CIAP Friday Member Spotlight: Orlando Pastore, Advisor (Owner) of Pastore Business Solutions
Every Friday, CIAP’s Member Spotlight gives us a chance to get to know one of the professionals, entrepreneurs, and business owners who make Chicagoland’s Italian-American community stronger. This week, we’re pleased to feature Orlando Pastore, Advisor (Owner) of Pastore Business Solutions.
Orlando’s story runs from public accounting through corporate finance and into a business of his own, with an early-career setback along the way that reshaped how he thinks about planning, data, and growth. It’s a story about building something steady, one careful step at a time.
From public accounting to Pastore Business Solutions
Orlando’s career began in public accounting, where the work is detail-heavy by design: statements, reconciliations, and the discipline of getting numbers right. From there he moved into corporate accounting, and then into corporate finance roles, where the questions get bigger. Instead of recording what happened, the job becomes helping decide what should happen next.
Along the way, something else became clear. What interested him most wasn’t the size of the company; it was the people behind smaller ones. Entrepreneurs and small business owners were doing important work, often without the financial support systems that larger organizations take for granted.
So he launched Pastore Business Solutions, with a focus on small business finance and strategy. The idea is simple to say and useful to hear: bring “large company financial expertise, sized for the small business owner.”
An artist's impression of the work behind small business finance.
A setback that taught him to think ahead
Early in his career, Orlando faced a setback that changed how he thinks. He doesn’t treat it as a footnote; he treats it as a lesson that still guides him.
“An early career setback put everything into perspective for me. I learned that nothing can be taken for granted and that I always needed to be thinking ahead and thinking strategically about the future.”
He adds that the experience taught him something about himself as well: “I am the only person that can put limits on my learning and growth potential.”
For anyone building a business or a career, that’s a quietly practical way to look at things. Plans change, markets shift, and circumstances don’t always cooperate. What stays with you is the habit of looking ahead, learning continuously, and refusing to treat a rough patch as a ceiling.
His advice: consistency and honest data
Ask Orlando what advice he’d give business owners and the answer comes in two parts: steady effort, and honest information.
“Never underestimate the exponential power of consistency and incremental improvements.”
And on the second part: “Data doesn't lie... We all tell ourselves stories about our business and our industry, but when our stories align with the data, we can stop being reactive and start being strategic.”
An artist's impression of generations of Italian-American enterprise in Chicago.
Italian-American heritage and working together
When Orlando talks about his Italian-American heritage, he starts with gratitude for the generations who came before.
“The generations of Italian Americans that came before us paved the way for us through hard work, persistence and grit. They instilled in us a rich history of traditions & culture that was enhanced by the lessons and experiences they encountered as Americans.”
And he keeps the lesson forward-looking: “Being Italian American is a constant reminder of what we can achieve when we work hard and more importantly, when we work together!”
That spirit shows up in how Orlando works with small business owners: patiently, consistently, and in partnership. It’s also the spirit behind CIAP itself, a community where professionals and business owners help one another succeed.
Connect with CIAP
You can learn more about Orlando and his work at Pastore Business Solutions, and find his listing in the CIAP Business Directory.
CIAP welcomes Italian-American professionals, entrepreneurs, organizations, and businesses across Chicagoland. Monthly breakfast meetings resume in January 2027, and our weekly Italian wine features continue. Explore membership options, see what’s coming up on our events page, or browse the directory to meet the people behind local businesses.
Know someone whose story should be featured next? Contact Salvatore at salvatore@chicagolanditalians.com. We’d love to hear from you, and we’re proud to share the stories of the people who make this community what it is.