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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.
| Episode | Date |
|---|---|
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From Ideas to Action with Carolyn Hearn - The Long Game - Ep. #87
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Jun 02, 2026 |
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Anticipating Success with Early Hiring - The Long Game - Ep. #86
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May 26, 2026 |
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Inside the Mind of a CEO with Andrew Bosco - The Long Game - Ep. #85
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May 19, 2026 |
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Turning Effort Into Results - The Long Game - Ep. #84
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May 12, 2026 |
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Empowering Teams and Flipping Houses with Viktor Ryan - The Long Game - Ep. #83
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May 05, 2026 |
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Ep. #82 | Leadership Is Built, Not Born
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Apr 28, 2026 |
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Ep. #81 | Time Is Not the Problem - Your Priorities Are
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Apr 21, 2026 |
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Ep. #80 | Leadership, Relationships, and Scaling Through Uncertainty with Zack Levesque
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Apr 14, 2026 |
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Ep. #79 | From Operator to Owner: How to Break Through Your Ceiling
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Apr 07, 2026 |
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Ep. #78 | Stop Chasing Leads and Fix Your Processes
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Mar 31, 2026 |
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Ep. #77 | From Solo Agent to Scalable Business: Lessons from Nate Rock
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Mar 24, 2026 |
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Ep. #76 | Artificial Intelligence in the Real Estate Industry - Current Status and Future Predictions
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Mar 17, 2026 |
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Ep. #75 | How Authentic Marketing Wins in the AI Era with Tara Ostromecky
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Mar 10, 2026 |
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Ep. #74 | Stop Overthinking: A Simple Framework for Better Business Decisions
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Mar 03, 2026 |
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Ep. #73 | From “Boots on the Ground” to Building a Scalable Operation with Grindstone Sealcoating
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Feb 24, 2026 |
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Ep. #72 | The Operator’s Journey: Understanding Business Seasons
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Feb 17, 2026 |
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Ep. #71 | Phases of Entrepreneurship: From Doing the Work to Building the Vision
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Feb 10, 2026 |
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Ep. #70 | Systems, Partnerships, and the Power Couple Playbook With Tony and Ashley Eisenhauer
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Feb 03, 2026 |
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Ep. #69 | Manifesting Your Legacy with Ben Carbone
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Jan 27, 2026 |
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Ep. #68 | Welcome to The Long Game
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Jan 23, 2026 |
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Ep. #67 | When Does It Make Sense to Sell a Rental Property?
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Dec 23, 2025 |
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Ep. #66 | Capital Expenditures: Planning for Unexpected (And Expected) Repairs
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Dec 17, 2025 |
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Ep. #65 | From Nurse to Real Estate Investor: How Abigail Bought Her First Multifamily at 24
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Dec 09, 2025 |
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Ep. #64 | How AI and Automation Are Reshaping Small Business Systems with Bryce Meizen
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Dec 02, 2025 |
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Ep. #63 | From Payroll Sales to Full-Time Real Estate Investor with Wendell Butler
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Nov 25, 2025 |
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Ep. #62 | Closing Costs 101: What You’ll Really Pay at the Closing Table
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Nov 18, 2025 |
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Ep. #61 | 2008 Again? Not in New England.
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Nov 11, 2025 |
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Ep. #60 | Why Mortgage Rates Went Up After the Fed Cut Interest Rates
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Nov 04, 2025 |
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Ep. #59 | The #1 Reason Buyers Get Denied for a Mortgage
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Oct 28, 2025 |
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Ep. #58 | How to Analyze a Real Estate Deal in 60 Seconds
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Oct 21, 2025 |
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Ep. #57 | Our First "Informed Investor" Mastermind Success Story
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Oct 14, 2025 |
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Ep. #56 | How to Start Investing in Real Estate (Step-by-Step)
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Oct 07, 2025 |
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Ep. #55 | Residential vs. Commercial Financing 101: Key Differences
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Sep 30, 2025 |
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Ep. #54 | Investing Out of State and Building a 50-Unit Portfolio with Jessie Dillon
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Sep 24, 2025 |
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Ep. #53 | Breaking Free from Analysis Paralysis in Home Buying
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Sep 16, 2025 |
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Ep. #52 | What Realtors Need to Know About Mortgages
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Sep 09, 2025 |
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Ep. #51 | 3 Mortgage Hacks Every Homeowner Should Know
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Sep 02, 2025 |
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Ep. #50 | Refinancing 101 | How to Know if It’s Worth It
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Aug 26, 2025 |
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Ep. #49 | Navigating Complex Deals and Market Shifts with Spenser Molloy, Next Home Realty
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Aug 19, 2025 |
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Ep. #48 | How Home Insurance Can Impact Your Real Estate Deal
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Aug 12, 2025 |
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Ep. #47 | Building Teams, Scaling Impact, and Navigating the 2025 Real Estate Market with Ben Carbone
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Aug 05, 2025 |
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Ep. #46 | Inside the Home Inspection Business with Mike Sweeney of House Doctor Home Inspections Inc.
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Jul 30, 2025 |
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Ep. #45 | How to Get Financing as an Entrepreneur or Independent Contractor
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Jul 22, 2025 |
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Ep. #44 | Lessons from My First Single-Family Flip: What I Got Right, What I’d Do Differently
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Jul 15, 2025 |
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Ep. #43 | Why Everyone’s Moving to Rhode Island, with Brooke Buckett
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Jul 08, 2025 |
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Ep. #42 | A Day in the Life of a Loan Officer: What It’s Really Like Behind the Scenes
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Jul 01, 2025 |
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Ep. #41 | Building a Brand That Actually Works with Russ Mangsen of Marketing with Russ Inc.
