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Chasing Financial Freedom

Ryan DeMent
Chasing Financial Freedom
Latest episode

287 episodes

  • Chasing Financial Freedom

    DSCR Loan Down Payment: How Much Cash to Close on a Rental Ep 398

    09/09/2026 | 8 mins.
    DSCR loan down payment: how much cash to close you really need on a rental, not just the twenty percent down everybody budgets for. Here is the real number before it costs you a deal.
    In this episode, Ryan breaks down why twenty percent down was never your real number. Your down payment is one of three buckets. Cash to close is your down payment, plus closing costs, plus the reserves you have to prove in the bank, and first-time investors get caught by the gap right before closing.
    He covers what a DSCR down payment actually costs and what sets your tier; the closing costs and reserves most lenders never warn you about; and the levers that move your down payment up or down: your credit score, the property's DSCR ratio, the property type, and the loan size. He walks through why a smaller loan costs a bigger percentage, why six months of PITIA in reserves can make or break your file, and how pushing your credit up one band before you apply is the cheapest money you will ever make.
    The episode closes with the four steps to know your true cash to close before you ever write the offer.
    The down payment is what everybody plans for. The cash to close is what actually gets the deal done.
  • Chasing Financial Freedom

    DSCR Loan for Airbnb: How to Finance Your First Short-Term Rental Ep 397

    02/09/2026 | 9 mins.
    DSCR loan for Airbnb: how to finance a short-term rental on the property's income instead of your tax returns. This investor's Airbnb cleared $4,200 a month, and the bank still said no.
    In this episode, Ryan breaks down how a DSCR loan finances a short-term rental when a conventional loan cannot. The bank qualifies you based on your tax returns, your debt-to-income ratio, and your W-2, so a smart investor who writes off heavily looks broke on paper and gets declined. A DSCR loan ignores all of that and qualifies on whether the property's rental income covers the payment.
    He covers the short-term-rental-specific mechanics most lenders never explain: how an appraiser values Airbnb income, the difference between the long-term 1007 rent schedule and actual short-term revenue, when a lender will use an AirDNA report or booking history, and the exact question to ask before you write the offer. He also walks through the realities of the down payment, reserves, and DSCR ratio for a short-term rental, including the seasonality trap that catches investors who only underwrite the peak season.
    The episode closes with the four steps to get approved for the property's income, even when your tax returns show you make nothing.
    The bank asks what you make. A DSCR loan asks what the property makes.
  • Chasing Financial Freedom

    Real Deal Audit: $26K Down, $38K to Close on a DSCR Rental Ep 396

    26/08/2026 | 10 mins.
    A first-time investor budgeted $26,000 for his down payment and wired over $38,000 at the closing table. Here is where the extra cash came from.
    This is Real Deal Audit, the series on Chasing Financial Freedom where Ryan takes a real 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 five things your real cash to close is actually made of: the down payment, lender fees (origination, processing, underwriting, appraisal), title and closing costs, prepaids and impounds, and the hidden wholesale spread. On this $130,000 deal, the fee stack added over $12,000 on top of the down payment, and $15,000 of the purchase price was a wholesale spread baked in that the buyer financed for 30 years without ever seeing it itemized.
    He closes with the four questions every investor should run before writing an offer: what is your all-in cash to close, what do closing costs and prepaids actually run, do you know the true value or just the quoted price, and do you still have reserves after you bring cash to close.
    Wholesalers are a legitimate part of the business. The spread was earned. The lesson is that the down payment is never the cash to close, and the investor who runs the real numbers before falling in love with the property is the one who never gets blindsided at the wire.
    Fall in love with the math, not the property.
  • Chasing Financial Freedom

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

    19/08/2026 | 13 mins.
    $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.
  • Chasing Financial Freedom

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

    12/08/2026 | 10 mins.
    $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.
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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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