Tyler Wilson is a guru in his field of lending money, but it was a long road with difficulties and tough lessons to get there. Tyler shares with JD his story of building a real estate portfolio from nothing, failures, successes and the ups and downs of the financial industry over the past 20 years.

Tyler breaks down everything from market cycles, mid-term rentals, DSCR loans, and Fannie/Freddie updates, to how investors should position themselves ahead of 2026 rate drops. He also shares personal stories — including buying his first home in the 2007 crash — and the strategies that helped him build his own portfolio.

Whether you're a new investor or scaling to 10+ properties, this episode provides the exact market insights, zip code strategies, lending hacks, and AI-powered forecasting tools that can level up your investing decisions in North Alabama and beyond.

00:00:17 | The Future of Homeownership: 3D Printed Homes & Smart Homes

Predictions about automated homes, consumer–property interaction, and tech-driven lending.

00:01:11 | Tyler Wilson’s Background & Entry Into Lending

Finance degree, buying his first home in 2007, and how the housing crash guided him toward becoming an advisor.

00:03:03 | Comparing the 2007 Market to Today’s Lending Standards

NINA loans, zero-down loans, and the shift toward stricter post-crash regulations.

00:06:09 | Investment Windows: Why 2024–2026 Is a Key Opportunity

Why Tyler believes we're entering a “sweet spot” for buying.

00:08:18 | Cash Flow vs Appreciation in North Alabama Zip Codes

Breakdown of Huntsville, Madison, Research Park, and Cummings Corridor strategies.

00:08:59 | Vacancy Rates, Inventory Trends & Sub-$250K Homes Returning

140% increase in affordable listings and why older Huntsville homes are back on market.

00:10:45 | How to Forecast Appreciation Using Investor Tools

Tyler shares analysis methods using zip codes & MLS data.

00:13:09 | Why Rates Dropping Will Trigger a Market Surge

Explaining pent-up demand and why waiting may backfire.

00:18:08 | The Role of AI in Mortgage Efficiency & Job Disruption

Industry shifts, Amazon layoffs, and efficiency gains.

00:20:58 | The Loan Officer vs Mortgage Advisor Difference

Why loan officers may be replaced — but advisors won't.

00:22:46 | Building a Strong Lending & Investing Team

Importance of long-term lender relationships, title companies, insurance partners, and financial planners.

00:39:40 | Traditional Loans vs DSCR, Non-QM & Hard Money

When to use each, risks, benefits, and why traditional lending builds long-term wealth.

00:41:19 | Hard Money Lending Risks for New Investors

Loan sharks, prepayment penalties, and why beginners should avoid it.

00:35:00 | How Tyler Built His Own Portfolio & Uses Equity Strategically

Using HELOCs, appreciating markets, and smart leverage to climb the property ladder.

Bringing Local to Banking: North Alabama native Matt Davis has spent a life in banking. Matt takes JD from his early years in Hazel Green to leading the startup of Nova Bank in Huntsville, where he currently serves as the president.

Matt shares his journey from JUCO baseball player to commercial lender to bank executive, and how he and a group of Huntsville leaders navigated federal regulation, capital raising, merger transitions, liquidity management, risk, and community investment to launch Huntsville’s first new locally headquartered bank in decades.

Topics Covered with Timestamps

01:19 – Introducing Guest Matt Davis

JD and Matt discuss their long friendship and shared background.

02:33 – First Job Out of College: Selling Postage Meters

How Pitney Bowes and early B2B sales prepared him for a career pivot.

03:18 – Entering Banking: Wachovia, SouthTrust & Early Lending

Matt’s unexpected shift into banking after moving back to Huntsville.

04:15 – Becoming a Branch Manager at North Alabama Bank

How community banking exposed him to all lending types and accelerated his learning.

04:52 – Banking Through the 2007–2009 Recession

Front-row exposure to real-world credit, underwriting, and distressed assets.

06:11 – Joining National Bank of Commerce & the Merger Era

NBC → CenterState → SouthState: Lessons from major mergers and acquisitions.

07:25 – Why Big Banks Often Don’t Fit Local Borrowers

How large institutions shift toward middle-market lending and away from small investors.

08:12 – The Birth of NOVA Bank (2020–2023)

The idea, early investors, regulatory requirements, and COVID-era challenges.

09:23 – Raising $4M in Seed Capital & Undergoing FDIC Vetting

Background checks, regulatory filings, leadership vetting and more.

10:27 – Leaving a Stable Job to Start a Bank

Matt takes the entrepreneurial leap, leaving South State to lead NOVA’s capital raise.

