In 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 developme…

In this conversation, Tyler and Rick discuss various aspects of long-term product strategy at Less Annoying CRM, including personal updates, business growth, customer retention challenges, economic concerns, product development, and the importance of identifying ideal customer personas. They explore the balance between adding features and maintaini…

In this conversation, Tyler and Rick discuss the challenges and triumphs of managing projects within SaaS companies, particularly focusing on the effective use of AI, sales pipeline dynamics, and the balance between calm and chaos in business operations. They explore the importance of setting realistic goals, the role of automation in enhancing use…

In this episode, Tyler and Rick discuss various sales best practices, focusing on the importance of maintaining a clean sales pipeline, optimizing CRM usage, and enhancing marketing strategies. They delve into the challenges of customer service and the need for a consultative approach to selling, emphasizing the value of understanding customer need…

In this episode, we talk about how Rick has given himself some breathing room, and how that’s impacted his outlook on the business.By Rick Lindquist and Tyler King

In this episode, we talk about some metrics that are headed in the right direction. Let’s goBy Rick Lindquist and Tyler King

In this episode, we try to prioritize some of the different growth channels Rick is considering for 2025.By Rick Lindquist and Tyler King

In this episode, we recap 2024 and set goals for 2025: Personal goals for 2025: Rick: Primary theme: Buy back time Take 1 personal day every 1-2 months Get time back for things I love (skiing, basketball, be present on vacations, reading/writing, local networking) Have a familiy vacation on the calendar to look forward to at all times Tyler Baby st…

In this episode, we discuss how there are multiple different approaches to take when a startup needs to grow the team.By Rick Lindquist and Tyler King

In this episode, we discuss Bluesky as the new Twitter, how Rick’s busiest time of year is surprisingly calm, and more.By Rick Lindquist and Tyler King

Less Annoying CRM is working on some big features, and in this episode, we discuss what we’re learning as a result.By Rick Lindquist and Tyler King

We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying.By Rick Lindquist and Tyler King

In this episode, we review our yearly goals, talk about some new AI tools we’re trying out, and more.By Rick Lindquist and Tyler King

In this episode, we talk about how we’re thinking about customer service in a world of AI*, and we do a deep dive into a customer interview Rick did recently. *Clickbait warning: We don't actually spend much time on this topic, I just wanted a catchy title for the episode. Did it work? Did you listen because of my misleading title? Let me know in t…

In this episode, we talk about the value of a podcast community, and generally how we’re trying to protect ourselves from the internet.By Rick Lindquist and Tyler King

In this episode, we talk about about the impact a recent price change is having on Less Annoying CRM’s finances.By Rick Lindquist and Tyler King

The internet loves to talk about whether to focus on a single business or build a portfolio of small bets. I’m sure you’re sick of hearing about it. But in this episode, we have a twist on that topic. For an established business thinking about launching complimentary products, is it better to build one great one, or a series of only ok ones.…

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…