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

In this episode of The Hannah Hammond Show, I sit down with my good friend and marketing powerhouse, Jason Wojo. Jason isn’t just another guy running ads, he’s a strategist who’s managed over $35 million in ad spend and generated close to $150 million in revenue for his clients. With 1.5 million followers across his platforms, Jason has mastered the art of combining authenticity and boldness to dominate the digital advertising game.

We dive deep into the realities of building a personal brand and business in a world where organic growth alone won’t cut it. Jason shares eye-opening stories about the pitfalls of relying on virality and why paid ads aren’t just a luxury they’re the key to scalability and stability. From a Shopify seller’s $4 million warehouse mistake to his personal journey of turning struggles into success, Jason doesn’t hold back.

We also explore the psychology behind social media, the importance of crafting irresistible offers, and what it takes to thrive in a highly competitive space. Jason’s transparency, humor, and relentless drive make this a conversation you don’t want to miss—especially if you’re looking to level up your business and mindset.

Key Moments:
1:30 Jason Wojo Intro
2:30 The Importance of Paid Advertising for Business Growth
6:12 Choosing Content Strategy
13:00 Navigating Backlash and Viral Success
25:00 Jason’s Advice on Starting with Limited Resources
28:00 Why Referrals and Organic Growth Aren’t Sustainable
36:00 Learning Emotional Intelligence as a Business Leader
40:00 The Emotional Toll of Entrepreneurship
4800 Lessons Learned About Hiring and Team Building
54:08 How Upbringing Shapes Money Mindset
59:00 The Struggles of Dating as a Young Entrepreneur

Jason Wojo Bio:
Jason Wojo is 9 figure advertiser who has spent $34m online and generated $148M which is 4X ROAS historically. Jason runs ads for big names like Andy Elliott, Pace Morby, Kris Krohn, Justin Waller and Ryan Pineda. Jason is also featured in the Forbes Business Council and 30 Under 30 in NY Weekly Along With Taking Wojo Media, his marketing firm, to 8 figures and an Inc 5000 nomination.

Jason's IG - @thejasonwojo
Jason's Website - https://www.thewojomedia.com/

Welcome back to The Hannah Hammond Show! I couldn’t be more thrilled to kick off episode 2 with one of my closest friends and a truly transformative human, Jamil Damji. In this raw and emotional conversation, we dive deep into Jamil’s incredible story, one of resilience, reinvention, and the relentless pursuit of a better life.

Jamil opens up about his struggles with addiction, the trauma of his childhood, and his financial collapse during the 2008 market crash. But this isn’t just a story about challenges, it’s about breakthroughs. From finding meditation in the midst of chaos to building a thriving real estate empire, Jamil shows us how transformation begins from within.

We explore the power of personal growth, breathwork, and spiritual healing, diving into the life-changing practices that helped Jamil and me ,unlock deeper levels of success and fulfillment. This episode is a reminder that our past doesn’t define us, and healing is always within reach.

Join us as we discuss everything from childhood trauma to creating abundance, all while keeping it real, vulnerable, and inspiring.

Key Moments:
1:30 A Life-Changing Encounter
6:30 Childhood Trauma and Its Impact
25:00 Jamil's First Big Break in Real Estate
32:00 The Rise and Fall of Jamil's Financial Life
45:00 How Meditation Changed Jamil’s Life
51:00 Breaking Free from the Newtonian Grind
58:00 Healing Through Psychedelics
1:03:14 The Importance of Vulnerability and Authenticity
1:09:03 Practical Wisdom on Manifestation

Jamil Damji Bio:
Jamil Damji is the host of A&E's TV show, Triple Digit Flip, and co-founder of Keyglee, a nationally franchised real estate wholesaling outfit operating in 118 markets. He personally has completed more than 6,000 wholesale and fix-and-flip deals over the course of his twenty-year real estate investing career. Jamil is also the visionary behind Astroflipping, a community of real estate wholesalers with more than 4,500 active members. His true passion is teaching others how to invest in real estate in a smart, strategic, and ethical way to create generational wealth.

IG - @jdamji

In this debut episode of The Hannah Hammond Show, I sit down with the legendary Robert Kiyosaki, the author of Rich Dad Poor Dad, a book that forever altered my perspective on life and money. As a young teenager, Robert’s words were a lifeline, teaching me that true freedom isn't handed to you, it’s earned, fought for, and often misunderstood. Now, I have the privilege of diving deep with the man whose teachings shaped my journey.

Robert and I explore the raw truths about financial freedom, the indoctrination of our education system, and the sacrifices required to break free from societal norms. From his harrowing experiences in Vietnam to his unfiltered critique of modern financial education, Robert lays bare the cost of freedom both personal and financial.

This conversation is packed with hard-earned wisdom, actionable insights, and candid moments that will challenge everything you thought you knew about success, security, and freedom. Whether you're an aspiring entrepreneur or just beginning to question the system, this episode will inspire you to take control of your future and start creating a life of true independence.

Key Moments:
1:10 Learning about money through monopoly
5:50 Markets crashing creates opportunities
12:20 The sacrifice needed for success
20:50 Lessons rejection can teach
23:14 Why most teachers are broke
30:00 The future of financial education
33:35 Selling is the best skill for any entrepreneur

Robert Kiyosaki Bio:
Best known as the author of Rich Dad Poor Dad, the #1 personal finance book of all time, Robert Kiyosaki has challenged and changed the way tens of millions of people around the world think about money. He is an entrepreneur, educator, and investor who believes the world needs more entrepreneurs who will create jobs.