What happens when the person asking the questions suddenly becomes the one being questioned?

In this episode of the Never Perfect Podcast, we flip the format and turn the microphone around. Instead of me interviewing someone from our team, Leandra takes over the host seat and puts me in the hot seat for a conversation that dives deeper into my life, leadership philosophy, entrepreneurship, parenting, sports, business, and the personal experiences that have shaped who I am today.

We start by going all the way back to childhood and discussing what I thought I wanted to be when I grew up. That leads into stories from my sports career, my dream of working in professional sports, and even a time when I was a finalist for a position with the Washington Redskins before entrepreneurship completely changed the trajectory of my life.

One of the most powerful parts of this conversation revolves around the coaches, mentors, and experiences that shaped me growing up. I share stories from youth sports, lessons from my father as both a parent and coach, and a defining moment during high school basketball that forever changed how I think about leadership, standing up for yourself, and doing the right thing even when it comes with consequences.

We also spend time talking about the relationship between parenting and entrepreneurship. As someone who spends every day building businesses, leading teams, and helping people grow, I've realized many of the same lessons apply to raising children. Patience, communication, self-awareness, accountability, and learning how different people process information all play a role whether you're leading employees or raising kids.

Leandra and I discuss leadership, personality assessments, personal development, and why understanding how people think is one of the most valuable skills anyone can develop. We talk about the importance of asking questions, creating environments where people can grow, and helping individuals find their highest and best use in both business and life.

The conversation takes a lighter turn with some unexpected questions, including whether I'd rather fight one kangaroo or one hundred squirrels, but even those moments lead back to discussions around decision-making, confidence, and how we approach challenges.

Toward the end of the episode, we dive into something that has been on my mind for years: launching the SteelPoint Foundation. I share why it took longer than it should have, the fears and excuses that delayed getting started, and why I finally decided it was time to stop waiting and start building something that could make a meaningful impact in our community.

We talk about the Foundation's mission, our first fundraising events, supporting organizations like Animal Friends and The Martha Fund, and why giving back has become such an important part of the long-term vision for everything we're building.

This episode is less about business tactics and more about the person behind the businesses. It's a conversation about growth, leadership, self-reflection, parenting, relationships, purpose, and the lessons that continue to shape my journey as an entrepreneur, father, and leader.

If you've ever wondered what drives my decisions, where my mindset comes from, or how the experiences of childhood, sports, business, and family continue to influence the way I lead today, this episode gives you a look behind the curtain.

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What separates the real estate investors who continue to grow from the ones who constantly complain that there are no deals left?

In this episode, I sit down with TJ to talk about what we're seeing every day inside our lending business and why so many investors are getting the market completely wrong. While social media is filled with people talking about rising interest rates, tighter margins, and a lack of opportunities, we're watching investors in our community have some of their best years ever.

This conversation is a behind-the-scenes look at private lending, real estate investing, relationship-based lending, deal analysis, and what it actually takes to continue winning in today's market.

We dive into how our approach at Local First Lending differs from traditional lenders. Most institutions rely on checkboxes, formulas, and underwriting matrices. We focus on the complete picture. The borrower, the deal, the contractor, the renovation plan, the experience level, and the overall likelihood of success. Real estate investing isn't one-size-fits-all, and neither is lending.

TJ shares how we evaluate opportunities beyond credit scores and why some investors who would be denied by traditional lenders can still be great borrowers when the right deal and team are in place. We also discuss what we're seeing in the Pittsburgh real estate market and why many investors continue finding opportunities despite increased competition and higher acquisition costs.

A major part of the conversation focuses on speed to lead and why quick action often determines who wins a deal. Whether it's off-market opportunities, wholesaler relationships, direct mail campaigns, or MLS properties, the investors who consistently perform are usually the ones who move first and make informed decisions quickly.

One of the most valuable stories in this episode involves a borrower working through only his second investment property. Instead of simply declining the deal, we worked alongside him to build a detailed renovation plan, scope of work, project milestones, and financing strategy that dramatically improved his chances of success. That example perfectly represents what relationship-based lending looks like when done the right way.

