CPA for both IPO tax planning AND real estate investing

[Chris Orlob]

Hey everyone,

I'm yet to hire a CPA and tax advisor to work with, and I'm struggling to find the right person. Here's some context:

I work for a tech company that's going to IPO this year (or early next) and will free up a lot of liquidity for me. So I need someone who's strong in stock options and tax planning for IPOs. Then, I plan on using a large amount of my proceeds from the IPO for real estate investing, so it would seem I'd also need someone strong when it comes to tax strategies and planning related to real estate.

Does this person even exist? It seems like every CPA I stumble across deals with one but not the other.

Should I be working with two different people? If so, where would the buck stop in terms of who actually prepares the taxes come tax season?

Finally, does anyone have any recommendations for a CPA and tax advisor who's strong in both areas?

[Michael Plaks]

@Chris Orlob

It's highly unlikely to find such a dual expert. Each area is a strong specialization, and one person can only be an expert in both areas if (s)he switched specialties. For example, having previously worked for a larger firm where his/her role was related to IPOs and then going on his/her own focusing on REI.

You either work with two people which creates many complications or find a mid-size CPA firm that has specialists in each area but still runs the entire process through the same firm. Both approaches are expensive.