Never Perfect

Casey Ryan Quinn
  • 5.0 (2)
  • Entrepreneurship
  • Updated Weekly

Are you an entrepreneur obsessed with scaling your business to the next level? Welcome to Never Perfect, the podcast for founders, innovators, and business leaders who are in the trenches, building and scaling their ventures. Hosted by serial entrepreneur Casey Ryan Quinn, this show cuts through the noise to deliver raw, unfiltered, and actionable strategies for exponential business growth. If you're ready to accelerate your growth, learn from those who have done it before, and embrace the "progress over perfection" philosophy, then this is the podcast for you. Subscribe to Never Perfect.

  1. 4d ago

    Most People Don't WANT To Solve Problems | What Ed Mylett Said That Made the Whole Room Cry

    ► Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/about What happens when you stop being the expert in the room and just become a student again? In this episode, TJ and I come back from a big week on the road and pull back the curtain on everything we experienced, learned, and brought home with us. We hit Grid Con in DC, spoke on two separate panels, and then came back for another quarter at the Boardroom Mastermind with Kent Clothier. This one is a real behind the scenes look at how we think about growth, relationships, conflict, and the mindset it takes to keep pushing when business gets complicated. We open with Grid Con, a real estate investment conference in DC that brought together agents, investors, and operators from around the country. I spoke on a panel both days, including a VIP only session at a winery outside the city. It is a community we are actively looking to bring to Pittsburgh and one worth paying attention to if you are in the real estate investment space. From there we get into the Boardroom and the Ed Mylett fireside chat with Kent Clothier that neither of us will forget anytime soon. This was not a keynote. It was just Ed and Kent sitting in chairs talking honestly. Ed went deep into religion, peace, and what he has found over the last six years that has changed the way he moves through the world. He pushed Kent in a way that very few people ever have, and watching that unfold in real time was one of the more powerful things I have seen on a stage. TJ shares the story that hit him hardest from Ed's fireside chat. Ed described watching a woman at the airport walk past him dozens of times during a long delay and then narrating in his mind the full arc of her life. The dreams she had as a girl. The family she built. The quiet disappointments along the way. And how most people walking through that airport never once noticed her. Ed made a decision to notice. That story rippled through the entire room and the next day someone at the reception broke down in tears because a fellow attendee stopped to genuinely thank the person cutting meat at the buffet. That is the kind of impact great storytelling has when it comes from someone who actually means what they say. We also get into the best business takeaway from the two days, which TJ and I both landed on independently. Simplify. When you are growing fast it is easy to keep adding steps, adding processes, and adding complexity until nothing moves cleanly anymore. The answer is almost always to get back to the KPIs that matter, get the right people in the right seats, and stop making things harder than they need to be. I get honest about something I do not always admit. I still avoid conflict even though I preach against it. The three biggest problems I have had to solve recently all came from me ignoring something earlier than I should have. That is the pattern. Small avoidances compound into big problems and the only solution is to have the conversation earlier than feels comfortable. TJ asks me why I come alive in hot seat settings at the boardroom, and the answer gets into who I am at my core. I feel obligated to say the thing other people will not say. I will stand up for what I believe in even if it costs me a relationship. That has created conflict over the years and it has also created some of the best outcomes I have ever been a part of. Learning when to push and when to pull back is the lifelong work. We close with TJ celebrating four straight Boardroom MVP awards, five out of the last seven, and why getting around like-minded people who want to be better is one of the highest leverage things any business owner can do with their time.

    42 min

  2. 6d ago

    David Alan: From Selling Suits Out of His Car to Celebrity Stylist & Premium Brand Builder

    Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/about What does it take to build a premium brand, scale a business, embrace AI, and maintain the mindset required to keep growing when success finally arrives? In this episode of the Never Perfect Podcast, I sit down with my longtime friend and entrepreneur David Alan, founder of David Alan Clothing. Over the last decade, I've had a front-row seat watching David grow from selling suits out of his vehicle to building one of the most recognized luxury custom clothing brands in the country. Today, he works with business owners, executives, professional athletes, celebrities, and high performers while continuing to expand his business into new markets. We dive deep into what growth actually looks like behind the scenes and why building the right team remains one of the hardest challenges for any entrepreneur. David shares how finding people who truly believe in the mission, care about the customer experience, and want to help build something bigger than themselves has become one of the biggest factors in scaling his company. We discuss leadership, culture, accountability, hiring, and what separates average employees from people who become true partners in growth. A major part of our conversation focuses on artificial intelligence and how David is implementing AI throughout his business. From AI-powered lead qualification and appointment booking to voice-based AI agents capable of having real conversations with potential customers, we explore how technology is changing sales, marketing, customer service, and business operations. We also discuss the opportunities, concerns, and realities of integrating AI while maintaining a premium customer experience. We also talk extensively about personal branding, professional image, confidence, and why appearance matters more than most people realize. David explains how clothing impacts confidence, perception, business opportunities, and personal performance. We discuss the psychology behind presentation, why successful people often invest in themselves differently, and how confidence can be built through small intentional decisions. The conversation eventually shifts into entrepreneurship, mindset, resilience, and the realities of building a company through uncertainty. We discuss economic conditions, consumer behavior, leadership during difficult times, and what it takes to continue growing when obstacles keep showing up. David shares lessons from his entrepreneurial journey, while I discuss how getting fired years ago became one of the most important catalysts for my own growth and why consistency ultimately matters more than motivation. This episode is packed with practical lessons on business growth, leadership, company culture, AI implementation, sales, marketing, personal development, confidence, entrepreneurship, and the habits that separate people who keep moving forward from those who quit when things get hard. If you're building a business, leading a team, developing your personal brand, exploring AI, or simply trying to become a better version of yourself, this conversation offers a real and honest look at what growth actually requires. 🔗 RESOURCES & LINKS ► Learn more about me at www.caseyryanquinn.com ► Subscribe to the Never Perfect Podcast: https://www.youtube.com/@caseyryanquinn ►Casey's links: - Facebook: https://www.facebook.com/share/1TwCw8ewFf/?mibextid=wwXIfr - Instagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA== - LinkedIn: https://www.linkedin.com/in/caseyryanquinn

    33 min

  3. Jun 6

    From Rebel Athlete to Relentless Founder: The Moments That Changed His Life

    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. 🔗 RESOURCES & LINKS ► Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/about ► Learn more about me at www.caseyryanquinn.com ► Subscribe to the Never Perfect Podcast: https://www.youtube.com/@caseyryanquinn ►Casey's links: - Facebook: https://www.facebook.com/share/1TwCw8ewFf/?mibextid=wwXIfr - Instagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA== - LinkedIn: https://www.linkedin.com/in/caseyryanquinn

    33 min

  4. Jun 4

    Stop Checking Boxes | The Smarter Way to Lend and Borrow for Real Estate Investing

    🔗 RESOURCES & LINKS ► Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/about ► Learn more about me at www.caseyryanquinn.com ► Subscribe to the Never Perfect Podcast: https://www.youtube.com/@caseyryanquinn 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: - Facebook: https://www.facebook.com/share/1TwCw8ewFf/?mibextid=wwXIfr - Instagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA== - LinkedIn: https://www.linkedin.com/in/caseyryanquinn 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/

    35 min

  5. May 29

    From Corporate America to Integrator | What Self-Awareness and Hard Conversations Actually Builds

    Join our FREE Skool Community HERE 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: - Facebook - Instagram - LinkedIn Revive Flooring and Paint' links: - Website - Facebook - Instagram - LinkedIn

    39 min

  6. May 24

    One Conversation Could Have Saved Years | The Real Cost of Avoiding Conflict

    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.

    37 min

  7. May 21

    This one of the most overlooked leadership skills in business....

    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 - Instagram - LinkedIn

    33 min

  8. May 16

    You'll Never Have Success Without A Vision I EOS Component 1: Vision

    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 - Instagram - LinkedIn Danielle's links: - Facebook - Instagram - LinkedIn TJ's links: - Facebook - Instagram - LinkedIn

    29 min
See All (31)

Ratings & Reviews

5
out of 5
2 Ratings

About

Are you an entrepreneur obsessed with scaling your business to the next level? Welcome to Never Perfect, the podcast for founders, innovators, and business leaders who are in the trenches, building and scaling their ventures. Hosted by serial entrepreneur Casey Ryan Quinn, this show cuts through the noise to deliver raw, unfiltered, and actionable strategies for exponential business growth. If you're ready to accelerate your growth, learn from those who have done it before, and embrace the "progress over perfection" philosophy, then this is the podcast for you. Subscribe to Never Perfect.

Information

  • Creator
    Casey Ryan Quinn
  • Years Active
    2K
  • Episodes
    31
  • Rating
    Explicit
  • Copyright
    © Casey Ryan Quinn
  • Show Website
    Never Perfect