Go Big! Live Podcast

Hosted by Matt Drouin

Business InvestingInterviews guests

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Episodes

101

Latest episode

Apr 2025

Language

EN-US

About the show

Welcome to the "Go Big! Live" podcast, where we explore the exciting world of commercial real estate investing through in-depth interviews with successful investors who have scaled up their portfolios. Hosted by experienced real estate investor Matt Drouin, our show delves into the nitty-gritty details of each guest's first big deal, their journey leading up to it, and the challenges and rewards they've encountered along the way. Each episode offers valuable insights and actionable advice to help you make the leap into larger deals and expand your real estate empire. Join our community on Facebook for engaging Q&A sessions with our guests and the opportunity to network with like-minded investors. Get ready to be inspired, learn from the best, and go big in the world of real estate investing!

Listen to episodes

60 recent

April 17, 2025Episode 10042 min

How To Find Off Market Commercial Deals

📈 How to Get Off-Market Commercial Real Estate Deals (Even If You're Brand New)LoopNet and Crexi?🚫 That’s where deals go to die.In this final episode of the Go Big Live Podcast, I’m exposing the truth about how commercial brokers really work — and exactly how to get access to off-market deal flow before the rest of the world even knows a property is for sale.You’ll learn:✅ Why brokers never list their best deals publicly✅ How to earn your way onto their A/B/C lists✅ The 4 questions that instantly destroy your credibility (and what to say instead)✅ My B.A.N.D. Method to stand out and stay top-of-mind with brokers✅ A real case study: How my client Brian landed a 56-unit deal and added $1.8M to his net worth✅ How to avoid the rookie mistake that burns most new investors🔥 This isn’t theory — it’s the exact process I use and teach to help residential investors break into bigger commercial deals and start replacing their income in 24 months or less.

April 10, 2025Episode 9925 min

The 10 Essential Questions You Must Ask EVERY Commercial Lender You Speak With

Getting the bank to fund your commercial real estate deal isn’t about wearing a suit or having a slick pitch deck. It’s about knowing exactly how to play the game — and in this episode, I give you the entire playbook.If you’re making the leap from residential 1–4 unit investing to commercial multifamily or other income-producing assets, this is the no-nonsense, step-by-step guide you’ve been waiting for.What you’ll learn:✅ The key differences between residential and commercial loans (and why your W2 doesn’t impress lenders anymore)✅ Why local community banks and credit unions are your best friends (plus a stat that will blow your mind)✅ Exactly how to find the right banks, build real relationships, and get them to say YES✅ The 10 essential questions to ask every commercial lender (miss these and risk blowing your deal)✅ What happens behind the scenes during underwriting — and how to set yourself up for approval✅ And what you can do TODAY to get the ball rolling!💡 Whether you're eyeing your first 12-unit or scaling into 100+ doors, this video will teach you how to approach banks like a pro — and walk away with the funding to make it happen.👉 Don’t wait until you have a deal under contract. The smartest investors start building their financing relationships before they need them.00:00 Introduction to the Podcast00:27 Importance of Bank Financing01:46 Differences Between Commercial and Residential Loans04:58 Finding the Right Lender08:47 Building Relationships with Lenders12:09 Questions to Ask Your Lender21:16 Submitting Your Deal to the Bank23:34 Final Recap and Action Steps

March 27, 2025Episode 9858 min

Capital Raising 101 - My Proven 11-Step Process For Raising Millions

🚨 You Don’t Need a Website, LLC, or Pitch Deck to Raise Millions for Real Estate — and in this podcaswt, I’ll prove it. 🚨If you’ve been spinning your wheels trying to “get everything set up” before you start talking to investors... stop. That’s the fast track to missing deals and staying broke.In this training, I walk you through the exact step-by-step process my clients and I have used to raise tens of millions in private capital — without begging, chasing, or scrambling under pressure when the clock is ticking.✅ You’ll learn:The BIGGEST myth that keeps new investors brokeWhy now is the time to start building your capital base — even if you don’t have a dealHow to move investors from cold → warm → HOT using simple, repeatable strategiesThe magic question that gets investors saying “I’m in” (without you pitching anything)How to use the Four T’s to position yourself as the solution every passive investor is looking forWhere to find capital outside your current network — even if you don’t know anyone with moneyHow to build investor trust at scale using low-pressure conversations and social media📈 Whether you’re trying to raise your first $100K or your next $5M, this video lays out a battle-tested roadmap you can start using TODAY — without any prior experience or a huge personal bankroll.👉 Stick around until the end, where I share the #1 mistake most new capital raisers make that kills deals before they even start — and how you can avoid it.

