Path To Passive: Real Estate Investing For Technology Professionals

#140 - Business Acquisitions: Faster Cash Flow with David Hori

Send us Fan Mail [https://www.buzzsprout.com/2247837/fan_mail/new] 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 far more sellers than buyers and why that spells a generational opportunity for tech professionals who know how to build and operate teams. You'll learn why buying an existing business beats building a startup from scratch (no product-market fit risk, cash flow from day one), how one business David is actively pursuing generates between $37,000 and $120,000 a month in cash flow — the equivalent of buying 13 rental properties — and why private equity's buy-and-flip playbook is fundamentally broken for communities and long-term wealth. David also shares his two niche buy boxes (e-commerce and water infrastructure), the counterintuitive "stay in your lane" rule that applies to both operators and investors, and the simple revenue levers — vendor renegotiation, bundling, and basic pricing hygiene — that can 3x a business within 12 months. Whether you're a tech professional with capital to deploy or simply curious about alternatives to rental real estate, this episode will change how you think about building passive income and long-term financial freedom. Connect with David: 🔗 LinkedIn: https://www.linkedin.com/in/iamdavidhori/ [https://www.linkedin.com/in/iamdavidhori/] 🌐 Company Website: https://toplineops.com/ [https://toplineops.com/] 📸 Instagram: https://www.instagram.com/toplineops/ [https://www.instagram.com/toplineops/] Weekly Webinar: https://learn.toplineops.com/pod-webinar-1 [https://learn.toplineops.com/pod-webinar-1]  Episode Highlights: 0:35 – Intro 1:36 – David shares his journey from a global law firm to VC-backed startups chasing speed and innovation. 10:26 – $14 trillion with a T is changing hands as baby boomers exit — and not enough buyers exist. 10:27 – Why buying a proven, cash-flowing business beats building a startup from scratch. 10:26 – The 3 D's (Divorce, Death, Disease) — the real reasons business owners sell. 15:03 – Private equity's buy-and-flip playbook is destructive — David explains why he's on the opposite end. 19:47 – One business David is actively bidding on generates $37K–$120K/month in cash flow. 22:23 – Simple levers to 3x revenue: renegotiate vendors, bundle products, and raise your prices. 35:43 – David's mentor kept telling him "stay in your lane" — here's why he finally listened. 35:44 – 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

#139 - Senior Living: Aging Demand, Limited Supply with Radhika Rastogi

Send us Fan Mail [https://www.buzzsprout.com/2247837/fan_mail/new] 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 episode, she breaks down why senior living is a once-in-a-generation opportunity for high-income professionals: the 80+ population is growing 28% over the next four years, the national investment gap sits at $258 billion, and occupancy in many markets is already at 98–99% with wait lists. Radhika explains the three phases of senior housing, how her team acquires underperforming communities for under $100K per unit, and why she interviewed 75 operators before selecting the right regional partners. She also reveals the hidden revenue stream most mom-and-pop sellers miss entirely, level of care fees and how spotting that one gap can transform a deal's returns. For W-2 investors feeling stuck in unscalable residential strategies, this episode is a masterclass in making the shift to commercial real estate syndications — starting with as little as $50K and building lasting wealth without leaving your day job. Connect with Radhika: 🔗 LinkedIn:  https://www.linkedin.com/in/rastogi-radhika/ [https://www.linkedin.com/in/rastogi-radhika/] 🌐 Company Website: https://www.relikcapitalgroup.com/ [https://www.relikcapitalgroup.com/]📰 Podcast: https://podcasts.apple.com/au/podcast/rich-roots/id1795836092 [https://podcasts.apple.com/au/podcast/rich-roots/id1795836092]  Episode Highlights: [0:00] – Intro: Teaser clip — senior living demand is exploding [0:45] – Welcome to Path to Passive [4:19] – The 120-home math that made Radhika pivot from residential [6:04] – Independent living, assisted living & memory care explained [8:38] – $258B investment gap, 28% demand surge & 98% occupancy markets [14:43] – How syndications work & Relik Capital's buy box [15:46] – The hidden revenue stream most mom-and-pop sellers miss [19:49] – Why they interviewed 75 operators to find just 3 [27:36] – AI-powered underwriting: reviewing 30 deals a month [33:46] – How $50K can double every 5 years through syndications [39:29] – 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

