1 - Why shouldn’t two companies merge?
Because one is private and the other is public, so the i-bank will make more fees by IPO ing the private one and THEN advising on a takeover: double whammy.
Alternatively, because both companies use your i-bank as an M&A advisor, so if they merge, you'll only be able to avise one party creating work ang giving league table credit to another ibank, letalone the fact that as far as management at your i-bank is concerned, you have swapped short term M&A fees for all the future cash the bank would have gotten from one of the companies.
2 - Give me an ideal Debt / Equity ratio...
This is a bit of a chicken and egg situation,a nd it all depends on what the client wants to hear. Example: If client believes they have too much debt, you advise them to issue more equity (and make sure that they issue too much equity in an offering / private placement / etc). Before any other bank has a chance to pitch to them, you go and pitch releveraging the balance sheet on the back of all the equity they have. Once they do this, you pitch a mega acquisition to use all the cash they have lying about and doing nothing with. Once deal is done, and markets turn bearish, you come in to restructure the acquisition, spin off the company you advised them to acquire, restructure the debt you raised for them and virtually take them to square one. Square one, well, square one, plus loads of equity + debt + M&A + restructuring fees for the bank.
3 - Can you calculate comps with negative EBITDA?
Yes. A / B = C. If B is negative, so will C. Can you calculate it? Sure. Does it mean anything? Of course not. The bigger question here is whather calculating Enterprise Value / EBITDA or any other bullshit metric means anything. At the end of the day, why does it matter if you're advising a client on buying a company that all the comparable companies trade at 6.0x EV / EBITDA when you know there's some crazy private equity cowboy out there who's going to pay 7.0x? What do you do? Do you really foresake the fees and say they shouldn't pay 7.1x and win the deal and fees for you? Of course not. You madssage the numbers, add synnergies to the EBITDA, make deductions from the EV, do whatever you need to to make it look like you are paying 5.9x when you're really paying 7.1x and them tell the client they are gettign a great deal. You get your fees. Cleint management gets a big bonus from for securing a good price from sharesholders. Everyone wins, ahem, apart from shareholders, but why do they count?
4 - If you sell a PPE for 100, BV of 50 and you had a note payable of 50, how do you make entries into the balance sheet?
This is an irrelevant question. If you masagged your numbers well enough to get the client to pay 7.1x (see 3) whilst making it look like they are paying 5.9x, nobody will care what your balance sheet looks like. So, hard plug whatever you want, make sure your multiple shows 5.9x and go for a beer.