The Long Game by Ryan Richards

Ryan Richards
  • 5.0 (4)
  • Entrepreneurship
  • Updated 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

    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

  2. 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

  3. 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

  4. 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

  5. Sep 8

    Creating Feedback Loops - The Long Game Podcast - Ep. #101

    What if the fastest way to improve your business was already sitting on your team? In this episode of The Long Game Podcast, Ryan shares the system he's been building over the past six months to make feedback a daily habit rather than a quarterly event, and why that shift has moved his team further on the systems side in half a year than he expected. He also walks through two practical tools his team has been using: a living document where team members can submit suggestions for process improvements, and a workload audit that maps out how each person is spending their time across the week. The second one led directly to a new hire on the editing side so his marketing manager Alex could focus on higher-leverage work. Neither tool works without follow-through, and Ryan is direct about that. An idea that lives in a Google Doc with no owner, no deadline, and no next step is an idea that dies. What You'll Learn: Why saving feedback for a review meeting is one of the most common leadership habits worth breaking, and what to do insteadHow a continuous feedback loop pulls employees into your thought process over time, not just your preferred outcome on a single taskWhy asking questions is more effective than issuing corrections, and what that sounds like in practiceHow to create a living document for team suggestions that actually produces action rather than a graveyard of good ideasWhy every suggestion needs an owner, a deadline, and a defined next step before it has any chance of becoming a real improvementHow a workload audit works and what Ryan found when he mapped out how each team member was spending their weekWhy a culture that encourages everyone to contribute and improve is also one of the strongest selling points for future hires If you're leading a team and feel like the same inefficiencies keep showing up no matter how many times you address them, this episode gives you a practical and honest look at why that happens and how to build a system that actually fixes it. 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 Why Feedback Loops Matter 01:02 Instant Feedback Habit 01:42 Teach the Thought Process 02:15 Avoid Review Meeting Dumps 02:46 Team Suggestions Document 03:30 Turn Ideas Into Action 03:58 Build an Improvement Culture 04:56 Efficiency Audit Example 05:48 Weekly Optimization Meetings 06:18 Wrap Up and Next Steps

  6. Sep 1

    Content vs Branding - The Long Game Podcast - Ep. #100

    Can someone land on your page and know what you do in 30 seconds? In this episode of The Long Game Podcast, Ryan marks episode 100 with something more useful than a celebration: an honest look at where his marketing and branding actually stand. Ryan draws a clear line between content creation and branding, and makes the case that most businesses, including his own, conflate the two. Posting consistently is the foundation, and getting there is a real accomplishment. But once that rhythm is in place, the next question matters just as much: can someone land on your page and know within 30 seconds what you do, why they should call you, and how to reach you? If the answer is no, the content is working harder than the brand. He walks through the specific things his team is auditing and adjusting: thumbnail messaging, visual consistency, call-to-action clarity, and the number of clicks it takes for someone to book a meeting.  What You'll Learn: Why content creation and branding are not the same thing, and what the gap between them is costing your businessHow to audit your own page the way a stranger would: 30 seconds, cold, no contextWhy too many calls to action is the same problem as no call to action at all, and how to fix itWhat Tesla's approach to simplifying consumer choice teaches about reducing friction on your business pageWhy the quality and consistency of your content should reflect the level of advisor you're positioning yourself to beHow to think about the cadence for revisiting and realigning your branding as your business evolvesWhat Ryan and his team are changing heading into the next phase of The Long Game Podcast and Team Richards If you're putting out content consistently but not seeing it translate into real inquiries or bookings, this episode gives you a clear and honest framework for figuring out why, and what to do about it. 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 Episode 100 Reflection 01:12 Content vs Branding 02:17 Audit Your Messaging 03:12 Visuals and Clear CTAs 04:09 Tesla Lesson Simplicity 05:21 Match Quality to Brand 06:41 Relaunch and Next Phase

