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The Long Game by Ryan Richards
Ryan Richards
67 episodes
6 days ago
One of the hardest decisions in real estate investing is knowing when to hold and when to sell. In this solo episode of The Real Estate Lens, investor Ryan Richards breaks down how to evaluate whether a rental property is truly performing or if your equity could be working harder somewhere else. Ryan walks through a real-world example of an investor holding a property with a great interest rate but poor returns, and explains why focusing on return on equity, not emotional attachment or low ra...
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Entrepreneurship
Business,
Investing
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One of the hardest decisions in real estate investing is knowing when to hold and when to sell. In this solo episode of The Real Estate Lens, investor Ryan Richards breaks down how to evaluate whether a rental property is truly performing or if your equity could be working harder somewhere else. Ryan walks through a real-world example of an investor holding a property with a great interest rate but poor returns, and explains why focusing on return on equity, not emotional attachment or low ra...
Show more...
Entrepreneurship
Business,
Investing
Episodes (20/67)
The Long Game by Ryan Richards
When Does It Make Sense to Sell a Rental Property?
One of the hardest decisions in real estate investing is knowing when to hold and when to sell. In this solo episode of The Real Estate Lens, investor Ryan Richards breaks down how to evaluate whether a rental property is truly performing or if your equity could be working harder somewhere else. Ryan walks through a real-world example of an investor holding a property with a great interest rate but poor returns, and explains why focusing on return on equity, not emotional attachment or low ra...
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2 weeks ago
11 minutes

The Long Game by Ryan Richards
Capital Expenditures: Planning for Unexpected (And Expected) Repairs
If you own rental properties long enough, it's not a matter of if something breaks - it's when. In this solo episode of the Real Estate Lens, multi-family investor Ryan Richards breaks down the reality of repairs, maintenance, and capital expenditures that come along with rental property ownership. Ryan shares what he is dealing with right now across his own portfolio in early December 2025, including replacing a six-unit boiler system, and explains how better underwriting, early planni...
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3 weeks ago
15 minutes

The Long Game by Ryan Richards
From Nurse to Real Estate Investor: How Abigail Bought Her First Multifamily at 24
In this episode of The Real Estate Lens, host Ryan Richards sits down with Abigail Chrisafideis with the We Close Deals team at Lamacchia Realty, a registered nurse turned real estate agent and investor, to unpack her journey from healthcare to homeownership and beyond. Abigail shares how she bought her first multifamily property at just 24 years old, guided by mentorship from her uncle, and how that single decision changed the trajectory of her financial future. Together, she and Ryan dive i...
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1 month ago
59 minutes

The Long Game by Ryan Richards
How AI and Automation Are Reshaping Small Business Systems with Bryce Meizen
In this episode of The Real Estate Lens, Ryan Richards sits down with Bryce Meizen, Founder and CEO of Jidoka LLC, a Worcester County–based custom software and AI integration agency helping small and medium-sized businesses streamline operations, automate workflows, and scale smarter. Bryce shares how his background in software development and entrepreneurship led him to build a company that designs tailored systems, from CRM integrations and quote automation to full-scale AI assistants that ...
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1 month ago
1 hour

The Long Game by Ryan Richards
From Payroll Sales to Full-Time Real Estate Investor with Wendell Butler
In this episode of The Real Estate Lens, host Ryan Richards sits down with Wendell Butler - President and Founder of Hammerhead Capital and Flip Fuel Lending - to unpack his journey from the corporate world to full-time real estate investing in Charlotte, NC. Wendell shares how leaving a stable sales career to pursue fix-and-flips and new construction projects transformed his approach to business, risk, and systems. Together, he and Ryan dive into what it really takes to go all-in on investin...
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1 month ago
1 hour

The Long Game by Ryan Richards
Closing Costs 101: What You’ll Really Pay at the Closing Table
In this solo episode of The Real Estate Lens, Ryan breaks down exactly what closing costs are, how they’re calculated, and why they vary from deal to deal. If you’re budgeting to buy in Massachusetts or Rhode Island and only planning for the down payment, this episode shows you what else to expect so there are no surprises on closing day. Ryan walks through the two big buckets of costs: loan costs tied to your mortgage, and “other” costs like attorney, title, taxes, insurance, and escrows. He...
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1 month ago
12 minutes