March 20, 2025Episode 9733 min

🚨 Choosing A Market: The 5 Key Metrics That Could Make or Break Your Next Deal

Choosing the right market isn’t a gut decision. It’s not about where you think rents are high or where you heard investors are flocking.Most investors fail because they skip the data and jump straight to making offers.🚨 Big mistake.Before I ever invest in a market, I analyze 5 critical metrics that instantly tell me whether there’s real opportunity or if I’m about to waste months chasing deals that won’t pencil out.In my latest video, I’m breaking down:✅ Metric #1: The sneaky market indicator that reveals long-term appreciation potential✅ Metric #2: How to instantly tell if there’s ENOUGH deal flow (so you don’t waste time)✅ Metric #3: Why home values matter EVEN if you’re buying apartments (this one surprises people)✅ Metric #4: The #1 overlooked stat that silently KILLS your ability to scale (99% of investors never check this)✅ Metric #5: The data point that separates profitable markets from cash trapsThis is exactly how I analyze markets in real-time before making a move. If you want to build a real estate portfolio that grows without relying on luck, you need to watch this.The investors who master this process scale faster, waste less time, and close bigger deals with confidence.The ones who don’t? They keep spinning their wheels on markets that will never work for them.00:00 Introduction and Podcast Overview00:35 The Importance of Scaling Up01:42 Developing Your Acquisition Criteria02:20 Live Case Study: Skokie, Illinois08:02 Defining Your Buy Box08:39 Exploring Different Asset Classes20:26 Evaluating Market Demographics26:42 Pivoting to Nearby Markets29:37 Final Thoughts and Next Steps

March 13, 2025Episode 9614 min

How To Calculate Your RE Financial Freedom Number - Why Unit Count Doesn't Matter

Achieving Financial Freedom with Big Commercial Real Estate DealsIn this episode, I break down how to stop wasting time with small deals and start crushing it with larger commercial real estate projects. I take you through my 19-year journey, showing how I went from chasing small multifamily properties to making life-changing commercial investments that replaced my income in just one year. We dive deep into the importance of knowing your 'why' to push through the hurdles, and I show you how to set meaningful, actionable goals for your real estate journey. You’ll also learn the critical differences between ROI and ROE and why focusing on equity can skyrocket your portfolio growth. Plus, get actionable tips on minimizing expenses to fast-track your path to financial independence. Ready to scale up and live life on your terms? Tune in and let's get to work!00:00 Introduction to Go Big Live Real Estate Investors Podcast00:37 Matt's Journey: From Small Deals to Big Wins01:30 The Importance of Knowing Your Why02:17 Setting Up Your Commercial Real Estate Goals03:48 Why Unit Count is the Wrong Goal04:33 Focusing on Financial Independence06:59 Understanding ROI vs ROE09:02 Reverse Engineering Your Path to $100K Annual Income10:11 The Power of Momentum in Scaling Your Portfolio12:41 Conclusion and Next Steps

March 6, 2025Episode 9525 min

I was born, now I'm here, what happened in between?

he Final Chapters: Scaling My $18M Real Estate Empire - Lessons, Struggles, and SuccessIn this heartfelt episode of the Go Big Live Real Estate Investors podcast, I announce the conclusion of the podcast after nearly two years of interviews and deep dives into real estate success stories. I share my personal journey from a financially struggling childhood in Rochester, NY, to scaling an $18 million real estate portfolio. I recount key moments, like my first big deal using hard money, the impact of losing my parents early on, and how I overcame numerous challenges to achieve financial independence by age 33. This episode serves as a final message filled with inspiration and practical insights for experienced real estate investors looking to scale their operations. Stay tuned for the remaining episodes that will distill valuable lessons on eliminating capital bottlenecks, enhancing deal flow, and mastering technical aspects of commercial real estate.00:00 Introduction and Podcast Overview00:44 Announcement: Ending the Podcast02:41 Personal Journey: Early Life and Family Struggles08:16 College Years and Early Career11:02 First Steps in Real Estate17:33 Scaling Up: Bigger Deals and Financial Independence24:27 Conclusion and Future Episodes

February 27, 2025Episode 9417 min

The End...

