The Long Game by Ryan Richards

Ryan Richards

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. 3d ago

    From Ideas to Action with Carolyn Hearn - The Long Game - Ep. #87

    Most people don't have a knowledge problem. They have an action problem. In this episode of The Long Game Podcast, Ryan sits down with Carolyn Hearn, a Dispositions Manager at Moss Home Solutions, a real estate wholesaling company based in Rhode Island, to talk about what it actually looks like to move from idea to action at 23 years old. Carolyn has been with Moss Home Solutions since she was 19, studying real estate at Penn State while building real-world experience every summer. Now full-time in dispositions and on her second house flip, she moves before she has every answer and figures it out on the way. Ryan and Carolyn also dig into analysis paralysis, the case for building a team before you feel ready, and what the nature versus nurture question actually looks like for two entrepreneurs who both learned the game from their dads. What You'll Learn: Why taking imperfect action beats waiting for the perfect plan, and what it actually costs to learn on a live dealHow to use proximity to people who are further along as a shortcut that no book can replicateWhy the advice "swim with the river" beats pushing yourself into a mold that doesn't fitWhat it really looks like to build a team from scratch, including how Ryan onboarded his marketing manager with a whiteboard instead of an SOPThe difference between doing everything yourself to build competence and doing everything yourself out of habitWhy gratitude and endurance work together as a mental framework for entrepreneurs at every levelHow to know if your goal is big enough: if it doesn't make you smile when you say it out loud, set a bigger one If you're early in your entrepreneurial journey and still waiting until you know enough to start, this episode will show you what it looks like to build confidence through action instead. Interested in connecting? GUEST Carolyn Hearn Dispositions Manager, Moss Home Solutions  carolyn@mosshomesolutions.com | https://mosshomesolutions.com Instagram: @carolyn.real.estate  YouTube: @carolynhearn6239 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 Intro 02:04 Her Real Estate Path 03:55 Wholesaling Explained 05:22 Power of Proximity 07:39 Who Not How Mindset 09:48 Building a Team Fast 15:27 Flip One vs Flip Two 19:48 Lessons From Mistakes 22:45 Beating Analysis Paralysis 24:09 Mentors Dad vs Moss 27:50 Big Goals and Empire 29:49 Host Vision and Business 30:59 Why Businesses Win 33:41 Second Flip Solo 38:06 Protecting Personal Time 40:23 Atomic Habits Showing Up 42:11 Get in the Room 43:33 Starting a YouTube Channel 47:06 Advice Gratitude and Endure 51:59 Nature Versus Nurture 56:12 Final Wrap and Next Steps

    57 min
  2. May 26

    Anticipating Success with Early Hiring - The Long Game - Ep. #86

    Most entrepreneurs don't have a hiring problem. They have a timing problem. In this episode of The Long Game Podcast, Ryan Richards discusses hiring before you think you're ready. Drawing from his own experience building out his team, Ryan breaks down why waiting until you're overwhelmed is the exact moment hiring becomes hardest, and what it costs you when momentum stalls. Ryan walks through the two traps entrepreneurs fall into when they wait too long to delegate: either they stop promoting new business to protect their service levels, or they try to do both and watch quality slip. He unpacks the "snowball" problem, where hesitation hands your competitors the time they need to close the gap.  Find the right person, build the systems together, and stop letting the fear of imperfection slow down what is already working. What You'll Learn: Why hiring when you're already overwhelmed makes the process harder, not easierHow waiting too long forces a costly trade-off between promoting new business and serving existing clientsWhy momentum is more valuable than perfection when you're in a growth phaseHow delaying a hire gives competitors time to catch up on what makes your approach uniqueWhy you don't need a complete SOP or perfect systems before bringing someone onThe mental shift from "I can't afford to hire" to "I can't afford not to"How to frame a new role honestly with candidates when you're building the position from scratch If you're a business owner who keeps saying you need help but keeps putting off the hire, this episode will show you exactly what that delay is costing you, and what to do about it instead. 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 MA, CT, FL, NC, NH, PA, RI, ME, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Reflecting on Growth 01:02 The Hiring Lesson 01:45 Capacity Kills Promotion 02:16 Service vs Sales Tradeoff 03:35 Momentum and Competition 04:17 Fear and Worst Case 06:36 Building the Team Vision 07:00 Final Takeaway

