Social 333 Podcast - Chris D. Bentley

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The Love You More Strategy: The Counterintuitive Truth | Toye Penny #social333podcast #155 Aug 06, 2026

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The Love You More Strategy: The Counterintuitive Truth | Toye Penny #social333podcast #155

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Toye Penny to discuss the counterintuitive idea behind the Love You More Strategy—why taking better care of yourself can actually make you a stronger leader, parent, entrepreneur, and partner.

Toye is the creator of The Love You More Method™ and founder of Love You More International™, where her work centers on helping high-performing mothers and leaders move away from overwhelm, silent pressure, and constant self-sacrifice toward greater self-mastery, well-being, and sustainable leadership.

The conversation explores why constantly putting everyone else first can eventually damage your own performance and the people who depend on you. Instead of viewing self-care as selfish, Toye explains why protecting your mental, emotional, physical, and spiritual well-being creates the capacity to lead and support others more effectively.

They also explore burnout, identity, motherhood, leadership pressure, emotional resilience, healthy boundaries, and why looking successful on the outside does not necessarily mean someone is doing well internally.

Whether you are an entrepreneur, executive, parent, or leader carrying more responsibility than most people realize, this conversation challenges the belief that sacrificing yourself is the price of success.

✅ Why loving yourself more is not selfish

✅ The hidden cost of constantly putting others first

✅ How self-sacrifice eventually leads to burnout

✅ Why successful leaders can still struggle internally

✅ Creating boundaries without feeling guilty

✅ Self-mastery as a foundation for stronger leadership

✅ Balancing leadership, family, and personal well-being

✅ Why your behavior becomes a blueprint for others

✅ Building emotional resilience under pressure

✅ Creating success that is actually sustainable

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Toye Penny

00:54 – Women, leadership, and funding challenges

02:30 – Adversity and finding answers within

04:46 – Learning resilience through failure

09:18 – Trauma, motivation, and leadership

15:58 – Leading by example

19:30 – Why leaders need real presence

22:36 – The hidden weight of leadership

24:31 – Focus, distraction, and loneliness

29:02 – Public success, private struggles

35:03 – Healing trauma and breaking patterns

35:35 – Rooted in the Kitchen

37:12 – Community, vulnerability, and shared experiences

41:38 – Final thoughts and where to connect with Toye

🎧 Subscribe for more conversations about entrepreneurship, leadership, personal growth, well-being, and building sustainable success.

📣 Share this episode with a leader, entrepreneur, or parent who spends so much time taking care of everyone else that they forget to take care of themselves.

Why Fame Doesn't Guarantee Business Success | Tarra Stubbins #social333podcast #154 Aug 05, 2026

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Why Fame Doesn't Guarantee Business Success | Tarra Stubbins #social333podcast #154

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Tarra Stubbins to discuss why fame, followers, attention, and public recognition do not automatically translate into a successful business.

After spending years working behind the scenes with internationally recognized musicians and entertainers, Tarra gained a firsthand look at the discipline, structure, focus, and support systems required to maintain success at the highest level. She later applied those lessons to entrepreneurship, helping executives and creative leaders manage their time, operations, and growing responsibilities.

This conversation explores the difference between looking successful and building something sustainable. Tarra explains why visibility can create opportunities, but it cannot replace strong leadership, financial discipline, effective systems, reliable teams, or a business model that genuinely works.

They also discuss celebrity culture, productivity, delegation, personal branding, scaling, and why many talented people struggle when they suddenly become responsible for running an actual company. Whether you are a creator, entrepreneur, executive, or personal brand, this episode offers an important reminder that attention may open the door—but business fundamentals determine whether you stay in the room.

✅ Why fame does not guarantee business success

✅ The difference between popularity and profitability

✅ What Tarra learned from working with major entertainers

✅ Why successful people protect their time and focus

✅ Turning creative talent into a structured business

✅ How delegation supports sustainable growth

✅ Why followers and visibility can create false confidence

✅ The operational challenges behind personal brands

✅ Building the right team around a growing leader

✅ Why discipline and consistency matter more than status

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Tarra Stubbins

01:02 – Working with Jagger, Drake, and Branson

05:03 – Supporting celebrities behind the scenes

06:08 – Meeting Richard Branson

07:32 – Delegation, trust, and productivity

09:26 – Hiring challenges and high standards

11:20 – AI’s impact on recruiting

12:39 – How the music industry chooses talent

16:08 – Why fame is rented

18:05 – Building and protecting your public brand

19:11 – Fake profiles, AI, and online scams

24:28 – The hidden sacrifices of entrepreneurship

27:06 – Cash-flow struggles behind business success

30:26 – Final thoughts and where to connect with Tarra

🎧 Subscribe for more conversations about entrepreneurship, leadership, productivity, personal branding, and building sustainable businesses.

