The Long Game by Ryan Richards

By Ryan Richards

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Category: Entrepreneurship

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Episodes: 87

Description

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