Join The Standard here: https://thestandardmen.com/

Jeremy Freeman is an entrepreneur in the dental industry, co-owning multiple dental practices with his wife and scaling from a single office to a multi-location operation. He has spent years learning how to transition from practitioner to business operator, implementing systems, sales frameworks, and leadership development to grow revenue and profitability. His experience spans business consulting, team leadership, and navigating major economic disruptions like COVID while continuing to scale.

In this episode, we discuss:

• Why most business owners are skilled operators—but poor leaders
• The shift from “doing the work” to actually leading a company
• How learning sales transformed a healthcare-based business
• The real impact of hiring the right consultant at the right time
• Lessons from scaling through financial pressure and uncertainty
• Why your business will only grow as much as you grow as a leader
• Balancing marriage, family, and business without compartmentalizing life
• The importance of environment, accountability, and community for high performers

The Legacy & Wealth Podcast, hosted by Mitchell Clark and presented by The Standard, features conversations with entrepreneurs, executives, and high-performing men who are building wealth, leadership, and legacy. Each episode dives into the realities of success, covering business growth, personal responsibility, and what it takes to create a meaningful life at a high level.

Timestamps

00:00 Introduction & early business struggles
01:05 How Jeremy Freeman makes money today
02:00 Expanding into cosmetic dentistry & sales
03:10 Entering entrepreneurship through marriage
04:30 Early challenges running a business
06:00 The turning point: hiring a consultant
09:00 Treating business like sales vs healthcare
12:00 COVID impact & near financial collapse
14:00 Leadership growth & the “law of the lid”
16:00 Transitioning from operator to leader
17:10 The worst day in business
21:00 The importance of emotional intelligence
23:30 Why he joined The Standard
26:00 Accountability and personal discipline
28:30 Blending business, marriage, and family life
33:00 Daily operations & managing by numbers
38:00 Communication in marriage under pressure
42:00 Raising children with values and independence
50:30 Long-term thinking vs instant success
54:50 Defining legacy and what truly matters

Join The Standard: Thestandardmen.com

Entrepreneur & Executive Howard Osaitile breaks down the realities of scaling a healthcare business from the ground up, managing risk under pressure, and redefining success beyond money. This is a conversation about discipline, ownership, and building a life that actually aligns with your long-term legacy.

Howard Osaitile is a healthcare consultant and entrepreneur specializing in university medical centers and residential assisted living operations. He owns and operates multiple assisted living facilities in Tennessee, generating over $1.4M in annual revenue with industry-leading margins. With a background in emerging technology, an MBA, and experience working with Fortune-level healthcare organizations, Howard combines corporate strategy with hands-on operational execution. His leadership spans both high-level consulting and building scalable, service-based businesses from scratch.

In this episode, we discuss:

• How Howard built a $1.4M assisted living business while working a full-time job
• The operational strategies that increased margins from 15–18% to over 30%
• Why most people fail in service businesses by treating them like passive investments
• The reality of scaling too fast and the lessons learned from early mistakes
• How to balance corporate stability with entrepreneurial risk-taking
• The concept of “seasons” vs. work-life balance for high-performing men
• Building a business with your spouse—and protecting the marriage in the process
• Why redefining failure is critical for long-term success

The Legacy & Wealth Podcast, hosted by Mitchell Clark and presented by The Standard, features conversations with entrepreneurs, executives, and high-performing men who are building wealth, leadership, and lasting legacy. Each episode provides real-world insights into business, family, and personal growth for men committed to operating at a higher level.

