CEO's You Should Know - Pittsburgh Podcast By iHeartRadio Pittsburgh cover art

CEO's You Should Know - Pittsburgh

CEO's You Should Know - Pittsburgh

By: iHeartRadio Pittsburgh
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As part of iHeartMedia’s commitment to the communities we serve, we are introducing CEO's You Should Know, a weekly podcast feature that profiles the businesses that drive our regional economy. CEO’s included in these episodes will represent small, large, local and international firms because all play a part in driving Pittsburgh's business community.iHeartRadio Politics & Government
Episodes
  • CEO, Sam Milligan of Cousins Roofing Siding & Decks

    CEO, Sam Milligan of Cousins Roofing Siding & Decks
    Mar 18 2026
    On this episode of CEOs You Should Know, we sit down with Sam Milligan, co-owner of Cousins Roofing, Siding & Decks—one of the fastest-growing, family-owned exterior remodeling companies in the Pittsburgh region.

    What started humbly—building decks out of pickup trucks alongside his cousin and business partner Calvin—has grown into a trusted name in roofing, siding, and custom outdoor living spaces.

    Sam shares how he helped transform the company from its early days as CNS Construction into the Cousins brand you see today, built on craftsmanship, integrity, and a commitment to treating every home like it’s their own. While Calvin didn’t participate in this interview, his role as co-founder and partner remains central to the company’s story and success.

    From scaling a business in a competitive industry to building a reputation rooted in trust, relationships, and community impact, this conversation dives into what it really takes to grow a family business the right way.

    If you’ve ever wondered how hustle, values, and a little Pittsburgh grit can turn a small operation into a regional powerhouse—this is an episode you won’t want to miss.

    https://www.callthecousins.com/
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    16 mins
  • CEO, Jackie Danko of Sound Advice Entertainment

    CEO, Jackie Danko of Sound Advice Entertainment
    Mar 5 2026
    Great events don’t happen by accident. Behind every unforgettable wedding, festival, or corporate celebration is someone making sure the right talent meets the right moment.

    In this episode of CEOs You Should Know, we talk with Jackie Danko, Founder and President of Sound Advice Entertainment, a Pittsburgh-based full-service entertainment and event booking agency. For more than a decade, Jackie has been connecting clients with musicians, DJs, specialty acts, and speakers—helping create memorable experiences across weddings, corporate events, festivals, retirement communities, and private parties.

    Jackie shares how she turned a lifelong passion for music into a thriving business, the art of matching performers with the perfect audience, and why relationships and reputation are everything in the entertainment industry. We also talk about her life as a performer with The Joe & Jackie Show and The Pittsburgh PolkaMeisters, and how being on stage shapes the way she runs her company.

    It’s a conversation about entrepreneurship, creativity, and the business of bringing people together through music and entertainment.
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    16 mins
  • CEO, Brian McMahon of Ace Handyman Services

    CEO, Brian McMahon of Ace Handyman Services
    Feb 25 2026
    In this episode of CEOs You Should Know, we sit down with Brian McMahon — an entrepreneurial powerhouse who took the reins of his family’s business and transformed it into one of South Pittsburgh’s go-to home improvement and repair teams. As Owner and CEO of Ace Handyman Services South Pittsburgh, Brian brings over 7 years of hands-on leadership and business management experience to a company that helps homeowners and businesses solve their toughest property needs.

    From his early hustle — kicking off ventures as a teen — to mastering the art of running a local services company, Brian’s journey is a testament to grit, community focus, and smart scaling. Under his guidance, Ace Handyman Services has become a trusted name across Monongahela, Bethel Park, West Mifflin, and beyond, tackling everything from drywall and carpentry to aging-in-place renovations with integrity and craft.

    In this conversation we explore:
    • How Brian’s entrepreneurial spirit shaped his leadership style
    • Turning a hobby-driven start into a thriving home services business
    • The balance between hands-on craftsmanship and strategic management
    • What it takes to build trust in your community one customer at a time
    If you’re curious about leadership lessons from someone who literally helps keep homes running — and who believes no job is too small — this is a CEO worth meeting.
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    17 mins
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