11:13 – Raising $21.5M Minimum (and Ultimately ~$27–28M)

Why NOVA aimed for 6 months instead of 12, and how they contacted 2,000 people to close investors.

13:59 – Understanding Investor Psychology & Handling Rejection

Improving the pitch and staying disciplined during capital raise.

16:38 – Quiet Launch Phase: Technology, Debit Cards & Buildout

Why debit cards took 8 months and how banks prepare behind the scenes.

17:56 – Digital Banking Strategy & Low Overhead Model

Why modern community banks thrive without heavy brick-and-mortar.

18:57 – Meeting Customers Where They Are: Convenience Banking

Customer service rooted in texting, calls, mobile deposits, and relationships.

20:00 – NOVA Bank’s Madison Street Branch & Ribbon Cutting

Public opening after months of soft-launch testing and operations.

21:15 – Regulatory Requirements After You Open a Bank

Liquidity, asset ratios, concentration risk, ongoing monitoring.

22:12 – Loan Portfolio Strategy & Concentration Limits

Why NOVA prioritizes single-family investors, construction, CRE, C&I loans, and cash products.

26:00 – Winning the National Bank Simulation Competition

How his team outperformed 75 other banks using disciplined strategy.

31:00 – Why Huntsville Needed a Truly Local Community Bank

Filling the void left after major acquisitions eliminated local headquarters.

33:00 – Lessons From the 2008 Crash & Subprime Crisis

Risks of “quick and easy loans” vs. responsible local lending.

35:21 – Understanding What Types of Borrowers NOVA Bank Serves Best

Why NOVA focuses on investors buying 1–4 homes per year, small business owners, and referrals.

38:02 – Selecting the Right Investors & Upholding Character Standards

Why NOVA turned down certain out-of-market investors.

40:07 – Building a Board & Team You Can Call Anytime

Community expertise, collaboration, and being a good steward of capital.

41:59 – Why Deposit Growth Is the Fuel for Lending

Deposit strategy, rates, and why young banks must be hungry.

Russ Hayles made a career change over a decade ago to become a full-time investor and real estate salesman. JD and Russ break down his decisions to go from an economics professor and high school teacher to real estate guru. Russ openly discusses his strategies, tips and advice on how others can make a similar transition. Flips, long-term holds and sales are all on the table for this conversation. Russ shares how his background in economics shaped his approach to decision-making (including the sunk cost mindset that every investor must master), the hard lessons from his first flip gone wrong, and how he built a scalable partnership model to grow a portfolio of over 25 rental properties—without chasing hype or speculation.Topics Covered with Timestamps00:01:14 | Introducing Guest: Who is Russ Hales?

00:01:26 | Transitioning from Teaching & Coaching to Real Estate

00:03:55 | The First Flip: Buying on Whitesburg & Everything That Went Wrong

00:05:00 | Foundation Failures, Redos & Learning the Hard Lessons

00:08:51 | Understanding Sunk Cost Fallacy in Real Estate

00:10:54 | Making Decisions Based on Current Facts — Not Past Spend

00:13:31 | Advice to Sellers: Why Repairs Don’t Always Add Sale Value

00:15:19 | Pricing Strategy: Quick Sale vs. Waiting for the Right Buyer

00:16:24 | Deciding Flip vs. Buy-and-Hold: How Russ Evaluates Each Property

00:18:01 | Portfolio Snapshot: 26 Rentals & The Cash Flow Reality

00:21:51 | The Short-Term Rental Pivot: When Huntsville Changed the Rules

00:23:20 | The Truth About Airbnb Restrictions in Huntsville

00:26:31 | Long-Term Plan: Paying Off Rentals for Retirement Cash Flow

00:29:13 | Partnership Structure: Dividing Labor & Avoiding Conflict

00:32:15 | Life Balance & Humor: Still Playing Basketball at Age 43

In this episode of The 256 Investor Podcast, Huntsville, AL wealth and financial advisor Cameron West stops by to share advice and insight through a life in money management. Cameron and JD discuss how to create and enjoy the benefits of real estate investing, alternative strategies for tax avoidance, why other investing outside of real estate is important, and how to help good people worry less about their finances.

Topics Covered with Timestamps

00:00 | The Great Divide Between Real Estate Agents & Financial Advisors
Why the two industries often clash — and how diversification bridges the gap.

02:00 | From Preachers to Portfolio Managers
Cameron shares his family legacy in finance, growing up with Dave Ramsey’s first endorsed providers, and how it shaped his financial mindset.

