Ryan Richards

The Long Game by Ryan Richards

Business EN ↓ 92 episodes

The Long Game by Ryan Richards is a podcast about how real operators think, decide, and build for the long term — and what actually happens behind the scenes when the stakes are real. Narrated and hosted by Ryan Richards, the show pulls back the curtain on business, real estate, and investing through unfiltered conversations with operators, investors, and builders who have earned their perspective. You’ll hear what worked, what didn’t, and the decisions most people never see or talk about publicly. This isn’t surface-level advice or polished success stories. It’s a fly-on-the-wall look at high...

Author

Ryan Richards

Category

Business

Podcast website

www.trynorthpoint.com

Latest episode

Jul 7, 2026

Where to listen?

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Episodes

Ep. #67 | When Does It Make Sense to Sell a Rental Property? 23.12.2025

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 b...

Ep. #66 | Capital Expenditures: Planning for Unexpected (And Expected) Repairs 17.12.2025

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...

Ep. #65 | From Nurse to Real Estate Investor: How Abigail Bought Her First Multifamily at 24 09.12.2025

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...

Ep. #64 | How AI and Automation Are Reshaping Small Business Systems with Bryce Meizen 02.12.2025

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 desi...

Ep. #63 | From Payroll Sales to Full-Time Real Estate Investor with Wendell Butler 25.11.2025

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...

Ep. #62 | Closing Costs 101: What You’ll Really Pay at the Closing Table 18.11.2025

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...

Ep. #61 | 2008 Again? Not in New England. 11.11.2025

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 be...

Ep. #60 | Why Mortgage Rates Went Up After the Fed Cut Interest Rates 04.11.2025

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...

Ep. #59 | The #1 Reason Buyers Get Denied for a Mortgage 28.10.2025

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...

Ep. #58 | How to Analyze a Real Estate Deal in 60 Seconds 21.10.2025

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 f...

Ep. #57 | Our First "Informed Investor" Mastermind Success Story 14.10.2025

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-famil...

Ep. #56 | How to Start Investing in Real Estate (Step-by-Step) 07.10.2025

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 paym...

Ep. #55 | Residential vs. Commercial Financing 101: Key Differences 30.09.2025

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 portfol...

Ep. #54 | Investing Out of State and Building a 50-Unit Portfolio with Jessie Dillon 24.09.2025

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 sel...

Ep. #53 | Breaking Free from Analysis Paralysis in Home Buying 16.09.2025

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 opportun...

Ep. #52 | What Realtors Need to Know About Mortgages 09.09.2025

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 diffe...

Ep. #51 | 3 Mortgage Hacks Every Homeowner Should Know 02.09.2025

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 you...

Ep. #50 | Refinancing 101 | How to Know if It’s Worth It 26.08.2025

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 sim...

Ep. #49 | Navigating Complex Deals and Market Shifts with Spenser Molloy, Next Home Realty 19.08.2025

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 br...

Ep. #48 | How Home Insurance Can Impact Your Real Estate Deal 12.08.2025

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 c...

Ep. #47 | Building Teams, Scaling Impact, and Navigating the 2025 Real Estate Market with Ben Carbone 05.08.2025

In this episode of The Real Estate Lens , Ryan Richards sits down with returning guest Ben Carbone of the We Close Deals team at Lamacchia Realty for a deep dive into entrepreneurship, market strategy, and the realities of building a team. Since Ben’s last appearance, a lot has changed—he’s switched brokerages, launched a team that’s already grown to 17 agents, and doubled down on impact through r...

Ep. #46 | Inside the Home Inspection Business with Mike Sweeney of House Doctor Home Inspections Inc. 30.07.2025

In this episode of The Real Estate Lens , Ryan Richards sits down with Mike Sweeney, owner of House Doctor Home Inspections—serving Rhode Island, Massachusetts, and Connecticut. From real estate investing to leadership to the nuts and bolts of the home inspection process, this episode goes deep into the business of protecting homebuyers and scaling a service-driven company. Mike shares how he went...

Ep. #45 | How to Get Financing as an Entrepreneur or Independent Contractor 22.07.2025

In this solo episode of The Real Estate Lens , Ryan dives into one of the most common challenges he sees among real estate investors, flippers, and business owners: how to qualify for a mortgage when your tax returns don’t show enough income. Ryan breaks down two powerful lending options his team uses to help clients with non‑traditional income secure financing. Whether your business write‑offs le...

Ep. #44 | Lessons from My First Single-Family Flip: What I Got Right, What I’d Do Differently 15.07.2025

In this solo episode of The Real Estate Lens , Ryan Richards shares his honest, behind-the-scenes experience flipping a single-family home for the first time. From budget overruns to unexpected code violations, Ryan walks through what worked, what didn’t, and the real numbers that shaped the outcome of the project. Whether you’re planning your first flip or just curious about the realities of mana...

Ep. #43 | Why Everyone’s Moving to Rhode Island, with Brooke Buckett 08.07.2025

In this episode of The Real Estate Lens , Ryan welcomes back top Rhode Island real estate agent Brooke Buckett for her third appearance on the show. Brooke specializes in relocation and first-time homeownership, and in this conversation, she breaks down why Rhode Island continues to attract buyers from across the country—and how to navigate a multi-state move without the stress. Brooke and Ryan di...

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