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

    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

  2. Aug 11

    My first rental was a disaster... but worth it | The Long Game Podcast

    Burning down your shed can be a strong deterrent for first time rental owners… here’s what you can learn from it. In this episode of The Long Game Podcast, Ryan shares what his first rental property actually taught him, starting with a five-unit multifamily that threw everything at him at once: evictions, bedbugs, electrical problems, non-payment of gas accounts, troubled tenants, and one tenant who burned down his shed. None of it was in the plan. All of it was education. Ryan uses that experience as a jumping-off point for a broader framework on real estate investing: before you choose a strategy, you need to know why you're investing in the first place. The vehicle only works if it matches the goal. Someone chasing generational wealth and someone chasing quick cash are not looking for the same investment, and treating them like they are is one of the most common and costly mistakes new investors make. He walks through the three main investing paths, flipping, multifamily, and short-term rentals like Airbnb, and maps each one to the type of investor it actually suits: the time you have, the capital you can deploy, the hands-on involvement you're willing to take on, and the long-term outcome you're building toward. The framework is simple, but most people skip it entirely. What You'll Learn: Why your first investment property is almost always a crash course, and why that's exactly the pointHow to identify your core investing objective before you choose a strategy, and why getting that backwards is so costlyThe key differences between flipping, multifamily investing, and short-term rentals, and which type of investor each one actually suitsWhy multifamily is one of the most effective long-term wealth-building vehicles for investors who don't have unlimited timeHow to factor property management into your underwriting from the start so it doesn't catch you off guard laterWhy Airbnb is a business first and a real estate investment second, and what that distinction means before you commitHow aligning your strategy with your availability, capital, and goals puts your effort in the highest-value places from day one If you're thinking about getting into real estate investing but aren't sure which path makes sense for you, this episode gives you an honest and practical framework for making that decision before you spend a dollar. 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 Starting With Purpose 00:33 First Deal Crash Course 01:24 The Long Game Mindset 01:44 Pick Your Strategy 02:32 Time Versus Effort 03:23 Multifamily With Help 03:54 Airbnb Is A Business 04:14 Define Your Objective 04:35 Final Takeaways

  3. Aug 4

    What Building a $200M/year Team Can Teach You with Ben Carbone - The Long Game - Ep. #96

    You don't truly understand your business until you start building a team around it. In this episode of The Long Game Podcast, Ryan sits down with his business partner Ben Carbone, team lead of We Close Deals, co-owner of We Stage Homes, and owner of Woodstock Estates, for a wide-ranging conversation on what it actually looks like to run multiple businesses at once, make smart hiring decisions, and lead a team that believes in the mission. Ben shares where things stand across his portfolio: We Close Deals is on pace to do over $200 million in transactions in its first full year as a team, We Stage Homes has completed over 65 stages in seven months after starting on a whim with a Google Doc, and a 130-unit acquisition in Maine is weeks away from closing. They also dive into an Ascend Summit postmortem, providing takeaways from each of the speakers and panelists that helped make the event the success that it was. What You'll Learn: How We Close Deals grew from a collective 50 million to 200 million in gross sales in just 12 months, and what actually drove that growthWhy the moment you start building a team is the moment you finally understand how your business really worksHow to decide which tasks belong to you and which ones to offload, especially when you're running multiple businesses at onceWhy managing your own properties might be costing you more than you realize, and how opportunity cost should drive that decisionWhat urgency actually looks like in practice, and why the wealthiest operators respond the fastestThe Ascend Summit postmortem: key lessons from the speakersWhy culture isn't built in team meetings. It's built in the small moments, the birthday cakes, the names you remember, the wins you celebrate together If you're managing multiple businesses or building a team and trying to figure out how to do more without losing the things that made you successful in the first place, this episode is an honest and energizing look at what that process actually requires. Interested in connecting? GUEST Ben Carbone Team Lead, We Close Deals | Co-Owner, We Stage Homes | Owner, Woodstock Estates bcarbone@lamacchiarealty.com | https://www.weclosedealsteam.com  Instagram: @ben.carbone | @weclosedealsteam  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 Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Episode Setup 01:34 Ben Returns 01:58 Scaling Lessons 04:02 We Close Deals Growth 06:49 Leadership Mirror 11:16 Launching Staging Company 14:14 Delegation Decisions 17:39 Urgency and Focus 22:08 Downtime CEO Mindset 24:45 Working On Business 25:24 Mortgage Push Pull 26:41 Hiring Key Players 27:12 Seamless Partner Communication 28:13 Blueprinting Closings Together 28:41 From Vendors to Partners 29:14 Hiring for Growth 29:36 Stop Self Managing Rentals 31:14 Buying Back Your Time 33:09 Scaling With Property Managers 34:19 Ascend Summit Recap 35:33 Anthony Lamacchia Lessons 39:46 Culture and Leadership Standards 40:57 CJ Sincotta Focus and Scale 46:22 Principles and Closing Thoughts

