The Long Game by Ryan Richards

Ryan Richards
  • 5.0 (4)
  • Entrepreneurship
  • Semiweekly

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-caliber conversations — the mental models, systems, mistakes, and tradeoffs that shape durable success over time. Through solo reflections and deep conversations, The Long Game gives listeners proximity to real operators and the clarity that comes from understanding how the best actually think, judge risk, and execute. If you’re an ambitious builder who wants to learn from real experiences — not shortcuts or hype — this is an invitation inside. Welcome to The Long Game.

  1. 4d ago

    Real Estate Horror Stories - The Long Game - Ep. #109

    What would you do if your financing contingency passed and your $10,000 deposit went with it? In this episode of The Long Game Podcast, Ryan shares three real stories from the past year to mark Halloween: a buyer who lost an earnest money deposit, a near miss with vacant land fraud, and an investor stretched too thin. The goal is practical lessons you can use before the same thing happens to you. What You'll Learn: Why an underwriting-backed pre-approval protects you in ways a quick online pre-approval can’tWhat a financing contingency is, why the date matters, and how to protect your deposit if you’re not ready to commitWhy your lender should flag your commitment dates before they arrive, and what to ask yours up frontThe warning signs of vacant land fraud, including a listing agent who has never spoken with the sellerHow to verify wire instructions by phone, and why the first 30 minutes after sending a wire matter mostWhy your numbers need to hold up in the worst case, not just the best caseHow much liquidity to keep on hand as an investor, and what one bad month looks like when an eviction, a boiler, and legal fees stack up If you’re buying a home, wiring money for a closing, or building a rental portfolio, this episode will help you spot the costly mistakes before they happen. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in CT, FL, MA, ME, NH, RI, NC, PA, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Halloween Money Nightmares 00:37 Preapproval Gone Wrong 02:06 Protect Your Deposit 03:23 Vacant Land Scam 05:00 Wire Fraud Warning 06:52 Overleveraged Investors 08:35 Stress Test Your Rentals 10:03 Get Help Early 10:35 Final Halloween Sendoff

  2. Oct 27

    Navigating a Shifting Real Estate Market - The Long Game - Ep. #108

    Is now actually a bad time to buy real estate, or does it just look that way from the headlines? In this episode of The Long Game Podcast, Ryan breaks down what’s actually happening in the real estate market right now, filmed in mid-October 2026, and why the conditions most buyers are treating as a reason to wait are the same conditions that create real opportunities for the people paying attention. Ryan cuts through the noise on two fronts: rates and seasonality. The average 30-year fixed rate has climbed nearly a full percent in the last 90 days, and the market is heading into its naturally slower fall cycle. Transactions are at some of the lowest levels in years, and most people read those headlines and sit on the sidelines. What You'll Learn: Why low transaction volume and rising rates create buyer leverage that hasn’t existed in years, and how to use itHow to use a seller credit to recreate the same monthly payment you would have had when rates were lowerThe side-by-side math on a $475,000 offer versus a $500,000 offer with a $25,000 credit, and why the higher price often winsHow temporary rate buydowns work and why some buyers are getting rates in the fours in today’s marketWhy commercial real estate values are softening and what that means for multifamily investors looking for a discounted entry pointThe difference between buying to flip in today’s market versus buying a long-term hold, and why the strategy has to match the timelineWhy trying to time the market is the wrong question, and what to focus on instead If you’ve been watching the headlines and talking yourself out of making a move, this episode gives you the framework to stop reacting to the noise and start looking at what’s actually available in today’s market. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in CT, FL, MA, ME, NH, RI, NC, PA, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Headlines vs Reality 01:15 Market Forces Today 02:24 Mindset for Buyers 03:09 Negotiating Seller Credits 05:05 Credits vs Price Cut Math 06:34 Temporary Rate Buydowns 07:25 Commercial Investing Angle 08:44 Stop Timing the Market 09:55 Wrap Up and Next Steps

  3. Oct 20

    99% of AI Content Is a Complete Waste of Time… with Bruno Maluf - The Long Game - Ep. #107