The Long Game by Ryan Richards
2008 Again? Not in New England.
In this solo episode of The Real Estate Lens, Ryan Richards tackles the question on everyone’s mind: are we headed for a housing crash like 2008, or will prices hold firm? Pulling from lending data, supply and demand dynamics, and on-the-ground trends, Ryan explains why today’s market looks very different from the last crash and why outcomes are highly local. He breaks down why the Northeast is behaving differently from many Sun Belt and Western markets, how tighter post-2008 underwriting and...
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2 months ago
21 minutes

The Long Game by Ryan Richards
Why Mortgage Rates Went Up After the Fed Cut Interest Rates
In this solo episode of The Real Estate Lens, Ryan Richards unpacks one of the most confusing moments in the financial world: when the Federal Reserve cuts interest rates but mortgage rates still rise. If you’ve ever wondered why those two numbers don’t always move together, this episode breaks it all down in plain English. Ryan explains the real difference between the Fed funds rate and mortgage rates, what drives the 10-year Treasury yield, and how investor sentiment, inflation expectations...
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2 months ago
12 minutes

The Long Game by Ryan Richards
The #1 Reason Buyers Get Denied for a Mortgage
In this solo episode of The Real Estate Lens, Ryan Richards breaks down the single biggest reason homebuyers get denied financing - communication - and how to prevent it. Whether you’re a first-time buyer, investor, or real estate agent guiding your clients, this episode reveals what really causes pre-approvals to fall apart and how to spot the warning signs early. Ryan explains why most denials come down to poor communication and lack of due diligence, often from both sides. He shares real-w...
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2 months ago
9 minutes

The Long Game by Ryan Richards
How to Analyze a Real Estate Deal in 60 Seconds
In this solo episode of The Real Estate Lens, Ryan Richards shares his quick-hit system for analyzing investment properties in under a minute. With deals constantly flooding your inbox, knowing how to spot opportunities — and avoid time-wasters — is key. Ryan breaks down the three simple metrics he uses to instantly evaluate whether a deal is worth pursuing. He explains how to apply the 1% rule for quick cash flow analysis, spot hidden value in underutilized square footage, and use cost-per-u...
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2 months ago
10 minutes

The Long Game by Ryan Richards
Our First "Informed Investor" Mastermind Success Story
In this solo episode of The Real Estate Lens, Ryan Richards shares a real-life success story from one of his Informed Investor Mastermind students who went from beginner to buying two multifamily properties in under a year — all while using minimal cash out of pocket. Ryan walks through the exact steps this couple followed: from attending the 12-week mastermind, purchasing their first three-family property with just 3.5% down, to building systems for management, renovations, and cash flow. Te...
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2 months ago
6 minutes

The Long Game by Ryan Richards
How to Start Investing in Real Estate (Step-by-Step)
In this solo episode of The Real Estate Lens, Ryan Richards breaks down exactly what he would do if he were starting his real estate investing journey today. Whether you’ve been saving for your first multifamily property or just starting to explore real estate as a wealth-building tool, this episode walks through a clear, actionable plan to get started. Ryan explains how to leverage low down payment options, live in your investment to gain hands-on experience, and use strategic renovations to...
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3 months ago
10 minutes

The Long Game by Ryan Richards
Residential vs. Commercial Financing 101: Key Differences
In this solo episode of The Real Estate Lens, Ryan Richards unpacks the major differences between residential and commercial financing and how each impacts your real estate investment strategy. Drawing on his experience as both a loan officer and an investor, Ryan shares the pros, cons, and real-world applications of each type of financing so you can make smarter decisions as you grow your portfolio. From qualification standards to property valuation methods, he explains how residential loans...
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3 months ago
9 minutes

