The Commercial Real Estate Investor Podcast

Key Takeaways:

Practicing daily underwriting significantly improves deal analysis skills, and many viable deals can be found in common online marketplaces.

Tyler advised against purchasing a specific industrial condo deal due to unfavorable returns and risks, stressing the importance of careful deal evaluation.

For small family offices, use a holding company or trust with separate LLCs for each asset to maximize asset protection and management.

Work with a specialized real estate CPA for optimized tax planning and execute 1031 exchanges by preparing ahead of asset sales.

Allocate portfolios with a...

Key Takeaways:

Strong and growing flex space demand:

This trend is driven by e-commerce growth (like Amazon’s logistics), changes in urban development, and insufficient new supply of small bay industrial spaces.

Developer focus on larger projects leads to small space shortages:

Most new construction is for big warehousing, leaving limited availability of flexible, smaller units, especially near urban cores where older small bays are repurposed or demolished.

Versatility attracts diverse tenants and businesses:

Flex spaces serve trades, startups, studios, recreation, and more, allowing owners to backfill va...

Key Takeaways:

Building Trust and Relationships is Essential:

Evan Holiday was able to raise $1M in 24 hours not by chance, but by spending years building trust, credibility, and relationships with his audience.

Start Building Your Brand Early:

Successful fundraising starts long before the ask; by consistently sharing your journey, highlighting others, and demonstrating your values publicly.

Lead with Value, Not Just the Ask:

Evan created value for his network by focusing on others and providing insights, rather than only talking about his own business needs.

...

Key Takeaways:

Market Sentiment & Outlook:

Commercial real estate is facing uncertainty into 2026, primarily due to macroeconomic volatility, interest rates, and capital availability.

While capital was readily available previously, concern about raising funds or qualifying for loans is now considered the top risk by industry leaders.

Most investors still expect to increase real estate holdings to hedge against inflation and diversify portfolios.

Sector Performance & Trends:

Some sectors like digital economy properties (i.e., data centers), logistics, warehousing, and industrial are performing well and attracting attention.

Office...

Key Takeaways:

Embrace an Entrepreneurial Mindset:

Viewing downturns as opportunities and having determination are crucial for breaking into a new field like real estate.

Apply Past Experience:

Skills from other industries, such as hospitality, can be valuable—especially when focusing on meeting client needs and delivering exceptional personalized experiences.

Focus Local for Impact:

Building wealth and lasting business success can be achieved by investing in and serving a specific neighborhood, building deep roots, and understanding the unique opportunities and needs of that area.

Listen to th...

Key Takeaways:

Strategies for Hard-to-Sell Properties:

If a property (like a restaurant in Miami) won’t sell, don’t just focus on price; consider marketing it differently (e.g., as an event venue or multi-tenant investment).

Address non-price obstacles—such as lack of parking and negative owner reputation—possibly by bringing in a neutral negotiator.

Retail Market Challenges & Outlook (2025):

Retail remains resilient but faces major headwinds: tariffs have increased costs, consumer sentiment is softening, and lay-offs/store closures are rising.

Local, neighborhood-serving strip centers are considered more stable t...

Key Takeaways:

Commercial real estate isn't just for millionaires - it's about how you structure deals, not how much money you have.

Successful investment strategies include:

Finding overlooked properties

Building the right capital stack

Partnering with someone who has a unique edge

Focusing on operational improvements rather than major renovations

Underwriting conservatively

Specific example: Tyler and his partner Jacob bought a failing self-storage facility for $1.7 million by:

Raising capital from a small investor group

Leveraging Jacob's moving company for...

Key Takeaways:

Value Creation Over Cash Flow

Focus on creating equity, not just collecting monthly rent

Potential to make more money by improving property value than through steady cash flow

Example: Tyler's land deal generated $900,000 in three years versus minimal annual cash flow

Partnerships

Partnerships can be powerful for scaling your business

Always have a clear operating agreement

Avoid 50/50 partnerships; ensure someone has decision-making control

Choose partners with complementary skills

Underwriting Strategy

Consistently analyze different property types<...

Key Takeaways:

Value-Add Commercial Real Estate Strategy

Look for properties with potential for improvement

Opportunities exist in buildings needing work, like roof or HVAC upgrades

Potential to increase value by raising rents and converting to triple net leases

30-Day Challenge Launch

Free challenge for learning commercial real estate deal underwriting

Starts October 22nd

Provides access to deal analysis toolkit and AI underwriting tools

Leasing Commercial Spaces

Importance of detailed marketing materials

Create comprehensive listings with floor plans...

