Path To Passive: Real Estate Investing For Technology Professionals

40 Episodes
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By: Steven Arita

Welcome to "Path To Passive: Real Estate Investing for Tech Professionals," the podcast that helps tech-savvy individuals secure their financial future through real estate. In the fast-paced world of technology, it's easy to overlook the power of real estate as a source of passive income. This podcast is here to change that.In each episode, we'll break down real estate investment strategies in plain language, tailored to tech professionals like you. We'll cover topics like how to use your tech skills to make data-driven property decisions, generate passive income, manage risks, and maximize tax benefits. Plus, you'll hear inspiring success...

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Land Development Without Becoming the Builder with Brandon Cobb
Last Friday at 7:00 PM

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What you won't learn in a W-2 job is that your financial security is entirely in someone else's hands  until the day your boss calls you into a Starbucks and fires you on what felt like your best day ever. 

That's exactly what happened to Brandon Cobb, a former medical device sales rep who went from Rookie of the Year to unemployed in one conversation, and used that gut-punch moment to build a land development company now doing $20 million a year. 

In this episode of Path to Passive, hos...


Coffee Farms as an Alternative Asset with Adam Jason
07/24/2026

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What if the coffee you drank this morning was actually a pre-IPO investment opportunity?

On this episode of The Path to Passive, host Steven Arita sits down with Adam Jason, co-CEO of Green Coffee Company and former Wall Street securities attorney who traded courtrooms and IPO filings for coffee farms in MedellĂ­n, Colombia.

Adam shares the unexpected story of how a spontaneous month-long trip turned into building Colombia's largest coffee producer, 10,000 acres, 10 million trees, and over $100 million raised from accredited US investors.

You'll learn how A...


Start With Better Real Estate Partners with Victor Menasce
07/17/2026

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What you don't know about real estate partnerships could be costing you years of your investing career and Victor Menasce learned that the hard way. 

On this episode of The Path to Passive, host Steven Arita sits down with Victor Menasce, former VP of Engineering at a semiconductor company, serial M&A dealmaker, author of Magnetic Capital, and now senior partner at Y Street Capital and host of the Real Estate Espresso podcast with over 3,000 episodes. 

Victor brings a rare systems-thinking lens to commercial real estate investing, one th...


Systematizing Mobile Home Park Profits with Chad Freeman
07/10/2026

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What if your W-2 paycheck is the biggest thing standing between you and real wealth?

Host Steven Arita sits down with Chad Freeman — airline pilot, mobile home park operator, and commercial real estate investor with over a decade in the game to unpack one of the most overlooked asset classes for tech professionals.

Chad's origin story is hard to beat: he discovered mobile home parks after spotting a Frank Rolfe boot camp manual at his business partner's mother's house, took the course five times, bought his first parks in...


Multifamily Scale Without Rental Headaches with Ryan Porter
07/03/2026

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What if your W-2 salary is your biggest financial liability? 

In this episode of Path to Passive, host Steven Arita sits down with Ryan Porter — AWS Principal Cloud Architect, real estate investor, and co-founder of Porter Legacy Group — to unpack how a tech professional with 14 years of investing experience went from rehabbing a "seventies cocaine den" condo in San Francisco's Mission District to buying a 147-unit multifamily asset in Dallas-Fort Worth at a 30% discount straight from the bank. 

Ryan shares how he scaled from single family midterm rentals in Med...


Vet Sponsors Before Wiring Capital with Ken Gee
#144
06/26/2026

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There are four rules that every passive investor must use to vet a real estate sponsor — and if you skip them, you're gambling with your money. 

In this episode of Path to Passive, host Steven Arita sits down with Ken Gee, CPA, former Deloitte real estate tax advisor, Founder and managing member of KRI Partners, a private equity firm on its sixth multifamily fund with a track record spanning decades. 

Ken built his career watching high-net-worth clients quietly compound wealth through real estate while he worked 80-hour weeks at D...


Why Income Funds Beat the 4% Rule with Jay Patel
06/19/2026

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What if the retirement strategy your money manager swears by is already 30 years out of date — and quietly draining your future? 


In this episode of The Path to Passive, host Steven Arita sits down with Jay Patel, serial entrepreneur, former hedge fund manager, and the visionary building India's first MLS, to unpack a smarter path to retirement wealth for W-2 tech professionals. 


Jay shares how a $2.5 million loss from September 11th — at just 30 years old — completely rewired the way he t...


Private Money Beats Bank Financing with Jay Conner
06/12/2026

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What if the funding strategy that saved one real estate investor's entire business during the 2008 financial crisis could also help you grow your wealth passively — without touching the stock market?