📣 Share this episode with an entrepreneur or creator who needs to hear that being well-known and building a successful company are two very different things.

Generous Listening vs Active Listening | Jenn Farrer #social333podcast #153 Jul 31, 2026

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Generous Listening vs Active Listening | Jenn Farrer #social333podcast #153

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Jenn Farrer to discuss the difference between active listening and generous listening—and why appearing to listen is not the same as creating a conversation where someone feels genuinely understood. Jenn explains how leaders, managers, coaches, and entrepreneurs often enter conversations ready to solve problems, offer advice, or prepare their next response. Although those intentions may be positive, they can prevent the other person from thinking clearly, expressing what is really happening, and taking ownership of the solution.

The conversation explores how generous listening creates more space for curiosity, reflection, trust, and meaningful insight. Jenn also discusses the importance of listening beneath someone’s words, recognizing when defensiveness is affecting a conversation, and asking questions that help people discover their own answers. Whether you lead a team, coach others, manage employees, or simply want to improve your personal relationships, this episode offers practical lessons for creating more honest, productive, and transformative conversations.

✅ The difference between active and generous listening

✅ Why listening techniques alone are not enough

✅ How advice-giving can prevent independent thinking

✅ Listening to understand instead of preparing a response

✅ Why curiosity creates stronger conversations

✅ Recognizing defensiveness and psychological threat

✅ Asking questions that create insight and ownership

✅ Listening beneath the surface of someone’s words

✅ Helping people develop their own solutions

✅ Using generous listening in leadership and relationships

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Jenn Farrer

01:23 – A life-changing experience in the ICU

05:21 – Recognizing when people genuinely care

08:06 – Underdog stories, faith, and coaching

14:06 – Dropping the ego and choosing discovery

18:45 – Working backward to solve problems

21:47 – Business coaching and the price of growth

25:30 – The hidden sacrifices behind success

28:37 – Avoiding distractions and learning to say no

31:37 – Disconnecting from technology in the ICU

33:00 – Listening beyond words and watching actions

36:08 – Generous listening in sales and coaching

39:49 – Final thoughts and where to connect with Jenn

🎧 Subscribe for more conversations about entrepreneurship, leadership, communication, coaching, and building stronger professional relationships.

📣 Share this episode with a leader, manager, coach, or entrepreneur who wants to communicate more effectively and help others think for themselves.

The Cybersecurity Breach Tsunami Will Destroy Many Companies | Craig Taylor #social333podcast #152 Jul 30, 2026

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The Cybersecurity Breach Tsunami Will Destroy Many Companies | Craig Taylor #social333podcast #152

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Craig Taylor to discuss the growing wave of cybersecurity breaches and why many companies remain dangerously unprepared for what is coming. Cybercriminals are becoming faster, more convincing, and more effective. At the same time, many businesses still rely on outdated policies, annual training sessions, weak passwords, and the assumption that their employees will recognize every threat. Craig explains why technology alone cannot protect an organization when human behavior remains one of its biggest vulnerabilities.

This conversation explores phishing, social engineering, artificial intelligence, employee education, security culture, and the financial consequences of a serious breach. Craig also explains why fear-based training can backfire, how positive reinforcement creates stronger security habits, and what business leaders should prioritize before an attack occurs.

Whether you run a small business, lead a growing company, manage employees, or handle sensitive customer information, this episode offers practical insight into reducing cybersecurity risk before one mistake becomes a company-ending crisis.

