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. LACRM had a great month in February. There was absolutely nothing to learn from it. LACRM's major redesign is getting closer. Rick has...

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 Utah next weekend. Tyler is having success with delegation, and finds himself with a lot of unstructured time on his hands... ...and Tyler is...

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

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

This is our yearly recap episode!

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

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.

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

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 each year, called open enrollment. In this episode, we talk about what he’s doing to prepare for this huge opportunity.

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 to avoid that trap.

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

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.

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

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.

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

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.

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

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.

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.

In this episode, we discuss how to connect employees with mentors when there's not already someone at the company with expertise.

This week, we talk about how to define the purpose and constraints of a business.

This episode, we've got a grab bag of different topics including a product-led growth discussion, what to do with a stagnent content site, and the role tools should play in running a business.

This week, Rick helps Tyler think through a new growth plan for Less Annoying CRM

This week, we talk about how both patience and impatience are important when hiring, how to learn new things, and more.