Growing Empires

Jennifer DeJesus
  • 5.0 (1)
  • Investing
  • Updated Weekly

The New Growing Empires: Where Capital, Strategy, and Structure Meet True wealth isn’t found in a deal; it’s engineered through the architecture of the investment. Hosted by Real Estate Entrepreneur, Jennifer DeJesus, Growing Empires is the definitive resource for high-net-worth individuals who prioritize passive wealth and long-term performance. We strip away the surface-level “hustle” to provide the investor intel needed to navigate today’s complex markets. At the intersection of Capital, Strategy, and Structure, we explore: —Capital: Sophisticated allocation, private equity, and institutional capital strategies for the wealthy. —Strategy: Real-deal case studies, vertical integration, and the “boots on the ground” execution that manufactures alpha. —Structure: Alternative investments, tax-efficient frameworks, and the organizational logic that turns a portfolio into a legacy. Whether you are looking for a deep di

Episodes

  1. 2d ago

    GE 012 - How Self-Managing Quietly Kills Your Real Estate Investment Returns

    In this episode of Growing Empires, I challenge one of the biggest misconceptions in real estate investing: that self-managing your properties is the best way to save money. On the surface, avoiding a management fee sounds like a smart financial decision. But after nearly two decades of operating and managing investment properties, I've learned that the real costs usually show up somewhere else, in extended vacancies, below-market rents, delayed maintenance, poor tenant retention, and countless hours spent handling problems that pull you away from growing your portfolio.

  2. Jul 16

    GE 011 - The Deal Everyone Passed On: An 8-Unit Multifamily Success Story

    In this episode of Growing Empires, I take you inside one of the most challenging and rewarding deals I've ever been involved with. It started with an eight-unit property that had been sitting on and off the market for years. No reliable records. No clear picture of who was actually occupying the building. A long list of problems that caused most investors to run the other way. But sometimes the opportunities everyone else ignores are the ones worth looking at most closely. I walk through how we found the deal, evaluated the risks, and determined whether the upside justified the challenges ahead. From navigating code violations, squatters, and neighborhood concerns to developing a renovation strategy and assembling the right team, this project tested every part of the acquisition and execution process. I share some of the due diligence lessons and decision-making frameworks that helped turn uncertainty into a workable plan. And unexpectedly, when everything seemed to be coming together, COVID threatened to derail the entire investment. What happened next reinforced one of the biggest lessons I've learned in real estate: success isn't just about finding the right property. It's about having the right strategy, the right partners, and the ability to adapt when circumstances change. If you've ever wondered how experienced investors evaluate risk, uncover hidden opportunities, and navigate the unexpected, this Inside the Deal episode is for you.

  3. Jul 9

    GE 010 - How Real Estate Investors Legally Reduce Taxes with special guest CPA, CJ Tarantino

    In this episode of Growing Empires, I sit down with CPA and tax advisor CJ Tarantino to discuss some of the most effective tax strategies available to real estate investors. As investors, we spend a lot of time focused on finding deals, raising capital, and managing assets, but keeping more of what we earn is just as important. CJ shares practical insights into how tax planning can become a powerful wealth-building tool when approached strategically rather than reactively. Throughout our conversation, we explore topics including depreciation, cost segregation studies, real estate professional status, 1031 exchanges, entity structuring, and several lesser-known tax-saving opportunities that investors often overlook. CJ also explains the critical difference between working with a tax preparer and partnering with a proactive tax advisor who understands the unique needs of real estate investors. Whether you're just beginning to build a portfolio or you're managing a substantial real estate business, this episode offers valuable guidance on how to approach tax planning with greater confidence and clarity. My hope is that you'll walk away with at least one strategy to discuss with your CPA and a better understanding of how thoughtful tax planning can help support your long-term investment goals. Key Takeaways • Why real estate remains one of the most tax-advantaged asset classes available • How depreciation can create significant tax savings for investors • When a cost segregation study makes sense and when it may not • The importance of working with qualified cost segregation professionals • The difference between a tax preparer and a proactive tax advisor • What real estate professional status is and who may qualify • Common mistakes investors make when documenting participation hours • How a "lazy 1031 exchange" strategy may help offset gains • When a Delaware Statutory Trust (DST) may be an option for investors seeking a more passive approach • How paying your children through your business can create legitimate tax advantages • Why the home office deduction is often misunderstood • How entity structure can impact taxes, liability protection, and long-term strategy • Why proactive tax planning throughout the year can lead to better outcomes than simply filing a return each spring