In this episode of Path to Passive, host Steven Arita sits down with Jay Conner, a seasoned real estate investor who has rehabbed and flipped over 500 houses in Eastern North Carolina and built a seven-figure business using a little-known strategy called private money lending.

Jay's story starts with a gut punch: in January 2009, he called his banker to fu...


Infinite Banking: Keep Capital Compounding with Anthony Faso & Cameron Christiansen
06/05/2026

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What if the secret weapon the Rockefellers used to build generational wealth — and that most W-2 tech professionals have never heard of — was sitting inside a whole life insurance policy this whole time?

In this episode of Path to Passive, host Steven Arita sits down with Anthony Faso and Cameron Christiansen, co-founders of Infinite Wealth Consultants and practitioners of the Infinite Banking Concept (IBC) for nearly two decades. Anthony, a recovering CPA, and Cameron, who went from managing 60 caddies in Las Vegas to designing custom wealth-building policies, break down IBC from...


Business Acquisitions: Faster Cash Flow with David Hori
05/29/2026

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What if the biggest wealth-building opportunity of the next decade isn't real estate — it's buying the business next door?

In this episode of Path to Passive, host Steven Arita sits down with David Hori, a 25-year veteran of scaling high-growth companies including a Toyota acquisition and multiple VC-backed startups, who has now turned his sights on a different kind of asset: profitable, cash-flowing Main Street businesses.

David breaks down the $14 trillion "Silver Tsunami" — the massive wave of baby boomer business owners who will exit in the next 10 years, with...


Senior Living: Aging Demand, Limited Supply with Radhika Rastogi
05/22/2026

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Most W-2 professionals assume building wealth means buying more homes, Radhika Rastogi did too, until she sat in her garage during COVID and did the math.

Radhika Rastogi is the Co-Founder and Managing Partner of Relik Capital Group, a private equity firm specializing in senior living real estate syndications.

With over 10 years of real estate investing experience, a background leading strategic initiatives for Fortune 100 companies, and deep expertise in Medicaid-funded healthcare programs, she now oversees a portfolio of 300+ senior housing units valued at $17 million.

In this...


Direct Capital Raising Wins Bigger Investor Checks with Derek Vickers
05/15/2026

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What if the key to building a $130M real estate portfolio wasn't a Wall Street background — but pure, relentless persistence from a small-town kid who once had to choose between a 20-oz and an 8-oz Red Bull because he couldn't afford both?

In this episode of Path to Passive, host Steven Arita sits down with Derek Vickers, mobile home park investor, fund manager, and operator of over 2,000 units across 40+ communities. 

Derek shares the raw, unfiltered story of how he went from selling insurance and cold-calling mobile home park own...


Structure Over Deals: Real Estate Profit Strategy with Cherif Medawar
#137
05/08/2026

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Your W-2 salary is a great start, but it was never designed to build the kind of wealth that lets you step back and live life on your own terms. 

In this episode of Path to Passive, host Steven sits down with Cherif Medawar — a real estate investor, fund manager, and educator with 35+ years of experience. He has completed hundreds of transactions and built a $100M+ portfolio across the U.S. and Puerto Rico, including historic commercial assets in Old San Juan. 

Cherif's path to passive income didn't start with...


Delaware Statutory Trusts: A 1031 checklist with Ashley Romiti
05/01/2026

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If you're a W-2 tech professional sitting on a rental property you're tired of managing, this episode is your exit strategy. 

Host Steven Arita sits down with Ashley Romiti, president and founder of GCA 1031 and a 15-year commercial real estate veteran, to break down Delaware Statutory Trusts (DSTs): the powerful but under-the-radar tax strategy that lets real estate investors sell their properties, defer capital gains taxes through a 1031 exchange, and step into fully passive institutional-grade investments. 

Ashley explains exactly how DSTs work as replacement properties in a 1031 exchange, what as...


Tax Liens vs Rentals: Higher Returns Less Management with Brian Seidensticker
04/24/2026

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What if the most overlooked real estate investment strategy has been hiding in plain sight at your local courthouse? 

In this episode of Path to Passive, host Steven Arita sits down with Brian Seidensticker, aerospace engineer turned entrepreneur, founder of Tax Sale Resources, and co-founder of Mount North Capital — to pull back the curtain on tax lien and tax deed investing for W-2 tech professionals looking to build passive income outside the stock market. 

Brian shares how he stumbled into this niche the hard way: after gett...


