Never Perfect
by 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.
Episodes
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Why Your Executive Assistant Is the Most Important Hire You’ll Make | EOS Behind the Scenes
Is an executive assistant the most important hire a business owner can make? Casey Ryan Quinn sits down with his EA, Leandra, to break down how they run EOS without an implementer and what it really takes to support a visionary entrepreneur. Casey asks Leandra what she's learned running his…
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Inside a Golf Mastermind for Business Owners: What I Learned in Austin (M19 Recap)
Is a golf mastermind worth it for business owners? Casey showed up to M19 in Austin with the worst handicap of 32 entrepreneurs and a real dislike of meeting new people. Three days later, he had relationships he expects to keep for years. Co-host Alex asks Casey what it was actually like: How a...
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How We Replaced $20K/Month in Software With AI (Real Small Business Results)
We replaced $15K to $20K a month in software by building our own tools with AI. Here’s what actually changed inside our businesses in the last 12 months. Quick heads up: we apologize for the video quality on this one. Four guys in one small room. We hope you stay for the takes. It’s the Never...
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Viral Hate, a Duquesne Football Partnership, and Golf Deals | Hump Day Huddle Ep. 9
We went viral last week, and the internet roasted us. Casey Ryan Quinn and Al break down what going viral really looks like for a business, why chasing views is the wrong goal, and why authentic content wins with the people who actually want to work with you. Plus: the SteelPoint Capital x…
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How We Sold Out a First-Year Charity Golf Outing (144 Golfers)
Most first-year charity golf outings struggle to fill the course. This one sold out 144 golfers, turned away four groups, and kept 100 people around long after the last putt. Casey Ryan Quinn, Alex, and TJ recap the first annual Pat Quinn Memorial Golf Outing at Chartiers Country Club in...
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Real Estate Is Easy. People Are Hard. | A CEO on Leading 70+ Employees
Real estate is math. People are the hard part. Casey Ryan Quinn and Alex get into why leading a team of 70+ is the hardest thing in business, why face-to-face relationships are a competitive edge in the social media era, and why they passed on a golf course investment fund despite a great trip....
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Same Zip Code, $90K Difference: How to Underwrite a Fix and Flip Street by Street
Marc McLaughlin went from construction and design work for another investor to 10+ fix and flips with SteelPoint in about 18 months, and he lost 100 pounds along the way. He joins Casey Ryan Quinn to talk about what changed his mindset, how he got burned by private lenders before finding the…
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Why Relationship Selling Beats High-Pressure Sales Every Time | Hump Day Huddle Ep. 7
Should you hire your friend? Casey Ryan Quinn and Alex Orosz mark two years of working together at SteelPoint Capital. They cover leaving a 24/7 corporate job, the real risk of mixing business and friendship, and why the business has to be bigger than any one person. They also explain why...
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Your Why Isn't Enough: Vision Clarity, Execution & Financial Clarity for Entrepreneurs
Successful owners keep starting new businesses without knowing why, and it's costing them. Casey Ryan Quinn and TJ Bencho break down why your why isn't enough, vision clarity vs. shiny object syndrome, and why most owners never implement EOS. Subscribe to the Never Perfect Podcast so you don't…
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Founder Authenticity, AI Meeting Prep & Mike Tomlin's 12-Year Minecraft City | Hump Day Huddle Ep. 6
Casey Ryan Quinn and Alex Orosz debate whether business owners should share their family online. Casey argues that authenticity is what builds trust with investors and clients, while Alex explains why he keeps his family private in the age of AI. They break down Accruity's EOS quarterly planning...
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Hiring a President to Run My Company: EOS Visionary vs Integrator Explained
Two months ago, Casey Ryan Quinn hired Kelly DeAngelo as President of SteelPoint Capital — after using AI to build a profile of exactly who he needed before the job was ever posted. Kelly spent 21 years climbing from floor engineer to running a $600M budget at the world's largest sugar refiner....
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How to Stay Consistent When It Gets Hard: Lessons from a 50K in 50 States in 50 Days
Brady McDonald just finished a 50K in every state over 50 straight days, ending in Hawaii and raising $1 million for Make-A-Wish. Casey Ryan Quinn and TJ Bencho unpack why the fundraising may be the more impressive feat, and what his stop in Pittsburgh looked like from the inside. Then they get...
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How to Win Q4 with EOS: Planning, Alignment & Accountability | Hump Day Huddle Ep. 5
With Casey traveling, Alex Orosz brings SteelPoint Chief of Staff Leandra Watson in from the bullpen to recap a packed week at SteelPoint Capital. They break down the leadership team's EOS quarterly session and why Q4 planning is the most important planning of the year. They also share how to…
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Married & Business Partners: How One Couple Built a 23-Door Real Estate Portfolio
Three years ago, Josh and Jess Varga were running a hair salon and working a union job with five real estate deals to their name. Today they run a full-time real estate investment business together — doing 3-4 deals a month and managing 23 rental doors. Casey Ryan Quinn talks with them about...
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Pro-Am Heartbreak, a Sold-Out Golf Outing & Our Steelers Are 1-0 | Hump Day Huddle Ep. 4
This week on Hump Day Huddle, Casey and Alex recap a business trip gone sideways, a Steelers 1-0 start with TJ Watt back and Aaron Rodgers making his debut, and a fantasy football lineup call that cost more than bragging rights. They close out with a pro-am heartbreak on the greens and updates on...
