Anticipating Success with Early Hiring - The Long Game - Ep. #86

The Ascend Summit: A Story of Consistency & Perseverance - The Long Game - Ep. #92

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 in Florida, a Google Doc, and a conversation with his business partner Ben Carbone about why there was nothing like that in New England. What followed was a mastermind with 12 students, then a first summit of around 100 people, then a gradual expansion in scope, content, and vision that culminated in the 2026 Ascend Summit: 150 attendees, five panelists, a keynote speaker running a billion-dollar company, and a production team of 15. None of it happened at once. All of it happened because they stayed the course. What You'll Learn: * How the Ascend Summit went from an idea and a Google Doc to a 150-person event with a billion-dollar keynote speaker * Why most businesses fail not because of a bad idea or weak work ethic, but because they stop too soon * What Angelo Purina's story of working 72-hour stretches in a commercial kitchen teaches about what commitment to a vision actually looks like * Why the best time to hire is 12 months before you think you need to, and what it costs to wait until it feels obvious * How shiny object syndrome and the impulse to quit are often the same problem wearing different masks * Why staying the course on one thing, even slowly, compounds in ways that starting five new things never will * What it looks like to build something from nothing in public, including the social media cadence, the community, and the events that make it real If you're sitting on an idea you keep starting and stopping, or a business that's growing but not fast enough, this episode is a direct and honest case for what it actually takes to see something through. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in CT, FL, MA, ME, NH, RI, NC, SC, PA, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Big Ideas Intro 00:07 Conference Spark 01:01 Launching Informed Investor 01:23 Ascend Summit 2026 Highlights 02:10 Perseverance Pays Off 03:35 From Google Doc to Mastermind 04:06 First Summit and Bigger Vision 04:38 Building Community and Content 05:34 Loving the Grind 06:05 Angelo’s 72 Hour Hustle 06:55 Hire Before You Need To 07:59 Looking Ahead and Wrap Up

Shiny Object Syndrome - The Long Game - Ep. #91

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 fact that neither comes from bad intentions. The person who rushes through a document review isn't cutting corners on purpose. But slow is fast, and the cost of catching a problem at the wrong stage is almost always higher than the cost of taking an extra ten minutes upfront. He also gets into the decisions people don't realize they're making, specifically where they place their attention. Shiny object syndrome isn't just a distraction. It's a choice, and most of the time it's a subconscious one. What You'll Learn: * Why making a decision quickly and making it well are not the same thing, and how to know which one a situation calls for * The specific moment in a workflow where slowing down saves more time than any shortcut ever could * Why "slow is fast" is one of the most practical frameworks for a growing team to internalize * How shiny object syndrome operates as a subconscious decision, and what it quietly costs your business * Why Ryan pulled back from real estate investing for the better part of a year, and what that focus produced * How to identify the highest ROI use of your attention when multiple opportunities are competing for it * What it looks like to correct your direction intentionally rather than drift toward wherever your habits point If you're running a growing business and finding that things are falling through the cracks despite everyone working hard, this episode gives you a clear framework for why that happens and what to do about it. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in CT, FL, MA, ME, NH, RI, NC, SC, PA, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Decisions Fast or Slow 00:51 Too Much on Your Plate 01:46 Slow Is Fast Example 03:45 Low Stakes Quick Calls 04:13 Attention and Focus Choice 04:48 Doubling Down to Grow 05:44 ROI and Recalibration 06:37 Final Takeaways

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 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 can unlock a perspective no conference in your own niche ever would.  He walks through how this philosophy shaped his own trajectory, from showing up alone in a suit to a Worcester networking event, to building some of his closest business partnerships and finding his path into real estate investing entirely through the connections made that evening. What You'll Learn: * Why cross-industry rooms produce more meaningful perspective shifts than staying in your own niche * What the power of proximity actually looks like in practice, and why it's rarely the "golden key" moment people expect * How Ryan's entire path into real estate investing started from one networking event he almost skipped * Why the mindset of someone running an eight or nine-figure company looks fundamentally different, and what you can absorb just by being in the room * How two people who met at a single event after hours went on to build multiple eight-figure companies together * Why showing up alone, not knowing anyone, is often where the most important connections begin * What Ryan set out to create with the Ascend Summit, and why the philosophy behind it goes back to this exact idea If you're someone who keeps putting off the event, the meetup, or the room you know you should be in, this episode is a direct and honest case for why that next step might be the one that changes everything. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Why Create This Room 00:30 Power of Proximity 00:41 Cross Industry Perspectives 01:26 Connections Not Secrets 02:25 Why Ascend Summit Exists 02:38 Event Stories That Changed Everything 03:26 My Networking Event Turning Point 03:52 Showing Up Alone 04:11 Meet Five People Rule 04:48 Thinking Like Bigger Operators 05:26 Bigger Problems Bigger Decisions 06:02 Your Circle Shapes Trajectory 06:22 Final Takeaways

