All Episodes

Displaying episodes 1 - 30 of 148 in total

The pricing change I didn’t want to make

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 me...


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 progre...

Execution eats strategy for breakfast

 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...

Getting unstuck

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 o...

You can't optimize nothing

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...

Handling sales tax as a SaaS

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 partner...

Recapping the Product Hunt launch

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...

Pivots and renegotiations

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 gett...

Yet another podcast about AI

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

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 ...

How to win against well-funded competitors

 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 compensa...

The one where we negotiate Tyler’s compensation

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 compens...

How we deal with security questionnaires

In this episode, we discuss what we do when a customer has security and compliance questions, plus, a whole lot more.

Something new to announce

This week, we share some exciting news that impacts both of us.

Looking back at 2022 and forward to 2023

This is our yearly recap episode!

Big bets vs small bets

In this episode, we talk about prioritizing big revolutionary ideas vs small iterative improvements, and a whole lot more

How can founders use the new AI tech?

This week we talk about the recent boom in AI, and whether or not founders like us can take advantage of this new wave of innovation.

Professional hater

This week we talk about Twitter melting down, tech layoffs, and other generally unpleasant things that mostly haven’t effected us so far

An opportunity that comes along once per year

Most bootstrapped businesses are all about slow, steady, consistent growth. Rick’s business is different because he gets almost all his customers during one period eac...

What's priority #1?

In this episode, we talk about how easy it is to work on multiple things at once because it lets you avoid making tough prioritization decisions, and what we’re doing ...

The marketing tech stack

This episode, we talk about whether or not it makes sense to build home-made tools to help with marketing

How much to spend acquiring a customer

In this episode, we talk about CAC, customer acquisition costs, and how a startup can decide how much is too much to spend on acquisition.

The great re-org

In this episode, we talk about how we’re thinking about reallocating marketing and sales resources here at Less Annoying CRM.

Is SaaS getting harder?

Sometimes it feels like the tech industry is more of a zero-sum game than it used to be. We discuss that, and a lot more in this episode.

Single points of failure

Are single-points of failure sometimes ok? In this episode, we talk about how much redundancy a small company should have.

Should you hire a marketing agency?

In this episode, we talk about whether or not it makes sense for an early stage bootstrapped company to hire a marketing agency for help.

Healthy urgency

In this episode, we talk about healthy vs. unhealthy urgency, and whether it's realistic to hire a team of entirely high-urgency people

Prioritizing effectiveness over efficiency

In this episode, we've got a grab-bag of topics including when to worry about scaling, an argument against delegation, and a few shoutouts.

Charge Less

In this episode, we talk about how conventional wisdom around pricing is sometimes wrong.


In this episode, we discuss how the recent economic uncertainty might impact bootstrapped businesses.

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