  4. Jul 2

    GE 009 - Why Smart Real Estate Investors Never Wait for the "Perfect" Market

    In this investor intel episode, I share insights from a recent conversation with a fellow real estate investor whose journey began much like my own. We both started in corporate America, searching for a path that offered more freedom, more control over our time, and a greater opportunity to build long-term wealth. While our investment strategies ultimately took us in different directions, one thing remained true for both of us: real estate became the vehicle that helped us create financial independence.

  5. Jun 25

    GE 008 - The Future of “Growing Empires:” Real Estate Investing, Insider Strategies, and the Stories Behind the Deals

    In this episode, I pull back the curtain on an exciting new chapter for Growing Empires and share how the show is evolving into a deeper, more strategic resource for investors at every stage of their journey. We talk about the new content structure I’m building and why I want to go beyond surface-level conversations to bring you practical insights that help you think differently about investing, building wealth, and scaling your opportunities in real estate. I’ll walk through the four new pillars of the show: Lessons from the Frontline, where I share real stories, mistakes, wins, and hard-earned lessons; Inside the Deal, where we get into the details of acquisitions, capital stacks, negotiations, and how deals truly come together; Capital Conversations, where I introduce you to trusted experts and advisors from my own network; and Investor Intel, which will deliver focused mini masterclasses designed to help you sharpen your investment knowledge and skills. As we wrap up this interview series, I also reflect on what drives me most. For me, this business has always been about relationships. I love helping people create opportunities, build financial freedom, and move closer to the life they want. Real estate is more than transactions and properties. It's about creating impact, and that’s what I’m most excited to continue bringing to you through the next evolution of Growing Empires.

  6. Jun 18

    GE 007 - My Real Estate Origin Story: Leadership Lessons From Growing an Investment Ecosystem

    In this episode, I share some of the biggest leadership lessons I've learned throughout building my businesses and growing what has become an entire ecosystem of companies. Early on, like many entrepreneurs, I was doing everything myself. As the business expanded, I realized growth wasn't simply about working harder or adding more responsibilities to my plate. It was about creating efficiencies, building systems, and learning how to delegate so I could focus on the areas where I brought the most value. I also talk about how my approach to hiring evolved over the years. Initially, I focused heavily on experience and industry knowledge, but I eventually realized that attitude, values, and a willingness to learn mattered far more. Some of the best people I've ever brought into the organization came from completely different industries and challenged us to think differently. Their perspectives helped create new efficiencies and improve the way we operate. Today, I hire for attitude and train for skill because great people often bring value you can't always see on a résumé. We also dive into leadership beyond employees and teams and into the relationships that drive growth: clients, investors, and business partners. I talk about what I've learned about building partnerships, finding complementary strengths, and creating clear expectations from the beginning. At the end of the day, growth isn't about finding another version of yourself. It's about putting the right people in the right seats and creating an environment where everyone can contribute to building something larger than themselves.

  7. Jun 11

    GE 006 - My Real Estate Origin Story: How I Created a Real Estate Fund to Beat a Changing Market

    In this episode of Growing Empires, I share one of the biggest shifts in my journey as a real estate operator: moving beyond building businesses and stepping into the world of funds, syndications, and larger investment opportunities. As market conditions changed and competition increased, I realized I needed to create a solution that would continue helping investors grow, even when traditional deal flow became more difficult to access. I walk through the thought process behind launching the Empire Capital Fund and explain why I chose a hedge fund structure instead of traditional approaches. As outside capital began flooding into our market and competition for properties increased, I knew I had to think differently. Rather than telling investors to sit on the sidelines or wait for market conditions to improve, I focused on creating access to opportunities that most investors would never see. I also pull back the curtain on how I source off-market deals and why relationships have become one of the most valuable assets in my business. From direct-to-seller opportunities and estate properties to bank relationships and distressed assets, I explain how creating a strong network and staying ahead of market trends opened doors to opportunities that continue to benefit our investors today. At its core, this episode is about adapting, staying resourceful, and creating solutions when the market changes around you.