    7 min
  3. May 19

    Inside the Mind of a CEO with Andrew Bosco - The Long Game - Ep. #85

    Most people think in tasks. CEOs think in systems. In this episode of The Long Game Podcast, I sit down with Andrew Bosco, CEO of Candor Realty Group and founder of Granite and Pine Properties, to break down what it actually means to run a business from a 10,000-foot view and why that perspective changes everything. Andrew's path to the CEO seat wasn't a straight line. He spent time as a teacher, a scientist at Moderna and Pfizer, a real estate agent, and an investor before stepping into the top seat at Candor; a company on a mission to help one million people reach financial independence through real estate. He shares how imposter syndrome followed him into the role, why he initially said no, and what ultimately made him put the gas on the fire and commit. What You'll Learn: Why shifting from a 100-foot to a 10,000-foot view changes how you lead and buildHow Andrew went from imposter syndrome to CEO and what changed between the first no and the final yesWhat a system actually is and how people, processes, and technology work togetherWhy focus is the ultimate superpower in an era of infinite distractionHow to implement automation and new software without overwhelming your teamWhy the worst thing you can do is nothing If you're an entrepreneur, business owner, or operator trying to think bigger, build smarter, and stop getting in your own way, this one's for you. Interested in connecting? GUEST Andrew Bosco CEO, Candor Investment Group | Founder, Granite & Pine Properties a.bosco.realestate@gmail.com | candorinvestmentgroup.com Instagram: @candorinvestmentgroup  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 Intro 02:13 Andrew’s Background 03:18 Why He Became CEO 04:53 CEO Mindset Shift 07:56 Saying Yes Faster 11:13 Focus and Consistency 15:13 Authenticity Over Polish 18:21 Systems and Processes 22:59 Empowering the Team 26:31 Automation and Tools 35:49 BRRRR Strategy Explained 37:10 Perfect Day Freedom Goal 41:22 Calendar Control Systems 47:20 Meeting Days and Prospecting 52:26 Delegation and Partnerships 56:02 Imperfect Action Mindset 01:01:09 Community Beats Fear 01:04:19 Final Take Action Push

    1h 5m
  4. May 12

    Turning Effort Into Results - The Long Game - Ep. #84

    Busy and productive are not the same thing. In this solo episode of The Long Game Podcast, Ryan breaks down one of the most common traps entrepreneurs fall into: confusing activity with output. The problem is rarely discipline. More often, it is the absence of a clear, intentional process tied directly to revenue. Ryan walks through how to identify the highest ROI task in your business, why most people unknowingly replace that task with lower-value work, and how to build a repeatable process around the inputs that actually drive results. Using real examples from real estate, loan origination, and sales, he lays out a simple working-backwards framework for getting out of the busy-but-stuck cycle and into consistent, focused execution. What You'll Learn: Why busy entrepreneurs still stall and what the real bottleneck usually isHow to define the highest ROI activity for your specific business modelThe difference between prospect-related work and actual prospectingHow to use a working-backwards framework to build your ideal sales processWhy the problem is almost always the process, not the personHow to stay intentional about the tasks that actually move the needle If you have been putting in the hours but not seeing the results, this episode will help you identify what is actually getting in the way and give you a practical framework for fixing 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 MA, CT, FL, NC, NH, PA, RI, ME, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:49 Find Your Highest ROI Task 01:52 Busy Work vs Real Prospecting 02:54 Why You Avoid The Hard Stuff 03:18 Work Backwards From Sales 04:19 Build The Ideal Sales Process 05:12 One Hour Done Right 06:45 Process Beats Discipline 07:31 Repeat Optimize And Follow Up 07:58 Final Focus On Revenue

    9 min
  5. May 5

    Empowering Teams and Flipping Houses with Viktor Ryan - The Long Game - Ep. #83

    Most people know the decision they should make. They just don't have the courage to act on it. In this episode of The Long Game Podcast, Ryan Richards sits down with Viktor Ryan, Team Lead of Ryan & Co Realty Group based in Worcester, Massachusetts, to break down what it really takes to evolve from a solo operator into a business owner. Viktor shares his journey from managing 300 employees at trampoline parks, to launching a franchise restaurant, to accidentally starting a marketing company, and more. Each transition came with lessons, setbacks, and a willingness to find the exit point before hitting the breaking point. What You'll Learn: Why most people already know the decision they need to make and what stops them from acting on it.How Viktor transitioned from restaurants and marketing into full-time real estate.What to look for in a brokerage or mentor when you're starting from zero.The systems and checklists Viktor uses to manage a team, multiple flips, and a marketing business simultaneously.Why building a team requires learning an entirely new skill set and how Viktor's management background gave him a head start.How to flip for the right buyer by matching your renovation to the market, not your personal taste.If you're an entrepreneur navigating multiple ventures, thinking about building a real estate team, or trying to make a big career decision you've been putting off, this episode is the honest, real-world perspective you've been looking for. Interested in connecting? GUEST Viktor Ryan Ryan & Co Realty Group | Neighborhood Realty Group viktorryanrealtor@gmail.com | viktorryan.theneighborhoodrg.com 65 Southbridge St, Auburn, MA 01501 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: 01:15 Meet Viktor Ryan 03:15 From Parks to Protein 05:11 Finding Real Estate Path 09:41 Client Experience Mindset 13:27 Building a Real Estate Team 18:18 Why Agents Fail 23:47 Leadership and Culture 30:28 Mentors and Investing Shift 31:56 Hard Money Flip Plan 32:22 First Off Market Deal 33:16 Permit Shutdown Lesson 36:18 First Flip Results 38:12 Market Fit Mistake 40:33 Hyper Analyze Markets 42:53 Avoid Overspending Finishes 45:29 Systems Structure Delegation 48:14 Checklists Follow Up 53:48 Advice New Agents 56:34 Mentors Work Ethic 58:16 Closing Thanks Next Flips

