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