✅ Why cybersecurity breaches are increasing

✅ How human behavior creates security vulnerabilities

✅ The growing danger of phishing and social engineering

✅ How AI makes cyberattacks more convincing

✅ Why traditional cybersecurity training often fails

✅ The problem with punishing employees who make mistakes

✅ Using positive reinforcement to improve security habits

✅ Passwords, multifactor authentication, and cyber literacy

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Craig Taylor

00:54 – Fake Zoom links and phishing scams

02:58 – AI-generated podcast outreach scams

06:13 – How AI is changing cybersecurity

08:42 – Romance scams targeting older adults

10:20 – Identity theft and money mule schemes

13:00 – Understanding the breach tsunami

20:20 – Why cybercriminals create attacks

21:48 – Extortion emails and stolen information

24:48 – Banking and real estate wire fraud

27:00 – Exposing a fraudulent property closing

28:50 – The rising cost of cyber insurance

30:43 – Final thoughts and where to connect with Craig

🎧 Subscribe for more conversations about entrepreneurship, leadership, technology, cybersecurity, and protecting modern businesses.

📣 Share this episode with a business owner or company leader who believes a cybersecurity breach could never happen to them.

Don't Make This Scaling Mistake With Your Payroll | Paul Swainey #social333podcast #151 Jul 29, 2026

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Don't Make This Scaling Mistake With Your Payroll | Paul Swainey #social333podcast #151

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Paul Swainey to discuss one of the most dangerous mistakes business owners make while scaling: increasing payroll before the company has the revenue, systems, and cash flow to support it.

Hiring more people can feel like progress, but every new employee creates additional financial and operational responsibilities. Paul explains why founders must look beyond salaries and consider taxes, benefits, insurance, onboarding, management time, equipment, compliance, and the true cost of maintaining a growing team.

This conversation explores payroll planning, hiring decisions, cash-flow management, delegation, leadership, and the pressure entrepreneurs face when their team grows faster than the business. They also discuss why hiring too early can reduce profitability, create unnecessary complexity, and leave founders struggling to make payroll during slower months.

✅ Why increasing payroll does not always equal growth

✅ The hidden costs associated with every new hire

✅ Hiring based on proven demand instead of expectations

✅ How payroll can damage cash flow during slower periods

✅ Knowing when your business is financially ready to expand

✅ Employees, contractors, and different staffing options

✅ Building systems before adding more people

✅ Protecting profitability while scaling your company

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Paul Swainey

00:54 – Why operations matter when scaling

01:47 – Operations versus private equity

02:44 – Building systems before hiring

05:57 – The difficult 5-to-13 employee stage

06:39 – Scaling beyond 20 team members

08:25 – Creating momentum through team growth

10:00 – Restructuring the operating model

16:59 – Paul’s podcast and its mission

18:33 – Persistence, rejection, and high-value sales

20:30 – The daily reality of entrepreneurship

22:19 – Final thoughts and where to connect with Paul

🎧 Subscribe for more conversations about entrepreneurship, leadership, business operations, hiring, and sustainable growth.

📣 Share this episode with a founder or business owner who is growing a team and needs to understand the real financial impact of payroll.

The Mad Men Mistake That Ruined Advertising | Andrew Stadelberger #social333podcast #150 Jul 24, 2026

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The Mad Men Mistake That Ruined Advertising | Andrew Stadelberger #social333podcast #150

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Andrew Stadelberger to discuss the outdated advertising mindset that continues to hurt agencies, brands, and business owners today.

For years, the advertising industry celebrated the “Mad Men” model—big personalities, expensive offices, flashy creative ideas, and campaigns designed to generate attention. But modern businesses need more than exposure. They need strategy, trust, consistency, measurable outcomes, and an agency that understands how advertising connects to actual business growth.

Andrew breaks down how advertising agencies really operate, why great marketing takes longer than most clients expect, and how chasing quick wins can damage both the campaign and the client-agency relationship. The conversation also explores agency economics, fractional teams, artificial intelligence, client expectations, and the difference between simply being visible and becoming valuable.

Whether you are a business owner hiring an agency, a marketer building campaigns, or an entrepreneur growing a creative company, this episode offers an honest look at what effective advertising requires today.

✅ The outdated “Mad Men” mindset affecting advertising

✅ Why flashy creative does not guarantee business results

✅ The difference between exposure and genuine value

✅ How advertising agencies actually make money

✅ Why effective marketing requires patience and consistency

✅ Building stronger relationships between agencies and clients

✅ Fractional teams versus traditional agency structures

✅ How AI is changing advertising and communication

✅ Setting realistic expectations for campaigns

✅ What serious businesses should expect from an agency

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Andrew Stadelberger

01:00 – How Player Coach works with brands

02:37 – PR services and brand visibility

03:02 – The problem with fractional leadership

05:08 – Why PR requires long-term commitment

09:45 – Fame versus strategic positioning

11:22 – The reality behind viral marketing

14:25 – The trust recession and attention economy

17:25 – Why authenticity builds stronger brands

19:03 – Being honest about business struggles

19:55 – Why an easy life becomes unfulfilling

21:47 – Final thoughts and where to connect with Andrew

🎧 Subscribe for more conversations about entrepreneurship, advertising, leadership, marketing, and building sustainable businesses.