Multifamily Income Caps, Businesses Scale Revenue with Reed Goossens
#134
04/17/2026

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What if the key to building real wealth isn't quitting your W-2 job — it's using it as a strategic launchpad?

In this episode of Path to Passive, host Steven Arita sits down with Reed Goossens, Australian-born real estate entrepreneur, syndicator, and author of Investing in the U.S., who has scaled from a single triplex to over 1,000 units syndicated through his firm RSN Property Group. 

Reed shares the mindset shifts, identity breakthroughs, and tactical pivots that took him from structural engineer to full-time investor — and how his visa status actua...


Match Capital with Operators, Reduce Deal Risk with Joe Downs
#133
04/10/2026

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What's hiding in plain sight in your own backyard could be the commercial real estate opportunity most W-2 tech professionals have never considered. 

In this episode of Path to Passive, host Steven Arita sits down with Joe Downs, founder of Belrose Group who went from owning a bar to building a portfolio of 20-plus self-storage facilities and pioneering an entirely new asset class called pro storage. 


Joe breaks down why the explosive growth of e-commerce — think Amazon losing 25% of sales if they can't deli...


Cap Rate Spread: Safer Real Estate Leverage with Mike Zlotnik
#132
04/03/2026

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If you're a W-2 tech professional wondering why your stock portfolio feels like a rollercoaster with no seatbelt, this episode is going to change how you think about building real wealth. 

Host Steven Arita sits down with Mike Zlotnik — chess master, former software engineer, fund manager at TF Management Group, and the man behind BigMikeFund.com — who traded midnight software deployments for what he calls "asymmetric return opportunities" in private real estate. 

In this conversation, Mike breaks down exactly why private real estate investing offers something the stock market simply...


SPVs: Predictable Passive Investing with Jeremy Neilson
#131
03/27/2026

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If you thought investing in private deals was only for people with hundred-million-dollar venture funds and a team of lawyers on speed dial — this episode will change that. 

In this conversation on the Path to Passive podcast, host Steven Arita sits down with Jeremy Neilson, an attorney-turned-private-asset-investing specialist who has personally closed nearly 9,000 SPVs, processed over 10,000 tax returns, and helped onboard upward of 300,000 investors since getting a cold call from a 6-person AngelList in 2013 — while pushing his kid on a backyard swing. 

Jeremy breaks down exactly what a special purpos...


Mobile Home Parks: Recession-Proof Cash Flow with Leo Young
#130
03/20/2026

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What if your next investment had a waitlist of tenants, constrained supply, and cash flow that holds up even when the economy doesn't? 

In this episode, Steven Arita sits down with Leo Young, founder of Cornell Communities and former top performer at Tesla, to break down exactly why mobile home parks (manufactured housing communities) are one of the most overlooked passive income vehicles for tech professionals today. 

Leo walks through the three-part investment thesis that changed his thinking — recession-resistant demand, government-constrained supply, and operational arbitrage that most individual owners leav...


US Rentals To Overseas Assets: Diversification with Mike Cobb
#129
03/13/2026

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What percentage of your investible net worth is actually outside your home country? 

If you're like most tech professionals, the answer is "basically zero" and you might be missing one of the smartest diversification plays available. 

In this episode of Path to Passive, Steven Arita sits down with Mike Cobb, CEO of ECI Development, who's spent over 25 years developing resort communities, running a bank, and building a teak timber empire across Latin America. 

Mike started his career in the IBM clone business in the 1980s, where he lea...


Banking to Real Estate Tech: Scalable Income with Kevin Shtofman
#128
03/06/2026

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What if AI could finally make real estate data actually useful instead of overwhelming? 

In this episode of Path to Passive, Steven Arita sits down with Kevin Shtofman, Global Head of Alliances and Corporate Development at Cherre, a real estate data warehouse platform serving insurance companies, sovereign wealth funds, and REITs. 

Kevin brings over 20 years of experience from investment banking, Morgan Stanley, EY, and Deloitte, and he's now helping real estate companies turn fragmented data from acquisitions, leasing, accounting, and reporting into actionable intelligence. 

You'll learn how AI...


Oil Wells: Accelerated Capital Recovery with John Engel
02/27/2026

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What if part of the money you send to the IRS each year could instead be working for you in oil wells? In this episode, Steven welcomes John Engel, COO of Gulf Coast Western, for a clear and honest conversation about oil and gas investing. John explains how investors can participate in packaged wells that generate monthly cash flow, often to return initial capital in 18 to 24 months, depending on the project. They also talk through the real tax advantages, including the ability to write off a large portion of the investment in year...


