Real Estate Investing Made Predictable: Financial Freedom With Tech | Jake & Gino Podcast

Every successful founder has a story worth learning from. In this episode, Jake & Gino sit down with Brian Smith to unpack his incredible entrepreneur journey—from surviving political challenges in Denver real estate to building and scaling businesses across the U.S. and Mexico.Brian shares candid lessons on entrepreneurship, resilience, and growth. Discover how his early days in commercial real estate shaped his mindset, why burnout forced him to pivot, and how he eventually launched Strategy Ladders to help founder-led B2B service businesses scale beyond the owner. You’ll also hear his perspective on Mexico City as an entrepreneurial hub, the shift from consulting to implementation, and how he helps businesses achieve 2–8X growth. If you’re an entrepreneur or investor, you won’t want to miss Brian’s insights.Connect with Brian Smith: StrategyLadders.com | LinkedIn: S. Brian Smith Chapters:00:00 – Introduction03:12 – Breaking into Denver real estate with master leases07:39 – Politics, burnout, and lessons from failure14:43 – Redefining success: survivalist roots to investment banking20:24 – Founders Organization & why many groups miss real entrepreneurs32:52 – Myths vs. reality of living in Mexico as an entrepreneur42:45 – Why implementation beats coaching in today’s consulting market We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

What’s the best Multifamily Investing Strategy for your goals? Gino Barbaro reveals how to stop chasing IRR and start building a plan that matches your time, capital, and risk—so you can grow cash flow and options.In this episode, Gino outlines a practical roadmap: set clear goals (extra income, retirement timeline, job optionality, tax planning), pick the right vehicle (syndication, JV, or creative financing), and reinvest early gains while keeping your day job to build equity. You’ll learn how seller financing and strong partners can bridge capital gaps, why “Buy Right, Manage Right, Finance Right” is the durable framework, and how to weigh tax benefits without letting them drive the deal. We also compare syndication vs. JV and when each supports your Multifamily Investing Strategy. By the end, you’ll know how to align deals with outcomes and use a repeatable Multifamily Investing Strategy to scale cash flow, equity, and long-term wealth.Connect with Gino Barbaro: [email protected] | wheelbarrowprofits.com We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Most investors chase deals but never keep the profits. In this episode, David Richter, author of Profit First for Real Estate Investing and founder of Simple CFO, reveals how the Profit First Real Estate Investing system helps you build lasting profitability and stop living deal to deal.You’ll learn why most entrepreneurs fail financially, how to flip the traditional “sales – expenses = profit” formula, and why paying yourself first changes everything. David breaks down the “golden trio” bank accounts, case studies of investors who turned losses into profits, and how to scale a business with clarity and confidence. If you want financial control, less stress, and more freedom, this conversation on Profit First Real Estate Investing is essential.Connect with David Richter: https://simplecfo.com Chapters: 00:00 – Introduction02:23 – The Profit First formula explained10:09 – Playing the money game as an entrepreneur13:48 – The “Golden Trio” bank accounts for clarity21:04 – Case study: turning $70k losses into $70k giving28:55 – Growth vs. scaling: understanding the difference We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Managing a multifamily property isn’t just about collecting rent—it’s about building a business that creates lasting passive income and long-term financial freedom. In this episode, Gino Barbaro (co-founder of Jake & Gino) breaks down the often-overlooked “Manage Right” framework of real estate investing. While buying and financing deals may seem exciting, true wealth comes from learning how to manage multifamily properties the right way.In this lesson, you’ll discover the critical differences between property management and asset management, why systems and culture are essential to scaling, and how to avoid common mistakes new investors make. Gino shares lessons from his early days managing a 25-unit deal all the way to scaling a 1,500+ unit portfolio. Whether you’re just starting out or managing hundreds of doors, this episode will teach you how to run your real estate like a business and ensure consistent cash flow, strong returns, and sustainable growth. If your goal is real estate investing, building passive income, and achieving financial freedom, this is the playbook you’ve been waiting for.  We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