    What does it take to go from flipping houses to moving over a million square feet of flooring across New England? In this episode of The Long Game Podcast, Ryan sits down with Bruno Maluf, owner of LVP Direct, a direct-to-consumer luxury vinyl plank company selling wholesale-priced flooring across New England, to talk about how a frustrating supply chain problem on a flip turned into a business doing millions in revenue, and what it actually took to get there. Ryan and Bruno go deep on the conversations most entrepreneurs avoid: the relationship between personal development and business growth, why tracking your macros and going to the gym compounds into every other area of your life the same way consistent business habits do, and why most people’s relationship with AI right now looks a lot like the NFT boom did a few years ago.  Bruno’s take is direct: most AI use cases are noise, the real leverage is in applying it to your health and your personal systems first, and the fundamentals of showing up, building skills, and not chasing shortcuts still win every time. What You'll Learn: How Bruno identified a real market problem on his twelfth flip and turned it into a direct-to-consumer flooring business doing over a million square feet in salesWhy wiring six figures to a factory in Vietnam he’d never visited was the right call, and how he thought about the riskHow one unscripted, low-effort video filmed after the gym generated 125,000 views and over 1,300 qualified leads on a single organic postWhy organic content is the best testing ground for paid ads, and how Bruno scaled what was already working rather than starting from scratchThe personal development and income relationship that Jim Rohn describes and Bruno has lived: why your income rarely exceeds your level of personal growth for longWhy Bruno thinks 99% of AI use cases are noise right now, and what he actually uses it for insteadHow to use AI as a tool to challenge your own thinking rather than confirm it, and why that distinction matters more than most people realizeWhy Bruno is deliberately staying dense in Connecticut, Massachusetts, and Rhode Island rather than expanding laterally, and what 5% market share in those three states actually represents If you’re building a product or service business and trying to figure out how to go from idea to traction without a massive budget or team, this episode is a candid and energizing look at what that process actually requires. Interested in connecting? GUESTS Bruno Maluf Founder & President, LVP Direct  Bruno@WeGotFloors.com | wegotfloors.com  Instagram: @brunobuyshouses HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Welcome and Guest Intro 01:31 Bruno Background in Real Estate 03:04 Flooring Pain Points Spark Idea 04:50 First Import and Market Proof 07:35 Launching LVP Direct for Real 10:32 Why He Left House Flipping 12:08 Social Media as a Flywheel 19:14 Organic Content to Paid Ads 22:45 Scaling Vision and Logistics 26:30 Focus and Avoiding Shiny Objects 28:41 Personal Development Mindset 30:31 Gym Discipline as Life Anchor 33:47 Extra Mile Mindset 34:29 Power of One More 35:30 Tracking Nutrition Wins 37:40 No Secret to Success 38:55 Real Estate vs Hype 44:56 Trading Is Gambling 48:15 AI Confirmation Bias 49:20 Using AI for Health 52:42 Whisper Flow Demo 54:59 AI in CRM Workflows 59:10 AI Slop Backlash 01:01:29 Closing Thoughts

