Mac Shelton is the co-founder of Sweetbay Capital, a real estate private equity firm focused on value-add multifamily investments in Virginia and the Carolinas. With a background in private equity and mezzanine lending, Mac blends institutional financial experience with a data-driven approach to real estate. Since 2021, he and his team have built a portfolio of over 340 units, concentrating on under-the-radar markets like Roanoke, VA, where rent growth consistently outpaces new supply.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Rent growth—not population growth—is the key driver of returns

• Markets with less outside capital often outperform due to better entry pricing and lower volatility

• Renovation premiums are often overestimated—test before scaling your plan

• Conservative exit underwriting should account for the next buyer's view, not just your own

• Transparency with investors builds trust and fuels long-term partnerships

Topics

Why Sweetbay Focuses on Smaller Markets

• Smaller markets like Roanoke and Columbia are producing higher rent growth with lower acquisition costs

• Mac compares tertiary markets to places like Raleigh in the early 2000s—under the radar but primed for stable returns

• Oversupply in "hot" metros like Raleigh and Charlotte is driving rents down, while less popular markets remain steady

Data Over Hype: What Drives Rent Growth

• Rent growth is more important than population growth and is driven by renter population relative to new supply

• Mac shares an analysis comparing Roanoke to Raleigh, Charlotte, and Greenville—showing similar or better rent performance with lower price per door

Why Lease Trade-Outs and Renewals Matter

• Lease trade-outs measure organic rent growth, but renewals give even clearer insight into demand

• Renewals at 3–4% growth without renovations are often a better gauge than turnover metrics

Exit Assumptions: Thinking Like the Next Buyer

• Every acquisition includes a re-underwrite from the future buyer's perspective

• Mac shares how he checks cap rate assumptions against current comps and validates price-per-door benchmarks

Transitioning from Private Equity to Real Estate

• Mac started his career in private equity and gradually began acquiring rentals with his bonus income

• His first syndication scaled a student rental model he'd already executed personally

Investor Communication and Building Trust

• Sweetbay Capital emphasizes detailed offering memorandums with full fee transparency and CapEx justifications

• Quarterly reports compare actuals vs original projections—no adjusted budgets or post-hoc explanations

Advice for New Syndicators

• Don't start syndicating without doing your own deals first—prove the model with your money

• Sweetbay's first deal had no promote, just a 3% acquisition fee, to reduce friction and earn investor trust

• The best way to grow capital is to return it and reinvest with a strong track record

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Mac up for success: Skipping early rent tests on a renovation project led to budget overruns—he learned the value of testing rent potential before scaling upgrades.

Digital or mobile resource: LandGlide – a $100/year app that offers a consolidated GIS view to quickly check property ownership and transaction history.

Book recommendation: Best Ever Apartment Syndication Book by Joe Fairless – a foundational guide Mac used to build the blueprint for Sweetbay.

Daily habit: Morning exercise—whether running, walking the dog, or hitting the gym—centers Mac and sets the tone for a productive day.

#1 insight for finding great markets: Ignore hype. Focus on fundamentals like rent-to-price ratios, supply dynamics, and how picked-over the market really is.

Favorite restaurant in Raleigh, NC: For casual: MoJoe's Burger Joint. For upscale: Stanbury.

Next Steps

• Connect with Mac on LinkedIn

• Visit sweetbay-capital.com to learn more about their deals and investor resources

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

Natalie Cloutier is a French-Canadian real estate investor who, alongside her husband, has spent over a decade building a successful build-to-rent business in Canada. With a background in architectural technology, Natalie began her journey by constructing her first home at the age of 19 using a sweat-equity loan, transforming a family "secret" into a powerful investment model. Today, she and her husband have built 53 units from the ground up, acquired and renovated four additional properties, and automated their business to support long-term growth. Her approach centers on risk-aware development, ADU maximization, and creative strategies to unlock housing value. She is also the author of The Build to Rent Strategy and co-founder of The New Build Couple.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Why building your own home with sweat equity can kickstart your investing journey