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Honoring My Dad: Inside the First Annual Pat Quinn Memorial Golf Outing
Casey Ryan Quinn honors his late father with the First Annual Pat Quinn Memorial Golf Outing, a new SteelPoint Foundation charity event in Pittsburgh. Co-host Alex Orosz flips the script and interviews Casey on the "Legion League" history behind the idea, why the timing finally worked this year,...
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Stolen Pitch Decks, Hiring Mistakes, & Charity Golf | Hump Day Huddle Ep. 3
On this episode of the Never Perfect Podcast, Casey Ryan Quinn and Alex Orosz break down a wild story: a competitor scraped Alex's tax webinar — slides, script, even his jokes — straight off a YouTube recording using AI, then rebranded it as their own. They walk through how they caught it and...
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Real Estate Agents Are Quitting Brokerages: How to Recruit & Retain Them in 2026
Volume is down, deals are stalling, and agents are jumping ship — so what separates the real estate businesses that are thriving from the ones that are bleeding out? Casey Ryan Quinn sits down with Jeff Boscaino to unpack the real strategy shifts happening in recruiting, retention, and revenue...
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The Human AI Sandwich: How Top Leaders Actually Use AI | Hump Day Huddle Ep. 2
Casey Ryan Quinn and Alex Orosz sit down for another Hump Day Huddle to unpack what they actually learned from a company AI strategy summit — including a framework called the "Human AI Sandwich" — and why the top two use cases for AI in America (companionship and counseling) are a warning sign…
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Why Your Business Issues Keep Coming Back (And How EOS IDS Fixes It)
Most businesses don't fail from a lack of ideas — they fail because the same issues keep coming back. Casey Ryan Quinn and TJ Bencho break down IDS (Identify, Discuss, Solve), the EOS issue-solving framework from Traction by Gino Wickman, and share how they actually run their own leadership...
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Introducing the Hump Day Huddle: Business, Life, No Filter
Welcome to the first-ever Hump Day Huddle on the Never Perfect Podcast. Every Wednesday, Casey Ryan Quinn and Alex are bringing you unfiltered, real-time conversation on what's actually happening in business and life — because in today's world, they're the same thing.In this launch episode, Casey...
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The BRRRR Method, DSCR Loans, and Why Leverage Builds Real Wealth
What happens when a home sale falls through the morning of closing? Casey Ryan Quinn sits down with Evan, Co-Visionary at Local First Lending, to talk through it — then dig into the real estate strategy that's built his portfolio: the BRRRR method (Buy, Rehab, Rent, Refinance, Repeat), DSCR...
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Marketing Isn’t About Leads, It’s About Revenue | How to Build a Marketing System That Works
Learn more about me at caseyryanquinn.comWhat actually makes marketing work?It isn't more posts, more followers, more likes, or even more leads.In this episode of the Never Perfect Podcast, Casey sits down with Rebecca from Accruity to break down what marketing actually looks like behind the...
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EP 42
EP 42
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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...
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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...
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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…
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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...
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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...
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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…
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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...
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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,...
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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...
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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...
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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...
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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...
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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...
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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…
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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...
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I'm Letting Alex Take My Place I Being The Face Of A Brand
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...
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The Truth About AI Nobody Wants to Admit I Why Human Connection Matters More in the Age of AI
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...
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We Ran The Pittsburgh Marathon I Doing Hard Things I How We Adapt To The Unexpected.
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...
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How to Build Wealth with BRRRR (Even When Rates Are High)
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...
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Customer Success, Executive Assistances, and Entrepreneurs: The Biggest Mistake We Make When They Scale
What actually breaks as a company starts to scale; the work, the people, or the communication? In this episode of the Never Perfect Podcast, I sit down with Stacy Cvengros, Manager of Client Success at Accruity, to unpack one of the most overlooked drivers of growth in any service-based business:...
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The Right-Hand Role Every Founder Needs to Grow
What does it really take to support a fast-moving founder, manage priorities across multiple companies, and keep execution moving when everything feels urgent? In this episode of It’s Never Perfect, I sit down with Leandra, my Chief of Staff and Executive Assistant, to talk about what it looks…
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From Chaos to Clarity | Why EOS Works for Growing Businesses
What does it actually take to build a business that scales without everything falling on the founder? In this episode, I sit down with TJ to break down one of the biggest drivers behind how we operate our private equity firm and the companies inside our portfolio: EOS, the Entrepreneurial…
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The Truth About Investor Relations & Building Real Community I From Corporate Comfort to Real Estate Growth With Our Investor Team
What happens when you leave the comfort of corporate or a stable career and step into something completely new? In this episode of the Never Perfect Podcast, we sit down with Dom and Pete to break down what it actually looks like to transition into real estate investing, investor relations, and a...
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Building a Family Legacy That Actually Lasts (Spoiler: It's Not Just About Money)
What does it actually mean to build a family legacy that lasts? In this episode of It’s Never Perfect, I dive into a conversation that started around business structure and quickly turned into something much deeper how to think about wealth, leadership, and the responsibility that comes with...
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From Team Member to Real Estate Partner (And Now Leading a New Lending Company Launch)
Are you trying to figure out how to build real partnerships, grow inside a company, and create something of your own without losing the relationships that matter most? In this episode of Never Perfect, Casey Quinn sits down with TJ and Evan for a conversation about entrepreneurship, friendship…
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Stop Waiting to Feel Ready and Start Building I How Mike Lucas Built Rentals and Launched A Service Business
Are you trying to figure out how to break into real estate, build wealth, and eventually create something of your own? In this episode of Never Perfect, Casey Quinn sits down with Mike Lucas to unpack what it really looks like to go from a young guy with no money and no roadmap to a business…
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About this show
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.
Hosted by
Casey Ryan Quinn
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