#138 - Direct Capital Raising Wins Bigger Investor Checks with Derek Vickers

Send us Fan Mail [https://www.buzzsprout.com/2247837/fan_mail/new] 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 owners on a list he found himself, to launching a $20 million fund — after getting turned down by a friend who told him his $50K wasn't enough to invest.  Spoiler: Derek's response was to go buy the parks himself.  Listeners will learn how Derek applied Grant Cardone's 10X philosophy to real estate acquisitions, why underestimating effort is the #1 reason most people quit before they break through, and how shifting from syndications to a fund model opened the door to million-dollar check writers who actually prefer you to skip the small talk and just ask the direct question.  Derek also breaks down his portfolio aggregation thesis — why he believes there are fewer than 10 years left of mom-and-pop mobile home park deals — and what he's doing now to position for institutional buyers.  Whether you're a W-2 tech professional thinking about passive income through commercial real estate, or you're already a few deals in and wondering how to scale, this conversation is packed with mindset shifts and tactical frameworks you can apply immediately.  By the end of this episode, you'll walk away with a sharper understanding of how to build momentum in mobile home park investing, how to raise capital without being transactional, and why the size of your vision matters less than your willingness to keep moving forward until the light hits. Connect with Derek: 🔗 LinkedIn: https://www.linkedin.com/in/derek-vickers-0774b146/ [https://www.linkedin.com/in/derek-vickers-0774b146/] 🔗 Instagram: https://www.instagram.com/derekvickers885/ [https://www.instagram.com/derekvickers885/] 🔗 Facebook: https://www.facebook.com/derek.vickers.14 [https://www.facebook.com/derek.vickers.14] 🌐 Company Website: https://vicktorycapital.com/home2 [https://vicktorycapital.com/home2]Episode Highlights: 0:32 – Intro: What is Path to Passive and who is it for? 0:56 – Meet Derek Vickers: 2,000+ units, 40+ mobile home park communities, and $130M+ in assets under management. 2:58 – How Derek self-taught real estate underwriting through Grant Cardone's Real Estate Mondays and why the math just clicked for him. 4:04 – The rejection that started it all: A friend said his $50K wasn't enough to invest — so Derek went and bought the parks himself. 7:40 – The 10X mindset shift: Why Derek stopped making 15 calls a day, hired callers, and scaled his outreach to win through sheer volume. 16:53 – Raising capital without being transactional: How belief in your deal removes the fear of asking investors for money directly. 12:19 – From JV deals to syndications to a $20M fund: How Derek's capital structure evolved as he scaled to 40+ parks. 28:59 – Why Derek believes there are fewer than 10 years left of mom-and-pop mobile home park deals — and how he's positioning for institutional buyers. 39:49 – What the version of Derek who couldn't afford a Red Bull would think of everything he's built — family, health, and freedom included. 42:31 – 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

