Chasing Financial Freedom

Hosted by Ryan DeMent

Business Investing Education

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Episodes

292

Latest episode

Oct 2026

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About the show

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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60 recent

October 21, 2026Episode 4049 min

DSCR Loan No Tax Returns: How Self Employed Investors Qualify on Rent | Ep 404

Can you get a DSCR loan without tax returns? Yes. With a DSCR loan, the rental property's income qualifies you, not your personal tax return. If you're self-employed, your tax return is built to save taxes, not to buy rentals. In this episode, Ryan walks through an example investor who shows $18,000 of income on his tax return and still qualifies for a $300,000 rental. You'll learn: Why your tax return works against you as a self-employed investor How the rent covers the payment, and what a 1.39 ratio means What to do when the rent is thin, and how more down moves a 1.17 up to 1.25 What some programs look at on credit, cash to close, and reserves How the appraiser estimates market rent on the property Four steps to take before you apply The numbers in this episode are an example for illustration only. Every program is different, so talk to a licensed loan officer about your own situation. More tools and episodes at trutalk.co

October 14, 2026Episode 4039 min

DSCR Cash Out Refinance: How Much Equity You Can Actually Pull | Episode 403

Your $180,000 of equity may turn into only $95,000 of cash on a DSCR cash-out refinance, and that gap lands right when you were counting on the money for your next deal. This episode shows you the math. Take the value, multiply it by the program's loan-to-value cap, and subtract what you owe. Say a rental is worth $340,000 and you owe $160,000. At 75%, that is $255,000 minus $160,000, or $95,000. Then the lender tests the rental again on the new, larger payment. Say the ratio goes from 1.76 to 1.24, and a program that wants 1.25 would cap your cash at a lower amount. You will also hear how seasoning, which is how long you have owned the property, can change the value the program uses, and what the cash costs you in loan costs, a higher payment, and a thinner equity cushion. You leave with five steps to run on your own rental before you count on the cash. Your cap, minimum DSCR, and how long you have owned the property depend on the program and the rental. Run your own numbers before that cash goes into your next deal.

October 7, 2026Episode 40211 min

Before You Offer on a Rental: Run the DSCR the Way Underwriting Will Ep 402

Run the DSCR the way underwriting will before you offer on a rental, so the ratio you close on is the one you live with. In this episode, Ryan opens with one hypothetical rental: a 1.33 DSCR on the spreadsheet that drops to 1.11 once the lender's numbers go in. Same house, same loan, four inputs. He walks through each. Rent: why the lender uses supportable rent from the appraisal or lease, and how to run the ratio three ways, including a vacancy month stress test. Taxes: why the seller's bill is not yours, and the three questions to ask the assessor. Insurance: why you need a bindable landlord quote before your inspection window closes, and how it hits cash to close. HOA: why a bigger down payment cannot shrink dues, and what to search for in the reserve study and board minutes. He closes with the check: run the lowest of your three ratios before you offer.

September 30, 2026Episode 4017 min

Bridge Loans Explained: How to Buy Your Next Rental Before You Sell Ep 401

Bridge loans explained: how to buy your next rental before you sell the one you already own. Here is exactly how the equity gets unlocked. In this episode, Ryan lays out the entire bridge loan model in the first minute, then walks through each piece. A bridge loan borrows against the equity you already have in your current rental, typically 70 to 80 percent, so you can move on a new deal now instead of waiting months for a buyer. He covers how the loan is secured against your existing equity, what it actually costs to carry (short-term, interest-only, 6 to 12 months, and the rate premium you trade for speed), the two ways you pay it off (selling the old property or refinancing the new one), and exactly when a bridge loan is the right call versus when it turns a good deal into a stressful one, including how it is different from hard money. He closes with the four-step framework: confirm your real usable equity, line up the new deal's numbers against the carrying cost, have a real exit, and budget for both payments for the full term. Know your usable equity, know what it costs to carry, and know your exit before you use a bridge loan.

September 23, 2026Episode 4008 min

Fix and Flip Loans for Beginners: What You Need to Fund Your First Deal Ep 400

Fix and flip loans for beginners: what you need to fund your first deal, and why you do not need all the cash yourself. Here is how the money really works. In this episode, Ryan lays out the entire fix-and-flip loan model in the first minute, then walks through each piece. A fix and flip loan funds most of your purchase and your rehab, built around the after-repair value (ARV), not just what you pay today, which is why most first-time flippers who think they need all the cash are wrong. He covers what the loan actually funds (up to about 90 percent of purchase, up to 100 percent of rehab, capped at roughly 70 percent of ARV), the draw process that trips up every first-timer (the rehab money comes back in pieces, so you front each stage and get reimbursed after inspection), the carrying costs that eat your profit the longer you hold, and what you actually need to qualify: down payment, credit, experience, reserves, and a deal that pencils, with no tax returns. He closes with your two exits: sell the flip and keep the spread, or refinance into a long-term DSCR loan and keep the property as a rental- the bridge from flipping into a rental portfolio. You do not need all the cash to fund your first flip.

September 16, 2026Episode 3997 min

DSCR Loan Requirements: Everything You Need to Qualify for a Rental Ep 399

DSCR loan requirements: everything you need to qualify for a rental, all five laid out fast. No tax returns, no W-2, no personal income. In this episode, Ryan lays out the complete DSCR loan requirements checklist in the first minute, then walks through each one. A DSCR loan does not care what you make. It cares whether the property makes money, which is why an investor whose tax returns make them look broke on paper can still qualify. He covers the five requirements in order: your credit score and why pushing from 680 to 700 is the cheapest money you will ever make; the DSCR ratio and why 1.25 is the target and what happens as you drop toward breakeven; the 20 to 25 percent down payment and why that is not the same as your cash to close; the six months of PITIA reserves that trip up first-time investors the most; and the business-purpose requirement that lets the loan skip your personal income entirely. He also spells out everything that is NOT required: tax returns, W-2s, pay stubs, bank statements, and personal debt-to-income. The episode closes with a five-item self-check to run before you ever call a lender. The property has to make money. You do not have to prove that you do.

September 9, 2026Episode 3988 min

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

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.

September 2, 2026Episode 3979 min

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

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.

August 26, 2026Episode 39610 min

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

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.

August 19, 2026Episode 39513 min

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.

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