ISO Hero

Since I had my initial idea, several companies have executed it with much more resources and gave it away for free. My version still adds value because it takes into account more complex situations (deductions, long term cap gains, etc), but I don't think anyone would pay for it. I've decided to move on to another project that I believe people will pay for. I'll write up a blog post on what I learned and where it lives, but I probably won't spend much time on it aside from UX improvements.

I work at Intercom, you've probably heard of them. Unfortunately, I've been laid off after my department was moved to Dublin and I did not want to relocate. They've given me ample notice and severance, so I have plenty of time to find a new job. I'm reluctant to find another job immediately, so I will likely take a couple months trying to finally ship ISO Hero in some form and charge a bit for it.

Related to my layoff, my options became a little more complicated and I realized that ISO Hero is missing some features to be usable for myself. I'll be adding those features and solving my own problem soon.

I also found a couple VC backed companies that are building the same tools as I am. On the one hand, I'm a little discouraged since they have built a form of the tools that are free. On the other hand, their tools don't work for my situation and they validated the problem to solve for.

I tried to summarize what I learned about employee stock options from my experience and research. There is a vast amount of reading to do on a complex topic, so I tried to distill some key points in plain English.

I posted on my personal blog, but I intend to clean them up and post them on ISO Hero as educational resources. Conveying complex taxes and financial decisions in an easily understandable way is tough. I learned that people grasp things much easier when you take their personal details and customize the information to their situation. I also learned that putting myself in the story and telling something personal made dry and boring topics much more engaging.

In the past few weeks I came up with a name, bought a domain, and put up a landing page at https://isohero.co. It was my first time writing copy for a landing page and I'm sure I didn't get it right, but at least I shipped it.

I showed my prototype to a few friends and had an informal user test. It is very early and not organized, but I wanted to see if it would stand up to real-world situations other than my own. Of course, there were tons of problems and confusion, but most of it was foreseen. It didn't help that the couple had one of the most complex situations possible: ISO, NSO, and RSUs at two separate companies! In the end, the calculator estimated that they would owe quite a bit of AMT at the end of this year if one of them decided to switch jobs.

Seeing one piece of ISO Hero deliver some insights to my friends was very satisfying. Seeing the existing problems was also valuable and I'm looking forward to making this whole process easy.

I had coffee with a friend who recently left the startup we were working at. He told me about how tax advisers wanted $2k to tell him how exercising his options would affect his taxes. That made me think, "wait, do I have this problem too?"

I spent the next 2 weeks reading up on employee stock options and how they affect taxes, strategies for when or how to exercise them, etc. After many hours of searching, all the material out there is too dense, full of jargon, or incomplete. I pieced together a semblance of understanding and found a single outdated online tool to help me estimate if I will owe AMT after exercising my ISOs.

After working on a better AMT calculator of my own, I thought about how I could help my coworkers who are in a similar situation. But the more I thought about it, the greater the scope became. I could explain how AMT works, but what if they didn't know how taxes worked in general? What was the best way to explain the difference between strike, fair market, and preferred values? How do explain what options are in the first place?

It was clear that employee stock options and taxes are complicated, but it shouldn't take hours of reading to understand. I'm sure some people's situations are complicated enough that paying a financial adviser is worth the money, but I'm willing to bet that most employee stock option holders just need a cheap self-help software alternative.