Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
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Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
How This CEO Built a $160M Firm While Staying 100% Independent | Thomas Grealish
CEOs Unscripted
58 minutes
1 month ago
How This CEO Built a $160M Firm While Staying 100% Independent | Thomas Grealish
In this powerful episode of CEOs Unscripted, host Jane Gentry sits down with Thomas Grealish, leader of Henderson Brothers, one of Pittsburgh's most respected independent insurance and financial services firms with over 160 employees.
What You'll Learn:
🔹 Culture as Competitive Advantage - How Henderson Brothers protects their independence and uses culture to naturally "weed out" bad fits while attracting top talent
🔹 The Stay Interview Strategy - Why Thomas asks employees two critical questions about leaving (before they ever consider it) and how this prevents turnover
🔹 Hiring Without Mistakes - The "messy but effective" referral-based hiring process that prioritizes cultural fit over impressive resumes
🔹 The Two-Minute Drill - Thomas's crisis preparation exercise that helped his team navigate the 2008 financial crisis, tech bubble, and COVID without panic
🔹 Financial Transparency That Works - How sharing P&L statements weekly creates ownership mentality across the entire organization
🔹 Strategic Growth Done Right - Expanding to Columbus, Ohio organically while maintaining culture remotely
🔹 Community Giving as Leadership Development - Why Thomas encourages 30-year-olds to join nonprofit boards and how Henderson Brothers supports employee philanthropy
🔹 Family Business Survival - Navigating 40+ years in a family business with his brother while maintaining alignment on vision and values
Key Timestamps:
00:00 - Introduction & Pittsburgh Culture 04:32 - Culture as Everything: Independence & Heroic Service 09:15 - The Stay Interview: Two Questions Every CEO Should Ask 14:20 - Hiring Process: Slow, Careful & Referral-Based 18:45 - The Two-Minute Crisis Drill That Prepares Teams 23:10 - Financial Transparency & Weekly P&L Sharing 28:30 - Operationalizing Culture as You Scale 33:15 - Community Philanthropy & Developing Young Leaders 38:40 - The Mario Lemieux Foundation Story 42:20 - Strategic Expansion to Columbus, Ohio 46:15 - Family Business: Alignment & Good Intent 51:30 - Rapid Fire: Books, Career Advice & Getting Unstuck
About Thomas Grealish: Thomas has led Henderson Brothers for decades, growing it into a major regional insurance and financial services firm while maintaining private ownership and a culture-first approach. He serves on multiple nonprofit boards including the Mario Lemieux Foundation and is a Duquesne University graduate deeply committed to the Pittsburgh community.
About CEOs Unscripted: CEOs Unscripted is a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Host Jane Gentry, a veteran consultant and former mid-market CEO herself, delivers unfiltered conversations with founders and executives navigating the unique challenges of leading $10M-$500M companies. No fluff, no jargon—just real talk that drives real growth.
Subscribe for More Leadership Insights: New episodes drop bi-weekly featuring candid conversations with CEOs who've scaled businesses, navigated crises, and built lasting organizations.
Tags: CEO leadership, company culture, mid-market business, family business, hiring strategy, organizational development, business growth, Pittsburgh business, insurance industry, leadership podcast, executive coaching, crisis management, corporate culture, talent retention, strategic planning, employee engagement, business scaling, CEO interview, entrepreneurship, business strategy, workplace culture, leadership development, talent management, business expansion, independent business, private company, heroic service, stay interviews, financial transparency, nonprofit leadership, community impact, succession planning, organizational culture, CEO advice, business podcast, executive leadership, team building, business management, regional growth, family business leadership
Related Topics: #CEOLeadership #CompanyCulture #MidMarketBusiness #FamilyBusiness #HiringStrategy #OrganizationalDevelopment #BusinessGrowth #PittsburghBusiness #InsuranceIndustry #LeadershipP
CEOs Unscripted
Real Talk. Real Growth. Real Results in the Mid-Market
Jane Gentry consulted in enterprise for 20 years. And, after being a CEO in a mid-sized company, she realized why they say it is loneliest at the top. Mid-market CEOs learn their craft through trial and error or by reaching outside their organization for help. She launched CEOs Unscripted as a bi-weekly podcast by mid-market CEOs for mid-market CEOs. Our purpose is to provide insight into the unscripted, unfiltered journeys of CEOs and Founders as they talk about their wins, losses, lessons and playbooks for growing and scaling their organizations. There is no better forum than learning from your peers.
