A leadership journey built on transparency, hard lessons, and culture-first decisions.
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.
Episode Highlights
- (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
- (29:34) Jane recommends reading Financial Intelligence by Karen Berman, Joe Knight and John Case
- (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.
Episode Guest
John Costello is responsible for the overall development and success of Cherry’s Industrial Equipment Corporation. John started out in the company as a sales assistant and moved up through the ranks to manager, partner and sole owner during his 30-year tenure. John has been a leader and advocate for employee engagement and financial literacy, implementing open book management in 2018 with tremendous results.
John lives in Illinois with his wife Kim, three beautiful kids Jack, Grace and Leah and their dog Millie who is adored and loved by all.
John attended Northern Illinois University. He belongs to several industry professional associations and actively participates in the open book community GGOB.
About Jane Gentry
Jane Gentry has had a successful 30-year career as a CEO, Business Consultant, Executive Coach, and Keynoter. Jane formed her practice in 1999 and since then has partnered with her clients to improve growth, profitability, client retention, employee retention, leadership capabilities and business value.
Jane leverages strategies including the proprietary Value Blueprint to enable business owners and leaders to successfully create healthy organizations, plan for succession or sell their businesses for the highest possible market value. Jane is considered one of the top voices in leadership and sales.
Rate, Review & Follow
Enjoying CEOs Unscripted? We’d love to hear your thoughts! Leaving a quick rating and review not only supports the show but also helps other leaders discover conversations that can elevate their business journey.
Don’t forget to follow the podcast, too! With more insightful episodes and unfiltered conversations on the way, you won’t want to miss what’s next.
CEOs Unscripted
Where Real Talk Drives Real Growth And Delivers Real Results For Mid-market Leaders.
Welcome to CEOs Unscripted, the podcast where real talk drives real growth and delivers real results for mid-market leaders. Each episode offers an unfiltered, behind-the-scenes look at the wins, the losses, and the playbooks shared by CEOs, founders, and executives. Grab a seat and join us for unscripted, honest conversations about what it takes to lead, grow, and scale in today’s business landscape.