We also discuss private lending, hard money lending, BRRRR investing, wholesaling, reverse wholesaling, contractor management, renovation budgeting, project planning, rental property investing, and the importance of building long-term relationships in business.

Toward the end of the episode, TJ asks me when I'll buy my next investment property. We discuss managing nearly 900 units, balancing multiple businesses, and why I believe timing your life is far more important than timing the market.

If you're a real estate investor, entrepreneur, landlord, wholesaler, house flipper, or someone looking to build long-term wealth through real estate, this episode is packed with practical lessons that can help you make better decisions and execute at a higher level.

The biggest opportunities don't belong to the smartest investors. They belong to the investors who build strong relationships, move quickly, create clear plans, and consistently take action when others hesitate.

Casey's links:

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- Instagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA==

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TJ's links:

- Facebook: https://www.facebook.com/thomas.bencho

- Instagram: https://www.instagram.com/t.j.bencho/

- LinkedIn: https://www.linkedin.com/in/t-j-bencho-880661197/

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Learn more about me at caseyryanquinn.com

What happens when you are talented, hardworking, and still in the wrong seat? In this episode, I sit down with Julia, who has been with us for almost a year and has moved through more roles than most people would have stuck around for.

This conversation is one of the most honest and human episodes we have done because it is not about a win. It is about the messy, uncomfortable, real process of figuring out where someone actually belongs and what it takes to get there.

Julia came to SteelPoint from the corporate world after a life-altering experience. She lost her father unexpectedly, uprooted her life, and walked into a brand new environment that was faster, less structured, and more entrepreneurial than anything she had experienced before. She was hired as my personal brand manager and almost immediately knew something was not right. Instead of staying quiet and grinding through it, she did something most people never do. She knocked on my door and told me the truth.

That first conversation opened the door to everything that followed. We talk about what it actually feels like to show up every day and use all of your energy just to survive, let alone perform. Julia shares how she was suffering in silence, trying to fake it until she made it, until she realized that approach was failing her personally and professionally at the same time. The moment she started having honest conversations about where she was at, everything began to shift.

We unpack the difference between building a personal brand and building a business brand, and why managing someone else's personal brand is one of the hardest creative and psychological challenges there is. You have to know that person deeply, understand how they think, and be willing to make decisions on their behalf every single day. Julia explains why two months in was not enough time to do that with confidence, and why the pressure of not wanting to misrepresent who I am kept her stuck in analysis paralysis.

After moving through multiple roles across SteelPoint, Julia found her way to Revive Flooring and Paint, one of our portfolio companies, where she is now stepping into the integrator role. She talks about why having a single clear focus finally gave her the mental stability she needed, and why being able to connect with real customers every day brought her spark back. We also get into her predictive index profile as an altruist and why understanding that one thing helped clarify every role that did not fit before it.

The conversation goes deep into self-awareness, psychology in business, and why most people solve the nine surface problems created by one root problem instead of going after the real issue underneath all of it. Getting Julia into the right role was never about fixing her performance. It was about solving the real problem, which was that she was not doing work that fulfilled her.

We close with Julia turning the tables and asking me about hobbies. I talk about getting back into golf seriously, joining a local country club, committing to playing once a week, and my goal of getting to a single digit handicap within three years. I also come clean about already falling behind on my commitment to shoot basketball once a week, which is a pretty good reminder that accountability applies to everyone including me.

If you have ever felt talented but stuck, if you have ever wondered whether the role you are in is actually the right one, or if you lead people and want to understand how to get them to their highest and best use, this episode is exactly what you need to hear.