    59 min
  6. Apr 28

    Ep. #82 | Leadership Is Built, Not Born

    Leadership isn’t something you’re born with… it’s something you build. In this episode, I break down a shift in thinking that completely changed how I approach leadership in my business. Too many people believe you either “have it or you don’t” but the reality is leadership is a skill set you can develop with intention. We get into what it actually means to be a good leader, how to identify what motivates the people around you, and why adaptability is one of the most important traits you can have. Not everyone is driven by the same things, and if you’re leading a team, it’s your responsibility to understand that. I also talk about the importance of leading by example. Your actions set the standard whether you realize it or not. The effort you bring, the habits you build, and the expectations you create all shape your company culture. But the biggest piece is this… your mission. People don’t work hard for your income goals or your sales targets. They work hard for something they believe in. If your vision is strong enough and your purpose is clear, your team will rally behind it. What you’ll learn: • Why leadership is a learned skill, not something you’re born with • How to identify what actually motivates each person on your team • Why adaptability is critical when leading different personalities • The impact of leading by example on company culture • How to create a mission that people genuinely want to rally behind If you’re building a business, leading a team, or looking to grow into a leadership role, this episode will challenge how you think about what it actually takes to lead effectively. #TheLongGamePodcast #FinanceWithTeamRichards

    8 min
  7. Apr 21

    Ep. #81 | Time Is Not the Problem - Your Priorities Are

    In this solo episode of The Long Game Podcast, Ryan Richards breaks down one of the most common limiting beliefs entrepreneurs, business owners, and sales professionals tell themselves: “I just don’t have enough time.” Ryan challenges the idea that success is limited by the number of hours in a day and explains why the real issue is usually priorities, systems, and how effectively you use your time. From building better habits to creating leverage through delegation, this episode is all about shifting your mindset so time stops being your excuse and starts becoming your advantage. Using real examples from business, fitness, and daily life, Ryan shares how he personally approaches calendar management, non-negotiable commitments, and system building to create more freedom without working more hours. What you’ll learn: Why “I don’t have enough time” is often a limiting belief, not a factHow priorities—not time—determine what gets accomplishedThe difference between being busy and being truly effectiveWhy time blocking and calendar control are critical for growthHow to create leverage through systems, delegation, and hiringWhy honoring commitments to yourself matters just as much as business commitmentsIf you’ve ever felt stuck, overwhelmed, or like there simply aren’t enough hours in the day, this episode will help you rethink how you approach your goals and give you practical strategies to take back control of your time.  #TheLongGamePodcast #FinancewithTeamRichards

    13 min
  8. Apr 14

    Ep. #80 | Leadership, Relationships, and Scaling Through Uncertainty with Zack Levesque

    In this episode of The Long Game Podcast, we sit down with Zack Levesque, Regional Vice President at Northpoint Bank, to break down what it really takes to lead, scale, and adapt in a changing market. Zack shares his journey from top-producing salesperson to sales leader, including the pivotal moment that forced him to rethink his entire business model during a market shift. From laying off half his team to rebuilding through purchase business, this conversation is packed with real-world lessons on resilience, leadership, and taking control of what you can control.  We dive deep into the importance of relationships, not just building them, but maintaining the right ones, even when it means having difficult conversations. Zack also shares how true leaders create growth by investing in their people, leading from the front, and focusing on long-term impact over short-term gain. What you’ll learn: Why market shifts expose weaknesses in your business modelThe moment that forced a complete pivot from refinance to purchase businessWhat great leadership actually looks like in practiceHow to build strong, reciprocal relationships that drive growthWhy work ethic and consistency are still the ultimate differentiatorsWhen and how to scale your business with the right supportThe mindset shift required to move from producer to true business ownerIf you’re an entrepreneur, sales professional, or business owner trying to scale, hire, or navigate uncertainty, this episode gives you a real look at what it takes to grow through it instead of getting stuck.

    1h 2m

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.

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