06:00 | First Steps in Real Estate & Owning a Coffee Shop
How a financial advisor got into property ownership and small business investing.

08:00 | Diversifying Without Overextending
Cameron explains the value of spreading investments across real estate and markets — and the inefficiencies that make real estate profitable.

13:00 | Creative Tax Strategies for Investors
Breaking down 1031 Exchanges, Delaware Statutory Trusts (721s), and REIT conversions to defer taxes and retain income potential.

17:00 | Flipping Homes Using a Self-Directed IRA
How Cameron uses self-directed retirement accounts to flip homes tax-deferred — a smart workaround to avoid ordinary income taxes on short-term flips.

23:30 | Smart Budgeting in the Real World
Why automation beats micromanagement — and which budgeting tools actually work (Mint, Monarch, YNAB, EveryDollar, Copilot, etc.).

29:00 | The Psychology of Spending & the Dave Ramsey Effect
Understanding financial peace vs. financial freedom — and when discipline beats emotion.

36:00 | Maxing Out Your 401(k) — Or Not?
When it’s smart to invest outside retirement accounts to maintain flexibility and liquidity for business opportunities.

42:00 | Teaching Kids About Money
How to instill financial confidence in the next generation — from “spend/save/give” envelopes to early investment accounts.

46:00 | Generational Investing & Compound Growth
The story of a 31-year-old millionaire whose father started investing $5 birthday gifts early — proof that small seeds grow big wealth.

52:00 | Love, Marriage & Money Management
Handling financial imbalance between spouses — from budgeting conversations to automation and emotional awareness.

58:00 | Subscriptions, Overspending & Hidden Costs
Modern money traps: unused memberships, streaming overload, and the importance of tracking recurring expenses.

In this episode of the 256 Investor Podcast, local insurance expert Will Wright joins JD for a deep discussion on insurance claims, how it really works and how to be in control and get the best of your policies. Will Wright is the founder of The Will Wright Agency in Decatur, Alabama. With over three decades of experience in property, casualty, and life insurance, Will breaks down the real truths behind homeowners and rental property coverage — from how to file a claim that actually gets paid to understanding how insurance cycles impact your bottom line.

Topics Covered with Timestamps

00:01:06 | Meet Will Wright

Will shares his 30-year journey from life insurance agent to independent agency owner.

00:02:27 | The Truth About Insurance Cycles
Why rates rise and fall every 5 years — and how savvy investors can take advantage.

00:03:37 | When “We’ll Never Cancel You” Isn’t True
Will exposes major carriers that drop customers despite promises of lifetime coverage.

00:05:09 | Agents Who Care vs. Agents Who Don’t
How to spot a good insurance agent — and why your agent’s involvement can make or break a claim.

00:07:55 | The Hidden Risk of Filing a Claim
How filing without proof can raise your rates even when you’re denied.

00:08:13 | What Makes a Valid Roof Claim
Will explains how roofers and adjusters evaluate hail damage and why proper documentation matters.

00:10:18 | Tornado & Catastrophic Losses Explained
How “cat loss” events affect adjusters, agents, and your payout potential.

00:11:55 | Managing Properties from Out of State
Essential steps for investors who rely on property managers to file claims correctly.

00:14:20 | Deductible-Coverage Policies
A new insurance product that covers up to $25,000 of your deductible for tornado losses.

00:15:19 | How to Appeal a Denied Claim
The step-by-step process to re-open a claim and increase your odds of success.

00:18:19 | When Not to File a Claim
Why using insurance for “maintenance” causes premiums to skyrocket — and what to do instead.

00:20:19 | Common Water Damage Claims
Burst lines, leaking hoses, and other hidden risks that lead to expensive water losses.

00:23:01 | Slow Leaks vs. Sudden Losses
How insurance defines “sudden and accidental” — and why slow leaks are almost always denied.

00:24:00 | The Mold Myth
Why most mold claims are denied and how minimal coverage really works.

00:27:03 | Investor Insurance Strategy
Will shares practical advice for investors — higher deductibles, fewer riders, smarter cash flow.

00:29:22 | Multifamily Coverage Challenges
Why insuring 5+ unit properties is difficult and costly in today’s market.

00:31:17 | Metal Roofs & Cosmetic Damage Clauses
The fine print that can leave you uncovered after hail damage.

00:32:34 | Final Advice for Investors
Budget for maintenance, use insurance wisely, and “buy low, sell high.”

00:33:00 | Contact The Will Wright Agency
Will shares how investors can reach his office in Decatur, Alabama.

