Chasing Financial Freedom

Ryan DeMent
  • 5.0 (51)
  • Entrepreneurship
  • Updated Weekly

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!

  1. 2d ago

    Real Deal Audit: When a $17K Wholesale Fee Still Makes the DSCR Deal Work | Episode 395

    $26,300 cash to close on a $102,000 wholesale DSCR deal. Paper math said 9% return. Real math said he was losing $1,400 a year. Welcome to Real Deal Audit, a new series on Chasing Financial Freedom where Ryan takes an actual DSCR closing and walks through the math on camera the same way he would if you brought it to him at his desk. In this episode, Ryan breaks down the difference between paper cash flow (what most investors calculate) and real cash flow (what actually hits your bank account after operating reserves). He walks through the closing line by line for a sub-$100K wholesale acquisition: $85,000 to the seller, $17,000 to the wholesaler as an assignment fee, and $5,900 in traditional closing costs. Then he shows the sub-$100K rate premium that DSCR lenders never mention (an extra 0.5% on the rate compared to what a $150K+ loan at the same credit tier would be priced at). The episode covers the four numbers every wholesale DSCR investor must calculate before sending the wire: total cash to close, including the wholesale fee; real monthly cash flow after operating reserves; cash-on-cash return using actual invested capital; and breakeven timeline on cash flow alone. Wholesalers are a legitimate part of the industry. Ryan works with wholesalers regularly, and the $17,000 assignment fee on this deal was earned. The issue is that most investors run paper cash flow and never touch the real numbers. This audit shows you what the real numbers look like and provides the framework to decide whether a wholesale deal still makes sense once the fee is included in your cost basis. Wholesale deals are not bad. Wholesale math the investor does not run is bad.

  2. Aug 12

    Tenant Stops Paying: The DSCR Loan Mistake That Wipes You Out Ep 394

    $8,400 out of pocket by month seven. That's what a client of Ryan's paid personally when his tenant stopped paying rent in month four. $5,700 in mortgage payments the tenant should have covered. $1,800 in eviction filing fees. $900 in damage repairs. The tenant wasn't the problem. The loan structure was. In this episode, Ryan breaks down the four financing decisions that determine whether tenant nonpayment is a $6,000 problem or a $73,000 wipeout: reserves at closing, DSCR ratio cushion, loan-to-value structure, and rate structure. He walks through a real client comparison of two investors who owned similar $250,000 duplexes and both had tenants stop paying in month four. One structured the deal with margin and paid $6,300 total. The other structured tight to the lender minimum and lost $73,000 in cash and equity. The episode also covers the vacancy stress test math every investor should run before signing the loan documents (six months full vacancy, twelve months, 15% rent drop, and the compound scenario of rate adjustment plus vacancy). Plus the specific red flags in a loan structure that mean the deal is already too tight to survive real-world tenant issues. Every rental investor deals with tenant nonpayment eventually. It's not a question of if. It's when. The difference is whether the deal can survive it.

  3. Aug 5

    DSCR Loan or Cash? What Every First-Time Rental Investor Gets Wrong Ep 393

    A client called Ryan two months ago, excited about his first rental deal. Duplex in Ohio, $250,000 purchase price, $260,000 in savings ready to go. His plan was to pay all cash, then refinance into a DSCR loan six months later to pull the money back out. Ryan told him to stop. That plan was going to cost him $28,000 he'd never get back. In this episode, Ryan breaks down why DSCR loans are not just refinance products, and why the advice you keep hearing online (buy in cash, then refinance) is wrong for most first-time rental investors. He walks through the two real paths for buying your first rental, when each one actually wins, and a real client comparison that shows how one investor scaled to a second property in four months while the other stayed stuck on his first deal a full year later. The episode covers the four numbers every investor has to run before committing to either strategy: DSCR ratio, loan-to-value, reserves at closing, and the seasoning period. Ryan also reveals the delayed financing trick that lets cash buyers get 75-80% of their money back sooner than the standard 6-month wait, plus the framework rule that decides which path is right for your specific deal. The right question is not cash or DSCR. The right question is how much of your capital you actually need to put into this deal.

