In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about taxes, capital gains, and how to stay bankable while paying as little as legally possible.

Keith shares the story of a five-unit property on five acres that he had under contract for around $750,000. The numbers showed he could live for free and cash flow $4,000 to $5,000 a month, but his CPA had written off so much that the lender saw him as broke on paper. The deal fell apart, and that property is now worth about $1 million.

From there, Keith explains how he now keeps his taxes low while still qualifying for loans, why he meets with his CPA every month instead of rushing in April, what he looks for in a great CPA, and why business owners should set a clear goal and let their experts lead.

Takeaways:

• Writing off everything can cost you your next deal.
• You can pay almost nothing in taxes and still stay bankable.
• Meet with your CPA every month instead of scrambling in April.
• The right CPA gets excited about tax code and specializes in real estate.
• Give your team clear direction and then let the experts lead.

Chapters:

00:00 Introduction

00:48 Strategies for Capital Gains Tax Reduction

05:06 Real Estate Investment Insights

10:04 Navigating Tax Legislation Changes

17:56 Choosing the Right CPA

27:55 Handling Depreciation and Selling Properties

33:10 Outro

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🏠FREE Facebook Community: 

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🧑🏻‍💻FREE COURSE (watch 5 min first): 

https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: 

https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

SOCIALS

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to break down how his acquisition process evolved from an inconsistent, overcomplicated system into a repeatable process built around principles.

Keith explains how taking multiple courses early in his career actually led him to combine several different systems into one bloated process, why it took him years to develop repeatability, and why every system he uses today exists because of a problem he has already experienced firsthand.

From there, the conversation moves into mentorship, paying for shortcuts, the true value of time, and the mistakes Keith made while building his first team.

Takeaways:

• Why overeducation can sometimes lead to overanalysis 
• How combining several good systems can create one terrible system
• Whether it's better to pay a mentor or learn everything through trial and error
• Why Keith views time as a more valuable currency than money
• How coaching can shorten the path to your first deal
  

Chapters:

00:00 Introduction to Real Estate Investing

00:48 Evolution of Acquisition Processes

10:38 The Value of Mentorship vs. Experience

22:36 Building a Team for Success

34:04 Outro

🎁FREE Goal Setting Masterclass: 

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📊FREE Deal Analyzer + Repair Estimator: 

https://go.reiautomated.io/deal-analyzer 

📃FREE Joint Venture Agreement: 

https://go.reiautomated.io/jv-agreement-flm 

🏠FREE Facebook Community: 

https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): 

https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: 

https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

SOCIALS

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Keith starts by sharing how he brought on both a partner and a virtual assistant almost immediately after launching his investing business in 2016 — and why he now believes hiring that early was a mistake.

He then walks through the 55% maximum leverage rule he personally uses across his rental portfolio and explains how he built that number by studying major historical market downturns.

Finally, Keith explains why investors managing rentals in multiple markets should stop trying to do everything themselves and hire an exceptional property management company instead.

Takeaways:

• Why partnering on your first deal will help you “earn while you learn”
• The difference between hiring a generalist and hiring a specialist
• Why every recurring task should have a documented SOP
• Why you shouldn't expect an employee to create your business systems for you
• How Keith developed his personal 55% maximum portfolio leverage rule and how you can use it too
• Why Keith believes paying 10% for excellent property management is worth it
• Why websites and five-star reviews aren't enough when choosing a manager

Chapters:

00:00 Introduction

00:48 The Relentless Pursuit of Success

01:58 Starting Out in Real Estate Investing

06:39 The Importance of Leadership and Team Dynamics

11:35 Understanding Market Cycles and Financial Safety

15:50 Leveraging Real Estate Investments Wisely

20:58 Choosing the Right Property Management Company

24:12 Outro

🎁FREE Goal Setting Masterclass: 

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📊FREE Deal Analyzer + Repair Estimator: 

https://go.reiautomated.io/deal-analyzer 

📃FREE Joint Venture Agreement: 

https://go.reiautomated.io/jv-agreement-flm 

🏠FREE Facebook Community: 

https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): 

https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: 

https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

SOCIALS

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Facebook: https://www.facebook.com/Keith.Gillispie

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to break down the progression from residential real estate into multifamily and commercial investing. They discuss the different paths investors can take after single-family properties, economies of scale in multifamily, why commercial brokers matter, how commercial deals are underwritten, seller financing, and why Keith believes parts of commercial real estate can actually be simpler than residential investing.

Keith also breaks down what happens operationally as a real estate business grows.