Casey's links:

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Revive Flooring and Paint' links:

- Website

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- Instagram

- LinkedIn

Join our Skool Community: https://www.skool.com/steelpointfoundry/aboutLearn more about me at caseyryanquinn.comWhat happens when people avoid the conversations they know they need to have?In this episode of the Never Perfect Podcast, TJ and I dive into one of the biggest problems holding people back in business, leadership, relationships, parenting, and personal growth: conflict avoidance. This conversation started organically and turned into one of the rawest discussions we’ve had around communication, accountability, emotional intelligence, leadership, and building genuine relationships.We talk about why most people avoid hard conversations, how unresolved conflict creates long-term damage, and why clarity almost always comes from addressing uncomfortable situations early instead of letting them build over time. Whether it’s inside a company, a marriage, parenting, investor relations, friendships, or leadership teams, avoiding difficult conversations rarely solves the problem. It usually makes it worse.A major part of this episode focuses on relationship building and investor relations. TJ shares what it’s like handling outreach, follow-ups, and raising capital through genuine relationships rather than transactional sales tactics. We discuss why follow-up is often harder than the initial outreach, why people avoid making decisions, and how emotional discomfort impacts communication in both business and life.We also dive into sales psychology, human behavior, and decision-making. One of the biggest themes throughout the conversation is that most people are not actually avoiding opportunities — they are avoiding making decisions. We break down how fear, uncertainty, ego, and discomfort influence the way people respond to conversations around investing, leadership, and personal growth.The conversation also explores EOS tools like the People Analyzer and how frameworks can help leaders navigate difficult conversations inside organizations without making those conversations personal or emotional. We explain how creating systems around accountability and communication can remove unnecessary drama while improving company culture and leadership alignment.Another major topic throughout the episode is parenting and emotional development. We share real stories about navigating tough conversations with our kids, teaching emotional control, building accountability, and preparing children to communicate directly instead of avoiding discomfort. These lessons connect directly back to entrepreneurship and leadership because the same principles apply everywhere: short-term discomfort often creates long-term growth.We also discuss the importance of direct communication in today’s world. Social media, texting, and digital communication have made it easier than ever for people to avoid real conversations. We talk about why picking up the phone or having face-to-face conversations still matters and why genuine human connection is becoming increasingly rare in business and life.Toward the end of the episode, we discuss leadership styles, closing deals, strategic relationship building, and the difference between being a salesperson versus being a problem solver and strategist. The conversation highlights how leadership is often less about controlling outcomes and more about understanding people, asking better questions, and helping others gain clarity around what they truly want.If you are an entrepreneur, investor, leader, salesperson, parent, or someone trying to improve your communication and relationships, this episode will challenge the way you think about conflict, leadership, accountability, and human connection.

What actually makes businesses grow long term?

It’s not just systems, strategy, or execution. It’s relationships, communication, and the willingness to have hard conversations before problems spiral out of control.

In this episode of the Never Perfect Podcast, I sit down with Leandra to break down one of the most overlooked leadership skills in business: conflict resolution and relationship building. We talk about why so many people avoid difficult conversations, how fear and ego quietly destroy opportunities, and why communication is the foundation of every successful company, partnership, and team.

This episode goes deep into company culture, leadership communication, emotional intelligence, people operations, and the importance of creating environments where people feel safe enough to speak honestly. We unpack how unresolved conflict creates resentment, damages performance, and slowly destroys relationships both personally and professionally.

We also talk about the reality of scaling businesses and leading teams. From hiring and firing employees to navigating partnerships, leadership decisions, and organizational growth, this conversation is a raw behind-the-scenes look at how human capital management actually works inside growing companies.

One of the biggest themes throughout this episode is understanding that communication solves problems earlier, faster, and more effectively than avoidance ever will. Whether it’s business partnerships, employees struggling in their roles, leadership tension, or personal relationships, the earlier the conversation happens, the easier the solution becomes.

Leandra shares her perspective from years of leading people operations and human resources, including lessons learned from toxic work environments, difficult managers, and what it means to truly put people first inside a company. We discuss why culture is not ping pong tables or office perks, but how people treat each other, communicate, and operate under pressure.

I also break down my philosophy on leadership, decision making, and why I’ve become obsessed with human capital management over real estate investing or scaling companies alone. We talk about intuition, asking better questions, and why the best leaders focus on understanding people before forcing solutions.

Throughout the conversation, we share real examples from inside our businesses, including role transitions, employee growth, conflict management, and how open communication helped team members find positions where they could truly thrive.

This episode is packed with practical leadership lessons, communication strategies, and mindset shifts for entrepreneurs, business owners, managers, and anyone trying to build stronger relationships in work and life.

