The Long Game by Ryan Richards

What would you do if your financing contingency passed and your $10,000 deposit went with it?

In this episode of The Long Game Podcast, Ryan shares three real stories from the past year to mark Halloween: a buyer who lost an earnest money deposit, a near miss with vacant land fraud, and an investor stretched too thin. The goal is practical lessons you can use before the same thing happens to you.

What You'll Learn:

Is now actually a bad time to buy real estate, or does it just look that way from the headlines?

In this episode of The Long Game Podcast, Ryan breaks down what’s actually happening in the real estate market right now, filmed in mid-October 2026, and why the conditions most buyers are treating as a reason to wait are the same conditions that create real opportunities for the people paying attention.

Ryan cuts through the noise on two fronts: rates and seasonality. The average 30-year fixed rate has climbed nearly a full percent in the la...

What does it take to go from flipping houses to moving over a million square feet of flooring across New England?

In this episode of The Long Game Podcast, Ryan sits down with Bruno Maluf, owner of LVP Direct, a direct-to-consumer luxury vinyl plank company selling wholesale-priced flooring across New England, to talk about how a frustrating supply chain problem on a flip turned into a business doing millions in revenue, and what it actually took to get there.

Ryan and Bruno go deep on the conversations most entrepreneurs avoid: the relationship between personal development...

What if the role you’ve been struggling to fill doesn’t have to fit into one lane?

In this episode of The Long Game Podcast, Ryan shares the framework that unlocked his approach to building a team, and why the single biggest mistake entrepreneurs make when looking for their first or next hire is thinking about the role in one dimension.

Ryan makes the case that the “I need to hire an admin” or “I need to hire a salesperson” mindset is exactly what keeps solo operators stuck. If you can only picture a hire filling...

Eight years, 60 units, and 80+ homes a year. Here's what the market actually looks like from the inside.

In this episode of The Long Game Podcast, Ryan sits down with Rich Jenkins, a top real estate agent in Central Massachusetts selling over 80 homes per year and a real estate investor with 60 units across Worcester County, to talk about what the market looks like heading into fall 2026, how buyers and investors are winning right now, and what separates the agents and advisors who build long-term clients from the ones who close a deal and disappear.

Ryan and...

Most buyers focus on finding the right house. The best agents help you find the right life.

In this episode of The Long Game Podcast, Ryan sits down with Brooke Buckett, a Rhode Island-based real estate agent specializing in relocation and community matchmaking, to talk about what a truly great agent actually does, and why the difference between a good transaction and a great one often comes down to the conversations most agents never have.

Ryan and Brooke also dig into the lending side of the equation, specifically how buyer strategy and financing strategy have...

Going viral sounds great. For most local businesses, it's the wrong goal entirely.

In this episode of The Long Game Podcast, Ryan sits down with Russ Mangsen, social media strategist and host of Networking Over Nine, and Alex Fischer, Team Richards' marketing manager, for a round-table conversation on what's actually working in content and marketing right now, and what most business owners are getting completely wrong.

The conversation kicks off with Judy's Pancakes and how she's a case study in why follower count and business success are not the same metric. They also get into...

Most people think the homebuying process starts with finding a house. It doesn't.

In this episode of The Long Game Podcast, Ryan shares exactly what he'd do if he were buying a house in 2026, drawing on his experience as a mortgage lender and purchasing six properties of his own in the last three years.

Most prospective buyers walk into the process with false assumptions about what they can afford, how much cash they actually have available, and what they truly need in a property versus what they've just convinced themselves they need. Getting honest about...

What if the fastest way to improve your business was already sitting on your team?

In this episode of The Long Game Podcast, Ryan shares the system he's been building over the past six months to make feedback a daily habit rather than a quarterly event, and why that shift has moved his team further on the systems side in half a year than he expected.

He also walks through two practical tools his team has been using: a living document where team members can submit suggestions for process improvements, and a workload audit that...

Can someone land on your page and know what you do in 30 seconds?

In this episode of The Long Game Podcast, Ryan marks episode 100 with something more useful than a celebration: an honest look at where his marketing and branding actually stand.

Ryan draws a clear line between content creation and branding, and makes the case that most businesses, including his own, conflate the two. Posting consistently is the foundation, and getting there is a real accomplishment. But once that rhythm is in place, the next question matters just as much: can someone land on...

99 episodes in… here's what three years of The Long Game looks like.

In this episode of The Long Game Podcast, Ryan reflects on nearly three years of building the show from the ground up. From a real estate and finance platform to something he didn't fully anticipate when he started: a living record of his own professional development.

Ryan shares how the podcast has evolved alongside him, from solo loan officer to a team of five, from The Real Estate Lens to The Long Game, and from sharing information to pulling back the curtain on ho...

AI won't replace the human touch. But it will replace the humans who ignore it.

In this episode of The Long Game Podcast, Ryan sits down with David Hill, serial entrepreneur, sales trainer, marketer, and real estate agent, to talk about what it actually looks like to integrate AI into your business today, before most people have figured out how serious this moment really is.

David brings two days of insights from a private event with John Lee, breaking down the WAVIT framework: five categories of AI use, written, audio, video, imagery, and tech, each...

Burning down your shed can be a strong deterrent for first time rental owners… here’s what you can learn from it.

In this episode of The Long Game Podcast, Ryan shares what his first rental property actually taught him, starting with a five-unit multifamily that threw everything at him at once: evictions, bedbugs, electrical problems, non-payment of gas accounts, troubled tenants, and one tenant who burned down his shed. None of it was in the plan. All of it was education.

