Never Perfect

Join our Skool Community: https://www.skool.com/steelpointfoundry/aboutWhat does it actually take to walk away from a $35 billion company after 15 years — with a growing family, a spouse with her own demanding career, and zero certainty about what comes next? In this episode, Casey sits down with Kevin Rombach, COO of Accruity, to unpack one of the most honest conversations we've had on this show. Kevin didn't just change jobs. He changed everything about how he operates, how he thinks, and what he believes is possible when you're willing to get uncomfortable.Kevin spent nearly 15 years climbing the ranks at UPMC, one of the largest hospital systems in the country. He was well-compensated, well-respected, and well-protected by the kind of bureaucratic structure that corporate America is built on. And then Casey came calling — not once, but multiple times over the course of three years. What finally made Kevin say yes? The answer isn't what you'd expect, and it's something every person sitting in a comfortable-but-unfulfilling job needs to hear.This episode goes deep on the two forces Casey believes are destroying people's potential: fear and ego. Kevin lived both. The ego of walking away from a prestigious title. The fear of failing the people who believed in him. Together, they break down exactly how Kevin navigated those emotions and what the mental framework looks like when you decide to bet on yourself — not for yourself, but for something bigger.They also get into what it's really like to serve entrepreneurs after spending a career serving corporate controllers and finance departments. Entrepreneurs think differently, move faster, and demand a completely different level of communication and preparation. Kevin shares what he's learned about showing up ready, adding real value, and what it means to truly listen to a client instead of walking in thinking you already have all the answers.And in the final stretch, Casey turns the table and asks Kevin the question he now asks every guest: if you could go back and talk to yourself at the beginning of this journey, what would you say? Kevin's answer, focus is a superpower, remove your ego, don't overhire, react to the market faster, and for the love of everything, celebrate your wins — is the kind of hard-earned wisdom that only comes from living it.If you're sitting on the fence about a big decision, grinding without enjoying the journey, or trying to figure out how to scale smarter without burning everything down, this episode is for you.

Join our Skool Community: https://www.skool.com/steelpointfoundry/aboutAre you struggling to let go of control in your business? In this episode of Never Perfect, Casey Ryan Quinn sits down with his right-hand executive assistant, Leandra, to discuss the transformative power of delegation and trust. After nearly five years of working together across multiple companies including City Life, SteelPoint, and Acruity, they share the raw truth about what it really takes to build an unbreakable partnership between a CEO and an EA.Leandra opens up about her transition from an HR role into the executive assistant seat, tackling the common misconceptions about the position and how she shifted her mindset to find immense value and self-worth in being the ultimate multiplier for the business. They dive deep into the specific challenges of handing over the most guarded aspect of any entrepreneur's life: email management. Casey reveals his own struggles with patience and the impulse to micromanage, while Leandra explains her strategies for protecting his time and sanity amidst a chaotic schedule of meetings, travel, and strategic planning.Throughout this candid conversation, you will discover the importance of testing trust early on, why reserving the right to get smarter is a crucial leadership philosophy, and how taking massive action while owning your mistakes leads to better business outcomes. Whether you are an entrepreneur wondering if you are ready to hire your first executive assistant, or an EA looking to level up your impact, this episode is packed with actionable insights on creating clarity, managing egos, and navigating the complex ecosystem of running multiple businesses simultaneously.

Join our Skool Community: https://www.skool.com/steelpointfoundry/aboutWhat does it actually take to walk away from a steady corporate paycheck and build real wealth through real estate? In this episode of the Never Perfect Podcast, Casey Ryan Quinn sits down with Evan (Big E) — the driving force behind City Life Property Management's business development and owner relations. Over six years, Evan has helped scale one of Pittsburgh's most respected property management companies while quietly building his own real estate portfolio using the same proven strategies he learned on the job.Evan grew up in a blue-collar household, earned his master's at Penn State Behrend, and landed a corporate job in oil and gas — only to realize within weeks that the siloed, headphones-on environment was the exact opposite of everything that made him thrive. After six months, he took a half day from work, walked into a City Life interview, and immediately knew he had found his people.What followed was six years of accelerated, real-world education. Evan learned how to screen tenants, manage vendors, scope renovations, and build owner relationships — all while studying the investment side of the business. When his first opportunity appeared, he executed a textbook BRRRR strategy: he purchased a property in Carrick for $65,000, renovated it, leased it out, and refinanced on the back end. The bank funded 100% of his total cost, leaving him with a property he owned outright with zero dollars remaining in the deal. Casey calls this an infinity return — and Evan still owns that house today.From that first deal, Evan built an entire block-level portfolio. By building relationships with neighbors during the renovation, he ended up acquiring three properties on the same street, with a fourth in progress. This is the kind of organic, relationship-driven investing that no algorithm can teach.This conversation also explores City Life's culture: the idea that collaboration, not competition, is the ultimate competitive advantage. Evan and Casey discuss how the lack of collaboration in corporate environments pushed them both toward entrepreneurship — and how building a team that genuinely wants each other to win has become the foundation of everything they are building, from City Life to Steel Point Capital to Acrruity.Whether you are a first-time investor trying to understand the BRRRR method, a W2 employee wondering if entrepreneurship is possible, or a property management professional looking to scale, this episode delivers the real, unfiltered answers you have been searching for.

