H1b transfer for new small corp c startup

How easy/doable/possible it is for an early small (two man) funded start-up to hire someone how is now working with H1B for another company and we apply for a H1B transfer for him to come join us?

Totally doable - I was hired by funded 2 person company while I was on H-1b. According to my lawyer, the company must have an office and substantial amount of money in the bank account. You should definitely hire a good attorney for this process. It will probably cost you ~$5K for the whole process.

Yes. Should not be a problem. I was hired as a first employee of the company who has a single owner and home office. The process was smooth although I did go for premium processing. As long as you have enough funding or prove that you can pay him the salary, you should be good. Hiring a lawyer is really worth the cost. But please be careful about your documentation if you are just a placement agency. Things are getting harder for such type of applications due to recent gov crackdown and also the law changes. For simplicity purpose , if you don't control your employee on his daily operations you application is at risk. All the best.

Technically it is possible. Easy? Doable? That's a different question. You should talk to an experienced immigration attorney (yes, it may cost several thousand dollars just in the attorney fees). I would suggest that it would not be easy at all, if doable.

Generally, there's no such thing as "H1B transfer". The only difference between the original H1B application and the "transfer" application is that the transfer is not subjected to the quota. The burdens of proof, the requirements, the fees - all are the same.