The Long Game by Ryan Richards

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 estate investing: before you choose a strategy, you need to know why you're investing in the first place. The vehicle only works if it matches the goal. Someone chasing generational wealth and someone chasing quick cash are not looking for the same investment, and treating them like they are is one of the most common and costly mistakes new investors make.

He walks through the three main investing paths, flipping, multifamily, and short-term rentals like Airbnb, and maps each one to the type of investor it actually suits: the time you have, the capital you can deploy, the hands-on involvement you're willing to take on, and the long-term outcome you're building toward. The framework is simple, but most people skip it entirely.

What You'll Learn:

• Why your first investment property is almost always a crash course, and why that's exactly the point
• How to identify your core investing objective before you choose a strategy, and why getting that backwards is so costly
• The key differences between flipping, multifamily investing, and short-term rentals, and which type of investor each one actually suits
• Why multifamily is one of the most effective long-term wealth-building vehicles for investors who don't have unlimited time
• How to factor property management into your underwriting from the start so it doesn't catch you off guard later
• Why Airbnb is a business first and a real estate investment second, and what that distinction means before you commit
• How aligning your strategy with your availability, capital, and goals puts your effort in the highest-value places from day one

If you're thinking about getting into real estate investing but aren't sure which path makes sense for you, this episode gives you an honest and practical framework for making that decision before you spend a dollar.

Interested in connecting?

HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
[email protected] | www.financewithteamrichards.com 
204 Turnpike Rd, Westborough, MA 01581
Licensed in CT, FL, MA, ME, NH, RI, NC, PA, TN, VT

Follow us on Instagram @financewithteamrichards @the.longgamepodcast

#TheLongGamePodcast #FinanceWithTeamRichards

Chapters:
00:00 Starting With Purpose
00:33 First Deal Crash Course
01:24 The Long Game Mindset
01:44 Pick Your Strategy
02:32 Time Versus Effort
03:23 Multifamily With Help
03:54 Airbnb Is A Business
04:14 Define Your Objective
04:35 Final Takeaways

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 transactions in its first full year as a team, We Stage Homes has completed over 65 stages in seven months after starting on a whim with a Google Doc, and a 130-unit acquisition in Maine is weeks away from closing.

They also dive into an Ascend Summit postmortem, providing takeaways from each of the speakers and panelists that helped make the event the success that it was.

What You'll Learn:

• How We Close Deals grew from a collective 50 million to 200 million in gross sales in just 12 months, and what actually drove that growth
• Why the moment you start building a team is the moment you finally understand how your business really works
• How to decide which tasks belong to you and which ones to offload, especially when you're running multiple businesses at once
• Why managing your own properties might be costing you more than you realize, and how opportunity cost should drive that decision
• What urgency actually looks like in practice, and why the wealthiest operators respond the fastest
• The Ascend Summit postmortem: key lessons from the speakers
• Why culture isn't built in team meetings. It's built in the small moments, the birthday cakes, the names you remember, the wins you celebrate together

If you're managing multiple businesses or building a team and trying to figure out how to do more without losing the things that made you successful in the first place, this episode is an honest and energizing look at what that process actually requires.

Interested in connecting?

GUEST
Ben Carbone
Team Lead, We Close Deals | Co-Owner, We Stage Homes | Owner, Woodstock Estates
[email protected] | https://www.weclosedealsteam.com 
Instagram: @ben.carbone | @weclosedealsteam 

HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
[email protected] | 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 Episode Setup
01:34 Ben Returns
01:58 Scaling Lessons
04:02 We Close Deals Growth
06:49 Leadership Mirror
11:16 Launching Staging Company
14:14 Delegation Decisions
17:39 Urgency and Focus
22:08 Downtime CEO Mindset
24:45 Working On Business
25:24 Mortgage Push Pull
26:41 Hiring Key Players
27:12 Seamless Partner Communication
28:13 Blueprinting Closings Together
28:41 From Vendors to Partners
29:14 Hiring for Growth
29:36 Stop Self Managing Rentals
31:14 Buying Back Your Time
33:09 Scaling With Property Managers
34:19 Ascend Summit Recap
35:33 Anthony Lamacchia Lessons
39:46 Culture and Leadership Standards
40:57 CJ Sincotta Focus and Scale
46:22 Principles and Closing Thoughts

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 status quo isn't a sign of dysfunction. It's the engine of a well-run operation. The people actually doing the work are the ones who see the inefficiencies most clearly, and if you've built a culture where they feel free to say so, you've given yourself a significant advantage.

Ryan also addresses the flip side: iteration without a foundation is chaos. Before you can optimize, you need a rhythm. Something as simple as a shared Google Sheet and a daily end-of-day recap creates the cadence your team needs to spot what's working and what isn't. Get the system down first, then find the right software to replace it.