Key Takeaways:

Avoid Overpaying

Value in commercial real estate is based on income (NOI), not comparable sales

Always verify the actual trailing 12-month financials

Know the market's cap rate

Never buy on potential alone, pay for current earnings

Understand True Operating Expenses

Don't trust the broker's pro forma

Carefully check:

Actual property taxes

Deferred maintenance costs

Management expenses

Necessary reserves

Match Financing to Your Business Plan

Ensure loan terms align with...

Key Takeaways:

Commercial Real Estate Insights:

Big box retail spaces offer value-add opportunities

Most successful retail chains lease, not buy, their real estate

Demising large spaces requires careful analysis of walls, plumbing, HVAC, and layout

Investment Trends:

Current market is unpredictable

Leasing rates vary significantly

Some investors are aggressive, others are waiting on sidelines

Upcoming Opportunities:

30 Deals, 30 Days challenge (free commercial real estate education)

New educational platform for developers/investors launching soon

Mastermind event on...

Key Takeaways:

Affordable Housing Impact

Serves families making $22,000 to $80,000 annually

Provides housing for essential workers like servers, government employees

Goes beyond buildings to create community and support services

Development Philosophy

Focus on creating unique developments with local identity

Partner with nonprofits to provide resident services

Prioritize sustainability and community-centered design

Career Journey

Started in real estate through mentorship and hands-on learning

Founded Holiday Ventures to create more mission-driven housing developments

Raised initial capital through brand...

Key Takeaways:

Focus on Simple, Manageable Properties

Look for properties under $2 million

Choose assets with low operational complexity

Prioritize properties with stable, long-term tenants

Best Property Types for Beginners

Small multi-tenant retail centers

Office condos or medical suites

Flex industrial spaces

Single-tenant triple net properties

Critical Investment Criteria

Simplicity of operations

Manageable size

Tenant and lease stability

Market familiarity

Scalability potential

Rookie Traps to Avoid

...

Key Takeaways:

You can enter commercial real estate without large cash investments by solving specific problems for property owners.

Three core principles for entering commercial real estate:

Define a clear transformation statement

Package your unique value proposition

Know your monetization model from the start

The commercial real estate "flywheel" strategy:

Find a struggling asset

Solve the property's problems

Get compensated through fees or equity

Use the success as a track record for future deals

Types of prospects:<...

Key Takeaways:

CRE Central App Launch

New mobile app exclusively for mastermind members and course participants

Will centralize courses, events, and resources in one platform

Upcoming Education Platform

Launching in January 2026

University-style commercial real estate education

Majors in brokerage, investment, and development

Aims to be an affordable alternative to traditional college education

Raising Capital Strategies

Start building investor network before finding deals

Reach out to potential investors early

Create multiple "fishing lines" (personal brand, online...

Key Takeaways:

Public-Private Deal Risks

The public took all the financial downside while the private owner (Jeffrey Loria) gained all the upside

No accountability or performance clauses in the deal

Lack of transparency and no public vote

Financial Structural Problems

Revenue bonds backed by volatile tourism taxes

High-interest, long-term debt ($1.9 million bond projected to cost over $1 billion)

Principal payments don't start until 2026, extending debt to 2048

Real Estate Investment Lessons

Demand drives everything - the Marlins had a small fan...

Key Takeaways:

Abandoned buildings offer hidden investment opportunities that most investors overlook

Evaluate potential properties using a three-part framework:

Location-driven demand

Structure adaptability

Zoning and incentives

Steps to get started:

Understand construction costs

Research tenant demand

Learn to creatively reimagine building spaces

Profit potential comes from:

Buying properties at low square footage prices

Transforming them to create income-based value

Potentially generating six to seven-figure profits

Key mindset:

See potential...

Key Takeaways:

Passive Income Strategy:

Start with an active, high-value deal that forces appreciation

Use a 1031 exchange to roll gains into a passive, cash-flowing investment

Avoid getting stuck in low-return properties

Specific Example (Buena Vista Deal):

Bought land for $618,000

Rezoned from 11 to 63 units

Sold for $1.575 million

Used 1031 exchange to invest in a self-storage facility

Investment Approach:

Step 1: Take on an active deal

Step 2: Force appreciation and exit

Step 3: 1031 exchange into a...

Key Takeaways:

For new development projects, investors typically want to see a 20% or higher Internal Rate of Return (IRR).

An 8% return is considered too low for development projects, which are inherently risky.

Equity multiple is often a preferred return metric, with investors looking for around 2x equity multiple in less than five years.

When vetting contractors, it's crucial to:

Talk to other developers they've worked with

Inspect their job sites

Check their professionalism and documentation

Seller financing depends on:

Talk to...

