Jake and Gino Multifamily Investing Entrepreneurs
Welcome to Jake and Gino's podcast, where we cut through the noise of entrepreneurship and real estate investing. If you're a forward-thinking individual, eager to take the plunge into the business or multifamily real estate investing world, then this is the show for you! Here, you'll discover invaluable insights from industry leaders who have walked the path and made their marks. Every episode is a mini masterclass, covering topics like startup growth, venture capital, business acquisitions, and real estate market cycles. But it's not all roses - we also delve into the hard truths of entrepreneurship and investing, sharing the hurdles, pitfalls, and challenges you're likely to encounter, and strategies on how to navigate them. Thinking about partnering with us? This podcast is a sneak peek into our ethos and approach. We believe in turning real-world experiences into tangible lessons, and it's this ethos that guides our mentorship programs. Whether you're planning to dive into multifamily real estate investing or expand your business horizons, our show provides the knowledge and inspiration you need to make those dreams a reality. Join Jake and Gino on this journey and let's transform your entrepreneurial and investing landscape together! Also included under The Jake & Gino umbrella: The Julia & Gino Show: Where Business Meets Family. This couple explores the harmony of relationships, communication, and business success How To: A concise video series guiding aspiring individuals towards financial freedom through multiple passive income streams and generational wealth via multifamily real estate investing. Movers and Shakers: Gino Barbaro features Jake & Gino students who are successfully navigating multifamily real estate deals. Our mission is to create Multifamily Entrepreneurs!
Episodes
The government shutdown and multifamily real estate market are more connected than you think. In this How-To episode, Gino Barbaro breaks down how a government shutdown can ripple through your investments — from USDA and Section 8 properties to loan processing delays and market uncertainty
When the government halts operations, multifamily investors can face serious ripple effects — delayed rent subsidies, halted USDA loans, and ner...
You’ll learn why Kent chose individual investors over institutions, how he raised his first $1.5M for a 30-unit development, and the systems (EOS, vertical integration) that helped deliver consistent performance—averaging 19.7% annually across realized deals. We compare Institutional vs Individual Real Estate Investors on speed, control, red tape, and relationship capital, and dig into current market dynamics: 2024’s supply bulge, ...
If you’ve ever wondered how to raise capital for real estate investing, this episode breaks it all down. Jake & Gino co-founder Gino Barbaro shares a step-by-step guide to mastering the art of raising money—from your very first deal to becoming an expert capital raiser. Whether you’re funding your first duplex or managing millions in multifamily, this episode will help you raise capital with confidence and integrity.
In this How To...
Want a clear read on 2025 Hiring Trends from someone who’s placed talent nationwide for 20+ years? Frontline Source Group CEO Bill Kasko joins Jake & Gino to unpack the real shifts behind AI, return-to-office, and why employers reclaimed leverage since late 2024.
We break down how the market flipped post-September 2024 and what that means for offers, counteroffers, and retention. Bill explains why workforce participation, aging dem...
Raising capital for real estate can make or break your investing journey. In this episode, Gino Barbaro from Jake & Gino shares a complete framework to help beginners, intermediates, and advanced investors understand how to raise capital the right way—without burning trust or making costly mistakes.
From his first 25-unit deal to managing syndications, Gino explains why raising capital for real estate isn’t just about pitching dea...
Blue collar entrepreneurship is exploding — and you don’t need a four-year degree to build a profitable, scalable business. In this episode Ken Rusk (author of Blue Collar Cash) explains why trades are back, how to launch a business from day one, and the mindset you need to win.
Ken breaks down practical steps for blue collar entrepreneurship: choose a clear vision, earn while you learn, and build owner-like teams through intrapren...
Creating a Multifamily Business Plan is the foundation of becoming a successful real estate investor. In this episode, Gino Barbaro breaks down the Buy Right, Manage Right, and Finance Right framework while sharing lessons from his own investing journey. Whether you’re new to multifamily or looking to refine your approach, this video will help you build a clear path to long-term wealth.
In this training, Gino explains why cash flow ...
AI for Real Estate Investors is changing the game. In this episode, Jake & Gino sit down with serial entrepreneur Nadav Wilf to explore how artificial intelligence is transforming deal sourcing, property management, and investor efficiency. From automating workflows to boosting qualified deal flow, this conversation will open your eyes to the future of investing.
Nadav breaks down exactly how AI can free up time, streamline operatio...
The multifamily market is shifting, and multifamily market oversupply is at the center of it all. With rents softening, vacancies rising, and concessions piling up, investors need clarity to navigate 2025 and beyond.
In this episode, Gino Barbaro breaks down the reality behind the headlines and shares insights from his own market experience in Knoxville, Nashville, and beyond. You’ll learn why oversupply is hitting certain cities ha...
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 burno...
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 g...
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 firs...
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 rig...
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.
Conn...
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 ...
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 traditi...
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. G...
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-...
In this episode of Jake & Gino’s How-To series, Gino Barbaro breaks down positive leverage in real estate and how to thrive in today’s high-interest rate environment. With borrowing costs at 6–7% and cap rates often compressed, many investors are struggling to make deals pencil. Gino shares practical steps to find and structure deals that still produce strong returns without relying on unrealistic rent growth projections.
You’ll lea...
Estate planning isn’t just for the wealthy—it’s for anyone who wants to protect their family, avoid costly legal battles, and pass on assets with peace of mind. In this Jake & Gino episode, we sit down with Zach Tsakiris, founder of FastWill, a revolutionary platform making estate planning fast, affordable, and accessible from home.
We cover why 70% of Americans don’t have an estate plan, the hidden risks of letting the state decide...
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