Never Perfect

Casey Ryan Quinn

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. 4 days ago

    The Operations Playbook: How We Run & Optimize a Scaling Business

    ► Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/aboutWhat does it actually take to run day-to-day operations at a fast-growing company? In this episode, I sit down with Jil, Director of Operations at SteelPoint Capital, to break down how she manages operations across the parent company and its subsidiaries; and how the Entrepreneurial Operating System (EOS) keeps everything moving without too much chaos.Jil shares how a "fast-paced" culture isn't about rushing decisions, but about making clear, scalable decisions quickly and executing with confidence. We dig into how EOS creates accountability through quarterly planning, weekly check-ins, and a simple but powerful "issues list" system that turns roadblocks into solutions instead of excuses.WHAT YOU'LL LEARN: ►What to do with your current spreadsheets and how centralized systems can create a single source of truth for reporting, forecasting, and sales.►How to effectively use AI-integrated tools to automate manual tasks and free up your team's time.►How to prioritize and time-block to stay focused amid competing demands.►How to build trust as a new leader by showing teams how automation helps them grow, not replace them.►How to live in the EOS system and stay accountable.Whether you're a founder, operations leader, or just trying to bring more structure to a scaling business, this conversation is packed with practical takeaways on clarity, accountability, and building systems that scale.ABOUT MEI'm Casey Quinn, entrepreneur, investor, and founder of SteelPoint. Through acquisitions, partnerships, and operational leadership, I help founder-led businesses scale through accountability, strategy, leadership development, and long-term value creation.Subscribe for more conversations on entrepreneurship, leadership, personal growth, communication, accountability, investing, and building businesses that create lasting impact.🔗 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=wwXIfrInstagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA==LinkedIn: https://www.linkedin.com/in/caseyryanquinn

  2. 24 Jul

    How Our Charity Gala Delivered for Business & Community I Impact Is EVERYTHING!

    What an incredible night! This year's Charity Gala for Animal Friends and The Martha Fund brought together generous supporters, dedicated volunteers, and our incredible investors for an unforgettable evening of giving back. I talk with TJ Bencho to recap the night, and look at what's ahead for Steelpoint Foundation.From a delicious dinner with a crunchy crust on the steak to heartfelt stories of the impact our donations will make, this event exceeded every expectation; even when the unexpected happened. Midway through the night, we faced a full power outage, but thanks to the quick thinking and teamwork of our staff, volunteers, and guests, the show went on without missing a beat. Moments like these remind us what community and resilience truly look like.We are beyond grateful for the opportunity to host an event like this. All of the work will directly support the work of Animal Friends and The Martha Fund. Every ticket, donation, and auctioned off item in that room helps provide love to every animal that Animal Friends sees, and A new playground thanks to the Martha Fund.Thank you to our sponsors, donors, and every guest who showed up and gave generously. This gala wouldn't be possible without YOU.WHAT YOU'LL LEARN:✔ How to make the most of unexpected issues that pop up during an event✔ Why doing something bigger than yourself is important✔ How to look at past events to see how you can improve✔ Why impact is everything✔ How helping give back to the community you're apart of is good for everyone► Want to learn more about what we do at Steelpoint Foundation? get information here: https://steelpointfoundation.orgABOUT MEI'm Casey Quinn, entrepreneur, investor, and founder of SteelPoint. Through acquisitions, partnerships, and operational leadership, I help founder-led businesses scale through accountability, strategy, leadership development, and long-term value creation.ABOUT TJ BENCHOTJ Bencho is a business leader, entrepreneur, and leadership coach focused on helping people build stronger relationships, develop accountability, and live with greater purpose.Subscribe for more conversations on entrepreneurship, leadership, personal growth, communication, accountability, investing, and building businesses that create lasting impact.🔗 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=wwXIfrInstagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA==LinkedIn: https://www.linkedin.com/in/caseyryanquinn► TJ's links:Facebook: https://www.facebook.com/thomas.benchoInstagram: https://www.instagram.com/t.j.bencho/LinkedIn: https://www.linkedin.com/in/t-j-bencho-880661197/

