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

    The Power of Proximity - The Long Game - Ep. #90

    The room you walk into might change everything. But only if you walk in. In this episode of The Long Game Podcast, Ryan shares why the power of proximity is one of the most underrated tools available to any entrepreneur, and why the biggest mistake people make with it is thinking too small about who belongs in the room. Ryan breaks down why cross-industry rooms often produce more meaningful shifts than industry-specific ones. When someone outside your world looks at how you operate and asks "why do you do it that way?", that question alone can unlock a perspective no conference in your own niche ever would.  He walks through how this philosophy shaped his own trajectory, from showing up alone in a suit to a Worcester networking event, to building some of his closest business partnerships and finding his path into real estate investing entirely through the connections made that evening. What You'll Learn: Why cross-industry rooms produce more meaningful perspective shifts than staying in your own nicheWhat the power of proximity actually looks like in practice, and why it's rarely the "golden key" moment people expectHow Ryan's entire path into real estate investing started from one networking event he almost skippedWhy the mindset of someone running an eight or nine-figure company looks fundamentally different, and what you can absorb just by being in the roomHow two people who met at a single event after hours went on to build multiple eight-figure companies togetherWhy showing up alone, not knowing anyone, is often where the most important connections beginWhat Ryan set out to create with the Ascend Summit, and why the philosophy behind it goes back to this exact idea If you're someone who keeps putting off the event, the meetup, or the room you know you should be in, this episode is a direct and honest case for why that next step might be the one that changes everything. 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 Why Create This Room 00:30 Power of Proximity 00:41 Cross Industry Perspectives 01:26 Connections Not Secrets 02:25 Why Ascend Summit Exists 02:38 Event Stories That Changed Everything 03:26 My Networking Event Turning Point 03:52 Showing Up Alone 04:11 Meet Five People Rule 04:48 Thinking Like Bigger Operators 05:26 Bigger Problems Bigger Decisions 06:02 Your Circle Shapes Trajectory 06:22 Final Takeaways

    7 min
  2. Jun 16

    Prioritizing People Over Profit with Jamie Sanborn - The Long Game - Ep. #89

    Most people see the glam, but few see the 15-hour days that built it. In this episode of The Long Game Podcast, Ryan sits down with Jamie Sanborn, owner of One Eleven RX, a med spa based in Auburn, MA, to talk about what it actually takes to build a thriving business in an industry that looks a lot easier than it is. Jamie started One Eleven RX out of pure necessity. A registered nurse for 15 years, she was climbing the corporate ladder, running operations for a wound care center, making six figures, and still felt like something was missing. She started with spray tans out of her house, bootstrapped her way into aesthetics, and built a team of 14 doing multiple seven figures annually. Her path wasn't linear, and she doesn't pretend it was.  They talk about why Jamie hires for bedside manner over skill, what it means to "eat last" as a leader, how she navigated finding a compliant medical director partnership in one of the most regulated states in the country, and why staying honest with your team is the foundation everything else is built on. What You'll Learn: Why the med spa industry is far more medically serious than its Instagram presence suggests, and what compliance really looks like for an RN-owned practice in MassachusettsHow Jamie went from spray tans out of her house to a team of 14 doing multiple seven figures, and what the bootstrapped middle looked likeWhy hiring for bedside manner and cultural fit beats hiring for technical skill every timeWhat "eating last" actually looks like in practice, and why it's the single best thing a leader can do to build team loyaltyHow to know when you're ready to open a second location, and why opening too early is one of the most common mistakes in growing businessesWhy building a business forces you to confront your own blind spots, whether you're ready to or notHow to think about the nature versus nurture question as an entrepreneur who learned the game from watching a parent do it first If you're building a business in a service industry and trying to figure out how to grow without losing the personal touch that got you there, this episode is a practical and honest look at what that actually requires. Interested in connecting? GUEST Jamie Sanborn Founder, One Eleven RX  jamie@oneelevenrx.com | https://www.oneelevenrx.com  Instagram: @jamie.injx | @oneelevenrx  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 01:03 Meet Jamie Sanborn 02:40 From Spray Tans to Botox 04:53 Making the Leap 08:38 Growth Goals and Scaling 10:37 Hiring and Culture Fit 15:33 Leading with Service 19:05 Expansion Timing and Marketing 20:24 Cash Flow and Inventory Lessons 26:39 Finding the Right MD Partner 27:33 Doctor Partnership Setup 28:55 Staying Compliant 31:12 Choosing Core Services 32:53 Building Specialist Team 33:40 From Operator to Leader 35:59 Entrepreneur Mindset Reality 38:12 Injection Risks Training 39:47 Botox vs Filler Explained 44:34 Mentorship Full Circle 45:56 Advice Nature Nurture Wrap

    47 min
  3. Jun 9

    Building The Plane In The Air - The Long Game - Ep. #88

    A month in, with two new hires thriving. The only regret: not doing it a year ago. In this episode of The Long Game Podcast, Ryan shares what he learned in the 30 days since bringing on two new hires, an operations coordinator and a marketing manager, and why the only regret he has is not doing it sooner. Ryan walks through the 40 to 50 hours of preparation work he put in before his new team members ever showed up: mapping his existing systems, building a central operating manual, and documenting how he makes decisions so that two people could walk in and hit the ground running. He's transparent about what worked, what didn't, and why most of the systems he built were meant to be reshaped on the fly. The real value wasn't in getting it perfect. It was in having a foundation. What You'll Learn: Why most entrepreneurs' hiring problem is actually a systems problem in disguiseHow to document your own processes before you can effectively hand them off to someone elseWhy imperfect action still requires a baseline level of organization to succeedWhat "intangibles" actually look like when you're hiring for a small, growing teamWhy technical skill and cultural fit are not the same thing, and which one matters moreHow to create enough autonomy that a new hire can contribute from day one without constant hand-holdingWhy Ryan went from a team of three to a team of five in two weeks, and what that decision taught him If you're running your own business and feeling the pull to hire but keep stalling, this episode gives you a practical, honest look at what it actually takes to bring someone on and make it work. 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 Hiring Hesitation 00:21 Two New Hires Update 00:55 Regret And Readiness 01:37 Scaling Fast To Five 02:01 Documenting Your Work 03:08 Build A Company OS 03:55 Plans Will Change 04:23 Hire For Intangibles 05:56 Know Your Strengths 06:22 Blueprint For Autonomy 06:53 One Month In Results 07:04 What's Next Growth Plan

    8 min
  4. Jun 2

    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
  5. 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
  6. 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
  7. 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
  8. 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

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.