Becoming a High Level Real Estate Strategist, Tax and Structures Explained
Featuring: Steven Arita (Path to Passive Podcast) and James Bohan, CPA, MRED
This conversation originally aired on the Path to Passive Podcast, hosted by Steven Arita, a show designed to help investors build wealth through smarter strategies and better structures. In this episode, Steven interviews James Bohan, CPA, founder of Stonehan Accountancy, real estate investor, and former CFO by age 30.
James breaks down how tax planning, entity structuring, wealth preservation, and financial discipline shape the long term success of fund managers, syndicators, and high net worth families. This episode is especially valuable for tech professionals entering real estate, GPs and LPs scaling into larger deals, and operators who want to build multi generational wealth.
Summary:
Real estate wealth is built through intentional structure, long term strategy, clean operations, and disciplined decision making. In this episode, James explains:
The mindset that helped him become a CFO at age 30
How fund managers should structure their business
What a family office actually is and how it preserves wealth
The four entity “food groups” every investor needs
Why most family wealth disappears by the third generation
The tax strategies that move the needle
When investors really need a CPA
Christian stewardship and ethical entrepreneurship
James also shares practical and philosophical insights on scaling a real estate business, designing your life intentionally, and building legacy systems that last.
Watch the Full Episode:
FAQ's
1. What is the meaning of the entity “food groups”?
It refers to the four essential entity types every serious investor eventually needs: LLCs, S corporations, C corporations, and trusts.
2. Why do most family offices exist?
To preserve wealth across generations through structure, tax planning, governance, and centralized management.
3. Why does real estate professional status matter?
It allows active investors to use depreciation to offset ordinary income, creating powerful tax advantages.
📞 Book a Tax Strategy Call with James:
https://calendly.com/jamesbohan/book-a-call
📨 Connect With James:
LinkedIn: James Bohan, CPA, MRED
Instagram: @jamesbohancfo
Website: stonehan.com
Chapter Breakdown With Timestamps:
00:00, Intro and the mindset of “don’t quit”
00:27, Who James is and what he does
01:45, CFO by 30, speeding through corporate America
03:55, Accounting and real estate vertical explained
06:20, How fund managers should structure their business
09:10, What a family office actually is
12:44, Entity food groups: LLC, S corp, C corp, trusts
16:35, Wealth preservation and succession planning
19:52, Why most family wealth disappears by generation three
22:18, Tax strategy: STR loophole, REP status, depreciation
26:40, When you need a CPA, and when you do not
29:25, Christian business principles and entrepreneurship
32:00, Money, stewardship, and legacy
34:15, Final advice: never quit
35:02, How to connect with James
Original Episode:
This conversation originally aired on the Path to Passive Podcast.
Watch here: https://www.youtube.com/watch?v=TZyeJFNkg58
Full Transcript:
00:00 Intro and welcome
Steven (00:00):
Welcome to the Path to Passive Podcast, where we talk about building wealth and an empowered lifestyle through commercial real estate, especially for tech professionals. I always wished more people documented their journey to financial freedom, so I am doing that for the rest of us. James, welcome to the show. I really appreciate having you here. It is wild that it has already been a couple of months since our chat at RaiseFest. I also saw you speak at the Raise Masters retreat in San Diego last year, and time really flies. You are the CEO and founder of Stonehan Accountancy, you have a background in real estate finance, Big Four, institutional and family office experience, and entrepreneurship. We have a couple of topics I think will be very valuable for listeners. How do you like to introduce yourself and what do you want to be known for?
James (01:05):
Thanks for having me, Steven. At my core, I am an entrepreneur. Inside that, I really run two verticals. The first is my accounting firm, Stonehan Accountancy, where we help real estate professionals, investors, and syndicators minimize taxes and structure their funds properly. We also handle bookkeeping and make sure the books are balanced, which is vital when you are managing other people’s money. The second vertical is my real estate development and investment business, which has a bit of a family office flavor. I moved to Idaho about four years ago and started buying properties here. In the last three months we have closed on two more and I am working on scaling that platform. I am currently in fund formation with counsel to take advantage of opportunities I see in Idaho and the broader Mountain West. That includes smaller residential deals, micro multifamily, hospitality, Airbnbs, and boutique hotels. My philosophy is simple: if it makes dollars, it makes sense.
01:45 CFO by 30 and “speed running” corporate America
Steven (01:45):
I love that. With your background, that makes perfect sense. One thing that really stands out is that you became a CFO by 30. You sometimes call it “speed running” corporate America. How did that happen?
