Aloha, It’s Shelon "Hutch" Hutchinson here! If you’re enjoying 'The Multifamily Real Estate Experiment' podcast, please like, comment, and share our episodes to help us reach and inspire more people. Thank you for your support!

On the Multifamily Real Estate Experiment podcast, host Shelan Hutcheson interviews Stewart, a longtime CPA turned real estate investor/operator, about how sophisticated investors evaluate deals and risk. Stewart’s mantra is “you make your money on the buy,” emphasizing disciplined underwriting, firm maximum pricing, and starting with low offers; he notes price impacts loan costs, fees, insurance, and overall returns. He defines investment risk largely as the likelihood of a downturn in the first five years causing foreclosure or a loss sale, often driven by over-leverage. Stewart explains evaluating real estate “like a CPA,” focusing on core P&L line items, NOI, cap rates, and detailed diligence on maintenance patterns, property taxes resetting to market value after sale, and tenant payment history. He contrasts NOI with distributable cash flow affected by debt service, prefers stabilized properties with fixed-rate debt, targets minimum 5% cash-on-cash year one, stresses preventative maintenance and reducing turnover costs, and highlights proactive tax planning and bonus depreciation. The conversation ends with his communication-first approach and a discussion of building and transferring assets to his children, including ideas from Die With Zero.

00:00 Welcome and Setup

00:58 Make Money on Buy

02:41 Lowball Offers Strategy

03:34 Stewart CPA Background

05:32 Defining Real Risk

06:49 Analyze Like a CPA

07:53 Due Diligence Questions

10:06 Cash Flow vs IRR

11:30 Boring Fixed Debt

13:54 Maintenance and Turnover

15:58 Boring Is Beautiful

17:52 Tax Planning First

20:10 Focus Round QandA

22:21 Leverage and LTV Limits

24:04 Legacy and Die With Zero

27:15 Closing Thanks

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*

Thank you to all of our listeners!!! We would love to hear from you!!!

Email me at:
hutch@hsquaredcapital.com

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
Visit our website to find out more:
www.hsquaredcapital.com

Join our Facebook Group:
The Multifamily Real Estate Experiment

Follow us on Instagram:
@hutchthemarineinvestor

Aloha, It’s Shelon "Hutch" Hutchinson here! If you’re enjoying 'The Multifamily Real Estate Experiment' podcast, please like, comment, and share our episodes to help us reach and inspire more people. Thank you for your support!

Risk is not just about whether an investment looks good on paper. It is about understanding what could cause you to lose money and preparing for it before you invest. 🧠📊

For Stewart, one of the biggest areas to watch is leverage. Debt can be a useful tool, but taking on too much can quickly change the risk profile of an investment.

That is why he believes real estate should be evaluated like a CPA, not a promoter. 🔍🏢

Strip away the excitement and look at the fundamentals. What is the income? What are the management costs, maintenance expenses, insurance, taxes, and other obligations?

Whether you are evaluating a duplex or a much larger property, disciplined investing starts with understanding the numbers and asking what could go wrong before focusing on what could go right. 💡

Good investors look for opportunity. Disciplined investors also understand the risk.

#RealEstateInvesting #RealEstateInvestor #RealEstate

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*

Thank you to all of our listeners!!! We would love to hear from you!!!

Email me at:
hutch@hsquaredcapital.com

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
Visit our website to find out more:
www.hsquaredcapital.com

Join our Facebook Group:
The Multifamily Real Estate Experiment

Follow us on Instagram:
@hutchthemarineinvestor

Aloha, It’s Shelon "Hutch" Hutchinson here! If you’re enjoying 'The Multifamily Real Estate Experiment' podcast, please like, comment, and share our episodes to help us reach and inspire more people. Thank you for your support!

Big wins get attention, but Stewart believes real progress is usually built somewhere much less exciting. 📈🧠

It comes from doing the basics well, day after day.

That is where his philosophy of “boring is beautiful” comes from. Instead of always chasing the newest or most exciting opportunity, Stewart values consistency, discipline, and understanding what you own. 🏢

There is a bigger lesson here than real estate.

In business, leadership, and investing, the fundamentals can feel repetitive. They rarely make headlines. But showing up, following a sound process, and staying focused on what works can matter more than constantly looking for the next exciting move. 💪🏾🎯

Sometimes boring is not a weakness.

Sometimes it is a sign that you have learned to value consistency over excitement. 👏🏾

#RealEstateInvesting #RealEstateInvestor #InvestorMindset

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*

Thank you to all of our listeners!!! We would love to hear from you!!!

Email me at:
hutch@hsquaredcapital.com

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
Visit our website to find out more:
www.hsquaredcapital.com

Join our Facebook Group:
The Multifamily Real Estate Experiment

Follow us on Instagram:
@hutchthemarineinvestor