Asset-Backed Leverage: Durable Cash Flow with Joe Edgar
02/20/2026

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What if the secret to building real wealth isn’t working harder, but getting smarter about ownership and leverage? In today’s episode, Steven chats with entrepreneur and investor Joe Edgar as he shares how calling himself a “lazy entrepreneur” actually helped him win. From buying his first fixer-upper at 14 to building tech platforms and launching Loca, Joe breaks down the difference between income, ownership, and systems that work without you. He shares lessons from real estate, venture capital, and time spent with Aboriginal communities in Australia that shaped his views on money and simp...


Resident Experience Systems: Predictable Investor Returns with John Makarewicz
02/13/2026

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What if the real key to strong investor returns isn’t focusing on investors first, but creating an amazing living experience for residents? In this episode, Steven sits down with John Makarewicz, President of Ferris Capital Partners, to break down what operator-level thinking truly means. John shares his journey from early struggles in college to building and exiting a major real estate company, and how clear systems, strong culture, and disciplined execution drive long-term results. He explains his simple 1-3-5 framework for goal setting, why resident experience fuels investor success, and how he...


The Hidden Formula Behind Profitable Self-Storage with Jacob Vanderslice
02/06/2026

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What actually makes money in self-storage, and why do smart people still get it wrong? In this episode, we sit down with Jacob Vanderslice, co-founder and principal at VanWest Partners, for an honest, operator-first conversation about how these businesses really work. Jacob shares how pricing and revenue decisions happen day to day, why his team walked away from REIT management to run everything in-house, and how small choices add up to real NOI growth. We also talk about real risks investors should pay attention to right now, including new supply, local market pressure...


How the Rich Really Invest: From Startup Exit to Smart Wealth with Tad Fallows
01/30/2026

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What really happens after a big startup exit, and how do the ultra-wealthy actually decide where to put their money? In this episode, Steven chats with Tad Fallows, Managing Director of Long Angle, as he shares what he learned after selling his bootstrapped SaaS company and suddenly facing the question: “What do I do with all this capital?” Tad opens up about the challenges of wealth management, what most people get wrong about investing, and why he built Long Angle, a private community for first-generation wealth creators and execs looking for honest, no-sales conv...


From Flips to Notes: Predictable Cash Flow with Fuquan Bilal
01/23/2026

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What happens when the market crashes, you lose everything, and you have to start all over again? In this episode, Stephen Arita sits down with Fuquan Bilal, a real estate investor who’s been in the game for 26 years and has seen it all. From flipping hundreds of homes before 2008, to bouncing back through the world of mortgage notes, and now focusing on multifamily rentals and luxury spec homes, Fuquan shares the mindset shifts and lessons that helped him reinvent himself again and again. He opens up about what real estate taught him ab...


From Couch to Cash Flow: A Step-by-Step Guide to Passive Investing with Melissa Nash
01/16/2026

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Can you really build wealth through rental properties without ever setting foot in them? Melissa Nash says yes, and she’s done it. In this episode, Melissa shares how she built a 7-figure rental portfolio entirely out-of-state, all while living in California and raising four kids. She breaks down what passive investing actually looks like when you still want ownership and control. From choosing landlord-friendly markets to building reliable teams and using smart financing options like DSCR loans, Melissa walks through her step-by-step system for turnkey real estate success. Whether you're looking to re...


The Hidden Fees Quietly Killing Your Investment Returns with Robert Rolih
01/09/2026

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Are hidden fees eating away at your investment returns? In this episode, Steven Arita sits down with Robert Rolih, author of The Million Dollar Decision, to talk about what really hurts long-term investors, and it’s not just the market. Robert shares how even a small 1% fee can quietly cost you hundreds of thousands (or more), why short-term trading usually backfires, and how you can build a simple, hands-off portfolio with just a couple of ETFs. Whether you’re focused on real estate or looking to clean up your stock market game, this epis...


The Cash Flow Formula for Real Financial Freedom with Chris Miles
01/02/2026

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What if everything you’ve been told about retirement is wrong? In this episode, Steven sits down with Chris Miles, also known as the “anti-financial advisor,” as he shares how most traditional financial advice keeps people stuck, even those doing all the “right” things. He opens up about watching his own dad follow the system only to retire on a tight budget, and why he walked away from his job as a financial advisor to build real, passive income instead. Chris breaks down how you can stop chasing net worth and start building income tha...


