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.
Leading with Transparency: Lessons in Open-Book Culture with John Costello
CEOs Unscripted
57 minutes
6 months ago
Leading with Transparency: Lessons in Open-Book Culture with John Costello
What happens when a 16-year-old managing adults becomes a CEO of a niche manufacturing company? In this candid and inspiring episode of CEOs Unscripted, host Jane Gentry sits down with John Costello, CEO of Cherry’s Industrial Equipment, for a real conversation about leadership, legacy, and the power of transparency.
From navigating a tense business partnership to building a company culture rooted in open-book management and financial literacy, John shares the unfiltered wisdom only earned through decades of gritty experience.
Jane and John explore the weight of leadership, how to foster a culture of financial literacy, and why transparency is one of the most overlooked competitive advantages in mid-market companies — all while keeping a sense of humor and humility.
(07:31) The value of teaching financial literacy at home (11:38) The bittersweet buyout story and hard lessons from a forced 50/50 partnership (19:52) John's hard-earned advice for CEOs entering business partnerships — and the questions he wishes he’d asked early on (25:11) Why John embraced open-book management — and how transparency with financials built trust, ownership, and accountability across the team (27:38) Teaching financial literacy to employees as a company benefit and its impact on employees’ personal lives (37:39) How one employee’s idea saved $25K and proved the model works (38:34) Why weekly meetings, forecasting, and cadence are key to strategic execution (40:27) The radical transparency used in their recruiting process (42:23) How leadership evolved under this model — and why it’s working (53:58) Reflections on legacy, transitions, and developing people through culture
If you’ve ever questioned how open is too open with your team, or whether your culture really drives performance, this one’s for you.
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.