Key Takeaways:

Deal Flow Framework (DEAL):

Discover: Uncover opportunities before they hit the market

Engage: Build relationships with brokers, owners, and key players

Activate: Create systems to track and follow up on leads

Leverage: Use your network and track record to scale

Three Main Reasons Investors Struggle to Find Deals:

Being passive instead of actively seeking opportunities

Weak broker relationships

Lack of consistent follow-up system

Commercial Real Estate Insights:

Best deals rarely appear on public listings

Key Takeaways:

Don't gamble in commercial real estate - have a clear strategy

Develop a Buy Box framework with 5 key steps:

- Investor Identity

- Asset Class Clarity

- Market Focus

- Financial Filters

- Operational Boundaries

Know exactly what you want before investing:

- Your investment goals

- Desired property type

- Target market

- Minimum financial returns

- Level of personal involvement

Benefits of a Buy Box:

...

Key Takeaways:

Creative Financing: Brandon leveraged seller financing and creative deal structures to grow his real estate portfolio, starting with house hacking in East Nashville.

Freedom Number Approach: He set a clear goal of $10,000 monthly cash flow to transition from tour managing to full-time real estate investing.

Partnerships and Delegation: After reading "Who Not How," Brandon learned to partner with the right people and delegate tasks instead of doing everything himself.

Family-First Business Design: He intentionally structures his business to prioritize family time, including not working weekends and setting clear boundaries.<...

Key Takeaways:

Residential real estate is a "second job" with low returns, while commercial real estate offers scalable, passive income

Commercial properties generate higher cash flow by leasing to multiple businesses under one roof, typically netting around $15,000 monthly

Commercial real estate allows investors to force appreciation by repositioning assets, changing tenant mix, and improving property layout

Professional commercial tenants are more reliable, focused on business growth, and less emotionally demanding compared to residential tenants

Success in commercial real estate requires learning specific skills like deal underwriting, building a specialized...

Key Takeaways:

Commercial Real Estate Corruption:

Bribery and corruption are prevalent in the industry

Common issues include:

Brokers taking backdoor payments

Sharing confidential information

Bribing politicians for zoning approvals

Contractors inflating project costs

Investment Advice:

Always get agreements in writing

Trust is crucial when selecting a broker

Understand market dynamics before analyzing deals

Get multiple bids for projects

Be cautious of potential conflicts of interest

Industry Insights:

...

Key Takeaways:

Passive Income Strategy: Wealthy investors use triple net leases to generate consistent monthly income from properties leased to national brands like CVS, Dollar General, and 7-Eleven.

Low Maintenance Investment: These properties require minimal management, as tenants cover all expenses including taxes, insurance, and maintenance.

Long-Term Benefits:

Predictable income with 10-20 year leases

Built-in rent increases

Significant tax advantages

Wealth preservation

Investment Characteristics:

Typically cost $1-3 million

6-8% annual cash return

Tenants are stable...

Key Takeaways:

Early Exposure: Jake's background in real estate started with his father, who was an investor and flipper, which inspired his career path.

Networking Strategy: He attended 8-10 networking events weekly and meticulously tracked contacts, believing "network is my net worth."

Persistence: Jake used cold calling extensively, making up to 400 calls a day to build his pipeline.

Specialization: He focused on 15-75 unit multifamily properties, primarily in the Murfreesboro market.

Mindset Shift: Transitioned from a transactional approach to being an investment sales advisor, which helped differentiate himself.

Key Takeaways:

Start Investing Early: Residential agents should begin investing in real estate to build cash flow and financial freedom, rather than spending money on luxury items.

Cash Flow is King: Focus on creating passive income that can cover your expenses and provide options in life.

Partnership Matters: Choose partners carefully and do thorough due diligence. A bad partnership can disrupt your peace of mind and potentially cost you money.

Commercial Real Estate Advantages: Commercial properties often have less drama, more stable tenants, and require less day-to-day management compared to residential...

Key Takeaways:

Flex Space Advantages:

More versatile than multi-family real estate

Allows for diverse tenant mix

Easier to lease smaller suites quickly

More logical and less emotional tenant interactions

Investment Strategy:

Buy properties that can be easily modified

Focus on value-add opportunities

Aim for full occupancy and market-rate rents

Target properties with flexible layout options

Financial Approach:

Invest in properties with potential for double-digit returns

Prefer 7% preferred return for investors

70/30 profit...

Key Takeaways:

Apartments are overcrowded, overpriced, and not the guaranteed path to financial freedom many believe.

Alternative investment strategies like self-storage, flex spaces, industrial outdoor storage, and triple net properties can offer:

More stable cash flow

Less management hassle

Lower tenant turnover

Potentially higher returns

Real investment success isn't about accumulating the most "doors" but finding the right assets that:

Generate consistent income

Require minimal day-to-day management

Provide flexibility and peace of mind

Successful investors like Ryan...