The Long Game by Ryan Richards
Investing Out of State and Building a 50-Unit Portfolio with Jessie Dillon
In this episode of The Real Estate Lens, Ryan Richards sits down with Massachusetts-based entrepreneur and investor Jessie Dillon to unpack her rapid journey from beauty industry business owner to powerhouse real estate investor. Jessie recently hit her milestone of 50 units owned and operated, many of them in states she hasn’t even visited, and is now shifting focus to her next big venture in self-storage. Jessie shares how she went from burning out behind the chair in her permanent makeup s...
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3 months ago
51 minutes

The Long Game by Ryan Richards
Breaking Free from Analysis Paralysis in Home Buying
In this solo episode of The Real Estate Lens, Ryan takes on a common trap many buyers fall into: overanalyzing every detail of a home purchase until they talk themselves out of moving forward. Ryan explains why buying a primary residence is different from making an investment decision and why focusing too much on spreadsheets, projections, or trying to “time the market” can lead to missed opportunities. He shares real client examples of people who lost out on great deals because they were cha...
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3 months ago
9 minutes

The Long Game by Ryan Richards
What Realtors Need to Know About Mortgages
In this solo episode of The Real Estate Lens, Ryan breaks down the key things every real estate agent should understand about mortgages to better guide their clients and strengthen offers. Instead of jargon and technical guidelines, Ryan focuses on strategy and the practical insights that matter most when you’re representing buyers or sellers. He explains how to interpret pre-approvals, what different financing types mean for a transaction, and how to avoid common misconceptions that can crea...
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4 months ago
16 minutes

The Long Game by Ryan Richards
3 Mortgage Hacks Every Homeowner Should Know
In this solo episode of The Real Estate Lens, Ryan Richards shares three powerful strategies homeowners can use to save money, pay off their mortgage faster, and avoid costly mistakes that lenders don’t always talk about. Ryan breaks down how small, proactive steps can add up to massive savings over the life of your loan, whether you plan to stay in your home long term or just want to position yourself for future opportunities. What you’ll learn: How one extra payment a year can cut six years...
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4 months ago
8 minutes

The Long Game by Ryan Richards
Refinancing 101 | How to Know if It’s Worth It
In this solo episode of The Real Estate Lens, Ryan breaks down one of the biggest financial questions homeowners face: does it make sense to refinance right now? With mortgage rates hitting their lowest point of 2025, many borrowers are wondering whether they should act or wait. Ryan explains why a refinance is more than just a rate play—it’s an investment with a measurable return. He shares a simple framework you can use to calculate costs, savings, and breakeven points, so you can confident...
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4 months ago
12 minutes

The Long Game by Ryan Richards
Navigating Complex Deals and Market Shifts with Spenser Molloy, Next Home Realty
In this episode of The Real Estate Lens, Ryan Richards is joined by returning guest Spenser Molloy, a real estate agent with Next Home Realty based in Lebanon, New Hampshire. Together, they pull back the curtain on the real estate process—where not every deal is smooth, and sometimes major challenges arise that can put deposits, financing, and even entire transactions at risk. Ryan and Spenser break down a recent set of complex transactions that nearly fell apart, and how having the right tea...
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4 months ago
1 hour 4 minutes

The Long Game by Ryan Richards
How Home Insurance Can Impact Your Real Estate Deal
In this solo episode of The Real Estate Lens, Ryan Richards breaks down a topic that’s often overlooked but can have a huge impact on your mortgage approval and investment returns: home insurance. Drawing from his experience as a residential loan officer and real estate investor in Massachusetts and Rhode Island, Ryan explains how insurance premiums are estimated during the lending process, why certain properties can cause costs to skyrocket, and what every buyer should look out for before ma...
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5 months ago
10 minutes

The Long Game by Ryan Richards
One of the hardest decisions in real estate investing is knowing when to hold and when to sell. In this solo episode of The Real Estate Lens, investor Ryan Richards breaks down how to evaluate whether a rental property is truly performing or if your equity could be working harder somewhere else. Ryan walks through a real-world example of an investor holding a property with a great interest rate but poor returns, and explains why focusing on return on equity, not emotional attachment or low ra...