  3. 17 Jul

    Your Mastermind Guide: What to Expect and How to Get The Most Out of The Event

    ► Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/aboutAre you investing time and money into a business mastermind but questioning the actual return on investment? Maybe you're just curious how to actually get something out of them. Or maybe you're noticing the same things we notice: people paying for friendship and getting nothing valuable from the minds in the room with them. In this episode, Alex Orosz and I break down the reality of being in these business masterminds groups; from their true purpose to the metrics you should be tracking to measure success.It’s time to get smart about being at these events; we want to make sure you are getting the most out of events like Investor Fuel. So we're here to help you evaluate if the rooms you pay to be in are truly accelerating your business growth or just draining your resources. Because Investor Fuel and similar masterminds bring a lot of opportunities to learn. Things like "hot seats" where members present challenges quarterly, peer feedback, and the opportunity to execute action items.We go to network, provide value like education and back office clarity, and build long-term trust rather than hard-sell. These are just a few things we can do to get and give value at these events. You can strategically leverage your group to get more clients, increase your revenue, and scale effectively. But it's also important to identify when it's time to cut your losses and pivot toward more effective resources for your specific stage of growth. Plus some interesting stories along the way.WHAT YOU'LL LEARN✔ What a business mastermind is and How its helpful for your business✔ Why being in the room with the right people matters✔ How to decide if you're getting enough out of business masterminds✔ How to Pivot and Reevaluate what you're doing at these events✔ Why building a client relationship is important✔ Learn to identify when it's time to cut your losses and pivot toward more effective resources for your specific stage of growth✔ AI's Role: it can be helpful, but it cannot replace communityABOUT MEI'm Casey Quinn, entrepreneur, investor, and founder of SteelPoint. Through acquisitions, partnerships, and operational leadership, I help founder-led businesses scale through accountability, strategy, leadership development, and long-term value creation.Subscribe for more conversations on entrepreneurship, leadership, personal growth, communication, accountability, investing, and building businesses that create lasting impact.🔗 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=wwXIfrInstagram: https://www.instagram.com/caseyryanquinn?igsh=MTdqeGU2M2Vnb2R5cA==LinkedIn: https://www.linkedin.com/in/caseyryanquinn

  4. 10 Jul

    If Giving Back Isn't A Part Of Your Business Model, You're Missing The Mark

    Join our Skool Community: https://www.skool.com/steelpointfoundry/aboutCan giving to charity actually grow your business? The answer might surprise you; and it could be the most strategic decision you make this year.In this episode of The Never Perfect Podcast, we're diving into the world of corporate social responsibility (CSR) and what it truly means for your bottom line. From boosting brand reputation and employee morale to attracting loyal customers and networking with Investors, charity for business is more than just feeling good, it's smart strategy.WHAT YOU'LL LEARN✔ Why CSR is one of the most underrated growth levers for entrepreneurs and business owners✔ How to plan and launch your own charity event from scratch, even on a small budget✔ First steps toward starting a nonprofit organization or partnering with an existing cause✔ Why corporate social responsibility isn't just for big brands, and how small businesses can lead the charge✔ The link between business ethics, sustainability, and long-term brand trust✔ Building trust through accountability✔ Growing your business beyond social media✔ Long-term lessons for entrepreneurs and investorsWhether you've never thought about giving back or you're ready to build something bigger than your business, this episode gives you the mindset shift AND the practical roadmap to get started.ABOUT MEI'm Casey Quinn, entrepreneur, investor, and founder of SteelPoint. I help founder-led businesses scale through leadership, accountability, acquisitions, and operational excellence.Subscribe for more conversations on entrepreneurship, leadership, investing, communication, business growth, and building companies that create lasting impact.🔗 RESOURCES & LINKS► Learn more about me: 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/caseyryanquinnJoin our Skool Community: https://www.skool.com/steelpointfoundry/aboutLearn more about me at caseyryanquinn.com

  5. 26 Jun

    What Is An Investment Club? I Hiring Our President I Has a Prospect Ghosted You?