#137 - Structure Over Deals: Real Estate Profit Strategy with Cherif Medawar

Send us Fan Mail [https://www.buzzsprout.com/2247837/fan_mail/new] 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 capital or connections, it started with a $2.25 apple.  Working as a management trainee at the Century Plaza Hotel in Los Angeles (once called the Western White House), Cherif charged a billionaire for an apple at 2 AM instead of comping it — and that single act of integrity got him hired as the man's right-hand man for the next eight years, learning how to manage properties across the globe from Martinique to Paris.  In this conversation, Cherif unpacks the exact framework — strategy, structure, system, automation, scale, and sustainability — that took him from hotel employee to managing a $100M real estate portfolio in Old San Juan, Puerto Rico.  He breaks down the critical difference between syndications and real estate funds, explains why tech professionals are uniquely positioned to build wealth faster than almost anyone else, and reveals why "money is in the structure" — not the deal.  You'll also hear Cherif's personal story of navigating the sudden loss of his wife while managing a multi-jurisdictional estate across three countries, and how he used the same GPS-like framework to rebuild and reach total financial freedom.  Whether you're a software engineer at a FAANG company or a high-earning tech professional ready to stop trading time for money, this episode gives you a clear, actionable path from W-2 income to passive income — without having to become a full-time real estate expert. Connect with Cherif: 🔗 LinkedIn: https://www.linkedin.com/in/cherifmedawar/  🌐 Company Website: https://www.cherifmedawar.com/ 🎥 Youtube: https://www.youtube.com/user/cherifmedawar1  Episode Highlights: [0:39] – Intro [2:16] – How Cherif got spotted by a billionaire at the Century Plaza Hotel — and why charging him $2.25 for an apple launched an 8-year mentorship that changed everything. [11:07] – Cherif reveals why "money is in the structure" — and breaks down the exact Strategy → Structure → System → Automation → Scale → Sustainability framework. [16:58] – Syndication vs. Real Estate Fund explained — why the fund model gives you more flexibility, less risk, and keeps all the upside for you. [18:47] – How to set up a debt fund that pays investors fixed returns of 6–10% while you compound wealth and never have to sell your properties. [32:03] – The Old San Juan single-tenant strategy that generates 10–15 year corporate-guaranteed leases — and how Cherif spotted the opportunity before anyone else. [37:44] – The 3 stages of money every tech professional must move through: work for money, work the money, then — 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

#136 - Delaware Statutory Trusts: A 1031 checklist with Ashley Romiti

Send us Fan Mail [https://www.buzzsprout.com/2247837/fan_mail/new] 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 asset classes are available (multifamily, industrial, net-leased retail, and more), and why these deals are structured to protect capital preservation not chase outsize returns.  You'll learn the difference between a traditional DST exit and a 721 UPREIT strategy for long-term estate planning, how to avoid the costly mistake of waiting until after closing to start your DST planning, and why having options across multiple sponsors matters more than just picking a big name.  Ashley even shares a memorable origin story — from aspiring doctor to social worker to landing at Marcus & Millichap after running the math on a $60K grad school bill for a $28K salary, and the moment she posed for a photo holding $20,000 cash from her very first commercial deal.  Whether you're a tech professional curious about passive real estate income, a landlord exhausted by weekend maintenance calls, or someone mid-exchange with "boot" left over, this episode gives you a clear, jargon-free roadmap to your next move. Connect with Ashley: 🔗 LinkedIn: https://www.linkedin.com/in/ashley-romiti-dst/  🌐 Company Website: https://www.gca1031.com/ 📱 Cellphone#: 9492355606 Ashley Romiti offers securities through Concorde Investment Services, LLC (CIS), member FINRA/SIPC. GCA 1031 is independent of CIS. Concorde is headquartered at 3909 Research Park Drive, Suite 200, Ann Arbor, MI 48108. This podcast is for informational purposes only, does not constitute as investment advice, and is not legal or tax advice. Please consult the appropriate professional regarding your individual circumstance.  Episode Highlights: [0:34] – Intro: What is Path to Passive and who it's for [0:58] – Meet Ashley Romiti: 15-year commercial real estate veteran and founder of GCA 1031 [7:25] – DSTs Explained: What a Delaware Statutory Trust is and why it's the ultimate passive real estate vehicle for tired landlords [23:36] – Critical Mistake: Why you MUST start your 1031 exchange before closing — not after [27:08] – Due Diligence Deep Dive: How to evaluate a DST at the sponsor, property, and trust level [28:56] – Return on Equity Check: How to know when your rental property is no longer worth managing [29:36] – What Is "Boot"? How leftover 1031 exchange funds can be a low-risk way to test a DST investment [35:16] – Pro Tip: Start planning before you list — why early strategy conversations change outcomes [36:32] – Outro: How to connect with Ashley and find resources at GCA1031.com — 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