This episode features a solo session with John Casmon, where he draws on personal investing experience in markets like Chicago, Cincinnati, Louisville, and San Antonio to share a deep-dive framework for evaluating which markets to invest in, and how to spot the signs of long-term growth. From understanding economic indicators and infrastructure to aligning your personal investing style with neighborhood dynamics, this episode is packed with strategic guidance on identifying the right market — and the right moment — to make your move.

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

Key Takeaways

• Start by investing in your own backyard, local familiarity and access outweigh national trends early on.

• Use "path of progress" logic to spot adjacent neighborhoods with similar fundamentals but lower prices.

• Look for population growth, industry diversification, infrastructure investment, and pro-development policies.

• Understand your own investing goals to determine what kind of markets and submarkets align with your criteria.

• Ride the coattails of developers and large employers, when they commit to a market, opportunity follows.

Topics

Why Market Selection Matters

• Why investing close to home gives you an advantage

• How John evaluated neighborhoods like North Center, Avondale, and Hermosa in Chicago

Expanding Beyond Your City

• Lessons from shifting to Cincinnati and using family ties to anchor new market exploration

• The importance of clarity on investor criteria before analyzing new areas

What Makes a Market Attractive

• Key indicators: population growth, job diversity, geographic accessibility

• Red flags: rent control, oversupply, misaligned development

Case Studies: Cincinnati, Louisville, San Antonio

• The impact of infrastructure and corridor development in Cincinnati

• How recession-resistant industries shaped John's decision to invest in Louisville

• Why San Antonio's "quiet strength" made it a strategic move

Using Public Data to Guide You

• Sites John uses: census.gov, bls.gov, datausa.io

• How to track local chambers of commerce, development plans, and funding incentives

What to Avoid or Watch Closely

• Risks of relying on government subsidies or unstable funding

• Importance of local political climate and long-term planning by municipalities

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Next Steps

• Research your backyard market before expanding elsewhere

• Align your criteria (cash flow vs. appreciation, investor type) before evaluating a market

• Track macro indicators (population, jobs) and micro conditions (local policy, neighborhood dynamics)

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.

Chris Wise is a Navy veteran, attorney, and founder of Wise Capital—a property technology company focused on upgrading Class C multifamily housing through in-house AI, IoT, and data systems. By combining real estate ownership with smart software development, he's redefining operations and improving tenant experiences across older multifamily assets. Based in Louisville, Kentucky, Chris brings a unique blend of military discipline, legal expertise, and tech innovation to the multifamily investing space.

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

Key Takeaways

• How Chris transitioned from Navy to law to real estate

• The North Star guiding his career pivots: social impact

• Why predictive maintenance is essential in Class C properties

• Using IoT and internal tech to reduce costs and extend asset life

• Real examples of tracking power and water consumption to prevent failures

• How in-house product development helps maintain affordability

Topics

From the Navy to Real Estate: A Career of Purpose

• Chris's path from Navy service to law school and legal practice

• How his passion for social impact shaped his professional pivots

Solving Problems Through Technology

• Founding a software and marketing firm to solve internal inefficiencies

• Learning to code and build tools to reduce costs for small businesses

The Rise of Wise Capital

• How Chris combined real estate and tech to launch Wise Capital

• Why Class C properties were the ideal target for smart upgrades

IoT and Predictive Maintenance in Action

• Identifying failing systems before they break: water, power, HVAC

• Using public product data and power consumption to monitor appliances

• Replacing $0.10 fuses instead of full appliances

Reducing Costs Without Raising Rents

• Keeping rent stable by slashing expenses through innovation

• Why many "smart" solutions don't make sense financially—and how to build better

Vertically Integrated Operations and Property Management

• Why Chris keeps property management in-house

• Hidden costs in third-party management that eat into NOI

Common Missteps in Value-Add Projects

• Misplaced renovation priorities (e.g., ignoring plumbing or sinks)

• Focus on function, pride of living, and true ROI over cosmetic updates

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Chris up for success: A marketing collapse at his former law firm pushed him to learn coding and product development. Though the failure cost mid six-figures, it laid the foundation for his current proptech innovations.

Digital or mobile resource recommended: Time-tracking or auditing tools—anything that helps buy back time, provided it's actually reviewed and used intentionally.

Book recommended most in the last year: Buy Back Your Time by Dan Martell.

Daily habit that keeps him focused: Wakes up at 4:30 AM to get centered—no screens, focuses on personal health, calendar prep, meditation or prayer before engaging with others.

#1 insight for managing your expenses: Track everything down to the penny. Understand your P&L deeply, including the small charges and hidden costs across all line items.

Favorite restaurant in Louisville, KY: Kern's Corner.

Next Steps

• To learn more, check out Chris' LinkedIn page.

