How Brian operated up to 6 businesses simultaneously

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SaaS entrepreneur Brian Casel knows a thing or 2 about juggling projects.

Between 2012 and 2021, he was running anywhere from 2 to 6 businesses simultaneously. In 2021, Casel sold 5 businesses in a 6-month period. In total, he’s launched 14 different products.

Some companies were his main focus for years, while others were smaller side projects. The exits ranged from 4-figures up to the high 6 figures like his sale of Audience Ops.

He sold his portfolio of companies to focus fully on ZipMessage, a tool for sending asynchronous video messages, and his podcasts Bootstrapped Web and Open Threads.

I spoke with Casel about what he’s learned, how he juggles projects, and his advice for founders hoping to do the same.

What was your work before indie hacking?

I started as a front-end web developer and designer at a small agency in NYC. In 2008 I went freelance as a web designer/developer.

How’d you get started?

The first digital product I created and sold were WordPress themes, which I started selling in 2009. Then in 2012, I started my first SaaS business (a website builder for Restaurants), which I sold in 2015.

Over the next 6 years, I started, grew, and sold multiple other businesses including productized services, a course/community business, and small SaaS products.

How many companies have you operated simultaneously?

Between 2012 and 2021, I was running anywhere from 2 to 6 businesses simultaneously, but only focusing on 1 at a time, while the others were just coasting in my portfolio.

How did you balance the work?

When I was running multiple businesses, for the most part, I focused on only one at a time while attending to occasional support tickets on the others. Each “sprint” might last anywhere from 1 month to 6-12 months focused on a single business while the others coasted.

Now I’m focused on one SaaS — ZipMessage— and it still feels like juggling many different projects at once, except all within the same business. Product design, dev, marketing, hiring, etc.

What challenges have you had when running multiple businesses at once?

Personally, I have no regrets about building a portfolio of businesses in the early part of my career. I benefited from this in several ways:

• I learned a ton, across a wide range of skill sets and business types
• I became exposed to the pros/cons of different businesses and markets in a short period of time
• I’ve always built in public and podcasted throughout this time. Starting, building and then selling businesses gave me a lot of “material” to talk about on air and a reason for others to invite me to interviews.
• Every business was a stepping stone to the next one. Every business was a reaction to the previous one. I wouldn’t have landed on ZipMessage today had I not had the experiences that came before it.

What are some pitfalls?

Don’t follow a path just because someone else told you “it’s the way.” See what inspires you and learn what works for you as you go.

What advice do you have for founders that hope to operate multiple businesses?

Start with something relatively small and move on to bigger products from there.

Also, early on, the most valuable product/business ideas are the ones where you’ll learn and gain skills and experience you didn’t have before. Sure, you want to look for opportunities to find customers, but building your toolbelt and surface area is even more valuable — this is what leads to ideas you didn’t know existed!

What core skills did you cultivate to become a well-rounded entrepreneur?

In my case, having done so many different “types” of businesses, I became exposed to a pretty wide set of skills.

First, being a professional web designer and working on globally recognized brand websites gave me a really strong foundation in design and shipping quality websites for anything I ever need to promote.

Then I spent many years deep in productized services—where I became really strong with hiring teams and building systems and processes to run repeatedly at scale.