Financial Freedom with Real Estate Investing

The vast majority of us get into multifamily investing because we are hungry for time freedom. We want the flexibility to spend time with our families or travel or go to the gym in the middle of the day if we so choose. But many of us lose sight of that original goal in the pursuit of financial freedom. Our focus on earning money translates to doing ALL of the work ourselves, and before long, we are caught in an unsustainable cycle—doing tasks like bookkeeping and writing investor reports that undervalue our time and pull us away from the work only we can do: finding deals and raising money. So, how do we calculate the value of our time and make informed decisions about what to delegate? How do we hit the reset button and return our focus to the time wealth that inspired us to pursue apartment building investing in the first place?

Mark Dolfini is the founder of Landlord Coach, a mentoring program and business course for landlords and property managers. He is also the author of The Time-Wealthy Investor, Your Real Estate Roadmap to Owning More, Working Less, and Creating the Life You Want. Mark is on a mission to help multifamily investors realize the value of their time and design an intentional business that affords them both financial freedom and time wealth.

Today, Mark joins me to discuss his early interest in the idea of owning real estate and his gradual accumulation of 92 rental properties. He shares the mistakes he made in trying to do all the work himself that led to his Jerry Maguire moment in 2008 when he lost $4.5M overnight and ended up in the hospital with double pneumonia. Mark describes the mindset shift that helped him transition from self-employed to business owner and the VIP System he designed to create a sustainable real estate venture. Listen in for Mark’s insight on the concepts of life output and time wealth—and learn how to determine what your time is worth and delegate accordingly!

Key Takeaways

Marks’s early interest in real estate

  • Asked for real estate for Christmas as boy
  • Bought 40 acres in AZ while in Marines

How Mark accumulated 92 rental properties

  • Bought 12 while attending Purdue
  • 30 when quit working as accountant ($6M)
  • Made every mistake, no systems in place
  • Doing all work ‘life was definition of hell’

Mark’s Jerry Maguire moment in 2008

  • Drop from $65K in rent revenue to $30K
  • Lost $4.5M in real estate overnight
  • Worked more, developed double-pneumonia

How Mark transitioned from self-employed to business owner

  • Intentional about setting up sustainable business
  • Only do tasks that demo highest, best use of time

Mark’s VIP system

  • Vision beyond making money
  • Infrastructure = framework
  • Process = rules of operation

The concept of life output

  • Ability to control calendar
  • Financial wealth as means to end

How to determine the value of your time

  • Calculate current hourly wage (including travel)
  • View as loss of $ when performing lesser tasks

Connect with Mark

Landlord Coach

Landlord Coach on Facebook

Mark on LinkedIn


The Time-Wealthy Investor: Your Real Estate Roadmap to Owning More, Working Less, and Creating the Life You Want by Mark B. Dolfini

The Judge: A Landlord’s Tale by Mark Dolfini

Financial Freedom with Real Estate Investing: The Blueprint to Quitting Your Job with Real Estate—Even Without Experience or Cash by Michael Blank

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

  • Download
  • Text “secretbook” to 44222

Michael’s Website

Michael on YouTube

Podcast Show Notes

There are five key phases in the multifamily investing process, and the property manager you hire plays a key role in nearly every stage. So, what should you look for in a property management company? And what KPIs can you use to assess the property manager’s performance?

Bryan Chavis is a thought-leader in the realm of multifamily property management and the bestselling author of Buy It, Rent It, Profit and The Landlord Entrepreneur. He is also the founder of The Landlord Property Management Academy, an online platform for real estate professionals and property management certification. Bryan was named one of the top 40 up-and-coming entrepreneurs under 40 by the Gulf Coast Business Review, and he is a sought-after speaker and consultant for some of the largest housing authorities in the US.

Today, Bryan sits down with me to share his journey, discussing the obstacles he has overcome and his unique approach to ‘embracing adversity.’ He walks us through the five phases of multifamily investment, discussing the current challenges around the acquisitions process and the fundamentals of the implementation stage. Bryan explains what to look for in a property management company and the Key Performance Indicators he reviews on a monthly basis. Listen in for Bryan’s insight on finding a property manager who is proactive and learn to relish the journey as a multifamily investor!