Key Takeaways:

Advice on leaving W2 job for real estate syndication:

Don't leave your W2 job too quickly

Start small and gradually build your portfolio

Fees from initial deals likely won't cover living expenses

Have a backup income source while growing your real estate business

Challenges of starting a syndication:

Raising capital is difficult

Initial deals may not generate significant income

Need to be prepared for 2-3 years of limited earnings

Requires careful deal selection and strategic planning

Key Takeaways:

Alec transitioned from residential to commercial real estate, focusing on industrial and flex space development.

His first commercial deal was a 54,000 sq ft industrial property in a tertiary market, purchased through creative financing with partners.

Raising capital is often the most challenging part of development, more so than the construction process itself.

Alec chose New Braunfels, Texas for development due to faster site plan approval times and favorable building regulations.

He focuses on building flex space under 12,000 sq ft to avoid expensive sprinkler system requirements.

...

Key Takeaways:

Economic Uncertainty: There are potential signs of a recession, with five major economic forces potentially suppressing US economic growth through 2025-2026.

Commercial Real Estate Outlook: The market is unpredictable, with potential both positive and negative impacts across different asset classes (retail, office, multifamily, industrial).

Investment Strategy Advice:

Don't make decisions based on fear

Look at investments with a long-term perspective (5+ year horizon)

Keep cold calling and networking

Focus on buying good assets

Business Approach: Treat commercial real estate as a professional...

Key Takeaways:

Creative Capital Matters More Than Cash

You don't need all the money upfront to invest in commercial real estate

Focus on controlling the deal and finding creative financing options

Explore strategies like seller financing, lines of credit, and investor partnerships

Financing Strategies

Consider 100% seller financing for commercial properties

Use lines of credit strategically if investment returns exceed interest rates

Partner with experienced investors to leverage their track record

Investment Goals

Aim for 18-22% internal rate of return<...

Key Takeaways:

Relationship Building

Maintain constant communication with property owners (quarterly or at least annually)

Reach out with market updates, recent deals, or just to check in

Prospecting Strategies

Lead with specific tenant requirements

Track potential tenants and market movements

Use AI tools like ChatGPT to analyze property data and narrow down prospects

Deal Flow Techniques

Build relationships across different market segments

Leverage tenant representation to create deal opportunities

Consider co-investing to add more value and understand...

Key Takeaways:

Create deals, don't just find them

Reputation compounds faster than capital

Chasing cash flow can keep you poor - focus on equity and value creation

Control is more valuable than ownership

One great relationship can change everything

The first deal is the hardest

Scale faster by focusing smaller (inch wide, mile deep)

Brokerage is the best entry point for beginners

If you're the smartest person in the room, you're in the wrong room

Build your brand now...

Key Takeaways:

Tailor your pitch to your audience:

Institutional investors want rigorous data and professional decks

Private investors are more relationship-driven and emotionally influenced

Focus on key investor motivations:

Stability (durability through economic cycles)

Passive growth (minimal management headaches)

Impact and legacy

Downside protection and risk mitigation

Pitch delivery tips:

Be comfortable and authentic

Don't read slides word-for-word

Understand your subject matter deeply

Have multiple exit strategies

Build trust before the...

Key Takeaways:

Contractor Selection Strategy:

Always be networking and meeting contractors before you need them

Not all contractors are skilled in every type of project (e.g., house builders aren't necessarily restaurant builders)

Look for contractors with specific experience in your project type

Contractor Engagement Approaches:

Design-Bid-Build: Fully design project first, then get contractor bids

Design-Build: Bring contractor in early to consult during design process

Each approach has pros and cons depending on project scale and budget

Networking Tips:

...

Key Takeaways:

Leverage Your Existing Network

Share what you do professionally

Have one-on-one conversations

Tell stories about successful clients

Ask for specific referrals

Hyper Local Farming

Focus on a manageable geographical area

Walk and know your target market

About 5% of properties may be interested in trading at any time

Door knocking, cold calling, and direct mail can be effective

Position Yourself as an Online Expert

Use platforms like LinkedIn, podcasts, blogs

Share valuable...

Key Takeaways:

Commercial Real Estate Investment Insights:

Returns vary based on risk and market conditions

Long-term real estate investing is more stable than short-term speculation

Look for risk-adjusted returns, not just raw percentage numbers

Current Projects:

Salt Ranch boutique hotel is near completion

Started construction on a 350-unit self-storage facility in Chattanooga

Restructuring his company with more back-office support

Investment Advice:

Real estate has historically appreciated 3-5% annually

Hard assets like real estate can hedge against inflation<...

Key Takeaways:

The $370K underwriting mistake that changed everything

How Marcus scaled from one car wash to a multi-property empire

Why strong banking relationships are a growth cheat code

The power of treating tenants like partners •

How he’s setting his kids up to run the family portfolio