• The build-rent-refinance-repeat model Natalie uses instead of traditional BRRRR

• How legislation like Bill 23 unlocked value via ADUs

• The risks to watch for when analyzing land deals

• Why burnout forced her to scale—and how hiring a team changed her business

Topics

From Architecture School to First Build

• How Natalie and her husband started by building their own house at 19

• The sweat-equity loan that replaced a traditional down payment

• Living through construction while house-hacking their basement unit

Scaling with Confidence

• Transitioning from guided help to self-led builds

• Building nights and weekends while working 40-hour weeks

• How an employee learned their model and replicated it himself

Why Build-to-Rent Made Sense

• Existing properties in Ontario didn't pencil out

• Build-to-rent as a better alternative to BRRRR for their market

• The shift from slow beginnings to full-time real estate

Shifting Strategies Through Market Changes

• The effects of COVID, inflation, and interest rates

• Navigating legislative battles with municipalities

• Taking a break to reassess in the face of red tape

Due Diligence in Development

• Natalie's master checklist before buying land

• Zoning, sewer, easements, internet access, and environmental tests

• The consequences of skipping steps (like a $30k surprise for internet)

How ADUs Became a Game Changer

• Leveraging Ontario's Bill 23 to turn a duplex into a triplex

• Avoiding six-figure development fees by using ADU classifications

• Applying the ADU model to create sixplexes with cost savings

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Natalie up for success: Burning out from doing too much herself, led to hiring a team and building better systems.

Digital or mobile resource: Buildium, for managing tenant communication and operations, even with just a few units.

Book recommendation: Secrets of the Canadian Real Estate Cycle by Don Campbell, great for understanding market timing and cycles.

Daily habit: Running or walking: movement helps her reset and stay grounded.

#1 insight for real estate investors: Do your due diligence. This is not a risk-free strategy, so run the numbers and know what you're getting into.

Favorite restaurant in Mont-Tremblant, Quebec: Socal Kitchen.

Next Steps

• Connect with Natalie at thenewbuildcouple.com

• Follow her on Instagram to see project videos and updates

• Grab a copy of her book: The Build to Rent Strategy

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

Vitaliy Gnezdilov is the co-founder of Raise Ready Systems, a capital-raising platform helping real estate operators attract six- and seven-figure checks through paid social campaigns. With a background in user experience design, Vitaliy blends creative branding with performance marketing to help sponsors scale beyond friends and family capital. He has raised over $40M alongside strategic partners and formerly worked at CrowdStreet to streamline investor acquisition and conversion at an enterprise level.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Social media can drive serious capital—but only if you build trust, credibility, and speed into your funnel.

• "Speed to lead" is the difference between a committed investor and a missed opportunity.

• Avoid pitching too early—use the first call to understand investor goals and qualify the fit.

• Human touchpoints (real calls, manual follow-up) outperform automation when raising large checks.

• Sophisticated investors do respond to ads—if you tailor your messaging and sales process to their needs.

Topics

From UX Design to Real Estate Capital

• Vitaliy began his career in software and UX before partnering with a high school friend in advertising.

• Together, they leveraged design and paid traffic to raise capital in exchange for GP equity.

• Worked with sponsors across multifamily, mobile home parks, and ATMs—raising $40M+.

Building Raise Ready Systems

• Created a framework to generate investor conversations using paid ads and optimized funnels.

• Emphasizes "speed to lead" and relationship-building, not just lead generation.

• Most clients aim to raise $1M/month per investor relations rep using his system.

What Actually Works in Paid Campaigns

• 15–20 ad hooks are tested at launch; funnel must earn attention seconds at a time.

• Webinar funnels often fail due to lack of contextual awareness—must match platform behavior.

• Content and UX must be laser-targeted; the platform algorithm does the rest.

Human Touch vs. Over-Automation

• Raise Ready added an appointment-setting team that calls leads within 5 minutes.

• Human contact builds credibility before handing leads to IR teams.

• Created diligence packets and follow-up sequences to support investor conversion.

