Financial Underdogs

Financial Underdogs

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Financial Underdogs episodes

  • The Domino that changes your life FU 138

    What's the one domino that, once it falls, knocks down everything else?

    That's your big domino: the one decision or habit that sets off a chain reaction in your life.

    In this episode I share how to find yours, and the moves that keep the chain going:

    • Find your big domino. The one decision or habit that can trigger real change.
    • Get a world-class coach, mentor or therapist. Someone who gives you honest feedback and shows you your blind spots. That relationship may matter more than most others in your life.
    • Clean fuel, clean life. Cut back on alcohol and processed food. What you put in drives your energy, your focus and your health.
    • Hire a world-class integrator. An executive assistant or integrator takes tasks off your plate, so your head is free for vision and strategy instead of logistics.
    • Set boundaries. Guard your time and energy from the vampires who drain them. Your time is your most prized possession.
    • Live by design, not default. Use tools, systems and boundaries to stay on your goals instead of reacting to other people's agendas.

    2025 is about simplicity and clarity. Find your big domino and let it knock down the rest.

    Resource mentioned: Boundaries by Dr. Henry Cloud and Dr. John Townsend

    Listen and subscribe: Apple Podcasts · Spotify · All episodes

    More from Damion: damionlupo.com/podcast · X @damionlupo · YouTube

    13 min
  • Trading vs. Investing - Happy High or Wealthy

    Trading or investing? One gets you high. The other makes you wealthy.

    I started out as an overconfident rookie trader. In this one I share how that went, from losing on margin to chasing meme coins in the crypto craze. I learned the expensive way that trading is dominated by machines, algorithms and PhDs with endless resources.

    Investing is a different game. Big picture. Long-term value. No instant gratification.

    What we cover:

    • Trading = stress, losses and competing against pros with endless resources.
    • Investing = patience, growth and backing visionaries and impactful projects.
    • Why investing in people and leadership matters most. Great leaders can turn even mediocre ideas into big wins.
    • Building vs. taking: creating real solutions that help society is what builds wealth that lasts.

    Do this:

    • Stop chasing quick wins. Plant seeds that grow into something.
    • Research the leadership behind any company or project before you invest.
    • Judge every investment on a 5–10 year horizon. Are you growing a tree or just picking low-hanging fruit?

    Books mentioned: Flash Boys and The Big Short, both by Michael Lewis.

    If this one hits, follow the show and send it to a fellow underdog.

    14 min
  • Cleaning up your life before you Create a new year, The Key 5 C's

    Before you create a new year, clean up the old one.

    In this episode I walk through how I clear the decks for 2025 with my 5 C's: Clutter, Connections, Calendar, Cash and Clarity.

    • Clutter. Physical and digital. Clear out the stuff you don't need, organize your files and get rid of the duplicates. A blank slate makes room for new experiences.
    • Connections. Who are the three to six people you'll pour your time into? Invest on purpose in the relationships that matter: friends, family and professional contacts. Add help that gives you leverage, like an executive assistant or a personal trainer. Cut what wastes your time, like TSA lines and commercial airports.
    • Calendar. Wipe it every year. Only meaningful meetings make the cut, and Slack and Zoom replace the old meeting formats.
    • Cash. Pay off the credit cards and make it a top priority if you want your freedom back. Then stop the cash creep: cancel the subscriptions you don't use, shop your insurance and stop the charges you never wanted.
    • Clarity. Decide what you'll study in 2025. For me it's AI and technology. I expect automation to take over most human labor in the next five years. Stay relevant by solving meaningful problems, set specific, actionable goals, and use other people to hold you accountable all year.

    Clean up now, so you can create a 2025 that actually means something.

    Listen and subscribe: Apple Podcasts · Spotify · All episodes

    More from Damion: damionlupo.com/podcast · X @damionlupo · YouTube

    22 min
  • The Power of Planning, Picking and Purging People in your life FU 135

    In this episode, we're diving into the importance of building conscious, circular relationships—connections that pour energy into both sides and drive you toward a life of purpose, success, and abundance.

    Discover how saying "no" to the wrong people creates space for the right ones, why relationships are the foundation of a thriving life and business, and the rules I follow to maintain meaningful connections. We'll also explore how these principles align with building a billion-dollar company, including the foundational 15% strategy from Unicornomics and how the people you surround yourself with impact your future.

    19 min
  • Going From $0 to $1 Billion in 7 Years - The Pain of Discipline vs. the Pain of Regret FU 134

    Going deep on my real-life story of going from homeless to homerun. Negative millions, living in my vehicle freezing my ass off, to a decade later creating a unicorn (billion-dollar company) and a net worth of tens of millions. The formula, the thinking, and the hacks (if there are any), and your opportunity to create your decade by design. Real, true roadmap and plan and access to Damion Lupo.

    22 min
  • Being Cheap is EXPENSIVE FU 133

    Have you ever looked at your yard, laundry, or even your taxes and thought to yourself, "why would I pay someone to do this when I could do it myself and save the money?" If you answered yes, then you've traded your money for something far more valuable: your time.

    Today, I talk about how being cheap will cost you 10X the pennies you save doing the "thing" yourself, and the difference between buying time and selling your time.

    10 min
  • The Secret to Creating Goals for 2022 FU 132

    It's the end of the year, almost 2022 and it's time for Goal setting. But are you setting yourself up to fail before you start?

    Today Damion talks about using the power of Gratitude to set the stage for Goals you can achieve.

    Start with Gratitude for what is true and ONLY compare your goals to YOUR potential.

    Stop wishing for Elon money, Giselle's body or Brené Brown's relationships.

    Start with where you're at and target your potential as your vision.

    Deep into that today... 2022 lets go!

    17 min
  • Stop hoping for life - start creating your life - FU 131

    Hope it works out.

    Guess We'll see.

    Sure would be nice.

    Passive victim talk and the reason most people are broke, stuck and watching other people live the life they desperately want.

    Today we talk about the key to shifting from hoping for something to happen to making it happen.

    One key.

    10 min
  • Death of the Checkbook IRA FU 130

    The tax courts just ruled ... If you have an LLC inside of your IRA and you're using it to write checks to take possession of precious metals or doing real estate deals — it's all disqualified now!

    People have been lied to and now they're getting penalized. You gotta do the research.

    If you're trying to do something to circumvent the system you're going to get clobbered.

    9 min
  • Thinking TOO Big? FU 129

    Are you thinking TOO Big?

    Are you settling for average and not dreaming and doing big enough?

    Your potential to impact the world, your spouse, your health etc. is far greater than you realize.

    The step is to vision and normalize this vision by surrounding yourself with those who want you to win and live a BIG vision?

    5 min

About Financial Underdogs

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The Financial Underdogs podcast brings the best minds together to discuss powerful ideas to transform financial freedom. Damion Lupo teaches how to change your numbers and uncover what the financial…