• Audit your expenses before chasing higher rents

• Explore internal data solutions before investing in overpriced sensors

• Re-evaluate your property management structure for hidden fees

• Focus on functional, meaningful upgrades—not just cosmetic ones

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.

Joe Rinderknecht is the founder of Upgrade Partners Capital and Cowboy Capital, a real estate investment firm specializing in acquiring and operating value-add multifamily properties. With deep roots in ranching and a background in construction, Joe brings a hands-on approach to real estate, backed by years of entrepreneurial experience. His journey from working blue-collar jobs to managing complex multifamily assets reflects his drive to create generational wealth and live intentionally. In the past year alone, Joe and his partner Levi have closed on 419 units across several states—all while keeping family and values at the center of their mission.

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

Key Takeaways

• Learn why having a strong partnership can unlock rapid portfolio growth

• Understand how hands-on experience helps overcome construction challenges

• Discover the importance of aligning business strategy with personal values

• Get practical advice for vetting contractors and managing budgets

• Hear how transparent communication saved a struggling project

Topics

Joe's Ranching Roots and Entry Into Real Estate

• How Joe's upbringing on a ranch and construction background shaped his work ethic

• Transitioning from manual labor to entrepreneurship and finance

Hands-On Multifamily Management

• Lessons from managing an 80-unit property with high vacancy and crime

• Building operational skills through property management and acquisitions

The $3M Renovation Journey

• What went wrong on a 1951 property rehab—and what saved it

• Learning to navigate capital calls and manage contractor relationships

Lessons in Construction Oversight

• Why multiple contractor bids are essential

• Realizing cheaper isn't better when scaling projects

Building a Powerful Partnership

• How Joe found a long-term partner after multiple failed ones

• Dividing responsibilities and scaling with aligned values

Family First, Empire Later

• Why Joe and his partner are intentionally staying lean

• Long-term vision to build a bigger business after their kids are older

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Joe up for success: Under-communicating with investors during a major renovation project. The experience taught him the importance of having difficult conversations early, which ultimately strengthened his investor relationships and led to repeat capital commitments.

Digital or mobile resource recommended: Podcasts (especially for cutting down learning curves), including Multifamily Insights.

Book recommended most in the last year: Best in Class by Gary Lipsky

Daily habit that keeps him focused: Every night, Joe shares his daily wins and top three tasks for the next day with a coach to stay accountable.

#1 insight for overcoming obstacles: Action cures anxiety. Make decisions quickly and move forward—inaction only makes problems worse.

Favorite restaurant in Idaho: Red Net Sushi (a go-to spot for Joe, who loves sushi).

Next Steps

• E-mail Joe at [email protected]

• Check out Joe's website, cowboycapital.us

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.

In this week's solo episode, John Casmon steps away from guest interviews to break down one of the most misunderstood topics in multifamily investing: underwriting. After speaking at the Big Deal Summit in Columbus, John shares the real-world framework he uses to analyze deals—not just in spreadsheets, but in practice. From setting clear investment criteria to identifying operational inefficiencies, John walks through how successful investors combine vision, market insight, and execution to drive lasting results.

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

Key Takeaways

• Underwriting isn't about the spreadsheet—it's about the vision, people, and execution

• Always define your buy box and end goals before analyzing numbers

• Focus on markets with both macro strength and micro-level renter desirability

• Investors don't pay premiums for plumbing or electric—focus on visible value

• Operational inefficiencies are gold if you know how to identify and fix them

• Don't assume you can operate better than a seasoned owner without proof

• Stress test your assumptions: What happens if the plan breaks?

Topics

The Real Goal of Underwriting

• Spreadsheets don't reflect operations—real estate is about people, not numbers

• Get clarity on what kind of asset and community you're trying to build

Defining Your Buy Box

• Understand your own criteria before chasing ROI or IRR

• Why Cincinnati and surrounding markets meet John's standards for long-term growth

Macro and Micro Market Selection

• How renter desirability shapes submarket selection

• Population growth ≠ renter demand—context matters

Value-Add the Right Way

• Tenants won't pay more for new pipes—focus on kitchens, lighting, appliances

• Target properties with updated mechanicals so your upgrades actually add value

Operational Inefficiencies to Look For

• Low occupancy, slow turn times, bloated expenses, and misaligned staffing

• Why seasoned operators aren't always "mismanaging"—stay humble

Creating vs. Assuming Value

• Ask questions before opening a spreadsheet—what is the business plan?

• Don't guess your way through the numbers; know what levers create value

Stress Testing the Deal

• Underwrite break-even points and failure scenarios

• Real story: How one business plan unraveled when resident profiles clashed

Final Thoughts on Strategy

• Vision before budget—start with what you want to create

• IRR matters, but timing and exit assumptions often fail

• Know your buyer—plan your renovations around future investor demand

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Next Steps

• Join John's investor community at casmoncapital.com

• Download the free guide: 7 Questions Every Passive Investor Should Ask

• Revisit your underwriting process using John's value-first framework

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.