📣 Share this episode with a business owner, marketer, or agency leader who wants to understand what effective advertising actually looks like today.

The Real Founders Path Looks Nothing Like You Think | Seva Ustinov #social333podcast #149 Jul 23, 2026

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The Real Founders Path Looks Nothing Like You Think | Seva Ustinov #social333podcast #149

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Seva Ustinov to discuss what the founder’s journey actually looks like behind the polished success stories, funding announcements, and business headlines.

Seva shares lessons from more than two decades of entrepreneurship, including building a marketing agency, scaling technology companies, rebuilding when the original model no longer worked, and creating AI-powered systems for modern performance marketing teams. His journey includes moving from Russia to the United States, developing an AI-first company, and raising millions in funding while competing in a crowded technology market.

This conversation explores the uncertainty, pivots, operational problems, team challenges, and difficult decisions that rarely appear in the public version of entrepreneurship. Seva explains why founders must become comfortable with rebuilding, learning new skills, changing direction, and creating systems that allow a company to grow beyond their personal capacity.

✅ Why the founder’s path is rarely predictable

✅ Building a company through uncertainty and constant change

✅ Knowing when your original business model must evolve

✅ Lessons from rebuilding a company from the ground up

✅ Raising capital in a crowded AI market

✅ Creating systems that reduce operational chaos

✅ Using AI to improve onboarding, workflows, and team productivity

✅ Why resilience and adaptability matter more than perfect planning

00:00 – Intro

00:06 – Meet Seva Ustinov

00:47 – What Drives an Entrepreneurial Pivot?

02:36 – Making a Systemic Change in Business

04:45 – How Seva Built a Team of 100 Employees

07:54 – The Biggest Challenges of Scaling

09:27 – Managing IT Emergencies and Pressure

11:43 – Hiring, Firing, and Employee Distractions

13:12 – Building AI Trading Bots as a Creative Outlet

18:08 – Creating Products for Existing Demand

22:55 – Why Success Takes Longer Than Expected

25:00 – Looking Back at 10 Years of Growth

27:16 – Building an Algorithmic Trading Bot With AI

30:33 – Final Thoughts and Where to Connect With Seva

🎧 Subscribe for more conversations about entrepreneurship, leadership, artificial intelligence, business growth, and the realities of building companies.

📣 Share this episode with a founder or entrepreneur who needs the reminder that the real path to success is rarely straight, predictable, or comfortable.

Food Trucks vs Restaurants: What They Won't Admit | Tim Tobitsch #social333podcast #148 Jul 17, 2026

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Food Trucks vs Restaurants: What They Won't Admit | Tim Tobitsch #social333podcast #148

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Tim Tobitsch to discuss the realities of operating food trucks and traditional restaurants—and why neither business model is as simple or inexpensive as it may appear.

Drawing from experience across both brick-and-mortar restaurants and mobile food operations, Tim explains the major differences in startup costs, staffing, permits, maintenance, customer acquisition, daily operations, and profitability. He also breaks down the assumptions aspiring food entrepreneurs often make before entering the industry.

This conversation explores what it takes to build a sustainable food business, the challenges operators rarely discuss publicly, and why buying a food truck does not automatically create freedom or reduce risk. Tim also shares practical lessons for entrepreneurs deciding whether to launch a truck, open a restaurant, expand into multiple locations, or avoid the industry entirely.

✅ The real differences between food trucks and restaurants

✅ Why food trucks are not always the cheaper option

✅ Startup expenses aspiring operators underestimate

✅ Permits, maintenance, staffing, and daily operations

✅ How weather and location affect food truck revenue

✅ The challenges of moving from a truck to a restaurant

✅ What makes a food concept sustainable and profitable

✅ Common mistakes new food entrepreneurs should avoid

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Tim Tobitsch

01:35 – Starting a restaurant at 24

03:58 – Scaling restaurants and food trucks

09:50 – Franchises, staffing, and daily operations

14:41 – Food trucks as event attractions

15:57 – Winning with a unique food concept

19:56 – Using food trucks to market restaurants

22:13 – Final thoughts and where to connect with Tim

🎧 Subscribe for more conversations about entrepreneurship, leadership, small business, hospitality, and building sustainable companies.

