In this episode of Zen and the Art of Real Estate Investing, Jonathan sits down with Tim Woodbridge, co-founder of WCG Investments, to discuss how he transitioned from a healthcare career to building a portfolio of 19 mobile home parks across the Southeast. Tim shares the lessons he's learned about scaling through partnerships, managing risk with conservative underwriting, and improving communities through value-driven operations.

The conversation explores his early challenges finding deals, developing trust with brokers and lenders, and learning how to take imperfect action without losing discipline. Tim explains why collaboration and follow-up matter as much as capital, what separates good due diligence from guesswork, and how his team builds sustainable systems to support investors and residents alike.

This episode offers a grounded look at what it takes to grow in a niche asset class while maintaining long-term perspective, thoughtful leadership, and a genuine focus on people.

In this episode, you will hear:

• How partnerships built on complementary strengths lead to better deals
• The importance of trust and transparency with brokers and lenders
• Common due diligence pitfalls that can derail returns
• Why realistic underwriting protects both operators and LPs
• How consistent follow-up leads to unexpected opportunities
• The role of community improvements in responsible investing

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Supporting Resources

Connect with Tim Woodbridge

Website: www.wcginvestments.com

Youtube: https://www.youtube.com/@WCGInvestments

Facebook: https://www.facebook.com/wcginvestments

Instagram: https://www.instagram.com/tim.woodbridge/

LinkedIn: https://www.linkedin.com/in/timwoodbridge/

E-Book - https://wcginvestments.cashflowportal.com/leads/e-book

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

Jonathan welcomes Max Emory, founder of Time Capital Bookkeeping & CFO Solutions, a bookkeeping educator and active investor. Together, they explore why clean books form the foundation of every real estate business and how accurate categorization impacts both taxes and lending. Max explains what decision-ready financials allow investors to do, including timing acquisitions, managing cash flow, and avoiding costly tax surprises. He also shares why onboarding with a professional bookkeeper is intensive but worthwhile, how your bookkeeper, CPA, and attorney should collaborate, and the most common financial pitfalls he corrects for flippers, wholesalers, and landlords.

Max shares his path from serving in the Marine Corps to purchasing his first duplex in Columbia, South Carolina, and scaling through clustered small multifamily properties using the BRRRR strategy. He discusses early challenges such as hiring and firing property managers, building a technology-driven team, and using neighborhood comps and appraisals to improve accuracy. He explains how commingling funds can disrupt operations and increase bookkeeping costs, how simple categorization mistakes can inflate taxable income by thousands, and how to adjust profit and loss reporting to support specific goals, whether maximizing lendability or minimizing taxes.

Listeners will leave with a clear checklist for preparing to hire a professional bookkeeper, an understanding of which financial metrics matter most, and the confidence to treat bookkeeping as a strategic advantage rather than a yearly obligation.

• Why bookkeeping is the financial foundation—and how it drives tax strategy, lending, and acquisitions

• The most expensive mistakes Max sees (miscategorization, commingling, missing capex visibility)

• How to align your bookkeeper, CPA, and attorney so your entity structure helps operations

• A simple starter system for receipts, statements, and deal docs (even before you hire help)

• When and why to keep taxable income high (and when to compress it)
  
  

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Max Emory

Website: https://www.timecapitalbcs.com/

Youtube: https://www.youtube.com/@millionairebookkeeper

Facebook: https://www.facebook.com/themaxemory

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

LinkedIn: https://www.linkedin.com/in/millionairebookkeeper/

Tik Tok: https://www.tiktok.com/@timecapitalbcs0?lang=en

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

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

TikTok - www.tiktok.com/@trustgreene

Zillow - www.zillow.com/profile/StreamlinedReal

Bigger Pockets - www.biggerpockets.com/users/TrustGreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio

On this week's episode, Jonathan welcomes Jon Wells, a real estate matchmaker, syndicator, and longtime realtor with A Better Way Realty and managing partner at Alpha Network—for a candid look at what actually builds durable wealth. Jon traces his journey from early "fix-and-flips" to higher-conviction "fix-and-holds," and ultimately to group homes leased on commercial-style terms. He explains why patience, operator quality, and underwriting discipline matter more than shiny objects, and how aligning with the right partners turns headaches into hands-off income.

As the conversation unfolds, they unpack contractor pitfalls, slim-margin flips that turn into flops and the relief of triple-net-style leases where the business, not the landlord, handles the day-to-day. Jon shares why he prefers renting large, lightly modified homes to sober-living/mental-health operators (versus carving up houses), why meeting new operators is the hardest part of this niche, and how option agreements can create shared upside. They also dive into passive vs. active choices, due-diligence checklists for syndications, and the value of investing in what you truly understand.

Listeners will come away with a calmer, longer-term lens: start with who you trust, de-risk with questions that reveal how an operator thinks, and don't mistake speed for progress—especially when cash flow and sleep-at-night returns are the goal.

• Why slim margins turn flips into long, stressful holds—and how to avoid it.

• The group-home model Jon uses: bigger homes, egress and safety upgrades, and commercial-style leases to vetted operators.

• Triple-net thinking for residential assets: fewer calls, clearer responsibility, steadier income.

• Trust and due diligence: the questions that de-risk syndications and funds—and when "no answer" means "no deal."

• Why investing in what you actually know (and who you truly trust) beats chasing neon "opportunities."

• How to choose between passive and active plays based on temperament, skills, and season of life.

If you enjoy the show, please follow Zen and the Art of Real Estate Investing on Apple Podcasts and leave a rating and review. It helps other listeners discover these conversations and supports the show's growth.

Connect with Jon Wells

Connect with Jonathan:

Website - www.streamlined.properties

YouTube - www.youtube.com/c/JonathanGreeneRE/videos

Instagram - www.instagram.com/trustgreene

Instagram - www.instagram.com/streamlinedproperties

Zillow - www.zillow.com/profile/streamlinen​j

Bigger Pockets - www.biggerpockets.com/users/jonathangreene

Facebook - www.facebook.com/streamlinedproperties

Email - info@streamlined.properties

This episode was produced by Outlier Audio