I've been a programmer for over ten years, across small startups and big companies. Some had terrible benefits (no equity, no 401k match, or a match with a punishing vesting schedule); some had great ones. I've come to realize that when maximized, these benefits can dramatically increase the rate of wealth building. Over the years, I've also stepped on most of the landmines along the way, and by now I'd say I understand how these programs work. Even so, the ongoing maintenance takes effort, especially when you change jobs, or when your employer switches 401k administrators mid-year without you changing anything. Those are the moments when you have to recompute a lot to make sure you're maximizing every benefit without over-contributing, otherwise you risk a tax penalty that often times cannot be undone.
There are plenty of calculators, and there's ChatGPT/Claude/Gemini, but they all share the same problems:
- They're one-shot. Every time you need to recheck, you start over: re-enter the data, restart the chat.
- They require you to remember to check ahead of time. If you're busy or just forget, some benefits are simply gone for the year, or the penalty is already locked in by the time you notice.
- Every employer's terms are different: the 401k match policy, how much the HSA employer contribution is and at what cadence that's distributed, whether after-tax 401k contributions are allowed. You have to dig up the details yourself.
- You don't know what you don't know. If you've never heard of a benefit, you're not going to try to maximize it. I was at my first employer with a mega backdoor Roth for most of a year before I learned it existed. It took several more years to learn that the regular backdoor Roth is a different thing entirely.
I'd previously released a free, anonymous diagnostic (still there, still being maintained). This is the MVP of the paid version. What it does today:
- Monitors 401k (pre-tax, Roth, and after-tax for the mega backdoor Roth) and HSA contributions paycheck by paycheck against the current year's IRS limits. When something needs to change, it tells you exactly what: the new per-paycheck amount, which paycheck to change it on, and the date you'll land on the limit.
- Job changes: the calendar shows both employers' paycheck schedules. The per-person deferral limit follows you; the combined plan limit is per plan. Both are tracked with accuracy.
- Plan terms for 41 employers are on file, compiled from public sources such as the companies' filings. Not every clause of every plan is covered yet. I'm ready to prioritize based on user requests.
I've been using it myself along with a few friends for a while now and ready to open it up further.
Now looking for founding members: $240/year (or $25/month). The annual price is locked for as long as you stay a member, and annual plans have a 90-day full refund. Email me directly with questions; I reply within a day, and I'm happy to jump on a call if that's useful. This is an early MVP: there's plenty that isn't polished yet, and there are bugs. Bug reports and feature requests from founding members get handled first.
You don't need to be an expert on any of these benefit terms. Some familiarity and an interest in getting the most out of your benefits is sufficient.
My longer-term goal is a full workplace and retirement benefits platform: ESPP, backdoor Roth IRA, FSA, RSUs, stock options, and major life events like marriage or a new child. Later, an explanation of your 401k fund lineup and personalized recommendations (need some compliance work done first). And one key underlying assumption of the current product is that you can afford to, and want to, max everything out. That's obviously not true for everyone. A friend told me, "I can't max these out, daycare eats most of my paycheck." That's common, and personalization for it is on the roadmap.
I've been a programmer for over ten years, across small startups and big companies. Some had terrible benefits (no equity, no 401k match, or a match with a punishing vesting schedule); some had great ones. I've come to realize that when maximized, these benefits can dramatically increase the rate of wealth building. Over the years, I've also stepped on most of the landmines along the way, and by now I'd say I understand how these programs work. Even so, the ongoing maintenance takes effort, especially when you change jobs, or when your employer switches 401k administrators mid-year without you changing anything. Those are the moments when you have to recompute a lot to make sure you're maximizing every benefit without over-contributing, otherwise you risk a tax penalty that often times cannot be undone.
There are plenty of calculators, and there's ChatGPT/Claude/Gemini, but they all share the same problems:
- They're one-shot. Every time you need to recheck, you start over: re-enter the data, restart the chat. - They require you to remember to check ahead of time. If you're busy or just forget, some benefits are simply gone for the year, or the penalty is already locked in by the time you notice. - Every employer's terms are different: the 401k match policy, how much the HSA employer contribution is and at what cadence that's distributed, whether after-tax 401k contributions are allowed. You have to dig up the details yourself. - You don't know what you don't know. If you've never heard of a benefit, you're not going to try to maximize it. I was at my first employer with a mega backdoor Roth for most of a year before I learned it existed. It took several more years to learn that the regular backdoor Roth is a different thing entirely.
So I built a benefits assistant: https://www.cedarwise.ai/?utm_source=hn
I'd previously released a free, anonymous diagnostic (still there, still being maintained). This is the MVP of the paid version. What it does today:
- Monitors 401k (pre-tax, Roth, and after-tax for the mega backdoor Roth) and HSA contributions paycheck by paycheck against the current year's IRS limits. When something needs to change, it tells you exactly what: the new per-paycheck amount, which paycheck to change it on, and the date you'll land on the limit. - Job changes: the calendar shows both employers' paycheck schedules. The per-person deferral limit follows you; the combined plan limit is per plan. Both are tracked with accuracy. - Plan terms for 41 employers are on file, compiled from public sources such as the companies' filings. Not every clause of every plan is covered yet. I'm ready to prioritize based on user requests.
I've been using it myself along with a few friends for a while now and ready to open it up further.
Now looking for founding members: $240/year (or $25/month). The annual price is locked for as long as you stay a member, and annual plans have a 90-day full refund. Email me directly with questions; I reply within a day, and I'm happy to jump on a call if that's useful. This is an early MVP: there's plenty that isn't polished yet, and there are bugs. Bug reports and feature requests from founding members get handled first.
You don't need to be an expert on any of these benefit terms. Some familiarity and an interest in getting the most out of your benefits is sufficient.
My longer-term goal is a full workplace and retirement benefits platform: ESPP, backdoor Roth IRA, FSA, RSUs, stock options, and major life events like marriage or a new child. Later, an explanation of your 401k fund lineup and personalized recommendations (need some compliance work done first). And one key underlying assumption of the current product is that you can afford to, and want to, max everything out. That's obviously not true for everyone. A friend told me, "I can't max these out, daycare eats most of my paycheck." That's common, and personalization for it is on the roadmap.