Holiday Goals That Actually Stick: A Calm, Clear Way to Plan Your Next Year
12/26/2025

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What if the best time to think about your goals is not when you are rushing into a new year, but when things finally slow down? In this holiday episode, Steven talks about setting goals from gratitude instead of pressure. When work eases up and life feels a little quieter, it is easier to step back and think about what actually matters to you. We walk through a simple goal-setting process you can come back to anytime, one that focuses on the kind of person you want to become, not just the boxes...


What the Wealthy Know That You Don’t: How Smart Money Really Invests with Mark Miller
12/19/2025

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What if you could learn how the Hilton family invests, and apply some of those same strategies to your own money, even if you're not a millionaire? In this episode, Steven Arita chats with Mark Miller, co-founder of Hilton Tax and Wealth Advisors. Mark has spent decades working with the Hilton family office, and now he’s on a mission to bring those smart money principles to everyday investors. They talk about how wealthy families protect and grow their money, how retail investors are being steered wrong, and what you can do differently, ev...


Stop Chasing Rentals: The Real Estate Strategy That Actually Works with Lane Kawaoka
12/12/2025

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How does someone go from being an overworked civil engineer to building a $2 billion real estate portfolio? In this episode, Steven sits down with Lane Kawaoka as he shares his surprisingly relatable story. Lane breaks down how one simple rental in Seattle led to a whole new way of thinking about money, freedom, and how tech and engineering pros can get ahead faster by doing things differently. We talk about his Wealth Elevator framework, how to avoid the trap of traditional investing advice, and why buying one rental at a time might not...


From Dry Cleaning to Passive Income with Ian Noble
12/05/2025

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What does it take to walk away from a 14-year-old business and fully commit to passive real estate investing? In this episode, Steven chats with Ian Noble, founder of RunSteady Investments, as he shares how he scaled a 14-location service business in Austin, led 90+ employees, and ultimately exited in 2023. Now fully focused on helping others invest passively in real estate funds, like mobile home parks and private credit, Ian breaks down what he looks for in deals, why partnerships matter, and the shift from “doing it all” to trusting others with your capital. He a...


The Thanksgiving Episode
11/28/2025

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What if gratitude wasn’t just a “feel-good” exercise, but the key to seeing your life clearly? In this personal and real episode, Steven opens up about the kind of gratitude that actually means something, not the checklist kind, but the type that comes from lived experiences, growth, pain, and the people who showed up along the way. He shares what he's most thankful for this year: from his health and family to early job breaks, the wild ride at Amazon, his relationship, and the raw challenges that shaped him. If you’re growth-m...


LLCs for Tech Pros: Protect Your Real Estate Today with Garrett and Ted Sutton
11/21/2025

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Think your W-2 income is safe once you invest in real estate? Think again. In this episode, Rich Dad Advisors Garrett and Ted Sutton join Steven to break down exactly how tech professionals can protect their assets before problems happen. From the right way to use LLCs, to why insurance alone isn’t enough, this father-son legal team shares clear, practical strategies every investor should know. Plus, hear about their upcoming financial education projects, including a law book for teens, narrated by a golden doodle. Whether you own one rental or ten, this ep...


From Tech Layoffs to Land Profits: Building Freedom Through Real Estate with Mike Deaton
11/14/2025

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What would you do if your high-paying tech job suddenly disappeared? In this episode, Steven chats with Mike Deaton, who shares how getting laid off, alongside his wife, became the moment that changed everything. With no real estate background and a $1,000 land course collecting dust, they took a chance on land investing. Today, that business gives them steady income, control of their time, and a life they love in the Colorado mountains. Mike breaks down how they got started, what it really takes, and how you can build your own safety net before...


Your First Look at a Deal: The Pitch Deck
11/07/2025

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Ever seen one of those picture-perfect hotel ads and thought, “Wow, I wish I was there”? That’s kind of what a real estate pitch deck is like; it looks amazing and full of promise. But what’s really inside? In this episode, Steven breaks down what you’ll actually find in a multifamily real estate pitch deck. He goes over what’s real, what’s just marketing, and what to look out for before you invest. If you’ve ever felt unsure about what you’re looking at or didn’t know what to ask, this ep...


What a 1031 Exchange Is — And How It Can Save You Thousands in Taxes with Jonathan Hilley
10/31/2025

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What if you could legally keep up to 40% of your profits when you sell real estate, and most people don’t even know it’s possible? In this episode, Steven chats with Jon Hilley, aka “Mr. 1031,” to talk about one of the biggest tax-saving moves in real estate: the 1031 exchange. Jon explains what it is, how it works, and why more investors should be using it. He also shares his own story, from working at Goldman Sachs to running cannabis companies to now leading one of the top 1031 exchange firms in the country. You’ll a...