Business advice

Here's a collection of all my posts about running a small business:

The thing about requiring credit cards to sign up for a free trial
A common question in SaaS is whether or not to require credit cards up front. I think the decision is easier than people make it seem.
Founder compensation - How to decide what to pay yourself
A tricky topic that every founder hopes to face is how much to pay themselves as the company grows. There are so many complicating variables.
Innovation Tokens - When to break from the status quo
Innovation is often talked about as an entirely positive thing, but it comes with a significant cost. This post explores when it makes sense to innovate, and when it doesn't.
Why we aren't a remote company
More and more companies are going remote, and that's great! But Less Annoying CRM has decided to stay in-person-first. This post explains why.
Lower growth means lower churn
In retrospect it's obvious, but maybe you've never thought about this: If your growth rate slows down, your churn will improve. Here's why.
How I ask questions in 1:1s that get honest answers
Asking good questions in a 1-on-1 meeting with employees is an art form. The right questions will uncover valuable insights about your business.
The trough of meeting overload
As you hire more people, you'll likely find yourself in more meetings. But there's a light at the end of the tunnel...
The trap of hiring early employees to be future leaders
It's common for first-time founders to want their early hires to run their respective departments as the company grows, but it's normally not that simple.
Bootstrapping a software business built on WordPress with Lesley Sim
This discussion with Lesley covers a variety of topics related to the tactical issues she's working on at her bootstrapped startup.
Should you sell a product before building it?
Conventional wisdom says to validate a business idea by pre-selling the product to customers. I'm not so sure.
The problem with thought leaders
People who make money producing content often aren’t the experts they pretend to be.
The cat’s on the roof
As a leader, communicating change is an essential skill. Here's how I do it.
Freemium pricing, and cannibalizing your existing customer base
Switching to a freemium model can threaten existing revenue streams for an established business. Here are some ideas for dealing with that.
Can freemium products have good customer service?
Freemium can be a great marketing strategy, but how can you afford to provide good support when 95% of your users aren't paying?
What does “freemium” mean?
Freemium is an increasingly popular marketing strategy for online businesses. Unlike a free trial which ends after a set amount of time, freemium has an indefinite free period.
The best process is to not have one
A question I get often from new founders is about process. People who worked at large companies are used to having a process for everything and they want to emulate that.
Should remote employees be paid based on location?
There's a lot of debate about whether remote employee compensation should depend on cost of living. Let's explore...
The thriving wage: Compensating employees fairly
Have you ever heard of a customer service rep making $125,000 per year? At Less Annoying CRM, that's the going rate for someone with experience. In this post, I'm going to explain why.
The one skill every entrepreneur needs
No matter what your business does, you'll have to be comfortable working with a blank slate.
The problem with being data-driven
It's tempting to let data drive every decision you make at a startup, but there are many questions that data can't answer.
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