  4. Jul 29

    Every Landlord Gets This $250 Mortgage Trick Wrong Ep 392

    You saw the viral video about a $250 mortgage trick that drops your monthly payment by $500. You called your lender to set it up on your rental property. They told you no. Then they hung up. Every loan on your portfolio was disqualified from the recast. Nobody told you why. In this episode, Ryan breaks down exactly why the mortgage recasting trick does not work on rental property loans. Recasting is a conventional loan feature governed by the guidelines of Fannie Mae and Freddie Mac. DSCR loans, non-QM loans, bank statement loans, and portfolio loans do not follow those rules. Most do not offer recasting at all. If your broker mostly does owner-occupied loans, they are giving you conventional advice on a non-QM loan, and it is costing you. He walks through the four things you CAN do: principal curtailment with a payoff strategy, strategic refinance when the math supports it, interest-only restructures for narrow cases, and the rate buy-down move at your next refinance that permanently reduces your payment better than any recast. The episode closes with the framework rule and portfolio audit process every landlord should run this week: pull your loan statements, list every rental loan by rate, balance, payment, and loan type, then rank them from worst to best. The recasting video was designed for a homeowner with one mortgage on their primary residence. You are a landlord with a portfolio. The playbook is different.

  5. Jul 22

    You Own 10 Rentals and You Are Still Broke. Here Is Why Ep 391

    Ten properties. Ten mortgages. Ten tenants paying every single month. Zero cash flow. That is not a real estate problem. It is a financing problem. And it is more common than most investors realize. In this episode, Ryan breaks down the five financing decisions that silently kill rental cash flow: the rate trap, the LTV trap, the wrong product, the front-end and back-end mismatch, and the rate obsession that causes investors to optimize for the wrong thing. He also walks through how to calculate your own DSCR ratio, the same number lenders run on you, and why running it on your own portfolio is the single most important diagnostic tool you are probably not using. The episode closes with a step-by-step portfolio audit: how to pull your loan statements, rank every property by DSCR, identify your refinance candidates, and decide whether a new loan at today's rates actually improves your cash flow long term. Do not buy property 11 until you fix the financing on the ones you already own.

  6. Jul 15

    Hard Money Trap: Why You Can't Refinance Into a DSCR Loan EP 390

    You finished the rehab. The property is rented. You call your lender to refinance into a DSCR loan, and they tell you that you have to bring $15,000 to the closing table out of your own pocket. This is how it happens. In this episode, Ryan breaks down the real difference between hard money loans and fix-and-flip loans, why the choice on the front end directly affects your ability to refinance into DSCR on the back end, and how to run the math before you ever borrow a dollar. He also shares why Zillow will lie to you about rents, how to stress-test your numbers with 5, 10, and 15 percent drops, and the four steps every investor should follow before signing a loan. Plan your exit before your entry.

  7. Jul 8

    Always Get the Inspection Before the Appraisal — Here Is Why Ep 389

    A client of mine just lost a real estate deal because he skipped a $500 inspection and went straight to the appraisal. The appraisal came back subject to, the lender stopped the loan, and now nobody wants to pay for the repairs. In this episode, Ryan breaks down what a subject-to appraisal actually means, the common items that trigger one, and why the inspection would have given the investor full leverage to fix, negotiate, or walk away clean. Ryan also walks through the right order of operations for every investment property deal, so nothing surprises you at the closing table. The inspection is not a contingency. It is the best $500 you will ever spend.

  8. Jul 1

    The LLC Trap: Why Your DSCR Loan Still Puts You Personally at Risk Ep 388

    Most real estate investors form an LLC, thinking it creates a wall between them and their lender. It doesn't. In this episode, Ryan breaks down the reality of personal guarantees on DSCR loans, what they mean, why every lender requires them, and what your LLC actually does and doesn't protect you from. You'll also get the three questions every investor needs to ask before signing a mortgage contract, and a straight answer on whether non-recourse DSCR loans are worth the trade-off. If you've ever closed a deal in your LLC and assumed you weren't personally on the hook, this episode is for you. Topics covered: The LLC myth: what investors get wrong about personal protectionWhat a personal guarantee actually means in plain EnglishWhy DSCR lenders require a personal guarantee even on no-income-doc loansWhat happens when your DSCR loan gets sold in the secondary marketNon-recourse DSCR loans: the real cost of skipping the personal guaranteeThree questions to ask your lender before you sign anythingSubscribe and leave a review if this helped you.

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About

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!

Information

  • Creator
    Ryan DeMent
  • Years Active
    2020 - 2026
  • Episodes
    284
  • Rating
    Clean
  • Copyright
    © Ryan DeMent
  • Show Website
    Chasing Financial Freedom

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