Key Takeaways

Bryan’s introduction to real estate

  • Job as leasing agent for free apartment
  • Learned from private, institutional investors

Bryan’s key takeaways as a property manager

  • Understanding of asset management, acquisitions
  • Real-life experience as operator

What inspired Bryan to branch out on his own

  • ‘Why not me?’
  • Experience in all facets of multifamily
  • Speaking career to develop business

The adversity Bryan had to overcome

  • High school diploma, lack of capital
  • Devastating brain tumor (no insurance)

Bryan’s approach to ‘embracing adversity’

  • Character-building opportunity
  • Share story to inspire others

Bryan’s 5 phases of a multifamily investment

  1. Acquisitions
  2. Implementation
  3. Stabilization
  4. Growth
  5. Exit strategy

The current challenges around acquisitions

  • Standoff between buyers and sellers
  • Wade through deals to find one that works

Bryan’s view of the implementation phase

  • Establish procedures, consistency
  • Software (e.g.: Buildium)

How to avoid mistakes during the acquisitions process

  • Build margin of error into underwriting
  • Focus on low cash multiple but high efficiency

What to look for in a property management company

  • User-friendly, intuitive software platform
  • Ability to manage every asset class
  • Management plan specific to property

The difference between a proactive and reactive property manager

  • Control income, expenses during stabilization
  • Software, training allows to manage as business

Bryan’s approach to overseeing a property manager

  • ‘Inspect what you expect’
  • Walk property on regular basis
  • Scrutinize KPIs monthly

Bryan’s Key Performance Indicators (KPIs)

  • Rent rolls, maintenance tickets/budget
  • P&Ls, delinquencies and turnover
  • Traffic and closings

Bryan’s current mission

  • Wake up and be appreciative
  • Relish journey, relationships

Connect with Bryan

Buy It Rent It Profit

Landlord Academy

Multifamily Facebook Group

Bryan on Facebook

Bryan on Twitter

Call 1-800-535-2476


Buy It, Rent It, Profit: Make Money as a Landlord in ANY Real Estate Market by Bryan M. Chavis

The Landlord Entrepreneur: Double Your Profits with Real Estate Property Management by Bryan M. Chavis


Michael’s Products

The Ultimate Guide to Apartment Building Investing

Michael’s Syndicated Deal Analyzer

Michael’s Deal Maker Mastermind

Financial Freedom Summit

Deal Desk

Deal Maker LIVE

Michael’s Coaching Program

Partner with Michael

Invest with Michael

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

Review the Podcast on iTunes

You don’t necessarily need an enormous multifamily portfolio to achieve financial freedom. It is possible to start small and replace your income with modest holdings of just 20 units!

Aaron Howell is a small multifamily investor with Black Lick Holdings, a real estate firm based in Crozet, Virginia. With a portfolio of 22 rental units, Aaron has replaced his income as a pharmacist and now works part-time because he WANTS to, not because he HAS to.

Today, Aaron joins me to share his accidental introduction to real estate and when he was finally inspired to develop a strategic plan. He describes the light bulb moment when he realized the income potential of a duplex versus a single-family property and how he fostered the confidence to pursue multifamily despite a lack of experience. Aaron walks us through his first several deals, explaining how he financed the most recent 6-unit through a partnership. Listen in for Aaron’s insight around building in daily habits to stay motivated and learn how he achieved financial freedom with a small portfolio!

Key Takeaways

Aaron’s introduction to real estate

  • Bought townhouse in 2006
  • Rented to cover mortgage after move

Aaron’s start in single family

  • Opportunities in Las Vegas
  • Desire to create passive income

What inspired Aaron to develop a strategic plan

  • Got married in 2015 and closed on first duplex
  • Realized upstairs rent covered mortgage
  • Heard Michael on podcast and took course

Why Aaron was confident in small multifamily investments

  • Same process with bank as single family
  • Did well in Vegas despite lack of experience
  • Solid team in place to support

How Aaron financed his first multifamily deals

  • Home equity line of credit
  • Relationship with local bank
  • Sold Vegas properties (1031)

Aaron’s take on partnerships vs. syndication

  • Pittsburgh property partnership among 4 investors
  • Syndication in future to control deal

Aaron’s transition to working part-time

  • Wants to work but doesn’t have to
  • Weekends, evenings free

Aaron’s real estate plans for the future

  • Scale up to larger properties
  • Raise money through conversations

Aaron’s insight around financial freedom

  • Shawshank Redemption moment
  • Sense of confusion

Aaron’s advice for aspiring multifamily investors

  • Build network
  • Get familiar with market

How Aaron stays motivated

  • Habit List app (e.g.: read 20 minutes, look at 15 listings)
  • ‘20 units’ on chalkboard in kitchen

Connect with Aaron

Aaron on BiggerPockets



Michael on the Joe Fairless Podcast




Habit List

Michael’s Products

The Ultimate Guide to Apartment Building Investing

Michael’s Syndicated Deal Analyzer

Michael’s Deal Maker Mastermind

Financial Freedom Summit

Deal Desk

Deal Maker LIVE

Michael’s Coaching Program

Partner with Michael

Invest with Michael

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

Review the Podcast on iTunes

Whether you are looking to become a multifamily syndicator or money raiser, it is difficult to get your foot in the door if you’ve never been involved in a deal. So, how do you build a resume without any experience or capital to speak of? The answer lies in partnerships with someone who’s done it before!

