All Episodes
Displaying episodes 1 - 30 of 151 in total
Inflection point
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 inflectio...
Reducing Friction
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 m...
Build it and they will come
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 Pad...
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...
Reorg
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