Path To Passive: Real Estate Investing For Technology Professionals

#129 - US Rentals To Overseas Assets: Diversification with Mike Cobb

Send a textWhat 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 learned to predict tech pricing trends and bid contracts below cost—then turned that "time machine" framework into a real estate investment strategy that's made him millions. Here's the core insight: the developing world isn't like a time machine, it IS a time machine, and different countries represent different points on a development curve you can exploit. Mike walks through how he spotted a market gap financing properties in Belize when no U.S. or Belizean bank would touch foreign buyers, how he turned $100 worth of outlet upgrades into a multi-country development business, and why he believes his timber business will eclipse both his bank and real estate holdings within three years. You'll learn the critical difference between "heart decisions" (lifestyle purchases) and "head decisions" (cashflow investments), why digital nomads have created a rental arbitrage opportunity most investors are ignoring, and how remote work has fundamentally changed international real estate for the first time in human history. Mike shares his "anchovy pizza principle"—invest in what the market wants, not what you want—and reveals why teak being cut 8-10 times faster than it's replanted represents a generational wealth opportunity starting at just $22,000. This isn't hype—it's a thinking conversation about diversification, due diligence, and the shift from "seller beware" to "buyer beware" that trips up most foreign investors. Whether you're exploring global optionality, looking to diversify beyond U.S. markets, or simply curious how high-earning W-2 professionals can leverage international opportunities, this episode delivers a clear framework for evaluating overseas real estate investments without losing your shirt.Connect with Mike:LinkedIn: https://www.linkedin.com/in/michaelkcobb/Website: https://ecidevelopment.com/Mike's giving away his book "How to Buy Your Home Overseas (And Get It Right the First Time)" for free—just email podcast@ecidevelopment.com with subject "Mike's book." Episode Highlights:0:52 – [Intro]3:32 – [Hook Question] What percentage of your investible net worth is actually outside your home country?4:16 – [Mike's Background] From IBM clone manufacturer to international real estate developer across Latin America6:38 – [The $100 Insight] How fixing outlet strips and bathroom lights became a multi-country development business8:30 – [The Time Machine Framework] The developing world IS a time machine—countries represent dif— Share this with your tech friends who you think would benefit from learning about passive income and alternative real estate investments. For more resources and guides, check these out: Crack the Code https://www.aritacapital.com/crack-the-code/ Investor 101 https://www.aritacapital.com/investor-101-resource/ Due Diligence Resource https://www.aritacapital.com/dd-checklist-resource/ If you want to learn more, reach out at: Email: steven@aritacapital.com LinkedIn: https://www.linkedin.com/in/aritasteven/ IG: https://www.instagram.com/the.real.arita

#128 - Banking to Real Estate Tech: Scalable Income with Kevin Shtofman

Send a textWhat 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 agents are screening deals in seconds, comparing actual performance to underwriting models, and even helping solo property managers prioritize emergency maintenance requests based on tenant value and calendar availability. Kevin shares a fascinating story about validation rules like why some leases show zero rent (hint: concession periods) and explains why bad data for reports is merely "not good," but bad data for AI automation is "very, very dangerous." He breaks down the three-tier environment system (dev, QC, production) that prevents AI from acting on garbage data, and reveals how tech professionals building side portfolios can use Claude or Gemini as thought partners to draft lease agreements and financial models before paying attorneys. Kevin also opens up about his leap from a 100,000-employee consulting firm to employee number nine at a start-up, the "intuitive fence" concept that helped him make the jump, and his biggest career skill: learning when and how to say no. Whether you're a W-2 tech professional managing three rental properties or dreaming of scaling to institutional size, this episode shows you exactly how data pipelines, validation rules, and AI collaboration are reshaping real estate investing and how to apply these lessons at any portfolio size. By the end, you'll understand why connecting actuals to underwriting to benchmark data isn't just about better reports—it's your business case for raising the next fund or fixing what's broken before investors notice.Connect with Kevin:LinkedIn: https://www.linkedin.com/in/kevinshtofman/ Website: https://cherre.com/ Episode Highlights:0:00] – Intro[9:06] – What Cherry does: Real estate data warehouse connecting all your systems into one standardized model[17:36] – Why data lineage matters: How to prove your dashboard is right when executives say "this can't be correct"[20:50] – The three-environment system: Dev, QC, and production prevent AI from acting on bad data[26:22] – Why tech and business teams must collaborate: One plus one equals seven with AI in the mix[29:43] – AI as your executive assistant: Prioritizing maintenance tickets, drafting communications, and syncing with your day job calendar[33:10] – The ideal Cherry client: Why 2,000 units or 1M sq ft is the sweet spot, plus free tools for smaller portfolios[39:24] – Actuals vs underwriting vs benchmark: The ROI-driven use case that either ra— Share this with your tech friends who you think would benefit from learning about passive income and alternative real estate investments. For more resources and guides, check these out: Crack the Code https://www.aritacapital.com/crack-the-code/ Investor 101 https://www.aritacapital.com/investor-101-resource/ Due Diligence Resource https://www.aritacapital.com/dd-checklist-resource/ If you want to learn more, reach out at: Email: steven@aritacapital.com LinkedIn: https://www.linkedin.com/in/aritasteven/ IG: https://www.instagram.com/the.real.arita

