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Path To Passive: Real Estate Investing For Technology Professionals
Steven Arita
111 episodes
12 hours ago
Send us a text 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 1...
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Investing
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All content for Path To Passive: Real Estate Investing For Technology Professionals is the property of Steven Arita and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Send us a text 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 1...
Show more...
Investing
Education,
Business,
Careers,
How To
Episodes (20/111)
Path To Passive: Real Estate Investing For Technology Professionals
#110 - What a 1031 Exchange Is — And How It Can Save You Thousands in Taxes with Jonathan Hilley
Send us a text 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 1...
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1 week ago
55 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#109 - Private Placement Memorandum (PPM) for Beginners — What Every New Investor Should Know
Send us a text Ever open a thick investment packet and think, “Yeah… not reading all that”? You’re not the only one. In this episode, Steven breaks down the Private Placement Memorandum, or PPM, that long, legal-looking document most new investors ignore (but really shouldn’t). If you’re in tech and starting to look at private real estate deals, funds, or syndications, this episode will show you what actually matters in a PPM, what to watch out for, and how to tell if a deal makes sense for y...
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2 weeks ago
12 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#108 - How to Build a 1000+ Unit Real Estate Portfolio While Working Full-Time with Christopher Lento
Send us a text What if the landlord you’re renting from sparks your path to financial freedom? That’s exactly what happened to Christopher Lento, a mechanical engineer turned real estate investor who now manages over 1,000 units. In this episode, Chris walks us through his 10+ year journey, starting from house hacking in Boston to building EM Capital and raising investor money. He shares honest lessons on scaling, managing properties out-of-state, knowing when to leave a W2 job, and what pass...
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2 weeks ago
53 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#107 - How To Earn Passive Income by 'Being the Bank' with Rick and Crystal Rumer
Send us a text Ever wish you could invest in real estate without dealing with tenants, repairs, or late-night calls? In this episode, Rick and Crystal Rumer share how they went from overwhelmed landlords to building a business that brings in steady, passive income, all by “being the bank.” They break down how they buy land and homes, set up notes, and help other investors earn 10–12% returns without the usual real estate stress. If you're a busy tech pro, doctor, or just short on time, this e...
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1 month ago
47 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#106 - Tax Hacks Every Real Estate Investor Should Know with Jason Melillo
Send us a text How do some real estate investors manage to pay little or even no taxes while staying completely legal? In this episode, Steven Arita talks with Jason Melillo, CPA and co-founder of KBKG, about the tax strategies smart investors use to keep more money in their pockets. With 25+ years of experience and billions saved for clients, Jason explains cost segregation, bonus depreciation, 1031 exchanges, and opportunity zones in a way that’s easy to understand. They also cover the new ...
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1 month ago
45 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#105 - How Energy Credits Boost Property Profits and Investor Returns with Charles de Jager
Send us a text What if you found out there’s money sitting on the table? Money that could save your real estate project or put more cash in your pocket? In this episode, Steven talks with Charles de Jager, CEO of Energy Credit Consulting, about how energy incentives can help both developers and investors save big. Whether you're starting a new build or renovating an existing property, Charles explains how smart design choices can lead to major savings, sometimes even million-dollar payouts. H...
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1 month ago
59 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#104 - Why Smart Investors Are Choosing Passive Income in 2025 with Ruben Izgelov
Send us a text Is chasing high returns worth the stress, or is steady, reliable income the real goal? In this episode of Path to Passive, host Steven Arita sits down with Ruben Izgelov, co-founder of WeLend, to talk about why more investors, especially tech professionals, are turning to private lending for consistent monthly cash flow. Ruben shares how he went from high school dropout to successful attorney and fund manager, what changed his thinking about risk, and why private lending could ...
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2 months ago
51 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#103 - Passive Income Through 1031s and DSTs with Ben Carmona
Send us a text What if you could sell your property, skip the big tax hit, and stop dealing with all the hassles of being a landlord? In this episode, Steven chats with Ben Carmona, a financial advisor who’s been helping people do just that for over 20 years. Ben breaks down how strategies like 1031 exchanges and Delaware Statutory Trusts (DSTs) work, and how they can help you keep more of your money, earn passive income, and finally step away from managing real estate yourself. Whether you’v...
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2 months ago
38 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#102 - How to Earn Passive Income Without Being a Landlord with Lindsay Davis
Send us a text What if you could earn steady rental income without ever having to fix a leaky faucet or chase down a tenant? In this episode, Steven chats with Lindsay Davis, CEO of Spartan Invest, as she explains how her team helps busy professionals build real estate income through fully managed, turnkey single-family homes. No landlord duties. No guesswork. Just a clear process that handles everything from buying and renovating the home to managing it long-term. We talk about how they keep...
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2 months ago
1 hour