    -►More info on the SteelPoint Collective: https://www.fractional.app/p/steelpointcollective What happens when one of your biggest business launches gets completely derailed by something you can't control? In this episode of the Never Perfect Podcast, TJ and I take you behind the scenes of the SteelPoint Collective Investment Club, why we built it, and the unexpected challenge that forced us to postpone its launch. Before we dive in, here's an important update. When this episode was recorded, we were preparing to officially launch the SteelPoint Collective Investment Club. Shortly afterward, TJ's Facebook and Instagram accounts were unexpectedly disabled by Meta during launch week. Since social media is one of our primary ways of educating our audience, we've decided to postpone the launch until his accounts are restored and we can give the launch the attention it deserves. We'll announce a new date soon. Although the launch has been delayed, the conversation is more relevant than ever. We explain why we created the SteelPoint Collective Investment Club and how it was designed to provide more than passive investing. Our goal is to give entrepreneurs and investors the opportunity to learn directly from experienced operators while understanding how professional hard money lenders evaluate deals, protect investor capital, assess borrower risk, and make lending decisions. We also discuss one of the biggest lessons every entrepreneur should learn: never build your business entirely on platforms you don't own. TJ shares what it was like having his Meta accounts shut down without warning and how that experience reinforced the importance of building email lists, CRM systems, genuine relationships, and multiple marketing channels instead of relying solely on social media. Later in the episode, I share lessons from our executive search for a President at SteelPoint. We discuss hiring great leaders, protecting company culture, conducting transparent interviews, and why many hiring conversations become long-term business relationships even when someone isn't selected for the role. Finally, we dive into communication, accountability, follow-up, and one of the biggest frustrations every entrepreneur experiences: people not doing what they say they're going to do. We talk about respecting people's time, following through on commitments, improving communication, and why consistency remains one of the greatest competitive advantages in business. If you're interested in real estate investing, entrepreneurship, passive income, leadership, hard money lending, private lending, investor education, communication, business growth, and raising capital, this episode is full of practical lessons you can immediately apply to your business and life. WHAT YOU'LL LEARN ✔ Why we created the SteelPoint Collective Investment Club ✔ Why the launch has been postponed ✔ Passive investing vs. investor education ✔ How professional lenders evaluate deals ✔ Why entrepreneurs should own their audience ✔ Leadership lessons from executive hiring ✔ Better communication and follow-up strategies ✔ Building trust through accountability ✔ Growing your business beyond social media ✔ Long-term lessons for entrepreneurs and investors WHO THIS EPISODE IS FOR → Entrepreneurs → Business owners → Real estate investors ABOUT ME I'm Casey Quinn, entrepreneur, investor, and founder of SteelPoint. I help founder-led businesses scale through leadership, accountability, acquisitions, and operational excellence. ABOUT TJ BENCHO TJ Bencho is an entrepreneur, investor, and Director of Investor Relations at SteelPoint Capital. He helps investors build wealth while educating entrepreneurs on leadership, investing, and relationship building. 🔗 RESOURCES & LINKS ► Learn more about me ► Subscribe to the Never Perfect Podcast ► Casey's links: - Facebook - Instagram - LinkedIn ► TJ's links: - Facebook - Instagram - LinkedIn

  6. 20 Jun

    You Need to Take Extreme Ownership Or You'll Never Get Anywhere

    ► Join our FREE Skool Community here What if the biggest thing holding you back in business, leadership, relationships, and personal growth isn't a lack of talent or opportunity but a lack of ownership? In this episode, TJ and I dive into the core values that drive everything we do: communication, extreme ownership, transparency, accountability, and taking action. I've always believed that communication is one of the most undervalued skills in business and life. Whether you're leading a company, serving customers, managing employees, or building relationships, clarity almost always comes from communication. Too many people avoid difficult conversations, make assumptions, or wait for answers instead of creating them. Throughout this conversation, we discuss how fear and ego are often the root cause of many challenges people face. Fear prevents people from taking action, having hard conversations, and making decisions. Ego prevents people from admitting mistakes, accepting responsibility, and learning from failure. When you eliminate fear and ego, you create opportunities for growth, stronger relationships, and better leadership. A major focus of this episode is extreme ownership and why accountability is one of the most important characteristics anyone can develop. We break down why blaming circumstances, customers, employees, spouses, business partners, or external factors rarely creates progress. Real growth begins when you stop asking who's at fault and start asking what you could have done better. We also discuss why mistakes are necessary for growth. Too many people spend their lives trying to avoid failure when the fastest way to improve is through action. Every decision, every mistake, and every lesson creates feedback that helps you become a better leader, entrepreneur, spouse, parent, and human being. TJ shares personal stories about entrepreneurship, marriage, recovery, faith, and leadership. We discuss how creating environments where people feel safe making mistakes leads to stronger teams, healthier relationships, and better long-term results. One of the biggest themes throughout this conversation is our core value of "Let's Go." Taking action creates momentum. Taking action creates learning. Taking action creates clarity. Most people stay stuck because they're waiting for certainty before they move. In reality, certainty comes from movement. If you're looking to become a stronger leader, improve your communication skills, build confidence, create better relationships, and develop the mindset necessary for long-term success, this episode is packed with practical lessons you can apply immediately. WHAT YOU'LL LEARN ✔ Why communication creates clarity ✔ How fear and ego hold people back ✔ The power of extreme ownership ✔ Why accountability drives growth ✔ How great leaders handle mistakes ✔ Why taking action beats waiting ✔ Building stronger teams and relationships ✔ Learning from failure and setbacks ✔ Creating a culture of trust and transparency ✔ The connection between ownership and happiness WHO THIS EPISODE IS FOR → Entrepreneurs and founders → Business owners and leaders → Sales professionals → Parents and spouses → People focused on personal growth → Anyone looking to improve communication and accountability ABOUT ME I'm Casey Quinn, entrepreneur, investor, and founder of SteelPoint. Through acquisitions, partnerships, and operational leadership, I help founder-led businesses scale through accountability, strategy, leadership development, and long-term value creation. ABOUT TJ BENCHO TJ Bencho is a business leader, entrepreneur, and leadership coach focused on helping people build stronger relationships, develop accountability, and live with greater purpose. 🔗 RESOURCES & LINKS ► Learn more about me here ► Subscribe to the Never Perfect Podcast ► Casey's links: FacebookInstagramLinkedIn ► TJ's links: FacebookInstagramLinkedIn

