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The Long Game by 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.
Episodes
90 episodes
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 bigg...
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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 take...
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 mark...
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 ...
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, Ry...
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...
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 ofte...
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,...
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 ...
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...
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-prod...
Ep. #79 | From Operator to Owner: How to Break Through Your Ceiling
Most entrepreneurs don’t actually have a time problem… They have a capacity problem.In this episode of The Long Game Podcast, we break down one of the biggest transitions in business, the shift from being self-employed to becoming a true...
Ep. #78 | Stop Chasing Leads and Fix Your Processes
Most entrepreneurs don’t actually have a lead problem… they have a process problem. In this episode of The Long Game Podcast, we break down one of the biggest misconceptions in business growth. The idea that more leads automatically...
Ep. #77 | From Solo Agent to Scalable Business: Lessons from Nate Rock
In this episode of The Long Game, Ryan Richards sits down with Nate Rock to break down what it really takes to evolve from a solo real estate agent into a scalable business owner. From starting in Boston with zero connections to building and re...
Ep. #76 | Artificial Intelligence in the Real Estate Industry - Current Status and Future Predictions
In this solo episode of The Long Game Podcast, Ryan Richards breaks down how artificial intelligence is actually being used today in real estate and mortgage businesses, and where he guesses it’s all heading next.From AI replacing tradit...
Ep. #75 | How Authentic Marketing Wins in the AI Era with Tara Ostromecky
In this episode of The Long Game, Ryan Richards sits down with Tara Ostromecky, founder and CEO of Makin' It Marketing, for a conversation about what it really takes to grow a business in today’s fast-changing marketing landscape.Tara sh...
Ep. #74 | Stop Overthinking: A Simple Framework for Better Business Decisions
In this solo episode of The Long Game, Ryan Richards dives into one of the biggest hidden obstacles for entrepreneurs: analysis paralysis. Ryan shares a mindset shift that has changed the way he approaches decisions in business. As ...
Ep. #73 | From “Boots on the Ground” to Building a Scalable Operation with Grindstone Sealcoating
In episode 73 of The Long Game, Ryan sits down with Nick Lavallee and Nathan Hoy, the co-owners of Grindstone Sealcoating, to talk about what it really looks like to evolve from solopreneurs doing everything themselves into operators building a...
Ep. #72 | The Operator’s Journey: Understanding Business Seasons
In this solo episode of The Long Game Podcast, Ryan Richards breaks down a concept that every serious entrepreneur needs to understand: business happens in seasons.Ryan walks through the different phases of growth, from grinding it out ...
Ep. #71 | Phases of Entrepreneurship: From Doing the Work to Building the Vision
In this solo episode of The Long Game, Ryan Richards breaks down one of the most important transitions an entrepreneur will ever make: the shift from being the worker in the business to becoming the operator and visionary behind it.Ryan ...
Ep. #70 | Systems, Partnerships, and the Power Couple Playbook With Tony and Ashley Eisenhauer
In this episode of The Long Game, Ryan Richards sits down with Tony and Ashley Eisenhauer, a real estate power couple based in Northern Connecticut who are scaling fast across multiple ventures, from fix and flips and long-term rentals to short...
Ep. #69 | Manifesting Your Legacy with Ben Carbone
On this episode of the Long Game, Ryan sits down with repeat guest Ben Carbone to talk about what it really looks like when an operator starts thinking like a CEO. They dig into the mindset shift from doing everything yourself to building syste...
Ep. #68 | Welcome to The Long Game
This episode marks a turning point. Welcome to The Long Game Podcast!With the launch of The Long Game, the conversation expands beyond tactics, deals, and transactions and into vision, systems, and long-term thinking. This ...
Ep. #67 | When Does It Make Sense to Sell a Rental Property?
One of the hardest decisions in real estate investing is knowing when to hold and when to sell. In this solo episode of The Real Estate Lens, investor Ryan Richards breaks down how to evaluate whether a rental property is truly perform...
Ep. #66 | Capital Expenditures: Planning for Unexpected (And Expected) Repairs
If you own rental properties long enough, it's not a matter of if something breaks - it's when. In this solo episode of the Real Estate Lens, multi-family investor Ryan Richards breaks down the reality of repairs, ...