Nitzan Mosery is a serial entrepreneur, coach, investor, and host of the Traveling Investor radio show. With decades of experience across diverse industries—including renovation, hospitality, and jewelry—Nitzan eventually found his calling in multifamily real estate. Through firsthand trial and error, he built a powerful investing career focused on passive income, team scalability, and creative financing strategies. Nitzan is the founder of Multifamily Empire and teaches others how to build long-term wealth through value-add multifamily assets in emerging U.S. markets.

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

Key Takeaways

• Always verify tenant quality, market conditions, and neighborhood dynamics before acquisition

• Don't fall in love with the property, fall in love with the numbers

• Build systems and hire around your own zone of genius to scale effectively

• Trust is built by consistent visibility, social proof, and delivering real hands-on performance

• Capital raising only works if you've invested time building authentic investor relationships

Topics

From Restoration to Rentals

• How Nitzan transitioned from flipping houses and restoration to multifamily rentals

• The cash limitation problem that pushed him toward syndication and scaling

Hard-Earned Lessons from Early Deals

• His early duplex in Chicago and fourplex in West Palm, and what went wrong

• Why failing to verify tenants, management, and neighborhoods cost him

What Passive Investors Really Care About

• How he used mistakes to refine screening, team-building, and due diligence

• The red flags with PMs who own local units, and how to ask smarter vetting questions

Demographics, Market Research, and Value-Add That Actually Works

• Why Nitzan relies on a dedicated demographer to track population flows

• How his team validates value-add returns by examining proven rent comps

Raising Capital with Intent

• Why "money will come if the deal is good" is only half true

• Why educating and nurturing your network before a deal is critical to raising capital

Positioning Yourself for Institutional or Family Office Capital

• The exact conversation that unlocked a relationship with a family office

• Why showing up consistently (online and in-person) builds trust over time

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Nitzan up for success: The duplex and fourplex deals early in his career. He broke even but learned key lessons on market due diligence, tenant screening, and vetting teams.

Digital or mobile resource recommended: Opus Clip (for content creation), ChatGPT (for caption writing), GoHighLevel (for automation), and Audible (to read and listen simultaneously).

Book recommended most in the last year: Flip the Script and Pitch Anything by Oren Klaff.

Daily habit that keeps him focused: Nightly task review and scheduling. In the morning, he practices silent breathing meditation and begins his day with intention.

#1 insight for scaling a multifamily portfolio: Use other people's money, time, skill sets, and track records. Build your team around complementary zones of genius, success is a team sport.

Favorite restaurant in Florida: Boca Grill.

Next Steps

• Follow Nitzan at MultifamilyEmpire.com

• Try his 55-question "Multifamily Money Maker Role" assessment

• Join his free Skool community: Multifamily Moneymakers

• Download our 35 Hacks to Find the Best Submarkets guide

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.

Caleb Christopher is a real estate investor, entrepreneur, and one of the foremost minds in creative financing for residential properties. He's the founder of Creative TC, a consulting firm helping investors structure safe, legal, and ethical creative finance deals—including subject-to, seller finance, and wrap mortgages. He's also the creator of tools like the underwriting calculator and the partnership evaluator, and he's raising capital for ventures like his title company via innovative vehicles such as investment clubs. Caleb is passionate about building tools where none exist, solving complex problems, and creating upward mobility for the people around him.

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

Key Takeaways

• Always start creative deal conversations with the end in mind—even if the path is uncertain

• Get the seller's full story before pitching terms; relationship-building is critical

• Flexibility and an outcomes-oriented mindset are essential for creative structures

• Investment clubs can be a powerful capital-raising alternative to traditional syndications

• Solving the seller's future needs is often more important than hitting your own price targets

Topics

From Builder to Problem-Solver

• Caleb builds systems and solutions when existing tools don't meet his standards

• Created Creative TC to become an authority in ethical creative deal structures

Creative Finance 101

• Most deals start with a pricing mismatch—terms become the bridge

• Key is understanding the seller's backstory and aligning on a shared outcome

Being Outcomes-Oriented

• Investors must learn to zoom out and focus on results, not just checklist tasks

• Knowing multiple exit strategies allows for creative flexibility

Common Seller Profiles

• Single-family deals often involve financial distress

• High-price sellers may not be distressed but hold strong pricing expectations

Structuring for Mutual Success

• Price vs. terms: the seller gets one, you get the other

• Options like cash-out timelines, exit plans, and shared management responsibilities help mitigate seller risk

Challenges with Brokers

• Brokers often limit creative structures—direct seller conversations are more fruitful

• Investors must proactively communicate how brokers still get paid on creative deals

Raising Capital Legally

• Differentiates between syndication types (506b, 506c) and investment clubs

• Advocates for active participation structures and tools like Fractional to stay compliant

Investor Mindset and Scaling

• Many investors forget to consider the seller's needs—this kills deals

• Demonstrating good faith and offering safeguards builds trust and credibility

Lead Flow and Brand Positioning

• Caleb's unique positioning in creative finance draws complex deals his way

• Word-of-mouth and online presence help others know "this is the guy for creative"

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Caleb up for success: Company nearly went bankrupt due to cash mismanagement and market shifts. Came out stronger and more selective about partnerships—only works with people who've been through tough situations and grown from them.