  7. 18 Jun

    The NEW Marketing Model That's Quietly Killing Traditional Agencies I A GAME CHANGER For Founders

    ► Join our FREE Skool Community: https://www.skool.com/steelpointfoundry/about Are you investing in marketing but still struggling to generate consistent leads, track ROI, and build a predictable growth system? In this episode, I sit down with Danielle Hollembaek to discuss one of the biggest challenges facing growing businesses today: marketing leadership. As companies scale, I've seen founders become responsible for managing agencies, freelancers, content creators, social media managers, and internal marketing teams without having clear strategic leadership in place. Danielle explains why most businesses don't need another marketing vendor they need someone leading the strategy. As the founder of Provato, a Fractional CMO company, Danielle shares how businesses can create accountability, improve reporting, align marketing efforts with revenue goals, and build systems that support long-term growth. We also discuss SteelPoint's first Council Summit and why I've invested heavily in building an ecosystem of founder-led businesses. I share why strong relationships, accountability, and collaboration create more value than traditional networking groups and how founder communities can accelerate growth. We dive into modern marketing leadership, hiring challenges, and how founders can avoid becoming the bottleneck inside their own organizations. Danielle also shares how she uses AI tools like Claude and Whisper, along with podcast transcripts and brand voice training, to create authentic content that sounds human and reflects a company's unique voice. Beyond business, we have an honest conversation about entrepreneurship, family life, leadership, and the realities of building companies while raising children. As Danielle prepares to welcome her fifth child while launching a new business, she shares lessons on prioritization, work-life integration, and why being fully present matters more than simply being available. If you're looking to improve your marketing strategy, generate more leads, increase accountability, or determine whether a Fractional CMO is right for your business, this episode is packed with practical insights you can implement immediately. WHAT YOU'LL LEARN ✔ What a Fractional CMO does ✔ Why founders struggle with marketing leadership ✔ Agency vs. Fractional CMO differences ✔ How Provato helps businesses scale marketing ✔ The role of accountability and KPIs ✔ Common marketing mistakes founders make ✔ Building systems that drive revenue ✔ Using AI without losing your brand voice ✔ Lessons from SteelPoint's Council Summit ✔ How founder communities accelerate growth ✔ Leadership and family balance WHO THIS EPISODE IS FOR → Entrepreneurs and founders → Small business owners → CEOs of growing companies → Marketing leaders and managers → EOS organizations → Founder-led businesses → Companies considering a Fractional CMO → Businesses looking to improve marketing ROI ABOUT ME I'm Casey Quinn, an entrepreneur, investor, and founder of SteelPoint. Through acquisitions, partnerships, and operational leadership, I help founder-led businesses scale through accountability, strategy, leadership development, and long-term value creation. ABOUT DANIELLE HOLLEMBAEK Danielle is the founder of Provato and a marketing strategist specializing in marketing leadership, content strategy, brand development, lead generation, and scalable marketing systems. ABOUT PROVATO Provato helps founder-led businesses build scalable marketing systems through Fractional CMO services, strategic planning, accountability, KPI tracking, team management, and growth-focused execution. Subscribe for more conversations on entrepreneurship, leadership, marketing strategy, EOS, investing, and scaling businesses. 🔗 RESOURCES & LINKS ► Learn more: www.caseyryanquinn.com ► Never Perfect Podcast: https://www.youtube.com/@caseyryanquinn ► Casey Quinn - Facebook - Instagram - LinkedIn ► Danielle Hollembaek - Facebook - Instagram - LinkedIn

  8. 13 Jun

    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.

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.

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