Timestamps

00:00 Building a 31% margin business in healthcare
00:54 Introduction to the podcast and guest
01:30 How Howard makes money (consulting + business)
03:30 Inside the assisted living business model
04:30 Revenue and profit margins breakdown
06:00 Early career and path into consulting
07:30 MBA decision and career acceleration
09:40 Starting a business during burnout and COVID
11:40 Learning from competitors and market demand
13:20 Leadership, culture, and operational excellence
14:30 First facility launch and occupancy strategy
18:00 Scaling quickly and early mistakes
20:00 Hiring challenges and leadership lessons
24:30 Managing risk while scaling multiple locations
26:00 Infrastructure limits and scaling constraints
28:00 Reaching 30%+ margins through systems and leverage
30:00 Redefining failure and increasing risk tolerance
31:30 Industry outlook and barriers to entry
34:00 Why Howard moved to Dallas
37:00 Building a business with your spouse
39:20 Daily routine and discipline
42:30 Protecting marriage while building a business
45:00 Work-life balance vs. “seasons” of life
50:00 Neglected pillars: emotional and spiritual health
52:30 Future plans: operator vs. investor
56:30 Leveraging corporate experience in entrepreneurship
57:30 Joining The Standard and the value of proximity
1:02:00 Building legacy through stewardship and leadership

Financial Expert and Owner of Stratum Ridge, Brandon Gerfen shares a powerful journey from a difficult childhood and military service to managing investments and advising high-net-worth clients. This conversation explores the mindset shifts, financial frameworks, and life lessons that shape men who are building wealth while protecting what matters most.

Brandon Gerfen is a wealth and investment manager with over a decade of experience in the financial industry. He began his career at JPMorgan Chase, quickly rising through the ranks before moving into private wealth management and helping grow a registered investment advisory firm managing billions in assets. After years of advising affluent clients and business owners, Brandon recently launched his own investment firm. His background also includes over a decade of service in the United States Marine Corps, including deployments overseas, which helped shape the discipline and perspective he brings to business and leadership.

In this episode, we discuss:

• How a challenging childhood and unstable home environment shaped Brandon’s drive and resilience
• The lessons the Marine Corps teaches about discipline, leadership, and responsibility
• Why many high earners with millions still don’t understand how money actually works
• The difference between earning money and managing wealth effectively
• The importance of structure and clarity when building a financial plan
• Why stability and consistency are often the defining traits of successful individuals
• The emotional side of money, family expectations, and helping others financially
• How high-net-worth individuals invest differently once they gain access to private markets

The Legacy & Wealth Podcast, hosted by Mitchell Clark and presented by The Standard, features conversations with entrepreneurs, executives, and high-performing men who are building wealth, leadership, and legacy. Each episode explores the strategies, lessons, and experiences behind success while addressing the responsibility that comes with leadership, family, and long-term impact.

Timestamps:
00:00 Introduction and opening discussion on money and entitlement
01:00 Introduction to the Legacy & Wealth Podcast
01:20 Brandon Gerfen’s current role as a wealth and investment manager
02:00 Career journey from JPMorgan to building his own firm
07:40 Brandon’s early life and difficult childhood environment
14:30 Joining the Marine Corps and lessons from military service
18:40 Deployments to Iraq and Afghanistan
20:50 Searching for camaraderie and brotherhood after the military
21:30 Why Brandon joined The Standard
25:30 Financial advising principles and helping clients plan their future
33:20 Common traits among high-net-worth individuals
36:30 The difference between entrepreneurs and intrapreneurs
40:20 Income levels and the point where lifestyle satisfaction plateaus
43:00 Investment strategies for clients with $10M+ net worth
48:50 Emotional decisions around helping family with money
52:30 The philosophy of saving, spending, and long-term freedom

Owner of PSG Security Rod Rodriguez opens up about the transition many high-performing men face in midlife. He details the pains that he went through losing two wives before the age of 50. He shares the challenges of being the one who protects and provides to becoming the man who leads, mentors, and builds lasting impact.

Rod Rodriguez is a veteran, security professional, entrepreneur, and leader committed to mentoring the next generation of men. He runs a private security contracting company while also building initiatives designed to create opportunities for veterans and law enforcement professionals transitioning into civilian life.

In this episode, Rod shares the reality of life after military service, building a security contracting business, and navigating the tension between success and calling. He explains the challenge of scaling a business beyond yourself, the responsibility of creating opportunities for other veterans, and the deeper questions many men face when they reach a season of stability but still feel called to something greater.

