Barring a fair market salary I would argue an even split is appropriate. If this is a tech company, the other party doesn't need you for a series A, they need you to run the company... which at this inflection point is fundraising.
Just spitballing here:
In exchange I would be generous on the vesting side of the equation. I'd ask for half the company over 6 years where you get ~75% of your shares in the first 2 years of the relationship. The company will probably be dead by that time anyway (based on how these things go). If not, you've earned your keep.
You'd definitely be wise to consult an attorney about how to execute whatever deal you agree to do. They'd probably be able to give you better advice.
Great write up on the psychology of starting. I think this feeling is easy to conceptualize, but hard to truly understand unless you're an actual founder. Most people want you to be successful even if they don't show it though.
I would say that most of the "loopholes" that you're referring to aren't really accessible to the average Joe because most of us make what's considered "Earned Income". That's what your salary is considered and it's taxed according to your tax bracket. Wealthy people will structure their income and their holdings in ways to minimize the amount classified in the earned income bucket. The extreme is when executives take $1 salary.
The AI is going to be superior in terms of explaining which factors played in your return. This will become clearer how powerful it is when the application suggests ways to optimize your situation and you basically have a playbook in hand to use.
I've done this when I was working on the Playstation Network so business users could define storefront categories that contain products based on their own custom logic. We didn't get a lot of requests to change the feature and it was stupid simple. I wouldn't get too fancy unless your users get really excited about it and ask for it to do more.
Your odds of being audited are based on the information that you provide, and that alone. Your return will be rejected if the government tests it and it fails to have the correct calculations. This happens. The government gives companies 48 hours to correct and retransmit in those cases (by law). All sorts of games are played using this 48 hours window. And it would be improper for me to discuss this with you further beyond just stating the law is on the books and it is utilized. Obviously we'd prefer to submit your return and be correct 100% of the time.
Everything you said is true. There's a pretty big difference between 4 people versus 400 people working on software. All I can say is that probably 10% (that's optimistic) of the people working on any given project make a difference in a large company. At least that's been my experience. And that's why you get startups bringing products to market with great success over and over again.
We encourage you to keep spending the money if it gives you the warm feelz! It's your money and it's our job to convince you to make the switch. You'll be able to use any product out there and compare the results for yourself before submitting your returns next season, so we've got that going for us.
At the moment it's a Java stack, but we're intentionally not limiting our search to Java developers because we don't mind learning new ways of doing things - we love that part of software development.
That said, web is pretty broad so if you're a database expert that also dabbles in sys admin and node then we're interested in talking with you. If you're a talented engineer you can adapt to new technologies is the way we see it.
Tax pros are like developers, most comfortable closer to the bare metal if you will. They use a separate product line that mimics the actual forms closely. They don't like the interview style because it just slows them down when they're barreling through hundreds of returns. Beyond the UI, there's no difference in the calculations they work with so that should tell you something.
Just spitballing here: In exchange I would be generous on the vesting side of the equation. I'd ask for half the company over 6 years where you get ~75% of your shares in the first 2 years of the relationship. The company will probably be dead by that time anyway (based on how these things go). If not, you've earned your keep.
You'd definitely be wise to consult an attorney about how to execute whatever deal you agree to do. They'd probably be able to give you better advice.