If you’re building a company, managing people, leading teams, navigating partnerships, or simply trying to improve communication in your life, this episode will challenge the way you think about conflict, leadership, and relationships.

Casey's links:

- Facebook

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- LinkedIn

Join our Skool Community: https://www.skool.com/steelpointfoundry/about

Learn more about me at caseyryanquinn.com

What does it actually mean to build a business around a mission you truly believe in?

In this episode, we dive into the first of the six key components of EOS, the Entrepreneurial Operating System, and what it really means to lead with vision. This is not a textbook breakdown of the framework. This is a raw, honest conversation about how vision, mission, and core values show up in real life, inside real companies, and in the everyday decisions that define who you are as a leader, a founder, and a human being.

I open up about what our mission, to build happiness, transform lives, and strengthen the community, actually means beyond the words on the page. It is the lens I use for every decision I make in business and in life. Who I do business with, who I spend time with, what opportunities I say yes to, and what I walk away from even when there is serious money on the table. When your mission is real and not just something framed on a wall, it becomes a filter that protects your energy, your time, and your peace of mind.

TJ shares how the mission and vision of SteelPoint Capital pulled him away from running his own company six years ago. Not because the opportunity was perfect, but because the conviction behind what we were building was undeniable. At 42 years old, he says it plainly: he is the happiest he has ever been.

Danielle brings a fresh perspective as someone who recently stepped into a leadership role inside the organization. She walks through what drew her in during the interview process, how the core values aligned with the way she already lived her life, and why leading with mission and culture made her feel confident about the leap she was taking.

We break down all four of our core values. Let's Go means taking massive action every single day. Extreme Ownership means owning your results, your mistakes, and your growth without excuses. We Got Your Back is the team-first mentality that makes everything else possible. And Lead With Heart is about showing up with positivity, authenticity, and a genuine desire to lift the people around you.

The conversation also gets into what happens when you do not have clarity around your mission. I share a real example from a call with a founder running over three million dollars in annual revenue who could not articulate her mission or core values on the spot. That lack of clarity was showing up everywhere in her business.

The vision statement at SteelPoint Capital, to fuel people with capital, clarity, and culture to create an impact that lasts, is not just a tagline. It is the foundation everything is built on.

Whether you are a founder trying to get clear on your why, a leader building a team that actually believes in what you are doing, or someone figuring out what kind of life you want to build, this episode will challenge you to get honest about your mission and start making decisions that reflect it.

If you do not know your why, you will say yes to everything and end up building something you do not want to be inside of.

Casey's links:

- Facebook

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- LinkedIn

Danielle's links:

- Facebook

- Instagram

- LinkedIn

TJ's links:

- Facebook

- Instagram

- LinkedIn

Join our Skool Community here.

Learn more about me at www.caseyryanquinn.com

What happens when the person who hates social media becomes the face of a company?

In this episode, I sit down with my longtime friend and business partner Alex to unpack one of the most uncomfortable and necessary transitions we have made inside of Accruity.

Alex went from being completely invisible online, zero presence, no bio, a username nobody recognized, to becoming the face of our brand. What started as a conversation over beers at a Christmas party turned into a full shift in how we show up for our clients, our partners, and the people we are trying to reach.

We get into why personal branding is not about becoming an influencer. It is about building the know, like, and trust that makes a business real to the people considering working with you. If someone gets off a phone call with you and goes to look you up and finds nothing, you have already lost credibility before you even had the chance to earn it. That was the reality for Alex, and it was the moment that changed everything.

Alex walks through the real journey of stepping into this role.

Rebuilding his Instagram and Facebook from scratch with our marketing lead Rebecca.

Learning how to show up on camera, trust the process, and stop caring what people in his personal life thought about why he was suddenly posting about work.

The feedback, the doubts, the jokes from friends, all of it. And how getting even one client from a ten-like post is worth more than a thousand likes that convert to nothing.

We also talk about what it actually takes to get confident selling a complex service.

For Alex, that meant sitting in on fulfillment calls, watching our accounting team do the technical work, and immersing himself in the delivery side of the business until he could speak to it with authority. That combination of product knowledge and genuine client relationships is what has transformed him into someone who can walk into any room and represent what we do at the highest level.