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 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 felt like something was missing. She started with spray tans out of her house, bootstrapped her way into aesthetics, and built a team of 14 doing multiple seven figures annually. Her path wasn't linear, and she doesn't pretend it was.  They talk about why Jamie hires for bedside manner over skill, what it means to "eat last" as a leader, how she navigated finding a compliant medical director partnership in one of the most regulated states in the country, and why staying honest with your team is the foundation everything else is built on. What You'll Learn: * Why the med spa industry is far more medically serious than its Instagram presence suggests, and what compliance really looks like for an RN-owned practice in Massachusetts * How Jamie went from spray tans out of her house to a team of 14 doing multiple seven figures, and what the bootstrapped middle looked like * Why hiring for bedside manner and cultural fit beats hiring for technical skill every time * What "eating last" actually looks like in practice, and why it's the single best thing a leader can do to build team loyalty * How to know when you're ready to open a second location, and why opening too early is one of the most common mistakes in growing businesses * Why building a business forces you to confront your own blind spots, whether you're ready to or not * How to think about the nature versus nurture question as an entrepreneur who learned the game from watching a parent do it first If you're building a business in a service industry and trying to figure out how to grow without losing the personal touch that got you there, this episode is a practical and honest look at what that actually requires. Interested in connecting? GUEST Jamie Sanborn Founder, One Eleven RX  jamie@oneelevenrx.com | https://www.oneelevenrx.com  Instagram: @jamie.injx | @oneelevenrx  HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Intro 01:03 Meet Jamie Sanborn 02:40 From Spray Tans to Botox 04:53 Making the Leap 08:38 Growth Goals and Scaling 10:37 Hiring and Culture Fit 15:33 Leading with Service 19:05 Expansion Timing and Marketing 20:24 Cash Flow and Inventory Lessons 26:39 Finding the Right MD Partner 27:33 Doctor Partnership Setup 28:55 Staying Compliant 31:12 Choosing Core Services 32:53 Building Specialist Team 33:40 From Operator to Leader 35:59 Entrepreneur Mindset Reality 38:12 Injection Risks Training 39:47 Botox vs Filler Explained 44:34 Mentorship Full Circle 45:56 Advice Nature Nurture Wrap

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 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 two people could walk in and hit the ground running. He's transparent about what worked, what didn't, and why most of the systems he built were meant to be reshaped on the fly. The real value wasn't in getting it perfect. It was in having a foundation. What You'll Learn: * Why most entrepreneurs' hiring problem is actually a systems problem in disguise * How to document your own processes before you can effectively hand them off to someone else * Why imperfect action still requires a baseline level of organization to succeed * What "intangibles" actually look like when you're hiring for a small, growing team * Why technical skill and cultural fit are not the same thing, and which one matters more * How to create enough autonomy that a new hire can contribute from day one without constant hand-holding * Why Ryan went from a team of three to a team of five in two weeks, and what that decision taught him If you're running your own business and feeling the pull to hire but keep stalling, this episode gives you a practical, honest look at what it actually takes to bring someone on and make it work. Interested in connecting? HOST Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735 rrichards@trynorthpoint.com | www.financewithteamrichards.com  204 Turnpike Rd, Westborough, MA 01581 Licensed in MA, CT, FL, NC, NH, PA, RI, ME, TN Follow us on Instagram @financewithteamrichards @the.longgamepodcast #TheLongGamePodcast #FinanceWithTeamRichards Chapters: 00:00 Hiring Hesitation 00:21 Two New Hires Update 00:55 Regret And Readiness 01:37 Scaling Fast To Five 02:01 Documenting Your Work 03:08 Build A Company OS 03:55 Plans Will Change 04:23 Hire For Intangibles 05:56 Know Your Strengths 06:22 Blueprint For Autonomy 06:53 One Month In Results 07:04 What's Next Growth Plan