The Everyday Millionaire Show

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. 

Most investors are fighting for scraps in crowded flips. We took a different path. Ryan, Chase, and new guest Justin Hilz breaks down his 0% seller-finance win in Annapolis: how he framed the seller’s tax problem, structured principal-only payments, and added a balloon for exit flexibility without taking a 7% mortgage on the chin. From there, we zoom out to the market. Sub-$300k homes still fly, but move-up buyers are locked by 3% mortgages and bracing for payment shock. Looking for leverage without speculation? We also get tactical about financing new builds without bleeding interest—use creative lot terms, pay permits out of pocket, wait to trigger hard money until foundation, and only pay interest on draws.  Subscribe and share this with a friend who loves real estate and small businesses.

Join Ryan, Nick, and Chase on a brand new episode as they discuss the real estate market, as it faces a mix of challenges and opportunities, leading to a "corrugated" or uneven recovery rather than universal struggles. The conversation deep dives on their opinions behind Charlie Kirk's death and how society is more divided now more than ever. Plus, Ryan and Chase share their experiences as they prepare for their first full Ironman race. If you're an investor who prioritizes physical wellness and is hopeful about the future of our nation, then this episode is for you.

Erik Brenner pulls back the curtain on wealth management strategies that were once exclusive to the ultra-wealthy but are now accessible to everyday millionaires. With 32 years of experience operating both wealth advisory and tax accounting firms, Erik delivers practical insights that bridge the gap between financial planning and tax strategy. Whether you're a business owner, medical professional, or high-income earner, this episode delivers actionable strategies to optimize your finances. As Erik notes, success in wealth management isn't just about making money—it's about keeping more of what you earn through intelligent planning and tax strategy.

From island hopping in the Philippines to building million-dollar real estate developments, this episode takes you on a journey through entrepreneurial growth, strategic networking, and authentic business building. Ryan kicks things off with tales from his Philippines adventure – navigating a grueling 48-hour journey across multiple continents only to immediately dive with whale sharks upon arrival. His cultural immersion with his Filipino VA, Carl, highlights the value of building strong relationships which encompasses a professional one. From Carl staying shredded despite mountains of rice to  experiencing pristine beaches with affordable luxury provide a fascinating glimpse into Filipino culture. The conversation shifts to the entrepreneurial mindset and how they invest in coaching despite being coaches themselves. This cycle of continuous learning demonstrates why surrounding yourself with people who are where you want to be accelerates success.  As they prepare for their upcoming Ironman race and announce two exciting networking events, one thing becomes clear – success leaves clues, and those clues often appear in the people you choose to surround yourself with. 

What happens when your account information ends up for sale on the dark web after a single stolen check? In this eye-opening conversation, Ryan and Nick dive deep into the financial vulnerabilities many real estate investors face and the critical systems needed to protect your business. The conversation takes an unexpected turn as Ryan prepares for a two-week international trip—a true test of whether his business systems can function without him. This "two-week test" offers valuable insights for any entrepreneur looking to build a self-sustaining operation rather than an owner-dependent job. Ready to strengthen your real estate business and build systems that work even when you don't? This episode delivers actionable strategies from investors who are doing exactly that. Join us and discover how to protect your financial future while creating space for personal growth.

Jimy Chavarria brings a truly unique perspective to real estate investing through his ability to bridge cultural and linguistic gaps in an industry where communication is everything. From his unexpected origins studying to be a Spanish teacher to building a construction company and mentorship network, Jimmy reveals how being bilingual became his "superpower" in working with Spanish-speaking crews and communities. This insight proves especially valuable for Spanish-speaking contractors who already excel at construction but need guidance navigating deal structures and building credit properly. Through his Spanish-language podcast and nationwide mentorship approach, Jimy has created a ripple effect where successful mentees go on to teach others, multiplying his impact across communities. Ready to connect with other real estate professionals? Join us at our next networking event on July 31st in Timonium. It's completely free—no sales pitches, just genuine connections with investors, contractors, lenders and service providers who can help you grow your business and build wealth through real estate.

The landscape for real estate investors in Maryland has never been more challenging. In this eye-opening conversation with Maryland State Delegate Mike Griffith, we uncover the harsh realities of new legislation that threatens property rights and financial viability for both professional and mom-and-pop landlords across the state. This episode is also filled with light moments, as Ryan and Chase discuss their experiences from their last Ironman race. From quad cramps, to 6-digit bicycles, the world of triathlons could've never been easier and more expensive at the same time. And to wrap up the episode, Chase goes on a full-charged barrage on a company where he recently purchased a cold-plunge for post-exercise recovery. Whether you're a seasoned real estate investor or an avid triathlete, this conversation provides crucial insights into navigating Maryland's increasingly hostile regulatory environment and the reality of balancing business and physical fitness at the same time.

