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Maryland can feel like a pressure cooker right now, and not just for homeowners. We sit down again with Mike Griffith, a member of the Maryland General Assembly who also works inside the real estate closing world at Crown Title, to talk about what’s actually changing across the market and the state.  We also get specific about the costs that quietly crush returns: rising insurance, higher taxes, pricier labor, fuel surcharges, and maintenance that keeps climbing while rents struggle to keep up in certain areas.  If you care about Maryland real estate investing, the business climate, and the policy choices shaping your costs, this conversation will give you language and context you can use immediately.

A Half Ironman sounds heroic until you’re running in brutal heat with legs that want to cramp every step and aid stations that can’t keep ice stocked. We unpack what it felt like to survive the swim, gain ground on the bike, then get humbled on the run. Then we zoom out to what we’re seeing in the real estate market right now, and it’s not pretty. Rental vacancies linger, tenant placement is slower than it “should” be, resale listings sit without offers, and interest rates stay high enough to crush cash flow.  Finally, we share real stories about bad real estate agents, great agents, and how negotiation and competence can add or cost hundreds of thousands in a single deal.

The real estate market is changing, technology is accelerating, and artificial intelligence is quickly becoming one of the biggest forces shaping the future of business, investing, and wealth creation. We discuss how AI is changing business, real estate, and investing. From analyzing deals to making smarter decisions, and why adapting early could create major opportunities in the next decade. This conversation is not just about technology. It is about mindset, timing, strategy, and understanding how innovation can either disrupt you or become one of your biggest advantages.

What does AI actually mean for business owners right now? In this episode, we sit down with returning guest Jett Hennigan from Dreamers Event Rentals to talk about his move into AI and how he’s starting to use it inside a real business. He breaks down what “agentic AI” actually looks like when it’s wired into real tools like Zoho, QuickBooks Online, Google Drive, and your quoting process. We dive into what AI is already changing, the mistakes most people are making, and how to stay ahead as things move fast. The gap between people using AI and those ignoring it is growing quickly as this episode breaks down how to be on the right side of it.

Forty-six showings and only two offers tells you more about the market than any headline. We break down what we’re seeing as agents and investors right now: houses can still move fast, but only when they’re priced for reality, renovated the right way, and positioned to win in that first window before a listing goes stale. Then we get honest about rentals. Vacancies are up, applications are weaker, and it can be smarter to hold a unit empty than rush into a bad tenant and end up evicting after a fresh turnover.  We zoom out to the bigger money picture too: gas prices, war uncertainty, stock market swings, and why having an advisor or coach can matter when your risk profile, taxes, and timeline all change the “right” move. We cap it off with a fun shift into endurance mode as Nick signs up for an Ironman 70.3, including pacing goals, bike wattage, and the unglamorous truth about nutrition and sodium when cramps hit.

What happens when your passion for building collides with a market that won’t sit still? We dive straight into that crossroads—balancing a love for real estate and entrepreneurship with the realities of higher insurance, stubborn taxes, softening rents, and even a surprise sewer moratorium that freezes permits in a prime Maryland corridor. Along the way, we lean on the same mindset we use to train for 70.3 races: clear goals, steady inputs, and a willingness to pivot when conditions change. Underneath it all is a conversation about freedom numbers and lifestyle creep. We’re honest about what it really takes to feel secure, why health goals keep our discipline sharp, and how to pick strategies that fit your risk and season of life. If you’re weighing whether to buy, build, or borrow, this one gives you a practical framework and the trade-offs we’re making ourselves.

A rental portfolio doesn’t scale on grit alone. Matt Cox joins us to map the leap from single family BRRRRs to 10–40 unit apartments—all while living in Manhattan and buying in Oregon.  We dive deep into the small-multifamily sweet spot where mom-and-pop owners leave money on the table. Think stale insurance, unchecked utilities, no RUBS, and rent rolls with big gaps across identical units. Standardize operations, right-size expenses, and even a $100 rent delta at a six cap becomes meaningful value. On the build side, feeding AI your cost library turns blueprints into accurate material and labor takeoffs in minutes. We close on policy and affordability: tenant-friendly markets can be hard to operate in, yet scarcity often props returns—if you respect the rules, the risks, and the people whose money you steward.

A three-year waitlist for a watch you still can’t buy. A $1.2M piece you might be afraid to wear on the street. And the blunt truth about where money compounds versus where it just looks good. We took Boston by storm—recording at a glass-front studio in the TD Garden hub, drifting down Newbury Street’s luxury row, and stress-testing the logic behind status buys and durable assets. If you want a playbook that values both joy and prudence, this one’s for you. We map the line between smart splurges and compounding assets, share the systems that make portfolios durable, and call out the traps that drain profit.