  4. Oct 13

    Your Next Hire Should Be a Swiss Army Knife - Ep. #106

    What if the role you’ve been struggling to fill doesn’t have to fit into one lane? In this episode of The Long Game Podcast, Ryan shares the framework that unlocked his approach to building a team, and why the single biggest mistake entrepreneurs make when looking for their first or next hire is thinking about the role in one dimension. Ryan makes the case that the “I need to hire an admin” or “I need to hire a salesperson” mindset is exactly what keeps solo operators stuck. If you can only picture a hire filling one lane, it becomes almost impossible to justify the headcount, because how do you fill a 40-hour week with just one type of task? The unlock is realizing that the same way you taught yourself marketing, sales, admin, and operations from scratch, you can hire someone and teach them to do the same. What You'll Learn: Why thinking about your next hire in a single lane is the framework that keeps most entrepreneurs from pulling the triggerHow Ryan’s executive assistant went from an undefined role to handling four distinct areas of his business, and what that process actually looked likeWhy the same logic that made you a capable solo operator applies directly to the people you can hire and trainHow to frame a multi-skilled role in the hiring process so it attracts the right type of person rather than scaring them offWhy some roles call for incentive-based compensation and others call for salary stability, and how to match the package to the person you actually needWhat the people who thrive in Swiss Army knife roles have in common, and why they often choose smaller teams over bigger companies on purposeWhy the goal isn’t to find the perfect hire. It’s to frame the right role and let the right person find you If you’re running your business alone or with a small team and keep talking yourself out of the next hire, this episode gives you a direct and practical reframe for how to think about what that role could actually be. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in CT, FL, MA, ME, NH, RI, NC, PA, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Solo Founder Overload 00:57 Hiring Before Burnout 01:14 Stop One Hat Thinking 02:18 Swiss Army Assistant Story 03:40 Real Hiring Conversation 04:24 Attract Multifaceted Talent 05:54 Compensation Role Fit 06:29 Find Builders Not Specialists 07:41 Closing Takeaway

  5. Oct 6

    The Habits That Drive 80+ Sales a Year with Rich Jenkins - The Long Game - Ep. #105

    Eight years, 60 units, and 80+ homes a year. Here's what the market actually looks like from the inside. In this episode of The Long Game Podcast, Ryan sits down with Rich Jenkins, a top real estate agent in Central Massachusetts selling over 80 homes per year and a real estate investor with 60 units across Worcester County, to talk about what the market looks like heading into fall 2026, how buyers and investors are winning right now, and what separates the agents and advisors who build long-term clients from the ones who close a deal and disappear. Ryan and Rich also dig into the investor side of the conversation: how Rich thinks about cash flow versus what most newer investors call cash flow, why his underwriting is more conservative than most banks, and how first-hand experience owning 60 units makes him a fundamentally different advisor for his investor clients than someone who's never been through an eviction, a bad prepay, or a tenant who hasn't paid since November. What You'll Learn: Why joining a team was the highest-leverage move Rich made when he started, and what most new agents get wrong by trying to figure it out aloneHow Rich protects his lead generation time from 9 to noon, five days a week, and why that consistency is the unsexy thing that actually moves the needleWhat the Worcester County market looks like heading into fall 2026: more inventory, more buyer leverage, and sellers who still haven't let go of 2021Why Rich starts every investor conversation with "what's your goal?" instead of "how much money do you have?", and why that question changes everythingWhat cash flow actually means when you account for vacancies, capital improvements, water, sewer, and the boiler that's going to go eventuallyWhy a $10,000 seller credit put toward a rate buydown is almost always worth more than a $10,000 price reduction, and how Rich walks clients through that mathWhat Rich's best clients say about him that he wishes every client knew from day oneWhy Rich says his job doesn't really start until after closing, and what that looks like in practice If you're buying, selling, or investing in Central Massachusetts and want to understand what an experienced agent and investor brings to the table that most people never even think to ask for, this episode gives you a clear and direct picture of what that actually looks like. Interested in connecting? GUESTS Rich Jenkins REALTOR, Jim Black Group  rich@jimblackgroup.com | richjenkins.jimblacksellshomes.com  Instagram: @richjenkinsrealtor HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Market Shift Overview 00:10 Meet Rich Jenkins 01:59 From Hospitality to Real Estate 03:35 Service Skills That Transfer 05:17 Early Career Lessons 06:07 Why Joining a Team Wins 08:40 Time Blocking Lead Gen 12:52 Building Personal Systems 14:06 Scaling as an Investor 19:07 Investor Advice and Goals 21:11 Investor vs Homebuyer Mindset 23:23 Making Deals Work Today 25:35 Real Cash Flow Explained 27:03 Build the Right Team 27:51 Market Shift Since COVID 29:33 Will Home Prices Drop 30:56 Appraisals vs Purchase Prices 31:41 Hot Price Points and Competition 32:44 Creative Loan Programs Today 36:00 Winter Outlook and Deal Hunting 39:09 Motivated Buyers and Reeducation 40:56 Credits vs Price Cuts 43:32 What Makes a Great Agent 49:18 Closing Questions and Wrap Up

