I mean, it was definitely a shock and I wasn't necessarily thrilled about the whole deal. But, again, what was I going to do? Say "No thanks" and walk out the door unemployed? The only thing I might would have done differently was say "Yeah, sounds good" and then immediately start looking for another job. But I didn't, and it worked the way it did. All things considered, it wasn't so bad.
One of the biggest mistakes was trying to change technology without changing culture. Sure, we had buy-in from the CEO and board but they don't actually run the company. You can't force-feed cloud into a culture that doesn't understand/appreciate it. You can't take calculated risks in an organization whose whole purpose is to avoid/outsource risks.
Beyond the obvious 3 (toxic people, false promises, value system misalignment), here are 3 signals that made me leave quickly (stack ranked):
#1 Your boss doesn't inspire you _every day_: I don't mean this metaphorically. In the first year, almost every day you must be like "holy molly, I am so lucky to be working with this person. I'm gonna learn so much from him/her/them."
#2: You are the smartest person in your team: I always tell people: "if you are on top of mountain then you are probably on a bunny hill. Go find a real mountain." You need people who pull you up, while you grow them in other ways. So there must be something about the people around you where you are like "I wish I had that. I must learn how he/she/they do this."
#3: Company focusing on the wrong things: Too much tactics, too much strategy, too much product, too much engineering. Most of these symptoms manifest themselves as products/features that don't align with where you think the world is headed.
Now for what I would have done differently:
For #1 and #2: I must say that I have been so fortunate to work with some really really inspiring reports, peers and supervisors. In the one odd case where it didn't pan out that way, I wish I had spent a little bit more time with the person I was gonna work and the team I was gonna work with, before I accepted the offer.
For #3: This one is easy. You can literally spend half a day reading up on the company, their products, and the general domain to figure out whether this one is worth your time or not. What's wrong internally that makes them ship the wrong things isn't important for your decision any way.
None of the above signals are a disaster in big companies as you can always look for a different team which checks these marks. But if you are going to a startup or an early stage company then it's better to rip the chord quickly.
A minor quibble (in a very good comment) from experience re #3: if you’re considering a more mature company, you can be biased favorably by long-standing reputation while not being able to see that, internally, the end of the road is coming up quickly.
I didn't realize how messed up internal systems were during the interviews or what group dynamics actually were in real life. I judged too much from the hiring manager and the best of my colleagues whom I still think highly of. I thought I could make a difference and they paid really well (not FAANG).
What changed was a combination of realizing how little I could actually do, magnified by a whole new tier of VPs hired from Microsoft and Google who brought their loathsome ways with them. One never expects the Spanish Inquisition...
It's impossible (IMHO) to avoid things like that. In this situation, I couldn't predict the future - hiring a new "leadership" (gack!) that transmogrified the organization I joined.
Biz tax is a deep topic. Short answer is the LLCs are passthrough, which means you'll receive a k-1 from your accountant that you include in your personal return.
Quick strategy tip: have your accountant apply for S corp status for your LLC. You'll pay less tax right away.
Note in CA, there are additional reporting requirements. This is not tax advice, but I believe passthrough single-member LLCs (including no-income) must file Form 568 by March 15 and pay a mandatory $800 annual fee by April 15. (Other types/taxation methods could have slightly different requirements.)
I'm assuming you are US-based. If you receive compensation in stock, no matter the currency denominator, it is income and is therefore subject to income tax.
Your employer should produce a W-2, and your share grant will be included.