A huge part of this episode is the role that Rebecca, our marketing lead based in Florida, has played in making all of this possible. She rebuilt Alex's entire digital presence, writes his scripts, designs the decks, and creates the content framework that keeps our messaging consistent from the ad someone sees to the call they book to the service they receive. She is a key reason our sales process has become one unified voice.

We wrap with a conversation about the next evolution, getting Alex on stage. Public speaking has always been my territory, but we are changing that. I share what my best and worst keynote experiences have taught me, why smaller rooms bring out my best work, and how I think about delivering value that people can actually act on when they leave.

If you are a business owner, a sales professional, or someone sitting on the fence about putting yourself out there, this episode is going to push you off that fence. The discomfort is real. The judgment from people around you is real. But the cost of staying invisible in a digital world is far greater than the cost of a bad post.

This episode is about doing the hard thing anyway, building trust at scale, and understanding that confidence comes from action, not from waiting until you feel ready.

Casey's links:

- Facebook

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- LinkedIn

Accruity Links:

- Website

- Facebook

- LinkedIn

- Instagram

Join our Skool Community here

Learn more about me at caseyryanquinn.com

Is artificial intelligence actually making us better… or just making life faster?

In this episode, we dive into one of the biggest conversations happening in business and society right now: the real impact of AI on entrepreneurs, leadership, relationships, and the future of human connection. This isn’t another surface-level discussion about new AI tools or tech hype. This is an honest conversation between founders actively building businesses while trying to figure out where artificial intelligence fits into the future of work and life.

We unpack how AI tools like ChatGPT and Claude are already transforming entrepreneurship, productivity, communication, content creation, project management, and business strategy. Danielle shares what she’s seeing inside mastermind groups where entrepreneurs are replacing traditional systems and entire workflows with AI-powered solutions. Small business owners can now build websites, create sales funnels, write marketing copy, organize projects, and launch campaigns faster than ever before.

But there’s another side to this conversation.

As more people rely on AI-generated content, businesses are beginning to sound the same. Marketing copy is becoming repetitive, websites look identical, and brands are losing the human personality that once separated great companies from average ones. We discuss why authenticity, communication, and real relationships may become the most valuable assets in business as artificial intelligence continues to grow.

TJ explains how he personally uses AI every single day as a tool to challenge his thinking, improve communication, navigate leadership decisions, and even think through parenting and marriage conversations. Rather than blindly trusting AI, he uses it as a sounding board to sharpen perspective and uncover blind spots. That distinction becomes one of the most important takeaways from the episode: AI should enhance critical thinking, not replace it.

The conversation also explores the darker side of artificial intelligence. We discuss concerns around deepfake videos, misinformation, younger generations becoming dependent on AI answers, and the possibility of people losing their ability to think independently. There’s a major difference between using AI as a tool and allowing it to become your source of truth.

We also talk about the economic impact of AI and how the workforce may evolve over the next decade. While many jobs and industries will inevitably change, we discuss why new opportunities will also emerge as technology advances. The bigger question becomes: what human skills will matter most in a world increasingly powered by automation?

One of the strongest themes throughout the episode is the importance of staying grounded in real human experiences. The conversation transitions into reflections from running the Pittsburgh Marathon and how doing difficult things in the physical world creates discipline, connection, and growth that technology can never replace. AI may help you build a training plan, but it cannot run the miles for you.

We discuss leadership, parenting, mindset, building relationship-driven businesses, and why surrounding yourself with the right people ultimately matters more than any piece of technology ever will. As AI continues to reshape business and society, this episode serves as a reminder that the future still belongs to people who can communicate, build trust, solve problems, and lead with authenticity.

If you’re an entrepreneur, founder, creator, business owner, or someone trying to navigate the future of artificial intelligence without losing the human side of life, this conversation will challenge the way you think about technology, leadership, relationships, and success.

Casey's links:

- Facebook

- Instagram

- LinkedIn

Danielle's links:

- Facebook

- Instagram

- LinkedIn

TJ's links:

- Facebook

- Instagram

- LinkedIn

What happens when you intentionally choose to do something hard?