📣 Share this episode with someone considering opening a restaurant, launching a food truck, or investing in the food and beverage industry.

Trauma Isn't Your Fault But Staying Comfortable Is | Darius Ross #social333podcast #147 Jul 17, 2026

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Trauma Isn't Your Fault But Staying Comfortable Is | Darius Ross #social333podcast #147

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Darius Ross for an honest conversation about trauma, personal responsibility, healing, and the danger of remaining comfortable in patterns that no longer serve you.

Darius explains that the painful experiences people endure are not always their fault, but eventually they must decide whether those experiences will continue controlling their future. They explore how trauma can influence relationships, confidence, decision-making, identity, and the willingness to pursue a better life.

This conversation dives into accountability, resilience, entrepreneurship, emotional healing, and the uncomfortable work required to break destructive cycles. Whether you are recovering from a difficult childhood, relationship, failure, or major life setback, this episode offers a powerful perspective on moving beyond survival and choosing growth.

✅ Why trauma is not always your fault

✅ How comfort can keep people trapped in unhealthy patterns

✅ The difference between understanding your past and living in it

✅ Taking responsibility without blaming yourself

✅ Why healing requires uncomfortable decisions

✅ Breaking cycles that affect relationships and success

✅ Turning painful experiences into strength and purpose

✅ Building resilience after setbacks and adversity

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Darius Ross

00:29 – Introducing the TPS Blueprint

00:41 – Inside Darius Ross’s book

02:54 – Overcoming childhood adversity

04:05 – Therapy, trauma, and support systems

07:13 – Practical steps beyond therapy

10:25 – Living with post-traumatic stress

12:56 – Faith, surrender, and healing

14:11 – Gratitude through difficult seasons

16:16 – Accepting blessings after trauma

22:20 – Deciding when enough is enough

25:00 – Attraction to unhealthy patterns

26:45 – Raising relationship standards

28:23 – The Gorilla Principles

29:40 – Fighting battles you cannot win

31:25 – Final thoughts and where to connect with Darius

🎧 Subscribe for more conversations about entrepreneurship, leadership, mental health, personal growth, and overcoming adversity.

📣 Share this episode with someone who needs the reminder that their past may explain their struggles, but it does not have to determine their future.

Your Biggest Problem? Your Surroundings | Bridgette Bello #social333podcast #146 Jul 17, 2026

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Your Biggest Problem? Your Surroundings | Bridgette Bello #social333podcast #146

In this episode of the Social 333 Podcast, host Chris D. Bentley sits down with Bridgette Bello to discuss how your surroundings can become either your greatest advantage or the biggest obstacle standing between you and success.

Bridgette shares insights on leadership, personal growth, relationships, and the importance of becoming intentional about the people, environments, and conversations you allow into your life. They explore how negative influences can quietly affect your confidence, decision-making, ambition, and ability to move forward.

This conversation also examines entrepreneurship, building the right network, leaving environments that no longer support your growth, and why surrounding yourself with driven, honest, and supportive people can change the direction of your life and business..

✅ How your surroundings influence your mindset and results

✅ Recognizing people and environments that hold you back

✅ Why successful people become intentional about relationships

✅ Building a stronger professional and personal network

✅ The connection between leadership, confidence, and community

✅ Knowing when you have outgrown your current environment

✅ Protecting your energy while pursuing ambitious goals

✅ Creating surroundings that support long-term growth

📌 CHAPTERS

00:00 – Intro

00:06 – Meet Bridgette Bello

01:27 – Networking and meaningful connections

01:53 – High-level peer groups

03:02 – Finding the right leadership community

03:34 – Structured networking for executives

04:53 – Privacy in exclusive business circles

06:45 – Protecting time and setting entry standards

09:41 – The CEO isolation tax

11:20 – Leadership pressure and business succession

14:32 – Founder identity after an exit

18:05 – Women in leadership and access to capital

25:25 – Why strong employees change over time

27:06 – Rebuilding teams when people get stuck

27:48 – Final thoughts and where to connect with Bridgette

🎧 Subscribe for more conversations about entrepreneurship, leadership, mindset, relationships, and personal development.

📣 Share this episode with someone who may need to reconsider the people, habits, or environments influencing their future.

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