Never Perfect

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 Duquesne football partnership launch, a halftime interview with Tim Benz, a 35-point comeback, and why member-guest golf might be the best networking event for entrepreneurs.

In this episode:

• The dark side of going viral
• Authentic marketing vs. influencer marketing for business owners
• Getting out of your comfort zone with your first post
• Inside our Duquesne football partnership
• Golf as a relationship-building strategy
• 
  

New Humpday Huddle every Wednesday. Follow the show so you don’t miss one.

Stay Connected

• Start Investing: steelpointcapital.net
• Learn More About Me: caseyryanquinn.com
• Follow Me on Socials: @CaseyRyanQuinn
• Follow Alex on Socials: @Alex.M.Orosz

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 Pittsburgh. They cover how a long-time family idea finally became real, how the team lined up sponsors and donated prizes, and why people from completely different worlds connected so easily.

They also share the best moments from the course, a heartfelt speech, and the changes they’re making next year to raise even more.

You’ll learn:

• How to sell out a charity golf outing in year one
• How to find sponsors and donated prizes through your network
• How smart pairings create a better guest experience
• How business owners can build giving into their company’s mission

Thank you to every sponsor, golfer, volunteer, and the Chartiers staff.

The It’s Never Perfect Podcast: real life, real business, no filter. Follow for weekly conversations on entrepreneurship, investing, and building something that matters.

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.

Plus: what Rich Paul’s negotiating playbook and the Lakers’ front office teach about scaling, how to choose who you take advice from, and a candid look at today’s real estate market. For business owners, investors, and entrepreneurs who know it’s never perfect.

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 right partner, and what the last year taught him about risk. He also explains why a $9,000 flip might have been better as a rental.

They dig into underwriting in Pittsburgh, one of the country’s top fix-and-flip markets for ROI, including a South Park sale where the street alone meant about a $90K difference. They also cover when design upgrades pay off, and why one phone call beats a week of texting. Subscribe to the Never Perfect Podcast so you don’t miss an episode.

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 relationship selling beats high-pressure tactics after an interesting experience with a famous podcast team.

Plus an employee recognition golf day, Duquesne homecoming, the story behind the Steelers’ one-sided helmet logo, and a golf networking trip to a new Tiger Woods design in Virginia.

Hump Day Huddle is part of the Never Perfect Podcast and drops every Wednesday. Subscribe so you don’t miss one.

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 miss one.

🔗 Links

Start Investing: ⁠⁠⁠steelpointcapital.net⁠⁠⁠

Learn More About Me: ⁠⁠⁠caseyryanquinn.com⁠⁠⁠

Follow Me on Socials: @CaseyRyanQuinn

Follow Alex on Instagram: @alex.m.orosz

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 session, where an AI-assisted prep document helped the team finish about two hours early, and talk about pivoting a service offering and making a career change without changing buildings. Then they react to Mike Tomlin's 12-year Minecraft city and ask where leaders find the time. Plus a country club member-guest recap and a 9/11 audiobook recommendation.

Hump Day Huddle is part of the Never Perfect Podcast and drops every Wednesday. Subscribe so you don't miss one.

🔗 Links

Start Investing: ⁠⁠steelpointcapital.net⁠⁠

Learn More About Me: ⁠⁠caseyryanquinn.com⁠⁠

Follow Me on Socials: @CaseyRyanQuinn

Follow Alex on Instagram: @alex.m.orosz

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.

Casey Ryan Quinn talks with him about the Visionary vs. Integrator dynamic in EOS, what it feels like for a founder to hand off decisions he's made solo for years, and how SteelPoint went from missing most of its quarterly goals to hitting nearly all of them in one quarter.

The Never Perfect Podcast is hosted by Casey Ryan Quinn, Founder and CEO of SteelPoint Capital. New episodes drop every week — subscribe so you don't miss one.

🔗 Links

Start Investing: ⁠steelpointcapital.net⁠

Learn More About Me: ⁠caseyryanquinn.com⁠

Follow Me on Socials: @CaseyRyanQuinn

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 into how high performers stay consistent. TJ walks through the daily non-negotiables he's built over 20 years. Casey shares his expectations vs. reality framework, and why "I don't have time" really means you chose something else.

Like, subscribe and join us for the next one.

Follow Brady here.Watch Brady's Pittsburgh run here.Donate to Make-A-Wish through Brady's campaign here.

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 tell real alignment from avoided conflict, and how growing companies adjust L10 meetings for small teams.

Then they get into charity week: a sold-out first-year golf outing and the David Alan Fashion Show benefiting Casey's Clubhouse. They close on hiring for culture and why no one can hide in an EOS company.

Hump Day Huddle is part of the Never Perfect Podcast and drops every Wednesday. Subscribe so you don't miss one.

🔗 Links

Start Investing: ⁠steelpointcapital.net⁠

Learn More About Me: ⁠caseyryanquinn.com⁠

Follow Me on Socials: @CaseyRyanQuinn

Follow Alex on Instagram: @alex.m.orosz