My name is Brian and I live a double life

Hi all,

I just wanted to introduce myself. I have been a longtime listener of the Bootstrapped podcast and have spent a good deal of time on this forum, but have finally decided it was time to sign up. I’m in a bit of a unique situation (well, maybe not so unique) in that I have been living a “double life” as a developer/bootstrapper and as an estate tax attorney for an extended period of time.

I work full-time during the week as an estate planning attorney in Los Angeles. I specialize in ultra-high net worth individuals and families. In this realm, my job includes handling core estate planning (multiple types of trusts, wills, etc.), structuring ownership of businesses and real estate, and wealth transfer. I focus most of my time on complex tax planning and spend a good chunk of my day in the Internal Revenue Code.

I also happen to be a developer and bootstrapper. I started programming about 15+ years ago and have been involved with various aspects of bootstrapped businesses ever since. Much of my time has been spent building the back-end systems that run an online advertising/social media company. A couple years ago, I launched, along with a friend, a company called Unbucket (, which is a platform for creating and sharing lists of things to do/experience with others. We predated most of our competitors and got really great traction. We built up a full-featured business with virtually no money and by doing everything in-house between the two of us (except our logo). Unfortunately, Unbucket is in its final stages, but I’m already working on some new ideas.

Finally, some years ago I created LadinoType (, which is a transliteration engine for the Ladino language. Ladino is a dying language that is a really interesting mix of several other languages. It was traditionally written in special scripts that I brought to the internet for the first time. The front-end of the site is stuck in early 2000’s when I was not very skillful and the technology was limited, but I’m completely re-writing it into essentially a version 5.0. The back-end is actually pretty cool and does some things I haven’t seen before with foreign languages.

Anyway, my two worlds actually complement each other very well and each gives me a lot of insight and skill into the other. For now, I’m going to keep up the dual life…until one side eclipses the other. For now, though, I hope to share some of the insight I’ve gained along the way with you all here.




Welcome! I’m glad to hear this. There’s a tendency to think you have to go “all in” on your bootstrapped software or you’re not really doing it. Clearly, you’ve got a balance that makes you happy and supports you.

Most of us could use some solid estate planning advice, too. Do you have any resources to recommend? Estate Planning 101?

Also, there are probably some lessons in Unbucket, if you’re comfortable sharing. You said it’s (unfortunately) in its final stages. Care to elaborate?

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Sounds really interesting. It’s nice to hear that someone are able to pull such a life of! Wish I could myself. But like Coreysnipes pointed out, it could be cool to hear some of your lessions from unbucket? :slight_smile: