The Long Game by Ryan Richards

Inside the Mind of a CEO with Andrew Bosco - The Long Game - Ep. #85

1 h 5 min · 19. maj 2026
episode Inside the Mind of a CEO with Andrew Bosco - The Long Game - Ep. #85 cover

Description

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 on a mission to help one million people reach financial independence through real estate. He shares how imposter syndrome followed him into the role, why he initially said no, and what ultimately made him put the gas on the fire and commit. What You'll Learn: * Why shifting from a 100-foot to a 10,000-foot view changes how you lead and build * How Andrew went from imposter syndrome to CEO and what changed between the first no and the final yes * What a system actually is and how people, processes, and technology work together * Why focus is the ultimate superpower in an era of infinite distraction * How to implement automation and new software without overwhelming your team * Why the worst thing you can do is nothing  If you're an entrepreneur, business owner, or operator trying to think bigger, build smarter, and stop getting in your own way, this one's for you. Interested in connecting? GUEST Andrew Bosco CEO, Candor Investment Group | Founder, Granite & Pine Properties a.bosco.realestate@gmail.com | candorinvestmentgroup.com Instagram: @candorinvestmentgroup  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 02:13 Andrew’s Background 03:18 Why He Became CEO 04:53 CEO Mindset Shift 07:56 Saying Yes Faster 11:13 Focus and Consistency 15:13 Authenticity Over Polish 18:21 Systems and Processes 22:59 Empowering the Team 26:31 Automation and Tools 35:49 BRRRR Strategy Explained 37:10 Perfect Day Freedom Goal 41:22 Calendar Control Systems 47:20 Meeting Days and Prospecting 52:26 Delegation and Partnerships 56:02 Imperfect Action Mindset 01:01:09 Community Beats Fear 01:04:19 Final Take Action Push

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89 episodes

episode Prioritizing People Over Profit with Jamie Sanborn - The Long Game - Ep. #89 artwork

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

Yesterday46 min
episode Building The Plane In The Air - The Long Game - Ep. #88 artwork

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

9. juni 20267 min
episode From Ideas to Action with Carolyn Hearn - The Long Game - Ep. #87 artwork

From Ideas to Action with Carolyn Hearn - The Long Game - Ep. #87

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2. juni 202656 min
episode Anticipating Success with Early Hiring - The Long Game - Ep. #86 artwork

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, 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 watch quality slip. He unpacks the "snowball" problem, where hesitation hands your competitors the time they need to close the gap.  Find the right person, build the systems together, and stop letting the fear of imperfection slow down what is already working. What You'll Learn: * Why hiring when you're already overwhelmed makes the process harder, not easier * How waiting too long forces a costly trade-off between promoting new business and serving existing clients * Why momentum is more valuable than perfection when you're in a growth phase * How delaying a hire gives competitors time to catch up on what makes your approach unique * Why you don't need a complete SOP or perfect systems before bringing someone on * The mental shift from "I can't afford to hire" to "I can't afford not to" * How to frame a new role honestly with candidates when you're building the position from scratch If you're a business owner who keeps saying you need help but keeps putting off the hire, this episode will show you exactly what that delay is costing you, and what to do about it instead. 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 Reflecting on Growth 01:02 The Hiring Lesson 01:45 Capacity Kills Promotion 02:16 Service vs Sales Tradeoff 03:35 Momentum and Competition 04:17 Fear and Worst Case 06:36 Building the Team Vision 07:00 Final Takeaway

26. maj 20267 min
episode Inside the Mind of a CEO with Andrew Bosco - The Long Game - Ep. #85 artwork

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 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 on a mission to help one million people reach financial independence through real estate. He shares how imposter syndrome followed him into the role, why he initially said no, and what ultimately made him put the gas on the fire and commit. What You'll Learn: * Why shifting from a 100-foot to a 10,000-foot view changes how you lead and build * How Andrew went from imposter syndrome to CEO and what changed between the first no and the final yes * What a system actually is and how people, processes, and technology work together * Why focus is the ultimate superpower in an era of infinite distraction * How to implement automation and new software without overwhelming your team * Why the worst thing you can do is nothing  If you're an entrepreneur, business owner, or operator trying to think bigger, build smarter, and stop getting in your own way, this one's for you. Interested in connecting? GUEST Andrew Bosco CEO, Candor Investment Group | Founder, Granite & Pine Properties a.bosco.realestate@gmail.com | candorinvestmentgroup.com Instagram: @candorinvestmentgroup  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 02:13 Andrew’s Background 03:18 Why He Became CEO 04:53 CEO Mindset Shift 07:56 Saying Yes Faster 11:13 Focus and Consistency 15:13 Authenticity Over Polish 18:21 Systems and Processes 22:59 Empowering the Team 26:31 Automation and Tools 35:49 BRRRR Strategy Explained 37:10 Perfect Day Freedom Goal 41:22 Calendar Control Systems 47:20 Meeting Days and Prospecting 52:26 Delegation and Partnerships 56:02 Imperfect Action Mindset 01:01:09 Community Beats Fear 01:04:19 Final Take Action Push

19. maj 20261 h 5 min