Startup to Last

 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 when it makes sense to do custom work for a large client.We tackle a listener question: How do bootstrapped companies compete with funded competitors.

If 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 unstructured time.LegUp Health got hit with a bunch of spam contact forms.Tyler is planning the new office layout for LACRM.Apparently design debt is a thing.Tyler is having trouble getting started on the LegUp Benefits project. Side projects are hard.Rick brings up Youtube Premium, Quora, and NotionAIBig topic: We discuss the compensation proposal that Rick just sent Tyler.

 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 workWe have some rants and shoutoutsWe talk about what to do when a lead asks for security certifications and/or asks you to fill out a questionnaire 

Topics 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

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 

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.

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

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

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

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