Danny Woodford is a Managing Partner at Mission Bay Investments, a multifamily investment firm with properties in the Mid-Atlantic, Southeast and Texas markets. Mission Bay is focused on value-add opportunities of 100-plus units, and the firm has closed on five deals of nearly 1K units to date. Prior to real estate, Danny served in the military, working to develop the space capabilities of the United States. He holds a master’s in real estate development from George Mason University.

Today, Danny joins me to explain what inspired him to retire from the military and pursue real estate. He walks us through his initial single family business model and the AHA moment that motivated his transition to multifamily. Danny offers the details of his first two multifamily deals in Richmond, Virginia, sharing the reasons why he continues to source deals despite the challenging market. Listen in for Danny’s insight around bringing a deal to a potential partner and learn how to build your multifamily resume by teaming up with someone who’s been there!

Key Takeaways

What inspired Danny’s shift from the military to real estate

  • No control over time
  • Long commute, missed family events

How Danny found the time to get educated in real estate

  • Designed plan with wife to replace income
  • Research during commute, nights and weekends

Danny’s initial business model

  • Build portfolio of single family rentals
  • Fix and flips to finance renovations

Why Danny made the transition to multifamily

  • Conversation with colleague at single family seminar
  • Multifamily offers more in terms of efficiency, scale
  • Financing more attractive (nonrecourse lending)

Danny’s first multifamily deal

  • 40-unit apartment building in Richmond
  • Found through broker relationship
  • Purchased for $1.1M (one investor)
  • Completed exterior, electrical work
  • Sold for $1.5M in 1031 exchange

Danny’s second multifamily deal

  • 98-unit purchased for $5.8M
  • Syndication raise of $10M
  • Rents $100 below market

Why Danny is finding deals despite a challenging market

  • Resume of five multifamily deals (two under contract)
  • Relationships with brokers, investors and lenders

The value of partnering as a money raiser

  • Brought into management team
  • Compensation for efforts, builds resume

Danny’s advice for aspiring multifamily investors

  • Bring capital or deal to table
  • Partner with experienced investor
  • Go straight to multifamily

How to bring a deal to a potential partner

  • Do homework on project (analysis, underwriting)
  • Establish relationship with seller/broker

What Danny is looking for in money-raising partners

  • Education and drive
  • Experience raising money

Connect with Danny

Mission Bay Investments

Call (661) 816-0335




Michael’s Products

The Ultimate Guide to Apartment Building Investing

Michael’s Syndicated Deal Analyzer

Michael’s Deal Maker Mastermind

Financial Freedom Summit

Deal Desk

Deal Maker LIVE

Michael’s Coaching Program

Partner with Michael

Invest with Michael

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

Review the Podcast on iTunes

The attitude toward cannabis has shifted: 64% of Americans support the legalization of marijuana, 93% support medical consumption, and the drug is legal in nine states plus Washington, DC. By 2028, the cannabis space is projected to be a $60B industry. So, what does that mean for us as real estate investors? How can we take advantage of the need for property to grow, manufacture and sell cannabis products?

Leslie Plettner is the director of BaseCanna, a team of cannabis, legal, finance and real estate experts who provide the funding, infrastructure and property for cannabis entrepreneurs. Leslie is a long-time entrepreneur with extensive experience in real estate. She has developed and managed more than 500 units, including a mix of warehouse, multifamily and retail properties. Three years ago, Leslie anticipated the emergence of the cannabis industry and recognized its need for cannabis-friendly landlords, and the idea for BaseCanna was born.

Today, Leslie joins me to describe BaseCanna’s work in developing an ecosystem of cannabis operators and the market opportunity in the space for real estate developers. She shares the risks of cannabis real estate, both perceived and real, and explains how BaseCanna makes decisions around who to work with. Listen in for Leslie’s insight on the appreciation of a property once it’s licensed for cannabis and learn why now is the right time to get into cannabis real estate!

Key Takeaways

The mission of BaseCanna

  • Anchor development of cannabis ecosystem with real estate
  • Support operator-members with compliance, legal issues, accounting & insurance

Leslie’s background as an entrepreneur

  • Designed, transformed underperforming schools
  • Shift to real estate when started family

BaseCanna’s current work

  • Creating vertically integrated ecosystem (seed to sale)
  • Vet municipalities, real estate and operators

The market opportunity in cannabis real estate

  • Fastest growing since broadband internet
  • Huge expansion in therapeutic consumption
  • Shift in attitude (93% support medical use)

The myths around owning cannabis real estate

  • Pothead tenants, criminal activity
  • Civil asset forfeiture (landlords protected)