He explains how managing too many direct reports became a major bottleneck, why Traction and the EOS framework changed the way he managed his teams, how automation helped reduce his sales team from 18 reps to three while increasing throughput, and why every period of “stabilization” may actually be a sign that you've hit your next core constraint.

Takeaways

• Transition from residential to commercial real estate
• Three types of real estate investors Effective communication is crucial for scaling a business
• Identifying and addressing core constraints is essential for sustained growth

Chapters

• 00:00 Introduction
• 00:48 The Transition from Residential to Commercial Real Estate
• 04:11 Understanding Multifamily Investments
• 09:44 The Learning Curve in Commercial Real Estate
• 15:31 The Collaborative Nature of Commercial Real Estate
• 20:44 Operational Challenges in Scaling Investments
• 21:33 Navigating Team Dynamics and Communication
• 28:00 The Importance of Stabilization in Growth
• 39:51 Identifying and Overcoming Core Constraints
• 43:10 Outro

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🏠FREE Facebook Community: 

https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): 

https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: 

https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

SOCIALS

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about the real estate deals and business decisions that don't go according to plan. They break down a foreclosure deal Keith couldn't save, what “passive income” actually looks like with rentals and promissory notes, the role of property and note management, the moments that nearly took Keith out of entrepreneurship, and why financial management matters as your business grows.

Keith also opens up about spending more than $250,000 on mentorship during his first four years, carrying as many as 22 credit cards, and later spending roughly $25,000–$30,000 per month on advertising while scaling a business whose numbers he couldn't properly see. He explains how poor execution, unchecked expenses, and high-interest debt became some of his most expensive lessons—and why taking action on what you learn matters more than endlessly consuming more information.

Takeaways

• Real estate investing challenges
• Passive income from real estate
• Dealing with bad debt

Chapters

• 00:00 Introduction
• 00:48 Real Estate Challenges
• 09:48 Understanding Passive Income in Real Estate
• 14:40 Overcoming Obstacles in Real Estate Investing
• 29:38 Final Thoughts and Key Takeaways
• 31:01 Outro

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🏠FREE Facebook Community: 

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🧑🏻‍💻FREE COURSE (watch 5 min first): 

https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: 

https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

SOCIALS

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Facebook: https://www.facebook.com/Keith.Gillispie

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about working with your spouse in real estate, dividing responsibilities inside the business, getting aligned on goals and risk, choosing the right mentors and books, and avoiding productivity habits that make you feel busy without actually making progress.

Keith shares lessons from working alongside his wife, Miranda, during the early years of his real estate career — including why cross-training matters, how they divided responsibilities based on strengths, and the one rule he believes has to stay above everything else

Takeaways:

• When considering real estate investing with a spouse, it's crucial to align visions, communicate effectively, and prioritize the marriage over the business.
• Recommended books, mentors, and communities can provide valuable insights and guidance for personal and professional development.
• Why spouses should be cross-trained even when they have separate primary roles 
  

Chapters:

00:00 Introduction

00:48 Sickness Stories and Resilience

01:04 Mindset in Real Estate Investing

02:09 Working with Spouses in Business

08:03 Aligning Visions and Goals

12:15 Influential Books and Mentorships

21:06 Prioritizing Productivity Over Routine

25:27 Outro

🎁Goal Setting For Couples: 

https://knowledge.reiautomated.io/courses/self-mastery 

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📊FREE Deal Analyzer + Repair Estimator: 

https://go.reiautomated.io/deal-analyzer 

📃FREE Joint Venture Agreement: 

https://go.reiautomated.io/jv-agreement-flm 

🏠FREE Facebook Community: 

https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): 

https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: 

https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

SOCIALS

Instagram: https://www.instagram.com/keithg_rei/ 

Facebook: https://www.facebook.com/Keith.Gillispie

Music from #Uppbeat (free for Creators!):

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith to talk about what financial freedom looks like after a decade of investing, why people get stuck preparing to invest for years without taking action, and how Keith thinks about real estate within a much larger wealth-building strategy.

Keith explains why he now thinks of financial freedom as “choice freedom” — the ability to decide what to do, when to do it, who to do it with, and how long to do it.

From there, the conversation moves into family, entrepreneurship, investing, sales, diversification, and the three things Keith believes almost every struggling new investor is missing: education, systems, or support.

