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

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Email me at:
hutch@hsquaredcapital.com

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