James Bohan CFO

James Bohan CFO A CFO with both institutional and entrepreneurial experience.

At Stonehan we focus on providing white-glove tax, CPA, & financial services for sophisticated real estate investors, family offices, and private equity fund managers. Providing elite financial services for the real estate industry with a contrarian takes on taxes, finances and investing.

06/15/2026

AI is useful in tax work. I use it myself.

The issue is when people start replacing the review and judgment layer with it entirely.

AI can process information quickly. That doesn’t mean it understands whether:

• allocations reflect the economics
• the structure actually works
• or the reporting matches what’s happening operationally inside the fund.

That’s still where experience matters.

The risk usually isn’t speed. It’s removing the layer that’s supposed to catch what’s wrong before the filing happens.

Where do you think AI actually helps in fund operations versus where it creates more risk?

I didn’t wait until senior manager to leave.I went from staff accountant to CFO because I saw a bigger opportunity and t...
06/13/2026

I didn’t wait until senior manager to leave.

I went from staff accountant to CFO because I saw a bigger opportunity and took it.

Looking back, it probably didn’t make complete sense on paper at the time either, but a lot of career moves don’t.

I think a lot of people stay in situations too long because they’re waiting for the “right” timing, title, or next step to appear first.

Usually it doesn’t work that cleanly.

At what point do you think someone knows it’s time to make a move professionally?

06/11/2026

One of the reasons I focus so heavily on private equity real estate fund managers is because I’ve sat on both sides of the table.

I was the CFO of a fund for four years. I’ve also invested in real estate personally, and now I advise fund managers and syndicators full time.

That combination gives me a very different perspective than someone who only understands the tax side or only understands operations.

A lot of tax decisions inside funds affect:

• investor relations
• reporting
• distributions
• acquisitions
• and long-term planning.

That’s why understanding the actual business matters just as much as understanding the return itself.

What’s been the hardest operational issue inside your fund recently?

One thing I’ve learned working with fund structures is that small entity decisions early on can create very large conseq...
06/11/2026

One thing I’ve learned working with fund structures is that small entity decisions early on can create very large consequences later once the structure starts scaling.

Sometimes the issue is obvious immediately. Sometimes it takes years before anyone notices the downstream impact.

That’s why I think a lot of people underestimate how important structure review actually is on the front end.

Especially once:
• more investors get added
• more entities exist
• reporting becomes more complex
• or the management company starts growing separately from the fund itself.

Most of the expensive issues I see usually start as something that originally looked minor.

What’s the biggest structure issue you’ve seen surface later after a deal or fund scaled?

06/10/2026

There’s a lot of tax advice online right now that sounds good until you actually apply it to a real structure.

That’s especially true in real estate.

A strategy can technically exist while still being completely wrong for:

• the entity setup
• the investor structure
• the GP / LP arrangement
• or the operational reality behind the deal.

That’s usually where people get into trouble.

The issue normally isn’t that the strategy itself is fake. It’s that someone saw a 30-second clip online and tried applying it without understanding the downstream consequences.

What’s the worst real estate tax advice you’ve seen floating around recently?

Most investors think REP status is just about getting over 750 hours.That’s usually not the part that causes problems.Th...
06/08/2026

Most investors think REP status is just about getting over 750 hours.

That’s usually not the part that causes problems.

The bigger issue is:
• documentation
• material participation
• and whether the investor is actually involved enough operationally.

I’ve seen people hit the hour requirement and still have problems because the activity tracking was weak or too much of the work was delegated out.

As portfolios grow, this gets more common.

Property managers take over more.
Teams grow.
Operations become less hands-on.

A lot of investors don’t realize their qualification changed until much later.

That’s why this should be reviewed during the year instead of trying to recreate everything during tax season.

What part of REP status do you think gets misunderstood most often?

06/06/2026

A lot of investors default to a 1031 automatically after a sale.

Sometimes it makes sense. Sometimes it doesn’t.

What I see happen pretty often is the timeline starts controlling the acquisition process. Once the 45-day window starts, people stop asking whether the acquisition is actually a good deal and start asking whether they can close in time.

That’s usually where mistakes happen.

I’ve seen investors force replacement deals they weren’t really confident in just because they didn’t want to trigger taxes.

In some situations, using depreciation differently on the next acquisition creates a cleaner outcome anyway without forcing the exchange timeline.

Most of these decisions should really get evaluated before the property ever goes to market.

How are people approaching 1031s right now with deal flow where it is?

A lot of managers don’t start thinking seriously about exit tax planning until the property is already getting ready to ...
06/04/2026

A lot of managers don’t start thinking seriously about exit tax planning until the property is already getting ready to sell.

Usually by then, most of the important structure decisions have already been made.

That includes:
• entity setup
• allocation mechanics
• depreciation history
• investor economics
• and how distributions flow through the structure.

I think people underestimate how much of the final tax outcome is already shaped years before the sale actually happens.

The issues usually don’t show up during the hold period either.

They show up later:
• during exits
• investor reporting
• distributions
• or after closing when everyone starts reviewing the economics more closely.

That’s why the best exit planning conversations usually happen long before the property goes to market.

At what point do you think most managers actually start evaluating the exit strategy?

06/04/2026

A lot of investors spend more time negotiating small operational expenses than they do thinking about long-term tax strategy.

Meanwhile taxes end up being one of the largest expenses attached to the investment over time.

That’s usually the disconnect I see.

People focus heavily on acquisition, financing, and operations, but the tax side often becomes reactive instead of intentional.

The investors who usually keep more of the upside long term are the ones thinking about structure and planning before the transaction is already moving.

Where do you think most investors wait too long to start planning?

I’ve seen investors back themselves into deals they didn’t even really want because the 1031 timeline started controllin...
06/03/2026

I’ve seen investors back themselves into deals they didn’t even really want because the 1031 timeline started controlling the decision making.

Once the sale closes, the pressure ramps up fast:

• 45 days to identify
• 180 days to close
• and suddenly the priority becomes completing the exchange instead of finding the right deal.

Sometimes that still makes sense.

But I’ve also seen situations where using depreciation from the next acquisition created a much cleaner outcome without forcing the investor into a rushed timeline.

The biggest issue is most people don’t look at these options until after the process already started.

By then, most of the flexibility is gone. The best tax planning usually happens before the property even hits the market.

Have you seen investors force acquisitions just to complete a 1031?

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