  7. Aug 25

    Reflections, Rebrands, and Racing to Ep. 100 - The Long Game Podcast - Ep. #99

    99 episodes in… here's what three years of The Long Game looks like. In this episode of The Long Game Podcast, Ryan reflects on nearly three years of building the show from the ground up. From a real estate and finance platform to something he didn't fully anticipate when he started: a living record of his own professional development. Ryan shares how the podcast has evolved alongside him, from solo loan officer to a team of five, from The Real Estate Lens to The Long Game, and from sharing information to pulling back the curtain on how entrepreneurs at every level actually think, build, and solve problems. What started as a place to talk about mortgages and investing has become something bigger: a space for curiosity, honest conversation, and the kind of insight that only comes from putting real operators in a room and asking them how they do it. Before episode 100, this episode looks back at some of the most memorable moments from the past three years, drawing on conversations with entrepreneurs, investors, sales professionals, marketers, and business builders who have each left something worth revisiting. What You'll Learn: How The Long Game Podcast started, what it was built for, and how it's evolved into something Ryan didn't fully anticipateWhy Ryan sees the show as a living record of his own growth, not just a content platformWhat the rebrand from The Real Estate Lens to The Long Game represented and why the shift matteredHighlights and standout moments from three years of guest conversations and solo episodesWhere Ryan sees the show going in the next three years, and what's already in the works heading into episode 100 If you've been along for any part of this journey, this episode is a chance to look back at how far the show has come. And if you're new, it's the perfect starting point before the milestone ahead. 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 Podcast Origins 01:41 Midterm Rental Edge 02:26 Scaling Short Term Rentals 03:17 Hospitality Systems 05:34 One Percent Rule 07:48 Crash Talk Explained 12:01 Zero to 100K Phase 14:47 Learning by Doing 15:45 Who Not How Mindset 17:59 Delegation Timing 19:02 Servant Leadership 19:47 Culture Feedback Loop 22:10 Core Tasks vs Delegate 25:02 Urgency Wins 26:47 Faster Than Five Year Plans

  8. Aug 18

    AI Tools That Actually Work with David Hill - The Long Game - Ep. #98

    AI won't replace the human touch. But it will replace the humans who ignore it. In this episode of The Long Game Podcast, Ryan sits down with David Hill, serial entrepreneur, sales trainer, marketer, and real estate agent, to talk about what it actually looks like to integrate AI into your business today, before most people have figured out how serious this moment really is. David brings two days of insights from a private event with John Lee, breaking down the WAVIT framework: five categories of AI use, written, audio, video, imagery, and tech, each with its own specialist tools and applications. He and Ryan dig into where most entrepreneurs go wrong with AI, chasing the perfect tech stack instead of starting with the problem they actually need to solve. They also get into data security, the risks of giving AI tools access to your computer without a sandbox in place, and why platforms like YouTube are becoming more valuable by the day as AI search pulls from everywhere to surface the most consistent, credible voices. What You'll Learn: The WAVIT framework: five categories of AI use and the best tools for each oneWhy starting with the problem you solve, not the tool, is the right entry point for AI adoptionHow to think about data security when AI tools have access to your files and systems, and what a sandbox actually isWhy YouTube is one of the most valuable platforms right now as AI search pulls from everywhere to find consistent, credible voicesWhat DISC is, how the four behavioral quadrants work, and why 70% of the population are S'sHow to identify someone's behavioral style within 30 seconds of a call and adapt your entire approach accordinglyWhy the best follow-up process is multi-channel, consistent, and intentional, and what 7 to 17 attempts actually looks like in practiceHow to use AI for sales training, including role play, transcript review, and real-time coaching feedback for your team If you're curious about AI but overwhelmed by the options, or you're in sales and wondering why your close rate isn't where it should be, this episode gives you two frameworks that work together and a clear place to start. Interested in connecting? GUEST David Hill Host, The Persistent Entrepreneur Podcast | Founder, Path to Mastery LLC | Founder, Ring Leader CRM hillteam@gmail.com | davidihill.com  Instagram: @davidihill  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 Episode Setup 01:25 Meet David Hill 01:56 Marketing as Media 02:34 AI Avatars and Fakes 04:17 WAVIT and Tool Stack 07:23 Content and Customer Clarity 09:21 Lead Qualification Filters 11:41 Follow Up Builds Trust 15:00 CRM DISC and AI Trio 16:05 DISC Quadrants Explained 18:43 Adapting Sales Style 25:09 Using DISC and AI Together 26:21 Spotting DISC on Calls 29:29 AI For Buyer Psychology 29:50 Hooks And Social Messaging 31:00 Consistency Builds Trust 32:17 AI Search And SEO 34:24 Prompting For Better Answers 35:42 Plumber Pricing With GPT 37:00 WAVIT Content Framework 40:00 AI Specialists For Sales 41:46 Avatar Sales Coach Demo 46:26 Automation Tools And Manus 48:18 Security And Sandboxing 51:56 Invest In Coaching

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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
    105
  • Rating
    Explicit
  • Copyright
    © 2026 The Long Game by Ryan Richards
  • Show Website
    The Long Game by Ryan Richards