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Look, we don't do a ton of prep around here, you already know that. But this one I was genuinely excited for. I brought my guy Alex on the mic today, and if you've been around for a while, you already know who he is. We went to college together, he's been one of my closest friends for years, and now he runs business development, sales, and marketing at Accruity. He's also a limited partner in SteelPoint Capital. So yeah, he's all in on everything we're building and this conversation gets into all of it.We talk about what it's actually like working with your best friend every single day. The highs, like the time we went out to Arizona, absolutely crushed an event, signed 14 clients on the spot, and were dapping each other up every ten minutes at the bar afterward. And the lows, like flying to Dallas, being told hundreds of people would be there, and walking into a room with literally one person in it. Both of those things happen, and when you're doing it with someone you care about, they hit different in both directions.Alex came from the corporate world, big software companies, structured sales cycles, RFP processes where everything was laid out for you. Coming into the entrepreneurial space at Accruity was a completely different animal. No timelines, no escalation paths, no boss to call when someone ghosts you. The biggest thing he says he learned? Follow-up is everything. Not just following up once — consistent, relentless, respectful follow-up. Because the entrepreneurs and real estate investors we work with aren't ignoring you because they don't like you. They're just putting out fires and dealing with the next deal. If you stay in front of them, the relationship holds. And when the timing is finally right, you're the first call they make.We also get into the difference between selling to entrepreneurs versus selling to corporate managers and why those are two completely different conversations. Entrepreneurs don't have a defined role, they don't have someone to delegate to, and they're doing a hundred things at once. That's exactly why financial clarity matters so much. When you don't know your numbers, you can't delegate, you can't sleep at night, and you definitely can't grow. I walk through a real coaching call I had that morning with a CEO who had no idea what his breakeven was — and how working backwards from a 13-week rolling cash forecast all the way to how many leads he needed that month completely changed the picture for him.We close it out talking about what it takes to make a leap like Alex made — leaving a stable corporate career to go work for your best friend at a startup. His advice is simple: be yourself, find people who know what you're good at and let you do that, and don't be afraid to have the hard conversations. Communication solves everything. And as TJ put it in a post recently, the money's in the follow-up. Every time.

Join our Skool Community: https://www.skool.com/steelpointfoundry/aboutEvery entrepreneur faces losses — but most never learn how to handle them without letting them spiral into self-doubt, paralysis, and burnout. In this solo episode, Casey Ryan Quinn gets raw and real about the emotional rollercoaster of building a business, why losses are not just inevitable but necessary, and the exact mental framework he uses to bounce back faster every single time.Casey opens up about his own journey — from building a 900-door real estate portfolio and navigating brutal market shifts, to launching a wholesale company that hit $1.2M in year one and then shutting it completely down. He breaks down what he actually lost, what he gained, and why the way you think about a loss is the only thing that separates entrepreneurs who make it from those who don't.This episode covers three core pillars: accepting that losses are part of the process, evaluating and upgrading your circle of influence, and finding mentors who are close enough to your level to actually be relatable. Casey also digs into the power of daily culture — from the Starbucks barista who starts your morning right, to the team members who have your back when everything goes sideways.Whether you're brand new to entrepreneurship, seven years into building your company, or grinding in a W-2 job while dreaming of something bigger — this episode will shift how you see failure, how you respond to it, and how quickly you recover. The goal isn't to eliminate the highs and lows. It's to stop riding the roller coaster and start riding the merry-go-round: steady, enjoyable, and built to last.If this episode resonated with you, Casey and the team at The Foundry are building a community and inner circle for entrepreneurs who want to grow their wealth, their health, and their mindset together. Check the links below to learn more.Don't forget to like, subscribe, and share this episode — it helps more entrepreneurs find this content.

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Fear of public speaking is one of the most common and most paralyzing obstacles entrepreneurs face. In Episode 3 of Never Perfect, Casey Ryan Quinn and co-host T.J. Bencho pull back the curtain on what it actually feels like to step on stage, why the nerves never fully go away, and why that's perfectly okay.Casey shares raw, unfiltered lessons from keynoting two major real estate masterminds back-to-back including the time he completely lost his train of thought mid-keynote in front of hundreds of people and kept right on going. T.J. brings his own battle-tested perspective, from speaking at real estate investment meetings at 16 years old to presenting on international stages in Australia.In this episode, you'll learn:Why the fear of being judged is the #1 thing holding you back from the stageHow to connect with any audience — even on a topic you didn't chooseWhy over-scripting kills your delivery (and what to do instead)The NLP techniques elite speakers like Ed Mylett and Brandon Brittingham use to move audiences emotionallyHow public speaking and content creation are the exact same skillThe "cookies and skinny" mindset framework (credit: Hormozi) that will change how you think about sacrifice and goals Why progress over perfection is the only standard that mattersWhether you're a first-time speaker terrified of the spotlight or a seasoned entrepreneur looking to sharpen your stage presence, this conversation will push you to stop waiting and start doing. Action. Action. Action.Never Perfect is the podcast for entrepreneurs who are done pretending business is polished. Hosted by Casey Ryan Quinn — serial entrepreneur, CPA, Co-Founder of SteelPoint Capital, CityLife Residential, Accruity, and SteelPoint Foundry — this show delivers straight-from-the-heart, unscripted conversations about what it really takes to build businesses, lead teams, and grow as a human being.Follow Casey: https://www.instagram.com/caseyryanquinn/Connect on LinkedIn: https://www.linkedin.com/in/caseyryanquinnFollow on Facebook: https://www.facebook.com/CaseyRyanQuinn