From texting workflows and estimate calculators to Google’s four-result “Monopoly board,” Phil shows how better ops beat “more leads.” We dig into retargeting your ignored database, the five metrics that matter, and how AI/LLM authority content will shape the next decade. Whether you run HVAC, plumbing, gutters—or manage 1,800 units—these tactics turn chaos into pipeline. Watch to level up your home service marketing today.Connect with Phil RisherWebsite: https://phlashconsulting.com/ Chapters:00:00 – Introduction 07:19 – Two big fixes: ROAS visibility + lead management 09:11 – Text-first workflows that boost response & bookings 13:37 – Chat-to-text widgets & estimate calculators that convert 22:10 – Google “Monopoly board”: LSA, Search Ads, Map Pack, SEO 24:26 – Content flywheel from real customer calls (They Ask, You Answer) 27:21 – AI search & becoming the local authority with content 38:28 – Scaling ladder & PE honey holes (retargeting) 44:45 – Gino Wraps it Up We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

On this episode, Julia and Gino interview Father Leo Patalinghug. Born in the Philippines and raised in the Baltimore area, Fr. Leo actually developed his love for cooking while attending the seminary at the North American College in Rome. There, he became friendly with several Italian restaurant owners and would often invite them back to the student kitchen to trade cooking secrets. They would teach him about rigatoni and lasagna; he would show them how to make hamburgers and ribs. Today, he is a skilled cook who still enjoys learning how to make new dishes, and loves the process of preparing a meal, as much as he does sharing it with a table full of friends. Fr. Leo is the host and founder of Grace Before Meals, an apostolate to strengthen families and communities around the dinner table. He is a priest ordained for the Archdiocese of Baltimore, serving as a sacramental and pastoral minister on a part-time basis. Key Chapters:00:00 Introduction03:12 Elevating culture and family life with Plating Grace07:44 Choosing vocation10:30 Books authored by Father Leo15:24 How eating can make you holy?19:51 How to get people around dinner table and share ideas27:22 How to handle emotions when conversations get heated30:15 Wrap-up To know more about Father Leo Patalinghug, visit  https://platinggrace.com/ In real estate, your network is your net worth, attend our Live Events and network with the fellow investors and professionals: https://jakeandgino.com/live-events/   About Jake & GinoJake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company that controls over $225,000,000 in assets under management. They have created the Jake & Gino community to teach others their three-step framework: Buy Right, Finance Right and Manage Right®, and to become multifamily entrepreneurs. Subscribe to this channel: https://ytube.io/3McA   Sign up for free training: https://jakeandgino.mykajabi.com/freetraining The resources you need to succeed at every level of apartment investing: https://jakeandgino.com/resources/   Apply for Mentorship: https://jakeandgino.com/apply/   #realestate #multifamilyrealestate #multifamilyinvesting #investing #apartmentinvesting Jake & Gino Facebook: https://www.facebook.com/jakeandgino/  Jake & Gino Twitter: https://twitter.com/JakeandGinoJake & Gino Linkedin: https://www.linkedin.com/company/jake-and-gino-llc/Jake & Gino Instagram: https://www.instagram.com/jakeandgino/ More ways to engage with the Jake & Gino Investor Community:MM5: https://jakeandgino.com/mm5/  Rand Cares: https://jakeandgino.com/randcares/The 100 Year Real Estate Investor: https://www.dualassetstrategy.com We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/

In this episode of the Jake & Gino How-To Series, Gino Barbaro shares his top five books for multifamily real estate investing. Whether you’re just starting your journey or scaling your portfolio, these timeless reads will give you the mindset, financial intelligence, and negotiation skills needed to succeed in real estate investing. From classics like Rich Dad Poor Dad to powerful guides like Never Split the Difference, this list will help you build wealth and achieve financial freedom through multifamily real estate. Real estate investing is 80% mindset and 20% mechanics, and these books prove it. Gino breaks down why The Richest Man in Babylon lays the foundation of wealth-building, how The Psychology of Money shapes your relationship with finances, and why Think and Grow Rich still influences today’s top entrepreneurs. He also covers negotiation strategies from Chris Voss’s Never Split the Difference, creative deal structures in Creative Cash, and market analysis insights from Dave Lindahl’s Multifamily Millions. Each recommendation gives you the tools to overcome limiting beliefs, understand the rules of money, and master multifamily real estate. If your goal is to create passive income, scale your portfolio, and achieve long-term financial freedom, these book recommendations are your roadmap to success.Connect with Gino Barbaro: [email protected] more at: https://www.wheelbarrowprofits.com We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