• The transition from military service to entrepreneurship
• Why many successful men still feel something is missing
• The challenge of scaling a service-based business beyond yourself
• Building a company that creates jobs and opportunities for veterans
• The importance of brotherhood and accountability among men
• Why midlife is often a season of leadership and influence
• The tension between comfort, calling, and personal growth

00:00 Introduction
02:00 Rod’s background and military service
06:00 Why brotherhood and community matter for high-performing men
08:30 The difference between mentorship and peer-level leadership
12:00 Finding men who challenge you instead of relying on you
16:00 The shift from being a “soldier” to becoming a “leader”
20:30 Building a private security business and landing contracts
25:00 The challenge of scaling a service-based business
28:00 Creating job opportunities for veterans and law enforcement
32:00 Wrestling with calling, purpose, and faith
38:00 Why growth requires discomfort and change
42:00 What the next season of leadership looks like

Follow Rod Rodriguez: https://www.instagram.com/psgrodrodriguez/

Multi-Million dollar developer Royce Colley shares the real path to building wealth through real estate—far beyond the simple “fix and flip” stories most people hear. In this episode, he breaks down how he built over 100 homes in the Dallas–Fort Worth area, the strategies investors use to create passive income, and the personal setbacks that nearly stopped his journey.

Royce is the real estate developer, investor, and mentor who has been building homes in the DFW area since 2015. Over the past decade, he has developed more than 100 homes and later launched a construction development school to teach others how to enter the real estate industry.

In this conversation, he explains how investors structure deals, how owner financing creates passive income, and why resilience is often the real differentiator between those who succeed in business and those who quit.

• How Royce built more than 100 homes in the Dallas–Fort Worth market
• The mindset shift that led him from corporate work into real estate investing
• Lessons from growing up in a single-parent household and learning construction early
• The real risks and misconceptions behind house flipping
• How owner financing works and why it can create passive income
• Rebuilding after personal bankruptcy and financial setbacks
• Why relationships and investors are critical to scaling real estate deals
• The realities of becoming a real estate developer

00:00 Introduction
03:55 How Royce currently makes money in real estate
04:30 Building over 100 homes in the DFW area
05:10 The Warren Buffett quote that sparked his interest in real estate
05:50 Leaving corporate America to start flipping houses
06:00 Growing up in Dallas in a single-parent household
07:10 Learning construction working with contractors as a teenager
12:30 The real path from house flipping to development
20:00 The challenges of scaling a real estate business
32:10 How owner financing deals actually work
33:00 Structuring wrap notes and creating passive income
41:20 Filing bankruptcy and eliminating $90,000 in personal debt
42:20 Rebuilding financially after bankruptcy
44:00 Finding investors and scaling the next phase of the business

Follow Royce on Instagram here: https://www.instagram.com/the.gentlemanbuilder/

3rd Generation Owner of Master Hatters of Texas Matt Cook shares the reality of leading a family manufacturing company, the responsibility of preserving American craftsmanship, and the personal turning point that forced him to redefine what legacy truly means.

Matt Cook operates Master Hatters of Texxas a Texas-based hat manufacturing company that has been producing cowboy hats, western hats, and lifestyle headwear for decades. The company traces its roots back to the 1930s when the original factory was built to manufacture hats in Garland, Texas, eventually producing products for major brands and developing its own lines.

In this conversation, Matt also opens up about one of the darkest moments of his life, when personal struggles forced him to confront the question of whether the family legacy would end with him—or continue into the future.