Common Mistakes Operators Make

• Lack of sales process is the biggest bottleneck—not lead volume.

• Founders often pitch too early; better to listen, qualify, and align investment opportunity.

• Raising from strangers is a different game than friends and family—adjust your approach.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Vitaliy up for success: Generating leads without a solid sales process led to client struggles—so they built internal appointment-setting and partnered with a top IR pro raising $1.5M/week.

Digital or mobile resource: RaiseReadySystems.com — explore the call funnel firsthand and browse in-depth insights on their blog.

Book recommendation: Buy Back Your Time by Dan Martell — a playbook for reclaiming your time and scaling your business through team leverage.

Daily habit: Praying each morning—"Throne before phone"—to center himself before opening the laptop.

#1 insight for raising capital: Speed to lead. But more importantly—don't pitch right away. Listen, qualify, and match your offer to investor needs.

Favorite restaurant in Minneapolis, MN: Khâluna.

Next Steps

• Connect with Vitaliy at RaiseReadySystems.com

• Explore their sales funnel strategy and blog resources

• Reach out to see if Raise Ready is a fit for your capital-raising goals

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

Catrina Craft is a CPA, tax strategist, and real estate investor with over 20 years of experience in applying the tax code to maximize wealth for investors and entrepreneurs. As the founder of Craft CFO Advisory Services, she supports real estate professionals, creative agencies, and business owners with proactive planning to reduce tax obligations and build long-term wealth. A frequent speaker and educator, Catrina brings a unique blend of compliance, strategy, and investment knowledge—helping her clients go beyond tax preparation and into true financial empowerment.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

Key Takeaways

• Start tax planning early—waiting until tax season puts you in reactive mode

• Don't structure appreciating assets in a C corp—it can lead to unnecessary tax penalties

• Asset protection is more than just forming an LLC; structure and exposure matter

• A tax strategist is proactive—meeting regularly and guiding decisions throughout the year

• The IRS rewards those who build and invest—use the code to your advantage

Topics

1. From Debt to Wealth Building

• Catrina lost 80% of her income when a major client left and found herself $100K in debt

• This challenge drove her to learn real estate investing and the tax strategies behind wealth building

• Paid off her debt in 2 years while building a rental portfolio

2. The CPA vs. Tax Strategist

• CPAs focus on compliance and reporting what already happened

• Tax strategists plan proactively to reduce your tax bill before decisions are made

• Working with a strategist who knows your industry—especially real estate—is critical

3. Avoiding Common Structure Mistakes

• Many investors set up LLCs without understanding tax treatment options

• Holding real estate in a C corp is a costly and often irreversible mistake

• Asset protection includes entity structure, insurance, and understanding exposure risk

4. Planning Beats Panic

• Most deductions and deferrals (like cost segregation and 1031s) require advance planning

• Catrina meets monthly or quarterly with clients to stay ahead of key decisions

• Tax planning should start at the beginning of the year—not at filing time

5. Questions to Vet a Tax Professional

• Ask about their industry experience and how often they meet with clients

• Determine whether they offer strategy or just compliance services

• Ensure they understand your specific investing model (e.g. syndication vs. flipping)

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Catrina up for success: Losing 80% of her income and going into debt forced her to learn real estate and rebuild—leading to lasting financial independence.

Digital or mobile resource: MileIQ — tracks mileage automatically for real estate and business-related driving.

Book recommendation: Tax-Free Wealth by Tom Wheelwright — foundational insights on using the tax code to your advantage.

Daily habit: Morning gratitude, sunlight, a walk, and 30 minutes of educational podcast listening to stay clear and motivated.

#1 insight for the best tax strategy: Hire a tax strategist—not just a tax preparer.

Favorite restaurant in Dallas, TX: Houston's or Hillside.

Next Steps

• Access Catrina's free tax planning resources.

• Connect with her through her LinkedIn Page.

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you don't miss an episode.