  4. Jul 28

    Stop Defending the Plan, Start Improving It - The Long Game - Ep. #95

    The plan you start with is rarely the plan that works. That's not failure, that's how it's supposed to go. In this episode of The Long Game Podcast, Ryan shares what he's learned in the 60 to 90 days since bringing on his two most recent hires, and why roughly half of the systems, SOPs, and plans he built before they arrived have already been shelved, adjusted, or rebuilt from scratch. He draws on a principle from The Algorithm by John McNeill, which examines Elon Musk's operating philosophy, to make the point that questioning the status quo isn't a sign of dysfunction. It's the engine of a well-run operation. The people actually doing the work are the ones who see the inefficiencies most clearly, and if you've built a culture where they feel free to say so, you've given yourself a significant advantage. Ryan also addresses the flip side: iteration without a foundation is chaos. Before you can optimize, you need a rhythm. Something as simple as a shared Google Sheet and a daily end-of-day recap creates the cadence your team needs to spot what's working and what isn't. Get the system down first, then find the right software to replace it. What You'll Learn: Why 50 to 60% of Ryan's original onboarding plan has already been changed or cut, and why that's a sign the process is workingHow to set the right expectation with new hires from day one when you're building roles that have never existed beforeWhy questioning everything, including your own systems, is a leadership principle worth instilling across your whole teamWhat it looks like to do a 60 to 90-day reset: pruning what isn't working and doubling down on what isWhy your employees often have better visibility into operational inefficiencies than you do, and how to unlock that perspectiveWhy you should establish a simple foundational rhythm before you ever evaluate software or automationHow to sequence the process correctly: get the work done first, identify the gaps, then find the tools that solve for them If you're building a team and feeling the tension between having a plan and staying flexible enough to actually execute, this episode gives you a practical and honest look at how to hold both at the same time. 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, SC, PA, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Plans Will Change 00:51 Hiring And Onboarding Lessons 01:46 Build The Plane Midair 02:28 Question Everything Culture 03:36 Empower Employee Initiative 04:24 Reset And Prune The Plan 05:17 Keep A Stable Backbone 06:08 Start Simple Before Software 07:18 Wrap Up And Next Updates

  5. Jul 21

    8 Networking Tips for Introverts & Extroverts - The Long Game - Ep. #94

    Most people leave networking events with a stack of business cards and nothing to show for it. Here's why. In this episode of The Long Game Podcast, Ryan breaks down how he built his network intentionally across Worcester, Providence, and eventually Boston, and shares the specific strategies he wishes he had known when he was filling his calendar with five events a week and talking to everyone without a plan. He also reframes the follow-up entirely. The goal isn't to book ten coffee meetings. It's to show up with something of value, a warm introduction, a relevant connection, a reason for someone to remember that you thought of them. That single shift, leading with generosity instead of a calendar invite, is what turns a business card into an actual relationship. What You'll Learn: How to choose which markets and which events are worth your time, and which ones to cutWhy finding the host first at any event is one of the highest-leverage moves you can make in the roomHow to become the person who connects people, and why that role compounds faster than any pitch ever willWhy it's not only acceptable to exit a conversation that's going nowhere, it's the right callHow to audit whether you're actually networking or just socializing with a drink in your handWhy a drawer full of business cards is a symptom of a follow-up problem, not a networking problemHow to lead with value in your follow-up so you're memorable before you ever ask for anything If you're putting time into networking but not seeing it translate into real business relationships, this episode gives you a practical and honest look at where the process is probably breaking down. 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, SC, PA, TN, VT Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Why Networking Matters 00:55 Pick Your Market 01:55 Quality Over Quantity 02:41 Work The Host 03:27 Become The Connector 03:59 Exit Dead End Chats 05:24 Follow Up With Value 06:03 Skip The Coffee Trap 07:00 Stay In Touch Systems 07:30 Final Networking Mindset

  6. Jul 14

    Branding Isn’t Just Logos - The Long Game - Ep. #93

    When you think of branding, you’re probably thinking of a logo. But those who build something lasting start with the impact and work backwards from there. In this episode of The Long Game Podcast, Ryan breaks down what he wishes he had known about branding when he started, why the logo-and-colors phase is just the surface, and how to build a brand that speaks to the company you're becoming, not just the one you are today. Ryan makes the case that branding is not a design exercise, but a strategic one. Your colors, your content, your voice, and who you choose to collaborate with are all communicating something to the market, whether you're intentional about it or not. He walks through how his own approach evolved, from early content that was purely mortgage-focused to a deliberate effort to show up as an investor, community builder, and podcast host as well, because if you don't talk about it, people simply won't know. He also gets into the audit process his team runs regularly to make sure what they're putting out still reflects where they're trying to go. What You'll Learn: Why starting with a logo and color palette is the right first step but the wrong stopping pointHow to work backwards from the company you want to be rather than just documenting the one you are todayWhy "manifest into the company you want to become" is a more useful frame than "fake it till you make it"What a social media audit actually looks like in practice, and why Ryan's team runs them regularlyHow staying too narrow in your content can quietly limit how the market sees you and what opportunities find youWhy cross-collaboration is a branding decision as much as a marketing one, and how to choose partners intentionallyHow the content you put out today is either building toward your future brand or drifting away from it If you're building a business and putting out content without a clear picture of where it's all supposed to land, this episode gives you a practical framework for getting intentional about your brand before the market decides what it means for you. 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, SC, PA, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Branding Beyond Logos 01:25 Define Your Value Proposition 02:01 Brand for Your Future Self 02:43 Audit Your Content Strategy 03:02 Expand What You’re Known For 04:17 Confidence Shapes Perception 05:00 Collaborate With Intention 06:23 Final Takeaways