James (01:58):
I owe a lot of that to my accounting career. I am also a gamer, so the “speed run” analogy comes from watching people try to beat games like Mario or Zelda as fast as possible. I started at a firm called Rothstein Kass, which was later acquired by KPMG. In public accounting you are exposed to so much, and you end up working closely with CFOs and executives at your clients. I focused on real estate funds and alternative investments, mainly hedge funds and private equity funds, which let me combine my family’s real estate background with an institutional view of the asset class. I tell people all the time that grad school is a great reset button. If you have been a CPA for a while, people often pigeonhole you as “back office,” but it is not impossible to move to the front office. I went back and got my master’s in real estate development. One of my professors was starting a debt fund and hired me as his first employee. Within a year I was promoted to CFO. While I was there, we originated over a billion dollars of loans and onboarded about 1,400 LPs. It was a great experience to see what it looks like to build and scale a fund from inception.
03:55 Accounting plus real estate and building a family office
Steven (03:55):
That is incredible experience. You have seen what matters to LPs and how the back office really works. You have also spent a lot of time around family offices and now you are building your own. Tell us about that.
James (04:07):
For the last few years I have been building toward a family office structure for my own family. I have been testing technologies and tools that I can also recommend to clients. That includes spend management, bill pay, treasury, and consolidated financials. For a while I was trying to force QuickBooks to do more than it was built to do. Eventually I ran a full RFP and decided to move to Oracle NetSuite. At a certain point, the per entity cost of enterprise software starts to look similar to what you are paying for workarounds anyway. NetSuite is built for consolidations and high level reporting, which family offices need.
06:20 What a family office actually is
Steven (06:20):
This is a newer topic for many listeners. I got very excited the first time I heard about family offices. It is like an elite, structured way to manage wealth. How do you explain what a family office is to someone hearing about it for the first time?
James (06:35):
One story I like to use is about a hedge fund manager who got banned from trading other people’s money by the SEC. He basically said, “Fine, I will just trade my own,” and built a structure just for that. That is essentially the family office concept. A family office is a structure set up to manage a family’s wealth in a professional way, similar to how a private equity or hedge fund would operate, but for the benefit of one family. When you get to, say, one hundred million dollars of investable assets, paying a wealth manager one percent a year is a million dollars. For that same million, you can hire your own team: investment professionals, accountants, attorneys, and operators who are solely focused on your family’s goals. There are single family offices, multi family offices where multiple families pool resources, and real estate focused family offices that mainly manage operating assets rather than securities. But the core idea is the same. It is a dedicated team and system for investing and preserving the family’s wealth.
09:10 Who should think about a family office and entity “food groups”
Steven (09:10):
That is helpful. For someone on the journey, what milestones should they hit before thinking in family office terms? And how are you structuring yours?
James (09:22):
It can start sooner than people think. Some multi family offices will work with families in the ten to fifty million dollar range. Sometimes those fortunes come from operating companies that are not in finance at all, like manufacturing or appliance sales. On my side, I am building what you might call a multi family office service model. I am a CPA and already running the accounting firm, so I can bring that experience to other families who want structure but do not know where to start. A big part of the conversation is legacy and succession planning. Do they want to sell everything and travel? Do they want a charitable foundation? What do they want their kids and grandkids to inherit, if anything? That is where I talk about “entity food groups.” You generally want:
At least one LLC or partnership to hold operating assets
An S corporation for active business income and payroll
A C corporation for certain fringe benefit strategies
One or more trusts for legacy, estate, and asset protection
Then you can layer on charitable tools like donor advised funds or foundations depending on their goals.
16:35 Wealth preservation, estate tax, and dynasty trusts
Steven (16:35):
You mentioned erosion of wealth by the third generation. That is a common stat people throw around. How does planning actually help prevent that?
James (16:45):
Without planning, the erosion is almost guaranteed. There are two big forces at play. One is simple math. Wealth tends to get split with each generation. A billion dollars split a couple of times and taxed heavily can turn into ten to fifty million by the time it hits the grandkids. That is still a lot of money, but it does not have the same economic power or options. The second is estate tax. Right now, a married couple has about a 26 million dollar exemption. Everything above that gets hit at roughly 40 percent when you die. That is a huge haircut. Trusts are one of the main tools to fight that. They move assets out of your personal estate. You have grantors who fund the trust, trustees who manage it, and beneficiaries who receive distributions. With the right structure, assets can grow inside the trust outside your taxable estate. Dynasty trusts are designed to last across generations. You can think of them like an LP that your family office manages. The trust owns the assets; your structures and teams manage and grow them. It is a way to keep wealth compounding without having it chopped down by estate tax every generation.