Jon Weiskopf is the Founder and CEO of Blue Eyed Capital, a purpose-driven investment firm focused on helping people of color invest in high-performing real estate that delivers both financial returns and meaningful impact. After a successful engineering career that included designing Apple's flagship retail stores around the world, Jon left corporate life to pursue a more meaningful mission—one grounded in sustainability, social responsibility, and leaving a better world for his children. His impact-focused approach to multifamily investing prioritizes operational efficiency, environmental upgrades, and tenant well-being as pathways to long-term success.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

• Real estate impact investing is not charity—it's smart, sustainable business

• Operational efficiency matters more than rent growth for long-term value

• Utility cost trends are critical indicators of property performance risk

• Personal alignment with your investing mission prevents burnout and increases longevity

• Finding properties close to home can reduce risk and improve responsiveness

• Capital access and relationship-building are essential for resilience in tough markets

From Apple to Apartment Investing

• Jon's career began in engineering, including 10 years leading Apple's retail development globally

• A burnout and desire to spend more time with family pushed him to rethink his priorities

• After attending a real estate event, he realized his background in construction and systems was an untapped advantage

Finding Purpose in Real Estate

• Named after his wife and children, Blue Eyed Capital was born from a desire to create legacy and impact

• Jon's "why" includes modeling values for his kids and using his skills to improve the world

• Leaving Apple and taking a three-month leave of absence gave him clarity and relief from corporate stress

Why Impact Investing Is Smart Business

• Jon focuses on improving underperforming Class C properties with outdated systems

• Instead of relying on rent increases, he drives returns through sustainability upgrades and energy efficiency

• Better-performing systems (HVAC, lighting, etc.) lead to tenant stability, lower expenses, and long-term ROI

What Most Investors Get Wrong

• Many operators don't understand the compounding effects of rising utility costs

• Passing on utility bills to tenants only works until affordability breaks down

• Energy-efficient upgrades generate increasing savings year over year—unlike cosmetic renovations

Choosing the Right Properties

• Looks for good bones: buildings that are structurally sound but need systems updates

• Willing to walk away from deals if fundamentals (e.g., plumbing) don't check out

• Proximity to home has become increasingly important for asset management responsiveness

Capital Raising and Private Lending

• Jon warns new operators not to underestimate the difficulty of raising capital

• Missed investor commitments and slow funding timelines require backup plans

• He's built a parallel business in private lending to create consistent cash flow between deals

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Failure that set Jon up for success: A high-stakes Apple project in San Francisco failed publicly at launch—but it taught Jon the value of resilience, preparation, and systems under pressure.

Digital or mobile resource: FRED – the Federal Reserve's data portal. Jon uses it to track trends like auto loan defaults and consumer credit that signal housing demand and risk.

Book recommendation: It Takes What It Takes by Trevor Moawad.

Daily habit: Wakes up at 3:30 a.m. every day to work out—starting with physical discipline to focus and own his day.

#1 insight for investing in impact properties: Purpose matters. If your plan is aligned with serving a community's needs—not just maximizing rent—you'll build a more stable, lasting business.

• Follow Jon on LinkedIn

• Check out Blue Eyed Capital's website.

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

Justin Brennan is a third-generation real estate investor and the founder of Brennan Polley Capital and Multifamily Schooled. After his family experienced a $60 million bankruptcy during the 2008 financial crisis, Justin rebuilt from scratch—growing a $185 million apartment portfolio across 1,100+ units in multiple states. Today, he's a leader in multifamily education and mentorship, helping others build wealth through cash-flowing assets, investor relationships, and a resilient mindset.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

• Use sweat equity to partner with others who bring capital—start with what you have

• Real estate offers generational wealth, but over-leveraging can wipe it all out

• Begin with a single unit if needed, but learn to scale fast using other people's money

• Community, discipline, and market knowledge are critical for out-of-state investing

• Opportunities don't knock—you create them and act when the door opens

Rebuilding After a Family Bankruptcy

• Justin's father built and lost a $60M portfolio during the 2008 crash

• Learned hard lessons early: never over-leverage and always prioritize cash flow