In this episode of Never Perfect, host Casey Ryan Quinn is joined by his Accruity co-founder, Jeff Boschino, for a raw and honest conversation about their entrepreneurial journey. They dive deep into the realities of leaving a W-2 job to start a business, the myth of instant freedom, and the true meaning of burnout. Casey and Jeff share their struggles and triumphs in building Accruity, a financial services firm, from the ground up. They discuss the importance of communication, delivering value to clients, and the critical role of financial literacy for every business owner. If you're an aspiring or current entrepreneur, this episode is packed with valuable insights and lessons learned from the front lines of building a business. Want to get PERSONAL access to Casey? Apply for our program here: https://steelpointfoundry.com/

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In this inaugural episode of "Never Perfect with Casey Ryan Quinn", Casey Ryan Quinn and his long-time business partner, TJ, for a candid and unscripted conversation about the realities of entrepreneurship. They dive deep into why they're ditching the traditional, overly-produced content model in favor of raw, authentic discussions that provide real value. Discover their philosophy of "progress over perfection" and how it has guided them in building multiple successful businesses.If you're an entrepreneur who's tired of the fluff and looking for genuine insights on how to grow your business and stay true to yourself, this episode is for you.

IN THIS VIDEO, YOU'LL LEARN:

Why authenticity is the most crucial ingredient for long-term success.The story behind their new mastermind community, "The Foundry."A breakdown of Casey's diverse business portfolio, from real estate to a 7-figure flooring and paint company.Actionable advice on how to build a strong, value-driven business.

TIMESTAMPS:

00:00 - Introduction: Progress Over Perfection

02:41 - Welcoming TJ: A Partner from the Beginning

03:30 - The Flaws of Traditional Content Creation

06:00 - The Power of Authenticity in Business and Life

09:24 - Introducing "The Foundry": A Community for Real Entrepreneurs14:00 - A Look Inside Casey's Business Empire

18:26 - Final Thoughts and What's to Come

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In this episode, I sit down with Peyton, a key member of my team, to discuss his incredible journey from the world of banking to becoming a successful real estate investor. Peyton's story is a powerful testament to the importance of taking massive action and immersing yourself in the right environment to achieve your goals. We kick things off with a formal introduction to Peyton and he shares his background, starting as a commercial analyst in banking and how listening to BiggerPockets inspired him to make a change. He talks about the challenges of working in a traditional banking environment and the desire for something more dynamic and relatable. Peyton then dives into his transition to the real estate world, starting as a transaction coordinator for a wholesale company. He shares the invaluable lessons he learned from his mentor, TJ, about consistency, time-blocking, and the relentless follow-up required to succeed in wholesaling. We explore the high-pressure environment of transaction coordination, managing sellers, buyers, and title companies to ensure deals close. Peyton emphasizes the importance of taking control of situations and not leaving things to chance, a lesson that has had a profound impact on his personal and professional life.We then discuss the evolution of Peyton's role within my company, from the shutdown of the wholesale division to his current position in lending operations. He candidly shares his initial uncertainty and how a pivotal conversation with me and my wife, Steph, gave him the confidence to embrace a new challenge. Peyton now handles all borrower-side operations, from underwriting and transaction management to creating loan documents and managing draws. He provides a behind-the-scenes look at his underwriting process, explaining the crucial difference between underwriting a deal and underwriting a borrower. He also highlights the importance of building relationships with borrowers and providing them with the support and guidance they need to succeed.Of course, we couldn't have this conversation without talking about Peyton's own entrepreneurial journey in real estate. He shares the details of his first flip, which netted him a $35,000 profit, and gives an update on his second flip, which is nearing completion. We delve into the mindset of a young investor, and Peyton opens up about his conservative approach to risk, which stems from his parents' experience during the 2008 financial crisis. This leads to a broader discussion about overcoming fear, taking calculated risks, and the power of having a supportive network. Peyton's story is a powerful reminder that the path to success is not always linear, and that with the right mindset and support system, anyone can achieve their real estate investing goals. We wrap up with Peyton's key piece of advice for the audience: just take action.Timestamps00:20 - Introduction to Peyton