Keeper Tax Community Spotlight: Addison Freeman

Paul Koullick
September 21, 2022
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The Keeper Community Spotlight series highlights awesome freelancers using our business expense tracker, their stories, and advice to others.


Addison, thanks for being here! So, how did you get into freelancing?

Thanks for having me! To begin, I spent years as a full-time employee first in IT Consulting and then at a web development firm. I hated the bureaucratic aspect of a traditional 9-to-5, but I always loved to build and to create. Freelancing has given me the space to do it on my own terms, as a part of a lifestyle I really enjoy. 

And you’re also part of a traveling band?

Yes! I’m a musician and the cellist in a four-person folk music band, The Riverside. We’ve been traveling across America for the past two years with a pretty rigorous touring schedule, so it has become a huge part of my life. All the while I kept up my freelance programming on the road.

Wow, what a combination. How do you manage both of those?

Community Spotlight:

Well, it can be hectic. I generally do my development work in the mornings, and music gigs in the evenings. Sometimes one of those will spill into the other, though, and I'll have to take a work call from the back of the van, haha. 

How do you find clients?

I started off using online marketplaces for new jobs, but today most of my work comes from repeat clients. It’s so much easier and less of a hassle to work with people you already trust. Then when billing and contracts come into play I’d rather not risk it with more unknowns.


Any advice for others trying to break into freelance web development?

Well, two things: the first is to find a niche. Mine, I’ve fallen into, is doing chrome extensions. I’ve gotten pretty handy with WordPress and anything involving JavaScript too but there are a lot of people building websites. If you can become really good at something unique then you’ll become the go-to professional for that service.

The second is to value your own time. I started off charging far too little and it sent a signal to my customers that my time wasn’t valuable. Since raising my fees, I feel like the work I’ve been doing has also become more interesting and I’ve been treated more like a thought partner along the way.

Let’s talk about taxes. How were you dealing tracking expenses before Keeper Tax?

Yeah, it was hit-and-miss. For a while I was trying to use Quickbooks but it just wasn’t for me. It was just a lot to get acquainted with. I have a very specific need - I just want to keep track of expenses. I don’t have a complicated payroll or inventory like a traditional business. All of the products I used were overkill for my needs, and time-consuming.

I feel like I’m in this middle ground. It’d be good to have a bookkeeper, but it would be expensive and probably overkill. I just remember thinking, “I need something simple.”


How would you describe Keeper?

It does one thing — tracks expenses — and then it gets out of the way. It’s not another app to constantly check in on. It’s an easy interface — text messages — that doesn’t require too much babysitting. It’s like hiring a bookkeeper without all the hassle. They have so many useful tools like their free 1099 tax calculator.


Thanks so much for being part of the community!

Absolutely. I appreciate what you’re doing to make the freelancing lifestyle more enjoyable and manageable. Thanks!

Want to read another community spotlight? Here's Brandons.

Paul Koullick

Paul Koullick


Paul Koullick is the co-founder and CEO of Keeper Tax. His writing on tax topics has been featured on Startup Nation, Freelancer Union, and Tweak Your Business, among other places. Paul has worked in the tax and finance industry for nearly a decade. His previous experience includes building the tax product at Stride Health and Square. Paul holds an A.B. from Harvard University in Applied Math and Computer Science. In his free time, he loves to go jogging and play chess.

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At Keeper Tax, we’re on a mission to help freelancers overcome the complexity of their taxes. That sometimes leads us to generalize tax advice. Please email if you have questions.