The Long Game by Ryan Richards

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 t...

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...

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...

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 year...

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 membe...

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 wa...

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 wal...

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...

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 p...

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 employee...

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 m...

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 tim...

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 h...

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’r...

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 bu...

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...

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. H...

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...

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 e...

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...

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...

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...

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 a...

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 systems, buying back your time, and stacking ventures that actually complement each other instead of draining your focus. Ben shares what he is working on across...

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 show is about the evolution from operator to owner, from solopreneur to CEO. We’ll still talk real estate and investing, but the focus shifts to how businesses are built to l...