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...

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 del...

 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 Conf Tyler is getting ready for a sabbatical which means delegating a lot of work to other people Rick talks about gather customer profiles at LegUp Health Rick explains what "aged leads" are We discuss whether o...

Topics this week: Tyler is going to work with Rick to build the new LegUp Benefits SaaS product Rick has officially transitioned LegUp to 2023 Rick talks about how Airtable Interfaces are useful Rick talks about an annual retreat with JD, and we discuss rituals and traditions Tyler is going to Big Snow Tiny Conf LACRM launched their new API, and are almost ready to launch Zapier integration We tal...

Personal updates from 2022 Tyler Goals from last year ✅ Plan for travel as part of relationship  ❌ Build more schedule flexibility  Other updates Figured out personal finance plan with Shelly Rick Goals 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 goals Professional updates from...

Topics in this episode:  LACRM is having a good December Rick is feeling lots of momentum Rick gives an update on LegUp Health's growth Rick is reading the Warren Buffet bio: The Snowball Tyler explains LACRM's new approach to bug triage Rick is thinking about how hard to push for in-person Tyler describes a new shorthand: Following daylight Rick realizes he's learning a lot about digital marketin...

Topics: Rick gives an update on open enrollment Tyler talks about some upcoming product launches including the new Zapier integration Rick is refining his Adwords approach Rick is starting to think about 2023 Tyler talks about project management LACRM had a CRM Coach culture refresh We talk about the recent wave of AI innovation

Topics this week: I mean, Twitter, obviously Rick gives an update on open enrollment including... Sales so far His misadventures with Google advertising Website positioning and design Tyler gives an update on LACRM's integration project LACRM just went through a process that happens every six months We 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 enrollment His goal is to be long-term patient, but have short-term urgency He doesn't have enough traffic for retargeting Outreach will be their main lever This weekend is his chance to get everything ready for November 1st Tyler talks about his time at Founder Summit LACRM is thinking about brand marketing...

Topics this week: Tyler is getting ready for Founder Summit Rick is learning about digital advertising, and we discuss whether tracking people on the internet is a net good or bad thing Tyler gives an update on his NPS saga Tyler talks about a joint webinar he did with ZipMessage Rick describes his chamber of commerce webinar strategy Windfall is opening a Utah office Rick is getting ready to do o...

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!

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 DAD Rick spent a week in Cancun and soaked up some sweet business wisdom Tyler is experiencing a period of calm at work and has done some coding for the first time in a long time LACRM decided not to hire interns next summer Rick and JD planned their marketing blit...

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...

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 ha...

Topics in this episode: LACRM got DDoSed *again* Rick went to some networking events Tyler is ending his newsletter Rick gives a chamber of commerce update LegUp Health is seeing early success with an incentive offer We discuss handling an employee who leaves for an extended period and whether the goal should be to have no single points of failure Rick talks about how intentional assumptions can c...

Topics in this episode: Less Annoying CRM hit $3.5 million ARR. Rick and LegUp Health have signed up for several in-person networking events as well as a number of chambers of commerce. LACRM had a new CRM Coach start. Tyler reflects on why his updates haven't been interesting recently, and what that might mean about how he'd feel running a bigger company. Rick got a new client who followed the id...

Topics 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...

Topics 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 li...

Topics 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 F...

Topics this week The possibility of a recession and how it might impact businesses like ours. LegUp Health just had a competitor acquired. Less Annoying CRM was DDoSed again. Tyler discusses some traction channels he's been considering. Rick asks about virtuous vs. vicious cycles. We discuss the merits of a multi-product business vs a single-product business.

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 wa...

Topics this week: A new employee started at LACRM Tyler is getting ready for lots of interns Rick has been struggling to form healthy habits Rick gives an update on his business partner's work/life balance Tyler finished his cycle of meeting/presentation/1:1s that he does every six months Tyler asks Rick about how to define mission, vision, and values Rick describes a new marketing funnel he found...

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...

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...

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 u...