What You'll Learn:

• Why 50 to 60% of Ryan's original onboarding plan has already been changed or cut, and why that's a sign the process is working
• How to set the right expectation with new hires from day one when you're building roles that have never existed before
• Why questioning everything, including your own systems, is a leadership principle worth instilling across your whole team
• What it looks like to do a 60 to 90-day reset: pruning what isn't working and doubling down on what is
• Why your employees often have better visibility into operational inefficiencies than you do, and how to unlock that perspective
• Why you should establish a simple foundational rhythm before you ever evaluate software or automation
• How to sequence the process correctly: get the work done first, identify the gaps, then find the tools that solve for them

If you're building a team and feeling the tension between having a plan and staying flexible enough to actually execute, this episode gives you a practical and honest look at how to hold both at the same time.

Interested in connecting?

HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
[email protected] | www.financewithteamrichards.com 
204 Turnpike Rd, Westborough, MA 01581
Licensed in CT, FL, MA, ME, NH, RI, NC, SC, PA, TN, VT

Follow us on Instagram @financewithteamrichards @the.longgamepodcast

#TheLongGamePodcast #FinanceWithTeamRichards

Chapters:
00:00 Plans Will Change
00:51 Hiring And Onboarding Lessons
01:46 Build The Plane Midair
02:28 Question Everything Culture
03:36 Empower Employee Initiative
04:24 Reset And Prune The Plan
05:17 Keep A Stable Backbone
06:08 Start Simple Before Software
07:18 Wrap Up And Next Updates

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, a relevant connection, a reason for someone to remember that you thought of them. That single shift, leading with generosity instead of a calendar invite, is what turns a business card into an actual relationship.

What You'll Learn:

• How to choose which markets and which events are worth your time, and which ones to cut
• Why finding the host first at any event is one of the highest-leverage moves you can make in the room
• How to become the person who connects people, and why that role compounds faster than any pitch ever will
• Why it's not only acceptable to exit a conversation that's going nowhere, it's the right call
• How to audit whether you're actually networking or just socializing with a drink in your hand
• Why a drawer full of business cards is a symptom of a follow-up problem, not a networking problem
• How to lead with value in your follow-up so you're memorable before you ever ask for anything

If you're putting time into networking but not seeing it translate into real business relationships, this episode gives you a practical and honest look at where the process is probably breaking down.

Interested in connecting?

HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
[email protected] | www.financewithteamrichards.com 
204 Turnpike Rd, Westborough, MA 01581
Licensed in CT, FL, MA, ME, NH, RI, NC, SC, PA, TN, VT

Follow us on Instagram @financewithteamrichards @the.longgamepodcast

#TheLongGamePodcast #FinanceWithTeamRichards

Chapters:
00:00 Why Networking Matters
00:55 Pick Your Market
01:55 Quality Over Quantity
02:41 Work The Host
03:27 Become The Connector
03:59 Exit Dead End Chats
05:24 Follow Up With Value
06:03 Skip The Coffee Trap
07:00 Stay In Touch Systems
07:30 Final Networking Mindset

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 content, your voice, and who you choose to collaborate with are all communicating something to the market, whether you're intentional about it or not. He walks through how his own approach evolved, from early content that was purely mortgage-focused to a deliberate effort to show up as an investor, community builder, and podcast host as well, because if you don't talk about it, people simply won't know. He also gets into the audit process his team runs regularly to make sure what they're putting out still reflects where they're trying to go.

What You'll Learn:

• Why starting with a logo and color palette is the right first step but the wrong stopping point
• How to work backwards from the company you want to be rather than just documenting the one you are today
• Why "manifest into the company you want to become" is a more useful frame than "fake it till you make it"
• What a social media audit actually looks like in practice, and why Ryan's team runs them regularly
• How staying too narrow in your content can quietly limit how the market sees you and what opportunities find you
• Why cross-collaboration is a branding decision as much as a marketing one, and how to choose partners intentionally
• How the content you put out today is either building toward your future brand or drifting away from it

If you're building a business and putting out content without a clear picture of where it's all supposed to land, this episode gives you a practical framework for getting intentional about your brand before the market decides what it means for you.

Interested in connecting?

HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
[email protected] | 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 Branding Beyond Logos
01:25 Define Your Value Proposition
02:01 Brand for Your Future Self
02:43 Audit Your Content Strategy
03:02 Expand What You’re Known For
04:17 Confidence Shapes Perception
05:00 Collaborate With Intention
06:23 Final Takeaways

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
[email protected] | 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

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
[email protected] | 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 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
[email protected] | 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

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 
[email protected] | https://www.oneelevenrx.com 
Instagram: @jamie.injx | @oneelevenrx 

HOST
Ryan Richards | Branch Manager, Northpoint Mortgage | NMLS 1987735
[email protected] | 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

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
[email protected] | 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