Digital or mobile resource: His own Partnership Evaluator worksheet that helps partners assess each other before starting a business or investment deal.

Book recommendation: Made to Stick by Chip and Dan Heath

Daily habit: Reads the Bible every morning, writes down intrusive thoughts on a checklist to stay focused, and sends a daily briefing to his team.

#1 insight for structuring creative deals: Start with a cash offer. Then get the seller's full story—only then can you structure something that works.

Favorite restaurant in Kansas: Joe's KC.

Next Steps

• Connect with Caleb at calebchristopher.io

• Sign up for his newsletter to access his real numbers, case studies, and behind-the-scenes operations

• Explore his creative finance consulting and capital-raising strategies

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.

Evan Polaski is the Director of Capital Raising at Black Gate Partners, where he leads investor relations and capital strategy for multifamily real estate syndications. With 18 years of commercial real estate experience—including roles in retail development, multifamily investments, and investor communications—Evan brings a rare blend of institutional perspective and hands-on execution. He has invested as both a general and limited partner and is known for his candid approach to alignment, underwriting scrutiny, and investor education.

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

Key Takeaways

• Great deals and abundant capital rarely align—it's always a pendulum

• A conservative deal today may have felt aggressive just 24 months ago

• True GP-LP alignment is nuanced and difficult to achieve—acquisition fees often skew incentives

• Passive investors should study sponsors' fee structures, co-investments, and transparency

• The best investor relations approach isn't sales—it's expectation management

Topics

Falling in Love with Real Estate Early

• Evan's fascination with real estate began as a child watching shopping centers being built in Atlanta

• Studied finance and real estate at the University of Cincinnati, and started in retail REIT investor relations

• Has worked across roles in capital raising, investing, and ownership

The Market's Capital-Deal Imbalance

• Capital and deal quality are rarely in sync—one is always scarce

• 2021–2022 saw capital flood the market, but often into weak deals

• Today feels like 2009 again, with conservative investors and fewer phone calls returned

Lessons from the Downturn

• Floating-rate loans and short-term debt—not real estate quality—are behind many failed deals

• Evan cautions that "safe" real estate only stays safe with proper structure and conservative assumptions

• Overly optimistic IRRs, misaligned capital stacks, and loose underwriting have been exposed

On Alignment and Fees

• Evan focuses on age and experience as critical factors when evaluating GPs

• Acquisition fees deserve close scrutiny—especially when they exceed co-investment amounts

• Sponsors who transact just to earn fees raise red flags around long-term alignment

Managing Investor Expectations

• Great IR is about setting, managing, and exceeding expectations

• LPs who receive clear, accurate communication—regardless of performance—stay engaged longer

• Sales-driven approaches often lead to mismatches in trust and long-term relationships

Navigating Growth and Team Building

• Scaling a syndication business brings team demands—growth isn't always about ego

• Even small increases in payroll or promotions require deal flow and capital

• Balance between investor returns and internal sustainability is delicate and evolving

Track Record and Debt Structure

• IRR isn't enough—investors should ask how much of a return came from NOI growth vs. cap rate compression

• Evan favors sponsors who have survived downturns and learned from risk exposure

• Floating debt creates the illusion of strong deals—fixed-rate debt demonstrates stability

📢 Announcement: Learn about our Apartment Investing Mastermind here.

Round of Insights

Failure that set Evan up for success: Getting laid off in 2009 opened his eyes to how macroeconomic shifts and capital structure can impact everything, including LP returns and employment.

Digital or mobile resource: LinkedIn. When curated well, it can be a source of valuable insights and perspectives from across the investing world.

Book recommendation: The JOLT Effect by Matthew Dixon & Ted McKenna, a tactical guide to overcoming objections and improving sales communication.

Daily habit: 6 a.m. CrossFit workouts. This anchors his morning routine, clears mental clutter, and helps structure the rest of his day.

#1 insight for selecting great operators: Follow them for at least 6–12 months before investing. Pay attention to how they communicate, especially when you tell them you're not ready to write a check.

Favorite restaurant in Cincinnati, OH: For date night: Losanti. For casual family dinners: Northstar Café in Kenwood.

Next Steps

• Connect with Evan on LinkedIn

• Learn more at GoBlackGate.com

Thanks 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.

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.