In this episode, we talk about how the job of an entrepreneur isn’t to decide which ideas are good and which are bad. It’s to pick the single best idea out of a sea of good ideas.By Rick Lindquist and Tyler King

In this episode, we talk about a decision Rick needs to make with LegUp Health. Should he treat it like a high-growth startup, or a lifestyle business?By Rick Lindquist and Tyler King

In this episode, we talk about how a lot of startup advice is focused on businesses going from zero to one, and how we have to be careful not to assume that all applies to us.By Rick Lindquist and Tyler King

In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the businessBy Rick Lindquist and Tyler King

In this episode, we discuss using consultants to level up your team.By Rick Lindquist and Tyler King

In this episode, Rick explains how he’s getting more hands on with marketing.By Rick Lindquist and Tyler King

In this episode, we discuss how some lessons can't be taught, they have to be learned through experience. What does that mean for mentoring less experienced employees?By Rick Lindquist and Tyler King

In this episode, we talk about when it makes sense to outsource work to contractors and agencies, vs when it makes sense to do something in-house.By Rick Lindquist and Tyler King

In this episode, we talk about Less Annoying CRM’s latest sales experiment.By Rick Lindquist and Tyler King

In this episode, we talk about takeaways from big snow tiny conf, and more.By Rick Lindquist and Tyler King

In this episode, we discuss how Rick is using the “profit first” mindset to manage company finances.By Rick Lindquist and Tyler King

This is our yearly recap episode! Personal updates from 2023 Tyler Goals from last year 🆗 Take more vacation and make up with with extra work off-hours work 🆗 Renovate the house Other updates Found a band I like: Caligula's Horse First time as an adult I feel good about my exercise routine Rick Goals from last year ❌ Get weight below 200lbs ❌ Write…

In this episode, we talk about Rick's open enrollment experience, and what LACRM is doing related to DEI (diversity, equity, and inclusion)By Rick Lindquist and Tyler King

In this episode, Rick tries to explain to me that there are people who know how to grow businesses, and I stubbornly insist otherwise.By Rick Lindquist and Tyler King

In this episode, we discuss what feels like an inflection point in Rick's business. Full topic list: LegUp Health has a new website. Rick thinks he's feeling an inflection point. We daydream about the future of LegUp Health a bit. Things are calm at LACRM, and the employees are all increasingly experienced. Tyler is coding again. There's a new buzz…

This 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…

In this episode, we discuss whether or not building features customers ask for is a valid path toward growth. Here are all the topics: LACRM has started migrating to Paddle. LegUp Benefits has its first official customer! We discuss how LACRM's free trial pipeline isn't as correlated with paying user growth as you'd expect. We dive deep into the hi…

This week, we talk about a pricing change we recently announced at Less Annoying CRM. We dive into the history behind the decision, how it was communicated, what it means for the finances of the business, and more.By Rick Lindquist and Tyler King

In this episode, we discuss a hodgepodge of things including a company reorg, growth tactics, and more. Here are all the topics: Rick updates us on LegUp Health's progress. He talks about working on the sales pitch, building momentum, staying focused, and more. Tyler is merging two teams at LACRM. We discuss what the impact of that change might be.…

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 …

In this episode, we talk about Rick’s early signs of success getting out a sales rut, and much more. Full topic list: Rick gives an update on how he and JD are getting out of a sales rut. Rick is busy and has absolutely zero free time. Tyler talks about how he's considering web forms and automations as possible features for LACRM. We discuss an alt…

In 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 m…

In 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 project LegUp Health has updated their mission and core values Things are a bit hectic at LACRM…

In this episode, we talk about Less Annoying CRM’s producthunt launch, and a lot more. Here's the full topic list: Tyler takes a look back at LACRM's growth history, and explains their new approach to growth. Tyler explains how the recent Product Hunt launch went. Rick has cleared a lot off his LegUp Health plate and is starting to focus on new typ…

In 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 sabbatical LACRM is getting ready to launch a major redesign Rick gives updates on how the LegUp Health/Benefits plan has changed Because of the changes, we renegotiated Tyler's compensation and involveme…

Come on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules.By Rick Lindquist and Tyler King

In 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 o…

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…

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 Ut…

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 ex…

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 ar…

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) …

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 re…

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…

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 Foun…

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 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!By Rick Lindquist and Tyler King

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 ne…

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 th…

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. Tyle…

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 …

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 …

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 fan…

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 revi…

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. …

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-produc…

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 i…

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 val…

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 gr…