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Hi, I'm Bobby Matson.

I'm a NYC-based software engineer and entrepreneur. I love working on new business models and experimenting with funky ideas. Shoot me an email if you'd like to collaborate on one!

Bobby's Blog

Mandatory Timeoff

This is the first week of Mandatory Timeoff. It’s technically a two month sabbatical, but with a different flavor. I plan to give myself time to reflect and reset, but with the added bonus of “working for myself” throughout the process.

For years, I’ve been working as a software consultant with the fine folks at Carbon Five on dozens of fun projects. After awhile, you start to get pretty seasoned at jumping into the deep end of a new problem space and ramping up quickly. Each time I do this, I wonder what it would be like to do it for myself.

What if I dedicated the same amount of time (~3 months, 40 hours a week, 8 hours a day) working on my own project? What would I work on?

Funny comic

To answer this, I started looking back at my side projects over the years. As a full-time employee, side projects are hard because we have to sacrifice personal time to scratch our creative itches. They are nourishing, but can be quite draining if you’re not used to moonlighting.

Historically, I’ve been pretty bad at personal side projects. I have ideas - some good, most bad - that I work on solo for three weeks and then lose interest on. I have countless examples of projects that have been partially worked on and shelved.

Starting now until September 1, I’m dusting off one of these side projects and documenting the results here.

When deciding on the problem space, I found something that I could execute on quickly, had the right market timing to do well, and could actually be grown into a revenue-generating business. It had to be born from personal experience. On top of that, I needed to have a unique insight into how to solve the problem in a new way.

My choice? Payoff, a solution to the myriad of looming student loan debt problems which plague most Americans. Over the next few weeks, I’m putting on my Product Hat and conducting surveys, user interviews, hypothesis invalidation and prototyping before writing actual code. I’ve done the startup thing before, but this time it’ll be 100x better, with 100% new mistakes and wins.


If you’re interested in hearing more about this, hmu.