Path To Passive: Real Estate Investing For Technology Professionals
#101 - How Real Estate Investors Save Thousands with Cost Segregation with Brian Kiczula
Send us a text Most real estate investors don’t realize they could be saving thousands on their taxes. In this episode, Steven chats with Brian Kiczula, founder of Cost Seg Rx, as he shares how cost segregation can help you do just that. He explains what it is, how it works, and why it matters whether you own a single-family rental, an RV park, or anything in between. You’ll also hear what to watch out for when buying or selling, and how tech, including AI, is making this strategy faster and ...
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2 months ago
53 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#100 - What I've Learned from 100 Episodes
Send us a text Ever think about what it’s really like to make 100 podcast episodes? In this special episode, Steven looks back on the journey, from being nervous and over-prepared to finding his rhythm and sharing more of his own story. He talks about what worked, what didn’t, and how letting go of perfection made all the difference. You’ll hear about the feedback that meant the most, the listeners tuning in from around the world, and the beliefs he had to drop along the way. Steven also shar...
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3 months ago
26 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#99 - How to Build Wealth Without Becoming a Landlord with John Casmon
Send us a text What would you do if your company went under, not once, but twice? That’s exactly what happened to John Casmon, and it became the turning point that led him into real estate. In this episode, Steven sits down with John Casmon as he shares how he went from house hacking a duplex to leading over $150 million in multifamily apartment deals. He talks honestly about the fear, the doubt, and what it took to shift from using only his savings to partnering with others through syndicati...
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3 months ago
58 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#98 - Where Does The Money Come From?
Send us a text Ever wonder how investments actually make money? In this episode of the Smart Tech Investor mini series, Steven keeps it simple and walks you through real examples—from apartments and self-storage to retail spaces, warehouses, land development, and more. If you’re in tech or just starting to explore investing, this one’s for you. Steven explains where the money comes from, who’s paying, and how you get your share. It’s all about understanding how each property works and why peo...
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3 months ago
19 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#97 - What Luxury Real Estate Really Means and How to Sell Your Home for More with Debbi DiMaggio
Send us a text Is luxury real estate really just about the price? In this episode, Steven Arita sits down with Debbi DiMaggio, real estate veteran, coach, and author, to unpack what truly defines luxury in today’s market. With over 35 years of experience in the Bay Area, Debbi shares how service, presentation, and emotional connection matter far more than price tags. She talks about working with celebrity clients, guiding sellers through home prep years in advance, and helping buyers find hom...
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3 months ago
1 hour 6 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#96 - How Bitcoin Mining Became a Powerful Passive Income Strategy with Beau Turner
Send us a text What if instead of buying more stocks or another rental, you could earn passive income from a machine that mines Bitcoin while you sleep? In this episode, Steven Arita chats with Beau Turner, founder of Abundant Mines, about how he went from real estate investing to running a full-time Bitcoin mining business after learning some hard and expensive lessons. Beau breaks down what Bitcoin mining really is, how it’s different from just buying Bitcoin, and how it can generate cash f...
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3 months ago
1 hour 9 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#95 - Real Talk on Wealth, Purpose, and Starting Over with Damion Lupo
Send us a text What does it really take to go from feeling lost with money to finally being in control? In this episode, Steven chats with Damion Lupo as he opens up about starting his first business at age 11, losing millions during the 2008 crash, and how those tough lessons shaped the mission he’s on today. He shares why most people stay stuck, what helped him turn things around, and how building wealth is more about mindset and purpose than just dollars. If you're feeling unsure about you...
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4 months ago
53 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#94 - From Fortune 500 to Real Estate Freedom with Niyi Adewole
Send us a text Thinking about getting into real estate but not sure if you need a license, or if you should even invest outside your city? In this episode, Steven chats with Niyi Adewole, a former healthcare executive who left the corporate world to build his dream life through real estate. Niyi shares how he got started with a simple house hack in Louisville, grew a 30-unit portfolio, and later transitioned into short-term rentals in Atlanta, as well as self-storage. He breaks down what new ...
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4 months ago
50 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#93 - Building Real Security Beyond the Stock Market with Patrick Grimes
Send us a text Are your 401K, IRA, and company stock really enough to secure your future? In this episode, Steven Arita talks to Patrick Grimes, a former robotics engineer turned full-time investor, who shares how he went from losing it all in real estate to building real wealth through smart, alternative investments. He talks about the shift from single-family homes to larger apartment deals, and why he now focuses on recession-resistant investments like litigation finance and energy. Patric...
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4 months ago
53 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#92 - How To Think Like A Business Owner In Your Investments
Send us a text What if your money could work harder than you do? In this episode, Steven flips the script on how we think about wealth. Instead of just chasing a bigger paycheck, we’ll talk about the power of ownership and why shifting your mindset can make a huge difference. Steven discusses something called return on effort (ROE) and why it matters just as much as return on investment (ROI). Think of it as approaching your finances like a business owner, not just an employee. Whether you’...
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4 months ago
6 minutes

Path To Passive: Real Estate Investing For Technology Professionals
#91 - How One Nurse Left Healthcare to Become a Full-Time Real Estate Investor with Maria Marks
Send us a text What happens when a nurse shows up to a real estate seminar with an index card full of notes and leaves with a whole new vision for her life? In this episode, Steven Arita chats with Maria Marks, a former nurse who left healthcare to build a real estate business that now gives her steady passive income. Maria opens up about the personal events that led her to start investing, why she skipped single-family homes and went straight into multifamily, and what it really felt like to...
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5 months ago
54 minutes

Path To Passive: Real Estate Investing For Technology Professionals
Send us a text 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 1...