Takeaways

• Mindset is key to achieving financial freedom
• Financial freedom is about choice freedom, not just money
• Real estate is a key wealth-building asset

Chapters

• 00:00 Introduction
• 00:48 The Essence of Financial Freedom
• 08:41 Evolving Perspectives on Wealth
• 15:53 Taking Action in Real Estate Investing
• 17:25 Integrating Real Estate with Broader Wealth Strategies
• 24:27 The Path to Millionaire Status
• 25:32 Outro

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📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm 

🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

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SOCIALS

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In this episode of The First Deal Podcast, Dayton Lindsey and Keith Gillispie break down how Keith thinks about self-directed retirement accounts, Solo 401(k)s, DSCR loans, private money, leverage, and funding your next several deals without waiting years to stockpile cash.

Keith explains why he strongly prefers a self-directed Roth Solo 401(k) over an IRA for his own investing, how he has used retirement-account funds for earnest money deposits, and why he believes investors need qualified professionals in their corner before making decisions involving retirement accounts or taxes.

Takeaways

• Self-directed IRAs and solo 401(k)s offer benefits for real estate investment
• DSCR loans and private money raising strategies are crucial for funding real estate deals

Chapters

• 00:00 Introduction
• 00:48 Understanding Self-Directed IRAs and Solo 401(k)s
• 05:39 The Benefits of Solo 401(k)s Over IRAs
• 11:26 Exploring Health Savings Accounts (HSAs) and Tax Benefits
• 17:21 The Importance of Debt Service Coverage Ratio (DSCR) Loans
• 23:42 Capital Stacking Strategies for Real Estate Investing
• 28:39 Outro

📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm 

📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer 

📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm 

🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8 

SOCIALS

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Facebook: https://www.facebook.com/Keith.Gillispie

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to talk about risk, leverage, passive investing, and the importance of knowing when not to force a deal.

Keith starts with the story of a massive oceanfront property in Kailua, Hawaii that he had under contract for roughly $1.8 million, with a potential ARV north of $3 million. On paper, the spread looked incredible. In reality, uncertain comps, structural problems, mold and water damage, and potentially hundreds of thousands of dollars in renovations made the downside impossible to ignore.

Takeaways

• Risk Aversion
• Passive Investing

Chapters

• 00:00 Introduction
• 00:48 The Biggest Deal Keith Has Ever Walked Away From
• 11:54 Understanding Real Estate Syndications
• 16:54 Refinancing Properties for Equity
• 24:52 Tax Strategies and Real Estate Investing
• 33:04 Outro
  

  📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm 

  📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer 

    

  📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm 

  🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling  

  🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

  🌐Our Website: https://www.reiautomated.io 
  

  🎯DealBase - The Only CRM Built For Real Estate Investors: https://go.reiautomated.io/dealbase-reia  
  

  🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

  WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8 
  

  SOCIALS

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In this episode of The First Deal Podcast, Dayton Lindsey sits down with Keith Gillispie to break down several real estate strategies investors may overlook — including co-living and rent-by-the-room rentals, choosing the right market, and investing in mobile and manufactured homes.

Takeaways

• Rent by room strategy increases cash flow significantly
• Mobile homes offer high cash on cash return and financing opportunities

Chapters

• 00:00 Introduction
• 00:48 Exploring Rent by Room Strategies
• 09:05 Market Evaluation for Real Estate Investments
• 16:01 Insights on Mobile Home Parks and Manufactured Housing
• 23:00 Outro

📜FREE Purchase & Sales Agreement: https://go.reiautomated.io/strongest-psa-lm 

📊FREE Deal Analyzer + Repair Estimator: https://go.reiautomated.io/deal-analyzer 

📃FREE Joint Venture Agreement: https://go.reiautomated.io/jv-agreement-flm 

🏠FREE Facebook Community: https://www.facebook.com/groups/realestateinvestingandwholesaling  

🧑🏻‍💻FREE COURSE (watch 5 min first): https://playbook.reiautomated.io/?source=Keith&campaign=OFC 

🌐Our Website: https://www.reiautomated.io 

🎯DealBase - The Only CRM Built For Real Estate Investors: https://go.reiautomated.io/dealbase-reia  

🌟CLIENT RESULTS: https://youtu.be/wtDCqarJceM?si=QsXJyAKV6eVL-Eeb 

WHAT WE OFFER: https://youtu.be/JbV0LqjdhJ8 

SOCIALS

Instagram: https://www.instagram.com/keithg_rei/ 

Facebook: https://www.facebook.com/Keith.Gillispie

Music from #Uppbeat (free for Creators!):

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License code: OZZJFTOT1V6EYPPY