The Multifamily Real Estate Experiment Podcast

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

Email me at:
[email protected]

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

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The Multifamily Real Estate Experiment

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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

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

Email me at:
[email protected]

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

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

Stewart shares a negotiation lesson that has stayed with him for years:

“If you're not embarrassed by your first offer, you're offering too much.” 😅

The point is not to throw out random numbers. It is to know your numbers well enough to make an offer with confidence, even when it feels uncomfortable. 📊

Sometimes the answer will be no. Sometimes the response may surprise you.

That mindset connects directly to Stewart’s background as a CPA. After more than three decades working with numbers, he naturally approaches real estate through analysis, discipline, and understanding what makes sense before moving forward. 🧠🏢

Strong negotiation starts with preparation. Know your numbers, understand your position, and do not be afraid to ask.

#RealEstateInvesting #NegotiationSkills #InvestorMindset

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

The Focus Round gave us a different look at Stewart. 🎯

From walking real estate for fun 🏢 to the late-night tax season realization that pushed him toward investing, his journey has been shaped by paying attention to what was happening around him.

One lesson became especially important along the way: communicate early and communicate often. 🗣️

Stewart admits that communication was not always one of his strengths. Experience taught him that investors, tenants, and the people depending on your leadership should not have to wonder what is happening.

And today, his definition of success has changed too. It is less about simply making more money and more about building assets his children may one day benefit from and potentially pass forward to the next generation. 👨‍👩‍👧‍👦🏢

That is a powerful shift in mindset.

Success is not only about what you build for yourself. It is also about what your decisions, habits, and communication allow you to build for the people coming after you. 💭💪🏾

#RealEstateInvesting #Leadership #GenerationalWealth

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

“You make your money on the buy, not the sell.” 🏢💭

For Stewart Heath, that mantra comes down to one thing: discipline before the decision.

Exceptional investors do the work on the front end. They study the numbers, understand the asset, and decide what they are willing to pay before emotion or competition enters the picture. 🔍📊

Because once you are in the deal, you are in it.

What you pay at the beginning can influence the entire life of an investment. That is why Stewart believes strong investing starts with knowing your limits and having the discipline to stick to them. 💪🏾

It is a real estate lesson, but it is also a leadership lesson. Set your standards before the pressure shows up. 🧠

Strong decisions usually start long before the final handshake.

#RealEstateInvesting #MultifamilyInvesting #InvestorMindset

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

Host Shelon “Hutch the Marine Investor” Hutchinson interviews Marine veteran and real estate investor Keith Gillispie about building a business that can run without the owner. Gillispie shares his mantra “keep the most important thing the most important thing,” rejects the idea of static work-life balance, and explains how he used a one-hour lunch break in Hawaii—hotspot, headphones, 50–55 minutes of seller calls, protein-shake lunch—to lock up 10 contracts in six months, leading to REI Automated and SOP-driven delegation with virtual assistants worldwide. He discusses virtual investing across 34 states, what should and shouldn’t be automated, and how to choose creative-finance tools by evaluating seller needs, business needs, personal needs, market cycle, and highest-and-best use. He outlines an education-first private-capital process learned from a $1.135M Diamond Head deal, using third-party validation and a one-sheet/Google Drive package. Gillispie cites Ray Dalio’s Principles and Gino Wickman’s Traction (EOS) as pivotal, recommends daily walks, regrets not holding assets earlier, and defines success as meaningful impact and leading people to God, sharing contact info and REI Automated details.

00:00 Show Kickoff

00:22 Meet Keith Gillespie

02:09 Core Mantra Priorities

03:40 Work Life Balance Myth

06:42 Lunch Break Blueprint

07:59 Time Zone Constraints

10:52 Car Calls System

12:46 Virtual Investing Systems

14:12 Automation Vs Human Touch

15:13 SOPs And Virtual Assistants

17:56 Creative Financing Tools

19:32 Five Lever Deal Key

23:28 Education First Capital

24:47 Diamond Head Case Study

26:07 Killer Deal Breakdown

27:14 Mentor Ultimatum Funding

29:04 Golden Rule Scarcity

31:17 One Sheet Proof Pack

34:40 Pitch Without Asking

35:40 Network Resourcefulness

39:32 Focus Round Recharge

41:35 Books That Changed Everything

45:57 Rapid Fire Lessons

47:14 Defining Real Success

52:13 Where To Find Keith

53:18 Final Thanks Sign Off

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

In this part of the podcast, Hutch and Keith explore a business lesson that completely changed the way Keith viewed money, opportunity, and negotiation.

Most people assume capital is the most valuable piece of any transaction. But what happens when the opportunity itself is far more difficult to find? 💰🏠

Through a simple example about scarcity, Keith explains why value can shift depending on what is available, what is needed, and who recognizes the opportunity first.

This mindset can influence how investors approach negotiations, partnerships, and the deals placed in front of them. Sometimes, the greatest leverage is not having the money. It is understanding what everyone else is searching for. 🎯

Watch the clip to hear the business version of the golden rule and the lesson that changed Keith’s perspective.

#RealEstateInvesting #InvestorMindset #BusinessStrategy #Entrepreneurship

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

In this part of the conversation, Keith breaks down the decision-making framework he uses before choosing what to do with a property.

A deal is not decided by one number alone. The seller’s situation, the needs of the business, personal priorities, market conditions, and the property’s potential all influence the final decision. 🏠📊

The key is knowing how those factors work together.

Sometimes the right move is to sell. Sometimes it is to hold. Other times, the opportunity may be hidden in how the property can be improved or repositioned.

Strong investors do not force every property into the same strategy. They study the full picture, identify the available levers, and make the decision that fits the moment. 🎯

Watch the clip to hear the five-part combination Keith uses to evaluate and unlock a deal.

#RealEstateInvesting #InvestorMindset #PropertyInvesting #BusinessStrategy

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

Email me at:
[email protected]

*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*=*
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!

In this part of the podcast, Hutch and Keith unpack what it really looks like to pursue a new future while serving on active duty, traveling overseas, and trying to remain present for your family.

There was no perfect schedule. Mornings were already spoken for. Evenings came too late. Sleep was disappearing, and the pressure was becoming unsustainable. 🌍💭

The turning point came when Keith stopped searching for more time and started protecting the small window he still had.

What followed was not glamorous. It required sacrifice, consistency, and a reason strong enough to keep going when the schedule said it was impossible. 🎯

Sometimes progress does not come from having more hours. It comes from becoming more intentional with the hours already available.

How much could change if you protected one focused hour every day?

#LeadershipMindset #MilitaryVeterans #RealEstateInvesting #Entrepreneurship

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

Email me at:
[email protected]

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

Join our Facebook Group:
The Multifamily Real Estate Experiment

Follow us on Instagram:
@hutchthemarineinvestor