In this episode of the Jake & Gino Show, we dive deep into the future of blockchain and real estate investing with Aly Madhavji — Managing Partner at Blockchain Founders Fund, UN consultant, author, and venture capital leader. Aly shares his journey from a refugee background to running a global VC fund with over 200 portfolio companies, while also breaking down how blockchain, crypto, and tokenized real estate could disrupt traditional finance and transform access to wealth creation. If you’re serious about real estate investing, technology, and building financial freedom, this conversation will expand your perspective.From crypto adoption to tokenized real estate and venture capital strategies, Aly explains the opportunities and risks in today’s fast-moving digital economy. We cover the rise of decentralized finance, the potential of central bank digital currencies, how blockchain can streamline inefficiencies, and where real estate investing intersects with tokenization. Whether you’re an investor, entrepreneur, or simply curious about financial innovation, this episode highlights why blockchain is more than hype — it’s a shift with real-world impact.Connect with Aly Madhavji:Website: https://blockchainff.com Chapters:0:00 - Introduction  2:33 - Investing in Early-Stage Companies & Building Unicorns  6:26 - Crypto’s Ideological Roots vs Practical Applications  12:02 - Central Bank Digital Currencies & Risks of Government Control  20:46 - Singapore’s System vs U.S. Inefficiencies  25:19 - Blockchain, Crypto, and Real Estate Investing Opportunities  32:40 - Success Rates & Liquidity in Venture Capital  47:23 - How to Connect with Aly & Learn More  48:24 - Gino Wraps it Up   We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

The multifamily real estate market is in transition, and investors need clarity. In this episode, Gino Barbaro, co-founder of Jake & Gino, shares the state of the multifamily market and what CEOs and investors must watch closely—from rising interest rates to unreliable economic data shaping Fed policy.You’ll discover practical strategies for navigating debt, working with lenders, and positioning yourself for future opportunities. Gino also highlights lessons from Argentina’s reforms, the impact of AI on bureaucracy, and why today’s decisions set the stage for tomorrow’s passive income.Key Topics CoveredWhy government job numbers and Fed decisions can’t always be trusted How interest rate policy has impacted multifamily investors and syndicators The risks of short-term financing and negative leverage in real estate Insights from community banks and credit unions on today’s lending climate Global economic lessons from Argentina’s reforms and inflation control Practical steps for connecting with brokers, lenders, and investors now How to prepare for the next wave of deal flow and refinance opportunities Connect with Gino Barbaro Email: [email protected] Book Request: [email protected]: https://jakeandgino.com We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Real estate investing has long been seen as a path to passive income and financial freedom, but for many investors, property management headaches hold them back. In this episode of the Jake & Gino Podcast, we sit down with Daniel Shaked, CEO of Home365, a leading proptech company revolutionizing the way investors manage properties.Daniel reveals why traditional property management is broken—and how technology, automation, and data-driven underwriting are creating a predictable, scalable way to build long-term wealth. We cover the #1 mistake real estate investors make, why property managers struggle to stay profitable, and how automation can protect your cash flow by eliminating volatility in repairs, vacancies, and delinquencies.📩 Connect with Daniel Shaked:Email: [email protected] Website: home365.co LinkedIn: Daniel ShakedChapters:00:00:02 - Introduction  00:06:39 - How regulations stifle real estate innovation  00:13:38 - The two pillars of Home365’s disruptive model  00:17:01 - Making real estate truly passive for investors  00:29:40 - Using AI and automation to solve maintenance challenges  00:38:53 - Transparency, trust, and investor relationships  00:49:55 - Lessons from scaling across multiple states  00:56:03 - Gino Wraps it Up We're here to help create multifamily entrepreneurs... Here's how: Brand New? Start Here: https://jakeandgino.mykajabi.com/free-wheelbarrowprofits Want To Get Into Multifamily Real Estate Or Scale Your Current Portfolio Faster? Apply to join our PREMIER MULTIFAMILY INVESTING COMMUNITY & MENTORSHIP PROGRAM. (*Note: Our community is not for beginner investors) 👉https://jakeandgino.com/apply About Jake & Gino Jake & Gino are multifamily investors, operators, and mentors who have created a vertically integrated real estate company. They control over $250M in assets under management. They have created the Jake & Gino Premier Multifamily Community to teach others a simple three-step framework for investing in multifamily real estate. Connect with Jake & Gino on the social media platform you are most active on: https://jakeandgino.com/link-tree/ Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.