What happens when those "forever" rental properties start showing their age? In this candid conversation, Ryan reveals his complete strategy shift after realizing his decade-old properties now face expensive repairs that would consume years of cash flow. The conversation shifts to marketing techniques that have generated substantial business without spending a dime. From Facebook group strategies to relationship building within industries, we share actionable tactics that have yielded immediate results. Ryan recounts his car-buying nightmare as a masterclass in what not to do in customer service, while the team's Ironman training journey offers powerful insights on discipline, accountability, and finding fulfillment beyond business. This episode delivers practical wisdom from investors who continually evolve their strategies as their wealth and circumstances change.

When random internet strangers decide to roast you about your boat trailer, you might as well lean into it and laugh along. That's exactly what Ryan does in this episode as he recounts his experience going viral for all the wrong reasons. A casual video about boat repair costs unexpectedly blew up to 1.4 million views, all while the resulting comment section battles became their own form of entertainment, proving once again that social media is unpredictable, brutal, and occasionally hilarious. The conversation shifts to their real estate ventures, revealing both successes and struggles. Whether you're fascinated by real estate investing, training for endurance events, building businesses, or just enjoy authentic conversations about wealth-building, this episode delivers valuable insights wrapped in engaging, often humorous dialogue. 

The real estate market is showing conflicting signals, with some properties receiving multiple offers while others sit vacant for months. Ryan, Nick, and Chase explore this volatility and share their firsthand experiences navigating today's challenging investment landscape. With rates hovering in the 6-7% range, the traditional approach of rapid property accumulation deserves reconsideration. Some investors now focus on aggressively paying down existing debt rather than acquiring new properties, potentially using paid-off assets to secure lines of credit for future investments.

Justin Goodbread opens a window into the hidden world of business exits, revealing why 80% of entrepreneurs never successfully sell their companies despite having most of their net worth tied up in them. From his first landscaping company at age 15 through multiple six, seven, and eight-figure exits, Goodbread shares the counterintuitive strategies that transform businesses from jobs into valuable assets. Whether you're just starting your entrepreneurial journey or considering your exit strategy after decades in business, this conversation will fundamentally shift how you view your company's potential value and legacy. 

What if your financial knowledge could transform not just your bank account, but your entire life? Join us as we welcome Tim Smith from Aurora Private Wealth, a pioneer in the investment world since 1985, who shares his inspiring journey from overcoming personal financial challenges to leading a nationwide advisory firm. Delve into Tim’s insights on investment strategies, with a focus on ETFs and the impact of groundbreaking technologies like DeepSeek AI in China. With financial literacy as a recurring theme, we question why such a vital life skill isn't prioritized in education, and address the broader implications this has on economic well-being. Tune in for insights, inspiration, and the potential for collaboration as we explore the intersection of finance, technology, and education.

What really goes on behind the curtain of state politics, and how does it affect the real estate market? Maryland's own Mike Griffith, a seasoned state delegate, joins us to pull back the layers of state government and its complexities. With six years of experience under his belt, Mike offers insightful commentary on his legislative duties and his commitment to aiding constituents with governmental challenges. We promise that by the end of this episode, you'll have a newfound appreciation for the nuanced role of state delegates and the tangible impact they have on communities. Our engaging discussion weaves through the intricacies of Maryland's legislative process, exploring how political decisions reverberate through industries like real estate, and the broader economic landscape. This episode is your ticket to understanding not just the headlines, but the undercurrents shaping state policy and how they directly affect everyday citizens and businesses. 

As we welcome Chase as part of our newest member on the show, we discuss the secrets to mastering real estate networking, orchestrating events, and conquering Maryland's property investment scene. But it's not all business— we embrace the balance between work and life as we share personal stories of goal setting and fitness achievements. From preparing for an Ironman race to fun nights out with a different twist, we promise this episode will leave you inspired and ready to tackle both personal and professional milestones. 

Discover how Jet Hennigan transformed Dreamers Event Rentals from a modest family venture into a thriving enterprise. By facing challenges head-on, including skill gaps and differing visions, Jet leveraged financial strategies and robust marketing systems to propel the company forward. This episode unpacks the evolution of the business, from its humble beginnings to a large-scale operation, and the pivotal role of debt in fueling business expansion. Jet doesn't just stop at tents and tables. He ventures into real estate, bravely tackling analysis paralysis and working through the intricacies of the BRRRR strategy. With mentorship and networking at the core of his story, Jet reveals the power of having the right advisors and the essential leap from theory to real-world experience.