The Final Season: Ending the Go Big Live Real Estate Investors PodcastIn this emotional episode, I announce the end of the Go Big Live Real Estate Investors podcast after nearly two years and almost 100 episodes. I share the reasons behind this decision, including a personal and financial disaster stemming from an arson incident at a historic building I owned. I talk about the traumatic impact, insurance and legal troubles, and the health consequences I faced. Reflecting on the experience, I explain my decision to enter a 'season of subtraction' and how I plan to take a step back to focus on what matters most—my health and family. I'll continue to share valuable insights and findings from my journey as a real estate investor in my final episodes, and I invite you to join me on YouTube for future content. Thank you for your support and understanding.00:00 Introduction and Big Announcement00:36 Reasons for Ending the Podcast01:48 The Pulver Building Tragedy03:47 Financial and Legal Consequences06:50 Health and Personal Reflections10:01 Season of Subtraction14:08 Future Plans and Final Thoughts

February 20, 2025Episode 9339 min

From Contracts to Conversions: The Legal Side of Real Estate with Alvin Schein

In this episode of Go Big! Live Real Estate Investors podcast, host Matt Drouin welcomes Alvin Schein, a partner at Seiden & Schein, P.C. in New York City, with over 35 years of experience in real estate law. They discuss the critical role attorneys play in commercial real estate transactions, from land use to tax incentives. Alvin shares insights into co-op and condo conversions, the impact of the 2019 rent laws, and the importance of leveraging expertise for scaling real estate operations. They also explore innovative solutions for affordable housing, including accessory dwelling units (ADUs), and the need for mixed-income communities. Tune in for actionable advice on navigating complex real estate deals and understanding the legal landscape.00:00 Introduction and Host Welcome00:26 Role of Attorneys in Real Estate01:07 Guest Introduction: Alvin Schein02:45 Alvin's Background and Early Career05:19 Impact of 2019 Rent Laws08:03 Inclusionary Air Rights and Affordable Housing10:03 Challenges in Middle-Income Housing22:33 Mixed-Income Communities and Zoning27:54 Senior Housing and Policy Recommendations32:39 Advocating for Local Housing Policies37:03 When to Hire a Specialized Attorney38:44 Conclusion and Contact InformationGet in Contact with Alvin:Website: https://www.seidenschein.com/Podcast: https://www.seidenschein.com/podcast/

February 13, 2025Episode 9252 min

Learning from Losses: Joe Downs Discusses Self-Storage and Value Creation

Host Matt Drouin, from the Go Big! Live Real Estate Investors Podcast, interviews Joe Downs, co-founder of the Belrose Group. Joe elaborates on his transformative journey from various entrepreneurial ventures to establishing a strong presence in the self-storage sector. This episode explores Joe's valuable lessons learned from his earliest mistakes, including the importance of 'keeping your head in the kitchen,' and the strategic processes of acquiring, financing, and operating self-storage facilities. Joe shares insights on building investor relationships, marketing strategies, and the operational nuances that spell success in real estate. Whether you're a seasoned investor or just starting, Joe's stories and practical advice offer compelling takeaways for all.00:00 Introduction and Host Welcome00:24 Guest Introduction: Joe Downs02:32 Joe's Background and Early Career06:32 First Entrepreneurial Venture: The Bar09:05 Transition to Real Estate12:30 Discovering Self Storage18:04 First Self Storage Deal27:03 Dynamic Pricing in Self Storage28:04 Transitioning from Multifamily to Commercial Assets29:08 Finding Deals in Self Storage32:01 Working with Brokers and VAs33:32 Building Relationships in Real Estate38:15 Financing and Capital Stack40:31 Raising Capital and Structuring Deals43:50 Marketing and Growing Your Sphere48:13 Advice for Scaling Your Real Estate BusinessConnect with Joe:Email: joe@belroseam.com

February 6, 2025Episode 9129 min

Persistence Pays: Gary Lipsky’s Million-Dollar Real Estate Strategy

In this episode of the Go Big! Live Real Estate Investors Podcast, host Matt Drouin interviews Gary Lipsky, founder and CEO of Break of Day Capital. Gary shares his journey from owning small businesses in North Jersey to acquiring over 3,200 apartment units worth more than $300 million. He discusses his transition from the education industry to real estate, including his key entrepreneurial ventures, challenges, and successes. Gary explains his first big commercial real estate deal and highlights the importance of persistence, networking, and strategic planning in the real estate business. They also delve into effective investor communication, deal flow methodology, and maintaining operational efficiency during market fluctuations.00:00 Introduction and Host Welcome00:36 Guest Introduction: Gary Lipsky01:18 Gary's Entrepreneurial Journey02:55 Transition to Real Estate06:48 First Big Deal Experience10:02 Challenges and Successes12:18 Capital Stack and Deal Flow15:49 Investor Relations and Networking19:35 Newsletter Strategies22:00 Property Management and COVID Challenges25:36 Exit Strategy and Market Conditions28:32 Conclusion and Contact InformationGet in Contact With Gary:Website: https://breakofdaycapital.com/Instagram: @breakofdaycapitalYoutube: @breakofdaycapital