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.

06/25/2026

A lot of people wait for the “perfect” time before making a move professionally.

Usually that moment never actually comes.

Most career decisions involve uncertainty either way. The difference is whether the long-term upside justifies the risk attached to the move.

I think a lot of people stay in situations longer than they should because the current structure feels safe or familiar.

Eventually the lack of upside becomes the bigger risk.

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

AI is useful. I use it myself.But I also think people are overestimating what it can actually replace in tax work.The ha...
06/25/2026

AI is useful. I use it myself.

But I also think people are overestimating what it can actually replace in tax work.

The hard part usually isn’t generating an answer.

It’s reviewing:
• whether the structure actually works
• whether the allocations make sense
• whether the economics match what’s being reported
• and whether something looks wrong before it gets filed.

That judgment layer still matters.

Especially once multiple entities, investors, and allocations start interacting together.

Where do you think AI actually helps versus where it creates more problems?

06/23/2026

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

That’s usually not the part that creates problems.

The harder part is defending:
• material participation
• operational involvement
• and activity tracking once the portfolio grows.

As more responsibility shifts to managers or teams, the qualification analysis usually becomes much more nuanced than people expect.

That’s where I see a lot of issues show up later.

Especially once someone starts trying to defend the position during an audit.

How are investors handling REP documentation as portfolios scale?

A lot of fund managers assume the tax side is fine because the returns are getting filed and the numbers look correct.Th...
06/22/2026

A lot of fund managers assume the tax side is fine because the returns are getting filed and the numbers look correct.

That’s usually not where the real gaps are.

The bigger issues are often things nobody addressed early enough:

• allocation inefficiencies
• entity structure decisions
• depreciation strategy
• investor reporting
• or planning around future exits.

A return can be technically correct and still miss larger strategic opportunities inside the fund.

As structures get bigger, the complexity compounds fast.

More investors.
More entities.
More reporting pressure.
More moving parts.

That’s usually when fund managers start realizing there’s a big difference between general compliance work and someone who actually works inside these structures every day.

Where do you think most fund managers outgrow their original CPA relationship?

06/20/2026

A lot of people in this industry start in very traditional tax environments before eventually finding a niche they actually want to build inside long term.

That was a big part of my path too.

Over time I realized I was much more interested in the operational side of real estate funds and how these structures actually functioned beyond just filing returns.

That eventually became the foundation for the work I focus on now.

I think most people eventually realize there’s a specific type of work and client they actually enjoy building around long term.

What pushed you toward the niche or industry you’re in now?

One of the reasons I focus so heavily on private equity real estate fund managers is because fund structures become very...
06/19/2026

One of the reasons I focus so heavily on private equity real estate fund managers is because fund structures become very different once they start scaling.

More investors.
More reporting.
More entities.
More operational overlap between the fund, management company, and ownership structure.

At a certain point, the tax side stops being “just compliance.”

That’s usually when:
• allocation issues start surfacing
• investor reporting gets more complex
• entity structure matters more
• and long-term planning becomes much more operational.

I’ve been on both sides of the table, and I think that perspective changes how you approach these structures.

What do you think becomes the hardest operational issue once a fund starts growing?

06/18/2026

A lot of people assume growth in a firm happens all at once.

Usually it doesn’t.

Most of the time it’s incremental decisions over years:
1. who you hire
2. how you structure operations
3. where you build leverage
4. what kind of clients you actually want to work with long term.

That’s really how Stonehan was built.

Not overnight. Not through one big moment. Just consistent decisions stacked over time.

What’s been the biggest operational change that helped your business scale?

Most fund managers think about the operating agreement as legal paperwork.The reality is it controls a lot more than peo...
06/17/2026

Most fund managers think about the operating agreement as legal paperwork.

The reality is it controls a lot more than people realize:
• allocations
• depreciation flow
• distributions
• waterfall mechanics
• and investor economics.

I’ve seen deals perform well operationally while the agreement language created tax outcomes the manager never expected. Usually the issues don’t show up early.

They show up later:
• during K-1 prep
• during distributions
• or when investors start questioning how the economics are flowing through the structure.

At that point, changing things becomes much harder. That’s why operating agreements deserve much more tax review than most fund managers give them upfront.

How often do you think fund managers actually revisit their operating agreement after formation?

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?

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