What if the smartest way to build real estate wealth is not quitting your day job, but using it as fuel? Jeff Ervick joins us to map a step‑by‑step journey from cold‑weather BRRRRs to scalable multifamily syndications, private credit, and smart insurance structures—all while keeping a high‑earning W‑2 in tech.  Jeff is an accomplished Real Estate Fund Manager and Investor Relations Maverick. He has successfully deployed over $50M of equity across a $220M portfolio of assets under management and development, comprising multifamily, luxury SFH builds, ground-up development, Airbnb, and light/flex industrial properties.  Jeff’s LP and GP portfolio comprises over 2250 doors under management and development.

What if renting your primary home is the smartest move you can make in a seven-figure market? We welcome Krys Benyamein, a first-generation American who walked away from a public defender career to join his family’s Southern California brokerage, and he brings the kind of grounded clarity that cuts through housing hype. From LA County’s “million-dollar doesn’t feel like a million” reality to the psychology of leaving a prestige title, Krys shares a blueprint for building wealth and a life you actually like. Krys explains why he rents a $7k home instead of taking on an $11k mortgage, preserving capital and flexibility while holding low-rate assets that appreciate. Along the way, we connect ultrarunning and rock climbing to entrepreneurship—big goals are easy to announce and hard to resource, and the real work is designing a life that can carry them.

Want the playbook for turning a modest house hack into a durable portfolio without losing your sanity or your weekends? We sit down with Cory Jacobson to unpack the moves that matter: buying smarter assets, documenting relentlessly, raising capital responsibly, and building a life you actually want to live. Cory started in 2018 with a simple house hack and a promise to share the journey. That daily consistency built trust, opened doors to partnerships, and ultimately funded bigger, better projects.  If this hit home, follow, share with a friend who needs a push, and leave a quick review so more builders and investors can find the show. Your support helps us keep these conversations sharp and useful.

Today we’re joined by Kevin Cooney and Johnny Hilbrant (aka “PE GUY”) for a conversation that’s equal parts hilarious and surprisingly insightful—covering content, brand-building, and what it takes to turn internet momentum into a real business. Kevin breaks down how he and Ashley built The Cooney’s Show, a long-form podcast filmed at TD Garden in Boston interviewing entrepreneurs, entertainers, and athletes.  Johnny shares the origin story behind “PE GUY,” the deadpan private-equity parody that blew up online in 2025 and quickly grew to 250K Instagram followers

Real estate looks glamorous from the outside. Up close, the winners treat it like a craft and a job. We bring lender Ryan Studner into the studio at dawn to pressure‑test the strategies serious investors use right now: why new construction can beat heavy flips, how to keep capital moving while permits crawl, and what clean books reveal about “profits” that never existed. Ryan opens the lender’s playbook—credit, liquidity, and experience—and shows how disciplined underwriting protects both borrowers and the broader private credit market.  If you want a practical, lender‑tested way to build and hold through uncertainty—avoiding hidden losses, appraisal traps, and timeline drift—this conversation lays out the moves. Subscribe, share with a friend who’s scaling, and leave a quick review with your biggest takeaway so we can dive deeper next time.

If you’ve ever felt the grind of race-to-the-bottom bids or the whiplash of constant change-order fights, this conversation will feel like oxygen. We sit down with contractor Richard Amaya to explore why collaboration beats competition, how sharing systems accelerates growth, and when it’s time to pivot from investor work to homeowner projects that value quality over shortcuts. We get specific about what “doing it right” really costs: permits, inspections, and the sequencing that keeps trades aligned. Culture and communication matter just as much as contracts. We talk bilingual job sites, why speaking Spanish builds trust and speed, and how community dollars strengthen small businesses. Enjoy the conversation—and if we hit home, follow the show, share it with a builder friend, and leave a review to help more people find it.

Tired of watching cash flow slip through the cracks and flips turn into tuition? We dig into the operator’s playbook: how to stabilize rentals faster, build a right-sized property management team, and lean into new construction where execution is cleaner and margins are clearer.  Then we tackle the classic dilemma: build your own property management team or hire third-party? You’ll hear the real cost stack at 100+ doors, where the scaling ceiling hits, and how to split field work, admin, leasing, and maintenance coordination without burning out or overpaying. If you’ve wondered why some buyers are still overpaying for as-is homes, we share actual offers, ARV guardrails, and the price of wishful thinking. We talk novation-style options, when flips still make sense, and why we’re passing on thin spreads that don’t pay for risk.