Two years ago, Stephen and Amanda Stockbridge sold their Huntsville home and hit the road for 2,000 miles to start mission work in Baja California, Mexico. In this inspiring episode of The 256 Investor Podcast, Stephen joins JD to discuss the importance of the biggest investment we can make. Stephen shares how selling his biggest asset—a home he once thought he'd never leave—became the key to early financial freedom and a new life of purpose.

Together, they explore what it means to redefine wealth, how homeownership can be both a financial and spiritual investment, and how major life transitions can open the door to deeper fulfillment. Stephen also opens up about his and his wife Amanda’s work combating domestic violence, providing medical outreach, and launching English language programs in underserved Baja communities.

Whether you're an investor thinking about your next move or someone seeking purpose beyond the paycheck, this story proves that smart financial decisions can lead to extraordinary impact.

Topics Covered with Timestamps:

00:01:15 | Meet Stephen Stockbridge – From Huntsville to BajaStephen shares his background, how he and his wife became missionaries in Baja California, and the nature of their work supporting local churches and communities.

00:03:00 | Challenges in Mexico & Domestic Violence AwarenessStephen discusses cultural challenges, including domestic violence in Mexico, and how their ministry is addressing these sensitive issues through education and outreach.

00:05:30 | The Turning Point – Selling Everything to ServeStephen and JD reflect on his life-changing decision to sell his house, retire early from landscaping, and fully commit to missionary work.

00:07:06 | Real Estate Insight – When Your Home Becomes an InvestmentJD connects Stephen’s story to Rich Dad Poor Dad principles—how a home can become a launching pad for new opportunities when viewed strategically.

00:09:45 | Timing the Market & Making the SaleStephen shares how perfect timing and the Huntsville housing boom doubled his home’s value, making his mission dream financially possible.

00:12:00 | Homeownership Lessons & Long-Term PayoffsThey reflect on the power of homeownership as a tool for stability and freedom—and how choosing to buy instead of rent made all the difference.

00:14:00 | Life in Baja – Language, Culture, and ServiceStephen talks about learning Spanish, starting English classes for locals, and creating programs that bridge educational and cultural gaps.

00:16:30 | Minimalism & Letting Go of Material ThingsHe describes the emotional process of downsizing—selling, donating, and keeping only what fit in a 16-foot trailer—and what it taught him about priorities.

00:18:53 | Redefining Wealth & HappinessStephen reflects on leaving behind the American “rat race” for a life defined by service, simplicity, and purpose in Mexico.

00:20:26 | Closing Thoughts & Call to ActionJD wraps up the conversation, sharing how listeners can support Stephen’s mission work and reminding investors that financial freedom isn’t just about money—it’s about meaning.

In this powerful episode of the 256 Investor Podcast, Antonio McGinnis, Executive Director of the Huntsville Housing Authority, catches up with JD on section 8 investing in Huntsville, AL. Tony grew up in public housing, played college basketball and pro ball overseas, and ultimately returned to his hometown to now lead the HHA. We cover the history of public housing in Huntsville and the housing choice voucher program, the benefits for both the investor and consumer, and advantages to working with the HHA.

Whether you’re a real estate investor considering participation in Section 8, a landlord curious about the process, or simply someone who wants to understand the truth about affordable housing in Huntsville, this episode is packed with insights you won’t want to miss.

Topics Covered with Timestamps

• [00:01:17] Growing Up in Huntsville Public Housing – Tony’s early life in Mason Court and Sparkman Homes

• [00:01:58] Basketball Journey – From Butler High School MVP to Texas A&M and pro basketball in Slovenia & Australia

• [00:06:00] Career Shift – From Boys & Girls Club leadership to Huntsville Housing Authority

• [00:08:49] Becoming Executive Director – Path to leading HHA and the organization’s 85-year legacy

• [00:09:50] Public Housing in Numbers – Units, Section 8 vouchers, and overwhelming demand

• [00:10:22] Understanding Section 8 – Landlord rights, inspections, myths, and responsibilities

• [00:13:33] Dispelling Myths – Tenants do work; landlords retain full screening control

• [00:17:04] Who Qualifies for Housing – AMI ranges, working families, and income-based assistance

• [00:20:24] Path to Homeownership – Turning vouchers into mortgages and ownership opportunities

• [00:21:13] Landlord-Tenant Relationships – Building partnerships and accountability on both sides

• [00:22:11] Program Strengths – Why Huntsville’s Housing Authority is high-performing

• [00:23:42] Transparency & Community Engagement – Annual meetings, open communication, and dispelling stigma