Summary
AI Grace
In this conversation, Jon Penland shares his fascinating career journey, starting with an unexpected stint selling water pumps after losing his job in residential construction. Living in Northeast Georgia with his wife and a young child, Jon initially took a job running a drill press in a company known for its excellent workplace culture. Encouraged by his manager, Jon transitioned into sales, where he sold complex centrifugal pumping units. This role, while fulfilling, began to seem limiting after an RV trip sparked a desire for a lifestyle change. This ultimately led him to explore opportunities in the burgeoning internet industry, reminiscent of a similar path taken by the host, Bud Kraus.
Jon and his wife shared an interest in the RV lifestyle, which led them to travel across several states while he pursued freelancing opportunities. He started as a freelance writer for various websites, including WPMU Dev and WhoIsHostingThis, before becoming involved with Kinsta. Jon also emphasizes the role of physical fitness in maintaining his mental and physical well-being. His commitment to regular exercise, particularly body weight exercises and running, has significantly improved his quality of life over the years.
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While working as a freelance writer, Jon joined Kinsta as a support engineer. His journey at Kinsta mirrors his earlier experience; he steadily advanced through various roles, from head of sales and support to chief operating officer. In these positions, he built and refined the company’s operations, human resources, IT, and legal functions. His efforts culminated in his recent promotion to CEO as of September 1, 2025, following a year-long transition where he successfully managed Kinsta’s sales and marketing efforts.
Jon discusses the importance of physical exercise, particularly running, in his life. He believes that maintaining fitness is crucial for overall well-being, which includes mental clarity, better sleep, and enhanced daily performance. As an avid runner, he participates in trail races and enjoys the process as much as the physical benefits. His dedication to running, coupled with his disciplined approach to fitness, has made him feel better in his 40s than he did in his 30s.
Throughout the interview, Jon highlights the importance of not settling for an unfulfilling career. He advocates for taking risks and making career changes if it means pursuing a life without regret. His story is one of persistence, learning, and adaptation, demonstrating how career shifts, dedication to family, and personal growth can lead to unexpected and rewarding outcomes. Additionally, Jon touches on the challenges and rewards of being a leader in a dynamic industry, underscoring the significance of strategic planning and team-building in business success.