  7. Jul 7

    The Ascend Summit: A Story of Consistency & Perseverance - The Long Game - Ep. #92

    Most people don't fail because the idea was bad. They fail because they quit before it had time to work. In this episode of The Long Game Podcast, Ryan shares the origin story of the Ascend Summit and the lessons from this year's event that hit closest to home: what perseverance actually looks like in practice, why consistency is the variable most people underestimate, and why the best time to hire is always earlier than feels comfortable. Ryan walks through how the Ascend Summit started three years ago with a trip to the Clever Summit in Florida, a Google Doc, and a conversation with his business partner Ben Carbone about why there was nothing like that in New England. What followed was a mastermind with 12 students, then a first summit of around 100 people, then a gradual expansion in scope, content, and vision that culminated in the 2026 Ascend Summit: 150 attendees, five panelists, a keynote speaker running a billion-dollar company, and a production team of 15. None of it happened at once. All of it happened because they stayed the course. What You'll Learn: How the Ascend Summit went from an idea and a Google Doc to a 150-person event with a billion-dollar keynote speakerWhy most businesses fail not because of a bad idea or weak work ethic, but because they stop too soonWhat Angelo Purina's story of working 72-hour stretches in a commercial kitchen teaches about what commitment to a vision actually looks likeWhy the best time to hire is 12 months before you think you need to, and what it costs to wait until it feels obviousHow shiny object syndrome and the impulse to quit are often the same problem wearing different masksWhy staying the course on one thing, even slowly, compounds in ways that starting five new things never willWhat it looks like to build something from nothing in public, including the social media cadence, the community, and the events that make it real If you're sitting on an idea you keep starting and stopping, or a business that's growing but not fast enough, this episode is a direct and honest case for what it actually takes to see something through. 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, SC, PA, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Big Ideas Intro 00:07 Conference Spark 01:01 Launching Informed Investor 01:23 Ascend Summit 2026 Highlights 02:10 Perseverance Pays Off 03:35 From Google Doc to Mastermind 04:06 First Summit and Bigger Vision 04:38 Building Community and Content 05:34 Loving the Grind 06:05 Angelo’s 72 Hour Hustle 06:55 Hire Before You Need To 07:59 Looking Ahead and Wrap Up

  8. Jun 30

    Shiny Object Syndrome - The Long Game - Ep. #91

    The most expensive decisions aren't the ones you got wrong. They're the ones you made too fast. In this episode of The Long Game Podcast, Ryan breaks down how he thinks about decision-making as a leader, why the speed of a decision matters as much as the decision itself, and what he's been actively teaching his team as his business grows. Ryan walks through the two failure modes he sees most often: moving too quickly on tasks that deserve a pause, and letting attention scatter across too many priorities at once. He's direct about the fact that neither comes from bad intentions. The person who rushes through a document review isn't cutting corners on purpose. But slow is fast, and the cost of catching a problem at the wrong stage is almost always higher than the cost of taking an extra ten minutes upfront. He also gets into the decisions people don't realize they're making, specifically where they place their attention. Shiny object syndrome isn't just a distraction. It's a choice, and most of the time it's a subconscious one. What You'll Learn: Why making a decision quickly and making it well are not the same thing, and how to know which one a situation calls forThe specific moment in a workflow where slowing down saves more time than any shortcut ever couldWhy "slow is fast" is one of the most practical frameworks for a growing team to internalizeHow shiny object syndrome operates as a subconscious decision, and what it quietly costs your businessWhy Ryan pulled back from real estate investing for the better part of a year, and what that focus producedHow to identify the highest ROI use of your attention when multiple opportunities are competing for itWhat it looks like to correct your direction intentionally rather than drift toward wherever your habits point If you're running a growing business and finding that things are falling through the cracks despite everyone working hard, this episode gives you a clear framework for why that happens 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, SC, PA, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Decisions Fast or Slow 00:51 Too Much on Your Plate 01:46 Slow Is Fast Example 03:45 Low Stakes Quick Calls 04:13 Attention and Focus Choice 04:48 Doubling Down to Grow 05:44 ROI and Recalibration 06:37 Final Takeaways

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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
    98
  • Rating
    Clean
  • Copyright
    © 2026 The Long Game by Ryan Richards
  • Show Website
    The Long Game by Ryan Richards