• Decided to restart in 2010 with a $100K condo—and a long-term mindset

From Small Starts to Major Scaling

• Bought duplexes and fourplexes before realizing the power of OPM

• Partnered with a friend in tech to launch Brennan Polley Capital

• First major deal: 27 units in Kansas City, raised $800K with just $30K out of pocket

• Now owns/control 40% of a $200M portfolio—vs. 100% of $3.5M before

The Power of Community and Conferences

• A Tom Ferry conference helped shift his mindset around raising capital

• Later attended a Boston syndication event, which gave him clarity and confidence

• Losing his sister in 2018 made him take bigger action—he chose not to live with regret

Investing Out-of-State with Confidence

• Recommends building your team before chasing deals: brokers, PMs, contractors, lenders

• Emphasizes importance of in-market relationships and pre-market deal access

• Uses security cameras to remotely monitor properties in real-time

• Invests only within 25–30 miles of top 100 MSAs for strong bank financing and tenant demand

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Failure that set Justin up for success: Walking away from a $33M deal after already investing $800K in due diligence. It hurt—but protected investors and built trust, leading to a more profitable deal soon after.

Digital or mobile resource: Crexi.com — not for deals, but to identify the top local brokers controlling inventory in a market.

Book recommendation: The Power of One More by Ed Mylett and Atomic Habits by James Clear.

Daily habit: Detailed morning routine that ends with a spoken "prayer letter" in the present tense. Uses the ThinkUp app to reinforce affirmations and stay focused on vision.

#1 insight for scaling a multifamily portfolio: "Never ask for money. Offer opportunity." Build trust, show results, and use a clear system for raising and managing capital.

Favorite restaurant in San Diego, CA: George's at the Cove.

• Subscribe to Justin's YouTube channel.

• Learn more about his program at multifamilyschooled.com

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

Nic Espanet is the founder of Flex Equity Group and host of the Flex Forward Podcast. After two decades as a physical therapist, Nic transitioned into real estate—starting with passive investments before becoming a lead general partner. He's now led eight out of ten multifamily deals across Texas, with a focus on operational systems, investor communication, and market strategy. Through his podcast and syndication work, he helps others build freedom through clarity, consistency, and resilience.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

• Start as a passive investor to learn best practices and build trust.

• Your first GP deal might require sacrificing equity to gain credibility.

• Raising capital today is about thoughtful follow-up, not just email blasts.

• Real estate's control and tangibility make it more appealing than stocks.

• Take fast action with underperforming property managers—delay can cost you.

From Healthcare to Real Estate

• Nic spent 20+ years in physical therapy before pivoting to real estate.

• Originally planned to invest in single-family homes before discovering multifamily.

• His first steps were as a passive LP, which taught him how great GPs operate.

The GP Transition

• Joined a Dallas real estate network to meet experienced sponsors.

• Partnered with a seasoned operator for his first deal and earned credibility through effort.

• Built his own investor systems based on what he appreciated as an LP.

Capital Raising in Today's Market

• Early deals filled in 2–3 days. Now it often takes weeks of phone calls and reminders.

• Uses GoHighLevel CRM to track interest, follow-ups, and conversations.

• Avoids texting new investors due to new legislation (SB140 in Texas).

Lessons From the Field

• During COVID, personally took over a failing asset and drove occupancy from 70% to 90%.

• Now focuses on Texas secondary markets with population growth and minimal new supply.

• Attributes success to consistent communication, team alignment, and market adaptability.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Failure that set Nic up for success: Waiting too long to fire a failing property management company. That experience now shapes how fast he acts when performance slips.

Digital or mobile resource: GoHighLevel CRM. It tracks soft commits, investor contact, and follow-up history in one place.

Book recommendation: Rich Dad Poor Dad by Robert Kiyosaki.

Daily habit: Early morning workouts with friends. It builds discipline, energy, and consistency.

#1 insight for scaling a multifamily portfolio: Find and surround yourself with a like-minded community of investors and mentors. Growth comes from relationships.

Favorite restaurant in Fort Worth, TX: Joe T. Garcia's.