  6. Sep 29

    What a Great Real Estate Agent Really Does with Brooke Buckett - The Long Game - Ep. #104

    Most buyers focus on finding the right house. The best agents help you find the right life. In this episode of The Long Game Podcast, Ryan sits down with Brooke Buckett, a Rhode Island-based real estate agent specializing in relocation and community matchmaking, to talk about what a truly great agent actually does, and why the difference between a good transaction and a great one often comes down to the conversations most agents never have. Ryan and Brooke also dig into the lending side of the equation, specifically how buyer strategy and financing strategy have to work in tandem right now. Getting a payment to a comfortable number in an elevated rate environment isn't one thing. It's a combination of rate options, seller credits, buydown strategies, and program selection that most buyers never even know are on the table, because most lenders take the path of least resistance and never show them. What You'll Learn: Why Brooke's first consultation has almost nothing to do with houses and everything to do with how you actually want to liveWhat the Rhode Island market looks like heading into fall 2026 for both buyers and sellers, and where the real opportunities areWhy sellers are still anchored to 2021 pricing expectations and how a data-driven agent navigates that conversation honestlyThe pricing strategy Brooke uses to generate maximum demand for a listing, and why listing under market value often nets sellers moreWhat buyers routinely overlook when walking a property, and why going to showings unaccompanied is one of the most costly mistakes a first-time buyer can makeHow Ryan and Brooke collaborate on deal strategy in real time, and what that looks like when a client needs a rate buydown, a seller credit, and a renovation loan all at onceWhy a preapproval letter with no payment discussion, no program explanation, and no options presented is a red flag, not a green light If you're buying or selling in Rhode Island or nearby Massachusetts and want to understand what a high-level agent and lender partnership actually looks like in practice, this episode gives you a clear and honest picture of what you should expect and what to ask for. Interested in connecting? GUESTS Brooke Buckett REALTOR, RE/MAX River's Edge | Educator, How To Buy A Home Class brookebuckettrealestate@gmail.com | brookebuckettrealestate.com  Instagram: @brookebuckettre HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Why Great Agents Matter 01:28 Rhode Island Market Update 03:24 Negotiation Strategy and Credits 06:22 Start Buying With Education 09:56 Seller Expectations and Pricing 16:19 Hyper Local Neighborhood Know How 18:00 Matchmaking Buyers to Communities 21:20 Buyer Consultation Must Haves 24:54 Cosmetic vs Functional Priorities 25:42 Investor vs Homeowner Mindset 27:43 New Construction Trends 30:01 Creative Space Solutions 32:42 Why Buyers Need Representation 34:00 Strategies for High Rates 38:12 Better Preapproval Conversations 41:08 Seasonal Deals and Wrap Up

  7. Sep 22

    Viral vs. Valuable Content with Russ Mangsen & Alex Fischer - The Long Game - Ep. #103