#127 - Oil Wells: Accelerated Capital Recovery with John Engel

Send a textWhat 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 one. You’ll hear the difference between high-risk “wildcat” drilling and proven field development, how long wells can produce, what decline curves mean, and what red flags to watch for. If you are a high-income earner looking for passive income and meaningful tax relief, this episode gives you a practical look at how it all works.John Engel is the Chief Operating Officer of Gulf Coast Western, a Dallas-based oil and gas company focused on the exploration, development, and acquisition of domestic energy reserves. In his role, he oversees operations and works closely with partners and investors involved in the company’s joint venture drilling projects. Engel is known for emphasizing transparency, disciplined project selection, and long-term business relationships within the energy sector. He frequently speaks about oil and gas investing, including topics such as cash flow potential, tax advantages, and risk management in field development projects. His leadership centers on aligning operational performance with investor expectations while maintaining a strong presence in established U.S. oil and gas regions.Connect with John:Website: https://www.gulfcoastwestern.com/Episode highlights:(0:00) Intro(0:48) How the oil and gas partnership model works(3:31) Major tax benefits and depletion allowance(6:54) Why oil and gas demand is still strong(15:15) Proven fields vs. exploratory drilling(25:26) The investment hold period(30:53) How long wells produce and decline curves(34:14) Return targets and capital payback(39:12) Year-one write-offs and reinvestment strategy(42:34) Common mistakes and investor red flags(48:43) Outro— Share this with your tech friends who you think would benefit from learning about passive income and alternative real estate investments. For more resources and guides, check these out: Crack the Code https://www.aritacapital.com/crack-the-code/ Investor 101 https://www.aritacapital.com/investor-101-resource/ Due Diligence Resource https://www.aritacapital.com/dd-checklist-resource/ If you want to learn more, reach out at: Email: steven@aritacapital.com LinkedIn: https://www.linkedin.com/in/aritasteven/ IG: https://www.instagram.com/the.real.arita

#126 - Asset-Backed Leverage: Durable Cash Flow with Joe Edgar

Send a textWhat 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 simplicity. If you earn well but feel stuck on a treadmill, this conversation will hit home. Learn how to let your money work harder than your time and build steady, lasting wealth.Joe Edgar is an entrepreneur, investor, and technology founder known for his early start in real estate and his focus on scalable business models. He purchased and renovated his first property at just 14 years old, building a foundation in real estate that later expanded into lending, angel investing, and venture capital. Over time, he founded and led multiple technology platforms, including property management software and the local commerce rewards app Loca. Edgar has also worked with government-backed investment programs and venture funds, bringing a strong perspective on capital allocation and startup growth. Often calling himself a “lazy entrepreneur,” he promotes building systems that create leverage, passive income, and long-term value rather than trading time for money.Connect with Joe:Website: ​​https://loca.us/LinkedIn: https://www.linkedin.com/in/joseph-edgar-7a018521/ X: https://x.com/Joe_Edgar_ YT: https://www.youtube.com/channel/UC5Nyvxy-oCht0PX_sELkslgEpisode highlights:(0:00) Intro(2:40) Meet Joe Edgar(5:18) Buying a house at 14(13:35) Australia and cultural lessons(20:02) Why lifestyle inflation keeps people stuck(24:45) Lifestyle vs scalable entrepreneurs(28:30) The vision behind Loca(42:44) Connecting local businesses with real estate ecosystems(52:20) Venture capital and fund of funds explained(1:09:21) Investment strategies: Real Estate vs. Venture Capital(1:19:47) The importance of home ownership and passive income(1:30:12) Navigating investment choices(1:44:42) Where to find and learn more about Joe and his resources(1:45:25) Outro— Share this with your tech friends who you think would benefit from learning about passive income and alternative real estate investments. For more resources and guides, check these out: Crack the Code https://www.aritacapital.com/crack-the-code/ Investor 101 https://www.aritacapital.com/investor-101-resource/ Due Diligence Resource https://www.aritacapital.com/dd-checklist-resource/ If you want to learn more, reach out at: Email: steven@aritacapital.com LinkedIn: https://www.linkedin.com/in/aritasteven/ IG: https://www.instagram.com/the.real.arita

#125 - Resident Experience Systems: Predictable Investor Returns with John Makarewicz

Send a textWhat 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 builds high-performing teams across multiple markets. If you’re a high-income tech professional weighing DIY rentals versus passive investing, this conversation will give you clarity and confidence.John Makarewicz is an experienced entrepreneur and real estate operator, currently serving as President and Managing Partner of Ferris Capital Partners. He specializes in multifamily real estate investing, focusing on acquiring and improving apartment communities to create strong returns for investors while delivering an exceptional living experience for residents. Prior to Ferris Capital, John served as President of Mark Spain Real Estate, where he helped scale the company significantly and played a key role in its growth and eventual private equity exit. Throughout his career, John has been known for his focus on systems, leadership, culture, and operational discipline, building teams that execute at a high level and drive long-term value.Connect with JohnWebsite: https://www.fariscapitalpartners.com/LinkedIn: https://www.linkedin.com/in/john-makarewicz-23589a37/Instagram: https://www.instagram.com/john_makarewicz/Episode highlights:(0:00) Intro(3:06) John’s background and private equity exit(7:28) Systems and operational discipline(10:33) Identifying his role in the business(20:17) Target markets and investment strategy(24:36) Resident-first philosophy(26:56) Building culture through daily fundamentals(33:45) The 1-3-5 goal-setting framework(44:49) Passive investing vs. DIY rentals(53:59) Books, learning, and long-term growth(55:45) Where to find John and his team(56:49) Outro— Share this with your tech friends who you think would benefit from learning about passive income and alternative real estate investments. For more resources and guides, check these out: Crack the Code https://www.aritacapital.com/crack-the-code/ Investor 101 https://www.aritacapital.com/investor-101-resource/ Due Diligence Resource https://www.aritacapital.com/dd-checklist-resource/ If you want to learn more, reach out at: Email: steven@aritacapital.com LinkedIn: https://www.linkedin.com/in/aritasteven/ IG: https://www.instagram.com/the.real.arita