put certain immediate business goals over...
2019-07-1140 minStartup to LastSalary transparencyIn this episode, we discussed salary transparency. After some back and forth, we concluded that a company’s salary transparency policy should be based on its personnel strategy. In other words, how you handle salary transparency, whether it's no transparency, partial transparency or full transparency, entirely depends on the people you have and more importantly the people you want to attract.Before you decide on a compensation strategy, you should identify the people you need to hire to execute your business plan. This includes what the job functions are and who you want to recruit. If some ve...
2019-06-2939 min