    Going viral sounds great. For most local businesses, it's the wrong goal entirely. In this episode of The Long Game Podcast, Ryan sits down with Russ Mangsen, social media strategist and host of Networking Over Nine, and Alex Fischer, Team Richards' marketing manager, for a round-table conversation on what's actually working in content and marketing right now, and what most business owners are getting completely wrong. The conversation kicks off with Judy's Pancakes and how she's a case study in why follower count and business success are not the same metric. They also get into the state of SEO, why every caption, blog post, podcast description, and social video is now part of your discoverability footprint, and why the businesses showing up first in AI-powered search results are the ones that have been putting out consistent, keyword-rich content for years.  What You'll Learn: Why follower count is one of the least useful metrics for a local service-based business, and what to track insteadHow to think about the viral content question honestly: when it helps, when it doesn't, and how to know which situation you're inWhy having multiple brand pages for different arms of your business creates more leverage than trying to be everything on one pageThe difference between Facebook and Google ads, and why running ads before building an organic presence is a common and costly mistakeWhy Russ replaced the term SEO with "searchability," and what that shift means for how you should think about everything you put outHow AI-powered search is changing discoverability, and why the businesses already putting out consistent content are positioned to winWhy shares and saves are the metrics that actually matter on Instagram right now, and why likes have become almost irrelevantWhy your social media presence and your in-person presence need to match, and what happens when they don't If you're putting out content consistently but not seeing it translate into real business, or if you've been wondering whether to run ads or chase viral moments, this episode gives you a clear and honest framework for making those decisions with the right goals in mind. Interested in connecting? GUESTS Russ Mangsen Owner, Marketing With Russ, Inc | Host, Networking Over Nine russ@marketingwithruss.com | marketingwithruss.com  Instagram: @marketingwithruss @networkingover9 Alex Fischer Marketing & Growth Manager, Team Richards | Podcast Producer & Content Creator alex@richardsrealtygroup.net | afischer.info  Instagram: @aj_fischer @alfish____ HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Welcome and Guests 00:52 Viral Versus Brand 06:26 Authenticity and Monetization 09:30 Multiple Pages Strategy 14:03 Ads That Actually Work 16:35 LLMs and AI Search 20:36 Hashtags and Algorithm 24:16 Modern SEO Searchability 29:00 Online Reputation and Authenticity 32:20 Recap and Wrap Up

  8. Sep 15

    Buying A House In Today’s Market - The Long Game Podcast - Ep. #102

    Most people think the homebuying process starts with finding a house. It doesn't. In this episode of The Long Game Podcast, Ryan shares exactly what he'd do if he were buying a house in 2026, drawing on his experience as a mortgage lender and purchasing six properties of his own in the last three years. Most prospective buyers walk into the process with false assumptions about what they can afford, how much cash they actually have available, and what they truly need in a property versus what they've just convinced themselves they need. Getting honest about all three before anything else happens is what separates a smooth homebuying process from a stressful one. What You'll Learn: Why a financial audit is the right first step before talking to anyone else in the homebuying processHow to identify a comfortable monthly mortgage payment before a lender tells you what you qualify for, and why that number matters moreWhy qualifying income and livable income are not the same thing, and how that gap catches buyers off guardWhat a real mortgage consultation looks like compared to an online application, and what questions should actually be asked firstHow to find the right real estate agent for your property type, market, and stage of the homebuying journeyHow to separate must-haves from nice-to-haves so you don't box yourself out of properties that would actually workWhy leaving a consultation with a specific action plan and a deadline is the difference between a goal and a timeline If you're thinking about buying a home in the next six to twelve months and don't know where to start, this episode gives you a clear, honest, and practical roadmap for getting ready before you ever make an offer. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in CT, FL, MA, ME, NH, RI, NC, PA, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Buying in 2026 Overview 00:33 Feasibility Study Basics 01:21 Run a Financial Audit 01:56 Test Your Payment Comfort 02:38 Cash Reserves and Repairs 03:26 Mortgage Advisor Consultation 05:01 Programs and Price Point 05:31 Choose the Right Agent 06:46 Must Haves vs Nice 07:37 Compromises and Commutes 08:24 Build a Timeline Plan 09:04 Wrap Up and Next Steps

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Ratings & Reviews

5
out of 5
4 Ratings

About

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-caliber conversations — the mental models, systems, mistakes, and tradeoffs that shape durable success over time. Through solo reflections and deep conversations, The Long Game gives listeners proximity to real operators and the clarity that comes from understanding how the best actually think, judge risk, and execute. If you’re an ambitious builder who wants to learn from real experiences — not shortcuts or hype — this is an invitation inside. Welcome to The Long Game.

Information

  • Creator
    Ryan Richards
  • Years Active
    2022 - 2026
  • Episodes
    109
  • Rating
    Explicit
  • Copyright
    © 2026 The Long Game by Ryan Richards
  • Show Website
    The Long Game by Ryan Richards