Chasing Financial Freedom

Hosted by Ryan DeMent

Business Investing EducationInterviews guests

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Episodes

274

Latest episode

Jun 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!

Listen to episodes

60 recent

June 10, 2026Episode 38512 min

Conventional vs DSCR: Stop Making This Rate Mistake Ep 385

DSCR loan explained simply. You see a higher DSCR rate and walk away from the deal. That is the mistake costing investors thousands in lost opportunity every single year.In this episode, I break down exactly why DSCR rates are higher than conventional loans, what you are actually paying for, and why that higher rate is often worth every single penny for the investor who wants to scale.If you are buying two or three properties, conventional all day long. Better rate, lower fees, done. But the moment you want to scale past four properties, the moment your DTI caps you out, the moment you need a loan that looks at the asset, not your W-2, DSCR is the only tool that makes sense.In this episode:— Why DSCR rates are higher and what risk the lender is actually taking— DSCR vs conventional loans broken down side by side with real numbers— Why DSCR loans have no scaling cap and conventional loans do— The 1.25 DSCR ratio threshold and why going below it is a deal killer— How your credit score impacts your rate by 25 to 100 basis points— Why DSCR loans closed in an LLC do not report to your credit bureau— The underwriting fee range you should expect and which lenders are overcharging— Three questions you must ask every DSCR broker before you commitIf this saved you from walking away from a good deal, share it with a fellow investor. More tools and resources at trutalk.co

June 3, 2026Episode 38414 min

DSCR Refinance Rejected: Here's What You Got Wrong Ep 384

DSCR refinance deals do not fail by accident. They fail because nobody stress-tested the numbers before the hard money loan was signed.In this episode, I break down a real Cleveland duplex deal. The investor maxed their hard money at 75% LTV. Appraisal came in $15,000 light. Reconsideration of value failed. Now their only exit is a sale. No DSCR refinance. No cash out. No options left.This is happening right now in markets across the country. If you are using hard money or bridge loans to fund your fix-and-flip or buy-and-hold deals, this episode is both your warning and your roadmap.In this episode:— Why 75% LTV kills your DSCR refinance before it starts— How a $15,000 appraisal miss wipes out every exit strategy— The 15 to 20% fudge factor every investor needs in their budget— Why you should never go above 65% LTV on any investment property loan— How to stress test your ARV before you sign anything— What to do when your comps do not match your lender's appraisal— Why multiple exit strategies are never optionalIf this saved you from a bad deal, share it with a fellow investor. More tools and resources at trutalk.co

May 27, 2026Episode 38317 min

Why Every DSCR Loan Estimate Looks Different Ep 383

Every DSCR loan estimate looks different, and most investors have no idea why. That gap costs them thousands at the closing table.In this episode of the Chasing Financial Freedom Podcast, I break down a DSCR loan estimate box by box, Box A through Box J, with zero filter and no agenda. I show you exactly which fees your lender or broker actually controls, which ones are fixed costs of doing business, and the one shady trick some loan officers use to look cheap on paper until you're sitting at closing. After 110 deals closed in the last 24 months with only 2 lost, I've seen every version of this document, and most investors are reading it completely wrong.

May 20, 2026Episode 38213 min

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

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.trutalk.co

May 13, 2026Episode 38111 min

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

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.

May 6, 2026Episode 38013 min

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

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.

April 29, 2026Episode 37913 min

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

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.

April 22, 2026Episode 37814 min

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

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.

April 15, 2026Episode 37715 min

DSCR Loan vs. Local Bank: What Nobody Tells You Before You Sign Ep 377

Your local bank will happily close your first investment loan, but what they will not tell you is that the loan could make your next deal nearly impossible to finance. In this episode of Chasing Financial Freedom, Ryan DeMent walks through the real differences between DSCR loans and conventional bank financing, including how investment loans on your personal credit affect your DTI, what questions to ask both types of lenders before you commit, why 1.25 is the minimum DSCR ratio worth pursuing in today's compressed rent markets, and how to use both lenders as tools rather than choosing one and hoping for the best. If you are serious about building a real estate portfolio and nobody has walked you through this side-by-side comparison yet, this episode will change how you approach every financing decision going forward.

April 8, 2026Episode 37613 min

Your DSCR Loan Was Sold — Hidden Dangers Every Investor Must Know Ep 376

Your DSCR loan will more than likely be sold to a new lender — and when it is, it could show up on your personal credit report even if you've never missed a single payment. In this episode, Ryan walks through a real investor situation, breaks down your rights under the Fair Credit Reporting Act, and gives you the exact steps to dispute errors and protect your credit before your next deal. Subscribe to Chasing Financial Freedom for weekly real estate investing strategies every Wednesday.