22:18 Practical structures for high earners and small business owners
Steven (22:18):
For someone earlier on the path, say a high earning listener with a few LP investments and maybe a small business, what are the more practical first steps?
James (22:29):
Most high earning professionals should at least have:
A revocable living trust to avoid probate and handle basic estate wishes
A holding company, often an LLC in a favorable state like Wyoming, owned by that trust
Their LP and investment interests held through that LLC. If they run an active business or practice, that is usually where an S corporation structure comes in, to optimize how income is taxed and to handle payroll. They do not necessarily need dynasty trusts at that level, but they should be intentional about how assets are titled and where income flows. That alone can make a meaningful difference over time.
26:40 Tax strategy, STR loophole, REP status, and when you need a CPA
Steven (26:40):
You have mentioned some powerful tax strategies. For someone listening who is thinking about taxes more seriously, where do you start? And when do they really need a CPA instead of TurboTax?
James (26:52):
There are a few buckets. One big one is the short term rental strategy. For high income tech professionals, buying and personally managing a short term rental can unlock major deductions if structured correctly. My own family uses a version of this. My wife got her real estate license and handles management. I have too many CPA hours to qualify, but she can qualify for Real Estate Professional Status, and that allows certain losses to offset active income. In terms of tools, TurboTax is fine for a straightforward W2 and maybe a small Schedule C. But once you start investing in LP deals that generate multiple K1s, sometimes in multiple states, or you add entities and real estate, it gets complicated fast. That is where a CPA who understands real estate and fund structures becomes important. We offer tax consulting packages where we look at the entire picture and design a structure that actually fits the client’s life instead of just filling in software fields.
29:25 Christian business principles in a secular world
Steven (29:25):
You also talk openly about being a Christian businessman in a secular world. What does that mean to you in practice?
James (29:35):
For me, it means profit is not the only filter. I still care a lot about performance, but I also care about how decisions affect people. I believe God has blessed me with certain skills and opportunities, and I see that as a call to stewardship. As you build a business and hire people, you are not just building something for yourself. You are helping feed multiple families. That adds responsibility and meaning. I try to be a fair and kind boss, without being a pushover. I want people to grow with the company. We hire overseas team members, for example in the Philippines, and I try to pay top of market so they can have a genuinely better life. Over time I would love to have more local employees as well and be a positive part of my community.
32:00 Money, stewardship, local life, and legacy
Steven (32:00):
How has your perspective on money and purpose shifted over time as your faith and career have evolved?
James (32:09):
Growing up in Southern California and LA, I used to think in terms of the big dreams. Yachts, global travel, that sort of thing. Over the last five years, especially since coming to faith, my focus has become much more local. My wife and I live on a farm in Idaho. We love our life here. Instead of wanting to be on a plane all the time, I want to invest in my community, my church, my family, and my businesses. For example, at one of our properties we host weekly farmers markets. It supports small local vendors and brings people together. From a faith perspective, I see money as something we steward, not something we ultimately own. It is a tool and a form of energy, not an identity. That mindset shapes how I think about building a family office, how I treat my team, and how I make long term plans.
34:15 Final advice and “never quit”
Steven (34:15):
This has been packed with insight, and I want to be respectful of your time. Any final advice for listeners before we wrap up?
James (34:23):
One idea that has been on my mind a lot lately is simple: do not quit. Quitting is the only way you truly lose. If you stay in the game, adjust, and keep moving forward, you keep giving yourself a chance to win. My dad used to say, “Quitters never win, and winners never quit.” It is cliché, but it is true. The path to passive income, building a family office, or growing a business is not linear. There are hard seasons. If you do not quit, you can work through them.
35:02 How to connect with James
Steven (35:02):
James, this has been fantastic. How can listeners connect with you or learn more?
James (35:08):
You can find me on LinkedIn as James Bohan, CPA, MRED. My website is stonehan.com. That is “stone” like a rock and “han” like Han Solo. There is a “book a call” option there if you want to talk tax strategy, family office structure, or investing. I am also on Instagram as @jamesbohancfo.
Steven (35:30):
Perfect. We will put all of those links in the show notes. James, thank you again for being here.
James (35:35):
Thanks for having me, Steven.
Steven (35:38):
And thanks to everyone listening to Path to Passive. If you enjoyed this episode, be sure to subscribe and let us know what topics you want to hear about next. We will see you on the next episode.