The real risks around owning cannabis real estate

  • Must be in municipality regulated for cannabis
  • Ensure tenant has license, pays taxes
  • Property must be zoned for cannabis
  • Be careful of green rush illusion
  • OSHA fines, federal prohibition

How BaseCanna makes decisions around who to work with

  • Right license for right product in right market
  • Pay attention to overall market trends (i.e.: demand for manufactured products)

The appreciation on a property once it’s licensed for cannabis

  • BaseCanna paid $1.8M for two warehouses
  • Offers for $4.5M once repositioned

The permitting process for cannabis real estate

  • Very involved, 200-page applications (SOP, demo capacity)
  • Lawyers charge $40K to $75K to guide through process

Leslie’s advice on having an exit strategy

  • First opportunity = create operational campus
  • Immediate exit available once licensing in place

Leslie’s insight on getting in the cannabis game now

  • Institutional money will come in with end of federal prohibition
  • Real estate premiums will fall as more municipalities regulate

Connect with Leslie



UCLA Study on Crime & Dispensaries


The Rohrabacher-Blumenauer Amendment

Michael’s Products

The Ultimate Guide to Apartment Building Investing

Michael’s Syndicated Deal Analyzer

Michael’s Deal Maker Mastermind

Financial Freedom Summit

Deal Desk

Deal Maker LIVE

Michael’s Coaching Program

Partner with Michael

Invest with Michael

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

Review the Podcast on iTunes

Anna Simpson’s philosophy is that you don’t make money in your comfort zone. Once she has achieved a goal, Anna finds a way to push her limits and look forward to the next. And when things start to get difficult, that’s when Ana knows she needs to keep digging: She’s getting closer to the gold.

Anna is a full-time accredited multifamily investor and deal sponsor with experience in property valuation, acquisition, rehabilitation, leasing and asset management. She got her start investing in single family buy and holds before making the decision to transition to multifamily as a passive investor. Anna personally invested in 1,300 multifamily units as an equity partner and key principal before she was ready for the next challenge of becoming a managing partner. Today, Anna has completed two multifamily deals: a 70-unit syndication and a 76-unit 1031 exchange.

Today, Anna sits down with me to share her decision to work ON the business rather than IN it by making the shift to multifamily. She explains how she leveraged her role as a passive investor to learn the fundamentals of syndication and the key challenge she faced in landing her first deal as managing partner. Anna offers insight around the value of persistence and breaking big goals down into smaller chunks. Listen in for Anna’s advice on pushing beyond your perceived limits and learn why she believes that while knowledge is important, true power lies in consistent ACTION.

Key Takeaways

How Anna got involved with real estate

  • Friends active in single family group
  • ‘Success breeds success’

Anna’s initial investment strategy

  • Single family buy and hold rentals
  • Successful but difficult to scale

Anna’s shift to multifamily

  • Working on New Year’s Eve
  • Made decision to work ON vs. IN
  • Got involved as passive investor

What Ana learned as a passive investor

  • How to communicate with vendors, investors
  • How to supervise rehab
  • How to design, implement plan

Anna’s first multifamily deal

  • Found off-market through relationships
  • Syndicated 70-unit deal (23 passive investors)
  • $4M purchase price, $1.4M raise in one day

Anna’s approach to goal-setting

  • Identify where you are and where you want to be
  • Break down into smaller goals (e.g.: one LOI/week)
  • Work backwards and assess regularly

Anna’s key challenge in landing her first multifamily deal

  • Overcame lack of track record with team
  • Experience as investor in 1,300 doors

How the Law of the First Deal impacted Anna

  • Second deal under contract 2 months after first
  • Off-market deal through broker

Anna’s insight on the value of persistence

  • Difficult times mean you’re getting closer
  • Accept setbacks as part of journey
  • Move forward to build reputation, respect

What Anna would do differently given the opportunity

  • Start earlier with apartments
  • ‘You don’t know what you don’t know’

Anna’s advice for aspiring real estate investors

  • Learn through podcasts, groups, etc.
  • Treat as business not hobby
  • Consistent ACTION = POWER
  • Work on mindset constantly
  • Leverage passion on down days

How Anna navigates the down days

  • Surround with supportive, optimistic people

Connect with Anna

Anna’s Website


Rich Dad Poor Dad: What the Rich Teach Their Kids About Money That the Poor and Middle Class Do Not by Robert T. Kiyosaki

Michael’s Deal Maker Mastermind

Deal Desk

Deal Maker LIVE

Michael’s Coaching Program

Michael’s Products

Michael’s Syndicated Deal Analyzer

Michael’s Deal Maker Mastermind

Financial Freedom Summit

Partner with Michael

Invest with Michael

Michael’s Course

Free eBook: The Secret to Raising Money to Buy Your First Apartment Building

Review the Podcast on iTunes

Podcast Show Notes

Review the Podcast on iTunes