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Jun 24, 2025 |
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Ep. #40 | Creative Financing Strategies to Adjust Your Down Payments & Closing Costs and Maximize Return
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Jun 17, 2025 |
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Ep. #39 | What Happens After Your Offer Is Accepted? A Step-by-Step Guide to Closing
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Jun 10, 2025 |
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Ep. #38 | Top 5 Things to Ask Your Loan Officer Before Making a Move
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Jun 03, 2025 |
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Ep. #37 | The Power of Networking: How Relationships Fuel Success in Business and in Life
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May 27, 2025 |
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Ep. #36 | How to Run a High-Performing Airbnb and Midterm Rental Business
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May 21, 2025 |
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Ep. #35 | How Our Clients Are Winning in the 2025 New England Real Estate Market
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May 13, 2025 |
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Ep. #34 | Informed Investor Mastermind Conference: May 29th
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May 06, 2025 |
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Ep. #33 | Defining Your Buy Box: A Must for First-Time Buyers and Experienced Investors Alike
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Apr 29, 2025 |
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Ep. #32 | Mortgage Rates in April 2025: What You Need to Know
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Apr 22, 2025 |
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Ep. #31 | Financial Planning for Buyers: Smart Strategies for Real Estate Success with Matt Ward
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Apr 15, 2025 |
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Ep. #30 | Building a Scalable Real Estate Business with Brooke Coughlin
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Apr 08, 2025 |
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Ep. #29 | The 3 Biggest Lessons I've Learned in Real Estate
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Apr 01, 2025 |
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Ep. #28 | The 3 Biggest Mistakes Homebuyers Make and How to Avoid Them
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Mar 25, 2025 |
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Ep. #27 | My Experience Managing a Portfolio Remotely
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Mar 18, 2025 |
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Ep. #26 | Why I Started a Mastermind Group
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Mar 11, 2025 |
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Ep. #25 | Using Property Management Software to Become More Efficient & Save Time
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Mar 04, 2025 |
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Ep. #24 | Favorite Client Wins of 2024
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Feb 25, 2025 |
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Ep. #23 | Financing Options for Self-Employed Borrowers
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Feb 18, 2025 |
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Ep. #22 | How to Make Your Business More Efficient - Real Estate Edition
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Feb 11, 2025 |
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Ep. #21 | Spenser Molloy's Pivot from Managing Short-Term Rentals to Becoming a Full-Time Realtor
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Feb 04, 2025 |
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Ep. #20 | The State of the Real Estate Market | Brooke Buckett
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Jan 28, 2025 |
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Ep. #19 | Down Payment Assistance Options for First-Time Home Buyers
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Jan 21, 2025 |
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Ep. #18 | Strategies to Reduce Your Cost of Living When Purchasing a Property
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Jan 14, 2025 |
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Ep. #17 | Real Estate Wholesaling with Ben Simon: Sourcing Leads Tactfully and Key Tips for Success
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Jan 07, 2025 |
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Ep. #16 | Breaking Down Value-Add: How to Increase the Value of Your Investment Property featuring Ben Carbone - The Long Game by Ryan Richards
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Dec 24, 2024 |
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Ep. #15 | Understanding the Different Types of Financing: Pros, Cons, and When to Use Them - The Long Game by Ryan Richards
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Dec 11, 2024 |
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Ep. #14 | Books That Changed My Real Estate and Entrepreneurial Journey - The Long Game by Ryan Richards
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Nov 27, 2024 |
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Ep. #13 | How to Qualify for a Mortgage: Key Factors and Smart Strategies - The Long Game by Ryan Richards
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Nov 12, 2024 |
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Ep. #12 | From Corporate Ladder to 175 Doors This Year: How Andrew Freed Achieved Real Estate Success Through Syndication - The Long Game by Ryan Richards
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Oct 29, 2024 |
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Ep. #11 | Road to 312 Units: Zack Gray's Journey from Food Stamps to Financial Freedom - The Long Game by Ryan Richards
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Oct 15, 2024 |
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Ep. #10 | What I Wish I Knew Starting Out: Key Lessons for Homebuyers, Investors, and Aspiring Real Estate Professionals with Ryan Richards - The Long Game
|
Oct 01, 2024 |
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Ep. #9 | Demystifying the Mortgage Process: A Comprehensive Guide with Ryan Richards - The Long Game
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Sep 17, 2024 |
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Ep. #8 | Creative Financing, Subto Deals and Fix-and-Flips Featuring Tony Eisenhower - The Long Game by Ryan Richards
|
Sep 04, 2024 |
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Ep. #7 | How to House Hack Your Way Up with Gabby Demac & Ryan Richards - The Long Game
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Aug 21, 2024 |
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Ep. #6 | First Time Homebuying in Rhode Island with Brooke Buckett & Ryan Richards - The Long Game
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Aug 06, 2024 |
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Ep. #5 | Principles of Commercial Real Estate with Ben Cabone & Ryan Richards - The Long Game
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Jul 23, 2024 |
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Ep. #4 | Breaking down trusts, LLC's, and estate planning with Attorney Joshua Cali - The Long Game
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Nov 28, 2022 |
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Ep. #3 | Inside the current Real Estate Market with Steve Pizzarella - The Long Game
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Nov 02, 2022 |
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Ep. #2 | Inside the Rhode Island housing market with Ryan Richards and Brooke Buckett - The Long Game
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Oct 04, 2022 |
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Ep. #1 | Inside the Worcester Real Estate Market with Kyle Josephs - The Long Game
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Sep 27, 2022 |