Startup to Last

In this episode, Tyler and Rick discuss the challenges faced by Leg Up Health during open enrollment, including issues with email communication and the impact of AI on consumer behavior. They...

In this episode, we talk about whether Rick’s expertise with traditional inbound marketing will work for LegUp Health. ...

Monday 22 September 2025...

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 strategie...

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

In this episode, we talk about some metrics that are headed in the right direction. Let’s go ...

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

In this episode, we recap 2024 and set goals for 2025:Personal goals for 2025:Rick: Primary theme: Buy back timeTake 1 personal day every 1-2 monthsGet time back for things I love (skiing, ba...

In this episode, we discuss how there are multiple different approaches to take when a startup needs to grow the team. ...

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

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

We’re both in marketing mode right now. In this episode, we dive into the specifics of what we’re trying. ...

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

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 actu...

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

In this episode, we talk about about the impact a recent price change is having on Less Annoying CRM’s finances.  ...

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 th...

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?  ...

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. ...

 In this episode, we talk about Less Annoying CRM’s new form builder, and what it means for the business  ...

In this episode, we discuss using consultants to level up your team. ...

 In this episode, Rick explains how he’s getting more hands on with marketing.  ...

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? ...

 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. ...

 In this episode, we talk about Less Annoying CRM’s latest sales experiment.  ...

In this episode, we talk about takeaways from big snow tiny conf, and more. ...

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

This 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 updatesFoun...

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

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

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 abou...

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 rem...

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 i...

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 ...

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 worki...

 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 de...

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 i...

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 thing...

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...

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 appr...

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 sabbaticalLACRM is getting ready to launch a ma...

Come on, you know what we're talking about. It's all anyone is talking about. Sorry, we don't make the rules. ...

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 t...

 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 dis...

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...

 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 ConfT...

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 useful...

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 ShellyRickGo...

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 ex...

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 thi...