In this deeply personal and inspiring episode, I sit down with my good friend, Zachary Kepes, a true powerhouse in the real estate world. Zach has built an awe-inspiring portfolio, owning nearly 300 single-family rentals in Arizona, valued at over $100 million. But this conversation isn’t just about numbers and success it’s about vulnerability, resilience, and the raw truth of what it takes to balance ambition and life.

Zach opens up about his journey, from starting in real estate over two decades ago to navigating the financial crash of 2007 that wiped him out completely. He shares the hard-earned lessons that came from rebuilding his empire, one house and one relationship at a time. We also dive into the deeper side of life, how his relentless drive has sometimes led to personal sacrifices and moments of reflection, like the time he realized he wasn’t fully present for his dad during a life-altering moment.

This isn’t just a story of success; it’s a story of humanity. Zach’s candidness about his struggles, mistakes, and victories will inspire you to chase your dreams while staying grounded in what truly matters: connection, legacy, and being present for the ones you love.

Key Moments:
1:30 Who is Zachary Kepes?
5:00 Lessons from the 2007 Financial Crisis
11:50 Raising Capital & Building Trust with Investors
20:00 Shifting from Flipping to Building a Rental Portfolio
25:09 Zach’s Four Pillars of Investments
37:29 Finding Fulfillment Beyond Financial Success
45:00 The Day Zach's Life Changed With His Dad
50:00 Vulnerability & Overcoming Personal Struggles

Zachary Kepes info:
IG - @zakventures
YouTube - @ZakVentures
LinkedIn - https://www.linkedin.com/in/zachary-kepes-8a653236/

I’ve always believed in the relentless pursuit of freedom, and today’s guest embodies that philosophy in every way. I’m joined by the incredible James Dainard, a powerhouse in real estate and one of the most genuine humans I’ve ever met. From humble beginnings in Sammamish, Washington, to managing over a thousand rental units, co-hosting the BiggerPockets On the Market podcast, and authoring The Flipping Framework, James has redefined what it means to build an empire with heart.

In this conversation, James opens up about hitting rock bottom at 19, his decision to leave drinking behind, and how that clarity reshaped his life. We explore how he transformed challenges into opportunities, building a vertically integrated real estate empire that includes flipping, private money lending, and multifamily syndications. James also shares the lessons behind his success: authenticity, hard work, and always creating solutions for clients.

Whether you're an entrepreneur, investor, or someone navigating your path to freedom, James’s journey is proof that resilience and a clear vision can change everything. Get ready to be inspired, take notes, and learn from one of the best in the game.

Key Moments:
1:30 Who is James Dainard?
6:40 Breaking the Cycle
10:00 The Power of Accountability
16:00 Growth Through Adversity
27:00 Solving Problems, Not Selling
44:00 Lessons from the 2008 Crash
54:00 Finding the Sweet Spot In The Market
57:00 The Flipping Framework
1:10:00 Redefining Freedom

About James Dainard:
At the age of 23, James Dainard began his real estate career while completing his business degree at UW. Over the past 18 years, James has become the foremost expert real estate investor in Washington state with an unparalleled reputation. He is a managing partner of a family of real estate investment companies that that have a combined annual revenue of $30-$40 million annually. Heaton Dainard – a full service real estate brokerage, Buck Buys Houses – an off-market property acquisition company, Intrust Funding – a hard money lender, and Limelite Development – a development company that specializes in fix and flip, town home and single family ground up construction, Coverse Capital, a Multifamily and syndication holdings company, and Project RE – a real estate educational platform.

James specializes in VALUE-ADD acquisitions and has been involved in over 2,000 renovations from fix-and-flip, ground up development and construction, apartment turns. James is an active investor in the Pacific North West who has grown his real estate portfolio to nearly 1,000 doors. As a real estate broker, James has completed over 4,000+ real estate transactions direct to investors, totaling over a billion in sales. James’ success has garnered accolades including his companies winning Washington’s Fastest Growing Private Companies, Inc 500, and being selected by the Puget Sound Business Journal’s 40 under 40 list. James is one of the co-hosts for Bigger Pockets On The Market and has recently released a book with Bigger Pockets title James has recently released called The Flipping Framework, a book that educates readers how to establish a successful fix and flip business and how to maximize profits with value add construction, James will also going to be featured on a major network TV show in late spring 2025.

In addition to running seven active Real Estate companies, he coaches students throughout the US on how to achieve their financial goals through real estate investing.

James Dainard links:
www.jamesdainard.com
www.heatondainard.com
www.intrustfunding.com
www.limelitedevelopment.com
www.buckbuyshouses.com

This episode is one of the most personal and vulnerable conversations I've ever shared. For years, I felt stuck, broken, and unworthy. I carried the weight of trauma, addiction, and self-doubt, hiding behind overachievement as my only means of survival. My childhood was filled with challenges that shaped my perception of love, trust, and connection. From witnessing addiction and facing betrayal to grappling with my own mental health and eating disorders, the journey has been anything but linear.

Today, I’m living proof that transformation is possible. I’ve built thriving businesses and achieved financial freedom, but none of that mattered until I learned to truly love myself and heal from within. This episode isn’t just about my successes; it’s about the raw, unfiltered path that brought me here, the pain, the lessons, and the breakthroughs.

If you’ve ever felt stuck or wondered if it’s possible to create a life of purpose, fulfillment, and joy, this episode is for you. I share my story not for sympathy but to show you that no matter where you start, you are capable of extraordinary things.

Key Moments:
5:00 Early Lessons on Money and Freedom
15:00 High School Realizations and First Steps into Business
19:00 First Big Real Estate Win
24:00 The Impact of Success Without Fulfillment
27:00 Struggles with Addiction and Relationships
39:00 The Breakthrough Moment: Seeking Help
42:00 Spiritual and Emotional Transformation
47:00 Mission to Help Others