In this episode, we unpack the mental, physical, and emotional lessons learned from running the Pittsburgh Marathon and Half Marathon. What started as a conversation about endurance quickly turned into a deeper discussion around mindset, resilience, entrepreneurship, leadership, communication, parenting, and adapting to change in business and life.

After completing his first full marathon, Casey reflects on how difficult experiences create perspective shifts that impact every area of life. TJ shares the brutal physical and mental battle that came during the final miles of the race and explains why pushing through discomfort creates a completely different level of confidence. Danielle joins the conversation after running a half marathon while 20 weeks pregnant, sharing what she learned about overcoming mental barriers, embracing uncertainty, and trusting herself in difficult moments.

The episode dives into the emotional highs and lows that happen during endurance challenges, including the mental battles, physical exhaustion, and unexpected struggles that come with pushing beyond your comfort zone. The group discusses how crowd energy, family support, and accountability from friends became fuel during the hardest parts of the race.

The conversation also highlights Brady McDonald’s extreme challenge of completing 50 straight 50Ks in 50 states over 50 days and how surrounding yourself with people pursuing ambitious goals can completely raise your own standards.

As the episode evolves, the focus shifts into entrepreneurship and leadership. Casey explains why communication is one of the most important skills in business and why fast-growing companies require constant adaptation, clarity, and alignment. Danielle shares lessons from transitioning into startup culture, where decisions, pivots, and changes happen rapidly compared to traditional corporate environments.

The team discusses how leadership requires understanding how different people communicate and why successful leaders adjust their communication style depending on the individual. The conversation also explores parenting, self-awareness, personal development, and the ongoing evolution required to continue growing in both business and life.

Another major topic throughout the episode is learning to focus only on what you can control. Casey breaks down the difference between stress and anxiety, explaining how many entrepreneurs waste energy trying to solve problems that do not exist yet instead of focusing on the present moment and actionable solutions.

The episode closes with a conversation about AI, rapid technological advancement, and how quickly the world is changing. In an environment where industries and careers are evolving faster than ever before, adaptability, communication, and resilience are becoming critical life skills.

This episode is ultimately about growth through discomfort. Whether you are building a business, training for a marathon, leading a team, raising a family, or simply trying to become mentally stronger, this conversation offers practical lessons on resilience, perspective, discipline, and embracing difficult experiences.

Casey's links:

- Facebook

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- LinkedIn

Danielle's links:

- Facebook

- Instagram

- LinkedIn

TJ's links:

- Facebook

- Instagram

- LinkedIn

What does it actually take to build wealth through real estate investing in today’s market and is the BRRRR strategy still worth it?

In this episode of the Never Perfect Podcast, I break down the real truth behind BRRRR investing and how it’s evolved from the early 2020s to today. If you’ve been hearing about building financial freedom through rental properties, stacking doors, and scaling a portfolio, this is the conversation that cuts through the noise and shows you what’s actually working right now.

I walk through the full BRRRR model; Buy, Renovate, Rent, Refinance, Repeat and explain how each step impacts your ability to create long-term wealth. More importantly, I share what most people get wrong, especially when it comes to underwriting deals, managing renovations, and navigating today’s higher interest rates and tighter margins.

This episode dives deep into real estate investing fundamentals like deal analysis, renovation execution, rental strategy, tenant quality, and financing options like DSCR loans. I also talk about why finding deals is harder than ever, how to think about risk on the buy side, and why most investors underestimate holding costs, contractor management, and the true impact of poor tenant decisions.

One of the biggest takeaways is understanding that while BRRRR investing can build massive wealth on paper, it doesn’t always create immediate cash flow. I share how I scaled close to 900 units using this model and why operating businesses became essential to generating real income alongside real estate.

If you’re a beginner trying to get your first deal or someone already in the game looking to sharpen your strategy, this episode gives you a practical, no-BS breakdown of how to approach BRRRR investing in today’s environment. From sourcing deals and building your team to structuring financing and repeating the process at scale, this is a real look at what it takes to succeed.

This is not theory. This is what’s happening inside real portfolios, real deals, and real markets.

Casey's links:

- Facebook

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- LinkedIn