  8. Jun 4

    GE 005 - My Real Estate Origin Story: The Strategy That Helped Investors Scale From 1 Property to 100

    In this episode of Growing Empires, I talk about how I watched both the real estate market and investor behavior evolve over the years—and how I evolved right alongside them. When I first entered the industry after the housing crash, most investors were buying small properties with cash: single-family homes, student rentals, and small multifamily buildings. But as I gained experience and helped clients grow their portfolios, I started to realize we were building much more than transactions. We were creating a repeatable system for long-term wealth building. I share how investors began using equity, tax strategies, and leverage to scale beyond small investments and into larger opportunities. I explain how selling properties, deferring capital gains through strategies like 1031 exchanges, and reinvesting into larger assets created a cycle of growth that allowed many clients to dramatically increase both their cash flow and overall net worth. What started as helping people buy investment properties slowly became a roadmap for building wealth over time. I also walk through one of the most important lessons I learned along the way: how smart investors use leverage and “other people’s money” to expand opportunities far beyond what cash alone can provide. Real estate is constantly changing, markets shift, and strategies evolve, but the people who continue to grow are the ones willing to adapt. Sometimes the biggest opportunities come from understanding when to shift your strategy instead of stepping away from the game.

  9. May 28

    GE 004 - My Real Estate Origin Story: The Mishaps That Inspired a Multi-Company Ecosystem

    In this episode of Growing Empires, I continue sharing the story of how my businesses came to life, and the truth is, none of it started with some perfectly mapped-out master plan. Every company I created came from real experiences, real frustrations, and real client needs. What started with helping one investor achieve his goals slowly evolved into an interconnected ecosystem of businesses designed to create better outcomes and better experiences. I talk about some of the pivotal moments that shaped the way I operate today, from tenant situations that led me to implement quarterly property inspections, to frustrations with title companies, contractors, and vendors that pushed me to create entirely new solutions. Instead of accepting the way things had always been done, I kept asking myself how I could improve the process and better serve my clients. This conversation is really about more than real estate. It is about listening, adapting, owning mistakes, and using challenges as opportunities to build something stronger. Looking back, many of the businesses I run today were born from moments of frustration, feedback, and lessons learned along the way, and together they became the ecosystem I now use to help investors build long-term wealth.

  10. May 21

    GE 003 - My Real Estate Origin Story: The One Call That Changed Everything

    In this episode, I share the real origin story behind my property management business and how it all started with a single phone call I almost missed. What began as an end-of-day situation in a traditional real estate office turned into a defining moment in my career. I didn’t have expertise in investment properties at the time, but I did have a willingness to respond, figure things out quickly, and follow through without hesitation. That one client introduced me to a completely different way of thinking about real estate through the lens of investment, cash flow, and long-term strategy. As I stepped into managing his properties, I found myself learning on the fly: researching unfamiliar concepts, building systems from scratch, and paying close attention to how experienced investors actually evaluate decisions. What followed wasn’t just one transaction. It was a shift in direction. Through referrals and ongoing work, I began managing a growing portfolio and quickly learned what it means to operate at scale in property management. More importantly, I started to see the gap between transactional real estate and true investment-focused service. This episode is about that turning point; the call, the mindset shift, and the early lessons that reshaped how I approach real estate entirely.

  • 10 Episodes

About

The New Growing Empires: Where Capital, Strategy, and Structure Meet True wealth isn’t found in a deal; it’s engineered through the architecture of the investment. Hosted by Real Estate Entrepreneur, Jennifer DeJesus, Growing Empires is the definitive resource for high-net-worth individuals who prioritize passive wealth and long-term performance. We strip away the surface-level “hustle” to provide the investor intel needed to navigate today’s complex markets. At the intersection of Capital, Strategy, and Structure, we explore: —Capital: Sophisticated allocation, private equity, and institutional capital strategies for the wealthy. —Strategy: Real-deal case studies, vertical integration, and the “boots on the ground” execution that manufactures alpha. —Structure: Alternative investments, tax-efficient frameworks, and the organizational logic that turns a portfolio into a legacy. Whether you are looking for a deep di

Information

  • Creator
    Jennifer DeJesus
  • Years Active
    2026
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © Copyright 2026 Jennifer DeJesus. All Rights Reserved.
  • Show Website
    Growing Empires