Ryan uses that experience as a jumping-off point for a broader framework on real...

You don't truly understand your business until you start building a team around it.

In this episode of The Long Game Podcast, Ryan sits down with his business partner Ben Carbone, team lead of We Close Deals, co-owner of We Stage Homes, and owner of Woodstock Estates, for a wide-ranging conversation on what it actually looks like to run multiple businesses at once, make smart hiring decisions, and lead a team that believes in the mission.

Ben shares where things stand across his portfolio: We Close Deals is on pace to do over $200 million in...

The plan you start with is rarely the plan that works. That's not failure, that's how it's supposed to go.

In this episode of The Long Game Podcast, Ryan shares what he's learned in the 60 to 90 days since bringing on his two most recent hires, and why roughly half of the systems, SOPs, and plans he built before they arrived have already been shelved, adjusted, or rebuilt from scratch.

He draws on a principle from The Algorithm by John McNeill, which examines Elon Musk's operating philosophy, to make the point that questioning the...

Most people leave networking events with a stack of business cards and nothing to show for it. Here's why.

In this episode of The Long Game Podcast, Ryan breaks down how he built his network intentionally across Worcester, Providence, and eventually Boston, and shares the specific strategies he wishes he had known when he was filling his calendar with five events a week and talking to everyone without a plan.

He also reframes the follow-up entirely. The goal isn't to book ten coffee meetings. It's to show up with something of value, a warm introduction...

When you think of branding, you’re probably thinking of a logo. But those who build something lasting start with the impact and work backwards from there.

In this episode of The Long Game Podcast, Ryan breaks down what he wishes he had known about branding when he started, why the logo-and-colors phase is just the surface, and how to build a brand that speaks to the company you're becoming, not just the one you are today.

Ryan makes the case that branding is not a design exercise, but a strategic one. Your colors, your co...

Most people don't fail because the idea was bad. They fail because they quit before it had time to work.

In this episode of The Long Game Podcast, Ryan shares the origin story of the Ascend Summit and the lessons from this year's event that hit closest to home: what perseverance actually looks like in practice, why consistency is the variable most people underestimate, and why the best time to hire is always earlier than feels comfortable.

Ryan walks through how the Ascend Summit started three years ago with a trip to the Clever Summit...

The most expensive decisions aren't the ones you got wrong. They're the ones you made too fast.

In this episode of The Long Game Podcast, Ryan breaks down how he thinks about decision-making as a leader, why the speed of a decision matters as much as the decision itself, and what he's been actively teaching his team as his business grows.

Ryan walks through the two failure modes he sees most often: moving too quickly on tasks that deserve a pause, and letting attention scatter across too many priorities at once. He's direct about the...

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...

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...

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...

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...

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...

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...

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...

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...

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 t...

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.

Usin...

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 i...

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 business owner. Because if everything in your business relies on you, growth will always hit a ceiling.

If you’ve ever felt maxed out, overwhelmed, or like you’re doing everything yourself, this episode will challenge how you think about scaling. It’s not about working more hours, it’s about building systems and leveraging p...

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 fix everything. The reality? Without the right systems in place, even the best opportunities fall through the cracks.

If you’ve ever felt stuck trying to “get more business,” this episode will challenge how you think about growth, sales, and scaling. It’s not about chasing one-off opportunities, it’s about building repeatable processes that consistently generate result...

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 refining a high-performing team, Nate shares the lessons, mistakes, and mindset shifts that fueled his growth.

The conversation dives deep into the transition every entrepreneur faces—moving from doing the work to building systems, people, and processes that allow you to grow beyond yourself. Nate opens up about leadership, hiring, delegation, and why tr...

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 traditional search engines to becoming a fully integrated personal assistant, Ryan shares how these tools are changing the way professionals operate on a daily basis. He also dives into the opportunities and limitations of AI, especially when it comes to data, automation, and decision-making in high-stakes industries like real estate and finance.

Ryan explores emerging tools li...

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 shares how she turned a passion for creativity and entrepreneurship into a nationally-serving marketing company based in Worcester, serving clients across the country. From building her business at a young age to hiring her first team members, Tara opens up about the lessons she has learned around growth, leadership, authenticity, and adapting in the age of AI.

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 you grow and gain momentum, the fear of making the wrong move can creep in. But inaction is often more damaging than a mistake.

He breaks down a simple framework for evaluating decisions by asking one key question: Will this fundamentally change the trajectory of my business or go against my values? If the answer is no, m...

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 business that can grow without them in the field every day.

Nick and Nate break down their asphalt maintenance business model, why education is such a big part of winning customers, and the exact inflection point where they realized they were capped on revenue if they stayed “boots on the ground.” From 10-hour sealcoating days followed by quoting jobs...

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 as a solo operator to hitting the tipping point where revenue is no longer the problem, capacity is. He shares how the skills that get you from zero to your first $100,000 are not the same skills required to scale beyond it, and why recognizing your current season is the key to unlocking the next one.

This episode...

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 walks through the early phase of entrepreneurship where success is directly tied to effort. More calls, more hours, more hustle. While that phase is necessary, it is not sustainable if the goal is real scale. This episode is a deep dive into what happens next, and how entrepreneurs can intentionally realign their daily work with a...

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-term rentals and home staging.

This conversation is all about what changes when you stop thinking like a worker and start thinking like an operator. Tony and Ashley break down the systems mindset behind building more without burning out, including how they buy back their time, build the right team, and make strategic decisions that compound over...