• The history of a family-run hat manufacturing business that began in the 1930s
• What it takes to preserve American manufacturing in a global economy
• Leadership lessons from running a multi-generational company
• Why treating employees like family matters in small businesses
• How adversity and personal struggles can become a turning point
• The role of faith and responsibility in rebuilding direction and purpose
• What it truly means to build a legacy that lasts beyond business

00:00 Introduction
01:25 The history of Matt Cook’s family hat manufacturing business
03:00 How the company started producing hats in Texas
06:40 Lessons from growing up around the family business
12:10 The realities of American manufacturing today
18:30 Leadership responsibilities in a family company
22:55 Navigating difficult seasons in business
24:00 How social media and events helped grow the brand
30:00 Why ambitious men search for stronger peer groups
36:30 What legacy means in business and life
38:00 Treating employees like family inside the company
01:08:20 A personal turning point that reshaped Matt’s life
01:10:00 The responsibility of continuing the family legacy

Follow Matt Cook on Instagram: https://www.instagram.com/masterhattersmatt/

Real estate investor and lending expert Ricardo Carrilllo reveals how the wealthy structure deals, why most people misunderstand real estate financing, and the strategies high-income investors use to build massive equity and reduce taxes legally.

Ricardo Carrillo runs a nationwide mortgage lending team that helps investors and entrepreneurs finance real estate across the United States. With relationships across more than 100 banks and access to thousands of loan programs, Ricardo works with investors ranging from first-time buyers to high-net-worth individuals building large real estate portfolios.

In this episode, Ricardo breaks down the financial strategies used by serious investors, how leverage and depreciation work in real estate, and why some of the wealthiest investors in the world pay little to no taxes legally through strategic investments.

• How Ricardo built a nationwide mortgage lending team
• The real estate financing strategies investors rarely understand
• How wealthy investors legally reduce taxes using real estate depreciation
• Why private equity, syndications, and commercial real estate dominate wealth building
• The difference between property value and projected investment income
• The financial strategies used by seven- and eight-figure investors
• Why relationships and proximity accelerate entrepreneurial growth

00:00 Introduction to the Legacy & Wealth Podcast
02:00 Ricardo’s background in finance and real estate
05:20 How Ricardo makes money through mortgage lending
08:30 Building a nationwide lending network
13:40 Lessons from working with real estate investors
20:10 The mindset difference between average earners and investors
27:00 Why relationships accelerate entrepreneurial success
35:20 Real estate as a wealth building vehicle
46:10 How investors use leverage to scale portfolios
58:00 The tax strategies used by high-income investors
1:11:00 How the ultra-wealthy reduce taxes legally
1:14:00 Real estate depreciation and investment structures
1:20:00 Lessons Ricardo learned through The Standard community

Follow Ricardo Carrillo on Instagram: https://www.instagram.com/richithelender/

Business leadership coach Nick Edwards reveals why most entrepreneurs fail to scale, the hidden cost of bad hires, and the framework he uses to turn struggling companies into high-performing organizations.

Nick Edwards is a leadership coach, speaker, and business consultant who works with executives and business owners to clarify vision, build stronger teams, and scale companies sustainably. Before entering the business world, Nick spent over two decades in ministry and also served as a Dallas police officer — experiences that shaped his approach to leadership, resilience, and human development.

In this episode, Nick shares the frameworks he uses to help companies grow from millions to tens of millions in revenue, why leadership isolation destroys high performers, and the simple system every entrepreneur should use to build a winning team.

He explains:

• Why business leaders often feel isolated at the top
• The “People + Systems = Results” framework for scaling companies
• How bad hires quietly destroy growing businesses
• Why personal life, leadership development, and business growth must stay aligned
• The leadership mistakes that keep companies stuck at the same level

00:00 Introduction to the Legacy & Wealth Podcast
02:30 Nick Edwards’ journey from ministry to business leadership coaching
06:00 The leadership lessons learned from decades in ministry
11:00 Why investing in men transforms families and communities
16:30 The isolation of leadership and why high performers struggle alone
20:30 Why business owners need people at their level to challenge them
25:00 Big Dreams, Small Steps — Nick’s framework for success
28:30 Why most entrepreneurs cannot define what they actually want
33:00 The leadership formula: People + Systems = Results
36:00 The most expensive mistake businesses make
40:00 How to identify the next step that actually grows your company
45:00 Why entrepreneurs overwhelm themselves and stop taking action
50:00 The real danger of private equity acquisitions
55:00 Scaling businesses without losing control

Follow Nick Edwards on LinkedIn: https://www.linkedin.com/in/nick-edwards-882490234/