• Visit flexequitygroup.com to learn more or schedule a call

• Listen to the Flex Forward Podcast for stories on reinvention and real estate

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

Kolaiah "Fuzzy" Jardine is a real estate developer, author, and co-founder of Hui Mastermind, a Hawaii-based community focused on empowering Native Hawaiians to build generational wealth. His journey took him from serving time in federal prison to creating a multimillion-dollar real estate portfolio and developing affordable housing for local families. As the author of Priced Out of Paradise, Fuzzy is on a mission to teach others how to invest "the Pono way"—with integrity, community, and purpose.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

• Fuzzy's transformation from prison to property developer shows the power of mindset and purpose.

• "The crab in a bucket" mentality, surrounding yourself with the wrong people, keeps you stuck.

• Taking bold, decisive action (even when broke) can change your trajectory.

• Investing education is priceless when you're ready to implement it.

• "The Pono Way" means people before profit—help others first, and wealth follows.

From Prison to Property Developer

• Fuzzy grew up in Oahu's multigenerational households, surrounded by love but also by poverty and addiction.

• After a prison sentence for drug-related charges, he discovered real estate through a white-collar inmate who taught classes on investing.

• Determined to change his life, Fuzzy came out of prison with a new mindset and a mission.

Finding Purpose and Building Mindset

• Initial jobs included window washing, surfing instruction, and valet parking—three jobs just to survive in Hawaii.

• Realized hard work alone wasn't enough; financial education was key.

• Discovered Rich Dad Poor Dad and began pursuing real estate investing as a way to create generational wealth.

The Turning Point: Fortune Builders

• While preparing to become a pilot, he heard a radio ad for a real estate training event and pivoted immediately.

• Borrowed $20K through a native Hawaiian loan and maxed out credit cards to join the program.

• His conviction came from being "sick and tired of working three jobs" and seeing his parents face foreclosure.

• Worked for free to gain hands-on experience and eventually became the go-to construction and development partner for other investors.

Building Affordable Homes and a Legacy

• Now leading 60+ projects focused on affordable housing on Hawaii's Big Island.

• Emphasizes integrity and "The Pono Way": helping families in distress before thinking of profits.

• Sees real estate as a means to restore opportunity for locals priced out of their own communities.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Failure that set Kolaiah up for success: Going to prison—being forced to reevaluate his life gave him clarity and purpose.

Digital or mobile resource: TruePeopleSearch.com. Great for finding owners of distressed properties to connect directly.

Book recommendation: Rich Dad Poor Dad by Robert Kiyosaki.

Daily habit: Prayer, expressing gratitude daily for where he is and the opportunities ahead.

#1 insight for building generational wealth: Dial in your "why." Once you know it, nothing can stop you from achieving success.

Favorite restaurant in Honolulu, HI: Zippy's.

• Get Fuzzy's book Priced Out of Paradise on Amazon.com

• Visit fuzzyjardine.com to learn about his projects and mentorship opportunities

• Follow him on Instagram for real estate education and community impact stories

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

In this week's solo episode, John Casmon steps away from guest interviews to share hard-earned lessons from his own investing journey. After returning to Chicago to speak at the Chicago Multifamily Club—a group he co-founded years ago—John reflects on the recurring questions he heard from investors eager to scale. Drawing on his personal experience building a portfolio from the ground up, he outlines the four pillars that every multifamily investor needs to master: clarity, relationships, process, and resilience.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

• Clarity creates direction—understand your "why" before chasing numbers or vanity metrics.

• Building relationships ("Who not How") is the key to growth—find mentors, partners, and communities.

• Follow a proven process instead of trying to reinvent the wheel.

• Resilience and resourcefulness matter more than experience—problems are inevitable but solvable.

• Scaling isn't about doing more work—it's about building the right team to achieve freedom.

The Chicago Multifamily Club Origin Story

• John co-founded the club in 2015 after attending too many unproductive meetups.

• Wanted to create an event that truly helped investors learn how to scale portfolios.

