PodcastsBusinessChasing Financial Freedom

Chasing Financial Freedom

Ryan DeMent
Chasing Financial Freedom
Latest episode

271 episodes

  • Chasing Financial Freedom

    Hard Money to DSCR: Don't Make This Mistake Ep 382

    20/05/2026 | 13 mins.
    Hard money to DSCR is one of the most common exit strategies in real estate investing and one of the most misunderstood. Most investors don't realize the mistake until they're already sitting at the closing table with a surprise they didn't budget for.
    In this episode of the Chasing Financial Freedom Podcast, I break down exactly where investors go wrong when refinancing a hard money loan into a DSCR loan, including a real deal case study that went completely sideways. If you're holding hard money right now, don't schedule that refi until you watch this.

    📅 Have a deal in play? Let's walk through your numbers before you make a costly mistake.
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  • Chasing Financial Freedom

    1% of Million: The DSCR Rule That's Killing Your Deals Ep 381

    13/05/2026 | 11 mins.
    You thought your DSCR hit 1.25, your credit was clean, and your cash in the bank was enough, but your lender still said you did not have the reserves to close. This episode breaks down the 1 percent of outstanding balance rule that DSCR lenders quietly apply to your entire portfolio, including your primary residence, and how that hidden requirement can stall or kill a deal when you are already deep into the process. You will learn how the reserve math really works, what counts as liquid, and the exact questions to ask your broker or lender so you are never blindsided by underwriting again. If it does not hit 1.25, it is not a deal. It is a donation.
  • Chasing Financial Freedom

    Your Credit Score Lied to You and It Is Costing You Your Next DSCR Deal Ep 380

    06/05/2026 | 13 mins.
    The credit score on your phone right now is almost certainly not the score your mortgage lender is going to use, and that gap can cost you a better rate, a cleaner approval, or the entire deal. In this episode, Ryan breaks down the difference between consumer scores and mortgage FICO scores, explains the middle score rule most investors have never heard of, walks through the three active trade line requirements, and shares a real investor story where 60 points disappeared during a renovation and almost killed a $70,000 cash-out refinance. Come in prepared with the right number, or you are not coming in at all. If it does not hit 1.25, it is not a deal. It is a donation.
  • Chasing Financial Freedom

    Why Most Real Estate Investors Regret Choosing Their Local Bank Over a DSCR Lender Ep 379

    29/04/2026 | 13 mins.
    Most investors start with their local bank because the rate is better. Then the DTI Avalanche hits at property three, four, or five, and the regret starts. In this episode of Chasing Financial Freedom, Ryan DeMent walks through exactly why local bank financing becomes a ceiling for scaling investors, how stacking properties on your personal credit quietly destroys your ability to grow and buy your own home, and what guardrails every investor needs before signing any financing. From LLC titling and personal guarantees to autopay transfers, prepayment penalties, and conservative rent comps in a softening market, this episode gives you the full picture so your next financing decision is built on strategy, not just the lowest rate on the page.
  • Chasing Financial Freedom

    The Spreadsheet Lie That Is Destroying DSCR Investors Before They Close Ep 378

    22/04/2026 | 14 mins.
    Most investors lose their deals not at the closing table but at the keyboard, where spreadsheet math, unverified rent comps, and the myth of low-rate high-leverage financing build a false picture of a deal that was never really there. In this episode of Chasing Financial Freedom, Ryan DeMent walks through a real investor call where a projected DSCR of 1.35 collapsed to 1.09 once realistic numbers were applied, and explains exactly why loan-to-value and interest rates always move in opposite directions on DSCR loans. If you are serious about building a cash-flowing portfolio and tired of deals dying at the finish line, this episode will help you stop trusting the spreadsheet and start underwriting like the lender who is about to approve or deny your loan.
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About Chasing Financial Freedom
If you're an entrepreneur, small business owner, or side hustler looking for new ways to make money, scale your business, or turn your side hustle into a business, we've got something for you. We'll be interviewing successful entrepreneurs who have turned their dreams into reality. We'll learn how they did it and what they wish they'd known before they started their businesses. Your host, Ryan DeMent, has unique insights built by 25 years of experience in the financial industry and several failed businesses. So if you're looking for new ways to make money, scale your business, or turn your side hustle into a business… then this podcast is for you!
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