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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/ -
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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.
