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?

When to outsource

Feb 29th, 2024 49m 8s

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.

Talk to sales

Feb 15th, 2024 39m 33s

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

Learnings from a few days of snowboarding

Feb 1st, 2024 46m 21s

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

Profit first

Jan 18th, 2024 50m 5s

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

Looking back at 2023 and forward to 2024

Dec 29th, 2023 1h 28m

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 updatesFound a band I like: Caligula's HorseFirst time as an adu

DEI isn't dead

Dec 15th, 2023 50m 1s

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

Growth is hard

Dec 1st, 2023 57m 48s

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

Inflection point

Nov 9th, 2023 51m 46s

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

Reducing Friction

Oct 27th, 2023 34m 16s

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

Build it and they will come

Oct 13th, 2023 53m 27s

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 fre

The pricing change I didn’t want to make

Sep 28th, 2023 42m 20s

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.

Reorg

Aug 31st, 2023 42m 37s

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 foc

Execution eats strategy for breakfast

Aug 15th, 2023 48m 53s

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 w

Getting unstuck

Jul 23rd, 2023 54m 28s

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

You can't optimize nothing

Jul 6th, 2023 1h

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 kid

Handling sales tax as a SaaS

Jun 8th, 2023 55m 46s

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/bran

Recapping the Product Hunt launch

May 26th, 2023 1h 4m

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

Pivots and renegotiations

Apr 23rd, 2023 1h 4m

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 major redesignRick gives updates on how the LegUp Healt

Yet another podcast about AI

Apr 3rd, 2023 44m 3s

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

An inside look at building a new product

Mar 23rd, 2023 57m 32s

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 ever

How to win against well-funded competitors

Mar 3rd, 2023 1h 4m

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

The one where we negotiate Tyler’s compensation

Feb 17th, 2023 1h 5m

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