• Returning to speak at the same event years later was a full-circle moment of growth.

1. Get Clarity

• Understand why you want financial freedom, not just arbitrary goals like "100 doors."

• Real success comes from knowing what your investments are solving for—security, time, or impact.

• Clarity fuels motivation when challenges arise.

2. Identify Your "Who's"

• Networking consistency led John to relationships that shaped his trajectory.

• Relationships create shortcuts that experience alone cannot.

3. Follow a Proven Process

• Instead of guessing, John invested in mentorship to learn syndication and scale faster.

• First syndication: a 192-unit deal in San Antonio with partners from his coaching network.

• Proven processes eliminate guesswork and create predictable results.

4. Be Resilient and Resourceful

• Real estate is full of surprises: contractors stealing, investors asking tough questions, and deals going sideways.

• Resourcefulness—not resources—separates those who thrive from those who quit.

• Learn from setbacks and keep moving forward.

📢 Announcement: Learn about our Apartment Investing Mastermind here.

• Join John's investor community at casmoncapital.com

• Learn more about coaching and the Apartment Investing Mastermind at casmoncapital.com/coaching

Thank you for joining us for another great episode! If you're enjoying the show, please LEAVE A RATING OR REVIEW, and be sure to hit that subscribe button so you do not miss an episode.

Derek Dombeck is a seasoned real estate investor, national speaker, and international bestselling author who has navigated the ups and downs of real estate since 2003. Known for his expertise in creative deal structuring, private lending, and relationship-based investing, Derek has completed thousands of transactions while helping investors gain control over their financial futures. Today, he leads Generational Wealth, where he teaches others how to build lasting legacies through intentional business and personal vision.

Make sure to download our free guide, 7 Questions Every Passive Investor Should Ask, here.

• Learn to operate without banks by mastering creative deal structures and private lending.

• Building relationships—not relying on institutions—provides flexibility and resilience in any market.

• Investors must prioritize communication and integrity to maintain trust with lenders and partners.

• Success is rooted in having a clear vision for life first, and building business strategies around that.

• Control and freedom come from understanding "why" you want wealth, not just "how" to achieve it.

From Losing Everything to Creative Control

• Derek started in the early 2000s with bank financing but lost nearly everything in the 2008 crash.

• Learned to rebuild through creative financing and raising private capital instead of relying on institutions.

• Founded a private lending business averaging 20–25 loans per month, lending over $3 million monthly.

Why Relationships Beat Banks

• Institutional lending is transactional—private lending is relational.

• Investors who communicate transparently with private lenders can work through tough times and maintain trust.

• Reputation and reliability are worth more than a few basis points in interest savings.

Raising Private Capital

• Raised over $25 million by building genuine connections and paying investors before himself.

• Early mistake: not developing a network soon enough.

• Now teaches investors to focus on building long-term trust and a solid track record.

Creating a Vision-Led Life

• Entrepreneurs often trade a 9-to-5 job for a "5-to-9" grind—without defining what they actually want.

• Derek emphasizes creating a written life vision first, then building a business to support it.

• The question isn't how much money you want, but why you want it—and how it supports the life you envision.

Rethinking Goals and Ownership

• Many chase status symbols (like beach houses or luxury cars) without questioning their purpose.

• Derek explains how experiences can be enjoyed today without waiting decades—like renting a dream home instead of owning it.

• True wealth is freedom to live intentionally, not accumulation of "stuff."

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Failure that set Derek up for success: Not building a network early in his career—learning that relationships are the foundation of longevity.

Digital or mobile resource: ChatGPT and GoHighLevel CRM, used together to automate lead management and client communication.

Book recommendation: Pitch Anything and Flip the Script by Oren Klaff.

Daily habit: Quiet time at 5:30 a.m. to reset, reflect, and start each day with focus and calm.

#1 insight for building a strong network: Meet new people daily—whether at events or local REIAs—and prioritize face-to-face relationships.

• Visit DerekDombeck.com to explore resources, podcasts, and his books Next Level Your Life and The Transformational Journey.

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