188. What Losing $25M Taught This Entrepreneur

17 snips

May 26, 2025

Damien Lupo, a resilient entrepreneur, shares his incredible journey from a $25 million real estate portfolio to homelessness during the 2008 crash. He discusses how this experience led to a transformative mindset shift. Lupo emphasizes the importance of trusting the growth process while debunking the myth of passive income. Listeners will learn about his Millionaire Action Plan for sustainable wealth, the significance of accountability, and actionable steps for long-term financial success. His story is a testament to viewing challenges as opportunities.

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ANECDOTE

Young Entrepreneur's Bold First Investment

Damien bought his first property at age 22 with a $10,000 credit card advance, seeing no downside.
His youthful ambition and lack of fear made risky moves feel normal and necessary for growth.

INSIGHT

Wealth Growth Takes Time

Wealth creation requires nurturing and patience, not instant success.
Damien's $25 million portfolio took years of action, care, and timing to develop.

ANECDOTE

From Millionaire To Homeless

In the 2008 crash, Damien lost his million-dollar home, Ferrari, and all access to credit.
He realized wealth is not credit lines but owning assets and financial resilience.

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Damien Lupo's journey into real estate began in his early twenties. He used a $10,000 credit card advance as his starting capital to begin acquiring properties. Through relentless effort, strategic planning, and leveraging his initial successes over several years, this initial foray into the market rapidly snowballed, eventually allowing him to build an impressive $25 million property portfolio.

But when the 2008 crash hit, Damien lost everything—his properties, investors, and even experienced homelessness. This devastating fall, however, became the catalyst for rebuilding his life from the ground up, focusing not just on financial recovery but on a profound mental and philosophical transformation.

Today, Damien runs multiple successful businesses, helps high-income earners secure their retirement with EQRP, and teaches the principles of building true, sustainable wealth from the inside out. In this interview, Damien Lupo sits down with Ryan Atkinson to share his incredible journey, how to cultivate an unstoppable mindset, the truth about passive income, investing strategies and actionable steps for anyone looking to build a strong financial foundation and achieve lasting financial freedom.

Takeaways

- Damien's childhood was marked by a scarcity mindset.

- He learned resilience and self-determination from a young age.

- Trusting the process is crucial for personal growth.

- Entrepreneurs see problems as opportunities.

- Wealth creation requires time and effort, not just luck.

- The 2008 crash taught Damien about the importance of stress testing investments.

- Ego can lead to financial downfall if not managed.

- True wealth encompasses health and time, not just money.

- Investing in personal development yields the highest returns.

- Taking action, even small steps, is essential for financial growth. Take action to get in the game.

- Know your financial reality through the three Cs: cash, credit cards, and calendar.

- True passive income doesn't exist; active engagement is necessary.

- Wealth requires nurturing and care to thrive.

- You must play to win, not just to avoid losing.

- Surround yourself with positive influences to foster growth.

- Investing is about respecting and nurturing your capital.

- The 10-Year Millionaire Action Plan provides a roadmap to financial freedom.

- Thinking bigger leads to greater potential and fulfillment.

- The biggest regret is not living up to your potential.

Tags: Strategic Planning, Service & Consulting, Financial Freedom, Wealth Building, Investing

Resources:

Start Your Business Today: https://links.upflip.com/4mvixT9
Connect with Damion: https://www.instagram.com/damion.lupo/